Fast forward a month

Your mom and sister are pegging you daily in preperation for your 'debut'. They say you'll lose your anal virginity tomorrow - that's when the guy who put the high bid on it gets out of jail. Your sister's set up a web cam for it 'so whiteboys can pay to watch',

"You won't let him hurt me, right dad?"

"He paid a lot of money son. You gotta get used to a little pain. Learn to enjoy it. Here." He bends you over his knee and spanks you hard enough to break the skin.

Your cheeks are still raw the next day, when a guy who did seven years for armed robbery splits you open from behind. He fucks you as hard as any prison sissy, tearing your virgin butthole apart as you moan and tell him it's too big. Your eyes roll back in your head as he hits your prostate, and you feel the month's long build-up of masculinity in your neglected nuts dribble its way out of your chastity cage.

"Thank you daddy" you moan, drooling.