A Nice Note to a Cross-Dresser

I do some professional part-time work as a Dominatrix (emphasis on “part-time”). Now and then, I’m approached by a gentleman who likes dressing up in female clothing and is mortified.

With personally identifying information omitted, here’s my reply to one such gentleman, in the hope it’ll help others.

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Many gentlemen talk to me about similar desires to yours. Since dressing as a hot girl is erotic to you and that’s your focus, as opposed to it feeling right for you 24×7, you’re probably simply someone whose dress code crosses the gender barrier, a.k.a. a cross-dresser (as opposed to what I am, someone whose brain is female while other parts are not, a.k.a. a transsexual girl).

Almost always, it’s a traumatic thing for the men who approach me  … dressing as a girl is very erotic for them but they feel like something is wrong with them, which bothers them about themselves and it’s certainly something that they cannot see ever bringing up to their wives.

Actually, many men have an interest in wearing women’s clothing. One study puts the estimate as high as 30%. Even so, in most cultures, it’s a huge no-no, and is even one of the things the Christian Bible is explicit about. That same book is also explicit that you should wear tassles on your clothing, so I’m not too worried about trying to live by the standards of that idea set. Still, it’s an aspect that many people latch onto and so culturally it is often considered to be a bad thing.

Let’s pause and dwell on this for a minute. We live on a planet where wars, violence initiated by government against its citizens, violence initiated by some citizens against others, drugs, illnesses and accidents have a huge and negative effect on mankind. It’s hard to imagine something more harmless than a man slipping into a sexy thong and a pair of 6″ stilettos. And yet, such actions are considered to be a big, negative issue when in fact the damage from them is zero and many good things can come of it. Morally, psychologically, operationally … I see zero essential problems with a male dressing as a female.

Still, for most men, it’s almost impossible to avoid an initial “oh, I better not” recoil. That, plus the desire, however initially weak, sow the seeds of an obsession. They think about it more, and recoil harder. Again and again, this habit pattern weaves many thin threads into a thick braid of obsession. Perhaps, had the person given into the desire long ago, it might have been mildly interesting at most, and that would have been that. Indeed, once someone finally decides to give in to the temptation, he often finds that his fascination dwindles.

What most men consider utterly out of the question is to come out to their wives. I can see several major problems with this decision.

1. The assumption is that the man’s wife would react with horror. Although females often tend to initially rant and rave when given such news, that’s not the important reaction. What we come up with later is what matters, and it’ll typically be some collaborative way to make things work. It might even be really, really hot. At a time when I wasn’t yet 100% convinced that I’m a transgender girl, some of the most erotic times I had were with someone who loved seeing me feminized even under her assumption that I was basically male. So, although the lady might react with horror, she might not. She might very much not. And then again, if something is small as this, something so harmless, generates a truly bad reaction in her, is that really someone you want to be with?

2. The assumption is that socially, if word gets out, it can be disastrous. That’s true but only due to bigoted attitudes, e.g., water-cooler giggling conversations about “so-and-so dresses up as a girl.” Often, a good reaction to that is “Yes, I do. It’s very hot. I have hot people in my life who think it’s very hot too. I like it.”

Sometimes, many times, the people most vocal in their criticism are hiding their own similar desire — often from themselves.

Word getting out to the world at large might just be non-disastrous.  I, for example, have a too-masculine lower jaw and yet I go out every day dressed as a girl. I happen to BE one, but I look male. And, life goes on.

For those with children, I can imagine it having schoolyard bullying implications e.g., “your dad dresses like a girl.” Still, basing your sex life on the irrational actions of a bullying eight-year old whom you’ll never even meet … is probably not a great idea.

3. The assumption is that this means you’re gay. It might or it might not. If you’re gay, you’re gay. Facing it doesn’t make you less gay. It makes you courageous. If you are attracted to women too, then you’re not gay anyway, you’re bisexual. So is, according to sex researcher Kinsey, a large portion of mankind. And, if you’re gay, so is a sizable portion of mankind. And, anyway, there is nothing bad about being gay, or bisexual.

4. The assumption is that she won’t find out anyway. Females are very observant, curious and finely attuned to issues. As a generalization, we can pick up on subtleties that most male totally overlook. Many a cross-dresser has been outed by his wife finding a thong, not hers, in his car’s glove compartment etc.  If you think telling her you’re a cross-dresser is hard, imagine how hard it’ll be to convince her that it’s your thong and that you weren’t cheating on her with another female.

5. Honesty and openness simplify things and are a great foundation for life, including relationships.  Pandering to others’ irrational condemnation tends to give them an undeserved moral high ground.

I hope this helps. 🙂