Star Nine is a woman who thrives in a very dangerous line of work and she has almost zero tolerance for frivolity or weakness. After an encounter with her immature neighbor, she became deeply offended by his lack of discipline and dignity. The super spy gave him two chances to prove he deserved to be treated like a real man and he failed utterly. Now he lives as her little sidekick under constant supervision with daily punishments designed to humiliate him into growing up. Star keeps him dressed in tiny shorts and tighty-whities with a hat that says CRYBABY across the front. He has to kiss her bare ass at regular scheduled intervals and he never gets enough privacy to even think about jerking off, let alone getting laid. She is also constantly giving him manhood tests like her latest ultimatum- decide which option a real man would find more degrading, a chastity device or babyish little cartoon panties.

What is more humiiatiing than getting caught with a stiffy by your hot friend? When she makes you pull it out to see how little it is! Penny knew her outfit showed off her ass pretty well but did not expect her pal Sam to pop a boner just by seeing her in it. She makes fun of him of course but actually thinks it is kinda cute that he can't help getting a tiny erection over her and is sooo embarrassed about it. Penny decides she is going to give her little friend's little friend a treat. She will happily stroke him off... as long as she gets to keep teasing him about having a little dick and laugh in his face when he squirts!

Penny was so excited to catch up with you on your visit back to your hometown from the big city. She was planning to consummate all the flirting that you two had done back in the old days. Then she sees that you had good reason to be shy back in high school. You have the smallest cock she has ever seen! Penny might not have much experience as some city girls but she is happy to name every guy in town that has a bigger dick than you. Penny is a very sweet girl so at first, she tries to help your boner grow instead of immediately laughing at you. She flashes her big beautiful tits and wiggles her nice round ass in your face. Eventually, the encouragement slides into disappointment with a few giggles mixed in. Penny might not see you as a real man anymore but she is such a polite country girl that she might just take pity on your embarrassingly tiny erection.

Tommy King aka Tommy Mommy has been playing her guitar every Thursday night at the local club until little fuckbrat Cam Damage stole her gig! Cam is a hot trans guy who is new in town and Tommy just knows the bar manager chose him more for looks than musical talent. Her embarrassment at being replaced is going to be paid back big time, though. If Cam is such a stud then he shouldn’t mind playing his first show completely naked! Her revenge plan gets off to a good start when she confronts him in the greenroom of the club but then Tommy gets a little distracted by the fact that Cam is actually pretty hot. Squeezing his ass is so fun she decides to stop the stripping for a spanking. After getting the arrogant Cam into the right mood by stripping him naked and spanking his bare butt bright red, Tommy is ready for the next step in her revenge. She heard Cam say that if she didn't like losing her gig then she could "lick his ass". Tommy is going to make sure Cam regrets that choice of words by having him spend some quality time with his face in her butt cheeks. She makes him lick her pussy and asshole while telling her all the reasons her band is better than his. After the spankings and face sitting has fully humbled the little hipster, Cam is now putty in Tommy's hands. She definitely still plans to humiliate him on stage but she has something better than nudity in mind. Tommy had a shirt with the words TOMMY STEP-MOMMY MAKES ME CREAM MY PANTS printed on the first. She is going to make him earn that embarrassing shirt and give her a few orgasms before his big debut.