This is a letter I sent, with slight variations, to a few select people after I had already come out to them. It was not the initial coming out letter. This was something I sent only after I felt solid that we still had a relationship worth keeping. The purpose here was to provide a better understanding of the narrative of my life so far… from my actual perspective, as opposed to the way I’ve seemed to others. I think it’s probably decent background for anyone taking the time to follow the blog as well.
I felt like I was a feminine child up until about the age of five. I didn’t think of myself that way at the time of course. I was just me. [My brother] was the one into sports and active “boy stuff.” I was into dolls (even if we called them “action figures”) and playing imaginative games. All his best friends were boys. All of mine were girls. In the days before kindergarten no one cared.
When I turned five all that began to change fairly abruptly. For one thing, [my sister] was born two days before my fifth birthday. There was now a real daughter in the family. For another, [my brother] started first grade at Saint Anne’s. At Saint Anne’s the gender divide was very clearly and solidly drawn. Boys wore one uniform, girls another. They played on separate playgrounds at recess. There were clearly defined differences in all sorts of other things, from bathrooms to expected behavior. The immediate effect on me was that [my brother] and his friends began teasing me incessantly for playing with girls, and not being interested in the normal “boy things.” And of course, when I started first grade at the same school the next year, that constant pressure to stop being feminine and start acting more like a boy was amplified by a thousand percent.
It was right about this time that I started having deeply secret fantasies about being a girl. I’d imagine walking into school wearing a girl’s uniform, and playing on the girl’s playground. But not long after the fantasies took a darker turn. I started imagine being put into the girls’ uniform and then laughed at and mocked by all my classmates. All that teasing and humiliation I was getting from any perceived femininity seemed like it would come to its full and horrifying fulfillment at that moment.
And yet, deep down inside, I knew I wanted to be in that girls’ uniform all the same. And that lead me to start crossdressing in secret not long after. I used to LIVE for the days when I would be left at home alone, and could raid mom’s and [my sister's] closets. I would sneak soft and pretty nightgowns to bed at night, and put them on to sleep in after everyone thought I was sound asleep. Of course I made sure I always woke up first so I wouldn’t get caught. And in fact I never was caught in my crossdressing a single time in my life. Mom once found a pair of panties I had stashed in my drawer, and she began to blow up at me, but I quickly defused the situation by proclaiming no knowledge of how they got there, and that it was probably just a laundry mixup. She never found anything similar again.
That pattern… secret crossdressing, with an ever growing sense of shame, and yet an equally growing sense of excitement… continued all the way until college.
I dated girls, but tended to prefer more boyish looking ones. Not like… masculine girls. Just more boyish body shapes. I didn’t do this intentionally. But I think it was just a subconscious way to imagine us “switched around” in my head when we kissed or got intimate. Which I did constantly. The only kinds of intimate relationships I have desired in my life involved me being a girl with another girl, or me being a girl with a boy. I have tried and failed my whole life to get interested in relationships with me in the male role. Might as well try to imagine I’m a toaster, or a lampshade – it doesn’t work. I’ve always just faked my way along in that regard, looking to the outside world like I was just like any other guy into girls, while in my mind it was very different.
In college I spent a really miserable and isolated freshman year. But in my sophomore year I met E. I was nineteen and she was eighteen at the time. We started dating at the end of that year. As my feelings for her got stronger, and I thought I may want to ask her to marry me, I decided I would HAVE to tell her about the crossdressing. This was something I had never mentioned to anyone in my life, but I didn’t want to be married to someone and STILL have that distance between us that I had with everyone else. I had no idea how she would take it, but one day when we were spending some time alone, I finally told her. She was shocked, but supportive. That very day she helped me get dressed and made up so she could see. And she said she liked it. You can imagine how blissful that moment felt, and how strongly I was convinced that we were soul mates that were meant to be together.
We had a wonderful relationship for about a decade after that. I joined the group Tri-Ess, which is a social group focusing on crossdressers and their supportive spouses. We even attended a big convention for that group in Chicago in the early 90′s. We also joined a group in Central Illinois for transgendered people of all kinds, though that was ninety percent crossdressers. E used to help me dress as a woman and help with my makeup for these things, and we’d always go together. So it wasn’t just token support.
We moved to the Minneapolis area in 1993, and joined another transgendered support group up here, continuing the same thing for a few years as well. But then things started to change for me. I was getting more and more frustrated because of two self-contradicting things. For one, I wanted to look like a woman. Not a tranny. Not a pretty boy. A woman. I wanted that body shape; I wanted the clothes to fit me properly; I wanted the smooth skin… I wanted to look completely like a real woman. As a result I was putting more and more effort into looking that way… by the end I was spending 2-3 hours getting dressed before going to any transgendered event. I had specially designed padding, and elaborate makeup tricks to hide the beard shadow AND look as natural as possible. I had learned to style my own hair so I didn’t need a wig. And I was passing better and better but… that lead to the other thing. I felt like a fake. I felt like I was wearing a big phony costume. I had guys hitting on me, and I was desperate to be able to date them.
Don’t get me wrong, I didn’t LIKE the idea of cheating on E. But these guys were into me as a GIRL! That was sooo much something I wanted to experience. But then I would imagine them holding me to dance, and feeling padding instead of a real body. They’d get up close and see how heavy the makeup was. We’d go to sleep together and I’d have to strip down to my hideously male body. I’d wake up in the morning with a dark beard shadow the makeup couldn’t hide.
The combination of these two things – the increasing desire to look like a real woman, and the increasing disgust with feeling fake – started to make me angry every time I crossdressed. Eventually it made me so angry I quit altogether.
During this time a couple of older women who had started their transition took me aside and told me they didn’t think I was a crossdresser, but that I seemed more like themselves… transsexual. I resisted their advice strongly. I had talked a bit to E about the possibility that I might decide to transition one day, and she had indicated she didn’t think we could stay together if I did that. She didn’t say it was a sure thing, but I never lost the feeling that transition for me meant losing her. So I convinced myself these transsexual women were just projecting their own desires onto me. I was really a crossdresser and didn’t need to think about transition.
So there I was… I couldn’t crossdress any more, because crossdressing was no longer a relief. It felt like a huge chore and it left me angry rather than relieved. But I couldn’t explore transition either because I couldn’t imagine losing E. And so… and it’s going to sound silly, but trust me I believed it 100% at the time…. I declared myself “cured.” I had “gotten it out of my system.” I told E that I wasn’t going to crossdress any more, and could now live a happy life embracing a fully masculine role. I called this “playing with the cards I’d been dealt.” Sure, I admitted, I would rather that I had been born a girl. But I wasn’t. And the only two paths to rectify it were going to make me even more miserable. So I needed to make the best of things and strive to live a happy life as a man. No more silly fantasies in which I would pretend that I could truly have some kind of a female life.
And with that I plunged pretty seriously into a conservative view of my Catholic faith, finding out how God would want me to live. And I quickly decided I was supposed to have children – something I had insisted up until then I was not ready for. But I was almost thirty years old now, and it was time to grow up. E agreed, and in a short while we had not just one, but three children. What’s more E had quit working to stay home with the kids, and I took the responsibility of going from a lower paying job which I loved to a higher paying one which was less fulfilling, and also a lot more hours and more stress, because I was supporting a family. That’s what men are supposed to do, and I was going to be a man. I learned to smoke cigars. I learned to drink scotch on the rocks and gin martinis. I took intense martial arts lessons to get tough. I tried to enjoy playing golf.
And as all of this was going on I was growing depressed. Just a little bit at first. It came over me slowly. It was easy to ignore it at first. And then it was easy to attribute it to a hard period at work. And then it was easy to attribute it to having kids. And then… then it became something I just stopped trying to explain. It just WAS. And that’s when it really started to get bad. I pulled back more and more… from friends… from family… from my coworkers… from my kids… from E… I started drinking heavily… then more heavily. I was going to sleep every single night by drinking to the point I passed out. I was hardly able to hold a conversation with E any more. We were living in the same house, but you could hardly say we lived together any more.
And then I stumbled upon a web site. It’s embarrassing to admit it now, but I was doing some kind of search for pornography. As my relationship with E had cooled, I had turned increasingly to such things as a replacement for our former sex life. My memory is a bit fuzzy about how I found this specific site. It was one of those “do a search, click on something interesting, follow a link from there to somewhere else” kind of things. But the result was that I found a transgendered roleplay site. Pretty soon I was spending just about every waking moment either writing up posts for that site, or chatting with other people I had met there on Yahoo Instant Messenger. Many of them were, like me, deep in the closet and looking for friendship even more than roleplay. And that turned out to have an unexpected benefit. Because one of the people I met there had also experienced severe depression. She started gently but firmly advising me to find a therapist. It took a while for me to do it but…
One day I woke up as usual, sitting at the table I had passed out upon the night before, and I made the realization that I was going to kill myself if I didn’t do something to change courses. I would die of alcohol poisoning, or passing out while driving, or killing my liver, or something of the kind just as surely as if I put a gun to my head and pulled the trigger. And I realized I didn’t really want to die. I wanted to have friends and relationships in real life like the ones I had developed online through roleplaying. I wanted to be happy again. I wanted to have a good relationship with my wife and kids. I wanted to look into the future with hope for the possibilities again. But I didn’t know how to do it. I needed help.
That’s when I finally made the decision to find a therapist. And I knew it had to be someone who knew about transgendered issues because, while I wasn’t considering that the cause of my depression, I knew something about that was important to my happiness. I needed to have someone I could talk to honestly about my feelings about that. So I did a little research, worked up the courage to make the first appointment and just, got the ball rolling.
It took many months of therapy before I seriously considered that I might transition. The therapist didn’t use labels like “transsexual” versus “crossdresser” or any of the other buzzwords. She emphasized that everyone was different. I didn’t need to feel pressure to conform to anyone else’s idea of my life. I needed to find my own path. But… hesistantly… I decided to join a transsexual therapy group. It was while sitting in that group – consisting of people from totally closeted to fully transitioned – that I realized I really was transsexual. Because, for the first time in my entire life, I was listening to people talk about their own lives and feelings and pain… and I was hearing all those secret thoughts and feelings I held inside of me. It was like they were reading my mind. I had NEVER experienced that in any other group of men or women. I had faked it plenty of times. But this was the real thing.
It was also in that group that a post-op transsexual corrected the answer I had given myself a decade earlier when I declared I was “cured.” I told her my reasoning… that I had to “play the hand of cards I’d been dealt,” and that I’d been born male so I had to make the best of it. And very kindly she said, “But you didn’t play the cards you’d been dealt. You weren’t born a male. You were born a transsexual.” And that was a kind of Road to Damascus moment for me. The scales fell from my eyes and I saw how I’d been handicapping myself in any attempt to lead a happy life. My attempts didn’t work, because they weren’t being honest about who I really was.
I decided not long after that I needed to transition. But also that I needed to do it carefully, respecting how majorly it would affect my life and all those in it. I wanted to build a better life, not simply rush through a transition checklist. And that’s how I made my new plan to personal happiness, and it’s been working far better than I ever could have expected.
I expected E to be supportive, but to eventually decide we would have to split up. But after a few months of considering, she made the opposite decision. She decided to recommit herself to keeping a strong and loving relationship – even though I would soon be a woman in all senses. And our relationship is now back to the strong, mutually supportive, and truly loving one it used to be.
I didn’t know how it would effect the kids, but they were all surprisingly easy to adapt to the idea, and I’m now playing a larger role in their lives than ever before. I’m also enjoying them a lot more.
I thought I would probably lose all friends and most family over coming out. But I haven’t lost anyone yet. In fact, I’m now finding it easier than ever to make friends, and grow closer to them. The barrier… the wall of pretense that protected my transgendered secret… is now down. I never realized how much that kept me isolated and alone from those around me.
Even my job is going wonderfully. I’m planning my transition in the workplace now, and unlike my pessimistic former self, I’m fully expecting that to be successful as well. Meanwhile, I find my productivity super-high, because I’m not just going through the motions of my job while dreaming of being someone else. I like my life now, and that has a huge impact on everything I touch and do.