I’m a hs senior and me and friends went to a frat party at a college near where I live. I met a guy there and we danced for a bit. He was 22 and really hot. Tall muscular handsome face. Apparently is kind of a big deal hockey player at the school. He was being pretty aggressive/handsy but I didn’t mind. I was really turned on. Eventually we go upstairs to his room. I get on my knees and I begin sucking his dick. It was huge, definitely the biggest I had before. Then he puts me on my hands/knees on his bed and comes up behind me. I feel his cock press against my asshole. I’m like hold on what are you doing. He said something like if you want guys like me to like you you have to do this. And said he’d just go find a different girl.
Reluctantly I was like fine you can do it. It took awhile for him to even just get the tip in my ass. It hurt so much especially as he began to slide it in. Not only hadn’t I done anal but again his cock was huge. I was really struggling and whimpering. He was gentle at first but then began really thrusting hard. I was literally crying part of the time. He fucked me in a few diff positions. I’d guess it lasted about 20 min total and he cummed in my ass.
I feel kind of conflicted. I’m glad I tried something new. And it was fun being with such a hot guy. And it was kind of hot how dominant he was. But again it really hurt a lot.
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from Gonewild Stories https://www.reddit.com/r/gonewildstories/comments/yqy4f2/my_18f_painful_first_anal_experience/
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