[M]y bet did not end as I expected. [F]

It was the night of my work holiday party and a girl I was dating was going to meet me before hand for some pre party drinks. We were at the bar and there was some sport game on the tv. We didn’t care much about what was on (I don’t even remember what sport it was) but we decided to place a bet on it. Her side was if her team won, I had to take her to dinner. My side was if my team won she had to give me roadhead. Needless to say, my team won.

We walked over to the bar for my work party and meet up with some work friends. Drinks were flowing and the girl I was dating turned to me and said “instead of roadhead how about I blow you here.” I was immediately interested and I asked her the plan. She wanted me to head to the stall and wait for her there. I head into the bathroom and wait. About 5 minutes later my girl got a clearing to come in. She opened the stall door and got right on her knees. You could hear guys walking in and going to the urinals. She never stopped. She took my cock deep until I came in her mouth. She cleaned herself up. Waited until we had an all clear and we walked out like nothing happened.

[MF] Accidental Ass to Mouth

So, a few of you liked my last story about when I accidentally put it in a girls butt and she gave me the green light but quickly asked me to stop. I had a lot of questions if I ever got to do anal. I didn’t with that girl but here is a story with another girl.

I was in college and was messing around with a girl from home who was going to a college a couple hours away. She was begging me to come visit so one night I made the trip up. That night we went out to a party but came home pretty early to fuck. We were both a little drunk and she told me to put it in her ass. I was happy to do so. I fucked her ass and shot cum on her back. We fell asleep quickly after and woke up a few hours later and were both ready to go. I went down on her and got her to cum within a couple minutes. She decided to return the favor. She blew me pretty good and took my load. It hit both of us at pretty much the same time that my cock was in her ass a few hours before that and I never had a chance to clean off. She kind of shrugged it off. Not much we could do at that point.

[MF] Accidentally put it in her butt, she said keep going.

This story isn’t going to be as great as a happy ending as the title make you think.

When I was about 19 I was still living with my mom. We had a large family so me and my step brother shared the basement. I would often bring girls over and we’d lay around and watch tv. My step brother never got the hint so he was always around. One night I had a gf over and we were all watching tv. My gf clearly wanted to have some fun but my step brother was not getting any of my hints to leave. At some point while watching a movie he falls asleep. We are spooning facing the tv and I feel her reach back and start to rub my cock. I started to return the favor and the next thing you know both our pants are pulled down just enough to get some action (we had a blanket covering us). My cock was sliding against her pussy which was extremely wet. I could tell that she was ready for it to go in so I line up and started to put the tip in. This is when she stops me and tells me I got the wrong hole. I apologize and she says don’t. Let’s try it. Now I’m no porn star but I have a decent sized cock about 8-9 in and it’s as wide as you’d imagine a cock that size to be. My girlfriend was a tiny thing. Anyways, without lube orange only using the wetness from her pussy I put it in. She immediately starts crying in pain. Trying not to make any noise since my step bro was sleeping on the bed across the room. I pull it out. Make sure she’s okay, which she was and she asked me to still fuck her (just not in the ass).