So my bf (20) and I (19) are currently staying in a aibnb. We are staying there for 3 nights. The first evening, we made a bet. If I won, I would get to pick our vacation for the summer. If he won, he could fuck my ass anytime he wanted until sunrise. The bet was pretty unfair because he was sure he would be the winner. We had a bottle of vodka : the first one who couldn’t continue to drink would lose. Well, I won.
We do this sort of bets pretty often. Usually I win and we go to a restaurant, sometimes I lose and I get fucked really hard. Tonight we made another bet. He would get my ass. I would get ice cream (paid by him). I had 10 minutes. If I succeeded in making him fuck me, I won. He set up a timer and I went down on him just a little. After that, I asked him to get on top of me. His dick was on my pussy, just at the “entrance”. I started playing with it, mastubating with the tip and giving him a handjob. I talked about breeding and did everything he likes but it didn’t work. I lost the bet.
He didn’t waste any time and has soon as the timer went off he put my legs on his shoulders and started to penetrate me. Anal isn’t something we do very often so it was very painful. He stopped before entering me completely and asked me to get in a pronebone position. This time, his whole dick went inside my ass. He wasn’t soft. He went as fast and deep as he could. At some point I started crying and I made so much noise..Sometimes, I would jerk away because of the pain but I would always get back in pronbone or on all fours. I think I tapped out after a while but I felt him cum in me after fucking my ass even harder.
It took me a few minutes to regain my strength. It want the end. After a few hours, we went to bed. This time, I was the one who asked him to fuck my ass. I still can’t say if I love or hate it, but I’m addicted to the pain and feeling it gives me. I asked him to fuck my ass in front of a mirror. Watching my tits juggle while he just destroyed me was very hot. My bf was alternating between my pussy and ass and was crying out in pain and in joy at the same time. Towards the end, I fingered myself and I could feel his dick fucking my ass, I even tried to “stroke” his dick with my fingers.
After a few minutes, he filled up my ass again. His sperm was very warm and I’m still feeling it leaking out as I’m writing this. I asked him to help me finish and he told me how much of a slut I was while I touched myself. I really think I’m addicted to anal now.
Source: reddit.com/r/gonewildstories/comments/zqa0tr/how_i_lost_a_bet_with_my_bf_and_got_my_ass_fucked