31 married now. Was sexually aware at 13 (liberal parents help), but I was way too introverted/nerdy to get with girls in high school. I wanted to get anything I could in college, but is harder than it seems (at least a tech school). Had girls screw with my head all through college - me being gullible but without assertiveness. I also had this thing about wanting my first time to have some meaning - which I guess for me meant a girl I thought was cute and not a blacked out drunk hook up - easier said than done. Masterbation was a routine. I was also scared of STDs, maybe too scared.
After zero luck (and almost being pressured into a 4guy-1girl five-some while on potent shrooms in Amsterdam), I went to the red-light district and had "sex" with a cute girl I found there. I say "sex" because although technically that's what it was, I couldn't get off, and she gave me extra time too. She said I needed to get with a regular girl. This was junior year of college.
My first girlfriend was a very religious girl senior year of college and we would get into some heavy petting over the weekends, but it didn't progress how I wanted and she couldn't deal with her feelings (touching/orgasming v. Catholicism). Took way to long to end, but as much my fault as hers.
Enter grad school. Went to a state school with a large California influenced undergrad (very attractive undergrads). Had sex for the first time 2nd year there - was at a house party, was chatting it up with a very cute girl there and noticed after an hour or two that we were still talking and what do you know - she lived there, so we had some fun in the bedroom and I stayed the night. Actually didn't have sex that night, she found out I was a virgin one or two days later and we had sex that night. We broke up a few weeks later as I got clingy, but it was like a great weight had been lifted from my mind.
Had a couple one night stands after that, couldn't even get hard at least once. Met my wife a few months later. Was super comfortable with her immediately. Great thing about love sex - mistakes aren't as critical, communication is so much easier, and the knowledge of sex with someone you know means that both of you can enjoy yourselves more. Especially if you're open about potential positions, "order", and boundaries.
I can imagine one-night-stands now, and there is so much risk involved. Is the risk enticing and arousing enough to overcome the barriers? Sex with my lover - I know what I can do to her, what she wants me to do, no STDs, no pregnancy worry (especially as we are trying to have kids), no body image issues, no being kicked out/having to kick someone out afterwards. Helps that I get massively turned on BY turning on women. Of course, maybe because I didn't have one-night stands earlier, sex is on a higher pedestal for me and less selfish, as who cares about the partner if they are going to leave the next day. Selfish sex for me is masturbation, sex with another person is for them (and I get the benefit of reciprocation).
Plus, it's hard to have simultaneous orgasms with someone you don't know. That's the benefit of love sex.
