Neither Sarah nor I spoke of "The Agreement" the next day. However, the following evening Sarah poured us both a glass of red wine and after a few sips said, "So.... Are we going to discuss this anytime soon?" I could tell by the playful enthusiasm in her voice she was definitely interested in talking and quite possibly following through.
"Sure," I said in response. "I have some concerns we should definitely talk about and I want to know what you're thinking, too."
"Well," Sarah began. "Being a registered nurse I'm very aware of all of the health risks involved and we have to make absolutely sure we don't bring anything but memories home with us. That's my biggest concern. What about you?"
"I agree with that, of course. But from a purely practical standpoint, I have a really huge issue I'm not sure we can overcome," I said rather matter of factly.
Sarah looked almost crestfallen as she quietly asked me, "What kind of issue? What could be so important we can't do this? Are you afraid we won't love each other if we follow through?"
"No, not really," I told her. "I mean, that's certainly something we need to discuss because we've both been completely committed to one another and 100% faithful." I turned to look at her as I added, "Right?"
"No! I mean 'yes'. Well, I can only speak for myself but I can assure there's never been anyone else. Ever. You?"
"No, no one, honey. Ever. My concern is a practical one and it involves being able to 'pass' in public. I know this is all new to you. Hell, I don't even understand it all yet by any means. But 'passing' is the word people use to indicate how successful a crossdresser is in public. Can he, can she pull it off without being 'read' or 'clocked' which basically means being discovered."
"But you look stunning in women's clothes, Cal. In fact, I'm still a little bit jealous about you looking better than me," she said playfully. "I was totally blown away when I saw you and I couldn't find a flaw anywhere. And trust me, I notice stuff like that. So what is it that has you so concerned?"
"My voice. I've practiced trying to talk like a woman but well, not seriously because I never thought I'd actually need to talk like a woman. Convincingly so, that is. It's really hard and quite frankly it has me worried I won't be able to pull this off with you and your date. I mean, I'll have to date guys who know not just about me but who you are, too. You, on the other hand, can't ever tell your dates who I am. So unless I can learn to talk like a woman enough to pull this off, I don't see how we ever double date."
"Let me hear you."
"What? Right now? Right here?"
"Yes! Right here, right now. Be a girl for me."
Sarah's tone was playful and encouraging but I still let her know I was a little embarrassed to try this in front of her just out of the blue.
She said, "Let me get this straight. You fantasize about dressing up like a woman and having sex with a man, but you're afraid to talk to me in your best girly voice? Really, Cal? Really?"
"Okay. I'll try. But don't laugh, all right?"
Sarah nodded and I cleared my throat. I began by quietly croaking, "Hi. My name's Callie and I love wearing women's clothes."
Sarah burst out laughing then put her hands over her mouth as she said, "Oh, honey. I'm so sorry. I just couldn't help it. It was so unnatural and well, kind of weird."
I was only minimally embarrassed as I told her, "See. I told you I need a lot of work. In fact, I think I need some professional help."
"Not to be mean but I agree. What kind of help? What do you have in mind? What sort of help is even available?"
"I need a voice coach. I've been doing some on-line research and there's a voice coach/therapist in Falls Church who helps men who are transitioning to become women—don't worry, that's not me. I'm not a transsexual, I just...."
"I understand and I never once thought that was the case. So when can you start? Soon I hope," she teased. The wine was affecting her and she was becoming more playful. She was nibbling around my ear and her free hand was beginning to wander. "I'm not sure how much longer I can wait for strange cock," she said as she stroked mine.
"Ummm," I murmured. "Will I be good enough for now?" I queried as I turned to kiss her.
Sarah buried her tongue in my mouth as she managed to whisper, "More than enough—for now."
We undressed each other and I fucked her hard after spending a lot of time on her nipples and eating her pussy which was something she loved as much if not more than sex itself. I loved that she still shaved "down there" and when I came up for air I felt her cum for the first time as I said quietly, "Mmmm. Some guy is gonna be very happy to fuck your sweet, bald pussy, Sarah. Maybe several guys." I brought her to orgasm again a few minutes later with my cock and we lay there for a while just holding one another. Both of us were wondering whether or not this might be the last time we made love in an exclusive relationship and what the future might hold for our marriage.
I called the therapist's office during my lunch break the next day. To my pleasant surprise the receptionist was completely accepting and assured me this was so routine I need not give it a second thought. She also told me that the therapist, Dr. Lisa Turner, had had tremendous success as a voice coach. While counselling transitioning women with issues other than voice was the primary part of her practice, working on voice made up about 20% of her caseload. I set up two sessions for the week—Tuesday and Thursday at 6pm. I called Sarah at the hospital and shared the good news with her.
"Mmmm. That's exciting, Cal! Any idea how many sessions you might need?" she asked.
"Well, the receptionist said it all depends on how 'coachable' the patient is. Some 'get it' right away and others never learn how to do it." Before Sarah could voice her disappointment I let her know that 100% of Dr. Turner's patients show improvement anywhere from a low of 20% to a high of 95%.
"So....Let me ask you this. Would you like to go dressed up as a woman?"
I became instantly hard and checked to make sure no one could see the growing bulge in my khaki-colored Dockers. "I'd love that. Are you sure that'd be okay?"
"I'm very sure. I want you to be as comfortable as possible so you can make as much progress as you can in the shortest amount of time. There are so many good looking men out there just waiting to fuck hot looking women like us," she teased.
"Jesus, Sarah. You're gonna make me cum in my pants again. Enough already. For now, anyway. So see you tonight?"
"Indeed you will...Callie. Bye pretty girl."
I had to think about something else—anything else—and right now. Work. That did it. The new F-18 Super Hornet modifications we'd contracted to complete. That took care of Mr. Woody for the time being.
Unlike our military counterparts, we civilian contractors couldn't be made to work overtime without advance notice and being paid time and a half. I loved my job and was always looking for overtime so when I occasionally asked for time off, no one said anything about it. Active duty military guys could just ask their boss for an hour even a half day off and could get it without taking leave. The down side was having to submit a leave request to get any time off at all. It was a very small downside though, as I had all kinds of time off saved up. I requested to leave at 2:30 both Tuesday and Thursday which was approved without question. I'd need 30 minutes to get home, about 90 minutes to get ready, and an hour in DC traffic to get to the therapist's office.
I got home right at three o'clock on Tuesday and headed straight for the bedroom to undress, shower, and shave. I intentionally didn't shave that morning to make sure I wouldn't cut my face from shaving so closely twice in one day. On days when I dressed up, I had to shave extremely close with a Mach-4 razor with a brand new blade, even with my relatively light beard.
As I walked into the bedroom, I began unbuttoning my shirt when I noticed a large blue box on the bed wrapped with a wide, white ribbon. I tore off my shirt, threw it in the hamper, and picked up the box. I opened the card inside and read, "I hope these are the right size and I hope you like them. They're definitely your style. J Have a wonderful first session, Callie. Love, Sarah."
I lifted off the top of the box and set it aside. I pushed back the white paper that lay on top and saw a beautiful navy blue colored knit dress inside. I picked it up and put it front of me in front of the full-length mirror and admired it. It had spaghetti straps and matching dark blue lace around the top. It fell to about four inches above my knees which was perfect to be both sexy and appropriately modest. I set it carefully on the bed then noticed there was also a matching cardigan inside. I was thrilled my new outfit which I would wear with a pair of 3-inch black strappy heels.
In an hour and a half, I was ready. I slipped into my new dress, stepped into my shoes and ventured a first look in the mirror. No matter how often I saw myself when dressed up, I was still absolutely amazed at the transformation. It made me weak in the knees and hard somewhere a little higher up every time. I'd learned how critical the eyes are and paid careful attention to blending the right shades of shadow, using the right shade of liner, and ensuring the eyebrows were perfect. I was satisfied with my makeup and dress. All I need were the right accessories. I chose a beautiful brushed-nickel necklace and matching earrings as well as an elegant looking silver-colored watch to complete the look. I was ready to go so I picked up my purse and sweater (if felt so amazingly good to be able to say my purse and my sweater) and headed out the door.
I loved the click of my heels on the concrete floor in the garage. I opened the door, sat my things inside, then sat in the seat and remembered to lift my legs together and turn them at the same time the way any woman in a dress or skirt would do. I still found it hard to grab things with long fingernails but I was determined to master that because going without nails was simply unacceptable!
I got the office a few minutes early. As I pushed open the door, I noticed three people in the waiting room. Without staring, I noticed two women and one man who was sitting next to the more attractive female. The other woman was clearly a transsexual and my heart went out to her as she was anything but passable. My first thought was of a lumberjack in women's clothes. I also couldn't help but admire her courage knowing that she knew she didn't pass. I forced my mind to switch subjects and noticed the other woman was much more attractive although most likely a male-to-female (MTF) transsexual. The man sitting next to her was very good looking and I instinctively smiled at him when he made eye contact with me. I was clearly flustered but held myself together as the receptionist said, "Hi! You must be Callie. I love your dress. It's so pretty!"
I thanked her and was immediately aware of why I was there. I sounded like the lumberjack in a dress. Well, not that bad but I needed real help. The receptionist's name was Donna and she said she needed me to fill out several forms and to just have a seat until I was done. I took the clipboard and paperwork and sat down across from the woman and the cute guy.
"Hi," she said. "I'm Alicia. I haven't seen you here before."
"I'm Callie," I said quietly. "This is my first visit. I'm here for voice therapy which is probably rather obvious now that I've said something," I explained.
"Me, too!" Alicia shared. "I've gotten other counseling for HRT which is hormone replacement therapy but today is my tenth voice session. I'm hoping it will be my last. I've worked very hard at it but it's just so difficult."
"You sound very feminine to me," I said knowing that wasn't exactly true. Had I met Alicia elsewhere I might have thought she just had a very deep voice. She was what I would call attractive "enough" and her voice was feminine "enough" to get by. I was sure that she, unlike the other woman, would have no real difficultly living full-time as a female. It was then I heard the other woman respond to her name being called and I cringed when her voice sounded exactly like a male baritone say, "Yes, that's me."
Alicia shared my discomfort and told me, "That's Carrie. She told me she doesn't care if she passes. She just needed her body to match her brain. She waited until she was 48 to transition and she said she was nearly suicidal before she finally said enough is enough. Her wife divorced her, her kids don't want to see her, and yet she says she's never been happier. I can totally relate to the need to make things match up. But for me personally, not passing to that degree just wouldn't work. I really want to become a woman in every way and being accepted as one is very important to me."
I told her I thought she was very pretty and that her voice was coming along quite nicely when she asked me, "Speaking of passing, you look amazing! So are you pre-op or post-op? Let me guess! You're already post-op, right? If not, then you've been on hormones for at least a year now. Am I close?"
I looked down then back up at her and simply said, "Oh, I'm not a transsexual. I'm just a...well, I mean I'm only a crossdresser who just wants to look and sound like a woman as much as possible. I'm not actually transitioning. Is that offensive to you by any chance? I mean, I hope I'm not trivializing something that's obviously so important to you."
Alicia looked at the man next to her then back at me. "Are you serious? I hate you! I've been at this for 18 months and I'd die to look like you! And yes, of course, that's okay. We only get one life and as they say 'we pays our money and we takes our chances', right?"
I was pretty sure she was being sincere (or I at least hoped she was.) "Well, thank you. That's very kind. You should know you look very much like a woman yourself. I hope you know that. Now I'm rambling. I'm sorry. I'm new to all this so I'm not sure if I'm even making any sense."
"Of course you are, Callie. It's just that you look better than any TS I've ever met pre- or post-op and you're just well, 'playing.' Oh, sorry. That didn't sound right. I mean for we TS types, this is who we are 24/7 and we'd give anything to look like you and you're not even taking female hormones. Did I mention I hate you?"
Alicia smiled and said, "Oh, shame on me. I have this tendency to get chatty and I forgot to introduce you to my brother. Callie, this is my baby brother, Michael. We're fraternal twins, but I'm two minutes older and I never let him forget. We've been best friends all of our lives. Even so, I was really afraid my need to transition might harm or even destroy our friendship but he's been my best and often only true friend." Alicia then put a hand near her mouth as though she telling a secret and whispered, "He also told me he thinks you're cute."
I could feel that familiar stirring "down there" and felt myself flush wondering if he knew how good looking I thought he was. All I could manage to say was, "Hi, Michael."
"Hi back," Michael said smiling. "It's a pleasure to meet you and I'm going to kill Alicia for telling you that. So much for being supportive being a two-way street. Thanks, Sis!"
I loved the playful banter between them and could tell there was a real connection there. I was fascinated by the whole thing and let them know I had a hundred questions and hoped we might be able to get together at some point just to talk and share our experiences. Alicia chimed in saying, "Oh, I'm sure Michael would like that, Callie. In fact, knowing him as I do, I'm betting he'll give you his number before we leave."
Michael just smiled. "I won't deny that's a distinct possibility, but I'd actually rather have Callie's number. That way I know I'll get to talk to her again. I mean to answer her questions, of course."
"Oh, I'm not sure that's such a good idea," I said softly. "I'm sort of in a relationship and..."
"I understand," Michael said. "That's definitely understandable. He's a very lucky man."
I was caught off guard I found myself speechless just as I heard my name called. As I stood up, I heard Michael say, "Here, Callie. This card has my number and email address. You know, just in case you want to talk sometime. I can probably get Alicia to chaperone if you'd like."
I nervously took his card, thanked him, and wished Alicia all the best as I followed the receptionist to Dr. Turner's office.
The next 45 minutes flew by as I found myself alternating between focusing all of my attention on the techniques I was shown and imagining myself in Michael's arms. Would Sarah approve of him? Did that even matter? Who might she choose? Had she already chosen him? Was she just waiting for me to announce which sexy doctor she would be giving herself to?
As I left, I removed Michael's card from my purse and looked at it carefully. Michael D. Johnson, Attorney at Law. I took note of the firm's name and committed his phone number and email address to memory.
I practiced my voice techniques all the way home and by the time I arrived my vocal chords hurt from trying to "raise them up" over and over again. Dr. Turner told me it would like using a new muscle and that some discomfort would follow. She'd stressed the importance of not ever talking in a falsetto voice. Instead, I had to concentrate on making my own natural voice sound higher and more feminine. I was pleasantly surprised at the progress I'd made and was really looking forward to Thursday's session. And to my next contact with Michael.
I paused for a moment to reflect on the changes the last year had brought. Yesterday was our fifth anniversary in which my wife surprised me with a complete shift in attitude we came to call "the agreement." It was preceded by an arrangement we'd come to one year previously. We simply called it "the deal."
I'm now 32 and my former wife Sarah (not her real name for obvious reasons) is 30. We divorced a year ago partly because of crossdressing but most for other reasons. This story takes place five years ago when we were 27 and 25, respectively.
We married the day I graduated from college while she was still a senior in the University of Virginia's nursing program. I've worked as an aeronautical engineer on a nearby Navy base since, and between the two of us we make an excellent income.
Like most men who crossdress, I didn't tell Sarah my most deeply-held secret until after we were married. Like those other men, I too believed getting married would "cure" me; that I'd lose interest in it once I had a wife. The fact that she preferred wearing the kind of clothes I preferred to wear when dressed up allowed me to superficially convince myself that would serve as an adequate substitute and keep me on "the straight and narrow." For the six months before the wedding until about six months after, it had.
Just over a year ago, on a Saturday evening when she was working swing shift, "the urge" returned with a vengeance. I'd gotten rid of all my female things, something known as "purging" in the crossdressing community "knowing" I'd never need them again. As I looked through Sarah's things to select my outfit, I was as careful as I could be not to either stretch out any of her clothes or to get makeup on them. I knew I was taking a risk, but I couldn't stop myself from spending the evening as Callie. I'm a small man. I stand 5'8" and at the time weighed 150lbs. Sarah is an inch shorter than me and there's no chance I'll give her weight—now or ever. (Suffice it to say she weighed considerably less than me.)
Even without a wig and with hairy arms, legs, and chest (mine was light but noticeable as I hadn't shaved them in years), I found myself flooded with the endorphin rush that always came from dressing up like a woman. I reveled in every aspect of the experience the way I always had from choosing what to wear to the careful application of my makeup to accessorizing. I preferred a classy, semi-professional look and I have what might be termed a fetish for certain kinds of sweaters paired with shorter skirts, heels, and expensive jewelry. While the sweater thing may seem odd, it's actually pretty logical as I grew up in northern Virginia where it's cold much of the year. Girls and women wore sweaters a lot and I have always liked the dressier, more form fitting type. The thicker, baggier, "granny" variety does nothing for me. Don't get me wrong. I also love nice dresses, blouses, lingerie, and even jeans. It's just that a sexy sweater is my all-time favorite.
My "first" session ended all too soon with a call to a phone-sex line that specialized in crossdressing men and very near wardrobe miss as I came with a ferocity I hadn't experienced in a very long time. Callie was back and I was sure Sarah would never understand. I had no idea how to address this with her, but I knew Callie wasn't going to be able to stay in the closet any longer.
I could tell something was bothering Sarah as she got dressed for work the next day. She seemed puzzled after looking at her neatly-stacked sweaters in the closet. I'd put things back as carefully as I could, but women can just sense when things are out of place. Even worse, she was visibly upset after grabbing her bra and panties from the dresser door. She didn't say a word, however, and I didn't ask as I knew she suspected something. I was grateful for what was likely only a reprieve no matter how short-lived it might be.
Less than two weeks later, I was enjoying another evening as Callie when Sarah came home unexpectedly from work. I was in the master bathroom and had just finished removing all of my makeup. I was toweling off when looked up and saw her. Her favorite white sweater and black skirt were on the bed and a pair of three-inch black heels were on the floor by the bed.
"Who is she!?" Sarah demanded. "Who are you sleeping with, Cal?"
I saw tears fall from her eyes and I sat down on the bed and said quietly without looking at her, "No one, honey. There's no one else."
She picked up the shoes and said, "If it was just my skirt and sweater that would be bad enough knowing you let some other woman wear my clothes," she said as she picked up the shoes. "But THESE are someone else's. THESE are not MY shoes! Don't lie to me. Who was here with you tonight and how could you let her wear MY things???"
I looked up at her, took a deep breath and told her, "Sarah, those are mine. The shoes belong to me."
Stunned, Sarah dropped them on the floor and said, "What are you talking about? How can they by YOUR shoes, Cal? What would you be doing with women's shoes? I might be able to forgive a one-time affair, but if you lie to me, we're done. Now I want the truth. No more lies. No more BS. I want the truth! Who IS she???"
For the next ten minutes, I explained my lengthy obsession with crossdressing. I told her how much I'd hoped it was over when I met her and that I honestly believed it was all behind me. I explained the sudden, overwhelming return of these urges and that I felt powerless to stop. I felt both a deep sense of shame and relief that this was finally out in the open no matter how Sarah might react. I was shocked by her response.
"That's it? YOU wear my things? Jesus, Cal. I thought you were having an affair. I've been jealous of Erin (an attractive co-worker at my firm) for as long as I can remember and I immediately assumed it was her. I mean, I've seen how she looks at you and the way she laughs at everything you say. Trust me, you're not that funny," she said half-jokingly.
Sarah sat silently at the foot of the bed for what seemed like a very long time. Finally, she turned to me and said, "This I can deal with—I think. I mean, I might be able to handle it. I just don't know. I'm just so relieved you're not having an affair that maybe I'm being overly optimistic about this. All I can say is we can try it for a while and see how it goes. I'll need some time to process all of this. Just tell me again there's no other woman, okay?"
I assured her there was not and there never would be. I told her how much I loved her and that she meant everything to me and that no other woman could even compete with her.
Sarah suddenly burst out laughing! "I KNEW something was going on! My bras were stretched out and my sweaters weren't folded right. I thought I was going crazy and then I started to suspect another woman. Then I come home and see my things on the bed and these other shoes on the floor and I was sure you were cheating on me." She laughed some more. "Now I know why you've always been so interested in what I wear and why you buy me so many clothes and so much jewelry. Those are things YOU'D like to be wearing, aren't they, Cal?"
For the first time since I was 14, I blushed. "Yes," was all I could manage to say.
Sarah sat down beside me, leaned her head on my shoulder then took my hand. "I love you, Cal. I don't care what you wear—in private. I don't think I want to see this—at least for now--all that really matters is you love me. You're not much bigger than me which explains why the changes I noticed in my clothes were so subtle. I don't like the idea of you wearing them so really need to get your own things as soon as possible. Deal?"
"Deal," I said as I turned toward to see if she meant what she was saying. I could tell from her eyes she did. "Thank you, honey." I said sincerely as I sat next to her.
Sarah took my hand and kissed me and said, "No, thank you. Thank you for loving me and for being honest enough to tell me this. I can't imagine how difficult that must have been. Now let's put this stuff away and get ready for bed. And no, you may NOT wear one of my nighties to bed," she teased playfully.
That was the "deal." I could buy my own women's clothes and wear them when she wasn't around. I also managed to convince her to let me shave my body hair and grow my hair longer. The "agreement" was still a year away and it came after a seesaw ride of ups and downs with my crossdressing which I'd kept private and away from Sarah as we agreed. She had no problem with me shaving my body hair or growing my own hair longer. After almost a year of nothing but trimming the ends, it was now almost shoulder length and I wore it in a thick pony tail at work. Sarah actually liked my hair long. She simply had no interest in seeing me let alone being with me while en femme. It was a subject we rarely discussed and as my interest in crossdressing drew stronger by the day, avoiding it was becoming the proverbial 800lb gorilla in the room. Other than that tension, everything else seemed pretty much as it had been. Our sex life was good and we had a weekly date night we rarely ever missed. Still, I found myself wanting so much more and those new desires were becoming unbearable. One of those was the need to be seen in public. I desperately wanted to be able to go somewhere as Callie. Anywhere. And yet, another part of me had even more specific desires. Each time I took Sarah out dancing, I found myself wishing I could be there as Callie being asked to dance by the good looking men I could no longer ignore.
I tend to be obsessive and detail-oriented to the point of being anal. In fact, that's a word I hear rather often at work as I spend inordinate amounts of time ensuring my projects are as close to perfect as possible. I applied this trait to crossdressing and found myself constantly reading and researching areas like hair, makeup, accessorizing, and fashion. Makeup application was clearly the biggest challenge to actually looking like a woman and the progress I'd made was phenomenal.
In addition to growing my hair long, I'd also lost quite a bit of weight. I was down to 135lbs due to careful dieting and the distance running I so enjoyed. As I said, my body hair is light and that's especially true on my face. I'd heard a number of times from women over the years that I had "those eyes" meaning the kind that are framed by long lashes which look like a girl's. It was one of things Sarah most liked about me along with a perfect smile courtesy of the braces I'd once worn and along with my small size, the thing that made it possible for me to actually look like a women in drag.
Other than my increasing dissatisfaction with only being out of the closet, I made time for Callie as often as possible. It's amazing how quickly we take new things for granted and want more. Buy a new car and you think you'll be excited to drive it every day forever. Nope. Just a few months later and it's no big deal. Getting the okay to dress up from my wife was a dream for the first six months. Then I wanted more. Now the frustration was building and I had no idea how to "earn" more privileges without blowing up "the deal." That's when chance or fate or whatever intervened.
A week ago, Sarah and I got our wires crossed. I was under the impression she was working until midnight that Saturday, and I'd made plans to spend the afternoon and evening as Callie. After finishing all of my detailed preparations which took just short of two hours, I was utterly amazed at the beautiful woman looking back at me in the mirror. I'd had my long, dark-brown hair up in rollers for three hours after coming home from a total body wax and a long, warm bubble bath and cleansing shower. My makeup was as good as I'd ever seen it. The eyebrow template I'd designed allowed me to have perfectly shaped brows which framed my green eyes which were highlighted with dark-brown liner and a smoky-grey eye shadow. The false eyelashes were further thickened with just the right amount of mascara and the soft, cinnamon-colored blush sat on top of a perfectly blended liquid foundation which was all covered with loose powder. My long hair cascaded down my face and curled gently around it. I wore it shoulder length and curled it under at the bottom. Soft, wispy bangs fell from one side to just above my right eyebrow.
For my outfit, I'd selected a black, long-sleeved, rib-knit sweater with a jewel neckline and a moderately short goldish-tan skirt with a skinny black belt. I'd long ago ordered a computer-designed undergarment which gave me just the right amount of curves and a nice round tushy. I was wearing an expensive gold and black necklace with matching earrings and bracelet. I applied my own French nails which I'd painted to match my dark red lipstick. Silky suntan stockings and three-inch heels which matched my skirt and purse completed the look.
I was busy making dinner and with some light jazz coming from the stereo, I didn't hear either the garage door or Sarah enter the house around 8 o'clock. I'd poured myself a glass of merlot and as I set the bottle back in its place, I sensed motion behind me and to my left. I looked up and noticed Sarah, still in her scrubs, standing about ten feet away. My heart stopped and I froze in place not knowing what to say. In an instant I realized this was a make or break opportunity. I understood this was the way fate had chosen to present me with the chance to either take my love of crossdressing to the next level or possibly to divorce court. Instinctively, I knew Sarah's reaction would determine the path.
Sarah stood there motionless and just stared. Without saying a single word her eyes moved up and down several times taking in what she saw. "Oh—my—God," she said in a staccato voice. "So this is what you look like. Oh—my—God."
I started to speak when she said, "I don't want to discuss this now. I just need time to think. I'm not mad. I'm just confused. And shocked. I got off early and I was so exhausted I didn't think to call and warn you. I should have known but... Oh—my—God, Cal! You're absolutely, unbelievably beautiful." With that, she walked past me, picked up the wine bottle and poured herself a very large glass while I headed to the bathroom to remove all of my carefully applied makeup and turn back into drab old Cal.
Sarah said she didn't want to discuss this so I gave her her space. Our fifth anniversary was just two days away and my head was spinning with worries over how what Sarah had just seen might affect our marriage. I was also cautiously filled with hope that we might even reach our own version of FDR's "New Deal."
We went to bed a couple of hours later and neither of us spoke. In fact, Sarah barely said two words to me the entire next day which was Sunday. Tomorrow was our anniversary and I'd made reservations at her favorite restaurant. I'd also bought her a beautiful pearl necklace and matching earrings I hoped might soften the blow. I assumed I'd find out soon. That is, if Sarah was ever going to talk to me again.
Other than asking what time our reservations were for, Sarah still hadn't said much of anything to me (she was off all day and this was also a Monday/federal holiday so I was home, too) and that only increased my level of concern which was now bordering on paranoia. The one thing that served to calm my fears was that Sarah was wearing my favorite outfit—a white, long sleeved sweater, a short black skirt, four-inch black heels, and a beautiful necklace with matching earrings. She had always been good about indulging my clothing fantasies so I didn't read too much into it. My hope was we'd at least have a pleasant dinner and great sex later that night. My fear was hearing Sarah tell me she's not in love with a "woman" and that she wants a divorce. With all those thoughts swirling around in my mind, we arrived at the restaurant right on time after a short, quiet ride through moderate traffic.
An attractive young blonde seated us and told us our server would be with us shortly. In less than 30 seconds, a good-looking young man in a white shirt and black pants told us his name was Ken and asked for our drink order and if we'd like an appetizer. I ordered a bottle of expensive champagne as Ken thanked before leaving to take care of our order. As I turned toward Sarah, she slipped a Hallmark card out her purse and onto the table. She pushed it toward me and said warmly with the first smile I'd seen in days, "Happy anniversary, honey. I love you."
Before opening it, I reached into my jacket pocket and removed her gift and card, slid it closer to her and said equally warmly, "Sarah. I love you, too. Happy anniversary. I just want to apologize for the other...."
"Shhh," she said holding her index finger over her mouth. "It's okay. I'm not upset. Open your card."
"No, you first, honey," I told her.
"No, not this year. I want you to read what I wrote. So you first."
Love and warmth radiated from her eyes and face and yet it did little to quell the mishmash of thoughts in my head which had just turned into a veritable firestorm. She wants me to read what she wrote? What might that be? Is Callie being sent back to the closet? Is this the end of our marriage? Those and a dozen other questions took turns filling my cerebral processing unit as I opened the card and removed the contents. Inside of the card itself was a two-page, hand-written letter.
"Read my note first, okay?" Sarah asked again.
I unfolded it and began reading. "Dearest Cal. The last five years of my life have been the happiest. I love you so, so much. You've always been there for me. You've supported me and my career no matter how many long, crazy hours I've had to work. You've never once gotten upset with me or even raised your voice. In fact, you've spoiled me rotten and I don't take any of this for granted. Thank you and I love you. Now for the hard part." My paranoia gland filled with fresh blood as I glanced up at Sarah to see if her facial expression might reveal any clues. She was still smiling as she nodded to indicate I should keep reading.
"I've tolerated your 'special interest' for over a year now. I told you I didn't want to see you dressed 'that way' and that seemed to working well for both of us until Saturday. Let me just say that when I walked in on you, I was so completely stunned by what I saw, I found myself at a total loss for words. Page 2. The emotion I felt most strongly surprised me. I wasn't angry or even upset. I knew this was what you enjoyed doing. What blew me away was how much you actually looked like a real woman. I kept looking and staring to find some flaw like an Adam's apple or big hands or anything and all I could see was a beautiful woman looking at me. What bothered me the most was all I could think of was that you looked prettier than me. I was so, so—jealous! I was upset. I felt hurt. I kept looking to find some clue you were a man but I couldn't find one. Your hair was beautiful. Your makeup was perfect. Your outfit was amazing and even your "boobs" and butt looked real! I was tired and sad and needed time to think. Well, I've done nothing but think for two days straight. In fact, I was awake all night thinking about what I wanted to say and how to say it. So here goes."
Again I looked at my wife as I imagined the other shoe dropping in the last few lines of this two-page, hand-written note." I continued reading.
"Cal, do you ever think about having sex with men when you're dressed up? I promise I won't be upset no matter what you say. Just please, please be completely honest with me and know that I love you. Happy fifth anniversary. I can't wait for number ten. Love, Sarah."
My heart was pounding so hard I was sure everyone could hear it over the background noise at the bar which was nearby. I felt panicked and excited at the same time because these relatively new feelings of fantasizing about being kissed by an attractive man. I wasn't homophobic, but the thought of being with a man while in drab was well, disgusting. But when I was a "woman", it seemed so natural that it had to be right. Did Sarah know? If so, how could she? If I told her, would it ruin our marriage? Would she think I was gay?
I sat there looking down at the table for a full minute before I finally managed to croak out a soft, "Yes. Sometimes. When I'm dressed up that is. But only then," I quickly added. I could feel the blood rushing to my cheeks again and felt powerless to stop it. I forced myself to look at her expecting to find her eyes filled with tears or get up to leave.
Instead, she reached out her hand and told me, "It's okay. I thought that might be the case and...." Just then Ken back to take our dinner orders and we made small talk with him. As he walked away, Sarah continued by saying, "Cal. I can only imagine how afraid you feel right now wondering how I'd react. But I'm the one who's really afraid because...well, because of what I want to say right now."
"Sarah, honey. Please don't be afraid. You can tell me anything. Nothing will ever make me stop loving you. Just tell me how you feel so we can work through this."
Sarah looked down into her lap then raised her head and looked at me. She said, "I hope you can understand this but if not, please don't hate me for saying it, okay? This doesn't mean I don't love you, Cal. I just—I find myself fantasizing and well, I want to be with other men, too." Before I could respond she hastened to add, "That doesn't mean I don't love you with all my heart. I just can't get the thought of us double dating out of my head. Having two good-looking men take us out to dinner and then out dancing and then.... Watching your date hold you and kiss you and knowing you're completely okay with mine doing that to me, too. Is that crazy? Am I crazy? Are you angry with me?"
I sat in silence taking in every word and couldn't help notice my cock growing harder than it had ever been in my life. I replayed the conversation again to make sure I hadn't misheard and just as I began to speak, Sarah said, "Cal, please talk to me. Please tell me you still love me. Please." This time, I actually did see a tear forming in her eye. First one, then the other. My silence was killing her.
"Sarah, of course I still love you. I will always love you. And no, I don't think there's anything wrong with that at all. In fact, I'm quite literally ready to cum in my pants just thinking about it. Are you sure this is what you really want?"
Sarah's tears fell as I spoke and then she dabbed her eyes with the linen tablecloth. As my acceptance washed away her tears, her eyes brightened and a smile spread across her face. "I'm very sure, sweetheart. I've never been more sure of anything in my life except for the decision to marry you. Are you okay with this, honey? I mean really okay with it?"
"I am," I reassured her. "I am more than okay with it. If I was religious, I'd say ths is some kind of answer to prayer or something. I couldn't be happier to hear you say that." I then cautiously explained how my own interest in men had snuck up on me. Subtly at first then more intense. I told Sarah my alter ego needed to get out of the house.
Sarah paused for a moment then asked me, "What do you call yourself when you're all dressed up? Does she have a name?"
"Callie," I told her. "I chose the name of Callie. Is that okay?"
"Of course it's okay," she assured me. "In fact, it suits you. Not just because it's your male name with a female ending but because it's so logical. I'm not sure how good of a woman you'll make but if you think anything like you look, I'm sure you'll do just fine."
I took her hand and indicated I wanted her to sit next to me and by looking down into my own lap, she understood why I couldn't be the one to get up and move. She gracefully moved around the corner of the table and slid in beside me. I turned toward her and kissed her softly on the lips and whispered, "Happy anniversary, sweetheart. I love you so much."
"Happy anniversary, honey. I love you, too."
Sarah just had time to open her gift before our first course arrived. She was thrilled with the pearls and asked me take off her necklace even as she removed her earrings. I did so and replaced it with the new strand of very expensive pearls while she put in the new matching earrings. "They're beautiful, honey. Thank you. Now we just need to get your ears pierced so I can buy you a pair of your own," she teased. Sarah's hand slid over my pants and she gently stroked my cock as we kissed again. Our tongues met briefly and only then did I realize that I was filling my underwear with hot, sticky cum. Sarah felt me shudder even as I struggled hard to suppress it. She smiled wickedly as Ken approached with our first course and whispered to me, "Okay, who gets fucked by Ken first, Callie. You or me?"
I excused myself to get to the bathroom before the liquid soaked completely through. I felt dizzy and lightheaded as I stumbled toward the room with the big "MEN" sign on it. As I tried to take everything in that just happened, the one thought that took center stage was how the next time we went out I might be choosing the door that said "WOMEN" on it. I could already feel myself getting hard again. My God how I loved her!
In the next segment, Sarah and Callie go on their first double date.