Glad so many guys have experiences with this. I had a feeling!
My story hasn't yet happened...but if I get the guts, it (could) become a reality. Basically, my buddy from college and my college girlfriend REALLY despised each other back in our college years. Long story. He broke her friend's heart our freshmen year...and they had really opposing personalities and political beliefs. She was far to the left, he had recently come out of the military. I was able to have relationships with people with varying views.
Anyway...I broke up with my girlfriend over a decade ago...but I still have some delicious nudes of her in her early twenties. Back then, she let me take pictures of her completely naked...trusting 100% that I wouldn't show them to anyone. Afterall, she was a feminist, borderline hippy girl in love. (Sidenote..it was true that I never would have shared her at the time. But several of my friends have enjoyed her since

.)
Anyway, I still see the guy friend every so often. Maybe once a month. I might touch base with my ex once a year on Facebook...but nothing more than that. We've talked about her in the time since. He says things like..."yeah man, I get it...she was a good person...and really hot...but I'm sorry...she was annoying as fuck!"
Here's where the pervy thought comes in. I haven't been able to make the offer yet because it feels too mean to her...but man, I would get a lot effed up pleasure from letting my buddy enjoy her completely naked, full frontal body. With her big happy, girly smile across her face. Back then, she would have been MORTIFIED by the thought of him seeing her like this. That's part of what turns me on about it. I would loveee to watch him carefully study her pussy.
Anyway, I can't think if anyone she would want to enjoy her naked body less than this friend...which is the main reason I haven't wanted to do it...but also the main reason the thought turns me on so much.
What do you think, should I?