Aight, so if you people are in for a damn good horrible first sexual encounter story, settle in.
I was blazing with this really chill dude from work, we'll call him Tim, who used to hustle all sorts of drugs back in his day but ended up having to take care of his dad because his wife left him. The guy was 24, and this really fat chick had been pursuing him for years but he wasn't attracted to her and wanted nothing to do with her. He was at a party with her and her extremely fine friend, who was telling him about how she was going to take him back to his house and show him an amazing first time and all... but her fat friend got pissed because she'd been pursuing him, and so long story short, they had a huge argument and the hot one left.
The fat one was all pissy, and sarcastically told Tim that she'd be sleeping alone tonight because he clearly wanted nothing to do with her. This was where he made his mistake... he right there decided that he was sick of being the oldest virgin in all of America, and took her upstairs.
She was noisy, obnoxious, loud... she came but this guy was not attracted to her, sort of pissed at himself for getting himself into this, sort of pissed at her for being so loud and annoying, and pissed to hell that she was so unattractive he wasn't even enjoying his first time having sex. He was so frustrated he asked her to get on top so he could think about the groceries he had to buy the next day. Not even joking.
Finally he decided it wasn't going to happen. He wasn't going to finish, and she was pissing him off. He asked her to get off so he could go to sleep and then retreated downstairs to the couch as soon as she started snoring.
The next morning, Tim's dad found him on the couch and started complaining about some loud, obnoxious, fat bitch who Tim's cokehead brother must have been fucking. Tim decided to let it be and hope his dad didn't notice that his brother wasn't even there. The girl enters the room from upstairs where Tim sleeps right around then. Tim's dad shook his head, looked at them both, and said "I'd expect that from your brother, but never from you".
The girl sits down like nothing happened, Tim's tweaking out and angry as all hell, and she starts writing in this book. He asks her what she's up to and she tells him she's adding him to her list of the guy's she's fucked. He looks at it... 28 names. 20 of him were friends or dealers of his. The 4th name was his brother's. Whatever he entered was not clean, very dirty, and more importantly had previously been occupied by nearly everyone he knew. He asks her to leave.
She stalked him, creepily and hardcore (hiding in bushes kinda shit...), for five weeks after that until a concert they both were at. When she started hitting on him he stood up in front of everyone they knew and started yelling at her about how it was a drunk, shitty mistake and how he would never have fucked her "wider than a mack truck" pussy if he wasn't desperate as hell because he was a 24-year-old-virgin.
Talk about the worst fucking experience you've ever heard of haha. Sorry it's so long, I love that story and I'm still tripping a little so writing is fun as shit.