Please help me not be the next 40 year old virgin!
I'm a guy pushing 30 and I'm still a virgin. I'd like to change that. This question is not about how to meet women or get them to sleep with me. It's a little more, um, practical than that.
I've only done more than make out with 3 women. As a result, I'm really insecure when I'm with a new girl, which leads to performance anxiety.
The inexperience stems in part from not being very assertive when I was younger and having self-esteem issues related to my weight. I'm not perfect, but those are no longer holding me back in terms of approaching women, flirting, or dating. But now the inexperience is perpetuating itself.
Recent example: I had gone out with this girl a handful of times and we made out a little. After one night of lots of drinking and dancing, she came back to my place. Both of us were really turned on all night, things were going well. We're in bed, lots of foreplay, still very turned on. As soon as she actually reached down and started to give me a handjob, I went limp. She was very attractive, and I was very interested, so that wasn't the problem. We talked a little about me being inexperienced, laughed it off because we were both wasted, then went to sleep. Same embarrassing scene the next morning! But sober and without a good excuse. That's a blow to the self esteem (not at all the blow I was looking for).
Neither of us was looking for anything super serious at the time, so when I wasn't really up for the benefits part of friends-with-benefits, that little fling went away. And I'm starting to freak out about repeating the above scenario with the next girl... and the next....
In the ideal situation, I'd be comfortable enough with whoever is in my bed to talk about this, and she'd be cool and patient so taking it that slow wouldn't be a problem. But it doesn't always work that way. I don't necessarily want to have the "I've only been with 3 other girls and I'm still a virgin" conversation with every girl I might sleep with. And I don't necessarily want to wait until I find my soulmate to have sex. So I'm looking for tips to get through some future casual hook-ups. All my plumbing works just fine. I masturbate regularly (but I don't think that was an issue in my last encounter... I could've hopped into bed with a loaded gun and not been able to pull the trigger that night).
What can I do, mentally or physically, to get past this roadblock? Any suggestions appreciated.
2. Relax - it's really not a huge deal that you're a virgin unless you make it a huge deal.
3. No really, stop thinking in terms of this being a race to lose your virginity.
4. You speak of an ideal situation where you want to be comfortable enough to communicate and take it slow - only then you put yourself in the exact opposite situation. Your brain and your penis aren't playing on the same field. I'm guessing that if you actually put yourself in your ideal situation that you will be much more comfortable.
posted by fluffy battle kitten at 3:52 PM on July 21, 2007