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Originally Posted by Dookieman
There's 2 of my mother's friends that have always been extremely sexy. Even as I had become a young man and they were then "old" ladies... I still found them to be HOT...and yes I would absolutely pounce if they were down for it. One of them worked at the same place I did for a few years, so I had the pleasure of seeing her on a daily basis. She's very prim/proper and "religious" so that was always just a longshot fantasy that would never really happen. There was another older woman at work that seemed to be "into" me but I squandered the opportunity (she's definitely in the old "cougar" category; old enough to be one of my mother's friends).. at the time I was worried with how risky that is to hook up with any co-worker, considering how things are in modern times.
Other than that---one that is "unusual" imo deals with some apparent exhibitionist tendencies. The idea of a female friend (*just* friends) accidentally "catching" me either partially nude or actually jerkin off was always a hot scenario to think about. Actually any "sudden accidental nudity" situation amongst friends always ranks high with me.
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The idea of a very attractive woman I know platonically, .. or better yet a GROUP of attractive women I know catching me totally naked or jerking off is a very HOT scenario. I imagine their eyes would go wide as saucers as their mouths dropped open, hands would rise to cover their expression as they gasped out a shocked "OMG!! I'm sorry"... or suppressed a few giggles... but then the shock would give way to smirks and evil grins as they began relishing catching me like this, and shamelessly staring at my nudity, encouraging me to continue putting on a show for them.