The fact that he was a grown man who still called himself Timmy should have tipped me off that this wasn’t going to be the most satisfying experience. So Timmy was a fairly sweet, if dim guy and before we had sex he told me he’d had sex with a few girls, but only one time each and he didn’t know why. I was all, “That’s so weird! You’re totally cute, let’s have sex twice today.”
Half an hour into fooling around, I figured it out. Not only did he not get hard at all, it seems that no one had ever told him that you need to in fact be erect before trying to penetrate a woman. He kept holding his tiny, limp dick and trying to kind of…just…flop it inside of me, I guess. I tried my very best to, um, rectify the situation and get things really going, but he kept saying, “What’s wrong? Why won’t you just put it inside you?” So I just sort of…shoved his flaccid penis inside of me and he started to moan like it was feeling really good for him. Then it promptly just fell out.
I remember how sad and floppy it looked lying against his leg and then how pitiful the whole effort was as he started to rock against me, gently thwacking his droopy, listless penis between my legs as though I must be the luckiest girl in the world. Needless to say, we did not have sex more than the one time. I wonder if he has since broken that streak.