Boyfriend and Transgender Incident

Hey,

So I've recently been dating a guy for a couple of months. We were drinking and then he had a freak episode (hyperventilating, trying to hit himself) and then the next morning I made it clear that I needed to understand why he acted like that. He finally confided in me (he actually started hyperventilating when he was trying to tell me and he ended up having to txt me what happened) about paying for sex when he was drunk with a transgender (pre-op) when he was 19, he's 22 now. He ended up spending a year depressed and went to counseling and felt suicidal and ended up going to brothels when he was drunk as a way of confirming that he didn't like guys. He said that he got his confidence back and stopped going to brothels and ended up doing the whole teenage thing of getting drunk and going clubbing and when he got lucky slept with random girls. He's never acted in a way that showed he was attracted to guys at all. He's always checking girls out, we have a healthy sex life, he's very touchy-feely with me. he's always complimenting me etc. After he confided in me I asked him if he was possibly in the closet and he got mad that I would ever even ask him that, but I was confused as to why he had sex with a transgender so I thought it was fair to ask. He looks and feels ashamed of it, What would be your opinion ? Was it a drunken mistake or was there a reason behind it?

Thanks

I assume that when your boyfriend paid for sex with the Trans Woman he knew what he was dealing with despite his being drunk? [To make it clear a Trans Woman is a woman but a pre-operative Trans Woman still has a penis and appears masculine in other ways despite the feminine/drag trappings.]

There are conflicted homosexual men who have their first experiences either with drag queens [gay men who are also transvestites] or with pre-op Trans women. This is their way of having sex with men while "pretending" to be with a woman, or telling themselves that the Trans woman is essentially female despite the biology. If your boyfriend has negative attitudes towards homosexuality for any reason, comes from a repressive, intolerant background, he may do anything not to feel that he is gay.

Naturally I can't possibly be certain of this guy's sexuality, except to say that most gay men are not obvious, that many are perfectly capable of having sex with women [for whatever reason], and that often there are no red flags. I would be less than honest if I didn't tell you that men who are genuinely and thoroughly heterosexual don't need to sleep with women or go to brothels to prove to themselves that they are straight; they just know they are. If this incident was just a drunken mistake, I don't think your boyfriend would find it such a big deal.

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