trying for a one night stand ended up with my first time with anal (m/f)

I was in my early twenties and my girlfriends and I were going out to the local bar on a friday night for what was the most packed happy hour in the county. 2 for 1s, a waterfront location and a “meat market” atmosphere. I told my girls that I wanted to have a real one night stand. Not that I hadn't tried to have one before, but they always came back for more. This time I meant it. We arrived at mid swing into happy hour and definitely were noticed. when you have 4 girls who are all tall fit and blonde even in the tropical area we live in people notice. I was wearing tight fitting jeans showing off my plump round tight ass, a white tank top that showed my small b cup breasts, my hair was short blonde and pixie cut. As we stood on the the dock and looked around I saw him, he was with a couple of his friends and immediately noticed me looking at him, and he saw the fire in my eyes. He wasn't my normal type, he stood only about 5’7” and at 5’9” i was a good two inches taller than him in my bare feet. but with my wedges on i was about 6” above him. he didn't seem to care in the slightest. but even though he was short and cuban ( Im into white boys, no discrimination, they are just my flavor) he was thick built and Iiked that, but more importantly he had braces. He was not a boy he was a man, a full grown man with braces, and I have a fetish for three things: thick guys (or chub), mouth wear and beards. It was an instant turn on. my paints were immediately wet. they came over flirted talked and did their typical male mating ritual, figuring out who was going home with who. As it got later my gf Kyla suggested we all go back to her place to go in her hot tub. Now at this point I was pretty drunk but I decided to ride with the Cuban in his truck to show her the way. as we walked to the truck and he let me in he kissed me, i felt his full lips and metal agains my full lips and knew i wanted more. we flirted and teased each other all the way back to her house. once we got there we turned into a party of 6, my one friend left and he had three, we made our selves cocktails and proceeded to the back yard. where Kyla informed the guys of the rules, no suits allowed. all three of us proceeded to take our clothes off pretty quickly and pranced giving them a show. I made sure as i climbed in to bend over and test the waters, giving all 3 of them a picture perfect shot of my perfect apple bottom ass, and just a peak of my pussy. they proceeded to strip making jokes about it being cold out, climbing in and joining us. Things started to get a little frisky as we started playing and adult version of spin the bottle after we had been in the hot tub for a while. I was kissing my friend Kayla, Kayla was kissing Lee, Lee was kissing guy 2, Kayla was sucking guy 3’s cock. then the cuban dared me to kiss Lee and me and Lee had to inform them that we were cousins, so sorry no boys. But as a consolation prize I went under water and wrapped my lips around the cubans cock, i managed to do this for about 30 seconds then needed air. After i came up I made and excuse about starting to turn into a prune and needing to towel off and get another drink. C said he would come with me. we went inside and immediately he dropped to his knees right in the middle of the living room, throwing my leg over his shoulder and burying his face in my pussy. He licked and sucked my cunt like a pro, nibbling on the clot and sliding his tongue up and down my lips while i wriggled and ground on his face. it wasn't long before i was ready to cum and I made him stop I wanted to enjoy this i wanted to go further. once i made him stop i said was getting cold and he suggested that we go take a shower to warm up so we went to Kylas bathroom and he realized she had a roman tub, so he suggested we make our own little hot tub. we stepped in and turned on the bath water. we made out and kissed, i grabbed the soap and started to stroke his cock, up and down turning and twisting and making him wriggle beneath me, I could feel his body taking pace and getting closer. then he stopped, he picked me up and flipped me over the side of the tub pulling my ass into the air and once again burying his face in my pussy. he once again played with my clot and hole with expertise and then he started to lick my asshole. I had never had this done before, at first i flinched but he just pulled my as further to his face and buried it in me. licked and tongue fucking my asshole. before i new it he was slipping a finger in my asshole and slowly, with clear precision fucking it. I was his toy. This was pleasure that was new to my wild ways and as he continued to finger fuck my ass he asked me could fuck me in the ass. I said I never had, only had played just the tip once and that it hurt too much. he said that if it was done right it wouldn't hurt and He promised it wouldn’t and as he continued to finger fuck me I agree he continued his prep of my virgin hole by proceeding to fill my ass with two fingers. As i started to meet his fingers and moved more and more with him he rose up and brought his hips to my ass, spread my cheeks and slowly slide the tip of his thick cuban cock in my little tiny fuck hole. I gasped, but i moaned it felt so good. he started out slowly, but quickened his pace, this he was fully fucking my in my back door. After our pace and rhythm had loosed up my body he sat down in the tub and pulled me down onto his dick so that i was riding him with back to his chest, he spread my legs out and over his thighs and began stroking my pussy while i moved on his cock. As i got closer , he moved his and down and slide 3 fingers into my pussy sending me over the edge with double penetration and as i bucked and clamped down on his cock and his fingers he finished with me and came in my ass hole. 

4 comments

1. Let me help make that readable: I was in my early twenties and my girlfriends and I were going out to the local bar on a friday night for what was the most packed happy hour in the county. 2 for 1s, a waterfront location and a “meat market” atmosphere. I told my girls that I wanted to have a real one night stand. Not that I hadn’t tried to have one before, but they always came back for more. This time I meant it. We arrived at mid swing into happy hour and definitely were noticed. when you have 4 girls who are all tall fit and blonde even in the tropical area we live in people notice. I was wearing tight fitting jeans showing off my plump round tight ass, a white tank top that showed my small b cup breasts, my hair was short blonde and pixie cut. As we stood on the the dock and looked around I saw him, he was with a couple of his friends and immediately noticed me looking at him, and he saw the fire in my eyes. He wasn’t my normal type, he stood only about 5’7” and at 5’9” i was a good two inches taller than him in my bare feet. but with my wedges on i was about 6” above him. he didn’t seem to care in the slightest. but even though he was short and cuban (I’m into white boys, no discrimination, they are just my flavor) he was thick built and liked that, but more importantly he had braces. He was not a boy he was a man, a full grown man with braces, and I have a fetish for three things: thick guys (or chub), mouth wear and beards. It was an instant turn on. my pants were immediately wet. they came over flirted talked and did their typical male mating ritual, figuring out who was going home with who. As it got later my gf Kyla suggested we all go back to her place to go in her hot tub. Now at this point I was pretty drunk but I decided to ride with the Cuban in his truck to show her the way. as we walked to the truck and he let me in he kissed me, i felt his full lips and metal agains my full lips and knew i wanted more. we flirted and teased each other all the way back to her house. once we got there we turned into a party of 6, my one friend left and he had three, we made our selves cocktails and proceeded to the back yard. where Kyla informed the guys of the rules, no suits allowed. All three of us proceeded to take our clothes off pretty quickly and pranced giving them a show. I made sure as i climbed in to bend over and test the waters, giving all 3 of them a picture perfect shot of my perfect apple bottom ass, and just a peak of my pussy. they proceeded to strip making jokes about it being cold out, climbing in and joining us. Things started to get a little frisky as we started playing and adult version of spin the bottle after we had been in the hot tub for a while. I was kissing my friend Kayla, Kayla was kissing Lee, Lee was kissing guy 2, Kayla was sucking guy 3’s cock. then the cuban dared me to kiss Lee and me and Lee had to inform them that we were cousins, so sorry no boys. But as a consolation prize I went under water and wrapped my lips around the cubans cock, i managed to do this for about 30 seconds then needed air. After i came up I made and excuse about starting to turn into a prune and needing to towel off and get another drink. C said he would come with me. we went inside and immediately he dropped to his knees right in the middle of the living room, throwing my leg over his shoulder and burying his face in my pussy. He licked and sucked my cunt like a pro, nibbling on the clit and sliding his tongue up and down my lips while i wriggled and ground on his face. it wasn’t long before i was ready to cum and I made him stop I wanted to enjoy this i wanted to go further. Once i made him stop i said was getting cold and he suggested that we go take a shower to warm up so we went to Kylas bathroom and he realized she had a roman tub, so he suggested we make our own little hot tub. we stepped in and turned on the bath water. We made out and kissed, i grabbed the soap and started to stroke his cock, up and down turning and twisting and making him wriggle beneath me, I could feel his body taking pace and getting closer. then he stopped, he picked me up and flipped me over the side of the tub pulling my ass into the air and once again burying his face in my pussy. he once again played with my clit and hole with expertise and then he started to lick my asshole. I had never had this done before, at first i flinched but he just pulled my as further to his face and buried it in me. licked and tongue fucking my asshole. before i new it he was slipping a finger in my asshole and slowly, with clear precision fucking it. I was his toy. This was pleasure that was new to my wild ways and as he continued to finger fuck my ass he asked me could fuck me in the ass. I said I never had, only had played just the tip once and that it hurt too much. he said that if it was done right it wouldn’t hurt and he promised it wouldn’t and as he continued to finger fuck me I agree. He continued his prep of my virgin hole by proceeding to fill my ass with two fingers. As i started to meet his fingers and moved more and more with him he rose up and brought his hips to my ass, spread my cheeks and slowly slide the tip of his thick cuban cock in my little tiny fuck hole. I gasped, but i moaned it felt so good. he started out slowly, but quickened his pace, this he was fully fucking my in my back door. After our pace and rhythm had loosed up my body he sat down in the tub and pulled me down onto his dick so that i was riding him with back to his chest, he spread my legs out and over his thighs and began stroking my pussy while i moved on his cock. As i got closer , he moved his and down and slide 3 fingers into my pussy sending me over the edge with double penetration and as i bucked and clamped down on his cock and his fingers he finished with me and came in my ass hole. I was spent and spaghetti after that, we showered and cleaned up and got dressed. when he was leaving he tried to tell me his name ( again, I didn’t pay attention the first time). I told him shhhhh, I don’t want to know, I want this to be a one time thing…..

2. Thick guy and I have a beard. No braces but 2/3 ain’t bad!

3. thanks for the help, I think I’ve cleaned it up a little better thanks to you :)

4. yea 3/3 would be a unicorn….

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