I don't have much compared to the rest of this thread. But I can't fall asleep, so I'll waste my time posting. Warning: this post will be much longer than needed. Don't even waste your time.
Now I'm not experienced at all, so that's why my story will suck. It's more just WTF, than painful. Anyway, back in junior year of high school, I had no experience with girls at all. And I'd like to think I'm not an ugly guy, but I never really cared to bother and plus I was a pussy. Now I become partners with some girl I barely know in gym badminton, she's pretty cute, as is her friend. It's weird because even though we had gone to high school together, I didn't know either of them at all. Anyhow, they both get on my case about going to the junior prom, espeically my partner. I really wasn't even planning on going, but she kept getting on my case. And as we played badminton for a few classes, I started to like the girl a little bit, and my friends and I were actually thinking of going to the junior prom, so I was thinking of asking her, but before I can, one of my friends (at the time we weren't that close of friends) asks her. So I'm like, ah shit. But then I end up going stag and the whole time I'm there she's hanging on me, making me go out and dance. So it made me pretty happy to have a girl show such an interest in me. I asked her out shortly afterward and we went out on one date, of course to a movie, but I couldn't bring myself to make a move. It didn't help that I knew she didn't have any experience either. Next day, she calls me up and breaks it up. I'm just like...ah shit, but I didn't really care too much. I didn't see her or talk to her all summer.
Once we got back to school, I started talking to her again and it was the normal stuff. But then after a month of two she starts being really friendly again and then some girl tells me that she still likes me. So now I have this in my head, and I guess I also had some feelings for her too. We start hanging out a little bit. One week I remember we hung out a lot, and it was actually her getting me to go over her house to help with her with math. But I couldn't try anything because her parents were right there all the time. Then that weekend I pick up her and her friend up and we go to her house. And then we get bored, and it comes out that she had never seen Dumb and Dumber, so I drive home to get a copy and we start to watch even though its already 11. Her friend leaves at around 12, so it's just me and her, but I never tried anything. Then I think that week she like calls me to come over one day and we talk about stuff like how we both like each other, but we're both really timid about the whole deal and she says that she really doesn't want to go out or anything either though she likes me. So at this point I don't know what the fuck is going on. I don't even remember the whole deal after this, but one night she says we should go see a movie with a bunch of people, but we end up not being able to get anybody, but she says she still wants to go, just me and her. I'm left wondering if this is a date or not. So we go to the movie, and towards the end, she grabs my hand, but no I still don't try to kiss her. So we just hold hands for a bit. And then when I dropped her off at home I just gave her a kiss goodnight. But I'm left thinking, eh maybe this will go somewhere. And I had really started to like her a lot. But then she just pulls the same crap in a week, saying that she doesn't want to go out and all that crap. I actually try holding on, I told her so much crap. Didn't work. This was before I knew of CubsFan's dating tips. Anyhow, I'm just left in a state of disbelief. I never had that much confidence before this, but then after fucking up with her twice, I was just like, "Wow I suck."
Present day - I'm still friends with her (yep I'm a bitch), but really only because she became friends with a bunch of my friends. But now she's a bit of a slut who likes to give my friends drunken blowjobs and I'm still an inexperienced no confidence bastard.