Here's my situation:
I'm 24 years old. Never had a girlfriend. Never lost my virginity until last year, when I decided to sleep with a (fairly attractive) cougar, who an alpha friend hooked me up with. Technically, mission accomplished...the stigma's gone. But the sex was sloppy. I was incredibly nervous, no matter how much I tried to hide it. I was so nervous I couldn't even get a full erection. I've had a few other sexual encounters before, but they didn't involve intercourse, or in many cases, intimacy. I was nervous in all the ones where I wasn't drunk.
From grades 5-8, I was picked on ruthlessly, to the point where I think it scarred me for life. In grade 9, I started getting in good shape, and when I started fighting back, people wouldn't mess with me. I went from near the bottom of my gym class to near the top in a couple short years. That, plus the fact that I broke out of the firmly-set elementary school social order, enabled me to leave the realm of social outcast. While I had a cordial, largely neutral relationship with the popular kids in high school, I still found I got along better with the so-called "nerds". I just found some of the popular guys were big a$$holes.
Some people maintain the theory that love-shy individuals were neglected or abused during their childhood. I actually had the opposite problem. I have an overbearing mother who tries to pamper me way too much. My father was the counterbalancing force in that equation, but he wasn't terribly active in teaching me how to 'be a man' or how to do well with women. My parents met when they were 17 (she initiated) and have been together since, so I think it just has more to do with the fact that my father hasn't had to go through the same trials and tribulations as I have. Don't get me wrong. They're great parents, but they taught me how to be a stable 'nice guy', instead of the "man" that you need to be in order to tackle the world.
During my high school years, I wouldn't even flirt with a girl I liked. I would bottle it all up, release it to her in a big nervous speech, and be rewarded with the friend zone. I've since forced myself to break out of my shyness comfort zone, but it's still deeply embedded into my psyche. Then, by the time I drop a hint/flirt, or make a move, I'm already seen as one of those 'buddy buddy' kind of guys. The only times I have any sort of sexual success is when I'm either A) drunk or B) just don't say anything at all and get lucky.
Once, when I was a virgin at 22, I had an older woman ask me "Why are you still a virgin? Don't you have anything going for you?" I found that really insulting. I may be socially awkward and love-shy, but I still think I have a lot going for me objectively. I have run multiple half-marathons, competed in continentially-significant sporting events, bench more than my weight, have strong friendships (although not numerous), have a degree from one of Canada's most prestigious universities, and am in a post-grad program, living away from home independently. I'm sure I could be doing a lot worse.
But even still, I feel haunted by demons of my past, have a lot of confidence issues surrounding women and intimacy, and feel awkward in a lot of group social settings. Since the start of my undergrad, I've actively tried being a more outgoing person, with some success. Some people say they wouldn't even classify me as shy. But I still feel it deep down in many cases. I feel like I'm putting on a front in order to function in society.
The "male lesbian" description seems very fitting of me. I'm as straight as a pin, but I prefer when there's foreplay and cuddling, as opposed to just raw-doggin it and diving in. Comfort is key to performance. I'm terrified of rejection, don't take it well, and I'm thrilled if the woman makes the first move (at least drops a strong hint). From there, I have no problem escalating. But I have no concept of timing or "when the mood is right". I'm an absolute dunce with that sort of thing.
So what do you guys think? Do I fit the description of love-shy? Is this the forum for me?