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Summer with my best friends sister - Part 1
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Back when I was 18 I was spending the night at my friend's house one summer night. It was the middle of the night and he had passed out in his room but I was still up.

I had gotten up to use the bathroom and I heard their front door open and close on my way back to the room. I ran into his 22 yr old sister in the hallway. I had always had a crush on her. She was petite but curvy and we had some flirting encounters in the past.

She took one look at me, grabbed my hand and pulled me behind her to her room. She shoves me inside and closes and locks the door. She flipped some low lights on and I could see her face clearly and it looked like she had been crying. I also saw she was wearing a very sexy black dress which she was in the process of removing. I stared in shock as she stripped down in front of my eyes until she was just wearing a black pair of crotchless panties. Her tits were even better than I could have imagined and her pussy was neatly trimmed. She saw me looking at told me to lay down on the bed. Which I did immediately.

She crawls up onto the bed down by feet and worked her way up to my waist. She told me to lift my ass and she yanked my shorts and boxers down springing my hard cock free. She barely had me undressed before she inhaled my cock and started going at it like crazy. I moaned and twitched and she looked at me and told me that her boyfriend had dumped her tonight and that I had better not cum until she was done. She moved up until we were face to face, grabbed my cock and guided herself onto me. She leaned up and started riding me hard. She took my hands and put them on her tits as she just kept grinding her self into me.

I was basically in shock for the first part of all of this which is probably why I didn't cum immediately inside her. She felt absolutely amazing. She climbed off and moved to the foot of the bed on her hands and knees and told me to get back inside of her. She told me to try and pull out before I came but she was on the pill so it was ok if I couldn't. I got behind her and slipped back in and started thrusting as best as my inexperienced ass could do. She kept her ass up so I was basically thrusting down into her and she really enjoyed that. I could feel her rubbing between her legs and started making louder noises. We didn't do this for very long until she grabbed a pillow and shoved her face in it as she came. Her orgasm set me off and I didn't even think to pull out, in fact I pushed in deeper and dropped what felt like the largest load of my life into her.

After we finished she told me she was going to take a shower and left me there. I got dressed and went back to my friends room and fell asleep. The next morning when my friend had gone out for a run (he was a gym bro even back then) I was sitting in their living room and his sister came out. She came over and sat down next to me before thanking me for the previous night. We talked about how her boyfriend dumped her when she was expecting them to sleep together for the first time and she came home very frustrated. I made a joke about it happening again and she got quiet and asked if I wanted to.

Best summer ever and more stories to come.

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1 month ago