Some background: I am bisexual but more into women, and I've been out to my family since I was 12. I went to high school in a conservative Midwestern suburb, so I didn't really come out at school. When I came to college, I became pretty active in the gay community here. I'm a senior now and I moved into my current (university owned) apartment in August. My friend told me that my roommate was a lesbian, and I was surprised I'd never met her. The first Thursday, my roommate, her friend, and my friend were at my apartment drinking and smoking. I found out that my roommate (J) had just come out as a lesbian. After my friend had left, J, her friend, and I sat outside smoking. Both asked about me, and I told them that I tend to hang out with gay guys and don't really know how to flirt. Both of them started telling me how cute I was, especially J, who kept telling me that we should hook up. I was drunk so I told her I didn't know if hooking up with a roommate would make things awkward. She kept talking about it, saying that when our other two roommates were gone, we should get it on. She said "just let me know." But I wasn't sure how to feel. The next day I woke up, turned on by what she had said, and decided that I want to have sex with her. We've been friendly since that night 3 months ago- my friends know her, and her friends know me. We see each other at parties and occasionally smoke together when we're home. The last 2 weeks, I've been especially turned on by her presence. The thing is, she's friendly, but I don't know how to bring it up. If there's a dynamic, she'd be the "butch." I'm incredibly shy around people I don't know well. My friends were trying to push me to talk to her at this party the other day, but I'm just that afraid of rejection. I don't know if she still wants it! Does anyone have any advice? Thanks in advance and sorry this was long! Oh, and also she has a lot of sex, while I haven't had sex with a woman since high school because of my obvious ineptitude. And she mentioned (in passing) that she was still single the other day.
just go for it - she sounds relaxed about the idea and at worst you could always change rooms later if it doesn't work out long term. Useful to have a fuck-buddy and it doesn't sound like she would want it to be monogamous. Even opens up the possibility of future three-sums, though I suppose it might make it awkward if you want to be alone with another partner sometime in the future - you could always use their room? Simon:sunny:
Hooking up with a roommate can be rough, but if you guys just have fun with it, it can be a blast. She does sound pretty laid back. Maybe have her "accidentally" find you naked or masturbating. You can tell her reaction from there.
If it's too awkward to say, "remember when you said we should we should hook up sometime - well if you still are down for it I am.", then the accidentally naked thing sounds like a good idea. You could be walking to your bedroom after a shower with your towel over you shoulder, or if it's credible go to the kitchen to get something and say you didn't know she was there. She'll say something and that's a good conversation starter.
