I knew she had 4 previous boyfriends before me and after assuring her it was ok to tell me what she had done with them she recently opened up and told me everything.
Her first boyfriend, Adam, taught her how to kiss, give head and he was the first to give her oral. He was a good kisser and he loved to lick pussy. She said he had a big bend in his cock that went downwards. She described his cock as being big and uncut, probably in the 7" range.She use to suck his cock almost everyday for about a month and he would always cum on her face or in her mouth. She was going to give her virginity to him but he was cheating on her with another girl so she ended it right away.
Her 2nd was a lifegurard at a local pool she use to hang out at. HE was 22 and she was just 15. She use to make out with him but nothing more than that. They both knew the relationship would not work because of the age difference so they ended it.
Her 3rd was a guy named Kris. The two of them use to dry hump eachother and she would give him blowjobs whenever they were together. He had a thick uncut cock, she described him as being really thick. He wanted to fuck her but she was saving herself for Mr.Right. She was also afraid to put something that thick inside her being a virgin.
Her 4th boyfriend was Jay, who was and still is my best friend. He was 18 and she was 16 by this time. She told me Jay was experienced at what he was doing and he had a reputation as being a player, but he was hot and treated her good. On their first date he had her sucking his cock and she remembers thinking that these things keep getting bigger and bigger. The way she tells me is that he was huge, like 8-9 inches, but his balls were also huge like two tennis balls hanging there. Ive seen his cock on many occasions and he is big. He too was uncut. She did more with Jay than anyone else, and she was reluctant to tell me, but she use to swallow his cum, he would lick and finger her ass and pussy, and he was always on top of her rubbing his cock on her pussy, something she never let any other guy do. One night the two of them were in her basement cause her parents were away for the weekend, and they had been drinking alot, he had been licking he pussy for what seemed like hours and she was hornier than she can ever remember. Jay eventually took a break and started to kiss her which got her even more turned on, and started pushing his cock into her. As ***** as she was all she remembers is pain and she told him he was too big. Jay told her he only got the head in her and it would be ok. He got back on top of her and again started pushing in. This time he got it halfway in and held it there for about 5 minutes while he kissed her some more. He started moving back and forth pushing more and more into her. She said the pain was too much to take and asked him to get it out. Jay took it out almost all the way and asked her if she was sure she wanted to stop. Something came over her and she whispered to him "fuck me" and he slammed his cock as far in as he could go. He pulled out after a few mins. and blew his load on her stomach. Jay said thanks to her, and asked if she was ok. She said it hurt but she would be fine.
Jay fucked her dozens more times and they broke up about 2 months later and 2 weeks later we started dating, eventually married.
100% as best she remembers it, and it turns me on just thinking about it all.