Dating a Trans Man

OK, this is an unusual one.

A couple of months back i met this guy, i saw him at this bar, he instantly caught my attention, he's just so handsome! -- nice styled hair, Greek god abs and pecs and charming gray eyes. So i spent the rest of the night chatting him up and trying my charms on him, and by the end of the night i gave him my number and he left me drooling like a high school girl. And so we went out. While at the beginning i was just looking for a quick fling like most boys in their twenties, this seemed to take a more serious turn, but i didn't care.

With a couple of dates past and having come to know each other well, i started making several bold sexual advances, and he would always deflect them. So i started to have my suspicions, and eventually we got a moment in private at his place to talk about that and the conversation took a turn i never saw coming. It turns out the reason he wouldn't respond to my advances is the fact that he is a female to male transsexual. I was prepared for many situations but didn't know how to react to that, and so we talked about that for several hours; he said that he was too afraid of the sex reassignment surgery and besides had heard it didn't have such good results, so eventually i told him that i love him and that it doesn't matter. Then we stepped into the bedroom. I gotta say i love him and all but it was weird, it took some concentration to actually perform, something that had never happened before, but above all i enjoyed it and instead of concentrating on the state of his genitals i just concentrated on who i was with.

So a couple of days later i learned that a good friend of mine is a good friend of his too. He said he had not said a word [about his being a trans man] because he didn't want it to get in the way of a possible relationship. He also understood how the sex could get awkward, but i said that i couldn't tell him that. Truth is every time we have sex i must concentrate beforehand, and even though i enjoy it and it's been good so far i just can't seem to get "ready" without a little mental preparation. I truly love him and i don't want that to get in the way. I mean the rest of his body is clearly and beautifully manly, and i don't feel like me or anyone is in a position to force him into the [sex realignment] procedure.

It's just, i don't want this to get in the way as much as it does. I also do not have that much knowledge about the transsexual community, and it seems that female to males are harder to learn about than the other way around...

To finish i just want to know if there is any case like this that you know of. I have never known another relationship like this and i want it to go nicely. I mean the sex seems to be the only problem, and he hasn't so far known that it is. I mean it's something new to me, and i enjoy it but it still causes some trouble in my head, i just don't know...

Okay, for someone born biologically female to be convincingly masculine, they have to have some procedures of some sort done, even if it's just taking certain hormones, so your boyfriend must have had some work on his body. I take that the problem you have is that he's held on to his vagina instead of getting an artificial penis, which is expensive, and apparently not too convincing. This is fairly common among Trans Men. Since a vagina is so utterly feminine in nature, and gay men are generally attracted to everything that's masculine, I can certainly understand why the sexual experience seems strange to you. You're a gay man who's used to dick, so the whole situation seems a little bizarre and unreal. Yet you also love the guy and seem to be capable of getting beyond your initial -- for lack of a better word -- queasiness. As weeks go by you will probably become more and more comfortable with this situation, especially if you truly see him as a man and if both of you are in love with each other. If you never quite get used to it, then you both may have to face the fact that you just want and need a guy with a penis and that's that. [You can also try alternate sexual positions. If you're a top is your boyfriend willing to be a bottom on the, ahem, other end? If you have to make adjustments, so can he.]

I don't pretend to be an expert on transsexuality so I would suggest searching out web sites devoted to the subject where you can find out more and also possibly get in touch with other gay guys who are dating trans men. I know they exist. While trans men generally wind up dating or in relationships with other trans men -- or trans women, depending on their sexual orientation -- I believe it has become more commonplace of late for transsexuals to have relationships with non-transsexuals. Your situation is still unusual, perhaps, but not that unusual.

In the meantime, I'm not so certain it's a good idea for you to keep from your boyfriend the fact that you're not quite adjusting to the reality of his physical being. He needs to know that there is a problem, and maybe he can help you with it. It's better that he know now instead of finding out after he's hopelessly in love and you realize that you just can't make a complete adjustment.

On the other hand, sometimes love does conquer all.

I suggest you read another post on this blog regarding this very situation, as well as the several comments that follow it.

Was Michael Jackson a Transsexual?

Was Michael Jackson transsexual? Anon.

Well it might explain a lot if he was. According to biographers, new evidence is coming out that he engaged in sexual relationships with men, so it is quite possible that Jackson was homosexual. If he ever spoke to anyone in regards to realignment surgery -- in other words, about getting a sex change -- that may eventually come out. Until then, there's no way to know for certain. Jackson's increasing "feminization" may have been part theatrical, part stereotypically gay, part glamour -- or it may have been that he genuinely felt he was a woman in a man's body. So Jackson may well have been an unacknowledged transsexual. If he was gay, he was certainly not out of the closet, and was probably plagued with issues of self-hatred. I doubt if he would have felt much better about himself if he were transsexual. All of his surgeries and cosmetic changes (and cosmetics) made him kind of edgy, but apparently he was only willing to go so far. Raised in an environment where people just didn't talk about such subjects as homosexuality [romantic and physical attraction towards your own sex] and transsexualism [being a different gender than the one you were biologically born into], Jackson was probably quite confused.

In any case, it is doubtful that (especially during his most successful periods) he would have come out as either gay or transsexual for fear that he would lose his fan base.

Had he lived, who knows how he might have identified in the future?

Switching Gender

I'm sure that most transsexuals are really transsexuals, but have there ever been cases where someone who was not transsexual wanted a sex change for some other reason? Is Cher's daughter -- or son -- the former Chastity, a true transsexual or a lesbian who for some reason decided she'd prefer to be a man? Confused Connie.

Transsexualism is very different from homosexuality and I won't pretend to be an expert on the subject, although a little googling will bring you to web sites where you can find more information on it. Based on conversations I have had with Trans People I would say that most people who identify as transsexual and undergo realignment surgery are truly transsexual, because -- while the process may be "easier" than it once was -- it's still not exactly a walk in the park. On the other hand, people contemplating a sex-change are advised to speak to professionals who can not only help determine if they really are transsexual, but if realigning physically to another gender will still be the right choice for them. Sometimes it is, sometimes it isn't.

There have been cases of people who have been advised for one reason or another not to undergo realignment, and they go through the procedures anyway, going underground to get the needed drugs and hormones. I don't have to say what a bad idea that is.

I have no doubt that there have been a few cases where people who were not genuinely transsexual may have wanted to change their sex. Not knowing Chastity or Chazz, I can't say for certain what's the deal in this case. S/he would not be the first person who identified as lesbian and then realized she was or at least identified as (more or less) a straight male in a female body. It works in reverse for men who identity as homosexual until they come to realize they are heterosexual females stuck in a male body. Have there been cases where a guy is so horrified at the thought of being homosexual that he'd rather transform into a hetero female? Sadly, I have no doubt that this has happened, particularly years ago, but I believe it's very, very rare. Internalized homophobia carried to the nth degree.

There are drag queens whose lives dressed up as women seem much more real to them than the time they spend in "regular" male clothing. Are these gay transvestites unacknowledged transsexuals? Perhaps. Yet some get angry at the suggestion that they are not, deep down, guys after all. Others may have such a strong suggestion or fantasy that they are women at heart -- although not in the same way that a transsexual does -- that they might desire a sex-change to become fully female. An interesting question is -- if it's all a state of mind anyway -- are they transsexuals regardless of how they view themselves?

Most people make changes to improve their lives and become happier. If this works for Cher's daughter, all the better. if she is fooling herself, however, about who or what she really is, then it may not be a wise decision for her to make the switch.

There have always been people who have said "I wish I were a man" or "I wish I were a woman" but they shouldn't be confused with true transsexuals. Still, with the increasing acceptance and frequency of sex-change operations -- and the politically correct need some people have not to question anyone as to their orientation -- it is not entirely unlikely that some of these people will slip through the cracks. But they are definitely in a very small minority.

A final note: Most lesbians are perfectly happy being female, as most gay men are perfectly happy just being guys.