Story Details

My Sisters Best Friend

rjr016 on Anal Stories

I've always been good friends with my sister's friends.  I've even gotten lucky with a few of them. But none of them really were ever any good in that they were usually inexperienced, but on this night inexperienced was a good thing.

My name is Chase and I was 19 at the time. I came home from hanging out with the guys at about midnight one night, and headed upstairs to my room.  To get to my room, I have to walk through the gameroom and past my sister's room.  This night, my sister had her friend over, whom I knew, but had not had a real conversation with in probably three years. OMG, did she look good tonight tho.  Her name was Kristin and she was now 16, but she could've been 21.  They were watching a movie and my sister had already fallen asleep.  I made a casual joke about her being asleep and sat down on the couch to wake her up.  Kristin was sitting in the lazyboy on the other side of Kate, my sister.  Kate sat up and talked for a while and fell back asleep after I started watching the movie.  Kristin and I didn't say much to each other until the movie was over.  When it was over and I turned it to the sports channel, Kristin lost interest and turned to me.  "How come we never talk anymore?"

"I dunno" I said "I guess we really don't hang out, you know . . . "

She agreed and said well maybe we should catch up sometime. I said "Well how bout we put her to bed and catch up" pointing at Kate.  I honestly had no ill intentions at this point, but as I would come to find out, Kristin did.

I tucked Kate in and shut her door and told mallory to come to my room, I was gonna check my myspace or facebook, whichever one I was using back then.  I laid down on my bed and she sat against the far wall.  We had a pretty cool conversation for two people that really never talked.  Every now and then I would laugh at something I saw on the computer and turn my laptop to show Kristin.  Then we would go back to talking and laughing.  After a while she asked if she could check her myspace and of course I didn't mind. So she crawled over to the side of my bed to get the laptop. Oops. Alot of guys know that when you can see down a girl's shirt it's really hard to look away.  Kristin was wearing a white cami and crawling over to me revealed it all.  Suddenly I had ill intentions. Her boobs were bigger than I had previously thought, and I now noticed that she had on no bra.  She knealed at the side of my bed and started updating her myspace.  We kept talking but suddenly I felt what she had been hinting at the whole time.  I felt myself staring into her eyes longer and smiling at anything she said or pointed out on the computer. She felt the same and suddenly it began awkward. She went back to the laptop and my mind raced about what I could say next, but then she broke the ice.

"This is hurting my back, scoot over a little bit."

"Score!" I thought as I made room for her to scoot in beside my on top of the covers. As she laid down on her stomach and facing the laptop I couldn't help notice how short the cotton shorts she was wearing were. I could make out the bottom of her but cheeks. I had a full hard on now and I think she noticed when I tried to adjust slightly.  I could feel her smooth tan legs on mine and everytime we laughed I could feel her snuggle up closer to me. Then it just felt right, we both turned and gave each other a little peck. She stopped and smiled at me and then shut the laptop.

She turned off my lamp and pushed me over on my back.  She pulled her leg up and threw it over my waist putting her crotch on my hip. We made out in this position for what seemed like hours but I enjoyed every second of it.  In mid-kiss she slid her leg back down and bumped my hard on. She suddenly stopped and said sorry. "What?" I said. She asked if it hurt and I said no. "Oh she said" and brought her leg back up across my cock. "That doesn't hurt?" she asked. "No, it actually feels kinda good."    "Oh" she said again. We went back to kissing and every now and then she would press her soft leg onto my hard-on sending tingles through my body. After a few more minutes I grabbed her hand and slowly moved it to my boxers. She put her hand on my cock and started massaging it. "Oh yeah, that feels good" I said. We went back to making out and I began playing with her breasts through her cami.  I then slowly moved my hand up her shirt and onto her right boob. I could feel her body get chills. She was obviously new to this, but I could tell she wanted more. I massaged her breasts more firmly as she was moving from my cock to my balls with her hand. I then removed my hand and pulled her cami up and off revealing her beautiful c cups with perfect pink nipples.  I put my head into her chest and began kissing all over her breasts and nipples. She grabbed the wasteband of my boxers and pulled them down. My cock sprung out and she was stunned for a few seconds having not seen a penis up close before. She grabbed hold and naturally began stroking my cock as I continued to french her beautiful breasts. I then moved my hand down to her crotch and rubbed her pussy through her shorts. She came quickly, before I even had a chance to get her shorts off.

"Oh my gosh, that feel good. I've never had anyone else do it for me."

She wouldn't let me touch her there for a few minutes. I understood.  She then asked if she could suck my cock. I told her, you probably don't have to ever ask a guy that question, you can probably just go for it.  She moved down and began kissing my cock. Damn, I was in heaven, and Damn was she hot. She then ran her lips up and down my shaft almost causing me to shoot, and then when she moved her hand up and stroked my now wet cock I couldn't hold it anymore and blew my first load of the night. She then to my surprise leaned down and licked up all of my come.  I love that taste she said gimme somemore. I can't i replied, that's all i had. "You'll just have to work for it again."    "Okay" she said. I then pushed her back and grabbed her shorts and pannies and pulled them down to her ankles and off.  I crawled up beside her and laid down and resumed our kiss. I moved my hand down to her pussy and started rubbing her clit. She naturally began breathing harder and instinctively spread her legs.  "Oh my god, Chase that feels so good." She kissed me harder and I move my fingers down to her vagina. I slowly began working my middle finger into her and she pushed down onto my finger.  I could tell that she had never had anything larger than my finger in her.  I found her hymen and began pushing on it with my middle finger. It broke and she let out a small wimper as a trickle of blood covered my hand. "Wait" she said. I stopped with my finger past her hymen to let the pain subside. I kissed her and could tell when she was ready. I began moving my middle finger deeper inside her as she increased the passion in our kiss. I began stroking in and out as she breathed harder. I removed my middle finger and rubbed her clit her a few minutes as she kissed me harder and harder and spread her legs wider. She then pushed me back and leaned over towards me again throwing her leg over my waist.  I was still massaging her clit slowly as she moaned into my mouth.  I moved my hand lower and began pushing two fingers into her pussy still rubbing her clit with my thumb. She orgasmed again and halfway screamed in pleasure as her vagina was sucking my fingers into her.  This time she didnt stop. She kissed me harder and started to pull herself the rest of the way on top of me. We were kissing so hard it was difficult for me to breath but no way was I stopping.  She was now on top of me rubbing her clit on my hard-on.  I reached around behing her and grabbed the base of my cock and aimed it at her vagina.  I pushed up and felt the head of my cock at her opening. She began pushing back onto my cock never breaking our extreme kiss.  I slowly pushed up and slid the entire length of my cock into her. We held this position while kissing for probably 30 minutes so she could adjust to the feeling. I then slowly started pulling back and removed all but the head of my cock, and then plunged it firmly into her pussy. She orgasmed again almost causing me to flood her pussy, but I held back. She began to rock her hips plunging my cock deep into her vagina.  I began to push back as we still were kissing passionately. Our tongues tossed as I slow fucked the tightest pussy of my life. I then felt it coming and told her to get up quick. She knew what was happening and dove down and took it all and kept on sucking when my come subsided.  She kept me from getting soft and probably gave me an even bigger hardon. I rolled over and told her to get on her knees.  She did as she was told and I climbed around behind her and shoved my cock into her pussy. She moaned so loud I could have sworn someone would hear. She orgasmed again and collapsed on the bed. After what seemed like an hour of laying together naked she asked if we could try the other way. I asked what she meant and she replied. "You know what I mean . . . back here." as she pointed to her ass.

Damn, my mind raced. I had always wanted to but no girl had ever agreed to it. This girl was begging. Sure I said, as if I knew what it was like. She grabbed my cock and started stroking to get it hard again. She then placed those beautiful lips back on mine and resumed our perfect kiss once again.  I moved my hand around behind her and started circle her anus with my index finger. I slowly inserted finger into her anus and it clamped down preventing me from going any further. "Sorry, she said It's not slippery like my coochy"  "Well we can make it slippery" I said

"How"

"Lets go get in the shower."

Okay she said. So she climbed out of the bed and pulled me by the hand to the shower.  She turned on the water and climbed in pulling me along.  We again resumed our kiss standing up as she rubbed my still hard cock. I moved hand around behind her and starting probing her anus again but again was prevented from pushing my finger in by her natural reflex and dryness. She stopped to look at me and said well lets do this. She grabbed my hand and poured conditioner into my hand and leaning over slightly poured some down into her crack. Now try she said. I rubbed the conditioner all over my handed and her crack as turned her head to watch. I pushed my finger into her hole and it popped in quickly. Her knees buckled. "Oh my gosh, do that again." I finger fucked her first with one finger and inserted a second as she loosened up. She grabbed the conditioner and reached around behind her and began lubing up my cock as I stood behind her finger fucking her. She grabbed my hand out of her anus and pulled me by the cock with her other hand towards her anus. I pushed and slowly the slippery head of my cock disappeared into her butt. Again her knees buckled and I grabbed her hips to hold her up. She put her hands on the wall of the shower and I began pushing my length into her. In and out, I fucked her ass as she moaned for more. Harder she said. I reached around and finger fucked her pussy with my hand. She orgasmed twice before telling me to stop. She then turned around and kissed me passionately, stopping only to say. "Chase, I think I'm in love with you." I told her the same later that night. Kristin stayed the night three more times in the next 2 months until our secret was revealed to my sister somehow. I've not wanted to be with another girl since. We now live together 4 years later and are soul mates. We are to be married next year.

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