There’s two often repeated jokes comparing crossdressers to transsexuals. They’re both funny ‘cuz they’re true. They also both reveal aspects of my own life. Yet on the surface they suggest completely opposite things.
Here are the jokes (after which I get all analytical, potentially draining the fun out of them):
First joke: What’s the difference between a crossdresser and a transsexual? Answer: A transsexual can’t wait to get home and take the damn bra off.
Second joke: What’s the difference between a crossdresser and a transsexual? Answer: About two years.
Here’s how they both apply to me even though they appear contradictory (the first suggesting that crossdressers are not like transsexuals, and the second suggesting they’re just different stages of a transsexual coming out).
The first joke makes a play on the idea of a crossdresser eagerly running home to strip off their “drab” attire and dress up as the opposite sex, while to a transsexual it’s just everyday clothing, ho-hum. It also kind of calls to attention an important distinction about motivation. Unlike crossdressers (at least unlike those who may dress up on occasion, but otherwise live happily as their birth sex) transsexuals are not really motivated by clothing. For a lot of crossdressers clothing is the primary motivation, while for transsexuals it’s a purely secondary effect of something else. There are transsexuals who never crossdress in their entire lives before transition.
One of my enduring memories about transsexual group therapy is how completely separated crossdressing behavior was from being transsexual. A couple people felt the need to crossdress to attend group, but that was very much the exception. The general rule was that people showed up presenting as the gender they were living as at the time. For the most part when someone showed up presenting as the opposite sex from the previous session it meant they were starting their permanent transition.
This was jarringly different from my previous experience with groups of crossdressers. For the crossdressers so much focus was put on finding opportunities to dress. For many of them any opportunity to dress was virtually a mandate to indulge their urge. Crossdressing was certainly permitted at our group sessions – the therapist explicitly called attention to this fact. But no one seemed to find it that big a deal. The general feeling seemed to be that if you weren’t in transition there didn’t seem to be much of a point to it.
The notion that someone would never crossdress before transition probably doesn’t make much sense to those who enjoy crossdressing for its own sake. But that’s the point. The two groups are really not coming from the same place about this stuff. Even if we don’t always realize it at first.
Which brings us to the second joke which is, paradoxically to everything I just said, also kind of true (that’s the one about the difference between a crossdresser and a transsexual being “two years,” in case you don’t recall).
Many transsexuals (once again, not all) pass through a period where we try to figure out our inner gender conflict by crossdressing. In my own case that was one of many different “cures” I attempted to make my gender dysphoria go away.
Shortly after college, I met some crossdressers – not the easiest thing to do in Central Illinois at the time (fellow tg dinosaurs: remember how difficult meeting other transgendered people was before the Internet?) In talking to some of them I learned that they could indulge their “feminine side” in small doses, live as their birth sex the rest of the time, and feel happy and content with their overall lives. That sounded great to me! Finally a way to make the gender conflict go away and start living a normal life!
But it didn’t work in my case. At first it felt liberating, but after a while it felt almost like torture… like dangling a tiny morsel of food in front of the face of a starving man only to snatch it away before he’s allowed to take a real bite. Ultimately what crossdressing did in my case was bring to my attention all the aspects of gender that crossdressing couldn’t address. In the end the experience left me feeling miserable, angry, and more conflicted about gender stuff than before.
If I had been in therapy at the time, realizing that crossdressing was making my gender dysphoria worse rather than better would have likely lead to me coming to terms with being transsexual. I had previously wondered aloud to E whether I might be transsexual, but always with trepidation. I didn’t want to be transsexual. The idea scared me to death. Crossdressers get the best of both worlds, I thought at the time. Transsexuals get the worst of both worlds. Why the hell would I want to be one of those?
But I didn’t have a therapist at the time, so I went with extreme denial instead (not a recommended alternative to therapy if you’re wondering). I quit crossdressing, declared myself “cured,” and bottled up all those feelings of gender conflict deep inside. I didn’t yet admit that I was a transsexual, but I knew for sure I was not a crossdresser (as George Costanza would say, “not that there’s anything wrong with that”).
The joke implies that crossdressing is just a stage in every transsexual’s path to self-acceptance. That’s certainly overstating things. But it does happen that way for a lot of us, which is the source of the humor. It was more like seventeen years rather than two in my case, but yeah… I am now the punchline of that joke. And I’m occasionally the punchline of the other one as well (if you’ve ever sighed a contented “Ahhhh!” when taking your bra off, you know what I’m talking about). That’s me… a walking punchline and seeming contradiction. But at least I can laugh about it nowadays.



Sometimes the only relief seems to be in finding something to laugh about.
I know what you mean about hoping you aren’t transsexual.
I’ve just been thinking along the ‘try out crossdressing to see if it will help get rid of the fog’ idea… sigh..
The only good news here for me is the seventeen years bit… let’s see that will make me about seventy-five. Maybe by then it will have gone away???? LOL
Yes, it’s funny how both of those jokes can be true. I didn’t do any real cross-dressing until I was already on a path I couldn’t yet admit to (so much of what you wrote is familiar to me!), but all it showed me was that cross-dressing wasn’t going to “relieve my tension” or “let me relax.” It never felt that way. It simply felt appropriate. It wasn’t too long before I realized that I was indeed transsexual. And that realization seemed to have taken the sting out of being what I really had hoped I wasn’t.
The cross-dressers I spent time with when I was first exploring were very helpful to me, and really nice people, but I never understood what made them tick and still don’t.
Wow am I glad I found your blog, and more specifically this post!
Diana, first of all I wanted to say you are beautiful!
Me, I’m 24 now and for the last couple of years I’ve been exploring and revisiting chapters of my early life to put into perspective what I feel today.
Although I told my mother as a child I felt and had wanted to be a woman, I fought hard to forget and overcome my feminine tendencies that she so much kept in check. But of course, it’s just returned stronger than ever.
So although I am pretty certain of who I am, I would definitely be the kind of transsexual who never cross-dressed before transition. (And I have, but so few times it doesn’t even count!)
And so, I think I will begin soon. I’m happy to have found this place.
Thank you.
Thank you very much, and welcome. I hope your exploration helps you resolve any lingering doubts so that you can learn to be yourself free of conflict.