- No T for Tea
Your question was deceivingly complex to tackle. Not because of the question itself, but because there seems to be a lot going on, in terms of semantics, possible misunderstandings and misconceptions. But don’t worry — your friends Pepper and Pearl will get you sorted out!
Rephrasing your question, all what you’re saying (in far fewer words, and much more simply) is that if your friend is not trans, what the heck is he? Because we seem to be wired somehow to require labels and categories that everyone’s supposed to fit into. (Don’t even get me started). But that’s where we get hung up with definitions of words that we may not all be using in the same way.
HE uses the word “transvestite,” and unfortunately neither one of us can say for certain what that means to him. In the strictest and most technical sense, historically, transvestism simply meant to dress, behave, and present as a member of the opposite sex (if we assume a binary system for gender). It was originally used as a descriptive, observational term, coined by German sexologist Magnus Hirschfeld. In his observations, he noted that transvestism could also be correlated with sexual arousal, so “could” immediately got reinterpreted as “did” and Bob’s your uncle — transvestism now meant that if you were a man who put on a dress, you had a sexual fetish. And hey, would you look at that! It’s even in the DSM to this day! (Just look up “transvestic fetishism”). So of course, the term “transvestite” quickly turned into a pejorative (because obviously) since any kind of sexually-associated term outside of heterosexual, missionary-position sex between married people would clearly represent a form of deviancy and perversion. As a result, the number of people who actively use the term “transvestite” has dwindled, because of its reputation as a(n unreclaimed) derogatory term. In that sense, the term “cross-dresser” is preferred. Although, I don’t know about you, but for me, even “cross-dresser” kind of gives me the heebie-jeebies, because it still presents an unbalanced, patriarchal (read: misogynistic) binary view of the world. Why misogynistic? Nowadays, only MALES can cross-dress, and the act of doing so is seen by many as problematic. Females are generally accepted regardless of whether they pull on a pair of trousers, or into a dress on any given morning. The same cannot be said for males, who are still expected never to venture into any territory that might somehow be considered “feminine.” Hey, I still know people who even refuse to eat quiche because they think it’s an inappropriate food choice for a REAL man… But I digress.
In a nutshell, the reasons WHY your friend dresses the way he does, are, I’m afraid, HIS business — and no one else’s. It’s not your place, nor anyone else’s to guess, assume, or judge his motivations. And if it DOES happen to be motivated by a sexual fetish, then that too, is none of your concern… And wanting to hang out, or go out (dressed as a couple of fine ladies) in no way would indicate to me any cause for concern, even if it WERE motivated by a sexual kink or fetish. Oh, and while we’re on THAT note, let me just point out, that I think Western society still hasn’t gotten over their puritanical, Judeo-Christian roots, perpetuated through Victorian prudishness and utopian-colonial ideals, to allow people the freedom to explore themselves as sexual beings. If you could administer a truth serum to a thousand people on the street, you’d probably be shocked how many of them have some kind of sexual kink or fetish. The mind boggles at how many men might actually be wearing frilly, pink panties underneath their homogenous, dark drab suits and ties… And speaking of ties… How many would enjoy being tied up?… Or covered in strawberry ice cream while being whipped on the ass by a dominatrix? Hey. Everyone’s got something. And my point is, that if your friend having a fetish involving women’s clothing creeps you out… That’s something that YOU will have to work through for yourself, as it’s got nothing to do with him.
So, my advice? First, don’t assume things that aren’t yours to assume. Enjoy your friendship for what it is, and go out with your friend just as you would with any other friend. You clearly seem to like spending time with him, so who cares what other people think? There’s no need for a T-shirt to explain anything. There’s always going to be self-appointed gender police, regardless of who you are and how you choose to present. And do you really think they care that one of you is trans and the other is not? And as for the creep factor… Until he asks you to cover him in strawberry ice cream, don’t worry about it!
Pepper & Pearl