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dating coach for smart, strong, successful women Evan Marc Katz
How do you ask a guy friend to sleep with you? I used to date guys but figured out a few years ago that I would much rather be with women. I am 30 and have never slept with a guy. It’s something I want to do, just to try.Guy friends have offered. My issue is they think either I just need a good guy to convert me (it will not happen) or they want a relationship. I don’t think I’m that much different from straight women in that all I want is to be taken as I am and have what I say, be taken for what I mean.

Also, I’d really rather this experience be with someone I know, but at the same time, I keep wondering if someone more anonymous would just be much less complicated. I don’t quite know who best to approach, set the expectations and trust that I would like and then go about asking for thisfavour. J

This is why I keep blogging, y’all. And while I don’t profess to be a sex expert (hopefully my wife disagrees), I will do my best to earnestly tackle your question. No snickering. (Snicker) Okay, so you pretty much want the same thing that most men want, sexual experience, with no strings attached, with someone who is familiar and safe and attractive. Yeah, it doesn’t work like that. So let’s parse out your options, from least feasible to most feasible:

Throw a dart in a crowded bar, and you’ll hit a guy who is willing to sleep with you. If it doesn’t sound ideal because it’s, well, random sex understand that there are tradeoffs for wanting to use a man like a disposable human dildo.

Male prostitutes – I think Heidi Fleiss started a stud farm in Vegas. Seems a long way to go and a pretty penny to pay just to get laid, but, for a nostringsattached experience, you can’t beat a prostitute. (Correction: Heidi’s stud farm never actually got it up.)

Close guy friends -You already pointed out the problems. They think they’re going to convert you, or they actually want to date you. Both are fraught with danger because there’s an emotional set of expectations. Moreover, if these are close guy friends, don’t you think it could get kind of weird? Not just between you and him, but between you, him, and the whole crowd of people that know you. If there’s a guy that you actually don’t like, that would be perfect. Lots of women have pioneered the ‘sleep with someone you hate to watch him disappear from your life’, but I still think it’s too risky.

Random guys at bars – I don’t know how old you are, but I’m pretty sure it doesn’t matter. Throw a dart in a crowded bar, and you’ll hit a guy who is willing to sleep with you. If it doesn’t sound ideal because it’s, well, random sex understand that there are tradeoffs for wanting to use a man like a disposable human dildo.And this is where it really, comes down to you, J. Do you really just want to have the experience of screwing a man just one timelike the person who tries Ecstasy once just to say he did?

If so, I would think you’d go to a straight bar with a girlfriend, find the cutest guy you could find, and let nature take it’s course. Or, even more directly Go on Nerve.com, or Adult Friendfinder.com or SexSearch.com or even Craigslist Once again, it’s not hard to find someone to take your male virginity, it’s a matter of figuring out your comfort level with the whole process. If it sounds a bit cold, like Erica Jong’s ‘zipless fuck,’ well, that’s pretty much what you’re asking for. It’s certainly less complicated than being with a friend, no feelings or relationship to ruin.

…if any readers disagree with my advice, I’m all ears. Sometimes, the answers don’t quite come easily.

But if you can separate sex from feelings, and you’re not too creeped out by the anonymity of it (personally, I was) I say go for it. Talk to him first on the phone. Build up a comfort level. Use protection. Avoid snuggling. And make it clear that you’re out for a onetime good time. And if any readers disagree with my advice, I’m all ears. Sometimes, the answers don’t quite come easily.