The following is a true account of what happened to me and my girlfriend, now my wife, when we started dating in high school. At the time I had no idea what a cuckold was.
Jenny and I started dating in our senior year of high school and I knew right away this was the girl I wanted to spend my life with. She was my first real girlfriend and I could not wait to get in her pants. I was a shy guy, and remained a virgin till the age of 19. Jenny had 4 previous boyfriends but she too remained a virgin because she always knew she wanted to give it to someone she loved and cared about. I knew from that the only sexual acts she had ever done with her other boyfriends was she had let them perform oral on her and she had given a them blowjobs as well. I was pretty good friends with all her ex boys and I knew in detail what they had done together. Part of me was bothered by her past, but another part of me was turned on in a jealous type of way.
Her last ex boyfriend, Jay, was one of my best friends and he and Jenny use to fool around all the time. Jay was always telling me how she would suck his cock everyday after school and he would cum all over her tits and face. He was always saying how he was going to take her cherry and add another notch on his belt. During high school it was Jays mission to fuck as many virgins as possible. By last count before Jenny he was at 19. He always told me Jenny was going to be his toughest to crack because she considered it special. Jay was always bragging about how big his dick was and how his balls were always full of cum. One weekend Jay cheated on Jenny with some other girl and fucked her 2 times at a party. Jenny got wind of this and dumped him Monday morning. I was happy because Jenny deserved better than Jay.
About a month later Jenny and I started to date and we were a match made in heaven. We did everything together and she even started giving me blow jobs every once and a while.
One weekend we were at my place and a Jay and his latest squeeze, and 1 other couple were there. We were just hanging around drinking and having fun.
We all got pretty drunk and Jay, Jenny and I were the only ones left awake not passed out. Jenny and I were on the couch making out right next to Jay who was telling us to get a room. Jenny still had anger towards him and I guess she wanted to make him jealous. She got a blanket and put it over top my waist and went under it to give me a blow job. Jay was sitting right beside me listening to the sounds. Jay was getting a little annoyed with us and told me that Jenny should at least give him a handjob or something. Drunk and stupid I told Jenny he was right and before I knew it he had his hard cock out ready to go. Jenny just looked into my eyes and I told her it was OK. Jay did have a big cock, I was a little surprised at the size of it and thought no wonder he has no problem getting all these girls. Ive measured mine at 5.5 inches and if I had to guess he was between 8 and 9 inches.
So Jenny is now sucking my cock and stroking Jays. I eventually came in her mouth and kinda pass out. I can still here them and Jay is asking for a blow job so he can cum. Jenny hesitates but he lifts her up and starts kissing her. I was too drunk to say or do anything, but I know im a bit upset about this. The last thing I remember was Jenny on top of him naked and kissing Jay.
When I woke up the next day they were both gone. I called Jenny as the memories of last night are all coming back to me now.
I found Jenny at home and asked her what happened. She had a strange look on her face and I knew instantly that Jenny and Jay had sex.
I went to see Jay later that day to find out what happened. Jay said he was sorry and that he didnt know she was still a virgin. He told me they ended up on the floor and his started to slide his cock in her, he got about 2 inches in and she asked him to stop cause it hurt. He took it out and a few minutes later tried to slide it in again. This time she didnt tell him to stop and he just kept going. He realized she was a virgin and took it slow. Jay said they fucked for only 5 or 6 minutes before he pulled out and cummed on her stomach.
Jenny was upset and aplogized to me, I love her too much to let her go. I told her it was Ok, and I could live with the fact another guy got her virginity. Deep down I was devastated she didnt save it for me. Jay and I are still friends and not a day goes by where I don't think about that night, and it turns me on and makes me horny knowing my sweet girl lost it to such a player.
Jenny and I talked about it and she said he was really gentle and knew exactly what he was doing. She can see why so many other girls gave their cherrys to him.
FUCK MY WIFE!
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