I was with my boyfriend for a year when I began suspecting him of cheating when I found women's clothing that was mine. Long story short, I found out through extensive Internet searching that he owned a porn site where he is the main attraction as a cross-dresser and people pay to watch him have sex dressed up in MY underwear and dresses in my home. I had no idea and was shocked. I found out next that he was advertising himself as a hooker who cross-dresses and caters to men for $200. After I moved out and confronted him he said he wasn't gay and was just interested in making money. The thing is, he has his masters degree and he lives off his rich parents. He had the gall to tell me that the fact that my daughter who is disabled stresses him out caused him to snap and "indulge in selfishness". He had the website for a year before I met him and admitted to paying very passable pre op transsexual hookers for sex up to three years before we met. He tried to explain since he had sex with them while he was dressed as a man and they looked like beautiful women it was not "gay sex". Furthermore he said when he was prostituting dressed as a woman having sex with men that also did not constitute "gay sex". In the past two months since I've left he has been actively trying to get back together with me saying all that was a phase and he was over it. I then found out he got arrested 30 min. after we got off the phone for prostitution by Vegas vice. He was still doing it! And now he's a " changed man" and is livid that I won't accept he's straight and move back in with him. I am heartbroken, and confused. But I also know I can't get back with him obviously. What I want to know is if he has a severe disorder, if he's delusional, and why he is adamantly denying being gay and is he typical of "closeted men"?
his particular obsession in dressing was thigh high boots which was
consistent through out. I am so confused why he'd pursue a serious
relationship with me when he was doing all of these secret activities?
Should I try to help him....? Forget he existed?? Help.
My advice is to probably forget he existed, and not because of his extra-curricular sexual activity, but because he's involved in criminal activity, is a liar, used your home and clothing for porn activities without your knowledge or permission -- the yuck factor goes on and on. I'm a pretty open-minded guy but this character sounds pretty unsavory in many ways and, yes, delusional.
Now on to other specific points:
Cross-dressing men can be and often are heterosexual. [Most gay men have absolutely no interest in cross-dressing.] However, the fact that he's advertising for sex with men [and whether for pay or not for pay is irrelevant] is an altogether different matter. Also, most pre-op transsexual men still have penises, and I doubt if a 100% straight guy wants to have sex with a "lady" with a dick. [Let me make it clear that I believe post-op trans-women are definitely female -- and perhaps even before the surgery -- but most genuinely straight men would be turned off by the male genitalia and other biological factors.]
So this guy can argue that he wasn't indulging in standard male-male sex and therefore it wasn't gay, but it was decidedly "queer" [queer now being another acceptable term for the LGBT -- or Lesbian Gay Bisexual Transgender community]. And I find it hard to believe that a man who has no attraction for men would want to have male sex partners even when he's dressed up as a woman. At the very least, he's bisexual [which doesn't mean his preference can't be men, making him essentially gay] and he is being disingenuous, or, as I said, delusional. It's also possible that he's transsexual himself, which can be very confusing for someone who hasn't yet accepted or acknowledged it, and he may honestly be confused as to his basic orientation as well.
While it's perfectly okay for you and others to be compassionate for and understanding of his confusion and "kinks," it does sound like he has a lot to work out in his own mind before he's ready for a relationship, and it may be that it would be more natural for him to be with a man. He's typical of closeted men in his denial of obvious homoerotic acts with other men, although the porn web site and cross dressing is not so typical.
In conclusion, let me just say this guy has a lot of issues -- and not just the sexual ones -- and it doesn't make you a bad or bigoted person if you don't want to deal with them. Relationships are tough enough without adding quite so much drama.