Would you try to....

Originally Posted by Ramboner

....hookup with your best friend if they showed up to your place in drag and looked really, really hot???

I had this dilemma last Halloween when one of my best friends (who is male) crossdressed as Sarah Palin and I couldn't believe how feminine and sexy he looked. He certainly has soft, feminine qualities but I never assumed he would so attractive as a CD. The thing is...he's straight (at least openly). I always felt conflicted about telling him how attracted I am to him (especially that night). He's not homophobic or anything because he knows I'm part of the TS/TV community but it would probably turn our friendship in a weird direction. He has seen me crossdress countless times and I've always wondered if he is attracted to that side of me.

It's always nagged at me...like the "what if"...What if we're partying or hanging out and we're both kinda drunk and I tell him and he tells me that he has feelings too? Or I try to kiss him and he complies?

If I tell him and he gets weirded out, it sucks. If I never tell him, I may never know the truth. Catch 22's are bad enough. It's horrible when they involve 2 close friends and sexual attraction.


Sorry if I'm a bit long winded...I'd like to know what you guys have to say.

Such a hot f'n thread.

What feature of his in that outift turned you on most? Does he ever joke around with you about how you look?

I bet if he was horny enough he's love to fuck your face and ass bb

[merelypink]

does i touch you alot like pats or any excuse to touch you?

[tylergib]

Thats a properly unfortunate dilemma to be in.

Me, and easy to say this cos I aint you if ya get me, is that if he knows that your into CD/TS etc and you know he knows, lol bear with me, then surely he must have known the sort of reaction/feeling he would have got from you in dressing up super hot.

Which leads me to assume he could be coy and shy about asking you the question? Maybe just ask him? Not drunk tho, causes way to much complications by itself.

Better to have tried and regretted than to regret never trying???

[transjen]

I have a rule i will not date or sleep with a guy who knew me as Jeff, I just can't do it Jennifer

[violet lightning]

It sounds like your friend might be open to something. He is "straight" yet is still crossdressing and from what you say, is putting some effort (sucessfully) into looking feminine, if only at Halloween.
Maybe you could just say something in a joking way like . "wow, you actually looked very convincing that night,...I was starting to get a little attracted to you!", and then gauge his reaction. If he looks intrigued, happy, etc, great, keep going. If not, just laugh it off as a joke and quickly change the subject.

[Ramboner]

hmmm....I've been reading everyone's replies, some of them very useful. I'm still mulling over what to do. I don't want to make a decision without committing to it 100%. If I'm going to take the leap and tell him, I want to be able to live with the fallout.

[richardallen64]

I agree with the last post. If he's crossdressed and looks hot (i.e. not an ironic ugly guy in drag sort of way), then he is at least curious. Start with something you can recover from like just saying that he really looked convincing and if you saw a girl like that. . . .