Straight Male / 28
Great Bet
I play in a coed pool league in several bars around the city city once a week. On one of the other teams there’s a really cute brunette That sometimes flirts with me but believes she is a very good billiards players. She was nice enough but it’s a bit of a tease as she has a perfect body and the cutest little hard butt. Our teams usually switch out wins. But I know she has thought she is a better player than me. As I sometimes play for money I do not play my best game in a coed league..
But I got lucky and ran into her at a local pool hall. She was by herself I’m just practicing. We started talking and shooting around and she continued to tease me and rub up against me. We weren’t really playing seriously and at some point she said she was tanking because she was hoping to get somebody to play and beat them for her rent money for this month because she short. I asked her how much she needed and she said 1500.
I felt a stir. Maybe this was the way to see how far the flirting would go. I told her I would play her best two out of three. If she won I would give her the 1500. She laughed laughed and said that was easy money for her because she had seen me play so much. She said I was basically just giving her the 1500 which didn’t seem fair. I told her I Was a little better than she thought. She said, well OK, obviously I don’t have the money so what do you want if you win.
Sex I said. If I win we go right to my house now and have sex. She again laughed and said you’re betting you could beat me to the tune of $1500 just to have sex with me? I have thought you were cute and tried to hit on you. I likely would have done it for free just because I think you are cute.
I said thank you I said OK then let’s make a little more interesting? She just looked at me. You win two out of three and I pay your rent I win two out of three and we go home and have anal sex. How is that deal?
She said well, I have never done anal sex and have no intention of what you’re not gonna beat me anyways so rock ‘n’ roll. We shook hands. And I racked the ball and let her break first game. She played a bit sloppy but good enough that I let her win. She laughed and said I could not believe this bet. I said well the stakes are higher for you, right? She was not dumb and gave me a look like she thought something might be up I got a little quiet.
The second game she broke again and went on a nice little run. But she missed a tough angle shot and I ran the table. So the third game she was racking and I said that I would lend her the 1500 and let her out of the bet if she wanted.
She just said break. I did, ran the table and won easily. She didn’t say anything just packed up her stick. Finally she walked over to me and said so to your place then?
We got back to my loft and she complimented me on it and walked around a little bit. Finally she just started taking off her clothes and said OK let’s get paid up. I give her another chance to back out but she just stripped naked showing Me her model type hard body.
She crawled up on my bed on all fours turned and looked at me and said come on let’s settle up. I strip naked in my penis which was long and thick and full of blood. Protruding noticeably from my flat belly. She looked at me and at it and said oh shit. She said OK I am 100% going to do this but please be gentle as I have literally never done it before. I Again said that we can worked it out another way but she just put her head down on a pillow and raised her ass into the air.
Perfect little round ass. I grabbed some lube from my nightstand and ran it up and down the shaft of my veiny hard cock. I rub some lube over the perfect little asshole and slid a finger and slightly which made her jump. I kept asking if she was OK and she’ll just shake her head yes. Finally I placed the hard head of my dick on her little brown star and began to push. She Screamed screamed but told me not to stop. She was so tight I did not believe it would work. finally I could feel my lubed head pushing in and whether she meant to or not she backed into me slightly which forced my penis deep inside of her ass. She screamed and fell forward I followed straddling her legs and staying inside of her.
I asked again if she was OK or wanted to stop she just shook her head and reach back and grab my hip. I just sat there deep side of her for several seconds and let her adjust and then I slowly began to move in and out. She just moaned And I slow fucked her for some time. It was so incredibly sexy and when she started to push back into me when I stroked her I felt my balls tighten And with a loud scream I release the biggest and most intense orgasm of my life deep in her bowels.
She moaned in relief when I finally sat back And pulled my manhood out of her. We will lay In each other’s arms for several minutes. She finally chuckled and said I hope we’re square. I said that we were. I then ask her. Was this just a bet that you had to pay? She said I would not have made this bet with anyone else and I am embarrassed about losing one but I have to admit I had hoped we would get here someday. I just never dreamed it would be with you starting in my ass. We laughed and then the dozed off of each other’s arms.
After a while we got dressed and went out and got food. I felt pretty horrible because she could not sit down so we still have a counter and ate. I insisted on giving her the rent money which she took with the agreement that we were going to continue to see each other.
We have and we have had sex many more times and she is talking about moving in with me which I love the idea. We have not done anal again although she says she wants to at some point but had still not recovered.
We also played a lot of pool together and she gets a little frustrated when she sees how good I can play. But she seems happy with the end result and so am I.
But I got lucky and ran into her at a local pool hall. She was by herself I’m just practicing. We started talking and shooting around and she continued to tease me and rub up against me. We weren’t really playing seriously and at some point she said she was tanking because she was hoping to get somebody to play and beat them for her rent money for this month because she short. I asked her how much she needed and she said 1500.
I felt a stir. Maybe this was the way to see how far the flirting would go. I told her I would play her best two out of three. If she won I would give her the 1500. She laughed laughed and said that was easy money for her because she had seen me play so much. She said I was basically just giving her the 1500 which didn’t seem fair. I told her I Was a little better than she thought. She said, well OK, obviously I don’t have the money so what do you want if you win.
Sex I said. If I win we go right to my house now and have sex. She again laughed and said you’re betting you could beat me to the tune of $1500 just to have sex with me? I have thought you were cute and tried to hit on you. I likely would have done it for free just because I think you are cute.
I said thank you I said OK then let’s make a little more interesting? She just looked at me. You win two out of three and I pay your rent I win two out of three and we go home and have anal sex. How is that deal?
She said well, I have never done anal sex and have no intention of what you’re not gonna beat me anyways so rock ‘n’ roll. We shook hands. And I racked the ball and let her break first game. She played a bit sloppy but good enough that I let her win. She laughed and said I could not believe this bet. I said well the stakes are higher for you, right? She was not dumb and gave me a look like she thought something might be up I got a little quiet.
The second game she broke again and went on a nice little run. But she missed a tough angle shot and I ran the table. So the third game she was racking and I said that I would lend her the 1500 and let her out of the bet if she wanted.
She just said break. I did, ran the table and won easily. She didn’t say anything just packed up her stick. Finally she walked over to me and said so to your place then?
We got back to my loft and she complimented me on it and walked around a little bit. Finally she just started taking off her clothes and said OK let’s get paid up. I give her another chance to back out but she just stripped naked showing Me her model type hard body.
She crawled up on my bed on all fours turned and looked at me and said come on let’s settle up. I strip naked in my penis which was long and thick and full of blood. Protruding noticeably from my flat belly. She looked at me and at it and said oh shit. She said OK I am 100% going to do this but please be gentle as I have literally never done it before. I Again said that we can worked it out another way but she just put her head down on a pillow and raised her ass into the air.
Perfect little round ass. I grabbed some lube from my nightstand and ran it up and down the shaft of my veiny hard cock. I rub some lube over the perfect little asshole and slid a finger and slightly which made her jump. I kept asking if she was OK and she’ll just shake her head yes. Finally I placed the hard head of my dick on her little brown star and began to push. She Screamed screamed but told me not to stop. She was so tight I did not believe it would work. finally I could feel my lubed head pushing in and whether she meant to or not she backed into me slightly which forced my penis deep inside of her ass. She screamed and fell forward I followed straddling her legs and staying inside of her.
I asked again if she was OK or wanted to stop she just shook her head and reach back and grab my hip. I just sat there deep side of her for several seconds and let her adjust and then I slowly began to move in and out. She just moaned And I slow fucked her for some time. It was so incredibly sexy and when she started to push back into me when I stroked her I felt my balls tighten And with a loud scream I release the biggest and most intense orgasm of my life deep in her bowels.
She moaned in relief when I finally sat back And pulled my manhood out of her. We will lay In each other’s arms for several minutes. She finally chuckled and said I hope we’re square. I said that we were. I then ask her. Was this just a bet that you had to pay? She said I would not have made this bet with anyone else and I am embarrassed about losing one but I have to admit I had hoped we would get here someday. I just never dreamed it would be with you starting in my ass. We laughed and then the dozed off of each other’s arms.
After a while we got dressed and went out and got food. I felt pretty horrible because she could not sit down so we still have a counter and ate. I insisted on giving her the rent money which she took with the agreement that we were going to continue to see each other.
We have and we have had sex many more times and she is talking about moving in with me which I love the idea. We have not done anal again although she says she wants to at some point but had still not recovered.
We also played a lot of pool together and she gets a little frustrated when she sees how good I can play. But she seems happy with the end result and so am I.
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