Cucked and sissified

Five years ago today, my wife came home from work and admitted she had kissed a coworker (Jack) in the elevator. She was remorseful and apologized and I thought that would be the end of it. She mentioned it several times in the following weeks and it became clear that she liked it. Eventually I asked her if she was attracted to Jack and she said yes...very much so. He was a big muscular alpha male and she could not stop thinking about what sex with him would be like.

I has always been attracted to her friend Jane and thought there might be an opportunity to kill two birds with one stone. She gets Jack and I get Jane. Honestly, I would have been okay with her having sex with Jack without making a deal as we only live once. But why not get a little something myself. It was a long shot but I made the proposal.

The next day she came home from work and said “Done!” She and Jack spent the lunch hour having sex in a nearby hotel and then again after work.She gave me the details, including his penis was much larger than mine and they both came multiple times (she was on the pill). Then she mentioned that Jane was in with our little agreement and would be coming over Saturday while my wife went out with Jack. Immediately I almost forgot about what happened that day and focused on Saturday with Jane.

It was odd seeing my wife get dressed up to go on a date and have sex with another man. My wife did notice that I had an erection and said “Jane will be here soon to help you with that “little thing,” which for some reason made me even more aroused. About 30 minutes after my wife left, Jane arrived at the door. It was awkward as we had not spoken to each other directly, but we made small talk and headed to our pool to relax. Jane asked how it felt knowing a big alpha like Jack was with my wife. Initially I responded that she should be free to have sex with others if she wants.

Then the conversation turned towards me. My wife had told Jane I had a small penis and she wanted to see it. Embarrassed, I reluctantly showed her. She told me to play with myself while she watched and I complied knowing it would payoff. She laughed and made comments about my tiny little thing and then said “let’s get this over with.” It was at that moment I realized Jane was in control.

When we got to the bedroom, Jane had me lie naked on the bed and play with myself while she undressed. After a few minutes she laid next to me and began to rub my penis. She kept saying she only need two fingers because it was so small. The more she said it the more I began to like it. Then, without notice, she stuck a finger in my butt and then a second and finally a third. My wife had done this a couple of times, but not like this. I was paralyzed. I was told to get upon my hands and knees and close my eyes. After a couple of minutes I felt a cool gel in my butt, followed by excruciating pain. As I looked over into the mirror, I could see that Jane had mounted me with a strap on and was working it deeper into my ass. After a couple of minutes the pain was replaced with the sort of pleasure I had never experienced. Jane noticed that I was now pushing myself back into her “cock” and calling me a sissy. This went on for about 15 minutes until Jane sat on my face and would not move until I made her orgasm.

Just as that happened, I heard the front door open and two voices...Jack and my wife. They walked in to see Jane sitting on my face and still wearing the strap on. There was no confusion as to what transpired, so no use in lying about it. They all laughed and called me a few derogatory names and then went into the living room. I showered and then embarrassingly joined them..to find them watching a video of Jane and I.

That was just the beginning. After that Jack had sex with my wife often on the next two years in our house and most of the time I was his personal fluffer to get him ready. Jane used me a few times and added others for more humiliation. On some ways, these were the good old days.

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Tim Sex August 09, 2022 at 9:30 am 2 0