I was in the pub having the usual after work drink before heading home for my take away tea, when Steve starting chatting about an unusual incident he had had that afternoon.
Steve is a plasterer and so when he starts a wall he ends up having to finish it, no leaving it and coming back tomorrow, so when the customer asked if he was nearly finished and what time he would be done, Steve explianed how it was likely to be a good two hours before he was ready to leave. The customer a pleasant enough bloke who I had done work for in the past, became flustered and paced about a bit so Steve says, then said something like 'It's no good I shall have to get ready or I'll be late' Steve thought nothing of this and got on with his work, aware that the man was spending a long time upstairs getting ready. Now comes the good bit. Steve says he was tidying up the tools when he saw a rather striking woman come down the stairs, at first he thought she had got in without him noticing and had been to see John the customer, about to say sorry and step to one side, he picked up on the general image of the woman and realised that it was not a woman but John. He still said sorry and stepped to one side, the 'thank you' in response confirmed this good looking woman was in fact his customer and was now 'ready' to go out. Steve says he made a polite but quick tidy up and left, his next stop being the pub and our chat.
His dilemma now was that he was meant to go back the next day and finish the room off but he was embarrassed about what he had seen. I tried to be helpful and say it is work and pays the bills, that John would have said something if he was offended by Steve's actions, then as a tease I suggested that if John was that good looking why not ask him/her out. He choked on his beer.
I heard nothing more of Steve for a week, so when I did, I asked him how the job had gone. He had indeed finished the job, and been paid. I pushed a little farther asking if John had said anything. Steve told me John had not said anything as such at the time, and it was not John but Jenny, 'oh' I said and asked for more detail. Steve had turned up at eight the next morning as usual but instead of John letting him in it was Jenny, dressed in nightie and wrap. Now this was getting interesting. He says he went in and started to set up for the next part of the job, Jenny brought him a cup of tea and asked if Steve had any objections to the way he was dressed. I can imagine Steve stumbling over his words as he said he was fine with him/her dressing however they liked and just got on with the job.
Mid morning and Jenny is still about and makes Steve another drink, this time Steve says in a smart trouser suit, silk blouse showing enough chest to imagine what is down there and the reddest stiletoes he had ever seen. 'Still a looker?' I asked 'Oh yes' he confirmed. Steve was then left on his own to get on with the plastering as Jenny was going out. He made some comment about how John, sorry Jenny must have some balls to go out dressed like that in broad daylight, he could never imagine doing anything like that.
Late afternoon, Jenny returns with some shopping, Jenny makes him a drink then asks if Steve minds doing a favour, Steve says 'ok' and Jenny says she wants his opinion as a man on a new outfit she has just bought. Steve has agreed to this but worries what he has let himself in for. Fifteen minutes later he says there is a knock on his door and there is stood Jenny in a black and grey dress, virtually nothing to it he says, a short black underdress with a see through grey dress over it, black tights and towering black heels. Jenny asked him what he thought, but he was lost for words, this was a woman to lust after but he knew it to be a man, I knew he would be confused, Steve said he opened his mouth but could not think what to say and just stood there, Jenny said that was a perfect reaction and went off to change once more. This time into jeans and a shirt Steve said but I guess it would have been a blouse. Then when he is finished Jenny makes him a coffee and pays him, but to confuse the poor man further asks him what he felt about having Jenny about instead of John. Steve apparently said it made no difference to him, and then for some reason said the tea always tastes better when made by a woman.
Anyway I rather expected that to be an end to the story, I had done the electric a while back and thought the house must be pretty much renovated by then, I was wrong. A few weeks later Steve told me that he had been asked to do some more work at the house, I asked if he was taking it, he said yes, so I asked him to keep me informed if anything interesting happens.
I saw him after his first day and asked how it had gone. He said the first cup of tea was from Jenny in nightwear, then John reappeared and went out for the day, coming back late afternoon. But before he finished Jenny was back in a skirt and heels. Over a last drink Steve found out that the short dress he had viewed had indeed been a big success according to Jenny, Steve was clearly getting more comfortable with this person and asked if it was for a special occasion, Jenny said it was to celebrate a first anniversary which Steve took to be of a romantic sort. I asked him how he felt about such things, he surprised me by saying he would take her out if he did not know the truth, 'and seeing how you do know the truth?' he went all flustered and said something about the plumbing being all wrong and it would be awkward if it got all hot and sexy. So I told him girls like Jenny who like men have it all that worked out, to which he blushed some more. When we parted I found out he would be at the house at least two weeks doing various decorating and finishing jobs and flippantly suggested that he ought to be careful Jenny might have him under her spell by the end.
It was two weeks later that I saw Steve next in the pub, he could not stop as he was going out, 'anyone I know' I asked he just said 'yes' and was gone. Later the next week I got a full run down of the evening but not before I had pieced together his previous two weeks. Steve says Jenny was about most of the time only once did he meet with John. It seems Jenny kept Steve supplied with drinks and work for a couple of days, then as they were getting used to each other Jenny asked Steve if he was offended by Jenny being a man, Steve must have said not because he somehow ended up agreeing to going out with Jenny the day after to a Mexican restaurant. He said they had a great time, at first he was nervous that people would make comments about Jenny, but even though he knew it seemed no one else picked up on the fact that they were in fact both men. After a while I could tell Steve was getting a buzz from being out with Jenny from the way he talked and the news that they had been out more than the once. I asked about the anniversary, it was not a romantic year like I might note but for Jenny it was a year since her first day out in the world as Jenny. And the sexy dress, Steve told me that was Jenny going out on a first planned date with a man, 'oh' I said 'It did not last the night, he was a knob just wanted inside her knickers' I paused to answer 'but in a dress like you described what did she expect?' 'My thoughts exactly' he agreed.
It appeared Steve had been working hard through the day and busy at night as well. They had been for meals out, had a drive in the countryside, gone clubbing one Saturday, all the things I would expect to do with a girl if I had one. When I left and suggested he could keep me informed, he replied that he was not sure how often he would make it to the pub in the future, I just said 'Jenny' he nodded a yes.
A week or so after that I needed to see Steve and ask him to look at a job, so on a chance I drove past the house, I was in luck his van was outside. I knocked on the door and was greeted by a rather good looking lady, her cream dress covering a great figure. 'I am looking for Steve' I hoped this was the right house as the woman did not look like a drag queen. 'Steve' she called 'for you'. Steve came to the door, I forgot all about the work I wanted him to do, 'Is that her? Jenny?' 'yep' 'bloody hell Steve you sure she is you know not for real?' 'yep' he said with a big smile. I now knew why he was not at the pub that much lately, 'and the other you know what' he acted dumb 'what?' 'the plumbing' I asked 'oh that is fine, like you said she is not the first to be made that way' I must have looked bad because he asked if I was fine, I was just thinking about them together and having trouble thinking of Jenny as anything but a girl.
My life as a student came to an end as the degrees were handed out, and with that bit of paper came a new start. I had managed to get myself a job in the civil service, but it meant a move to another city. Three years ago I had left home for one city, now I was moving to another, but this time without the student halls to live in, I had to find my own way. I was all grown up and fully independent. Luckily when I went for my induction day, I noticed an advert for a house share. I followed it up and the bloke seemed ok to get on with, worked in a department near to the one I was starting in, so he would be able to help me get sorted and find my way about. Things were falling nicely into place.
After a few weeks, I would not say we had become close friends, but we often ate together and shared a beer while watching TV. Matt was ambitious and liked to lead, whereas I naturally went for the easy life, which would be significant later on. It was a Saturday evening that things changed. Matt and myself found ourselves in with nothing to do but get a take away pizza and some vodka. We watched TV, chatted and got drunk. I am not sure how we got there, maybe not having girlfriends meant we made up stories about our sex adventures, but we got onto what cum tastes like. I had tasted my own just to see, but Matt talked about how everyone's is different, and somehow I asked if I could taste his! He agreed if I sucked him. I rather liked it when ex girlfriends had done that to me, and kind of wondered what it might be like to do it. I was just about ready to have my first attempt at gay sex, when Matt suggested I dress up as a girl because he did not like the idea of being sucked by a bloke. He even had a case of stuff an ex girlfriend had left behind.Wig, blouse, skirt and some underwear.
Being drunk and excited by all the sex talk, I was soon in my room stripping off and emptying the case to see what there was. Just a plain skirt and blouse with a long blonde wig, which took a little brushing to make decent. The clothes fitted just about right, and I walked in on Matt saying 'ta da' as I entered. He assured me it would do for a start, and startled me with a kiss and bit of groping. This was all new to me, so i followed his lead and soon had for the first time, another man's cock in my hand. It felt soft, yet hard and pulsing. 'So are you going to try it for taste?' As he sat, I knelt between his feet and touched it with my tongue, then my lips, the hair was falling forward across his hips and I became very aware of how I was dressed. I was a girl in a girl's position ready to let Matt get satisfaction without returning the compliment. And then it happened, hot cum filled my mouth as Matt thrust his cock into my mouth. I was amazed at how it felt to be on the receiving end instead of the giving as it were, but still I was there swallowing his salty stuff. I even licked it clean. I would never call myself gay, but as I got up off my knees I became conscious that my own cock was standing to attention. 'Someone liked that?' Matt suggested and pulled me back down to sit beside him. 'I think we could have a little fun, me and you.' He stroked my erection through the skirt and kissed me. 'I think I shall get you some clothes that fit you better, maybe some heels and definitely some red lipstick.' I was about to explode as he stopped stroking and kissed me again.
He talked about the sort of clothes that he might buy for me, and how heels look good on my feet. I was so excited by his previous attention and the images he was putting into my head that my erection remained stiff. I asked him if he would return the favour and suck me, but he declined, saying I was his girl and he would screw me if I wanted, but he did not like the idea of him being at my feet. I was going to get up and relieve myself when he caught my hand. 'I have an idea to ease your pressure, how about I show you what a great time you could have as my girl?' He was not touching my cock but his hand was round the back and finding it's way into my hole. My arousal had hardy waned, but with a finger inside me and touching something sensitive, I was back to full attention. Our kissing picked up it's passion once more and before long, I was lying on the floor with him on top and filling my arse with his recovered cock. I was desperate for some relief, and as he pushed further in and stimulated me deep inside, I got it. I pulled him close, getting his cock as deep inside as possible, and for the first time ever, I screamed as I came, telling him to push harder. I exploded and all too soon both of us wilted and left our cum on my body, his inside, mine on my skirt.
Well that was how it started. The following hours and days I was riddled with guilt, regret, and self loathing for allowing myself to do such things, but life is never that simple. Maybe things would have worked out differently if those were my only thoughts, but they were not, I also had an overwhelming desire to do it again, I wanted to find out if it had been as good as I thought it had been. Did I really scream at him to push harder, just like Janice once had a year or so ago when I finally got her into bed?
Whatever my thoughts, Matt seemed to be focussed and was busy buying stuff online. By Monday evening I had told him my waist size, shoe size and any other measurement he asked me for. By Wednesday, the parcels were waiting for us when we got home from work. He would casually pick them up and stash them in his room, but I knew without asking what they contained and it did nothing for my thoughts.
Saturday afternoon arrived, and we had not even so much as mentioned the previous Saturdays activities and I was wondering if I was wrong about the parcels and he was just teasing me. After a short conversation following our usual domestic cleaning routine, where we established that neither of us had plans for the evening, Matt suggested that he might get us a take away and wine if his girl from last weekend fancied joining him. I could have said no but I didn't. I asked him for a korma and red wine, he said there were some things in his room that will suit me, and I dutifully went to find them.
Everything was laid out for me, dress, heels, underwear, stockings, wig, lipstick. And without questioning it, i undressed and changed into the outfit he had bought me. The anticipation had me hard and spoiling the fall of the dress before I slipped my feet into the shoes, a moment in front of the mirror to apply the red lipstick and I thought I had about cracked it. I heard the door open as he came back with the food, so I stepped out into the hall, gave him a kiss and greeted him with 'Hello my dear, I was just about to get the plates out. As I walked away, I felt a hand on my arse. 'You look great, hope everything fitted?' And so the new roles played out. I put the food out like my mother would have done, he opened the wine and then sat down to be served, which I did. Matt taking every opportunity to touch me and make comments, some flattering, some lewd. And I just loved i. He made me feel wanted and desired, something no girl had ever done to me before. The evening turned into a regular sort of date scenario. After the food, we watched a film while cuddling and kissing. Later on we got ourselves pretty excited and he suggested his bed and lead me to my fate of sex with him in his bed. I was still there in the morning still in my underwear and wondering why I had fallen so easily into this pseudo gay relationship.
'Last night was good, wasn't it?'
I had not realised he was awake. 'Oh I don't know, this is all rather new to m,e and I am not sure.'
'You are joking, your hole must be so sore after you had me screw you for so long.'
'I did, didn't ?. You just make me so, oh I don't know.'
'Sexy? because that is what you are. I could have you again right now.'
'Of course I could.'
And with that the talking stopped, and he started to arouse me again, until I once more had his cock buried inside me and me enjoying another orgasm of his making.
When I had come down, he lay beside me, 'Told you I could'
I acknowledged this ' yes you did'
'And you know why?'
'Because you are my girl and I am your man.' He seemed to tower over me as he said this, somehow emphasising our new relationship of his dominant male position to my feminine submissive role.
The weeks passed, and once a week I would play out my girlfriend role. He treated me to new clothes, which were always on the short side, and heels which were always on the high side, but I never objected as I liked the sex, and the dressing up was just foreplay to me. It got me in the mood and made me feel attractive. The dressing got more involved over the weeks. Matt would perhaps buy me some make up, or a lady shaver, and that weekend I would endeavour to make the most of it. So after a couple of months, I had a hairless body, some basic skills picked up off the internet about make up, and quite a growing wardrobe.
This dress with the sheer top was Matt's favourite, especially once he had bought me some fillers to slip inside the black lace bra.
It was not just the free weekend evenings that were becoming dominated by our new passion. After a few months, it was starting to spill over into the rest of our lives. I have already mentioned being hairless, well who ever saw a woman with dark hairs poking through her tights, or in my case stockings. So in the bathroom there was the beginnings of a feminine presence, as I got a lady razor and some cosmetics, which included a tinted moisturiser so I could have a tanned look and soft skin. My hair was another part of my life that was affected. I always had longish but neat hair, but with the idea of being able to go without the wig, I stopped my regular barber visit and let it grow, expecting someone in the office to comment and when that happened, I told myself I would get it trimmed, but so far no one had made a remark. I did make one very conscious decision, well more Matt prompted me, then told me to get it done because he would like to get me some nice ear rings. So with a stomach full of butterflies one Saturday, I had a stud injected into my lobes. I now had a visible dramatic change to my everyday appearance, and dreaded Monday after a great weekend being told how pretty I will look when they heal and I can wear proper costume jewelry. I might have dreaded Monday, but when it happened no one seemed to notice. A couple of girls made a remark and one bloke who had his ears pierced as well said 'welcome to the club mate.' And that was it. I had what I thought were glaringly feminine studs and no one minded.
Once I had allowed the holes to heal and was ok with removing the studs, I got some alternative understated studs and tiny hoops, but Matt bought me a pair of long pendants which brushed my shoulders. He said they made me even more pretty and attractive, with them in I just felt more feminine, but then I was also in heels and a dress.
Our behaviour changed as well. Matt was always the more confident of the two of us, and encouraged me to play the traditional female role when in a dress. We stopped getting take-aways and I started cooking for us both, doing the whole meal in a dress then setting the table, serving him when he got in from whatever he was doing. I found the lengthening periods in a dress just as exhilarating and would look forward to the weekend not just for the sex but for the opportunity to be pretty. But this relationship change leaked into the rest of the week, and if I was cooking for myself i would ask Matt if he would like to join me, often he said yes and I would cook for us both in virtually the same way as a weekend, just I was not in a dress as I had just come home from work.
As the winter came and the dark nights, things moved on a little more. I was going out for a jog to try and keep fit a few evenings a week, and as you might expect would come home sweaty, so I would shower and dress in something casual for the evening. Matt at first bought me pink sweats like this.
But I felt awkward, being a sort of half way male/female, but he said it was fine, just the two of us, and it was so much easier to slip into the pants and top before starting on the dinner. So come December, I was moving between a suited man at work and a rather camp man in the evening, then becoming Matt's girlfriend on the weekend. And Matt was still prompting, encouraging even, telling me on occasion what he would like me to do next. He wanted me to do my nails with polish, but I bite them, so I agreed to paint my toe nails for him, which kind of became fulltime, and over time I managed to stop chewing my fingers, mostly down to his nagging and my desire to have nails like the pretty girls at work. Ok I would not be growing them long, but just neat would be good.
It took a while, but this was how they ended up and I have to say I was proud of the achievement, but I know this is what Matt would prefer. And if I am honest, what I think a good looking girl's nails should look like.
But no way could I go to work with them coloured or that long. It would be sure to raise more than one eye brow. Talking of eye brows, that was something else that slowly changed. At the start I had regular nondescript brows, but if you pluck a few out each weekend when you are following a make up guide and tell yourself you are just making them neater. Well over time they become narrower, until one day you look at yourself on a weekday and ask 'What have I done?' But it is too late by then, and I just had to live with the feminine tadpoles above my eyes.
Well Christmas was a surprise in a way, but I should have expected what happened next. We would be going to see our families at Christmas, so nothing special was planned between us, but we did buy gifts for each other. I bought Matt some aftershave that I knew he liked and felt was safe, and rather expected him to get me something similar. Well he did in a way. He bought me some scent and it was definitely not a masculine smell, pretty lavender tones made it's use quite clear.
The weekend before Christmas, I made him a turkey meal, all the trimmings which included me. I went to special lengths to look my most feminine for him, and he did not disappoint. I woke beside him in the morning wearing his latest gift, a silk nightie and feeling satisfied I had been properly taken by my man. I was leaking for hours, and had trouble walking due to my arse being so sore. But I was happy and wore the nightie late into the morning until I had to get dressed and go out.
I had not seen my parents for six months, and turned up at the station where my mother had agreed to pick me up from. She gave me a strange look as we greeted with a hug, and then stood back, giving me an appraising look. 'You look different.' She stated.
'Do I ? taking a little more care of myself now.'
'Is that it? You have not had your hair cut for months it looks like.'
'Can't decide how to have it.'
'Oh and you have stopped chewing your nails.'
'Yes, that took some willpower.'
'I guess so, what happened to your eye brows then?'
'Just tidied them up.'
'Got carried away it looks like.'
'And the ears?'
I smiled and changed the subject, just in case I said something incriminating.
Three days with my folks and I was ready for going back to work. That and mother noticed my hairless arms and did not really seem to accept the story that I was swimming more and it helped.
Matt was back before me and had another gift for me. Said he had been shopping on Boxing day and bought something for his girlfriend. I was amazed by what I found in the bag. A full length nightie and wrap in the softest fabric I had ever felt. He suggested I go and try it on, which I did not need asking to do twice. I returned a short while later with the wig on and some lipstick as well. The fabric wrapped itself around my legs in a most luxurious way. It felt wonderful and I could not help but strut over to him to thank him with a kiss and some playtime in bed. I wore it until the next morning, when I had to go to work, but it was the start of my first fulltime wearing of female clothing. I now had two items of sleep wear, and never went to bed without wearing one of them. They just made me feel so nice as I slipped between my sheets every night.
New year in the city brought with it an opportunity that I had never considered, going out with Matt. It took a lot of persuasion, but he had a few days between the 25th and the 31st to really work on me. Things like I look really good, no one will take a second look, it will be a great buzz, everyone will be too drunk to care even if they do read you. In the end, I relented when he said he had asked if a ladies salon a few streets away would do my make up for me. He had told them some tale about it being a bet for a party, but the plan was to just visit a few bars and end up in the city centre at midnight. I turned up on the shop step terrified as to what I had let myself in for. A middle aged woman knew exactly who I was. Not many men venture into her shop, so I was a bit obvious. I had been told to fetch some clothes to go home in and my wig, which I had clutched in a bag. Sally was very patient with me and kept me at the back of the salon so I was not on show while she painted my face and styled the wig. I never asked her to, but as she worked she explained what she was doing and I eagerly soaked up her lesson in the dark arts of using make up well. I left in the sweats, at the time I thought them the easiest to carry, but when Sally had finished I wished I had brought a dress, but that was for later. It was only mid afternoon and there was plenty of time before we would be catching the bus into town.
The walk home was as terrifying as I expected. It is one thing to walk about at home looking like a woman, but to walk down a street and a busy one at that, meant I was being seen by loads of strangers, any or all of them could laugh, tease, make rude comments or just abuse me for being who I was, a man in a dress. It was not normal, but I did not want to be normal. I wanted to be Matt's girlfriend and just this once go out with him like a normal couple. I made it back without incident, and found Matt watching football, something I never understood. So seeing how I was looking the part, I started on some housework, cleaning my room and doing our ironing. Matt did try to kiss me but I told him only a quick one. I did not want him messing up Sally's hard work, so he just went for some groping and kissing my neck as he cuddled me from behind. I was loving the confidence Sally's work had given me. and loving the reaction I was getting from Matt. After I had cooked us something to eat, I changed. Matt wanted me to wear the sheer top dress, but I added control pants so my manhood would not give me away, as I was sure it would tent the dress at some point in the evening. It always had in the past, so why not this evening as well. About eight we were ready, cock squashed, nails painted, bra visible through the dress, stockings on my legs and fortunately a coat on my shoulders. It was a cold night and the coat had to be bought specially for this occasion. I slipped my hand into Matt's as we walked out of the door, for physical and mental support. This was going to be an exciting and nerve wracking experience and I was not doing it alone. Matt was going to have to be there for me if it started going wrong.
A few things struck me straight away. Cool air on nearly bare legs is quite invigorating, and heels make a distinctive clicking noise on paving flags. I was enjoying myself, which was a good start. Sitting on public transport is something I am familiar with, but not when dressed as I was that evening. My knees seemed to very obvious and my nerves about to snap whenever anybody tried to squeeze past. Eventually Matt led us into a bar and bought me a typical girl drink, a bright red cocktail. I sipped it while he took glugs from his bottle of lager. There was plenty of people about making plenty of noise and having fun. Soon I was getting into the spirit of the night, chatting to a few people which was a challenge, as I hoped my voice was not too deep and gave me away. One drunken man started chatting me up while Matt was at the bar getting me another cocktail, but soon got the message when my man returned with the drinks, giving me one and putting his now free hand rather proprietorially round my waist before giving me a kiss.
I was Matt's girl, and rather like a wild animal he was making it clear I was his and the other bloke should back off, which he did and I fell just a little further into the position of submissive partne,r happy to be by his side and feel protected. What a turnabout for me. I had always hopefully treated my girlfriends as equals, but now that I was the 'girlfriend', I was happy for him to be in charge. I was liking having a partner who made the decisions and wanted me to be happy. Maybe that was not how he saw it, but it was how I felt that night as we looked for the nicer bars and less drunk revellers. Come midnight, we were out in the main square dancing and singing with crowds of unknown strangers. A great time and a very different new year to previous ones. But it was not over, another drink and we decided to make our way home. Unfortunately the busses had virtually stopped, so we walked a bit as we knew it was only a couple of miles home. The error in this plan was that I had never walked anywhere in heels besides at home, and my feet were already tired. After a few streets, they were really complaining and stopped at a pub for one last drink and a rest. We made it home about three. My feet ached. I had tried stocking feet instead of heels, but that was just was uncomfortable. Finally we were at our door and it was a relief to walk on a soft carpet. I washed and cleansed before slipping into my nightie. I might have been tired, but I had had such a good time I slid my body into Matt's bed not really up for sex, but just wanting to be cuddled up to him and feel him there.
I had a couple of days off work following new years, and as I sat there nursing my hangover on 1 Jan, my body covered in the luxurious fabric of the nightie, I decided that it might be fun to stay as a girl until I had to go to work. This pleased Matt when he came home in the afternoon after going to a football match to find me in a dress, and even more pleased when I told him I had been to the corner shop and picked up some milk. He called me his girl and asked if I had a name, because he was not going to be calling me Alexander if we were out as a couple. I picked up on the mention of going out again. He said 'why not, other couples do it' I tried to say I thought it was all about sex for him. He quickly replied that it was to start, but seeing how much I have grown as a woman, and a woman that he likes the company of, he would be silly to not recognise that as a couple we make a good pair. I kissed him to say thank you for his support, but I ended up face down on the kitchen table wanting him to enjoy my arse hole. Not that it affected our lovemaking, but it was the first time he had encountered the control pants, and afterwards told me I would need to find another way of stopping my male pleasure showing as he preferred me in something rather sexier, as opposed to efficient.
After some time cleaning myself up, I experimented with tape and worked out how with strong surgical tape I could create the illusion of a female front. Just a hairy triangle showing with the unfeminine bits safely trapped facing backwards. This not only looked good but had the amusing twist of making me sit to take a pee, but Matt was happy to see me in the knickers he had been buying for me. I could now walk about the house in just underwear and unless you looked carefully, I was Matt's sexy girlfriend. It might have taken time, but between us we were creating the girlfriend of our dreams. Matt did not want a baggy shapeless girl. He wanted legs and curves, which is what I thought a girl should be as well, so it was easy for me to guess what he liked and fill that image, my reward being having him make love to me, which I was still enjoying enormously.
Well my New Year break passed very quickly. I spent the whole time being called Alexis and looking after my man, and he in return looked after his 'woman'. I even went to the shops for some groceries on my own. Scary, but I was finding out most of the firsts in this adventure were scary to begin with, but easing down to enjoyable or nothing later.
First day back at work in the new year and I had to be very careful when checking for any tell tale reminders of the break. I did not want even a hint of make up or nail polish. With the Alexander clothes on, I hoped no one would see or guess at my alter ego, but if I had an accident and ended up in A&E, then I would have some explaining to d. Not only was I hairless, and my toe nails red, but it hurt too much to pull the tape off, so I had left it on hoping no one noticed, but besides the pain there was the thought that I might as well leave it on as strip it off and redo it within a day or two. So I tried to walk and sit normally, hoping no one asked why I never used the urinals.
By the end of January, several things about my life and routine had changed, and all with my willing agreement. Matt was working longer hours, so I was getting home before him and would fill the time at first preparing an evening meal, maybe doing a little housework. He was always appreciative, especially if I had taken the trouble to change out of my work clothes into something more 'housewifey'. My wardrobe had a reorganisation. There was work clothes, Alexis clothes in the drawers and wardrobe but the casual Alexander choices were boxed up to make way for more dresses and heels, and I boxed up the Y fronts as I seemed to be keeping things tucked out of the way most of the time. The knickers felt more comfortable and more appropriate. The other big change was that I was sleeping in my own bed rarely. If I signalled my willingness for sex by wearing something from the Alexis side of the wardrobe, then Matt nearly always obliged by taking me to his bed and satisfying my needs, while I saw to his desires.
The other event was that I made a new friend, Marcus, who had commented on my ears when I got them pierce. Over the months, he had made remarks about the studs if I changed them, and rather strange conversations that you would not usually relate to a couple of blokes could be heard, as we discussed the error of wearing anything but gold, or the preference to stud or hoop sleepers, and which of the more decorative ones we wore was liked by the other. We must have sounded so camp, but I would still wonder if Marcus would notice and like my choice if I put in new studs. Then early February Matt went away for the weekend to see family, and after we discovered neither Marcus or myself had anything to do, we arranged to go to the pictures. I lived closer to the cinema, so Marcus would call on his way past. What I had not expected was his need for the toilet and his observational skills. As we walked out of the front door, he asked if a woman lived with me and Matt. I honestly replied 'no' and he knew my secret, bottles of female only products, a lady's razor, even make up was on show. When I realised my mistake, it was too late, but thankfully my friend did not seem to mind. In fact he seemed quite taken with the idea of me being even more 'femmy' than him. Being outed was not as bad as I thought it would be, mainly because Marcus was gay himself and liked to find himself in the arms of a nice man, as he put it, and being anything but butch settled for what he called bitch.
Finding this friendship and being able to talk freely about my situation with someone, unleashed the girl in me, and even though Matt was not about, I spent Saturday and Sunday as Alexis, making sure I was ready for Matt when he got home.
From that weekend on, I had myself a good friend. We joked that if we were female we would call ourselves girl friends. We discussed more than ear decoration, the whole gamut of our look was up for comment. I persuaded him to pluck his eyebrows, while he got me to finally get my hair trimmed. Eventually he persuaded me to meet him as Alexis, well it was like he knew all about me so why not show him my alter ego? This would be my first outing without Matt, and I was nervous, so I asked Matt to come with me which he agreed to. Maybe he had heard so much about Marcus that he wanted to see what he looked like, just like Marcus wanted to see what I looked like. The evening went off brilliantly. Marcus was more camp than usual and loved how well I passed for a girl. Matt I could tell was uncomfortable with Marcus. Men should be men he said later. My reply was obvious 'and what does that make me?' Without thinking, he responded 'My girlfriend.' I loved him for that honest answer and made sure his girlfriend was there for him.
The months passed and I was becoming a man only at work. Through Marcus and his circle of friends, I started to go out as Alexis, meeting up with other cross dressers and gay men, even the occasional woman who found pretty men interesting. Matt had his friends to talk football and sport with. I had mine to talk fashion with, but I was still very much Matt's girl. One big problem was family. I would put off returning home, mainly because I would rather spend the weekend in a dress than at home bored and in man jeans. But eventually I had to go for a family gathering.
As before, mum picked me up at the station, gave me a hug and unlike before told me I looked nice. Maybe it was the tidier hair, the smoother skin, the way I held myself. I thanked her and gently kissed her cheek rather like I would Marcus when we met out of work. The drive home was the usual catch up chat. How was I? Jean next door has had her operation, the dog over the road has died. That sort of stuff, and rather cleverly while my guard was down she slipped in a question about my partner being ok. I just thought of Matt and said 'He's fine' then wished there was a rewind on conversations. Mum just put a hand on mine 'It's alright dear, I have expected you to come out before now.' This opened up a whole new box of tricks, just what did she mean, how much do I tell her, will she be horrified, will it be a big falling out never to speak again? She slowly got some things about Matt out of me, and until the evening I was fine at keeping a lid on the full reasons for my not talking openly. Then we started on the wine as we prepared dinner, and by the end of the meal and the second bottle opened, she had weedled out of me why my eyebrows were neat, why my skin was smooth, why I sat to pee, why I had grown my hair long and why I had ear rings. She never asked about sex, but she needed little imagination to work out that I was Matt's girlfriend in our relationship. I attended the party on the Saturday and went back to Matt on the Sunday, her parting words as she dropped me off 'I shall have to come down and visit, meet you both, Matt and his girlfriend.' In the face of such a comment, I felt shocked and struggled to get the words out 'Oh yes sometime.' Before she kissed my cheeks and wished me well, leaving a shell shocked son on the pavement outside the station.
Well a few weeks later she had arranged her train tickets and told me she would be visiting. I told Matt, who rather liked the idea of meeting my mum. I was not so sure, she had met my one and only girlfriend when I was at school, but she wanted to meet me as
Alexis, as well as my boyfriend. So much that was not in the script for a normal son/mother relationship and I was going to have to handle it. I started with my wardrobe, which was definitely on the girlfriend to please Matt end of the clothing spectrum. I could hardly meet her in one of the sexy short dresses he liked, so I took myself off shopping with Marcus, who as my girlie friend was in on everything. Even though it was after work and we were both in shirt and tie mode, we still managed to walk round a few dress shops finally picking out a long summer dress we hoped would not be too revealing of my fake breasts, and would float and waft about my legs like I had seen other girls dresses doing.
This one we thought would fit the bill, a pair of beige wedge sandals and I was sorted. On the outside anyway, my insides were doing somersaults as the day drew closer, just what would she make of me?
She was arriving at Saturday midday, so I had all morning to prepare. Matt told me to stop stressing and tried to calm me with flattery, but left to go to a football match. I rang Marcus who helped calm the nerves, but it was me who had to walk out the door and meet mum at the station, and I had to do it on my own. The train was a little late, so by the time I saw her walking down the platform, I was a bag of nerves. The softness of the dress brushing against my legs lost on me. I was shocked but later pleased that she nearly walked right past me. If I had not said 'hi' I am sure she would have done. It took a second from looking at me to registering who I was, then a big smile spread across her face, maybe she had rehearsed it but it had the effect of subduing those butterflies.
We kissed a greeting, she told me the dress looked great and asked where I got it. She saw my heels and made some comment about how she can't wear anything that high, complimenting me on how well I walked in them. After that nervous start, the visit went really well. She chatted as though nothing had changed. Asked about work, told me about her gossip, made remarks about people being rude in cities as we jostled our way back home, and at times would ask me totally girlie things about my make up or nail colour. Matt came back after watching his team win, and took us both out for a meal at a nearby curry house, where mum probed him as she made her mind up about him. I gave her my bedroom for the night. She never even batted an eyelid at the suggestion as it was clear that the room was little used of late, and I would be sleeping with Matt. It must be strange to think of your child being all grown up and having intimate relationships with another person, but it must be stranger for mum. She only knew dad and a straight relationship, so her son being with another man in the next room must have been difficult.
On Sunday she stopped for lunch before heading home. Matt came to the station with us where she invited us both up to her home, making it clear that Alexis would be just as welcome as Alexander. I made it equally clear that coming out to her had been hard enough. I was hardly ready for her friends and neighbours, without even thinking about family. Needless to say I was exhausted by the time the evening came, but after a Saturday without sex, (well mum was in the next room,) I made Matt pleasure me and remind me why I going through all the hassle of cross dressing for him.
While I was learning all about being feminine, Matt was learning about promotions and making a career in the civil service. Since I moved in, he had managed two promotions, one with a substantial pay increase, hence his generosity when helping me build a wardrobe. This did mean he got to chose the dresses, not a problem usually, as long as we were not going out, but there were times I had to refuse to wear some things as being just too late 'night' for going out to the supermarket. I bought my first pair of trousers for over a year that summer, white linen and too long for the flat shoes I hoped to wear with them, but Matt approved of them and I later bought some skinny jeans and shiny black legging. As long as I wore heels with them Matt did not seem to mind. This in a way was the beginning of my blurring the male and female styles I had, highlighted when I went to visit mum. Minimal make up, lip gloss and mascara, plain studs, my own hair brushed out to give volume, a loose white blouse, tight blue jeans and flat thong sandals. My aim was not to be gender specific but let the person looking make their own mind up, but I got called miss by the railway staff and mum called me Alexis when she saw me. So much for being neutral.
By the time our anniversary came round, it was clear that Matt was the career minded husband type, and I was the unambitious worker who found more pleasure in keeping a nice home. I had become the working 'wife'. We celebrated our anniversary by going out for a candlelight dinner. I for the first time wore a basque and let Matt see it just before we went out, so he knew how sexily I was dressed under the dress, so no one else but him knew. I made him pleasure me for ages by making him withdraw when he was close to coming, letting him calm down, then getting him back inside me from a different angle. It made for along but enjoyable night.
As you can tell, sex was still an important part of the relationship, but for me I had changed. Yes, at first it was about getting Matt to screw me, but after a year it was also about looking after him, and the clothes as well. I had come to love being feminine and looking like a woman. I still wore a shirt and tie for work, but I never wore male briefs or boxers under them. I never wore any big ear rings to work, but I rarely wore anything plain either. Nice pretty studs most of the time really. I bought a pair of very low heeled ankle boots to go under my trousers, maybe they looked like a male version but I knew they were not.
My hair was now a few inches longer, and Sally at the salon for the anniversary had styled and coloured it like this, my first proper girl cut which was meant to be nothing but female. I had done it to get away from the wig and to stop my own hair looking so untidy, but I was concerned about work when I went in on Monday, as I always was when I tried something different. I had not given it any volume deliberately, and made Marcus meet me outside and go in with me. He told me I looked fine, we did that gay hug thing and went in. To my amazement, the only thing that was said was about Marcus, and how long before he gets his hair styled. Seems we were the gay ones who egged each other on to be more outrageous than the other. There was no way Marcus would ever be seen in a dress. The men he liked wanted their boyfriend to be a boy, a pretty one, but most definitely a boy, they did not find girls attractive like I was to Matt.
So there you have it. How I went from male student to working wife in a year. Maybe one day I shall make the change more permanent with surgery and hormones, but for now I have a work uniform of white blouse, narrow tie and chino style trousers. Changing my name officially might come, but is not necessary. Matt and I know who I am and work seem to be ok with a very camp gay worker.
My name was Mike Grant, and I say was, because it's different now. I have
two years of college and I'm taking classes at night to finish with a degree in
Business. In order to support my school expenses and have some spending
money, I found a job working in an office as sort of a glorified office boy.
I'm 5' 7" tall with soft brown hair and blue eyes and I have never weighed
more than 140 in my entire life. Valerie Hooper, the woman I report to is in
charge of the office, and also prepares parties for Christmas and so on.
Valerie is about 50, married, with two sons and a husband. For Halloween
she wanted everyone to come to work in costume, fully expecting a lot of
monsters or ghosts. When I told her I wanted to do something different but
had no idea of what, or who, to come as, she smiled and told me that I could
easily come as Diane Benson, the actress, when she was my age! "You have
the same facial structure she does, and with the right makeup you could be
her twin Mike. Think about it and let me know. That night I told my mother
what Valerie had suggested, and to my surprise she agreed! "I can help you if
you like Mike. Your sister still has a lot of her clothes here so that would not
be a problem. Besides, it could be a lot of fun!" I told her that I would think
For years I was lonely, depressed, angry at myself, the world, and the gods
that made me this way. I knew I was smart and had a good job, but at age 20,
I was still driven by urges I never had any control over, no matter how hard I
tried. I often felt the urge to dress as a girl, but each time I did, and then
looked in the mirror, I saw a clown instead of the woman I wanted to be.
Including my makeup, I was merely a parody of the woman in my dreams.
My frustration at my inability to achieve any semblance of the woman I felt I
wanted to become had driven me into silent secrecy when I did try to dress
up. That night, in my robe, I munched snacks as the television played in a
muted tone. The young women on the screen were a constant reminder of
what I wanted to be able to look like, and equally, my inability to either
conquer my desires, or forget it, or become the woman I had so many dreams
about. In my heart I knew I was going to do it, because even though I had
secretly tried on my sister's clothes many times when I was growing up, and
always felt like a clown, this time I would have my mother to help me. My
mother's tacit approval lifted the veil of frustration and I felt as if I was
soaring. I knew, in my heart, that this time, I would look good. Since Claire
was just a year older than I was, most of her clothes fit me pretty well, and I
was sure that with some help, I could look pretty nice. My biggest concern
was how everyone in the office would react to me dressed as a girl. The next
morning, when I told mom about my concerns, she told me that in her mind,
the best way, if I was going to do it, would for me to be perfect. Since I
didn't want to come off as a clown or one of those freak of the week people,
I agreed. "I'll get a few things today and we can see how you do tomorrow.
If you like it then you can stay dressed as a girl until Monday."
Someone once said that tears are merely a reflection of the soul, whether its
fear, joy, or sadness. All those years of hiding, frustration, fear, and secrecy
came to a head all at once, and I started to cry. Why are you crying Michael?
This is what you want isn't it? To live and work as a female?" My head
popped up, and out came, "What!" "I'm sure its true Michael, based on the
number of times you wore Claire's clothes!" Shocked that mother knew
about my dressing up as a girl, and afraid of what I might blurt out, I kept my
mouth shut. "I said I would help you if you let me Michael, and I think that
you should practice dressing every day after work, and each weekend from
now until the day when you go to work." I started to say something, but
mom held her hand up and said, "You did say that you wanted to be perfect
didn't you?" "YesÉ" "Well this will give you a few weeks of practice before
the party!" I could find nothing more to say about it, swallowed my pride,
nodded my head yes, and quietly went to my room. That night I decided that
mom was right. I would do the best I could or not at all, and if she already
knew about me dressing up and wanted to help me then no matter how I
thought I looked it wouldn't matter.
On Saturday morning right after breakfast mom told me to go to my room. I
have everything you'll need. I'll just show you how to use it and you can
take it from there." As far as my mother was concerned it was a done deal,
and that combined with my natural desires made it easy for me to stay silent
in my agreement. Mom gave me the stuff, which I recognized as a popular
hair removal cream. As soon as she left the room I stripped and quickly had a
coat of the cream all over me, from the eyebrows down. After a shower and a
close shave I stepped out and patted myself dry. I had never yet shaved my
body or used hair removal cream before, and I was surprised at just how
smooth my skin felt. My beard, while not what you would call light, was a
light color and only moderate in growth, and after I shaved I had nice soft
skin. With the towel wrapped around me I went into Claire's bedroom and
closed the door, hesitating for just a moment because I was pretty sure that as
soon as I was dressed and stepped out of the room I was not going to want to
quit. Ignoring that thought I forged ahead, opened her dresser and selected a
pair of lavender colored cotton panties and slipped them on. When Claire was
younger she had a shape like a pencil and used a padded pantybrief and some
breastforms to give her some shape. I had found them while I was in her
room dressing once, and made sure I left them right where I found them. I
slipped on the pantybrief, adjusting the pads to suit me. The pantyhose went
on easily, but the nylon against my now naked skin was like an electric shock
as I slid them on. I went to the vanity and sat down facing the huge mirror.
Makeup was the only thing I had managed to almost master simply because
that was all I could do on so many occasions. I applied the foundation using a
powder to set it, brushing away the excess as soon as it dried, leaving my
skin looking soft and smooth. On my eyes I used a mint green with copper
and gray highlights with deep black eyeliner both over and under my eyes. A
bit of rose blusher on my cheekbones and black mascara on my lashes. My
naturally curly hair was thick, and as it was drying the ends started to curl, so
with a brush I was able to create a modest if messy pageboy that framed my
face. The curly ends added just the right touch to the style. I didn't even need
a curling iron. I heard mom knock on the door, and when she came in the
room and saw me, she told me that my makeup was fine. "Let me help you
with your nails." I opened the small drawer and pulled out the box of fake
nails. Using the glue in the box mom attached one to each of my nails and
filed them into an oval shape with rounded tips. The polish I selected was one
shade up from pink. It took a while for the polish to dry, and while I waited I
stood in front of the closet and tried to select what I was going to wear for my
first public debut.
As soon as my nails were dry I slipped my arms into the lavender bra and
settled it in front after I fastened the single front hook. The breastforms were
flesh colored, filled with silicone to a small 'B' cup, which was perfect on
my frame. The waist nipper was beige with eleven hooks and a zipper, and
once I had it on it made my waist a trim 25 inches. Unable to decide on what
to wear, mom picked out a light blue floral summer dress for me to wear. She
said it would 'go with' my bra and panties. I wore off white sandals and a
matching blue jacket. Mom redid my hair a bit and it seemed to flow around
my face. I looked in the mirror and was floored! The reflection in the mirror I
saw that I did look like Diane Benson in a way and I stood before the mirror
in a dream like state looking at the girl standing there. I loved the image I was
seeing. The girl that I had only dreamed of stood in front of me, not perfect
of course, but I did not feel like a clown this time. The image I saw in the
mirror burst all of the illusions I had about my maleness! Inside, in that
private place we all have, I knew that I would never again be happy again
unless I was able to become this young woman more than once in a while.
The girl, me, was looking back from the mirror, and like my sister, she is
stunning. Her large blue eyes with their long lashes look deeply into me. She
has wide, pouty lips highlighted by sensual reddish pink lipstick. Her soft
brown hair falls a few inches above her shoulders, styled with bangs, gently
brushed without a single hair out of place. White button earrings and a thin
white necklace merely enhance the simple blue dress. The simplicity of the
dress draws my eyes to my face. Without any fanfare at all I turned to face
my mother, and when she looked up I heard her gasp. "Damn!" Mom stood
up and had me turn around for her. "If I did not know it was you I never
would have guessed that there was a boy under that dress!" "Thank you
mother." I sat down facing her, my knees firmly locked together and my
hands in my lap. "I can see that you know how to do makeup and get
dressed, but how are you in public?" "I've never been out of the house
mother." "Then it's time that you experience things all women enjoyÉ like
shopping, having your nails done and your hair styled." "Like this!" "Of
course dear! How else?" "ButÉbutÉ" I started to sound like a car that
needed a tune up, but mother had made up her mind! "Michael, you and I
both know that you want to go out and make people think that you are really a
girl, don't we? Lets stop pretending that you are so attached to your macho
self and admit that you love being a girl." Why did she always know? Are all
mothers able to read their children's mind like this? Without waiting for an
answer she said, "Get a purse and put your wallet and some lipstick in it and
I'll get cleaned up a bit before we go."
As I waited for her to get ready I knew that mother was right. I no longer had
any reason to use excuses or delaying tactics. The time had come; I had to
step outside wearing women's clothes. I had to, and wanted to, act enough
like a real girl to convince everyone that would see me that I really was a girl.
I had to act in a way that everyone who saw me would believe I was a
female. The very thought of being a convincing girl made me feel weak and
vulnerable, yet fear was attacking every nerve in my body, and the longer I
waited the more my fear grew. Mother finally showed up, but before we left
the house she asked me what my girl name was. "I never picked one
mother!" "Then why don't we use the name of the actress you look so much
like?" I agreed, and from that moment on she called me Diane.
The first thing that I became aware of was how the breezy air felt on my
nylon covered legs. That same slight breeze also kept teasing its way up and
under the hem of my dress. It was a new sensation, but I have to admit that I
loved it. I found that wearing high heels made my hips sway, and I had to
walk with a better posture just to help me to maintain my balance. It wasn't
long before I began to hold my arms up at my sides bent at the elbow instead
of putting them in my pockets like I normally did. Mother saw the way I was
reacting to the clothes, but instead of saying anything she just smiled at me
warmly, with approval written on her face. I wondered about that, and finally
I asked her about it as we drove to the mall.
"You would have done this sooner or later anyway Diane. If I help guide you
then you'll have an easier time of it and I get to have another daughter who is
a lady to her core." She glanced at me and saw the worry on my face. "Diane,
you are a boy, that's true. But only on the outside I think. Inside, where it
counts the most I think you're a girl. That wasn't clear to me until I saw you
for the first time this morning, then it was obvious, to both of us I think. Am
I right?" It was my moment of truth, and without even thinking about it I
nodded my head yes. "I don't think that you feel you're much different from
any other girl at this moment Diane. I know that you want people to think
you're a girl, and you want them to treat you like a girl, so we'll have to
make them think you're a girl, won't we?" Again, I nodded my head yes, but
this time I knew I had a smile on my face. "You'll need panties and bras of
your own Diane, so why don't we start there." It was a statement of course.
We both knew I would do whatever she wanted.
I walked right beside my mother, keeping step with her, noticing how she
held her hands and like her shadow, I began doing the same things. In the
lingerie department we bought a dozen panties and three new bras before we
moved to the junior department where I tried on several skirts and dresses
which we bought along with two suits. In the shoe department I tried on
shoes and found that Claire and I wore the same size, so I only bought a pair
of beige flats. "Let's put the packages in the car Diane, and then we can have
some lunch before your appointment at the salon." "My appointment?"
"While you were in trying on that nice pink suit I asked the girl to call ahead
and get you an appointment. You do want to look your best on Monday don't
you?" "But I thought I was going to do this on the weekends for three weeks
before I went to work as a girl!" Mom was pushing me to see how far I
would go, so in a fit of bravery, I one upped her to see what she would do.
"Of course! Maybe I'll get my hair colored and a nice perm at the same time."
"That's probably best if you're going to work as a woman. Maybe they can
pierce your ears at the same time." Mother was not about to be one upped by
me, and had even raised the stakes a bit higher. Unfortunately I had nothing
else to offer and my bravery made it firm. I could only smile in my
acceptance. I had walked up to the cliff and stepped right off so to speak.
After lunch we walked to the salon in the mall and a woman named Betty
took me to a chair. "This is Debbie, she'll be your stylist." I looked at her and
smiled. After some discussion about what I wanted, Debbie concluded that I
didn't have a clue, and she simply told me that she would do a 'modest'
amount of work on my hair before she started on me. I simply let her do her
work with a minimum of chatter. When I had to move to the dryer another
girl came over and started in on my nails, removing the ones I had put on that
morning then made them slightly longer and used a light red polish on them.
While she was doing my nails another girl pierced my ears and added small
gold hoops! When Debbie was done and I looked in the mirror I was stunned
at just how much a simple hairstyle can make a person change. My once soft
brown hair was now blond, done in soft waves on top that terminated in
sharp curls behind my head. My hair was just below my ears, brushed out to
frame my face with bangs that were swept to one side. In my ears sat small
gold hoops. I looked so different that it was hard not to keep looking in the
Mom and I drove home and at mom's urging I moved into Claire's bedroom.
I put the clothes away and started to move things from my old room to the
new one, moving some of Claire's things, like underwear, to my old room.
Later that night I went on line and found a site I had visited before. They sold
things to help make men look like women, even if they were naked. I had
visited this site many times in the past but had not yet bought anything. I saw
that they had improved everything, so I used the on line ordering system to
buy a few things I knew that I would need. I did not tell my mother. That
night we watched television, mom in her flannels, me in a nightgown and
robe set that was not much more than a diaphanous swirl of light blue
The next morning I got up, brushed my hair, did my makeup and dressed in a
skirt and blouse before I went to the kitchen and started the coffee. Mom
came in shortly, and as we had our breakfast, she asked me what I had in
mind for the day. "I have a few things I want to do on the computer, but I
would like a picture of me first." "I'll get the camera!" Mom snapped the
picture as I stood in front of a blank wall, handing it to me when it popped
out of the camera. I took the picture and in my room I scanned it into the
computer so I could clean it up a little. Then I scanned in my college ID,
drivers license, and work ID. With the software it was easy to cut my old
picture and paste the new one in its place. Changing the name was harder
because I had to match the font, which was different on all of the items.
When I was done, I printed out one of each on my printer, in full color, and
other than the picture and name, I had exact copies of each piece of my ID.
My name on each was Diane Michelle Grant. My dad had used a laminating
machine quite often, and it was still in his office, so I went in and laminated
I was so elated at being able to dress as a woman that almost could not stand
it. I fixed up a wallet that I had found in Claire's room with all of my new ID,
moved my pictures, credit cards, and money to the new wallet and put it in
the purse. My image in the mirror kept my attention, which was narcissistic I
suppose, but I loved the way I looked and did not want to give up being a girl
any sooner than I had to. At three that afternoon the things I had ordered
arrived. Their ad was correct! Next day delivery! Mom signed for them, and
as soon as I saw her she gave them to me. "What is this?" "I'll show you in a
little while mother. Right now I have to examine them to make sure
everything arrived undamaged."
Of course nothing was damaged. It's hard to damage latex just by shipping it.
I eagerly opened the package, and right on top was the panty with the
artificial vagina. I set it aside and pulled out the box containing the
breastforms. Each of the breasts was made so real looking that it was scary! I
eagerly stripped my blouse and bra off, read the instruction sheet carefully,
and using the enclosed adhesive, attached them to my chest. As soon as I
smoothed out the seams they seemed to become one with me as only the
almost invisible seam remained. The vaginal panty was harder to put on, but
again, following the instruction sheet, I managed to slip it on, removing all
traces of my manhood. Naked, I looked in the mirror and saw a young girl
from head to toe. In my reverie I failed to hear the door open; when my
mother gasped I turned to see her ashen face.
Without a word she walked up to me and touched the breastforms, assuring
herself they were fake I guess. She knew for a fact the vagina was a fake. "I
see that you have become a girl after all! Do you have to take that off toÉ"
"No mother, but I have to sit just like any other female." "Well, since you're
so much a girl now why don't we go out tonight?" Without waiting for an
answer she told me to wear the same blue dress and walked out of the room.
After shopping, and a trip to the salon I knew that I was not a clown at all. I
was now able to present myself as a female and make people believe it, but
mom had posed a challenge of a sort, so smiling I went into the bath and after
washing the old makeup off, I shaved as close as possible.
I was not yet able to make myself over into the various 'types' girls, but I
knew what I wanted to look like. I wanted silky soft skin, full, sexy lips
framing a radiant smile, a gorgeous outfit, and perfect hair. I did not want to
be a girl with a sweet childlike look, but instead I wanted to look pretty, like
the proverbial girl next door grown up into a sexy woman. I went to the
dresser and pulled out a corsolet and tossed it on the bed, then added black
panties to the pile. I was going to wear black, not the same dress I wore
earlier in the day. I found one I liked better. This one was also a sheath dress,
but it had a plunging back with a low cut front and was a very hot mini dress.
I had seen Claire wear it exactly once, for a dance she had gone to, and
spectacular does not describe how she looked in it. I hoped I would look half
Sitting at the vanity I did my makeup, and with the new cut, my hair seemed
to fall in place with a minimum of fuss. I no longer needed the padded
pantybrief and slipped the black panties on. The corsolet was a lot harder to
get on than I imagined. It had eleven hooks up the front with a zipper over
that, and laces up the back. I was unable to tighten the laces on my own so
mom came in and did it for me. Once I was all cinched in, my 'breasts' sat in
the cups, the nipples barely held in. I pulled on the pantyhose and reached for
The dress had a single strap that went around the back of my neck attached to
the sweetheart neckline, fitted bodice and hip hugging skirt. I slipped it over
my head and mom zipped it up for me. The hem of the dress was a good
three inches above my knees while the bodice defined my now trim waist and
my breasts were clearly displayed. Smiling I went to the jewelry box as mom
left for her room. I found the black and gold chandelier earrings and attached
them, then fastened the matching choker style necklace around my neck. On
my left wrist I wore a thin gold bracelet, which was all the jewelry I wore that
night. I did my lips in a deep red and spritzed myself with perfume. Looking
in the mirror I knew without a doubt that this is what I wanted. I could not
simply give her up now that I had been allowed to find her, and I made up
my mind right then. Diane was going to stay no matter what.
Mom said nothing when she saw me, but I saw her smiling as she turned to
get her purse, and I knew I had made a good impression on her. Dinner was
at a new place by the river, and as we dined mom and I talked about the
transformation that had come over me in just a few days. It was my turn to
tell her the truth. "Mom, I've always felt this way, I just never had the chance
or the nerve to tell you about it. When Valerie suggested it I was afraid to tell
you. When I did, I was sure that you would be angry at me. But now I know
that I have to dress this way, all of the time, even at work. I have to become
Diane all of the time or I think I will bust!" Mom reached out and took my
hand in hers, and told me she knew that the first time she saw me. "If that's
what you want, then I'll support you of course, but you have a lot of catching
up to do if you want to be a real lady. Starting now, I'll teach you all you
have to know to become a woman."
I spent all day Sunday getting ready for my debut at work, which made mom
just shake her head. "You don't have to do anything special Diane, you look
very nice right now!" But my concern manifested itself in an obsession to be
better than just okay. I used the hair cream again then shaved every inch of
my body that I could reach until my skin was as silky smooth as any woman.
I washed and cleaned the vaginal panty and breastforms before I put them
back on. This time, rather than rely on pressure to hold the panty in place, I
used glue to secure the seams in the crack of my butt. The breastforms were
pert with no sag, and made me feel very feminine once I had them secured to
my chest. Somehow they felt natural, like I should have had them all along,
and I could not, or did not, want to visualize myself without them. Mom had
given me an aloe based skin lotion, which I rubbed in all over, making my
skin softer to the touch and smelling of flowers. I slipped on some panties
and a bra then some shorts and a tee top and began to select my wardrobe for
the next day.
In my heart I knew that the only thing I was going to wear was the new pink
suit mom and I had bought on my very first outing as a girl. It had a straight
skirt that was above the knee a little, and a fitted jacket with no lapels. Both
were lined, which meant that I didn't need to wear a slip with it. For a blouse
I selected a thin gray pullover blouse that had a single button at the neck, in
the back. The blouse was mom's but because of the vagaries of women's
sizes it fit me perfectly, and I wore a size 12 to her 10. Claire had a pair of
gray shoes that I borrowed, size 8 by the way, and in my mothers jewelry
box I found pearl earrings and necklace set. I already had a gold watch and
two rings. Once I had everything ready, I relaxed and made a late lunch.
With the vaginal panty it looked as if I had rounded hips and a natural taper in
the front, just like all women did. Mom even commented on it once. "You
might want to call Valerie and tell her how you'll be dressed in the morning
Diane. I'm sure she won't mind, and at least she'll be prepared when she
sees just how pretty you are." That made sense, and right after lunch I called
Val and told her that I would be dressed as a woman when I showed up for
work. Her only comment was that she would look forward to it!
I spent the night in curlers, getting up early to do my hair and makeup. As I
slipped the panties on and saw the cleft in the front a feeling of calmness
came over me and I relaxed and got dressed. A soft, lace trimmed demicup
bra in white, nude pantyhose, and a white waist nipper. I pulled the skirt on,
then the blouse, stepped into the shoes and pushed the earrings into the small
holes in my ears. I pulled the jacket on and used a soft reddish pink lipstick to
outline my mouth, added perfume, the necklace, watch, rings, and bracelet.
Looking in the mirror I could see no trace of the man I was just a few days
ago. Once unleashed, Diane had taken over and consumed me, and now, I
was Diane Michelle Grant, inside and out. My purse was filled with my
wallet, lipstick, tissue, and car keys. Drawing in a breath I left the house for
the biggest event in my life. Whatever happened today, a spectacular success
or a colossal flop, everyone would know that I wanted to dress and work as a
woman, and there would be no going back. Strangely, the fear that had
consumed me before did not cross my mind as I drove into the parking lot.
I locked the car and walked to the door, showed Walter, the guard my phony
ID and walked in. It was no longer a maybe, and I walked into the office and
straight to my desk, and the first thing I saw was the nameplate. 'Diane M.
Grant' etched in white on a blue background sitting on my desk! I stashed my
purse in my desk and went to get a coffee, returning just as Valerie walked
in. She took one look at me and broke out in a huge smile. "I was right! You
look spectacular Diane!" She went to get a coffee, returning to my desk
quickly. "I'll introduce you around today Diane. The way you look, nobody
will believe it if we told them who you really are, so I'll let them assume you
are a new hire and we can go from thereÉ okay?" It really was the best way,
so I agreed.
As I was introduced around the office I saw a lot of different looks that I had
never seen before. From the men it was mostly an evaluating look and each
time I felt as if I had been mentally stripped. From the women it ran from
indifference, (from the pretty ones), to envy (from the older ladies). Valerie
motioned me to join her in her office, and as soon as I was seated she asked
me for my ID. I gave her the one I had made up, and after a quick look made
arrangements for me to have a new one made. "You'll have the same duties
Diane and the same rate of pay of course." Then she explained the looks I got
from everyone. "All men are on the make all of the time Diane, and to them,
you're fresh meat so to speak. Ignore them and they'll relax after a few days.
The older women are jealous of the way you look while some of the younger
girls see you as competition. You can ignore them as well, or play it as you
see it." Then she had me go and have my picture taken for my ID card,
assigned a new computer sign on, and I went back to work, doing the same
exact job as before.
During the morning I settled in and finally relaxed as I discovered that
everyone accepted me for what I appeared to be; a woman, about 20 years old
or so. At lunch Kelly and Beth asked me to join them, and we sat together at
one table. I got an earful as they discussed the single men that worked in the
office, in graphic terms, and some of the older women who they thought
were ready for the retirement farm. It was a very educational lunch!
For my part I paid close attention to what the other girls wore and so on. My
new ID card arrived at two, just as I had my first phone call. In person mom
and Valerie both told me that I looked like the actress I had taken my name
from, but I sounded like Kathleen Turner. On the phone I had no idea how I
would sound, so I was relieved when the male caller addressed me as a
woman. That night I collapsed on the couch from the stress mom said. After
that it got easier each day, and at the end of a month it was as if I was a
natural born female. I hated shaving close every day because my face became
sore and very tender. That's when I saw an ad in the paper, showed mom,
and she agreed. I made an appointment by phone, and that Saturday morning
at eight I was at the clinic.
I was shown in to see the doctor, and was surprised to see it was a woman. I
had to tell her my true status of course, which was hard because by now I did
not look like a male in any way. She sat there quietly while I told her all about
myself and the dilemma I found myself in. When I was done I fully expected
her to toss me out, but all she did was ask me some medical questions, my
medical history and so on. Then she asked me if I would like to have my own
breasts! "Of course, but I'm not taking any hormones, so that seems out of
the question right now." "Maybe not Diane." When she told me how she
could do it, that day, I was all smiles and agreed to it right then.
I was out for the entire procedure, but essentially, she used a laser to remove
my entire beard, then Liposuction to draw fat from my waist and used it to
make breasts, the same size as my fake ones. When I awoke I was sore, but
not bad, and I had a few small stitches. But I also had a 23 inch waist and
two perfectly formed, completely natural breasts. I was in heaven as I got
dressed and then drove home. Mom knew I was going to have my beard
removed, and when she saw my slightly swollen face she started clucking
like a mother hen and immediately wanted me in bed. I was just too sore to
argue with her and let her help me get undressed. When I removed my bra
and she saw me, a common occurrence in our house, she saw my brand new
boobs and narrow waist for the first time. "Those are real!" "Yes, they are!
Aren't they nice?" Then I explained how the doctor did it. Mom helped me
get a nightgown on and I went to bed, staying there until late the next
morning. In the shower I felt my new breasts, washed the stitches in my
navel carefully and wearing just panties I slipped on a top and a skirt, which
fit a lot better now that I had a smaller waist.
During the next week I became used to having sensation in my breasts, and
loved every minute of it. On Friday Valerie invited Kelly and I to her home
for a barbecue on Saturday afternoon. She failed to mention that both of her
sons would be there. I picked out a tan floral summer dress, and wore tan
sandals with a thin, short sleeved jacket. My hair, now trimmed, flowed
around my face like a halo. I had a small brown leather purse to complete the
outfit. I examined myself in the mirror. My hair was longer now, cut and
styled in a more business like way, but still casual. My shoulders, accented
by the short sleeves of the jacket, were trimmed with brown piping. The top
of the dress did not have a deep neckline, but it was low enough to allow a
hint of my cleavage, and that was accented by delicate gold locket suspended
from my neck. I wore a minimum of makeup, just a hint of eyeshadow, a
soft red lipstick and my best perfume.
As soon as I arrived at Valerie's her youngest son, Mike greeted me and
showed me to the patio. Unlike Valerie, who was my size, Mike was huge!
He stood at least 6'3" tall! I had to look up to see his face! Kelly was already
there, sitting with Douglas, Valerie's other son. He was also quite tall. Both
of her sons had dark hair, Mike with green eyes and Douglas with blue. Her
husband was not as tall as his sons, but he had the same build. He was wide,
with a barrel chest, and dark hair. It was immediately obvious that Valerie
had arranged this little party so Kelly and I could meet her sons! While I had
been living and working as a woman for almost four months now, I had
never had a date nor had I ever looked at a man like a woman would. I had
known that sooner or later some man would hit on me, and now, it seemed,
was the time. Mike almost, but not quite, doted on me, and I often saw his
gaze drift to the top of my dress; I knew he was not admiring the material my
dress was made of!
When I looked up at him I could see that atypical look of male superiority on
his face. I felt so feminine right then, and it was a wonderful new feeling. I
now knew what my mother had told me about men was true. They had a
magnetic appeal to women that simply could not be denied. I knew that there
could be a lot of joy to be had in being so attractive to a man, and the thought
of being Mike's new girl friend ran through my mind. I was flattered that he
thought I was pretty enough to make him come to me, yet in the back of my
mind I wondered why I felt this way. Until I had started to dress as a woman
I had never had a sexual thought about another male in my entire life! Now I
was thinking about Mike in ways I had never dreamed of before. We sat at
the table side by side eating, and even though I held up my end of the
discussion, I was thinking about the way Mike had looked at me.
Thinking of Mike, as my boy friend did not turn me off at all, instead it had
just the opposite effect. I was a girl and I had a real live male catering to me,
like a boy friend would. Not only that, but I was flirting with him the way
girls do to their guys. I began to feel hot inside as my thoughts drifted to
more erotic places. That scared me momentarily, because up to that moment I
had never had an erotic thought about a maleÉ ever! As our food was eaten
and just the drinks were left, I felt his hand on my leg half way up on my
thigh! Right then Valerie started to clear the table and Kelly and I jumped up
to help her. It saved me from making a decision whether to let his hand stay
there or ask him to remove it.
"My sons seem to be taken with you girls." That was obvious, but it was
Kelly who stated it. "Like you didn't arrange this Valerie! I'm certainly not
complaining mind you, Douglas is very nice." They both looked at me, and
all I could do was smile. Nobody said anything else, and we filled several
pitchers and rejoined the men. Mike asked me to take a walk with him, and
took my hand in his as we walked along the waters edge. We rounded the
point and as soon as we were out of sight he spun me around, held me close,
and kissed me. He was gentle but urgent as his tongue probed against my
mouth and I opened so his tongue could enter me. I was unable to pull away,
not because he was so big, but because I didn't want to. He asked me out for
the next night, and I agreed. By the time I got home I had become like a
young girl in my anticipation of this date. I know mom saw it, and when I
told her about it all she did was remind me what good girls did, and did not
do. Big help she was!
I had chosen to wear a skirt that flared slightly at the hips with square cut
pleats in a dark green. A simple white blouse, and black two inch heels. I
added jewelry and perfume. My makeup was for evening, darker eyeshadow
and a dark red lipstick this time. I was nervous as I waited for him to arrive,
but when he did I calmed right down. He took me to dinner, and later, he
drove to a secluded spot by the lake. As soon as he kissed me all of my
mothers admonitions went out the window, especially when his hand found
my breast. Every nerve ending was on edge as he manipulated me like a
musical instrument, making my body play his tune. When he took my hand
and placed it on his member I felt myself shudder, not in revulsion, but in
lust. I wanted this man to take me, love me, make me love him back, and he
did. Unbidden my hand began to stroke him and I felt the buttons of my
blouse come undone and his hand found my naked breast while I unzipped
He popped out all engorged and hard, throbbing in lust as my hand again
found him. The skin was like velvet, yet hard like iron beneath my hand. I
was stroking him when all at once he gushed, filling my hand with goo.
"Sorry about that Diane." He gave me a hanky and I cleaned up. "This isn't
the place for two people our age Diane, why don't we go back to my
apartment?" Common sense kicked in and I asked him to take me home, and
like a gentleman he did.
Mike called me every day at work and each night at home. Valerie told me he
was so in love he could hardly stand it. Kelly asked me if I had slept with
him yet, and when I did not give her an answer she assumed that I had. On
Friday night Mike and I had a date, and I knew in my heart that I was going
to have sex with him, so I packed a small bag to take along. Mom could
hardly miss it, but this time all she told me was to be careful. "That vaginal
panty is very good Diane but this can lead to disaster if your not very
careful." "I'll be careful mom, but this is the last hurtle isn't it? I have to do
this even if he finds out." Later it turned out I was right, because right after
dinner he drove us to his place. As soon as he had closed the door he was all
over me, and I once again became like warm bread in his hands as he
massaged my nipples with his fingers. I felt the zipper of the dress going
down, and when it did I stepped out of it and tossed it aside. Mike watched
as I removed my bra and tossed it aside as well. I reached out and began to
unbutton his shirt, then his pants. He stepped out of his pants and just stood
there. I ripped his briefs down in a single motion leaving him naked in front
I sat on his couch and removed my pantyhose and shoes, leaving my panties
on as he grabbed my hand and took me to his bed. He found every single
spot that turned me on and some I didn't know I had. I wanted him to be
mine and pushed him on his back. His erection stood tall and proud as I went
to my knees, bent over, and kissed his member. It was not unpleasant, and
when my mouth opened I took all I could in a single motion. His hands held
my head as I bobbed up and down, until I felt him starting to tense up. I
straddled him, and helped him find the opening in the vaginal panty. He slid
in and I began to rock back and forth, watching his face the whole time. His
eyes closed and he was moving his head, but his hands remained firmly on
my breasts as I pumped him. I was now in charge of this man and I loved it!
Finally he released and filled my panty. Spent, he fell back as I went to the
bath to clean up. He was still naked in the bed when I returned, also naked as
his hand reached out and pulled me to him. I lay next to him, my hand on his
manhood while he kissed my breasts, renewing my excitement.
He grew hard once again and once again my mouth found him. This time I
wanted to taste him, and did not move as he swelled and released his seed
into me. I spent the night with his arm around me firmly cupping a breast
with his hand. I woke before he did, dressed in the skirt and blouse I had
brought along, brushed my hair into a ponytail, and started the coffee. It was
a very domestic scene for sure as he woke up and saw me. Naked, he went in
and took a shower, returning in shorts and a tee.
I put both of my hands on the cheeks of his butt, and tried to keep him from
moving to far away. I wasn't surprised to find that he was rock hard once
again. I genuinely hoped it would not be too long before he wanted to take
me out on a date. Then Mike kissed me again. "Eat your breakfast Michael,
you'll need your strength for later." I know it was coquettish of me to tease
him, but I simply could not resist. After breakfast he helped me wash the
dishes, and then his hands found my breasts again.
He had the stamina of a bull and it was another two hours before he took me
home. Valerie was there talking to mother when he dropped me off. "By the
look on your face I would say that Mike is a very happy man this morning!"
"A polite woman never talks about her conquests Valerie, even if it is the
bosses son!" "He's going to ask you to marry him Diane, probably this
week." "Diane, I think it's time that you told him about yourself, and made
arrangements to make yourself into a woman, don't you?" Mom was right,
Mike deserved more than a lie. "Okay mom, but maybe you and Valerie could
be here when I tell him." They looked at each other and nodded their heads
yes. "We'll be by tomorrow Diane, around six." The next day was hell as I
wondered how I would tell Mike about myself, and Valerie was no help
either. All she said was that Mike and I would have to find a way to
overcome this minor obstacle.
After dinner mom and I did the dishes and I sat, waiting for Mike and Valerie
to arrive. Promptly at six the doorbell rang and I admitted them into the
house. "Mom says that you have something serious to tell me Diane, what is
it? Valerie and mother had mysteriously disappeared, leaving me alone with
Mike. Direct is usually the best approach, so I drew in a breath and told him.
"Mike, I'm not a female, but I love you and want to be your girl, and
hopefully, your wife." "What do you mean your not a girl? You and I slept
together, and I think I would know a girl when I saw one, especially when
she is naked!" "I'm sure that's true Mike, but none the less, I am not a
female. I will be shortly, but not now, right this minute. I wear a special kind
of panty that lets me have the look and feel of a woman Mike. These are my
boobs of course, but the rest is all latex." By the look on his face I was sure
he was going to hurt me and started to back up. "I'm angry that you weren't
honest right up front Diane! You tricked me, and that is wrong!" "Yes I
tricked you Michael! What would you have said if I told you, "hey fool, I'm
a man just like you!" You would have dropped me like a hot rock and you
know it! But it wasn't deceit on my part so much as my desire to be your
woman, or your lusting after me, panting every time you looked at me. No
Michael, this goes both ways. I love you, I really do, and I will make you a
fine wife if you let me. I just need time toÉ become that woman you want
me to be!" By then I had tears running down my cheeks and ran out of the
room straight into my mother's arms.
"He hates me mother!" My tears ran down my cheeks because I was ashamed
of what I had done. I was not a woman, I was a pile of latex trying to be
what I was not. I tried to tear myself away but I felt Mike's hand on my arm
and in a rush of emotion I fell into his arms. "Oh Michael, what are we going
to do?" he said nothing as he picked me up like I was a feather, and carried
me to my room, slamming the door behind us. "We," he said very forcefully,
"are going to make love again and then we are going to talk about thisÉ
problem we have." Then he unbuttoned my blouse and began to undress me.
I stood very still as he slowly ran his hands all over me, making me tremble
in delight and lust. Then he stood there as I undressed him, ran my hands all
over him until I reached his manhood when I began to stroke him. As he
purred I slipped into bed and lay there, naked and smiling. He took me
quickly but forcefully, and then later, slower and with a methodically slow
tempo which drove me crazy. Unable to quiet his lust, I rolled over, got on
my knees, put my head down and allowed him to take me. We were both
panting when he completed and lay there for a moment. Then I got a warm
washrag and cleaned him up so that I could use my talented tongue once
again. He stayed in my room that night and we talked about the future. I told
him how it all began and why, and in the end he asked me to marry him.
"You have a year Diane, after that we get married!" The he went back to
being forceful again, but I said yes and that night I slept like a baby.
Less than a year later I was a woman, and on our wedding night he found out
just how much of a woman he had married.
OK, let's get this part over with so we can get on with the story. I am a
fifteen year old boy, named Ron, I have a nineteen year old sister named
Carol and, as in a great deal of these stories, we have an absentee
Unlike in most of these stories, I am not a skinny, undersized wimp; as a
matter of fact I am quite large for my age, as large as my sister, I know
this because I spend a lot of time in her clothes unbeknownst to her and
my mother, in other words...I am a closet cross dresser.
My mother and Carol both work together in a nationwide firm, so now that
summer is nearly here and I will be home alone a lot, I will be wearing
Carol's clothes for several hours a day instead of the few hours a week
like I usually do.
It was a month or so before summer vacation that Carol got a new
boyfriend named Fred; he was twenty one and was in the money, his family
owned a lot of property in California. Except for cross dressing and one
other weird thing which I should be ashamed of, but am not, I considered
myself quite normal. I will assume that you want to know that quirk so
here it goes...for over a year now, before getting dressed in the morning...I
would go to the bathroom where Carol and I put our dirty clothes in the
hamper and take out the panties she wore the day before and put them on
under my undershorts, the worse condition they were in, the better I
liked them, especially after she was on a hot date and they would have
stiff spots on them, and when she was having her period and they were
really stained, I just loved that, but I digress, and I do that a lot,
The first time I saw Fred I almost died, he was the hottest thing I ever
laid my eyes on, and he was about six foot two and all muscle. Now I had
always thought I was a normal, straight guy but when I saw him, I wanted
him; I think I was even a bit jealous of Carol for a second or two. When
we shook hands I felt so weird and I think I saw something in his eyes
that told me he liked me.
Let's cut to the chase here...every time he came to pick up my sister on
Saturday night, I wished it was me he was picking up, and in bed at night
I would pleasure myself, picturing me dressed in the dress Carol wore
that night, and in the arms of this Adonis. I was constantly fighting
these thoughts because I knew I was not queer, as a matter of fact I had
beaten the shit out of a few guys I thought were.
Every Saturday I went through the same hell, and when he would come over
for Sunday dinner it was hell seeing him and Carol together.
I kept cross dressing after school but these times I pretended I was
Carol and was dressing for my guy. I was on an early release program at
school two days a week because I had a job, but quit and did not report
it, so I still left early and I had a few more hours to dress and be
"Carol" and pretend I was getting ready for my guy to pick me up.
One day a short while before school vacation started I was walking home
to get into the dress Carol had worn on her last date with Fred and who
do you think was passing in his car...? Fred. He asked if I needed a ride
home and of course I climbed in next to him and immediately got a hard
on. I invited him in for a soda.
We had a drink and while sitting at the kitchen table he kept touching my
hands and wrists, I read nothing into this but when I showed him to the
door after our drinks, he put his arm around my waist; I read nothing in
this either but after a few times, where he always seemed to "Meet" me
after school, I started to think he was actually hitting in me. Wow!
So...after a few times when I walked him to the door, he bent over and
kissed me goodbye, I dam near fainted and I did get a hard on.
This meeting became a regular thing at least two times a week when I was
on early let out. By then I knew we were lovers because after out sodas
we would sit on the couch watching TV or a DVD and snuggle, like lovers.
I would get very jealous when he would pick Carol up for their regular
Saturday dates. There were even times when I considered him cheating on
me with my sister.
Now...school was over and I knew we, Fred and me, would be seeing a lot
more of each other, the only sad part now was that I was no longer able
to cross dress as much. The only time I now had was after Fred left, and
when I came home from school before mom and Carol came home from work.
By this time there was no doubt that Fred and I were lovers, but of
course, he and were the only ones who knew it. The only problem I had was
that spending so much time with him was cutting down tremendously on my
dressing up time, so I thought; why not kill two birds with one stone?
Why can't I dress up and still be with the man I loved so much?
I never brought it up, that I wore my sister's clothes and had no idea
how he would take it. I would give it a try and see if he liked me as a
girl, and if he didn't, I would not do it again, at least not in front of
him. As soon as mom and Carol left for work I started looking for what I
was going to wear when Fred came for lunch.
I had seen Carol in this one dress and had never gotten the chance to
wear it so this would be as good a time as any. I got out the usual
undies and my own padding and put them on then pulled on the outfit I was
going to wear. I had Carol's panties on and was thrilled with them
because she was in the middle of her period and they were stiff with
dried blood and other fluids. It didn't take long for me to get into the
petticoat that she wore under the below the knee pheasant skirt with the
three rows of ruffles and elastic waist, the top she, and I, wore with it
was a short sleeved white shirt with a high collar. I wore a wide leather
belt to pull my waist in and give me a slimmer waist, the fullness of the
petticoat and skirt gave me hips. I wore pantyhose and on my feet, black
two inch high pumps. I did my make up as I usually did, light with just a
bit of eye makeup. I broke out my auburn wig which came to just below my
I did a lot of pacing back and forth in my room waiting for the sound of
Fred's car on the gravel driveway.
I heard his car, and just to be sure, looked out the window and saw him
I raced to the living room just in time to meet him as he entered the
door. He took one look at me as I stood there.
"Carol, but I thought...wait...Ron?"
"Yes, it's me, how do I look?" I said and posed for him nervously, hoping
he will like me in a dress.
"Fabulous, you are even prettier than your sister. What is this all
He crossed the room and took me in his big strong arms and kissed me.
I told him all about my dressing in Carol's clothes but left out my
fetish about wearing her soiled panties; that may be a bit too much. I
was so happy that he still loved me. Now that I was accepted as a girl I
felt that I could refer to him as my boyfriend, my man, and will.
He brought lunch, as usual and, as usual, we had it at the kitchen table,
and then went to watch TV before he had to leave.
"Tomorrow, my sweet, we are going out for lunch so wear something sexy."
I told him that I had school tomorrow so we could not meet again until
Thursday. OK then, Thursday, He said as he walked out the door. I watched
him pull away and blew him a kiss.
I assumed that he wanted to take me out wearing a dress. I had never been
out of the house as a girl but did not let it bother me; I knew that my
boyfriend, my man, would never put me in a position that would cause me
I changed back to my own clothes and spent the time before mom and Carol
came home looking through Carol's things picking out what to wear on my
first date with my man, wow!
I found just the dress; it was the one Carol wore last Saturday when Fred
took her out.
It was a long two days before I saw my man again, and it was the longest
two days ever. Fred would love me in the dress because he kept telling
Carol how great she looked in it.
I started getting ready as soon as mom and Carol left for work; I wanted
everything to be as perfect as could be. By the time my man came to pick
me up I was ready and a bit nervous, I believe I mentioned that I had
never been outside the house before, and this was also my first real date
with my boyfriend.
My dress was a sort of bone in color with tiny pink flowers all over it,
it has short puffy sleeves and a crew neck, the bodice was snug all the
way to my hips where it loosened up to three rows of ruffles to above my
knees; my shoes were white and had 3 inch heels.
When my man finally got there I thought his eyes were going to pop right
out of his head. He was satisfied with what he saw, I could tell this by
We went to a restaurant across town, then for a nice drive, getting home
with an hour to spare before the terrible two came home from work.
This went on for the entire summer, Fred and I spending all week days
together; the only thing that spoiled it was the fact that I had to share
him with Carol on Saturday nights and some Sundays.
Once in July I think it was, Carol came home all upset because she lost
her pocket book (Purse) with all her identity papers. It took her several
weeks before she replaced them all, she never did find the purse. It is
too bad she never asked me if I knew where it was because then I would
have had to lie and say no. Fred gave it to me; he stole it from her just
so I could have some sort of I. D. if I ever needed it.
(FYI, all the time my man and I kept company he made me use her name so
that he would not make a mistake and call her by any name I used, isn't
my man brilliant)?
Summer went much too fast and before we knew it, it was almost over.
About two weeks before Labor Day mom and Carol told me that they were
going to spend Labor Day on a cruise they had won at work.
This was just about the most wonderful thing that could possible happen
to my man and me.
We, Fred and me, made our own plans for the same weekend.
He told me to pick out some clothes, enough for three or four days plus
something fancy for going out at night. He was taking me out for the same
I was thrilled beyond measure, just think, me spending the entire weekend
with my man and not having to get home before Carol and mom came home.
I spent the next two weeks picking out what I wanted; of course I did not
pick them out physically because they would be missed. I made a list to
refer to when the time came to really pack.
Gosh, what a long two weeks ever. I thought the time would never come but
it did. Mom and Carol were no sooner out of the driveway when I was up
and packing my bags, I wound up with four suit cases, an overnight bag
for things like night gowns and stuff and a makeup case, and three
garment bags containing evening gowns and accessories. Then I had to get
dressed, that was the hard part, I put aside three dresses to wear when
my man came to pick me up for our weekend before picking out one.
I had a lot to do before even getting dressed. First I had to put on
false fingernails and paint them. Then I got all my padding which was
important with the dresses I had picked out for my weekend with my man.
My lace bra had thin straps because my dress has thin spaghetti straps.
The dress was one of carols most expensive ones and I had never even seen
it in her but I knew it would fit me because I had tried it on when I was
picking my wardrobe for this weekend. My dress was a two piece affair,
the dress itself and a lace jacket, one of those real short jackets that
only goes over your shoulders. The dress was all lace, from the square
cut neck to the knee length hem; it had a snug waist that was assented by
a satin belt about four or five inches wide. I was just putting on my
jewelry when my man walked in.
"Wow! If only your sister could look that good, I'd have married her
months ago" he said as he took me in his arms and planted a big old lip
lock on me. I pointed to the luggage on the floor and told him to bring
it out to the car while I finished up.
Finishing up was something I have always wanted to do but never could; I
sprayed myself with Carol's perfume and put the bottle in my purse. I had
never used perfume before because I only usually dressed for a few hours
and the scent lasted for at least twenty four and it would linger on me
and be noticeable.
My sweetheart returned to my room to see if there was anything else. "And
to give you this," he said as he reached in his pocket and brought out a
small box, something told me I knew what was in the box, and I was right.
He opened it and I saw a ring set, an engagement ring and a wedding ring,
I was flabbergasted as he placed them on my finger. "OMG," I thought to
He told me that they belonged to his grandmother and if she ever saw how
beautiful I looked she would surely want me to have them. Now I knew I
was pretty, but would never call myself beautiful, but I wasn't about to
argue with him.
"But why give them to me?" I asked.
"Because this weekend we are going to be husband and wife." I thought I
was going to faint right there in his arms. He told me that he had
reserved the "Honeymoon suite" at the hotel.
Things were happening so fast, from my guy, my man, to my husband in one
This morning I was a fifteen year old boy and now, only a few hours
later, I am a married woman, go figure.
Finally we were driving to the hotel as Mr. and Mrs. Gleason. Arriving a
few hours later we were greeted at the entrance by the head Bellhop and
Parking Valet. The bell hop took our luggage and followed us to the desk
where we signed in and for the first time I was greeted as Mrs. Gleason
and I made sure that I signed in myself in as Carol Gleason.
The bell hop led us to our room, the honeymoon suite, he opened the door
and stepped aside so my husband and I could enter, my husband lifted me
off my feet into his arms and carried me across the thresh hold, just
like we were really husband and wife. The bell hop must have seen this a
million times because he simply took our bags into the bedroom. My
husband reached into his pocket for a tip, this must have been difficult
because he still had me in his arms. Final, he put me down.
Just like a man, he lay on the bed while I unpacked the bags, put the
things away and made sure the garment bags were hung up in the closet.
With this being our honeymoon I don't think I have to describe what
happened next, but I will say that we did not go as far as you might
think. Keep in mind that I am really fifteen and we are both guys. The
most we ever did was some heavy duty petting and grouping. I am glad that
he never tried to go too far because I made myself a promise, no matter
who, no matter when, no matter how, I was never going to take it in my
butt or mouth, I think that is disgusting.
My hubby and I went for a short walk on the boardwalk to pass sometime in
the afternoon. Then it was time for me to get ready for supper at a
supper club in the hotel.
I just couldn't wait to get dressed; I picked what I considered the most
perfect gown for a new wife to wear on her honeymoon. I am so glad my
sister is so meticulous with her clothes because she puts everything
together, I mean that when I opened the garment bag with the gown in it I
found everything that would go with it, from shoes to lingerie to
The gown was light blue made of some kind of soft, shiny material. It was
long, ankle length and loose from my hips to the hem, not wide and
flowing, just loose; it had spaghetti straps and the neckline was very
low cut, enough to show half my silicone filled breasts. Also inside the
bag was a fur stole, silver fox which was just so soft on my bare
shoulders. My shoes were silver cross strap high heels that, at least for
the first few minutes were difficult to walk in. she had a small pouch
pinned to the inside of the garment bag in which she kept the jewelry
which she usually wore with this gown, I later realized that she did the
same with most of her many gowns.
The dinner was excellent; the show was very good, a comedian known for
his off color humor. There was one thing that surprised me just a bit, my
husband ordered drinks for both of us, I thought that I would be asked
for ID but they didn't, I guess I looked old enough; it was a bit
disappointing because I wanted to show Carol's ID that I had been
carrying around most of the summer.
Do you remember earlier I told you that if my husband and I were going to
have sex I didn't know what I was going to do because of my hang up?
Well, in our room that night I got ready for bed wearing a sheer, long
and almost see through night gown, I lay next to my husband wrapped in
his arms when he told me that he had no such compulsions, he loved taking
it in the rear and mouth. So...we consummated our wedding night with him,
more or less, playing the blushing bride.
We had breakfast on our private veranda and my hubby ordered a picnic
basket for later that day.
Like yesterday, we went for another walk and bought a few souvenirs.
We changed for the picnic, my guy in a pair of white shorts and a muscle
tee shirt, nothing so simple for this wife.
When I picked out what I was going to wear on this weekend going on a
picnic never entered my mind but I did choose something that just oozed
It was a full red skirt with all kinds of white flowers; it had a five or
six inch ruffle at the hem and a bit of white peeking from under the hem.
My top was a see through white shirt that I had to wear a long line bra
with; the sleeves were elbow length and puffed. I wore a wide red belt
and a white, actually ecru, wide brimmed hat.
We picked up the picnic basket, the desk clerk directed us to a nice
secluded spot for the picnic.
Lunch was good, we spread out our blanket on the grass and had lunch;
what I enjoyed most was the way my wide skirt spread out on the blanket
so it almost formed a circle around me.
Our second night there we decided to go to another night club. There were
several to choose from, that was no problem. As with last night
everything I needed was in the bag with my gown.
This time it was a white gown with green trim, the straps were a bit
wider than last night and flowed to a V neck but not so deep, the bottom,
from the waist down, had some stiff, but soft material pushing it out
away from my legs. There was a whit fur jacket that only went to my waist
and, I don't know if it was the style or not but the front did not meet,
it did not close all the way, but looked good.
As with the other night, the food was wonderful, the show this night was
a musical comedy with a lot of double meanings in it. We did not get back
to our room until way after midnight. We were going to be leaving
tomorrow so we went to bed right away.
After breakfast we packed everything back in the bags and suitcases and
garment bags, everything that is, except what I was going to wear back
home; check out was eleven so I was ready by ten.
My traveling dress was, like most of my dresses, wide skirted. This one
was white with long sleeves of lace, it had a high neck and tight bodice
and as usual the waist flared out to a full circle. The stiff petticoat
under my skirt helped push out my skirt, I needed my husband's help
zipping up because it had a full zipper from the waist to the back of my
neck; I have never been able to handle these long ass zippers.
No fur this time but I did use a Chantilly lace shawl.
Arriving at my house was a bit sad because I knew this weekend was
finally over and in a few days school would be starting so Fred and I
would probably not be seeing each other. Fred told me during the drive
home that next week he had to go back home to California for business and
he did not know when he would be back here, if ever.
We pulled in the driveway; I got out of the car and waited for my husband
to open the kitchen door because he had the key. He unlocked the door,
pushed it open and, again, like in the hotel, picked me up in his arms,
planted his lips on mine and carried me over the threshold. Still holding
the kiss, he turned to close the door and almost dropped me. He pulled
his sweet lips away,
"Oh shit!" he said. I looked at his face to see he was looking across the
room, I followed his gaze and saw my mother and sister sitting at the
kitchen table and the looks on their faces told me they were not happy. I
noticed that the table was covered with papers, photos and manila
We just stared at each other for what seemed hours but could not have
been more than a few seconds.
Then the shit hit the fan. Fred lowered me to my feet but we stayed in
each other's arms.
Without any preamble my sister started in, I could see that she was using
every bit of restraint to talk in a soft voice.
"Don't either of you perverts say a word or I will rip your tongues out
of your mouths.
For a long time now I have known, or at least suspected that you," she
pointed at Fred, "have been cheating on me, but never in a million years
would I suspect you were cheating on me with this other pervert." She
spat that last word out.
What she told us was that the weekend she and mom won was a sham, no
cruise, no weekend away. She, actually they, mom was in on it, made up
the whole story. They hired a private detective to follow Fred this
weekend to see if they could find out which bimbo bitch was seeing. Boy
oh boy, were they surprised when they found out exactly who he was
Long story short time here. The detective called them within minutes when
he saw Fred coming out of our house with a woman. He took some pictures
and sent them to her; she didn't recognize me right away that came later
when he followed us to the hotel where he got some really clear pictures
of us. They were fit to be tied when he told them that we checked in as
Mr. and Mrs. Fred and Carol Gleason.
He, the detective must have followed us everywhere because we could see
pictures of us everywhere, the picnic, the restaurants and just about
everywhere we went.
Fred and I were still standing there hugging each other when they gave us
We had the choice of getting the hell out of the house, both of us
perverts, immediately, or we get to choose how we were to die; we chose
getting out of the house.
Fred drove us to a motel. I was in shock and don't really remember what
happened next but as far as I can remember it went something like this.
I must have been exhausted, both physically and emotionally because I lie
down on the bed and fell right asleep.
The next thing I knew was Fred waking me up, he must have gone out
because he had a bag of sandwiches and some coffee on the table.
I realized I was still in the dress I wore on the trip home, I changed
into something more casual, shorts and a tank top.
Another long story short time. Fred made a few decisions for both of us
and I agreed with him when I heard them.
We were going to stay at the motel that night and early in the morning we
were going to catch a plane to California where his family was and he had
property. I was going as his wife. I started to say something but he
stopped me. His family knew all about him, being bi-sexual and had no
problem. He told them he was bringing his wife home and that I was really
a male but not that I was only fifteen.
All they asked if we could have another wedding for them, we agreed.
That was a little over a year ago and things are just fine now. The
wedding went over perfectly. I almost died when I saw my gown; my sister
sure had good taste when it comes to clothes, she is the one who picked
it out when they got engaged.
As soon as we stepped off the plane my husbands' sister, Paula was
waiting for us and I was introduced as Carol, her future sister-in-law. I
liked her from the start, just as I liked my husband, but not in the same
The ride to the house was short and we were soon in my room and Paula and
I unpacked my bags. My husband left us alone to get to know each other.
The first thing she asked me was if it was true, that I am really a guy.
I told her I was and if she needed proof I would take off my skirt and
prove it to her.
"Don't get your panties in an uproar, I meant no harm. Freddy thought I
needed to know because I will be helping you into your gown and he didn't
want any embarrassing moments.
Paula and I became BFFs after the wedding.
There was only one embarrassing moment for me after the ceremony, and
that was at the end when all the guests lined up and were formerly
introduced. There we were with all the guests were lined up and I
realized that I was supposed to kiss all the guys, I thought that was
disgusting. I still never considered myself gay because my husband is
the only guy I ever had any interest, but instead of being a closet cross
dresser, I am now out in the open but living as a woman.
The next day my husband's parents went back to Europe and Fred and I went
on our second honeymoon in three weeks. To make things easier in that
mode, we, Fred and I decided to have a little surgery; I was going to
have breast inserts and put on hormones to give me a softer skin and
accent my waist and hips and ass, everything else remained the same,
namely, I kept my dick.
During the next year several things happened; as mentioned above, Paula
and I became BFFs and she introduced me to several of her girlfriends and
we spent a lot of afternoons together having lunch and doing charity
work. but I soon got bored with that life and got a job working with my
husband as his office manager.
I tried several times to get in touch with my mother and sister but as
soon as they heard my voice on the phone. all I heard was dead air, e
mails went unanswered, and snail mail went unanswered or was returned
The only information I got from them was through a lawyer with a "Cease
and Desist order and a permanent OP. I also found out on my space, was
that I, Ron, was away visiting Europe for an undetermined time.
Last, but not least, we are having a baby. It will be Fred and mine; now
you may ask how the hell could that happen? Easy, by mutual agreement
Paula agreed to be the surrogate mother and I will be the father, lucky I
kept my "Donor Tube". (I just made up that phrase). We are about two and
a half months along, and just to keep things looking right I am wearing
padding and add to it as Paula shows, adding padding as necessary.
I said this will never work but I was convinced I should at least give it a go. And that is how I found myself one Saturday afternoon sat in front of my partners vanity letting her paint my face so she could bring out the feminine features, I had already lost my body hair in the interests of authenticity and let her glue nail extensions to my fingers. My next detail was to let her sew a wig to my hair, as she pointed out I would look silly if it came off. I was soon dressed in a pink dress that had no practical purpose besides making me look like a sissy.
I had been practicing walking about in the heels for a few evenings so they were not a complete shock, what was a shock was to come a little later when I was mincing around the kitchen pouring out some wine, she came in wearing the tightest fitting black catsuit you have ever seen and the highest heels I could imagine, she looked dead sexy as she fixed me with a firm stare. 'For me I assume?' taking the wine from my hand. 'You look fantastic.' 'Thank you, I have to say you look very pretty yourself. Now are we ready?' 'Well besides not really being ready for going out like this or really knowing where we are going, I am ready.' 'Oh dear you can be slow at times Rick, the clothes should give you a clue. I am dressed as a dom and you are the sissy, I am the boss and you do what I tell you to do. Got it?' 'Sorry I thought this was just some fun.' 'And it will be as long as you do as you are told'. I got a withering look 'Now get your little bag with all those girlie bits I showed you earlier and let's be going.' 'But...' I was cut off. 'This will be better if we play along to the characters we are dressed as but I can quite easily play it for real.' Her voice became stern, 'Get your bag we are going.' I felt so self conscious walking out to the car, a true sissy being taken out by his mistress. My cheeks were glowing though I did wonder if they could be seen under the make-up. I relaxed a little as we got further from home, well until we turned into a rather large drive and the mansion sized house was before us. 'Now remember your name is Rikki and you do exactly what I tell you to do, starting with mincing up to the front door a step behind me, you are my servant, toy, plaything, whatever.' I answered as she had instructed me to, 'yes mistress.' 'Easy isn't it? and the answer to that is yes.' 'Yes.' 'Yes what' Sorry, yes mistress.' 'Now let us meet our hosts.' The front door was opened by a woman in full victorian dress. 'Hi Victor, this is Rikki my little companion.' 'How lovely to see you both, you look fabulous but then you always do.' Said the person I was now thinking might be a bloke like me 'and you my dear look absolutely divine. That dress looks just perfect on you.' Then turning away from me 'I take it he is house trained?' 'Oh yes' replied my boss. 'Good. In that case my dear Rikki please take your mistresses jacket and hang it in the cloak room then find Fifi in the kitchen and see what needs doing. You my dear are coming with me.' Victor took her hand in a very elegant way and guided her into the house. I was left watching and taking in her last words 'Well Rikki, go and find Fifi see what needs doing, any trouble and I shall hear about it.'
I found the rather spacious kitchen and was surprised to find a man there in charge. 'Oh good, you must be Rikki, Fifi is run off her feet, now take this tray and circulate.' The first question was, how does he know my name, the second was have I been set up, then in walked a person dressed just like me. 'You must be Rikki, hi I'm Fifi' we touched cheeks and air kissed 'now I expect you know what is happening but just in case, this is Cyril, this is his house, well Victor's as well, and you and me it seems are the sissy servants for tonight.' I looked blankly at him/her 'your first time, well trust me it is fun, just watch out for Freddie, he is dressed as a vicar but is no saint. And I have to say your mistress is a looker, if I ever tire of mine I shall be asking her to take over me.' A little shell shocked I walked out with Fifi holding trays in our hands and I got to see what a sexy costume party I had come to. Gay, straight, unknown all dressed in costumes with some sort of sexual reference if not overtly provocative. I was nervously following Fifi about when I saw the boss sat beside a well muscled man in not much more than speedos, fake tan and oil. She beckoned me over and rather proprietarily made a show of stroking my arse under the frilly skirts. 'You and Fifi make a good pair, hope you are getting on well.' 'Yes thanks.' then I caught her eye 'Yes thank you mistress.' 'That's better Rikki.' and turning to her Adonis look alike 'he has not been training for long.' His reply cut me to my masculine heart 'She is a he, get away, never, I would have shagged her given a chance.' 'You still can, just be nice to me and I am sure my little sissy would love to keep me happy by keeping you happy.' The blood drained from my face I am sure, she touched my hand and with a comforting voice said 'Only joking, that is unless you want to or I think you need teaching a few lessons in how a sissy should behave.' I don't think my white face was fooled by the tone, the words were enough to make me worry.
I spent the first hour serving drinks and canapés while getting my arse groped by men and women. I tried to ask Fifi about it and how to stop it but she, (though I strongly suspect she is a he,) seemed to be enjoying the attention, flipping my skirts up behind me and caressing both arse cheeks while Cyril was setting out some more canapés for us.
After about an hour a buffet was put out and the guests invited to help themselves though me and Fifi were on hand to help if needed. It was after this that I had time to sit down and have something to eat and drink. I reflected on how I had been tricked, (that was my best word,) into this situation and would be wanting an explanation of my 'mistress' later. But I also reflected on how I had at first enjoyed the attention and thrill of letting her dress me, the near panic was almost exciting as she drove us here, and the embarrassment of my introduction to Victor and later to her new male friends. But I was relaxing and starting to like the attention I was getting from some of the guests, especially one or two of the sparsely dressed women could tickle my fancy anytime, I just doubted they would want a bloke dressed like me when there were, and I admit it, some very good looking men there all seemingly unattached, but then everyone else seemed to be as well.
This was a most unusual place for me to be, our usual weekend social life meant a pub or a meal with friends, how had she got us invited to this rather bizarre event. And what did it mean for our relationship, I had let her dress me in a girlie frock and I had seen her being quite intimate with a few people, male or female it seemed to matter not. And then there was Fifi and his promiscuous behaviour almost inviting everyone to feel him up, yes Fifi is a bloke like me he told me and has introduced me to his partner Becky who does not dress severe like mine but certainly is in charge. Apparently she likes to wear skirts and no knickers so Fifi can pleasure her whenever the fancy takes her, but tonight I imagine from the things I have seen already that Fifi will be servicing others besides his partner.
I was brought out of my thoughts by Victor, still in full Victorian splendour. 'Right then girls I hope you are enjoying yourselves, the costumes fitted ok?'
'Oh yes, it is perfect' gushed Fifi 'I just love it, I have asked mistress more than once if I could have a pink dress but she says it would be unsuitable for my normal duties. So thank you.'
'And you Rikki, I gather it is your first time.' I admitted it was 'and you seem to be enjoying yourself now the shock is wearing off.' Again I admitted that my initial fears had subsided. 'Well Rikki, I have a little suggestion for you, Fifi knows already and has been told she will agree by Becky. I have spoken with your mistress already but feel it only right I ask you as well. Me and Cyril like having parties but the caterers can be awkward and not get into the spirit of the event, so we are thinking of finding our own staff, Fifi you may already know cleans for us on a regular basis, but we thought this job needed more than one, hence your presence.' I had been nodding to show I was listening but was somewhere between worried and curious as to where this was leading and what had my 'mistress' agreed to. 'We plan on throwing a few more parties and will be needing you girls to help out. You have already been volunteered Rikki, but I would like to hear you agree yourself.'
I was on the spot, imagine the fuss if I say no when we leave, she had been quite bossy about this whole thing, and there was a voice at the back of my head whispering 'and what if you like it, what then?' Fifi broke my thoughts 'Off course you will, don't worry Victor she will do it, I shall show her the ropes, she will not know how she managed to live her boring life by the time I have finished training her.' I looked at my fellow sissy wide eyed 'Oh come on you can't just say this will be a one off. you look nearly as good as me, I know you like sex from the way you reacted when I fondled your arse, this is just the perfect place for people like us.'
'People like us?' I questioned.
'Yes pretty boys who are far too nice not to be girlie, that's right isn't it Victor.'
'I think I am too old to be a pretty boy but yes this is a good place for feminine men to express themselves.'
I took a moment to answer, I was confused, did these people think I was one of them, a cross dresser? They seemed to think I was going to accept the offer to help at the parties. I just did not know what to say. But the decision was taken from me as 'she' walked up to our little group.
Victor spoke first, 'Rikki was just considering whether she would like to join Fifi here?'
'Off course she would, Rikki talks of nothing else but wanting to try something different.' I nearly said 'I wanted to try something different to working in insurance.' But she cut me off 'Just let me know when you want her and she will be at your mercy.' I got the sickliest smile ever 'Now come along sugar I have meet someone who would love to get to know you.' Fifi at that moment decided to put his hand on my nylon clad thigh, give it the slightest of squeezes on that sensitive part towards the inside and say 'Go and enjoy yourself, half of the guests would love to have your company if only for a few minutes. Now off you go and I shall see you later.' Air kiss and I was dismissed.
I was lead by the hand into the main room. Since the food had been eaten the restraint on sexual restrictions seemed to have evaporated, a few were still chatting but many were openly petting and I saw one woman fondling an exposed prick. I was now worrying not about what Victor and Fifi wanted me to do but what my 'mistress' might have in mind for me. We stopped in front of a couple of sailors, well they were dressed as seamen anyway. I was introduced as Rikki, mistresses sweet sissy, I felt embarrassed at first from the way I was introduced but Sean and Peter soon put me at ease, chatting about their interests and our common interest in road bike racing. I was not surprised to see I was alone with them as cycling is something my partner is not interested in, what did surprise me seeing her on a couch with the barely clothed muscle man and unable to chat because she had her tongue in his mouth. If that had distracted my thinking, then Fifi walking past me with a man in only dungarees and a hard hat, stroked his hand over my frilly arse and whispered, 'My second of the evening. You taking two then?' but before I could reply the pink dress was gone. I turned to my sailors who seemed amused by my expression.
'This is new to you I guess?'
'Well the rules are, no one cares about who or what you are, the only thing is having fun, and from what your friend said you have guessed that getting laid is part of that fun.' I guess I was staring at them. 'And it seems your mistress is preoccupied, and she did give us express instructions to make sure you fulfilled your girlie role so might I suggest we adjourn to somewhere more private.'
'I am not so sure what you mean ' a slight tremor in my voice.
'She said you might play hard to get. Let me put it another way, your mistress has told us to break you in.'
The other sailor added 'have you ever tasted seamen?' They both laughed. 'Our little joke, s-e-m-e-n or s-e-a-m-e-n, now Cyril did suggest we might like it by the pool, what with us being water boys. Come on Rikki let us show you the pleasures being a sissy.'
I can't say I went willingly, an arm round my waist ensured I went where they wanted and soon enough we were in a small shelter by a pool. Some would say two against one is not fair and I had little enough strength as a man anyway, one simply started kissing me while the other was playing with my balls, dick and after a bit my hole. I am ashamed to say I found myself responding to their attention and when the kissing stopped I found myself confronted with the others erection on my lips. 'Now I guess you know what we would like you to do next' I nodded 'good, I expect you will like it, if not get it to the back of your mouth and swallow. Enjoy your first semen.' And without much tenderness my mouth was filled with this throbbing thing, as an instinctive response I started to suck on it. My senses were so filled with what was happening to my mouth I hardly noticed I was having fingers inserted in my arse, but when they tickled a tender spot I gasped and heard one say 'good isn't it.' A few more involuntary gasps and I heard 'Sean I think she is ready if you are.' 'Been ready since I first saw her.'
There was a pause in proceedings while things and people were rearranged, I was positioned face down over a small table, my ears were held and the now fully erect dick pressed against my lips, I felt my hands being held after my skirt had been lifted, it only took one hand to hold my slim wrists and with his other fingers he explored my hole touching that spot which made me gasp again, I was loosing control as I felt something much bigger replace the fingers, no explanation was necessary, these men were going to squirt there sticky stuff into both ends. I shut my eyes wondering if it was right to be liking some of the sensations when I felt the one in my arse tense and quicken, letting go my hands he gripped my hips and thrust into me, I would have moaned in pain or maybe pleasure except for the other sailor now let go his own stuff and filled my mouth with his ejaculate.
As they both relaxed I felt myself going limp as well, I had cum in all the excitement as well, then I was brought back to earth with a bump, there was clapping going on, one of my sailors said 'thank you, I do hope you enjoyed what you saw. Fifi I think your friend needs a little help.' The small group dispersed and I was ushered to a bathroom by Fifi who hugged me and repaired my make-up, telling me how she hated her first time but her mistress kept on making her go with men until she thought nothing of it, now he actually preferred playing with another dick to her own. She told me I was a natural and was wasted as a straight man.
And that is how I not only lost my virginity, but also my place in the world as a man who sold insurance. I later found out that I had been well and truly set up by my partner, she worked for Cyril and Victor who had a finger in many businesses, she ran one of the smaller outfits for them and had drawn her into their alternative world, first inviting her to the occasional party, then asking around if anyone knew of a replacement for Fifi as she was going to be busy as Victor's personal maid. And so the plan was hatched that if she could get me there and work with Fifi at a party, they would give her shares in the business she ran and a pay rise, I would get out of my boring job, and though she did not say, she would get rid of me.
Come the following morning I was in a very pink bedroom with the sun shining through the windows trying to work out where I was when I noticed Fifi dressed in a white satin wrap sipping coffee.
'Morning sleepy head, would you like a coffee or something stronger.'
'Where am I?'
'In your room, or more accurately the room I used to use when I was stopping over after working late. Hope you like it.'
'Sorry I am not with it.'
Fiona as she preferred to be called when not in costume explained how I seemed to have had a good night and that I had agreed to stay on as maid for them, which according to her was fantastic as it meant we would be working together. I voiced concern that I had a job already, but I was informed that as part of my accepting to work as Cyril and Victor's maid I had signed a letter of resignation and also given my house keys over, so in short I had no where to go but the lovely house I was in.
It was explained how our employees loved the Victorian era and had dresses made specially for us.
This was to be my everyday outfit, I did get an allowance for my own clothes for if wanted to go out on my own. But I should have been thankful, Fiona was required to wear far more involved outfits, like the one below.
We both had to wear corsets but hers was much tighter than mine, I thought because I was expected to be maiding while Fiona was looking after Cyril and Victor personally, but maybe it was personal preference or Fiona was told too, I never found out.
I make it sound terrible don't I, but quite a lot of the time we have the house to ourselves, a gardener comes every week to do any heavy work, and as long as the house is clean, breakfast is served properly and an evening meal ready if required, I am left pretty much to myself. The hardest part to get used to was the early starts, I had to let Fiona dress me first which was easy, then help her with the more involved dresses she had to get into, and all before breakfast was started. I soon found a luxury was the afternoon siesta. A nice quiet time of day to rest and recover in.
Of course there were the parties and over time I became a willing participant. It seemed that we both were 'signed over' by our mistresses, effectively making Fiona my boss now and she made sure I got to see and feel plenty of men, including herself when she felt the need.
I had been going to Elle's salon for a year or so now, I know I am a bloke but I keep my hair longish and regular barbers just look at me strange. So anyway I am sat in the waiting area, just waiting my turn when this real ugly woman walked in, well past her prime, not very good cosmetic surgery, thinning hair and way too much make up and jewellery. Why do the fading beauties overdress in the hope of making themselves attractive? Oh dear going off the story there, this woman walks in with a real attitude of arrogance and unfortunately just as a I muttered something very unflattering under my breath, 'Jeez I would make a better looking woman than her.' All the driers stopped working and in the silence my words could be heard especially by the mutton dressed as lamb.
What happened next is etched on my soul.
She turned, looked at me with a look that could frighten wild animals, then turning to Elle said something I could not hear and went to take her seat for whatever treatment she felt necessary to hide the truth. Five minutes later I was called to take my place at the sink to get my hair washed unaware of what was about to happen, an apprentice washed and rinsed my hair before taking me to a chair at the very back of the shop. I settled in ready for Elle.
'You stupid pillock, you have just insulted my best customer, that she is head of a law firm with a salary to make you green with envy and knows her stuff better than anyone is beside the point, you were rude back there and she is offended.'
'What can I say, I am sorry.'
'Well that is a start, but Mrs Forbes has other ideas, she is threatening you with sexual harassment and sueing the salon, though I am not sure what for but I am sure she could find something, along with that I lose a good customer and probably a few of her friends who come here as well. So I have agreed with her on a rather unusual form or restorative justice.' She paused for effect or to make me squirm, maybe both 'She wants to find out if you do indeed make a better looking woman than her.'
My damp hair was beginning to feel very cold and damp, my confidence was sinking faster than a stone, all I could think to say was 'she is joking?'
'You will find that Mrs Forbes does not joke.'
The blood was now draining from my body 'But you can't be serious?'
'Oh I can and she is.....very serious, I am to make you look like a woman and you get to see whether you look better than her.'
A bit of bravado crept back into me 'And supposing I do look better?'
'Well that would lead to several options, but for now your only option is to sit there and not cause any trouble while my team do our best to calm the waves you caused.'
'I don't have much choice do I?'
'Not unless you want to see her in court, and lose.' I caught sight of the woman looking over at me with a slim smile on her lips, she knew she would have her way and would enjoy my embarrassment.
My hair was the first part of me to undergo changes, I have hair that comes well past my collar but after a short discussion which did not include me it was decided that for the best effect I should have long blonde hair. I wanted to say 'I have a job you know' but somehow the earlier threats made me mute. For ages hair extensions and bleaching products were applied to my own hair until eventually I had hair half way down my back. The difference was amazing, even in my shirt I looked quite feminine. Next I was taken into a room with a high massage bed on it and told to strip then lie face down, I felt the warmth of the wax which lulled me into relaxing, a mistake, the first strip ripped off was the worst, but I was still having trouble holding back the tears as I turned over onto my completely bald back. The moisturiser was a lovely relief after the waxing but only for a short while. The waxing woman then started to prepare my chest for some unwanted additions. two huge breasts were firmly adhered to my chest and then with some make up applied to the edges I was pushed to spot the edges in the mirror. Amazing to look at but wrong on me. Next she concentrated on making my pride and joy as invisible as possible, hairless now but for some curly bits at the front, with glue and tape I was left with a rear facing penis that was not going to be any use to a girl in the near future. I was just thinking 'what next?' when Elle came in.
'Oh great, that is looking fine, thanks Janice, I hope you enjoyed yourself?'
'I nearly got him to cry, what do you think of the shaping, the tits have come out well.'
'They have, your contact at the medical supplies is a good one.' She turned to me 'Right pull this wrap round you, nails next I think if Rose is free.'
I am not sure what was worse, the weight of two silicone breasts pulling on my skin, having my cock uncomfortably tucked between my legs or stepping back into the shop with other customers able to see me. Rose was all business, she had been told what she was doing to me and got on with it. One finger at a time she covered my bitten nails with false ones, going back to trim and file each one before painting them with varnish in what I knew was called French tips. Would them come off, I certainly hoped so.
From Rose I as taken to a normal salon chair and Elle came in for the final work. My eyebrows were massacred as she threaded them and ripped loads out, some eyelash extensions and to my horror a needle came out and had my lips injected so they plumped up. This was going to be so hard to explain at work when I showed up next time, if I ever dare show up again. Finally she applied 101 products to my face making it change not completely but definitely into that of a woman.
Now back into the waxing room where I was to get dressed. The apprentice had been sent out shopping while I had been suffering and only now did I get a look at what she thought would be suitable for me to wear. A blue dress which was so small and thin that I could have screwed it up into a ball in my hand if I wanted, a pair of knickers, tights and some frightening looking shoes. The dress and knickers caused me no problems, the tights took a little working out but the shoes though they went on easily really messed with my balance. All the women were there for my first steps and thought it hilarious to watch me stagger about the room hanging onto the bed for support. Rose came to my rescue and gave me tips on how to walk in such high heels, adding in quite a few other posture related tips.
By now the shop was about ready to close and if I thought being made up to look like a woman, which by the way had been a remarkable success, was the end of my ordeal then being told to leave destroyed that illusion. Along with all the staff I walked out the front door while Elle locked up. it was six o'clock and I was dressed for a night out, wondering how I get home. I need not have worried about home Elle had a worse challenge for me. She was going to take me to Mrs Forbes house so she could see the fruits of the work done on me, and as far as Elle was concerned, put this awkward experience behind her and keep her customer.
I had to walk quite a way to the car park and Elle's car, but I coped. The hair had a mind of it's own and would fly round and stick to my lips requiring me to be constantly finger combing it back over my shoulder, the dress was so short it might not have shown my knickers but it felt like it did so I was pulling the hem down as well. The shoes I could do nothing about besides try and keep the walking neat and elegant while trying to ignore the discomfort of walking on the balls of my feet.
Mrs Forbes house was a huge detached house in a posh area of the city, electric gates opened as we arrived and ominously clanged shut as I got out of the car. A maid opened the door and showed through to a sitting room. I was stood there with Elle, thinking 'right get this inspection over, then home and try to get myself decent again. Maybe Elle would help me.' I was not to sure about the last bit but felt confident about the first.
Mrs Forbes entered a toy dog in her arms. A real smile crossed her face.
'You know Elle, the reason I come to you is because you can work wonders.' Elle smiled back enjoying the praise 'you young man are a compliment to her talents, and though it pains me to admit it, you are indeed a better looking woman than myself, in my defence I would say that there is possibly thirty years between us, but still you look very good.'
I thought that was it over, she had made her point, I had been publicly embarrassed, time to go home.
She continued 'Now it seems a shame to waste all this effort and what with you looking so gorgeous, how about I give Ralph a call and let him know I have a friend here who needs showing a good evening.'
For the first time since I arrived I managed to speak 'Oh no bother I am fine going home, no need to trouble Ralph.'
'Nonsense! My son needs to get out more, he never brings home any nice girls for me to meet, so you will do just fine.'
The source of my current situation left the room to find a phone, Elle suggested I take a seat and then confided in me 'she has told me a couple of times she worries her Ralph is gay, not that she is bothered by that, she just suspects and wished he would be open with her.'
From feeling the end was near I once again had that sinking feeling that this was going terribly wrong for me. 'And if he is?' I asked.
'Well I would suggest that you leave yourself open for new experiences and embrace the situation, I believe Ralph is a nice bloke, he is well connected, plenty of money, a girl could do far worse you know.' A cheeky grin on her face all the while.
'But I am a bloke under all this.'
'I know that and if he is gay then he might love that as well, some blokes have a real thing for pretty she males you know.'
I was pleading now 'please help me, I have a job, friends, things to do, I do not need a gay boyfriend.'
Without sympathy she got up 'Sometimes the consequences of our actions might seem disproportionate to initial act, but you my dear were a rude obnoxious man and I really do not care for your type, maybe a spell in that dress will soften that male attitude.' Mrs Forbes was suddenly at the door 'Ah Janice. I think I am done here.'
'I think you are, I must compliment you once more on a remarkable job and reassure you that I was only bluffing in the heat of the moment when I said those things to you.' The two women politely kissed each other cheeks and said their farewells before Mrs Forbes turned to me 'you however.........I am not bluffing, Ralph is fascinated to meet you and tells me he is free this evening. You will accompany him where ever he fancies because if you don't I shall have you paying damages for those cruel words you said earlier. Do I make myself understood?'
Oh how I wished the ground would open up and swallow me, but I looked from her ugly face to my near naked knees and elegantly long finger nails. And said with resignation 'yes I understand.'
'Perfect, now I would you like a drink and something to eat? Pin Hu will make you anything you want, her English is not so good but she is a wizard in the kitchen.'
I hardly said a word to the quiet Chinese girl who put together a small bowl of salad along with an unusual flavoured tea, jasmine I suspected at the time, definitely not tetleys. About half seven this man appeared at the door said hello to Pin Hu while making a long studious assessment of me, to be fair I was doing the same. I was sat on a stool, knees together (even I knew not to sit with knickers on show), back upright, shoulders back chest forward, it just sort of happened that way, must have been compensating for the extra weight up front I think. So that is what he saw, what I saw was a good looking man, possibly over six foot, not over weight but hardly a rake, just well proportioned and fit, a bit of stubble, blue eyes, short dark hair and suit that was certainly not off the peg from a store. In fact if I was six inches taller I would say that he is what I would hope to look like if I had the money for the suit.
'So you must be mother's latest attempt to find me a partner.'
I got off the stool and offered him my hand to shake 'hi I am Julian, I got into a little bit of bother with Mrs Forbes, your mother I guess, and to teach me a lesson she had Elle do this to me.' With a sweep of my hands I gestured to my current state of dress.
He started laughing 'I thought mother was joking when she told me that I should come round to meet you. But to be honest I still think she is teasing, no way are you a bloke called Julian, a girl called Jules possibly trying to get me to admit to something in one of her games. But you are no bloke.'
I did not know whether to be proud or hurt by his comments, my male ego was certainly taking a battering. 'Your mother is not joking, my name is Julian and she had this done after I said something at the hairdressers we both use.'
'A bloke using Elle's!'
'I am not the only one, Elle is good with hair.'
'She might be, but I mean this a long way from getting a trim.'
'What do you want me to do show you my cock.' I was getting fed up with being denied my true gender.
'Maybe later' he said with a smirk 'so ok, Julian, I can't keep on calling a girl Julian, can we go with Jules or Julie, maybe Juliette? If mother wants you to learn some lessons and it seems to have fallen to me to take on your education for the evening.'
Just then Mrs Forbes came in 'Oh Ralph how wonderful to see you' she wrapped her arms round him and gave him a hug 'I see you have meet, gorgeous isn't he, thought you could take him out and let him see how well brought men behave.'
'Mother stop, you are mad, you want me to take this er man but more likely a woman out tonight.'
'Yes, you work to hard and I worry about you living alone.'
'I have friends.'
'Not the same dear'
'You need a partner, someone to be home when you finish work tired.'
'Like you mother he teased?'
'No not like me, your father was the better one at home anyway.'
'And you think' he looked over at me 'Jul.....whatever will make my ideal mate?'
'I don't know, but you never know, maybe.'
'But if you are not lying she is a bloke.'
'Do go homophobic now, your friend Ash a few years back was the gayest man I ever met, you were close till he moved to the states.'
'We still keep in touch.'
'Good, now.........I don't think Juliette has eaten much all day and he is dressed up for going out so why not take him to that nice indian on the high street and maybe to that club you like to go to.'
'I give up mother, Juliette, Julian whatever you are called come along she always gets her own way so we might as well give in now.'
Like a knife in my back Mrs Forbes watched us walk out together 'you make a lovely looking couple.' this was not helped by me getting a good look in a huge mirror in the entrance hall of me stood next to Ralph, even in my heels he was taller than me and far broader. Next to him I looked like a trophy girlfriend.
It was a warm evening and Ralph promised the high street was not far away, so we walked. The walk along pavements past shops and among the general public was a frightening experience, I expected everyone to turn and make some comment about that bloke in a dress. Thankfully Ralph kept close and guided me into the indian restaurant. A quiet table in a corner suited me fine, a bottle of champagne ordered, poppadum starter and I started to relax as the bubbles sped the alcohol into my system. I was even beginning to like my hosts company, he talked warmly about his parents, told me about his work in the family law firm, his numerous outdoor activities, my life seemed quite dull beside his, I did not have a car, parents who wanted me or a nice home, but when he asked if I had a sense of adventure I hesitated before saying yes, well I had done plenty of scary things on mountains but I was not sure that was what he had in mind. We finished up our wine and food, Ralph paid the bill and invited me to follow him as he took my hand leading me out to the road. Amazingly he hailed the first black cab we saw and it stopped. I was trying to protect my knickers while he gave the driver an address, soon enough we were back on the pavement and going into a smart club, the doorman approached Ralph 'Sorry sir, you know the rules, men only.'
Ralph calmly replied, 'I know John, and this is Julian a friend of mine.'
'Sorry sir but Julian does not look very much like a man to me.'
'John do you want him to lift the hem of that lovely dress and prove it?'
I was really feeling very awkward at this confrontation.
'Sir if your friend was to go in it would cause a proper fuss.'
'That is a shame I rather hoped to let Julian see what a nice place this is, but I do understand your position.' He turned and took my hand again 'Come on I know somewhere more suitable for your beauty.'
A short walk and were in a bar full of openly gay people with no restrictions on how you looked, I did not consider myself gay but given how I was dressed I felt I fitted in quite well with the butch leather boys, the camp men and straight looking but not acting people who clearly preferred their own sex, even a smattering of women enjoying each others company. Well Ralph seemed to know quite a few people there and from the way they touched he was clearly comfortable with gay men, a few enquired about me and why Ralph had brought a woman, that was until I spoke and they realised I was not quite what I seemed and for some I became more interesting. The drinks kept on coming and I loosened up enough to venture to the ladies on my own and talk to some of the other customers. It was quite strange to be somewhere that accepted me as I was, some even welcoming me a little too much as I felt a hand on my arse more than once. Ralph could be quite possessive though and would put a hand round my waist and hold me close when I was with him, and as we got more drunk the hand go lower until it was on my arse and I did nothing to move it away. I had been flattered enough to think some of it might be true, and enjoyed the feeling of being attractive, and Ralph was clearly finding me attractive.
Well his attentiveness and my feeling attractive meant that my barriers were down, I had never felt like this before and when he said we were leaving I never asked where we were going, just took his arm and tried to keep up with him as I staggered in my heels. A taxi ride and we were outside a nice apartment bloke, reception said hello to Ralph and smiled at me.
'I am guessing you have nowhere to go looking like this? So thought you might as well come home with me and we can sort something out in the morning.' He suggested as we let the lift carry us up several floors.
'Thank you, I am not sure how I would fare looking like this where I live.'
A nice luxury flat like the ones I had seen in magazines was where Ralph lived, as he went to put a CD on he pointed to the drinks cabinet and asked me to get him a malt whisky, I picked out amaretto for myself, returning to him I gave him his glass which he took but then caught me and pulled me onto his lap.
'You have been quite amazing tonight, mother lead me to believe you were being punished but I don't see it myself, you have enjoyed yourself haven't you?'
I admitted that I was terrified most of the time but he was a calming influence and I had rather liked the gay bar.
Then he dropped a shocker on me. 'I have a suggestion to make. You have a crap job, live in a crap place, I have a great place and enough money to support you so you don't need to work.' I was nervous about where this was going but carried on listening. 'What I need is a female partner, mother's suspicions are correct I am gay but dressed like you are, people get to see a woman while I know I am with a man.'
'But .......' he cut me off.
'I would pay for new clothes, any coaching you might need, you can keep this place clean if you want something to do or in time come and work at the office.'
'But I am not gay.'
'Well you were hardly fighting me off earlier.'
I tried to explain how it felt to be attractive for a change.
'So you are attractive to me and I think you find me ok.'
'You are nice.'
'So what I suggest is try everything once then you know in yourself what you like.'
'I do.' And he pulled me to him and I got my first kiss of many then night. I followed his logic and being relaxed had no problem finding out if I liked being with a gay man. Before we made it to the bedroom I had felt my first cock (other than my own) with my fingers and then tongue, it had a very unexpected feel to it, and cupping another man's balls so he clearly found pleasure in that touch was a nice thing to do. There was no need for me to undress, the dress just rode up over my hips exposing my knickers, Ralph made some joke about my cock and how it proved I was a man, well almost, which was before he took his pleasure in me as he screwed my arse. I could have felt used in this situation but the way he did it made me feel wanted, he hoped I would enjoy the moment with him so took care to treat me well. As it was nothing spectacular happened other than I now knew something of what it is like to be in a woman's place in bed, and in all honesty I quite liked it.
The alcohol, exertions both mental and physical overwhelmed me quickly and I was soon asleep, not that I was aware of it at the time. But the next thing I knew was waking up with Ralph watching over me, propped up on one elbow, smiling. I cleared the mass of hair stuck to my face and realised I had long nails after I had caught myself with one.
'Oh yes, morning I guess.'
'How are you this morning?'
'You don't look as good as yesterday that's for sure. Breakfast?'
'A coffee would be nice.'
I got up remembering how I had ended up in a man's bed and the physical alterations that my body had undergone, sitting to pee was the least of my worries. I found a brush and straightened the dress hoping to be a little more modest in my appearance.
'Coffee.' Ralph had two cups in his hands. 'Now have you thought about my suggestion?'
'Not much really, been asleep most of the time since you made it. But one question is, what do you get out of it?'
'Oh that is easy, a partner at home, someone that fits the normal partner image, you seem to like being with me, someone that seems to like finding out new experiences, you are bright but not ambitious, so ideal company and support for me when stressed. Oh and I just want to see mother's face when she sees you next. I think it will be a picture, she was hoping to teach you a lesson, and well in a way she has. You have learnt to open yourself to new experiences for sure.'
I was trying to quickly work out a pro and cons list in my head, but all I could think of was how Ralph had made me feel wanted which had not happened in years, and if I had to wear a dress then so be it, I would wear a dress. Who knows how long it might last, but in the meantime I had an opportunity to live the cossetted life of a stay at home partner. So I said 'Yes' but did ask if I could wear longer dresses and lower heels at least some of the time.
To seal our new relationship we kissed and embraced until my partner was excited enough to take me from behind over the kitchen table. As he withdrew a thought flashed through my mind which I would never have considered possible a day before 'Gosh I am his wife. Best be a good one.'
"So what's the problem, babe?" said Lisa, making a face at Mike as she
stripped down to her bra and panties.
"The problem is I'm getting fed up with being manhandled by men and all
of you girls," said Mike nastily as he kicked off his boots. "Just go to
your stupid party, and I'll see you when you get back later."
"Well maybe you hate us, but you don't seem to mind the boys," said
Ginny, as she pulled her top over her head.
"What the hell does that mean, Ginny?" said Mike, getting very pissed
"Nothing, bitch. It's really none of my business princess, so I'll shut
my mouth," said Ginny, heading into the bathroom and closing the door.
"Who is it?" said Beth, hearing a knock on the door.
"It's just Vicky, girl," said Vicky as Lisa opened the door.
"Hey Vicky." Lisa hugged her. "Thanks for coming."
"It's no problem, and I enjoy helping Monique. She's really been great,"
said Vicky, putting down two packages. "Don't worry honey, I'm just here
to help and get all the pins out of your hair."
"Fine," said Mike, sitting down in front of her.
Vicky gently removed pin after pin, letting down his updo as Mike sat
their watching the girls change and get ready to go out. When she finally
finished after ten minutes, he watched her fishing through her bag and
pulling out some cosmetics.
"Chin up honey, and close your eyes for me," Vicky ordered as she began
working on his eyes.
"Vicky, I'm staying in," said Mike, opening his eyes as she stopped
working on him. "I've had enough today."
"Really? You decided to let your girlfriend go out to a party full of
celebrities looking like that, without you?" said Vicky, looking over at
Lisa as she was working on her own makeup. "You sure about that?"
Mike stared at Lisa, as she was now bending down, buckling the straps of
her stilettos before standing up and adjusting her cleavage in the
mirror. She was looking amazing, with her hair straightened and flipped
to the right side and dressed in a one piece skin tight purple mini
She looked over at him smiling as she now knew he was staring at her, and
a big smile came over her face.
"So?" said Lisa, holding out both hands with her palms up. "You have
something to say, or just looking?"
"I changed my mind," said Mike. "I'm coming. I mean we came here to be
together, so I'm sorry I was being a jerk. And Vicky made a special house
call, so I guess I can't waste that."
"That's my girl," Lisa smiled. "Get ready and we'll talk at the party!"
"Great honey. Then let's get you ready," said Vicky, getting back to work
on his face.
He now felt her working rapidly on his makeup as Lisa was diligently
watching and putting in her two cents worth. She walked behind his head
as he could feel some tight clips digging into his scalp, and heard the
sound of some snaps. She then stood him up as Lisa and Beth quickly
stripped him as he stood there actually getting some relief now as they
released his corset. They rolled off his stockings and replaced them with
some simple nude suntan hose before snapping the firm control top. Vicky
held up his hair from behind now as they then had him step into his
dress, straightening as they pulled it up and slid his arms into the long
sleeves. He held his hand on Lisa's shoulder as he immediately grew
height wise as he stepped into his shoes for Beth, knelt in front of him.
Vicky now changed his earrings and jewelry before spritzing his hair and
picking at it with her fingers. She then touched his neck and wrists,
instantly clearing his nostrils from his now very strong perfume.
"Very sexy. Smile girls," said Vicky, admiring her work now as she
snapped a quick picture. "You girls will have a blast tonight. See you in
the morning Monique, before you girls hit the slopes."
Mike looked down, knowing immediately he was in for trouble as Vicky
hugged the girls and left the room. He stared down at his fully exposed
legs and high heels as he wiggled over to the floor length mirror.
"Looks like somebody's dressed to get some tonight," said Ginny, as she
emerged from the bathroom and looked over Mike.
"And you're not," Lisa teased back at her as she walked over and put her
arm around Mike.
"I didn't say I wasn't," said Ginny, laughing and gesturing with some
attitude. "Hell, we all are I guess! I mean what the fuck! Should we wear
nun's outfits to a celebrity bash. I don't think so!"
"You're looking very hot, honey," said Lisa, rubbing her hand on his ass.
"And that's the way I like you."
Mike stared at Lisa touching his ass and then thigh, feeling himself
getting aroused but could feel the incredible tension as his manhood was
tucked and trapped. He looked at his long bare legs next to Lisa's as
they stood side by side in short dresses and thin stilettos. His shoes
were 5 inch pointy closed red classic pumps, with a thin red heel. His
dress was actually comfortable he thought, as he moved looking at himself
and feeling the form fitting, soft black velvet spandex type fabric. It
was strapless and off the shoulders on top, having long tight fitting
sleeves down to his wrists, and revealing his collar bones in a sexy way
as it cut straight across his upper chest and back. It somewhat masked
some cleavage under a thin see through v-shaped mesh in the middle, and
was ultra short and tight, maximizing his curves and ending just 2 inches
past his ass.
He twisted now, glimpsing a side view, noticing that on each side from
his upper rib cage down to his waist were a series of open 4 inch round
rings weaved into the dress, revealing quite a bit of skin inside each
ring as he looked at his side profile. He also noticed the series of
thick cascading long loose curls arranged in highlighted blonde layers
down his back, which ended just above the crack of his ass. In front, the
curls from his updo had been picked out and blended into this new style,
which was still flipped to the right across his face and now had a
distinct left part with a his hair tucked behind his left ear, exposing
his very large six inch silver hoop earrings on that side.
His makeup was slightly more dramatic now around his eyes, with dark
shadows, and his lips had been more heavily glossed yet were still a
"Yup, we're ready," said Lisa, answering her cell phone. "Thank you so
much George. See you in a bit."
The girls quickly put on their coats and grabbed their stuff as Ginny
held the door. Beth held out a red ¾ length coat, which she slipped on
Mike and handed him a red shoulder bag. They walked downstairs and around
the corner, huddling together in the frigid cold as the wind blew
As they turned the second corner, Mike looked up, seeing the stretch
black limo as he watched a driver emerge and open the door.
"These things hold well. That wind was nasty," said Lisa, fussing with
the back of Mike's hair. "I'm going to have to get me some of these clip
ins. They're gorgeous!"
"She like matched them perfectly," said Beth. "You could never tell.
Vicky is amazing."
"I think I'm going to get my hair done by her before we go home. She's
awesome," said Lisa.
"Monique, you have no idea how spoiled you are girl," Ginny teased him as
the car stopped.
The short ten minute ride ended as the driver opened the door, revealing
the amazing Ski house as they stepped out following a good sized crowd of
"Holy shit," said Lisa, as her jaw dropped, seeing the huge house. "I
can't believe we're actually going to a party in a place like this!"
"We're definitely getting fired," said Beth, freezing. "No way are we
supposed to be here."
"Are you kidding me," said Ginny, hiking up her skirt a touch and
adjusting her top to show more cleavage. "Who cares Beth! I'm going to
find my future husband in there."
"Let's do this!" said Lisa, joining arms with Mike and Beth as they began
The party was packed as they walked in, immediately being handed some
champagne. This was certainly no mere house, as they found themselves
inside one the most impressive slope side mansions that money could buy.
In some ways it was a typical slope side estate, decorated in natural
stones and neutral colors but the dramatic open foyer overlooking the
immense great room was impressive. They stepped down a few short steps
into the great room, feeling like they were almost outside as it
contained wall to wall and ceiling to floor windows spanning three
stories. Spot lights shined onto the slopes, as the view of this winter
wonderland mesmerized the girls, as it was a view as beautiful as any
they had seen from the lift. They sipped and sampled the finger foods,
enjoying their first taste of the life of the rich and famous, star
struck by their surroundings. They mingled, noticing a lot of familiar
faces from work until George came over, putting his arm around Lisa as he
"I'm so glad you ladies decided to come," said George, giving her a hug
and a kiss on her cheek as he instantly had his arm around her. "Lisa,
you look incredible."
"Thank you," said Lisa, being flirty. "So do you, Mr. Clooney."
"Stop, I'm just George here, please," said George smiling as he looked
into her eyes. "Ladies, excuse us for a minute. There are some people I'd
like you to meet, Lisa."
It was hard to fathom that Mike was watching George parade his girlfriend
all over the room as he didn't take his eyes off her for second.
"Somebody's jealous, I'd say," Ginny grinned as she nudged him. "Maybe
you should go over there and fight for your girl."
"Yeah, like that'll work dressed like this," said Mike, rolling his eyes
"Oh you're so right, Monique," said Ginny, lifting his hand and fanning
it out. "How could I even think you asking you to break a nail?"
"Stop teasing him, Ginny," said Beth, as he pulled his hand away. "She's
just doing her job and he loves her."
"Love, Huh?" said Ginny sarcastically as they watched Lisa giggling like
a little school girl, as George has his arm around her and was leading
her up the long circular stair case. "It is an interesting relationship
you two have, I must say!"
Mike gulped, downing his champagne and then Beth's as he began fuming,
unable to take his eyes off George and Lisa.
"That George loves showing off the sights," said Sebbe, sneaking in next
to Mike as he rubbed his back. "Good evening, Monique."
"Oh good evening, sir," said Mike, startled as he knew the drill now as
Sebbe kissed both of his cheeks and then did the same to his friends.
"You look ravishing, darling," said Sebbe, now returning to Mike and
kissing his hand. "Cheers ladies."
"Thank you," said Mike as Sebbe handed him a drink.
"Cheers ladies," said Sebbe, clinking glasses with his and then sipping
before speaking again. "How about we take a walk and I'll show you those
gorgeous views your friend is seeing. Trust me, the views here are so
incredible you can hardly imagine them. They must be seen to be
"Oh, you read my mind Sebbe. I'm definitely having a hard time imagining
much of this, let alone appreciate any of it," said Mike, taking his arm.
"Meet up with you later, girls."
"He doesn't trust her," Whispered Beth, sipping her champagne. "I think
he's crazy, but I guess I can understand his feelings."
"You're kidding right, Beth?" Ginny giggled. "She's with George Clooney!
One of the hottest richest guys in the world. How could she pass that
"Stop, I don't think she'd cheat on him?" said Beth.
"She shouldn't, because he's such a catch? Of course what am I thinking?
She should certainly pass up a movie star, because who wouldn't when
their boyfriend is that pretty? said Ginny sarcastically. "You know what,
she may not be the first one cheating anyway."
"Ssspppiiitt!!!" chocked Beth, giggling as she spit up her drink, looking
up seeing Mike being led up the stairs by Sebbe. "He won't! He's
"I thought he was when we got out here, but you have to admit he makes a
sexy girl." Ginny shook her head. "If I was a guy, I'd fuck him."
"That's so sick, Ginny," said Beth, giggling as she sipped her champagne.
"He does make a gorgeous blonde though, and I haven't seen him in an
outfit yet that looks bad on him. This dress tonight looks amazing on
"Look like Sebbe agrees with you on that, Beth," said Ginny. "And his
hands seem to have slipped off his back as they're walking up those
As the girls watched, Sebbe seemed to be slightly touching Mike's ass as
they walked up the long curved staircase. As they got to the top, Mike
could see Lisa outside on the balcony chatting with George as he was
rubbing her back and snuggling with her in the cold of the night. They
were laughing and smiling as they seemed to enjoy each other's company,
as Mike was oblivious to Sebbe's touch as his mind was elsewhere, focused
on Lisa and George.
"It's an amazing view of these wonderful mountains, isn't it?" said
Sebbe, sliding his fingers between Mike's as they looked out the large
"What was that?" said Mike, not knowing what to do as Sebbe's thumb was
rubbing his fingers. "Oh uumm. Yes, very beautiful."
"You seem distracted my dear?" said Sebbe. "Am I making you
"No sir," said Mike. "Sorry, I was just a bit distracted by the beauty I
"So am I this evening," said Sebbe, softly brushing some stray hairs from
Mike's face. "And please call me Sebbe of course."
"Certianly Sebbe," said Mike. "It is incredible here. What a view."
"Indulge me, dear. There's an even more incredible spot to take in the
scenery," said Sebbe, turning while holding his hand. "It's
Sebbe didn't wait for an answer as they walked down the hallway and then
climbed a series of tight spiral stairs. It was tough to balance his thin
heel on the small triangular step of the tight radius spiral, but before
he knew it, they were on the top story of this amazing home.
"You weren't kidding," said Mike, breaking Sebbs's grip from his fingers,
realizing they were in a circular type tower at the very top of the home.
"I can see the mountain, the town, everything and from every direction."
"Yes, It's an amazing 360 view," said Sebbe.
"It is breathtaking," said Mike, taking it all in as he circled the room,
looking out in every direction. "You were really right"
"I know I was!" said Sebbe, taking a bottle and some glasses from the
small bar. "I was the one that had his architect add this when he
designed this home."
"Incredible," said Mike, looking out before freezing in his tracks. "Wait
is that, a hot tub? Is that?"
"Yes, that George is the ultimate playboy," said Sebbe, looking outside
and having a chuckle. "Drink and relax my dear. He's got a few of them,
and an outdoor heated pool."
Mike downed a shot as he was stunned, seeing Lisa in the hot tub with
"Don't be so distracted by your friend, Monique," said Sebbe, pouring him
another drink. "She'll be fine and I'm sure she's not worried about you."
"You're not kidding," said Mike, pissed off as again Sebbe wiggled his
fingers between his and led him to the other side of the room. "Obviously
"Take in her beauty, Monique," said Sebbe, as they looked out the other
side of the room at the mountain. "Look at her. I told you she's
breathtaking. This is nature at her most beautiful."
"It's true," said Mike, as Sebbe stepped behind him now and took his
other hand, touching his hair.
"Appreciate the steepness and the curvature," said Sebbe, softly moving
some curls and touching his neck ever so gently. "Breathtaking beauty,
like you my dear."
At that moment, Mike realized he had put himself in a very bad position.
He gently felt a very different steepness and curvature at the back of
his dress, pressing against his ass as he quickly spun around, looking at
"I think we should go back down, please," said Mike, panicking.
"Oh Monique, don't be nervous," said Sebbe, softly touching his face. "I
know all about you my dear, and I've always known."
"You do?"! said Mike surprised and pushing him back. "I'm not sure we're
thinking of the same thing here."
"Monique, of course we are," said Sebbe. "You're a wonderful actor honey,
and I plan on helping you with that. You're perfect in your role. With
some work, and a little more training, the stage will be yours. I'm a fan
and I plan on being a teacher if you'll let me. As you know, I've got the
connections to help you, but the rest is up to you."
"I can't believe it," said Mike, stunned. "I thought no one beside my
friends and Miss Adams knew about me."
"No one does. That is, except for me," said Sebbe. "Did you think her
pairing you with me was a coincidence?"
"Wow!" said Mike, still somewhat stunned. "That's incredible!"
"No dear, it was your destiny," said Sebbe. "Now,, have you decided if
you'd like my help?"
"Of course I do," said Mike. "It's my dream to perform. To be someone."
"Then you'll need to let me guide you, my dear," said Sebbe, looking him
dead in the eyes.
"This has just all happened so fast this weekend," Replied Mike as a tear
flowed down his face.
"I worked my whole life performing, always hoping for a break, but never
did I think it would happen! Especially like this!"
"Well, this is your chance to take advantage of that," said Sebbe, wiping
the tear. "Think of this as the critical scene where you're the lead.
It's your moment of truth."
"Really?" said Mike, getting nervous as Sebbe took his hand and then
"Look out at the pure white powder covering that majestic hill and tell
me what you see," said Sebbe. "What's your first thought?"
"I see the sheer size and beauty," said Mike, as Sebbe rubbed his fingers
ever so softly.
"Yes, but what you don't think about is that under that powder are the
jagged rocks and dangerous peaks," said Sebbe. "Either way, her beauty is
absolutely breathtaking! Either way, so is yours!"
"Sebbe, you know I'm no beauty by now, obviously," said Mike, giving him
a funny look and glancing down at himself, still holding hands. "I'm not
sure if it's me talking to you, or am I still in character?"
"That's up to you my dear, but the great ones never break character, and
I truly believe sometime characters choose the people they were meant to
be. When I look at you, all I see is the sheer beauty which we both know
is not skin deep. I see Rapunzel looking to escape her tower and find
herself," said Sebbe, lifting a long section of his hair. "I see long
luscious curls perfectly draping across an incredible figure and deep
eyes that display deep emotion. You are Aspen mountain, Monique. A little
powder dressing up natural beauty. Think about how you felt when you
first saw it. You remember how breathtaken you felt."
"Yes," said Mike, feeling it and getting emotional as tears flowed down
both cheeks this time. "Yes, it's overwhelming."
"Good, then hold that feeling inside you. Bottle it up," said Sebbe,
looking into his eyes and cupping his cheeks with his hands again, wiping
away the tears. "Because that's how I feel about you. You're
Mike was complexly overtaken with emotion as Sebbe leaned in, initiating
the soft passionate kiss. It was impossible to do anything other than
allow himself to be immersed in the passion, as it was a kiss unlike
anything he had ever before experienced. It was soft and gentle and
somehow in his mind he was in character as a woman. His head was spinning
as Sebbe's arm was around his neck cradling him, before finally the kiss
advanced from wet and tender to intense, as Sebbe's tongue was deep into
his throat. He couldn't stop himself, overcome by the moment and it was
crazy but his own tongue was deep in Sebbe's mouth. This kiss lasted a
good ten minutes, before finally they both took a breath as he couldn't
believe what was happening, almost sobbing as he stared at his lipstick
smeared all over Sebbe's face.
As he worked on catching his breath, Sebbe poured them another round of
drinks and he pounded down a shot as they stared out at the mountain side
"Sebbe, I ah," said Mike, as Sebbe put his finger on his lips. "Please
I'm not gaaa."
"I know dear, but there's nothing to worry about," said Sebbe, "Neither
am I, and of course neither are some of the world's finest actors that
have shared many kisses that they normally woudn't."
"Oh, I didn't know I was acting," said Mike, surprised, touching his
"See how talented you are. Gorgeous, passionate, riveting," said Sebbe,
smiling as he stepped behind him, wrapping his arms around Mike's waist,
gently taking both of Mike's hands. "There's no one else here with me but
a beautiful actress. I'd say you aced that audition."
He rubbed Mike's fingers gently and then kissed his neck softly from
behind, before Mike sensed Sebbe growing very stiff against his left ass
cheek. After a few small rubs against his dress, Sebbe pulled away one
hand as Mike heard a brief ripping sound and then watched a small square
wrapper flutter to the floor, landing near his left shoe.
"Sebbe, what are you doing?" said Mike, panicking as he heard the
distinct sound of a zipper and looked down, hearing Sebbe's belt buckle
clang against the floor. "Didn't you just say this was an audition?"
"Yes, and you're a hit my dear! Now it's time for your finest performance
yet, gorgeous. Consider this a brilliant career move for you! One that's
propelled many young Hollywood starlets," said Sebbe, nibbling on his
neck. "I know you're not ready to take this next step orally, but this
will be a good start for us. Relax, I always come prepared and of course
I'll be gentle."
Mike began trembling as Sebbe pushed him forward slightly as he lifted
his short skirt. Mike reacted instinctively, holding out both hands in
front of him, preventing himself from hitting the cold tower's large
glass window. Before he could even blink, he could hear the squishy
unravelling sound he knew too well, realizing Sebbe was winding the
Trojan up his member. He braced himself, spreading his palms open, almost
whacking face first into the glass as it all happened so fast. He
cringed, feeling Sebbe's hands tear his stockings open from behind.
Sebbe's finger tips sent a chill up his spine now, as with tremendous
skill, the elastic from his gaff was delicately lifted from his crack
before it snapped below his cheeks, giving him a little jolt. He wanted
to jump from the tower as he instantly sensed the slippery lubricant
covered latex touch his anus, knowing a much larger jolt would be coming
and then it was only a -second before he felt the initial push. He had no
idea what to do, stiffening his spine as he felt Sebbe kick at his left
pump, widening his stance as panic filled his body. After the second
little kick at his left ankle, his legs were adeptly parted, realizing
any chance of resistance had been removed. Sebbe pushed with some added
force now, rubbing his hands all around Mike's body as he felt ready to
jump through the window.
"Time to relax and let down that hair, Rapunzel," said Sebbe, whispering
in his ear. "For tonight, just enjoy the beauty of mother nature, and let
me help bring out the true woman in you."
"Sebbe please," screamed Mike, unable to prevent the penetration as he
slapped his right hand over and over, pounding the window from the
initial pain. "Mother nature! You mean, mother fucker does that hurt!
Holy fucking shit!"!
"Stay calm, beautiful," said Sebbe, kissing him over and over on the
neck. "It'll help relax your muscles and once you accept this, you'll
.He was almost hyperventilating, until finally some of the pain subsided
as his muscles relaxed a bit as Sebbe was taking it slow. He moaned in
pain for a good ten minutes until Sebbe was really pumping away with some
vigor and speed. He pulled his neck around, sticking his tongue in Mike's
mouth, kissing him a few times and was all over Mike, nibbling his neck
and shoulders. After five more minutes, he was practically lifting him
off his heels, feeling him push in harder than ever as he wrapped his
arms tightly around him, holding the penetration. Sebbe leaned him back
as he accidentally banged his face into the glass twice before feeling
him tense up, knowing he was exploding inside him, as finally he stopped
panting. He held him so firmly for a few moments, until finally he pulled
out and turned Mike's neck back as far as he could, French kissing him.
Mike was ready to puke when the kiss broke, looking down as he watched
his stiffness subside and Sebbe pull off the rubber. He had no idea what
to say as Sebbe pulled up his pants and then stunned him, as he reached
down, grabbing Mike's loose member and tucked him inside his gaff as he
fixed the waist band.
"I think these are garbage now," teased Sebbe, sliding down his ripped
"Woah, easy," sighed Mike, stunned as Sebbe lifted him off the ground,
cradling him as he carried him over to a small loveseat.
"I think my queen deserves to be off these feet for a bit. Don't you?"
said Sebbe, as he held on with his arms around Sebbe's neck.
As they sat, he placed Mike on his lap and with one arm holding Mike's
neck, he wasted no time initiating a long deep kiss again. When it broke,
he ever so gently stroked his hair and his face before removing his shoes
and pulling off the ripped hose. He held him, snuggling with Mike and
took great care massaging his feet and toes as Mike just lay there
exhausted, until finally he passed out in his arms.
"Holy crap!" Yelled Mike, jumping up at seeing the sun in his eyes.
"Good morning, gorgeous," said Sebbe, as he was startled awake.
"What time is it?" Cried Mike, jumping up and pulling the straps of his
pumps around his ankles.
"It's 6am," said Sebbe, rubbing his eyes. "Are you in a rush?"
"I have to get back," said Mike. "I have a hair appointment at 8am, and
then we hit the slopes."
"Don't panic. I'll call my driver," said Sebbe, as Mike jumped up,
straightening his dress.
"Thanks, I really gotta go," said Mike as he looked out the window,
seeing them grooming the mountain.
"No worries," Sebbe smiled and scratched his head. "I'll see you
Mike grabbed his purse, running down the spiral stairs. As he got to the
bottom, he saw his red coat hanging alone near the door and snatched it,
running out the door. He jumped into the waiting limo and sat back for
the short ride to their room. He folded down the mirror and did his best
touching up his face, as he could see the slightest stubble beginning to
push through and then took out his lipstick, fixing his lips. As the
driver pulled up, he quickly jumped out and ran upstairs getting some
looks as a scattering of a few girls sat in the lobby having some morning
"Look what the cat dragged in," said Ginny, sitting up in her bed as Mike
tried sneaking in.
"Amazing," Gargled Lisa, with her tooth brush in her mouth as she peeked
out of the bathroom.
"I fell asleep upstairs," said Mike, as she slammed the door returning to
the bathroom. "And what about you? I saw you all over Clooney!"
"Really!" screamed Lisa as the door flung open as she pushed Mike back
onto the bed. "You saw shit, asshole! You were busy with that weird
director asshole! You think I slept with George Clooney?"
"I saw you in the hot tub, Lisa!" screamed Mike. "I didn't see you screw
him, but I saw you attached to him like a cheap suit!"
"Unbelievable," said Lisa, throwing the alarm clock at him. "What you saw
is what I've been doing for two fucking days. You saw me buttering him up
and being introduced to everyone important. You saw me networking, moron!
You saw me getting the business cards from some of entertainment's most
important people! That's what you saw."
"Lisa, I don't know what to say," said Mike, putting his head down. "I
thought you were screwing him. I guess I wasn't seeing too clearly."
"No shit, asshole," said Lisa, waiving her finger towards his legs and
then put her hands on her hips. "What about what I see now? Where are the
stockings you had on last night? And you definitely didn't leave here in
that color red lipstick? Maybe you're the one that's got some explaining
to do, Miss Monique!"
Mike had no reaction as he realized she was right, and knew he no longer
had on his hose.
"Lisa, all this is crazy," Mike said, trying to explain. "You know I
didn't sign up for any of this."
"Please!" said Lisa, holding up her hand in his face to stop him from
talking. "One more day and it's over. Go take a shower or you'll be late
for your appointment. Pop the little clips and the extensions will come
right out. As it is, your beard is peaking through your foundation. I
can't talk about this anymore."
Lisa walked right by him in her bathrobe, leaving their room. He went
into the bathroom, showering and scrubbing off his makeup. When he came
out, everyone was gone but they did leave him some clothes, as he slipped
on the jeans, sparkly silver sweater, and furry boots. He grabbed his
purse, shoved the extensions in a bag and headed over to the salon.
"There's the naughty girl," Brittany greeted him. "The buzz is you were a
dirty girl last night."
"Who's saying that?" asked Mike, annoyed. "I just fell asleep and got
"Whatever, princess," said Brittany, taken aback, throwing up her hands.
"Let's go wash your hair because obviously you're not in the gossiping
mood this morning."
Brittany brought him to the back and caped him up before leaning him back
and switching on the water.
"So, aren't we a little bit of a diva this morning, honey," said Vicky,
coming over and handing him a coffee as she sat him up "Sit and let me
just do your foundation while you take in a little java. Your hair could
use the deep conditioning, so we'll let that stay in for twenty minutes
and then I'll blow it out."
Mike took some sips between her sponge strokes, as he wondered how much
word had traveled. He gave no trouble to Vicky as she brushed at his
face, and did his eyes before finally she brushed at his lips. He took
his last few sips, noticing the pastel pink lip color on his cup before
lying back as Brittany finally washed out all the conditioner.
"I'm sorry I gave you any attitude, Brittany," said Mike, feeling bad as
she dried his head.
"We all have our times of the month, Monique," replied Brittany, wrapping
his hair turban style and tapping his thigh to get up.
He sat with Vicky as she took a round brush, running it through his hair
as she he watched her work in the mirror. It didn't take too long as,
with the snipping from the previous night, as she created a part on the
left and he saw the front hanging only chin length. As she brushed
through them, sweeping them across his eyes, he got his first real view
of himself in long side bangs, realizing she had trimmed off quite a bit
of his length in front. She wasted no time sliding her flat iron back and
forth and then quickly surprised him, walking behind him with a long
"You looked so pretty with the long full curls last night," said Vicky,
quickly snapping in the weft. "Let me just see how it looks long and
sleek on you."
After two more wefts, she brushed and flat ironed as she was satisfied
with her work and he found himself in a long sleek straight style now. It
was simple, but trendy with long straight angles framing his face and the
long side bangs he had now blended perfectly into the pin straight style.
"So natural, right," said Vicky, running her fingers through it and then
brushing at his lips "Just a little extra lip butter and some gloss, ok?
It's a bitter cold morning, and your lips are a little dried out today
for whatever reason. Enjoy the slopes, and I'll see you later, hon."
He got up and knew the drill, heading into the dressing room and putting
on his ski clothes. This time he saw hot pink Columbia stretch pants and
this time his top was lavender with matching hot pink sides. He slipped
into his furry boots, tucked his hair under his headband, slipping into
the winter white form fitting Spyder jacket. He zipped up and slid on his
hot pink mittens as he wasted no time heading down to the slopes.
He looked around, not seeing them and then went inside getting his gear.
He changed into his ski boots and came back out, looking around before
glancing at the time on his phone.
"Where are you guys?" texted Mike, pulling off his mittens.
"In the gondola on my way to the top," texted Lisa. "Check your
voicemail. I called you twice and waited for you. but you didn't answer.
I figured you were blowing me off anyway when you didn't answer. I could
use a little time to think .so let's talk later."
Mike felt terrible. calling her a few times now but her phone went right
to voicemail. He texted a few more to no avail as he put down his ski's
and went inside. getting some coffee. He sat in the lodge. taking off his
coat. daydreaming about what had happened and tried a few more times
calling. He began a text message, telling her how much he cared for her
and how important she was to him, when suddenly he was startled as some
sat right next to him.
"What's happening, Monique?"
"Oh hey, Tyler," said Mike surprised.
"You heading out there, girl. The conditions are unbelievable today,"
said Tyler, all pumped up to ski.
"Yeah pretty soon," said Mike, moving his phone and hiding his message.
"Sorry, did I interrupt something?" asked Tyler. "Those things work like
crap here anyway. Plus, forget all that texting you girls do, and get out
there! Who are you texting, you're boyfriend?"
"I don't have a boyfriend," said Mike, annoyed. "Didn't we cover that
"Let's hit the powder. Come on, I'd love to ride a trail with you?" said
"Sorry, that's a fantastic offer, and I'd love to, but I'm waiting for my
friends," said Mike, blowing him off.
"You sure," said Tyler disappointed. "I'm only here with my friend Sam,
and we could show you some really great trails."
"Oh, she's so rude my friend, isn't she?" said Lisa, surprising them and
interrupting. "Hi, I'm Lisa."
"Hey, I'm Tyler," said Tyler happily.
"Oh, hey Lisa. I was desperately trying to get you, I've been waiting for
you," said Mike, handing her his phone. "See, I was working on sending
"Ah, dead as a doornail, Monique," said Lisa, hitting a few buttons and
showing him. "I did see the missed calls once I got near the base and had
"Shit, I forgot to charge it last night," said Mike, shaking it.
"Yeah, you forgot a lot of things last night didn't you?" said Lisa as
she patted Tyler. "You have to excuse her Tyler, she has her blonde
moments you know."
"I'm cool with that." Tyler nodded. "So why don't you join us for some
runs? Maybe Monique would join us now if you come as well. We know this
place inside out. Come on, it'll be a blast. The big chairs are quads, so
"Really?" said Lisa, swishing her cheeks, trying to act cute and
"We couldn't leave Beth and Ginny," said Mike, trying to backpedal. "They
aren't advanced enough for those double diamonds anyway."
"No, that's true, but they just went snowboarding, so sure what the
hell," said Lisa, giving Mike an evil look. "How could we turn down
skiing with two cute guys?"
"Awesome," said Tyler, loving her comment. "Let's do it then!"