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Girlfriend's Sexual Past - My girlfriend and I started dating at the end of high school, both 18 years old at the time. We knew of each other as she had dated many of my friends and people I knew. I would often see her at parties, and we would always chat a little but it always seemed like she was with another guy. She began dating my best friend John and I got to know her even more as they dated for about 6 months. John would often tell me about the things they were doing and he described how he finally got to pop her cherry one night. She had hesitated on having sex but John was a real womanizer and one night the two of them were drunk and he managed to work his cock into her.



He told me how her pussy was extremely tight and he could only get it about halfway in for a few thrusts before she asked him to stop cause it hurt too much. I knew from seeing John in gym that he was very well hung. He and Samantha hooked up again that same weekend and this time he finished the job and really gave it to her. Within a week he had let her go and moved on to another girl, leaving her feeling used and bad. Almost every night I would lie in bed thinking of the two of them together and wish it was me having all this sex, as I was still a virgin to this point.



Samantha and I became better friends and we would hang out all the time, but she told me she wanted a break from boys as she was still burned from what John did to her. Every night I would jerk off thinking about how great it would be to fuck this girl. Finally after about 2 months we started making steady and we officially became a couple. However all we ever did was kiss as her friends had warned her to take things slow with me and not to trust any more guys. It took about 6 months before she finally gave me a blowjob, and she was the first girl to ever see my cock. The first time she took it out she warned me that she has been told she is not very good at sucking cock so if she was doing a bad job and wanted her to stop just let her know. Not having anything to compare it to I told her it was great and she replied by saying that my cock was nice to suck cause it was not too big. I know she didn't mean anything by it, but my ego took a big hit. Over the next few months we did everything together and while we never had sex she did give me blowjobs all the time and I would often go down on her and lick her to orgasm. I have to admit every time I went down on her all I could picture was John sticking his cock in her and how he had gotten her most precious possession and I am still yet to get my own cock in her and it has almost been a year of dating now.



Finally Samantha and I had the talk and we discussed sex. She asked me if I was still a virgin and I told her that yes I was. I asked her and she got a little pissed at me and said I already knew the answer. She still hated John for what he did to her and she hated that he was my best friend. She did agree that we could start having sex but I would have to wear a condom. She told me John didn't wear one and although he didn't cum in her she was terrified she might get pregnant. Reluctantly I agreed and the first time we did it was amazing. Although I could not feel too much, I came pretty quickly. We were now having sex on a regular basis but I found that the only way I could get really hard or turned on was if I would imagine her with John or some of the other guys I know she dated. I was extremely jealous but turned on at the same time and I didn't know how to express or describe these feelings. Eventually I discovered what a cuckold was and I am pretty sure I fall into that category and wanted to be one. During the last 3 months I have started asking her about her past in more detail and while at first she was very reluctant to open up she has now told me everything, and I have reassured her I am fine with it and it actually turns me on.



I have asked her how many boys has she kissed, and she honestly has no clue but it's well over 30. Every guy she made out with since she was young has either grabbed her tits or ass as well.



How many cocks has she seen, she has seen about 13 or so. When she was younger guys would ask if they could jerk off while she watched and she always said yes.



How many has she actually sucked? Samantha told me she has sucked 10 of the guys. When I asked her who they were she didn't want to tell me as she said I knew them all. This turned me on even more as I had not a clue her past was this promiscuous. Eventually she rhymed them off to me, Adam, Kevin, Jayson, Mike, Tanner, Theo, Billy, Jamie, Nick, and of course John. WOW I thought, I know all of these guys and they've all had their cocks in my girlfriends mouth. I thought I was going to blow my load right there, but I needed to know more. I asked her who had the biggest. She told me John was probably the biggest, and he also had very big balls. She was never crazy about sucking him because he was not circumcised and her jaw always hurt, plus he told her that she basically sucked at doing it.



Who was her first? Adam and she will always remember his cock because it was really hot and curved like a banana. He also was the first guy to cum on her face. Kevin was her 2nd and he had a thick cock and he would cum very quickly. Mike was a skater she made out with at a party and she gave him a blowjob drunk. Theo and Billy were also drunken party blowjobs. Jamie she dated for af few weeks and he was the 2nd smallest after me, as I guess I am the smallest guy from what she has told me. Nick was a stud, he was a Greek guy and his cock too was uncut and almost as big as John's tool.



She sucked him off only 3 times. I told her how turned on I was by hearing this and she said she was too. She told me she sometimes thinks of them and she gets really wet doing so.



She could tell I was horny and she got more comfortable talking about it over time. I asked her about the first time she fucked John, and she was a bit reluctant at first, but I assured her I really wanted to know. I kind of already knew but wanted to see if their storys matched. The way she describes it is she was on top of him naked and they were making out. Samantha kept rubbing her pussy on his cock teasing him and before she knew it she felt it start to go in a little. She was as horny as she had ever been but the pain was hard to take, but he managed to slide it in as much as she could. She slid up and down about 5 times, before she got off him and finished him off with a handjob. John had always told me that he fucked her, but from the sounds of it, she fucked him.



The second time that weekend he called her over and he finished the job and fucked her for 2 times.



Knowing he has fucked her twice bareback and I am still yet to experience that is all I can think of. I have asked her if she wants to fuck him again, and she has said not really as she dislikes him too much. She has always hated him since, and even more so because she gives good head and he wasn't happy with her.



The last little while all I could think of is John fucking her again slamming his cock into her. Last week I went for beers with John and Adam and all I could think about was the two of them tag teaming Sam in front of me. It was kind of awkward being with them knowing all I know about what they did with her. They have dropped hints about her and im sure they have talked behind my back about it.



The two of them are coming over tonight to watch the game, and I told Sam to be here. This morning before she left for work I told her that 2 of her ex boyfriends are coming over as I licked her sweet pussy, and she seemed to get even more wet. We will see what happens tonight.



danygraft @ yahoo.ca



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