Amarna Miller is attending a business conference with her co-worker, Sam, that she knows has a little crush on her. Amarna has had fun teasing and frustrating him while they share a hotel room but when Sam refuses to do her a little favor she takes the teasing to a whole new level! She asks him if he would go pick up her phone that she left downstairs but Sam says he "won't move an inch" so Amarna decides to prove who is the real boss. She bets she can get him to move an inch and then crawls on top of him to put her pantied ass right in Sam's face! She giggles as she sees the instant boner bulge in his pants. Sam resists her wiggling and teasing for a while but soon Amarna unzips his pants for the next phase. Right when Sam probably thinks he might get a blowjob from his crush Amarna starts smacking and punishing his little cock and balls! Outsmarted and totally humiliated, Sam is to accept his place as Amarna's butt kissing errand boy.

A Girl Bully always collects on her debt, even if she has to lock up your cock and throw away the key. That is exactly what happens when your roommate, Penny Barber, finds out that you are taking your girlfriend out to a very expensive restaurant even though you are behind on rent. Penny knows you are such a horny loser that she could easily seduce you, even if you are about to head out for a date with someone else. Once she has you tied up with your pants down then the chastity cage comes out. Hope you weren't planning to get laid after your fancy dinner! Penny has a great time making fun of your little dick while she flicks your boner until it soft enough for your new cock cage. She promises to give you the key once you have paid her back every penny you owe. Until then, she is going to use her big soft tits and perfect round ass to make sure you understand exactly how painful chastity can be.

In part 1, your roommate Penny Barber stripped you down and locked up your cock right before your big date. She has kept your dick prisoner until you paid your back rent. Now you are finally ready to get unlocked and go on a nice romantic date with your girlfriend. Too bad Penny has other plans for you. Just because you are getting out of chastity does not mean Penny doesn't still own your little dicklet. She is going to stroke you off to make sure you stay all flaccid and tiny for your entire date night. Your little balls are going to go from bursting and blue to sore and drained in just a few minutes. All you can do is lie there squirming and blushing while Penny makes fun of you for being a small penis premature ejaculator as she steals every last drop of your cum.

Tabletop gaming nerds like to talk about sex as much as anyone else so Sam was not surprised when someone started a bet about which role player had the biggest cock. He should have known better than to lie abut his dick size to the hottest girl in the group. Penny totally believes him at first and asks for a picture so she can show everyone that Sam is the winner. Penny is not even suspicious when he refuses since it is totally normal to be shy about dropping your pants in front of a sexy, confident women like herself. When she starts to hint that she might be down to give him a blowjob before the rest of the guild arrives and Sam still seems terrified to let her see his supposed seven inches, Penny realizes he must be lying. Penny is not they type to laugh something off to protect a fragile ego so she just takes matters and Sam’s dick into her own hands. She is going to measure that liar’s little boner and if he is one centimeter short of seven inches, then Sam is really going to wish he had just admitted he was hung like a pixie.

Penny is bored and horny, which is usually not good news for you. She orders you to wear her panties and start worshipping her ass, just as a warm up. Once you are done servicing her with your tongue in every way possible, she finds another use for your face. Penny wants to ride her favorite dildo while it is sticking out of your mouth. She also makes sure to keep reminding you that you are nothing but a panty slut boy toy with a dick too small for sex. When she has had her fill of cumming in your face, Penny finally turns her attention to your cock. Submissive boyfriends with tiny cocks can still get handjobs, as long as they are fine with being stroked off while getting fucked in the ass, of course.

Penny knew it was a mistake to let her husband's loser friend, Sam, stay with them after he lost his job and she makes sure to remind him of his inadequacies whenever possible. Penny finally snaps when she finds that Sam isn't even correctly handling simple chores in place of rent, like washing her lingerie. Sam is going to get the treatment he deserves for his immaturity-pants down, bare ass spanking! After she confronts him about not washing her undies promptly, Penny easily strips the little wuss despite his protests and struggles. Then she grabs on to his little stiffy to use has a handle as she shoves his face into the basket of her dirty panties while turning his butt bright red with a punishment spanking. Sam begs for her to end the humiliation but Penny does not let up until he agrees to wear a panties only uniform until he moves out.   

When Sonia confronts the couple down the hall about keeping down their loud sex, they just laugh in her face and ask if she wants to join them. Sonia does not laugh but she does accept the offer. The poor little partiers were not prepared for the humiliating femdom threesome that Sonia springs on them. The hot blonde gets stripped and panty-gagged while her "man" gets his cock mocked and his face sat on.

You messed up the hotel room reservation for your big work conference and now you have to beg your colleagues to crash on their floor. Unfortunately, the only one who says yes is office bully, Penny Barber, and she will only let you stay if you agree to follow her six rules. All of the rules are mean and designed to demean you but by far the worst one is that you are not allowed to wear any clothes in the room all weekend. Penny demands that you get naked before she even finishes reading the rest of the rules. She mocks your boyish underwear and undersized cock while she flashes her tits and pussy at you. It is not going to be a weekend of blue balls though, because Penny is also going to make you jerk your little dick for her amusement. If you don't want to kiss ass and cum on command then that is too bad because Rule 6 clearly states you must obey any and all instructions from Penny