Long time lurker and lover of this subreddit so I thought I would give a this story a shot. If you all do like this story I have plenty more with Kelly and would love to share.
This took place during the last semester of my Junior year of High School. At the time I was 5'10, 225, and a decently fit guy. I had played football all throughout my high school career and spent most of my time in the weight room. I was an offensive lineman so being a big bigger was always a must but at the time I was built more like a fullback (for those of you who know anything about football). Her name was Kelly, she was 5'5, ridiculously fit girl (she had been a dancer all her life) with a beautiful ass and amazing C cup tits. We had dated the year before (I have plenty of stories from that time if there is interest) but after we broke up we would constantly hook up when we were both single. She had always aimed to please me and loved to try new things in the bedroom. Our M.O. was to sneak out of our parents houses, I would go pick her up, take her back to my house and then fuck like rabbits. We had played strip poker a week before with one of my best friends and talked about doing it again. I received a text about 11:00 pm. "Hey! :) want to hang out tonight?" Obviously I knew what that meant but I didn't want to seem to eager so I texted back "Sure, what do you want to do?" and she responded with "Well I want to work on my poker skills ;)" We waited for our parents to fall asleep and we snuck out of our houses, I picked her up and we came back to my house.
In my room we started to play 5 card draw on the end of my bed in the dim "mood" lighting I had in my room. The light just consisted of a lava lamp, cheap x-mas lights, and a dim lamp. I can't remember the exact hands that were played (this was 8 years ago) but I do remember the progression of us getting naked. Kelly was either getting ridiculously lucky hands or she had hustled me because before I knew it I was only in boxers and she was in a bra but still had all her pants on. Through the hands of god I got her down into just her thong and then in the remaining two hands (for all I know she let me win a couple) we were both naked. I asked her if she wanted to keep playing and she said "yeah, but what can we play for?" Me being the horny teenage boy I was responded with "sexual favors" She said she was in and we continued playing.
We knew what each other liked and mutually knew we did not want this to end quickly. She one the first hand and made me make out with her and start to finger her. I laid down my cards and leaned over and began to kiss her. There were always sparks between us when we kissed and this time was no different. We fell to the bed and passionately made out. I slowly slide my hand down to her already wet pussy and traced her slit. I pushed one finger into her and she let out a soft moan into my mouth. I then slipped another two fingers, three total into her and began to speed up my pace. She pulled away from my kiss, buried her head into my shoulder and moaned for me to keep going. This lasted five minutes before I stopped and said we should play another hand. I won the next hand and asked for a blowjob. She stared into my eyes, leaned forwards, grabbed by hard 7 inch cock and asked "Do you want me to make you cum?" I gasped a bit and shook my head no and she pushed me to the bed. She licked the bottom of my shaft from base to tip, cupped my balls and truly made it look like she was enjoying the best lollipop of her life. She was an expert at giving head. It look everything in my power not to cum. After about another five minutes she stopped and said lets play another hand.
She won and said she wanted my help in deciding what to do next. After talking about it she wanted me to face fuck her. I had never done anything like that at this point in my life and in all honestly I wasn't mature enough to completely understand how hot it could be to have a girl be so submissive. She laid back and I straddled her chest and leaned forward. She took my length in her mouth and I began slowly thrusting. I was so young and afraid to make her gag so I stopped after a minute and said we should play another hand (stupid I know but I was terrified).
I won the next hand and knew this would be my opportunity to do something more than just the normal mind blowing sex we had. I looked at her and said "We could try anal?" she had a slight smirk and said "I think you really want to try that, so lets do it!" she laid down on her stomach while I rolled a condom onto my cock and then straddled her from behind. I spread her cheeks and pressed the head of my cock against her asshole. "You have to go slow!" she told me with her face in the pillows. I pushed slightly against her tight hole and she squeaked a bit and I paused, letting her adjust while I took in the scene. This beautiful girl laying below me, her hand spreading her gorgeous ass and my cock resting with its head in her asshole. After about a minute she told me to keep going. Inch by inch she took about half of my cock and asked me to pause. I slowly began rocking my hips in and out of her not going past the 4 inches she had already taken. It felt amazing. Tight just like her pussy and the warmth. Oh god the warmth, this more than I deserved as a dumb high school boy. As her sounds of displeasure turned into means of pleasure I pressed my luck and kept going deeper. Soon I was balls deep in her ass and began to speed up. I began to moan with every thrust, and she would answer my moans with her on. She looked back and me and said "Does that feel good baby? Do you like my ass?" and it took everything I had not to fill the condom right then and there. I could only answer with a grunt. I took over spreading her ass cheeks and began just pounding away. I told her I was close and she just told me "Cum for me, cum in my ass" and I lost it. I could feel my thick threads of cum full the condom.
After I finished cumming I slowly pulled out and pulled the condom off, threw it away, and laid next to her. We made out more and I fingered her lightly. Eventually we knew our parents would be waking up so we got up and I drove her home.
Kelly was one of the best sexual partners I have ever had, even 7 years later. I titty fucked her, fucked in all positions, fucked in a car, and a lot of other things. She used to send dirty pictures all the time which I have since deleted (I know I hate myself too). If there is any interest I have more stories about her as well as the other girls I have been with. Thanks for reading!
Source: reddit.com/r/gonewildstories/comments/301kaj/first_time_and_only_anal_with_kelly_mf_long
keep going with your stories…