I wrote previously about my first cuckold girlfriend after getting divorced (who cheated on me with her ex), but I would like to share a story from my second girlfriend, who I explored cuckolding with over many years. We experimented with a lot of different dynamics, but one that we both really enjoyed was "cheating", where the other man believed she was cheating on me and derived feelings of sexual superiority and power from that.
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When we were both in our early 40s, we had started to live together, blending families and friends, keeping our cuckold activities private and separate. One friend who I would go out with a lot was married with a great wife and kids, but he was pretty much the biggest arrogant prick I have ever known. We did things together with them as a couple, and my girlfriend hated his attitude and the knowledge that he cheated on his sweet wife. With that said, she started to admit she had fantasies of him using her and kept bringing it up, until finally we decided to let it happen.
He was not the most attractive guy on the planet, but he just had that kind of attitude that made it easy for him to hook up with women. He liked to tell me during our after-bar talks (where he often got blowjobs or sex from women in the bathroom, car, etc.) how he loves his wife and how he would kill any guy who tried to fuck her. He told me how much his wife liked me because I was such a nice guy, and she trusted him to go out with me instead of some of his more douchey friends. He would then give me these warnings about what he would do if I looked at her the wrong way, to which I would always assure him I would never do that. This was pretty arousing for me, especially since my girlfriend told me how much he hits on her. It was also a big trigger for me because it was almost identical behavior to my earlier girlfriend's ex-husband.
The affair started easily one night after he and I stopped at my house after the bar. I pretended to have drank too much and passed out in our bedroom, while he proceeded to fuck my girlfriend on the couch. I ate her out after he left while she told me how he was rough and a pretty much a dick, and it turned her on. We both agreed to let it develop.
The "affair" went on for months. My girlfriend was happy that his marriage, job, kids, etc., kept it to a reasonable pace. He liked to get her underwear and outfits to wear, and especially liked seeing her in things he chose while she was with me. This turned me on like crazy, and I found myself confiding in him about her during some of our drinking nights out. I could see him squirm and even rub his pants at times when I would tell him how she denied me sex or only wanted oral. Sometimes I would tell him that she is not very sexual and would never do oral or anal, knowing that he loved to make her do those things. I would mention how I felt insecure from a sexy outfit she got or from mysterious texting or unexplained outings. He would reassure me it was all good and to trust her, and that would make my little dick leak.
Probably the pinnacle of the affair experience for me was a Super Bowl party that he and his wife held at their home. He told her to wear this sexy sweater dress he had given her. The weather was still chilly, and she wanted to wear leggings, but he said no, and instead gave her a pair of his wife's panties to wear. I still remember his wife when we arrived telling my girlfriend how brave she was wearing a dress in this weather. The party was typical for a Super Bowl, with 4+ hours of people getting drunk and making noise. This afforded him a lot of opportunities to steal gropes of my girlfriend in the kitchen and other rooms, and get blowjobs and fuck her in the bathroom multiple times. At one point she came back and sat with me, whispering in her drunken breath for me to feel his cum. I looked around quickly and stole a feel up her dress, discovering her panties gone and her thighs slick with cum, her pussy sopping and open. A few minutes later, my friend came in, gloating as he sat by us and talked to me about the game. I found myself turned on when he asked me to grab him a beer.
The affair ended after they moved out of state, but it was very hot while it lasted.