When Alex found out Sam would be on her team for the big work conference she made sure the little wanker was sharing a room with her so she could keep an eye on him. Alex is ready and waiting to put him in his place when Sam tries to slip out for a night of drinking before their early morning presentation. She confronts him with some uncomfortable truths, like he is never getting laid at the hotel bar AND that he is long overdue for a trip over her knee... with his pants and underwear down around his own! Alex knows that Sam's lude jokes and generally oversexed behavoir has become a distraction around the office and a good bare bottom spanking is exactly what is needed to get this little twerp under her control. While she pins him down and turns his cheeks pinker with each smack Alex also lets him know that everyone in the office has already heard how small his cock is and that he is the reason they installed special porn blockers on the work computers. This corporal punishment and degrading lecture are still not quite enough humiliation to satisfy Alex though. Sam has to prove he learned his lesson by getting down on his knees to kiss her big, beautiful boss butt!

Penny is a very busy woman, which means sometime she has to take important phone calls at the same time she is getting her body worshipped! Lucky for her, she got enough business done while getting her clit sucked that she can relax and enjoy getting her ass licked. Penny stands up so her sub can cover her round cheeks in worshipful little kisses then moves to the bed to lie down so her boytoy can fully bury his face in her ass for some proper licking. Penny does give his slutty mouth a short break so she can check his cute little stiffy and make sure his own bottom is still red from the spanking she gave him earlier. Once the brief inspection is over though, his lips better get right back to her butt!

Juliette March wanted to get a little petty vengeance on her ex-boyfriend so she asked her bestie, Sam, to help make a fake sex tape. Sam is the timid nerdy type so Juliette asked him to wear a chastity device so he wouldn't get too excited from rubbing against her naked body. Juliette is super grateful for his help but she kind of ignores his request to remove the cage once the fake porn is finished. There is something intriguing about her normally shy friend sitting on her bed wearing nothing but his little penis prison. The feeling of knowing that no matter how badly she teases him all he can do is wince and whimper. Instead of unlocking his cock, Juliettle starts seeing how tight she can make the chastity cage while playing with herself right in front of Sam. He tries to complain but the grinding, rubbing, and licking all over his trapped dick has his poor brains so scrambled that Sam soon agrees the chastity device will stay on until Juliette has had her fun.

Exactly thirty days ago Juliette March convinced her roommate to lock his dick in a chastity cage so they could make some fake porn.Then she convinced him to keep it on for a whole month, just to satisfy her own curiosity about his reaction to going so long with no orgasms. Juliette did promise that they would have sex when his thirty days was over, though. The time has finally come but she still seems more interested in teasing him than fucking him. She gives him lots of little kisses all over the cage and gets her poor roommate so worked up the device almost gets stuck from his cock straining to grow. Juliette actually mentions that she thought it would grow a lot more once it was finally out of the cage, just casually adding some small penis humiliation to go with his aching blue balls. Juliette takes her time cock teasing with her mouth, hands, and naked body while sprinkling in embarrassing comments about how desperate and eager his little dick must be by now. Juliette totally appreciates what a good sport her friend has been about her chastity fascination but still wants him totally overwhelmed with horniness and humiliation on his first night out of the cock cage.

Star is having the best week at the office now that her old wedgie victim is her new temp worker. She makes him wear tighty-whities to work and start off each day by begging for a wedgie. Star is a very experienced bully so she knows to keep pushing the limits to make sure her office boy stays squirming with humiliation. Today she decides to add some embarrassing labels to his little boy undies since he already has his name written on the waistband. Once she is done marking him with a sharpie then Star yanks his undies up nice and high so his undies, and the embarrassing words written on them, are clearly visible all day long.  Even after all that, Star still does not let her humiliated wedgie worker off the clock until he completes a little light ass worship. 

You are always asking the woman in your life for little favors, whether it is your ex-girlfriend, step-sis, or old college roommate. Lily Lane is on that list of people but this time when you show up asking her to co-sign a lease, Lily decides to make you beg in the most humiliating ways she can imagine. You might have been shielded from the sting of your failures before but if you want Lily's signature today then you can ask nicely. While wearing nothing but her panties. And giving yourself a wedgie. Also sucking your thumb. She makes a little game out of coming up with fun ways to make you degrade yourself while she reads over the boring lease documents. Lily is pretty creative and pretty mean so jerking off while she makes jokes about your dick size ends up being the least embarrassing part of playing Lily Says.