. . . This realization made me quietly buoyant. It freed me from the transvestite prison of being my clothes, and opened more attractive options for defining my personality

. . . Everyone could see me changing but me, and I was having so much fun I was blind.

. . . I, of course, was clueless, perhaps willfully so, about her feelings, just as I had been clueless about my increasingly femme image.

By lunchtime Monday, it was as if the previous week had never existed. We were back on the work treadmill, beginning with our standard Monday morning staff meeting. We caught up on old business, made sure everyone was keeping up with their assignments, solved problems and discussed approaches to a new account we were pursuing. During the day on Monday, it never even entered my consciousness that my toe nails were painted. I only realized it that night, when I took off my socks. I must admit that I delightedly wiggled my toes at myself, but that’s as far as it went. And the rest of the week just flew by the same way, even though I was mostly at home. Because Rebecca had been so generous with me last weekend, I made sure I was in total guy mode when she arrived home each evening. And it paid off. She was relaxed, warm, and very attentive and joyful in bed.

I didn't expect to see Phillip for at least two weeks because he told me he was off on a west coast swing, and typically spent only a week or ten days in New York each month in any case. Often he would be away for six weeks at a time. And indeed he was gone for two weeks. But when he came back he wanted to see Sara again, and Rebecca graciously consented, telling me that as long as Michael was so attentive to her, she thought it would be okay if Sara went out to play with Phillip now and again. I was thrilled! This was a great deal! It took no effort at all - in fact it was a joy - to be attentive to the woman I loved, and I was thrilled to be able to go out with Phillip because I got to be as feminine as my heart desired. Rebecca even helped me with things like accessories and matching my makeup to my outfit. She said her purse and jewelry collections were always open to me. I was really touched by her generosity.

Veronica and I became great friends because each time Phillip came to town, I needed a make over. I was going from boy to girl and back to boy and back to girl again on a fairly regular, though not terribly frequent basis. And true to my word, I let my nails grow, and then, my hair as well. Veronica insisted that I get my ears pierced, and Rebecca finally went along, “as long as it’s only one hole in each ear.” I was in trannie heaven, with both a loving and accepting wife and a boyfriend who took me on dates, but demanded no sex, though he was very playfully affectionate.

Out of Rebecca's sight, we were like teenagers overcome by their first infatuation, and I'm sure many people who saw us together assumed that we were lovers. Phillip often copped a grope of my ass, which, after I began to relax at his touch, I really sorta liked, and it was a constant (though very enjoyable) battle to keep his hands off my faux breasts, something that seemed important to do for propriety’s sake, but that at the same time felt silly. I mean, they weren’t real and I couldn't feel anything in any case. Still this often led to a good deal of semi-public twisting and squirming and swatting and pushing whenever Phillip felt like teasing me, which seemed to happen whenever he thought no one could see. And as I half-heartedly, though insistently tried to divert him there was something about seeing my manicured hand on his chest or his arm that really made me feel really special, in an attractive, sexy, vulnerable way. I came to realize that this was one way Phillip and I could safely express affection for each other, and I enjoyed it. And though I probably would have denied it at the time, it turned me on. So we slowly became chastely intimate. I let him hold my hand, or I took his arm in my hands, or cuddled under his massive shoulder. After a few months, touching was no longer a big deal between us, and I savored being sheltered by his gigantic presence.

This all led to me become quite comfortable as a woman and as I relaxed, I began to explore various ways to present myself, looking for the real Sara somewhere within me. I started off timid and demure, and my hair and clothing were conservative and constructed. But that wasn’t really me, and I moved through phases when I tried to be elegantly sexy, softly romantic, an artistic gypsy, and on rare occasions, even provocative, in very short, clingy, backless dresses and high, high heels. The few times I tried that particular persona Phillip and I went out to guy places, where I could be shown off as a trophy date, but where we weren’t likely to meet people we knew. I found it both thrilling and frightening, and Phillip really seemed to have great fun showing me off, but that wasn’t me either. I started to feel like I would never find the real me.

And then one day, as I watched Rebecca get ready to go with me for a long-planned sixth anniversary evening of dining and dancing, it hit me. I could be any of those kinds of women, any time I wanted. She had come home very distracted, and in a hurry because we were late. Her movements were tight and hassled-looking. She was dressed in her usual business suit, some pedestrian brown pumps with blocky heels, her hair up in a tight French roll, and wearing very light makeup, as she typically did during the day. Then, after a quick bath, she seemed much more relaxed. She slipped on a most delightful set of lingerie and then sat at her makeup table. She unpinned her hair and let it down, before using hot rollers to give it some bounce and lovely little curls at the ends. She darkened her makeup, and slipped into the most romantic dress made of several layers of transparent chiffon over a rayon lining. When she was done, she stood up and gave me a twirl, a huge smile lighting up her face. “Come Michael,” she said, slipping her arm through mine as I looked on beaming, “I’m ready for a romantic evening with my favorite husband.”

In less than an hour, she had gone from being a rather well dressed and attractive, though intense and harried, business professional to a relaxed, vibrant curvy babe, but she was still Rebecca. It was then that it hit me. I couldn’t pick a persona by what I was wearing, and my clothes certainly weren’t going to be able to define who I was. I would be who I was; I didn’t have any choice about that. On occasion, I could be whoever I wanted to be, or whoever the situation suggested I be, and then switch back again or to something else altogether, no matter what I wore. There had to be a me there to begin with, and that me could be dressed up any way I wanted. Although I understood that I still hadn’t found my authentic Sara, it was then that I learned that I could play at, and dress like, whoever I felt like being. The clothes didn’t define me.

This realization made me quietly buoyant. It freed me from the transvestite prison of being my clothes, and opened more attractive options for defining my personality. This night for example, I was dressed as Michael, wearing a softly constructed black suit, dark charcoal silk tee shirt, and soft, black dress loafers, very urban hip, but clearly a guy. Earlier in the day, however, I had been wearing a pale pink, short pleated skirt, a figure hugging purple tank top, with a white cotton gauze shirt over it. I had spent four hours working on a series of design problems without ever once thinking about what I was wearing, except to pull my skirt under me when I sat down. And the me inside these two different sets of clothing hadn’t changed, although the way I moved and talked and held myself certainly had.

By the way, we had the most wonderful evening, both of us basking in the glow of each other’s love. We truly felt like soul mates.

After that, I paid much more attention to the things I did and said. They, I realized defined me far better than anything I was wearing. Sure, I was still hyper-aware of my clothing, but I discovered that Sara was a woman very much like Michael was a man. I liked being nice to people. I was attentive to and empathetic with their emotional needs, even if that only meant a nice smile or a gentle touch in return for a small courtesy. I wanted people to like me, and was willing to go the extra yard to make myself likable. And I wasn’t at all eager for confrontations, which, of course, is why Rebecca did all our negotiating, and tended to be the dominant one in our relationship. I was somewhat shy and far more comfortable when I was dressed more modestly than when I was at all provocative. And as I learned to be myself, the whole experience of being womanly took on a different dimension for me.

My nurturing impulses blossomed. So instead of being somewhat embarrassed that I was the “neat one” in our family, and cleaning up guiltily (how bizarre is that?) or resentfully (which is, of course, far more typical), I began to see my nesting instincts as an expression of my femininity and let them have full reign, which allowed me to enjoy them far more than I ever had. Now, when I was straightening up the house, or arranging some flowers, or cooking a dinner, I didn’t have to dress like a woman (although I still loved to and often did), because I was doing something that felt like an authentic expression of my femininity, which was a far more meaningful and enriching then just dressing up.

I started to imagine myself as Rebecca’s housewife, and reveled in my ability to make her life easier, to comfort her when she was angry or depressed or upset, and to take care of the little things, like buying gifts for her to give to our employees so that she didn’t have to worry about “little stuff” like that. She was my queen and our home was her castle. I knew this was a rather old-fashioned view of what a wife was supposed to be, but as time went on, I could see her confidence, optimism and energy flourish. It made my heart feel so full! Then, if I happened to be wearing one of my now favored longer skirts - perhaps an ankle-length pleated crinkle skirt in gauzy cotton paired with a spaghetti strap cami or wrap front halter, it was icing on the cake, rather than the whole cake, which is what it used to be.

And unexpectedly, my work started to change. My designs lost some of the assertive edginess that had been one of my trademarks, and became much more liquid and sensual, exploring curves and interconnections in new ways, while being more peaceful. This turned off some or our potential clients, and some of our existing ones who left us, but it attracted others, and over the course of a year or so, we found ourselves with a rather large portfolio of women-run businesses, or at least of businesses that had women making decisions about marketing. Rebecca and some of our staff were uneasy for a while because our style had changed, and they didn’t know what we were selling. But after a rough period that lasted a few months, things got evened out and everyone was content again, knowing who we were.

I was also getting increasing numbers of strange looks and responses from people. I know now, and would have known then had I not been in denial, that those looks were due to my increasing femininity, and to the increasing invasion of my male life with feminine gestures, expressions, and mannerisms. In my heart, I must have understood that people now perceived me strangely, but I also remembering thinking, ‘What’s his problem,’ ignoring the obvious. The staff at work didn’t seem at all concerned, and if anything, my relationships with them, or at least most of them, seemed to get better.

And for that year, the whole thing seemed to be working. Things with Rebecca seemed fine, sometimes even really great, our business was prospering, and Sara had great adventures with Phillip. When he took me to the ballet at Lincoln Center, I got to wear a long velvet gown for the first time. And when we went to a Knicks game, sitting only three rows from the court, I wore my leathers, and drew the attention of not just the fans, but a couple of the players as well. I went to a couple of fancy parties in flirty cocktail dresses, and a few times, just had quiet dinners out with Phillip, who was always gracious, attentive, and protective. The problem was I came home from nearly every excursion exhilarated. This apparently happened even when I sometimes came home the next day, after staying in the spare bedroom at Phillip’s corporate apartment on Seventh Ave and Central Park South. And each time, though I didn’t see it, Rebecca would become a little more distressed.

Everyone could see me changing but me, and I was having so much fun I was blind. Phillip was becoming an increasingly important part of my life, and while I was having great fun going out with him in what seemed like a big game, I was also growing emotionally closer to him, peppering my conversations with “Phillip this” and “Phillip that.” Not surprisingly, Rebecca could tell what was happening and became increasingly anxious and threatened by the whole scene.

I did question her about how she felt rather frequently; I could sense when she was upset, impatient, or distant, but she always dismissed my concerns airily, saying that she had no problem with two guys being good buddies, even if it was in a rather strange way. Sadly, I believed her. I was having too much fun to want it to end, so I never probed below the surface, even when Rebecca would become withdrawn or short with me for no apparent reason. After awhile, we were both lying to each other and keeping the best face on our marriage and working relationship even as strains started to grow.

Rebecca eventually told me that each time I came home from one of my “dates,” she used the word bitterly, I behaved just like a teenage girl who had a crush on some new boy and couldn’t wait to tell her sister, all about it. “I thought I was watching you fall in love,” she told me. “And I was heartbroken. I didn’t know what to do. How could I compete with a man?”

I, of course, was clueless, perhaps willfully so, about her feelings, just as I had been clueless about my increasingly femme image. Even though I had never been what anyone would call macho (I was much too “artistic” for that) I was gradually becoming more and more feminine with my longer (although publicly unpolished) nails, long, smooth, shiny hair, and carefully trimmed eyebrows. Now, looking back, I have no doubt that feminine gestures, phrases, and movements often crept into my behavior, and most of the world probably thought I was gay. This must have been terribly embarrassing for Rebecca, though she didn’t let on to me for the longest time.

In the end, it was our contract with Matti that blew everything wide open. I had already agreed, initially at Rebecca’s urging, but later because it was what I wanted to do, to meet with Matti only when dressed as a woman. But we always met with her away from the office, often at her restaurant. We all got along great, and she seemed to especially like me. It was if we had some special affinity for each other. We had an easy, teasing, relationship, and I somehow seemed to understand just what she was looking for in a marketing approach. Although her contract wasn’t very big, we all felt our approach was really exciting, and Rebecca and I were terrifically proud of it. But that wouldn’t have changed anything, if it hadn’t really been as good as we thought it was. A few months after we rolled it out, an east coast trade journal noted it briefly, but admiringly, in a sidebar to a bigger article on small advertising firms. We, of course were delighted because it was free publicity, and it did indeed lead to an up tick in business. What we didn’t foresee at first, but which became all too apparent later on, was that this increased publicity would lead to increased scrutiny as well.

A month or so after that story appeared, we got a call from a much larger, national business magazine that was doing a story on restaurant marketing. They had decided that our approach for Matti was on the cutting edge of a new trend, and they wanted to interview us. Despite the new business that might bring, we said no, this time understanding the risks. But the reporter was insistent and eventually agreed to meet with us and our staff one day when, at the very last minute, I turned out to be “unexpectedly out of town.” The reporter was really interested in what we were doing and how we worked, and Rebecca thought the interview had gone really well until the story actually appeared two months later, just after Labor Day. Actually, the story was really very complimentary and we would have been basking in its praise, except for one little detail. It also included a picture of Sara.

Although she swore up and down that she had nothing to do with it, I was sure Matti had set me up because the picture was of the two of us, sitting at one of the little cocktail tables in her bar. We had hit it off so well while working together that we started to get together socially. It wasn’t a big deal: we’d have lunch or shop for an hour or two. She always had wonderful ideas about what would look good on me. Sometimes, when I wasn’t too busy and the restaurant was quiet, as on the day of the picture, we’d have tea. The junior staff, trying to show off for their boss, made us delightful little snacks, and we sampled all kinds of exotic teas. I had no way to know for sure if it was her; one of the staff who knew I was coming might have set it up. Still, I didn’t see her for a very long time after that.

The picture was, in fact, quite flattering. I was wearing a tight, long sleeved tee shirt and a colorfully printed silk robe-like jacket over it. My hair was in a high pony tail, tied with a ribbon that picked up the background salmon color of the jacket, and I had arranged carefully curled tendrils around my face (I had no idea how to make them - they took me forever!). I had on dark eye make and very red lipstick. The picture was taken from behind Matti, and I was gesturing animatedly about something, a big smile on my face. The major saving grace was that they didn’t use my first name, describing me only as M. S. Cohen, co-owner and artistic director of Mind Games. Whether I wanted to be or not, I was now out.

Over the next couple of months, as word got around, the shit really hit the fan. Rebecca was nearly frantic, the staff was in turmoil, our neighbors were aghast, our families freaked, and I was appalled. I spent hours and hours talking with people to explain, as best I could, who I was and what was going on. But to do this, I had to first figure out what to say. Rebecca pushed the subject the very night the article was published. She came home early and found me sitting in the sunroom, dressed in shorts and a tee shirt, my hair in a low pony tail. I had been trying to figure out what to do, and in fact had spent some time cursing my bad luck, feeling sorry for myself and crying. My eyes were red.

“What’s your problem?” she asked sarcastically as soon as I looked up.

“Fuck you,” I hissed back. “If you’re here to fight, I’ll just lea… — No! Wait! I didn’t mean that. I’m really sorry for what’s happened. I feel bad for myself, but I’m mortified about how it’s going to affect you and everyone we know.” Then I looked down, my shame preventing me from looking her in the eye.

I could see her legs shift, and she came over to the sofa and sat down next to me. “Oh honey, what are you gonna do? What are we gonna do?”

“I don’t know Rebecca. I really don’t. But I think I have to decide whether this is just some crossdressing game I’ve been playing, and then rein it in, or whether I really am transsexual, and just go full time to see what that means.”

“I….” and I looked up at her helplessly, holding my hands out in a gesture of futility. That’s just what I’d been trying to understand all afternoon, but by now, I couldn’t figure out what was in my heart and what was in my head, whether it was riskier to do nothing or to go full time. Whether I should tell people dressing is just something I enjoy doing, or that I think I’m a woman.

Rebecca, bless her heart, leaned over and gave me a hug. “Let’s talk,” she said softly. “Maybe together we can work it out.”

We talked for hours, and that’s when I learned about all of her fears, and her anger and her frustration. She understood she had some responsibility for what had happened, especially by introducing Sara to Matti, but was adamant that I was responsible for everything I had done: the way I had enthusiastically gone out with Phillip every chance I got, the way I had pursued increasing femininity, and that I seemed unable to restrain my feminine impulses, giving little thought to the implications of what I was doing.

At first, I listened impassively, then resentfully, and finally with increasing hostility. *How dare she accuse me like that?* I thought to myself. *This never would have happened if she hadn’t pushed me into it.* But as we talked, things became clearer to me. Just because she had forced me to go out with Phillip once, didn’t mean I had to go out with him over and over again. Just because she had become lenient with my dressing at home didn’t mean I had to push the envelope every chance I got. And it certainly didn’t mean that I had to be blind to the effect it was having on her and everyone else around me. I was becoming wracked with guilt.

“I’ll quit,” I finally said. “I just can’t do this to you any more.”

“No you won’t,” she replied, evenly. “You won’t be able to. Not only that, I won’t let you. It would be stupid of me.”

“What are you talking about?” I responded, trying to sound offended. “Don’t you think I love you enough to stop doing this?”

She cocked her head in that way of hers and looked at me sadly. Then taking a deep breath and straightening up, she said, “What I think Michael, is that you are really Sara. And that if we force that little bird back into the cage she just escaped from, not only will she die, but she’ll take Michael with her.” By the time she had finished, she was crying. Still, she went on, “And I can’t bear the thought of doing that.”

Of course, everything I knew about crossdressers told me that I would never stop entirely. I could purge and suppress it for a while, but it would inevitably come back. In the meantime I would be miserable, especially after all my recent freedom. Apparently Rebecca understood that also. And looking into her eyes in that moment, I understood that what I wanted to do more than anything in the world was live full-time as a woman to see if I was in fact transsexual. Could I do it day after day, in every activity, in front of all people? But before I could say that, Rebecca started talking again.

“Michael — Sara — I don’t know who you are any more, and I can’t go on like this. I need to know one way or another. Are you a guy who likes to dress like a girl or are you a girl? Do you even know?”

All I could do was shake my head sadly.

“Then I think our path is clear,” she went on, obviously having made up her mind. “You have to become Sara full time. If you do that and discover that you’re really Michael, then maybe we can continue our marriage. If you discover that you’re really Sara, however, I’d rather know that sooner rather than later.” Her eyes were filled with tears, and she had a pleading look on her face.

My lips quivered, but no words came out. l felt stupid, culpable, guilty, and worthless all at once.

But Rebecca wasn’t waiting for me to reply, she was only trying to get control of herself so she could continue. After a deep breath, she went on. “I don’t want to lose you, but I can’t stand the way things are.” She hesitated for a few moments, and then went on, “And besides your hand has been forced. It’s just impossible to continue on the way the way you have.”

“I know,” I mumbled dumbly, trying to imagine what I would say to my parents. All of a sudden my life didn’t seem like such a big adventure any more; it had turned into a bad dream an adventure in the Twilight Zone.

That night, as we got ready for bed, Rebecca placed a sweet spaghetti strap, knee length nightie on our bed. “Wear this,” she said, when I had come out of the bathroom. “And then cuddle up with me in bed. I need to feel you near me.”

So I did and we did. But cuddle is all we did. We didn’t have sex. Rebecca pointed out, gently but firmly that she wasn’t a lesbian, and if I was a girl, well, we could be intimate, but it was hard for her to imagine how that would lead to sex. I don’t know whether Rebecca intended it, or was even aware of it, but I saw another message embedded in what she said. If I became Sara our marriage would be over.