I haven't had sex in more than three years. I am going out of my freaking mind. One of my New Year's resolutions is that I must end this dry spell. I have a friend with whom I would like to start sharing some benefits. How do I go about this?
posted by anonymous to Human Relations (38 answers total) 5 users marked this as a favorite
Straight lady here. Even though I greatly prefer relationship sex to one night stands, I don't want to start a relationship right now. I am too busy, and I don't want my life plans to be derailed by a boy. I think friend-sex is the way to go for me and I'm uncomfortable with casual sex with someone who is not a friend. (Done it before; it was not at all satisfying even though it was fun, safe, and I don't have any hangups about having done it.)
So I've become friends with a guy to whom I'm really attracted. I like him as a person and as a friend, and though he is perhaps not conventionally attractive, I find him so freaking hot I want to tear his clothes off and ravish him on the tables, the floors, anywhere, everywhere, every time we talk.
He is not "relationship material". He's 15 years older than I am (I'm mid 30s, he's late 40s). He describes himself as a "confirmed bachelor"; as I understand it his previous relationship ended because she wanted to get serious. In fact, according to my definition of "serious relationship", he's never had one (he thinks he has, though). He doesn't want kids and I do. He can't leave the area, and I have to. He's white and I doubt he's ever dated a black girl, which I am. His school district wasn't even integrated when he was a kid. (He's not racist, at least not any more than the average American, including myself, but according to him, his family is.)
Oh, and he's my boss. He doesn't supervise me, but I ask him for advice and he could, for example, get me fired if he wanted. He would never do this -- he's mature enough that his ex is still a regular customer, for example. But if I stopped working there, it wouldn't be the end of the world. I'm part time and not dependent on the job and would just devote more time to my business.
So overall, he doesn't actually work as someone I really want to date, and I'd probably be over him already if I were looking for "the one" as opposed to "right now". But his unavailability actually makes me want him more -- there's a huge appeal to the ease of cutting ties while remaining distant/casual friends when I move away. And he is so hot. It seems like a win-win. He gets to bone a younger woman with big tits who doesn't want to commit to him -- what's not for him to love about this situation?
Also, I should add here, I think he is attracted to me, but there has been no overt confirmation (no kissing, etc). I do know he likes me as a friend. We hang out outside of work, just the two of us, every other week or so. At work, we're pretty professional; in fact, I've noticed that the more people are around, the more he avoids me. For example, if I'm sitting somewhere, he might come hover and start a conversation with the person I'm sitting next to, but he won't sit down until I leave. But if it's just the two of us, he'll come sit right next to me.
Outside of work, we hug regularly, and have come close to snuggling (it was awkward). Then there was that one time when we briefly held hands (more awkward than anything I've experienced since middle school). I cannot imagine he would make the first move under any circumstances. Even though I feel I've made it clear that I'm attracted to him (though I have perhaps also sent mixed signals accidentally), I think he would worry about being inappropriate. Also, he knows I ultimately want a serious relationship and kids (because before I wanted to sleep with him, we had a few amazingly good serious conversations, which we still do.) Since he's older and was conservatively raised, I'm afraid I'll turn him off by being too direct. I can't even imagine inviting him over to my place because I feel like he would worry about it being inappropriate. We've always hung out in public.
He's an alcoholic, though he's been sober for years, so the no-fail move that's started all my relationships -- we both get drunk and kiss -- is out. I rarely drink these days myself anyway.
So, how the heck do I make this happen? Should I have a conversation with him or just kiss him? Would it be best to bring up the subject/make a move before one of our times hanging out, or at the end? What would I say, either before or after we kiss? I don't find guys I want to sleep with that often these days, and I'd hate to mess this up, because like I said, I *really* need to get laid.