Although I wouldn't consider myself a "high number guy" (16-20), I'll toss out my most disappointing. Super super nice girl; a skinny blonde that I dated over my summer where I went back to my mom's home in PA to study for the AZ bar. I hadn't planned on really dating and especially dating exclusively, but she was cool and was fresh off a relationship so we both knew it was nothing terribly serious and she knew right away it'd just be a summer thing. After a few dates I find out that, surprisingly, she's still a virgin. And by virgin I mean everything was intact. She was super religious and, as best as I could gather, dated basically the same guy in college/early twenties and they had agreed to wait for marriage (and apparently never went past 2nd base) but the relationship fell apart before marriage. She was 27 when I met her and, again as best as I could gather, she would date guys but her inexperience and lack of willingness to do stuff would scare most away. Her most recent relationship apparently ended because she wasn't willing to go all the way and her performance with other activities was subpar.
We slowly started trying things. Oddly, I found it enjoyable because I imagine the experience was similar to a high school dating experience. I was temporarily living at home and was broke and she was broke with roommates so we had to plan ahead and sneak around and stuff and, since I didn't date much at all in high school, I considered it a second chance given to me that my moronic high school self had deprived me of. Naturally, she was absolutely terrible at stuff, which would obviously get frustrating, but, again, she was hot and the experience itself was still seemed worthwhile. At the end of the summer she decided, with very little pressure from me (in fact, I had the "are you sure you want to do this? You know I'm leaving..." talk with her a couple of times), that she wanted me to be her first. I believe her thought process was basically that she was simply too old to find another virgin and that her current "status" actually hindered her dating prospects so she decided to start with a guy she liked but knew wasn't a long-term option. So we planned a night a few days before I left. Unfortunately, she got herself so worked up and nervous about it that she was a complete wreck. This was clearly a huge deal to her and I think she was put off by how little of a deal it probably appeared to me. She commented that I didn't bring flowers. She wanted to know whether, if circumstances were different, I would have said that I loved her. We had to talk that out for awhile. She also wanted to discuss some of my past experiences, which got awkward. During foreplay she was physically shaking. At initial penetration she basically screamed and then started crying. I stopped pretty much immediately and wasn't willing to go further. Unfortunately, she took that as a rejection which made her cry more. I still recall laying there staring at the ceiling having no idea what to say or do. It was so awkward.
I did keep in touch with her for a few months after I left. My understanding is that she actually met her now husband a few months later. I was happy for her.