Active Dating and Sexual Experience

[expectations]

I'm a 26 year-old man, actively dating through OKCupid, and have been on a few dozen dates, overall. I'm a fairly healthy, tall man, and I love talking to new people. So I do pretty well on a lot of these first dates. A pattern I've been having trouble with, however, is when my date is more eager to push things right to sex than I am. At least three separate ladies seemed to have been turned off that I wasn't Casanova when given the chance. (For example, one lady who had me over at her cousin's place, and we slept in the same bed, but she was very firm I shouldn't do anything. Judging how things went later, and the fact that she had me in her same bed, I think, if I was a bit more aggressive, that would have been different.)

I've never gotten to a moment with a woman where the two of us were equally comfortable with having sex. My longest relationship was three months. Sexually, the farthest I've gotten with a girl was penetration, but we had to stop because she wasn't comfortable enough with it. I've either been the one slowing things down, unsure if I want to take that step with that person, or I've been the one who was way more ready to go than my partner. I have friends who tell me to "just go for it" and I don't think it's that simple. It's very frustrating, because, for many people, a big part of how you come off to other people is your sexual confidence. It's been like a job search lately, where the dates I want, which might help with developing experience, don't happen because I don't yet have that experience.

Anyway, I was browsing OKCupid today, checking out answers given to "match" questions, and this was the most naked I've ever seen it:

http://screencast.com/t/ybi6IaQxk

I've seen this attitude on a large number of profiles, but this is just right out there. Do I need to go hire a prostitute to be eligible to date? Sometimes it seems like it.

All of a sudden, though, I'm reminded of the part of the new show opening: "I don't think I have what the woman - who's not right for me anyway - wants." I just have a hard time keeping up confidence when people like this imply that I'm forever behind everyone else. Does anyone have any insight or experience on this? Is wanting to find a good match, while also getting good sex experience, incompatible?