We met when I was 26 and she was 23. At the time it was a blind date that one of her friends who knew me set us up on. Things went really well that night and we ended up having a heavy petting session in the back of my car after seeing a movie. I thought I was just the best guy walking around after being out with her twice and getting action on both dates but one of her ex-boyfriends decided to try to ruin it for me. When he found out that I had taken her out twice now he made it a point to come to my work and try to humiliate me by telling me that he'd fucked her before me. Another of his friends bragged that he'd had her the same night!
When Cassie found out she was horrified and tried to apologize but I wouldn't hear of it. I told her that I'd always found it kind of thrilling to know that the woman I was involved with had been involved with other men and I got off big time on knowing about their sexual history. Instead of that guy ruining our relationship he ended up making it into what it is today! That's what I wanted to start my little thread about Cassie's Adventures about.
After that revelation about what really got me off we had one of the best nights of sex I'd ever had. When we spoke again the next day she was convinced I was making it up but I told her about the girl I lost my virginity to and how I was more interested in how many of my friends she'd had before me. I thought about her fucking them even when I was losing my virginity to her and got off more thinking of how they had fucked her. Once this realization hit it was off and running and I learned all about her very promiscuous days and how many guys she had sex with in her teens and how she kept the practice going through college and her first job.
Her number when we met was 21 not including me. Our time together after these talks consisted of her telling me of a time she'd slept with someone else and me begging her for details. She started to get off on it and less then a year into our relationship we started talking about her having another man in front of me. We didn't know the terms "Hotwife" or "Cuckold" would apply to our relationship yet for a few reasons. She wasn't my wife!
but also I considered being a "Cuckold" to be someone that is humiliated by his partner taking another man because I would be "unable" to satisfy her. The truth was I never had a problem satisfying Cassie, she just has a very high sexual appetite and has her entire life! In those days, the internet wasn't something we understood and we didn't want to put out an ad looking for another man out of fear that we would be discovered. We wanted to keep our personal lives personal. We ended up deciding to proposition one of her friends from high school at her 5 year Reunion. He was something of a "boyfriend" to her in those years though she said it was never a relationship like that, she just liked the physical relationship with him. We had a few drinks and she brought it up to him privately. He was confused at first because she'd introduced me through the night as her boyfriend but she explained that I was open to it. He waited for me to be alone at the bar to ask me if this was true. I thought very highly of him for doing so and told him that it was.
We agreed to all go back to Cassie's parents house and have some more drinks. He followed us and she asked me as we pulled in the driveway if I was sure about this and I showed her my hard cock which made her grin. We had some of my father-in-law's good scotch and relaxed in the living room. Her parents were at some sort of weekend trip for my father-in-law's Lodge. After some drinks Cassie started to get very touchy and sat on the couch with him. I encouraged them with nods and smiles until I finished my drink and suggested we go upstairs.
Her parents had invited us to sleep in their bed while they were away but we had slept both nights in Cassie's old bedroom. I got harder thinking of how many times she had been in this room with this guy and had sex with him! Cassie had worn this beautiful black and white dress that zipped up the back. I'll never forget moving a folding chair in the room and hearing them kissing and looking up just in time to hear the zipper pull down and the dress slide right down her body to the floor! He moaned a few moments later when her hand found his cock in his pants.
I sat across the room and watched in the little light in the corner of the room when she got on her knees next to her bed and sucked him. I watched him strip my girlfriend's panties and bra off and mount her. I moved closer when he started to push inside of her and held her hand. I kissed her hand when he started to fuck her. He was amazing. I could hear the pleasure in Cassie's voice and see through her actions like raising her hips up, wrapping her legs around him and gripping his ass with her free hand how much she was enjoying herself.
He fucked her well and I enjoyed my show. We hadn't discussed where his cum would go and as he was about to ask where it should go he said he saw me kiss Cassie on the lips and started to cum. He pulled out after his first shot went inside of her and let the rest shoot all over her belly. They caught their breath and he said it was getting late for him. I helped find his clothes and walked him out. He shook my hand and thanked me which I appreciated and went back upstairs to find Cassie still on her back on the bed. I stripped naked and climbed between her legs and rubbed myself in the now very sticky and cold cum on her belly before inching my way towards her pussy.
We had a very, very slow session where I told her how turned on I was watching her fuck someone in the same bed she'd fucked him in so many times. She started to count the number of times he'd fucked her in her bed and I started fucking her harder. I came when she said "Oh and he fucked me here tonight" and came right inside of her before adding some of my cum to his on her belly. We fucked 3 more times that night.
Our relationship changed from there for the BEST. I was worried if it didn't go well that it might be the end of it but she said the next morning that she had such a great time and loved seeing how turned on I was and how it made her more and more wet which made him fuck her harder which got me off more and how it was such a great cycle we had. We talked on the long drive home that we should find someone she hadn't fucked yet and add to her totals and less then 2 months later we did just that.
That's another story though!
They had sex again after a lot of coaxing from her hands and mouth but she said he couldn't finish.
he had forgotten to get condoms and didn't want to play without them. He still fingered her and ate her pussy, she said she had sucked him for a little while but he was so much more interested in her. I didn't blame him!