106 Votes
Prison Bitch (ch. 4)
Harvey is taken to the showers where he has to announce to everyone that he is the new prison slut, and he is given an agonising enema.
Topics: Enema, Slut
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Harvey is taken to the showers where he has to announce to everyone that he is the new prison slut, and he is given an agonising enema.
Topics: Enema, Slut
Harvey gets his cock stuffed and unwillingly enjoys every minute of it until he begs for orgasm.
Topics: Anal Sex, CBT, Humiliation, Master & Slave
Fido's owner takes him for a thorough examination, including nipple, cock and prostate sensitivity as well as having his virgin asshole checked for tightness.
Topics: Anal Sex, CBT, First Time, Humiliation, Punishment, Alpha Male, Face Fuck, Virgin, Master & Slave, Nipple Play
Harvey unwillingly enjoys getting his tight ass stretched.
Topics: Anal Sex, CBT, Sloppy Hole, Master & Slave, Ass Play
James realises that the Guards aren't going to help him - in fact, they're more likely to get in on the action.
Topics: Anal Sex, Big Dick, Humiliation, Punishment, Prison, Master & Slave
Kyle finally fucks the new prison bitch's virgin asshole.
Topics: Anal Sex, Rough Sex, Big Dick, Fisting, First Time, Prison, Virgin
Kyle meets his new prison bitch - a cute college kid with a pretty mouth and a tight, virgin ass.
Topics: Anal Sex, Big Dick, First Time, Humiliation, Prison, Alpha Male, Virgin, Master & Slave, Throat Fucking
Harvey is introduced to his training to become the perfect fucktoy. Part 1.
Topics: Bondage, Ass Play