Crossdressers - and the men who love them
Know where to draw the line between fantasy and
reality
About two or three times a month I get a letter from what we in the transgender and crossdressing community refer to as an admirer. Typically, these men either would like to meet me and take me out on a date, or want to know where they can meet crossdressers and transsexuals. Typically, they are not crossdressers themselves, although some admit to having tried crossdressing.
At first I pretty much ignored this e-mail. I myself was not interested in meeting men, even for friendships. My detachment, however, gave way to curiosity when I realized that there were quite a few admirers out there (a rather large percentage of them were right here in my area). I started to feel that I needed to take the subject more seriously. I don't want to close my mind to issues around crossdressing that are personally not important to me, or personally objectionable. In this case, dating men is just not important to me, mostly because I am involved in a long term, monogamous relationship.
I also came to the realization that many male-to-female transgender persons have a need at some level to experience being in the female role in what appears to be outwardly a heterosexual relationship. Not that this necessarily means having some kind of sex with a man. It may be as simple and as harmless as being taken out for coffee, dinner or a drink.
While almost all of us fantasize about playing the female role, a much smaller number of us act on that fantasy. And with good reason. Many crossdressers are married, and view such actions, rightly so, as a form of cheating on their wives. Others feel guilt and shame over having some kind of homosexual fantasy, even though this is common among men, including many men who are not crossdressers.
Yet the reality is, that as we spend more time in a female role, the desire to explore this role further does grow. Perhaps not to the point of wanting to go the route of full SRS, or to even necessarily want to spend significantly more time crossdressed, but to spend the time crossdressed more immersed in a female role.
To a certain extent, the Internet and the Web have allowed some of us to play out this role in a virtual world. Many of us never venture out into the real world en femme, and cyberspace is the only place where others get to see the inner woman. But many of us do meet the public and have discovered that a crossdressed man out in public does not cause the world to stop spinning. And we begin to feel that we have a right to do what we do. Our sense of self, who we are, changes. As our comfort level with being out in public grows, we start to imagine more of the possibilities that are opening up to us. We begin to think of ourselves, if only temporarily, as women. Others may not think so, but we do.
So I can understand why crossdressers would want to spend time with a man, wanting to explore a new role, fulfill a fantasy. However, I hesitate to ask why a man would want to pursue a relationship with a transgendered person. Simply asking the question implies that there is something wrong with it, that it somehow doesn't fit into a cultural norm. So I don't ask these people why they want to meet crossdressers. I take for granted that they do. After all, everyone wants to meet someone.
But relationships can be battle zones, full of land mines. People can, and often do, get hurt. You may get what you asked for, but not what you wanted.
And this is really the most important thing: there is a strong element of exploration on the part of both the transgendered and their admirers. Some people know exactly what they want, and many don't. And some don't know they didn't want something until it's too late.
I know that this is starting to sound very negative, as if I am trying to pursued you. I'm not. But whether you are a crossdresser or an admirer, I think your expectations should be realistic. Some men look very good when they dress and wear makeup, some look better than many women. Many of us don't, which is why crossdressers sometimes turn to hormones, hair removal and cosmetic surgery despite having no plans to live full time or transition.
An admirer may find himself out with, dare I say it, a guy in a dress. If that's what you are looking for, then you won't be disappointed. But if you have only admired from a distance, and have never really met a crossdresser, then you are pursuing a fantasy. Reality often fails to rival our fantasies. On the other hand, if you are a crossdresser looking for validation from an admirer, you may instead find yourself in the role of sex object.
One of the things, I believe, that attracts some men to crossdressers is the "hyper-femininity" that crossdressers often express through their choices in clothing, makeup and wigs. Crossdressers rarely, if ever, don shorts, t-shirt and sneakers when they want to cross dress. Makeup is almost never applied lightly, so as to not be noticeable. For most crossdressers, crossdressing usually means dressing up.
Being wanted only as a sexual object may be thrilling at first to a crossdresser, especially one who has been in the closet for the most part, but it won't satisfy anyone with a reasonably healthy self esteem for very long. Being told by an admirer you are beautiful and sexy is nice to hear.
If you are a crossdresser who has an unsupportive or hostile partner, then the desire for validation and acceptance will be even stronger. This kind of circumstance is not limited to the crossdressing community. If you have ever worked with troubled adolescents, you know that they often engage in reckless, risky behavior as a way to get attention and affection. This is especially true in highly dysfunctional families. The need to fill a void left by unsupportive parents is a major factor in teenage pregnancies. These girls want someone to love them.
I'm not implying that every crossdresser who seeks some kind of relationship with a man is in a dysfunctional relationship. But you should answer that question for yourself and realize that if this does apply to you, you need to be pursuing other solutions to your problems.
In a similar vein, admirers may also be vulnerable to being used by crossdressers who only want to act out a fantasy or satisfy their bisexual curiosity. I have seen personal ads from men who want a long term relationship with a transgendered person. A crossdresser may be seeking a one night stand.
I once attended an S&M fetish party where I met a professional dominatrix from New York City. Prior to becoming a professional dom, she operated a transformation studio for crossdressers. The first question she asked me when she met me (after asking me my name) was if I "like to suck cock". Now, I wonder why she was under the impression that just because I was a crossdresser that I would like performing fellatio.
OK. I'm being sarcastic.
Sexual fantasy rarely takes into consideration consequences. That's what makes them so much fun. That's part of the fantasy. Like Isadora Wing's "zipless fuck" in Fear Of Flying. No name. No face. But the reality is too scary to ignore. In the '90s, casual sex kills, so you really have to know the person you're with. That's called a relationship. And there's never anything casual about relationships.
I think it's important for us to explore our gender, to experiment with sexuality, to live life with no regrets. But no one is so completely free from all responsibility and commitment that they can do so without a thought for the consequences.
