They say payback's a bitch but in this case payback is two boss bitches. Sam thought no one would ever know he leaked an embarrassing video of his friend Penny but of course she found out. For her sweet revenge Penny gets her friend Bella to agree to put the beatdown on the undersized Sam while she films the whole thing. Bella has plenty of mixed wrestling humiliation experience so little Sammy has no idea what is about to hit him. Bella has him on the ground pinned and struggling before he can even stammer out an excuse. Penny holds the camera and mocks Sam during his entire beating. Soon as he is almost too weak to resist the two girls start to strip him while pathetically tries to wiggle away.When he tries to hide his little junk from the camera Bella just puts him into a grapevine so he can't cover anything. Getting his ribs crushed by scissoring, his head sat on plus wedgies, wet willies, and even imposed stripping on camera are all not nearly as bad as what Penny has planned for her final touch.

Penny Barber is a proud nerd so when Sam makes fun of her for attending an anime convention she of course had no choice but to tie him up, pull his pants down, and draw NARUT0 whiskers on his face! After walking in on Penny in only a t-shirt and panties Sam is already hard before she even finishes pantsing him. Penny teases his little boner while making sure he knows how unimpressive it is to her. After she is sure Sam has been embarrassed enough for daring to tease her Penny tells him her new plan- lock him up in her cute little chastity device and make him watch anime in her room while she takes his car to the convention! Until he convinces Penny that he is an anime expert Sam's cock will stay locked.

Sam had a very memorable first encounter with Lola Fae and they were bound to meet again since she is fucking his roommate on the regular now. This time Sam wisely attempts to flee the tiny terror as soon as he spots her but Lola is not going miss another chance to bully a little loser. She reminds him that he lost their bet about his penis size and so he owes her some oral satisfaction. Lola tells him that getting her ass eaten by a little naked cuck is the perfect way to get warmed up for her date. Lola might have just stripped him down and sat on his face but she had to stop for some wedgies once she saw the tighty-whities he was wearing. Once she does get Sam in his proper place on his knees with his tongue up her ass Lola spends the rest of their little hangout switching between moaning in pleasure and making fun of Sam's itty bitty boner.

Penny Barber's Office Pantyboy Your least favorite co-worker holds your career and dignity in her hands now that she caught you embezzling on the same work computer that you were looking up panty fetish porn. She has double blackmail dirt on you and she has used it to turn you into her office plaything. Your new work routine starts off every morning with a pair of her dirty panties and some incredibly humiliating jerk off instructions. Penny has no mercy on you but at least she lets you see her round ass and bare pussy while she is commanding your little cock. Premature Ejaculation JOI from Boss Luna Sapphire You knew looking at porn on the job was a terrible idea but worried about getting fired, not screwed over by your hot supervisor. Luna calls you into her office and explains that she has been monitoring you and your embarrassing fetishes for weeks. She even knows from your search history that you have a tiny cock and a problem with premature ejaculation. Luna already told her friends in the office but she promises not to tell the big bosses if you promise to be her little errand boy from now on. You also have to pull out your little dick and prove that you really are a pathetically quick squirter. Luna might even take it easy on your future humiliations if you can make it five minutes jerking off for her. How long do you really think you can last after she strips naked and starts wiggling her bare ass in your face?  Small Penis Teasing After Office Fling "I was really nervous to see you around the office after we hooked up until I realized the only person who should feel embarrassed is you. It is obvious from the way you have sex that you are clueless about my body and your own. I mean, if you realized how small your cock was then I think you might try a little harder in bed. You actually think it is above average?? Well luckily we have a ruler and the internet to prove that completely wrong. Unless you want everyone in the office to find out the tiny truth then you are going to put that inflated ego to work for me. From now on, you will tell everybody how much you love all my ideas and projects or risk your dick becoming the punchline of all the ladies room jokes. You will not just be metaphorically kissing my ass publicly, you will be doing so literally in private whenever I ask. Since you still owe me an orgasm from the other night now is a great time for you to practice eating pussy from behind." 

Juliette March usually gets along well with her roommate Sam, even though she is a fitness loving health nut and he is a video game obsessed slacker. Juliette is getting a little sick of Sam dominating the living room for his dumb gamer sessions so she sets herself up for yoga and dares him to make her leave. Juliette then spends the next twenty minutes proving to Sam that he is definitely the weakling of the house. She overpowers the skinny wuss and has little trouble switching between different pins and holds. Sam refuses to admit that he is getting his ass kicked at first but when Juliette switches from wrestling to stripping all he can do is squeal for mercy. Soon, Sam is totally naked with his head squeezed between her thighs and his little boner gripped in her fist. That is when Juliette decides to really humiliate him...

When Ella Nova was finally fed up with her roommate, Sam, she banished him to a dimension of humiliation called THE FEMDOM ZONE. A purgatory of eternal embarrassment where nothing makes sense and every orgasm begins a new sexual nightmare. Sam must make it through office spankings, classroom wedgies, panty punishments, and sci-fi SPH from a femdom demon.