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  • SRJ
    Junior Member
    • Jan 2026
    • 9

    Originally posted by Susanna McDonald

    I dated a cuckold guy when I was in my 20s although it didn't start off like that and I had no clue at the time that there was a term for such a relationship.

    I was in a very short relationship with a guy I had known in college. Really sweet guy but the sparks weren't there and I tried to call it off after a few months. He said he still wanted to be friends which was cool with me although I knew he was hoping that we would become an item again. I figured that as soon as I started dating someone new, the first guy would get the message and move on. Instead, he went out of his way to tell me how great he thought it was that I was dating someone new and how OK he was with it. It got to the point that he we were talking on the phone or over a coffee almost every night or every morning after one of my dates. I was reluctant to go into detail at first but he kept asking and eventually I stopped holding anything back. We talked about the kissing and sex and everything else in a detail that I have never even shared with anyone else. At the time, I started thinking that maybe he was gay and I kinda enjoyed the 'girl' talk with him and the support that he always gave me. Whether a date had gone good or bad, I could always count on having him available to talk it out afterwards.

    It was only after six months or so that he sat me down one night and told me how much my sleeping with other guys had turned him on. The problem was that he also wanted to start becoming sexual with me again while still giving me complete freedom to go out with other guys. I never let him have sex with me but I let him do a lot of other things and, while the physical sensations were nice, it really made me feel guilty like I was taking advantage of him in some way.
    Just curious was he on the smaller side or was the sex not great like maybe he didn't last?

    Comment

    • Maggiemoo
      Member
      • Jan 2026
      • 11

      I've not dated someone like that but my friend dated a guy who would enjoy watching me wank off my man while they both watched. My man at the time had an average size **** but we'd say it was bigger than it was. Another friend would say her partner had a huge one which seemed to be a turn on. One time she met a guy online who came over and just pulled out a huge **** and had a wank and left. I don't have an issue with it but I don't think I'd be attracted to someone who thought they couldn't satisfy me.

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