The only thing more fun than teasing a man in chastity is teasing one who THINKS he has a chance to get his little cock out for a pity orgasm. Penny has a little chastity challenge for Sam that she knows has almost no chance of success for Sam. There his a high chance that she will find his tears from blue balls hilarious though! Penny strips him down to his little pink undies and puts the key where he can almost reach it then starts to give him a lapdance in just her lingerie. If he can get his cage unlocked and finish wanking before her strip tease is done then he gets to cum. If not... Penny is going to ice down that little boner and put it right back in it's pretty pink cage for another month!

When Juliette March is shockingly dumped by your roommate before their vacation she heads to your room for some revenge sex. This is your chance to cuck your jock roomie and experience the amazing ass you have been drooling over for years. Juliette strips down and is just about to start a warm up blowjob... then bursts out laughing at the size of your tiny boner! She really wanted to teach her ex a lesson but she says that fucking you would be more embarrassing than getting dumped. Juliette does keep playing with your little dick and wiggling her bare butt in your face in between giggles. You might not be getting laid but at least giving you a humiliating little orgasm does cheer up the broken-hearted girl.

Pantyboy Humiliation On Graduation Day I cannot believe the pervy little neighbor I used to babysit is finally graduating! I was just about tell you how proud I am of you for graduating college right when I notice you looking up your friend Ella's skirt! Looks like the graduate STILL can't control his eyes near girl's panties. It is a little funny that you happen to be caught looking up someone's dress on the one day you are wearing a gown... Maybe spending the rest of the day wearing nothing but Ella's pink panties under your graduation robe will teach you a lesson.

Last week your roomie’s girlfriend almost fucked you but only gave you an embarrassing little handjob because you’re dick was too small for her. Then she got back together with your jock housemate and now Juliette is worried things could get awkward. She is pretty sure you don’t want everyone to know that you have a tiny penis but she wants to be sure that little handjob incident never gets mentioned again. Juliette leads you to believe she is going to entice you with sex to keep the secret but her plan is a lot more diabolical. Instead of slipping your cock into her pussy she slides a pair of pink panties onto your little butt! She gets some nice photos of your itty bitty boner straining inside the girly undies to make it look like you love it. Juliette does not stop there because she wants to be sure you have a secret that is more embarrassing than her cheating mistake. You wouldn’t want everyone to see evidence that you are a little sissy who loves to cum in his pretty pink panties, would you?