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I'm 29, not truly a virgin (not proud of it but I tried prostitutes for a little while). I've never had sex with someone I really wanted to or who wanted me for anything but $$.
I've never had a girlfriend. I had some female friends that I felt were like a girlfriend but were really more like sisters except for the fact I also wanted to have sex with them.
I, too, am successful for my age, but not overly so. I own a home, nice vehicle, and people think highly of me. Still, I find I am insecure to the point of not being able to even fathom asking out women I find attractive. I cannot understand what they would ever see in me.
I'm short, heavyset (5'3" and 180lbs) but people at work say I don't look "fat" or "chubby." Women I like are generally younger, 18-26, thin, and bubbly.
I absolutely hate bars & clubs. I feel so out-of-place that all I do is stand near the wall and watch. People (including here) recommend trying social groups... Guess what? If I liked the idea of the group I would already be in it.... When I try those (singles groups, church groups, etc) I am as out of place as at bars.
So... you are not alone. The right person who can take you and me out of our social shell will come along sometime. Until then, masturbation provides a safe relief from the urges. Just push your own envelope a little bit once in a while.
I have a lunch date with an older woman (35) next week. She's short, not thin, but not fat. Not gorgeous, but certainly not ugly. A few years ago I would not have given her a second look, but I now know her a little bit and she has a great personality and we make each other laugh at work. I was recently set up on a date with a Thai girl. She was pretty, tall, thin, and friendly, however we just didn't click... no joking around, nothing in common.
While not the "trophy girlfriend" we're trained to chase by TV and magazines, this woman from work makes me feel good about myself when we're together. Hopefully I will have the guts to ask her to dinner/movie/hike/ whatever, if this lunch date works out.
Good luck, from another sexually frustrated guy... Who wishes he was still an unwilling virgin instead of regretting paying for it just to get the short rush.
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