Savage Love

I'm a 24-year-old straight female. I just moved to a new city where I don't know anyone. So the other night I hung out with a 21-year-old jock from work. We went to a bar and eventually wound up back at his apartment where we both smoked pot. I was thinking he was a muscle-bound meathead so to shock him I told him a story about one of my male friends wearing a skirt. He kind of exploded and said, "You have guy friends who wear skirts? That's weird because I like to dress up like a woman and it turns me on and I really want to be a girl and I want to be pretty and I have these huge muscles because I'm fighting it and I've never told anybody this before and I can't believe I just told you and it's probably because I'm drunk and do you think it would be okay if someday I dressed up for you?"

I swear it was like that, one big run-on sentence. We talked for four hours and he says that he's not gay. He just wants to be a woman. The strain of living as two people is really getting to him, he said, hence the heavy drinking/pot smoking. I suggested therapy, not to "fix" him but to get to a place where it doesn't make him so unhappy. Now I'm not sure what to do. I can tell that he's crushing on me. He was before he told me his big secret, and now that he's confided his secret in me, his crush has intensified. I wasn't really interested in him to begin with but I must admit his admission makes him more appealing. I really do want him to dress up for me, I'm just not sure that I'm ready to deal with his reaction when I don't want to live happily ever after--especially if he sticks with the idea of becoming a woman. I'm just not sexually interested in actual women.

Would I be helping him come to terms with his identity by taking part in his masturbatory fantasy? Or would I be scarring him for life since I'm not interested in anything long-term? I'm afraid that if I reject him now he's going to think it's because of the cross-dressing.

Told Very Titillating Secret

 

There are two things you want here, TVTS. You want to see the muscle-bound 21-year-old dressed up in women's clothes for kicks, and you want to see the muscle-bound 21-year-old in therapy for his own good. So why not make dressing up for you contingent upon him finding a therapist?

Tell him you're tempted but you're not going to go there if you're the only person he can talk to about this stuff. If he wants to mess around and explore with you, fine, great, you're game for that. But that's all you're signing up for. You can't be his therapist and you're not making any commitments. Explain to him that if you knew you were the only person he had to talk to about his desires, you would feel obligated to continue seeing him even if you decided, for any number of other reasons, that the relationship wasn't working out.

I guarantee you, TVTS, that he'll have his first therapy session scheduled a half-hour after you get off the phone.

 

This past weekend I went out to a gay bar in Las Vegas. I consider myself a "hot" 26-year-old guy, but with a lacking sex life as I am somewhat shy and closeted. Well, several hours and drinks go by with not so much as a glance from another boy when who should walk in but sex on wheels himself. He was a dancer in a Cirque du Soleil production, 22, with looks and a body that could kill. We talked for a while and played some pool and decided to go back to my place. When we got home I ripped off his clothes and we began to play. Hours later, he was starting to fuck me with a condom on. Then about five minutes into the fucking, I realized the condom had slipped off accidentally and he was barebacking me. I immediately got up and asked him if he was clean and he said yes, even though I was too freaked out to continue.

Am I just a paranoid freak for worrying about my chances of getting some type of deadly disease from this encounter? I don't think he came in me at all, plus later he said he was bisexual and very clean. He was only barebacking me for like a minute or less. Please help, my sanity depends on it.

Screwed A Circus Kid

P.S. Yes, he did do some circus tricks for me...

 

If your sanity depends on hearing me say something like, "There's no way you could've been infected by that circus kid..." then my response is going to drive you out of your mind. There are plenty of hot, 22-year-old HIV-positive guys out there, just as there are plenty of hot guys who got infected with HIV under the circumstances you describe. Sorry, SACK, but there's HIV in pre-come, anal sex is the most efficient way to spread HIV, and not all guys who claim to be clean are telling the truth.

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