Freshman year of college, dorms, a girl from the hall across the way was over at my friends dorm, we started drinking, my friends left the room for us, we're making out. She is moist to the touch through the fabric of her jeans, she reaches to my crotch, where my zipper is, and felt part of my bulge, she traced it all the way over to where it ended near my pocket as it laid across my leg, she squeezed it, looked up at me startled and shocked, and stopped then and there. It was over, so I left. It sucked that time.
Different occasion, my ex was very petite, and had trouble accommodating my dick sometimes. More than once, we would be going at it, and I would be inside of her, she would usually get off within the first 3-5 minutes, then again after about 10, and if I took more than about 12-15 minutes to cum, she would have to stop me because it became too painful for her, "You're rubbing me raw." She would say. Sometimes she felt soo bad for having to stop she would try to keep going, and tell me to just keep fucking her, she would place a pillow over her face to cover her expression because she was in too much pain but wanted me to finish. Those occasions weren't too fun. But the routein of going to the kitchen to get her advil and an ice pack every time after we had sex was a confidence booster in a twisted way, and even more fun when her roomates learned why I would always go get them for her...