I fucked my girlfriend's mom on the couch while my girlfriend was in the next room passed out drunk. Mamma gave her the liquor!
Cheating. Paying to cheat is probably up there, too.
Learning to draw the human body becomes a lesson of another kind.
The woman by the pool shared her art ... and so much more.
Lucy's Body of Art - Wherefore Art Thou comp entry
When I was about 16, I made out with the girlfriend of one of my best friends. A couple years later, I did it with a couple sisters -- separately, but on the same night in the same house -- and they both were statutorily a few months too young for me. Then a few years after that, I became a boy toy for a much older gay work colleague.
After meeting a woman for dinner whom I had met on an online dating site, I realized she had misrepresented herself somewhat by posting pics from when she was obviously much younger and hotter. When she arrived at dinner and I saw her for the first time in person, I was disappointed but entertained her through dinner. Then to teach her a lesson, I took her back to my place and treated her like an amusement park ride. I fucked her face until she gagged, I fucked her up the ass, something she claimed had never been done to her before, then finished in her pussy, purposely busting my nuts deep inside of her. Once I was done with her, I sent her packing and emailed her the next day telling her I never wanted to see her again. Ever.