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We chatted for a while in the kitchen as we enjoyed our dose of caffeine, not about anything in particular, just small talk, as in truth I was perhaps as nervous as she was about her caning. Despite my years of experience and with countless well-punished female bottoms to my credit, being asked to administer the first ever caning to the wife of an acquaintance was a little uncomfortable for me. I had always found Michelle attractive, extremely attractive, I could never deny that and whenever she was around, my eyes grabbed every opportunity to scrutinise this lovely woman hoping she had never noticed my attentions. Michelle had never given away her exact age, but from the conversations we’d had in the past, I knew enough to be sure she was somewhere between early and mid-forties. With my own fortieth birthday looming, I had become aware of finding myself ever more inclined toward attractive ladies with a certain maturity. Michelle certainly fitted the bill, beautiful, elegant and. Then i dressed her and layed her on the couch. When she woke up i was watching TV. She asked what happened and i told her she fell asleep and was out for 8 hours. She responded by saying wow, that long, damnt that couch really hurt my ass. Now that i had acted on my fantasys of fucking my neighbor ann. So now i set my sights on a classmate of mine sherri. Sherri was a smokin hot 16 year old . She was Latina and had an very athletic body with huge c-cup tits. She was an athletic girl who played varsity girls basketball. I loved to watch her run up and down the court, her tits went up and down every time. After about 1 week of following her i had my plan of action. It was simple really. Every friday after her game she would stay an extra hour to practice her free throws. The coach didnt have time to stay so she left the locker room door open for her to shower and when she left the janitor would lock up on his way out. It was the perfect plan, after the game i just hid in one of the.
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