I had a girl i had met at a bar forcing herself to gag on my dick. At first it felt great, but as she kept going and continued to gag i progressively got limper and limper. Eventually she asked me what was wrong and i told her that she sounded like she was in pain from gagging and that it wasn't something that was necessary, i didnt want to hurt her. She immediately started crying, informing me that she was recently single but that her ex was the only guy that she had ever been with and he could only get hard and stay with her gagging. I would rather be kicked in the dick then have a woman (or anyone for that matter) crying at me nakedly. I suggested we switch to something else, and she started riding me reverse cowgirl, awesome, thought stupid naive me. Let me preface this next part by saying, im no stranger to ass play, im cool with it and encourage it, but it got weird. As she is riding me, she starts telling me to "hurt me in my ass." I literally have no idea what to do but am willing to do anything to not make her cry again. I started to spank her, and she tells me that she wants me to hurt her in her asshole? I literally have no idea what or how to do it at this point so i try to angle my spanks so that it hits her asshole....like an asshole karate chop, but done by an idiot instead of a karate master. She yells as me to put my fingers in....which is apparently what she meant the whole time, im a moron. I didnt have any lube and let her know and she told me to go in dry. I did with my pinky finger to make sure it would work, and she seemed to enjoy it, but asked for more, she wanted me to "hurt her" so i did 2 fingers, same thing...i basically fisted this girl. She came with a shuddering orgasm, pooped out my fingers and thanked me and left, it was my weirdest. TLDR: gagging girl cries because of my flacid weiner, then makes me fist her ass.