Many years ago I (33M, then 23) moved to a new town and ended up picking up a woman (42) who was newly single after a long and messy divorce. She told me she wanted to be a cougar and be slutty now that she’s divorced. She said her kids were with their dad that weekend so she would “educate me”. Before meeting her I’d only experienced the three basic sexual positions and blow jobs with my only gf in college. She was the first person I had anal sex with, first time I ever tried kink, first person I ever came inside of (vaginally, anally or orally), first person I regularly had unprotected sex with, or gave a facial to…and the list could continue. It was arguably hottest experience I could have imagine. We ended up hooking up a few times with her as my “sex teacher” (her words) off an on for nearly two years until I moved. I give her 100% of the credit in my sexual competence.
It’s probably clear where this is going. During orientation at business school I met a woman and hit it off. She told me she was from the town I’d moved lived in, but it was a bigger city so I didn’t think anything of it. Plus it had been nearly six years at the time. We started dating after a few months and nearly a year later I met her mom…who turned out to be the cougar. Neither of us behaved strangely when we met and never said a word to one another about our hookups, we knew that was a different time and would never be tempted to hook up again. She got remarried and the guy is great and has been very welcoming.
But knowing that my soon-to-be wife’s orgasms are from “lessons” her mom gave me has started getting to me. My fiancé will drunkenly brag how good I am in bed, but it feels odd knowing that’s from her mom. (Side note: luckily the apple didn’t fall far from the tree and my fiancé is insane in bed, most of what I experienced with her mom I didn’t experience again until her.) Admittedly I do find it hot and occasionally still jerk off to the woman who will be my mother in law, but will feel regret immediately after. I do have some guilt but great memories.
Source: reddit.com/r/gonewildstories/comments/qj0y6f/fiancés_mom_mf