Well you probably don't remember but I contacted you earlier with some trouble about my boyfriend (a self-hating Christian); things are going well now -- I took your advice, so I talked to a friend who was also Christian, and he did help, but things sort of took a weird twist, and by weird I mean WEIRD. Well I didn't say before but he is very effeminate-looking, and from time to time he likes cross-dressing, I enjoy when he does this and help with his makeup and stuff; it's fun and I like the way he looks. At first it was just something we did behind closed doors you know, alone, but eventually a friend of ours walked in on him in a skirt. She didn't react negatively, in fact she kind of encouraged him, to the point of convincing him to take a couple of pictures posing like this. She says that they we're just for practice since she enjoys photography but, judging by how she is, those pictures might already have found their way onto the web. I was worried, but he was joyous, and aroused, and after some time in bed I forgot my worries until a bit later. A few days later I caught this friend and my boyfriend in the street, only he was wearing a skirt, a top and a small sweater. I freaked out since it wouldn't be nice if he stumbled into one of his friends that recognized him, or even worse, his parents, cos' if being gay wasn't enough I bet cross dressing will surely give his father a heart attack. I warned him but our friend simply said they were having fun; I usually could convince him but with our friend's support they convinced me to accompany them. I just looked around for someone we knew and nervously went around for the rest of the day. It was not fun and after we went back to his house I tried to talk him out of this, and just like the time of the photo shoot he used the one kind of argument I can't resist.
Now this wasn't long ago, and it's still going on, and I can't talk to him because we are either with company I can't discuss this in front of, or with our friend who somehow always manages to out talk me or alone where he can out tongue me... so he's pretty much got me on a short leash on this. I keep trying time after time to convince him but I can't and I know that doing this will eventually land him into trouble, bad trouble. I mean I haven't been around most of the time he does this but I've seen him getting complimented and flirted with, and this makes me jealous, and I have bounced a couple of guys but apparently when it's just him and our friend he does flirt with them, and this also makes me mad. I need to talk to him, but I don't really know how to proceed... by the next time I see him I very much need to snap him out of this mad stuff!
Final note: I talked this over with one of my more mature and smart friends, he said something that seemed very interesting, that he may do this in order to attract attention from men -- is this logical? Why do you think he does this?
Well, my best guess is he does this because he's a drag queen -- a gay man who's also a transvestite [someone who gets off on wearing women's clothing and/or in having a female persona.] Some drag queens feel a need to live most of their lives -- at least [in their opinion] their real lives -- as women. They are not transsexuals, as such [perhaps some are], but they do have a strong female identification.
I'm not entirely certain why this troubles you so much since you have no problem with him being effeminate. Of course, there's a big difference between a kind of "girlish" guy and a drag queen. Do you guys live in a small town? Are you afraid he (or both of you) might be gay-bashed [a problem he might face even when he's not in drag, as you say he's somewhat obviously gay]? Until both of you are comfortable with his cross-dressing, it might be better for him to do it at home or only in gay clubs. [Not bear or leather bars, however, LOL.]
If he's a bonafide, genuine transvestite, he can't help his feelings, and he shouldn't be ashamed of it, and don't help him feel ashamed. I mean, you say he's feeling better about being gay -- it sounds like he's anxious to smash the closet door right off of its hinges -- so don't turn around and give him a complex about being a cross-dresser!
Some gay men, after they come out, especially the more stereotypical members of our community, want everyone to know and go about it in the most flamboyant way possible, and I suppose this whole cross-dressing thing might just be a "gay" act he's putting on, trying to be as wild and "out" as he can be. It probably amuses him that it freaks you out.
On the other hand, he might be a legitimate "TV." A Christian drag queen? Why not? You can either deal with it or you can't.
As for wanting to attract attention from men? Well, most gay men are turned on by masculinity, not by guys in dresses, but there are exceptions. If for some bizarre and pointless reason he's trying to turn on straight guys, he's just asking for trouble, especially if he's convincing enough to pass for a "real" woman. Nothing gets a homophobic straight guy angrier than being turned on/flirted with by a woman who turns out to be a guy.
I suggest you sit down and talk with him and find out just how far he's into the drag scene, and how far into it he wants to go. Does he eventually want to live most of the time in female drag and with a female name and persona? The vast majority of gay men have absolutely no interest in dressing up in drag, but those who do really dive into it and some never come up for air. This just may be a phase for your boyfriend or it may be the real deal.
It doesn't make you a bigot if the drag thing becomes a turn off for you, but it may mean that this guy just ain't the right guy for you after all. But remember, there's nothing really wrong in being a transvestite or drag queen.