Ella Nova knew she was taking a risk by inviting her buddy Sam to a sexy pajama party hosted by some of her cooler friends. So, of course, he shows up in a dorky flannel pajama set while she is wearing lingerie and stockings. Ella tells him that the only way to adapt his look for this party would be to go in nothing but his undies. Little Sammy is way too shy for that idea so they end up in a tug of war over his pants which leads to Ella grabbing his undies for a wedgie. Ella starts to take out her frustration with his poor outfit choices by tormenting Sam with wedgies and pantsing. She enjoys teasing and embarrassing him while he squirms and begs before she notices Sam is enjoying it as well. Ella sees that he has gotten a little hard-on from having his underwear yanked up his butt. Ella just grabs his boner and makes fun of him for having a small cock and getting turned on by wedgies. Sam may not make her look cool at the party but he will definitely be a conversation starter.

Penny and you are about to get hot and heavy as you listen to your spouses do the same in the next room. You are really turned on for your first time swinging with another couple and Penny is equally excited about this wife swap adventure. She goes to slide your boxers down but you helplessly squirt your load before your dick even pops out of your undies. Penny is so mad! She goes off about how it is no wonder your wife was into swinging since her husband is an utterly pathetic premature ejaculator and also mentions that your wife lied about your cock size. Penny threatens to march you into the next room to show your wife the slimy boxers and demand an apology for her husband’s juvenile accident. Penny decides not to ruin her own hubby's fun and just use a vibrator to get off while you both wait for your wife to finish getting the best dick of her life. Penny is not quite done humiliating you for your pathetic performance, even while she masturbates right in front of you. Once everyone is done fucking (or vibing in your face), Penny is still going to make you apologize to her husband and your own wife for being a tiny-dicked, boxer-creaming failure.

You almost blew your load when your girlfriend, Juliette March, finally agreed to have a threesome with her best friend, Lily Lane. Once they get you into bed they both burst into laughter and announce that Juliette is leaving you for Lily. Your new role in the house will be cleaning it while wearing a cute maid uniform. Instead of having mind blowing sex with two gorgeous women, you get to lie there as your now ex-girlfriend jokes to her new lover about your cock size, premature ejaculation, and a few other sexual short comings. The two girls do say you might get to lick their asses sometimes, if you earn the privilege. Lily actually offers to give you a pity handjob right now since your little dick won't be getting any other action tonight. 

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. Having a cute bare bottom at her mercy would be a treat even if she did not have a good reason to humiliate this hipster. If only all Cam’s little groupies could see him whimpering over her lap with his red butt spread open.

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! 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.

Scaring people can be fun but so can spanking people. When Sam puts on a monster mask and pulls a prank on Penny, she puts him over her knee and pulls down his pants. Penny makes his punishment even more embarrassing by talking to Sam like he is a silly and confused teddy bear instead of a frightening beast. He cannot even really protest at first because the mask he is wearing makes it impossible to talk.  Sam may have been joking around but Penny certainly does not stop at a playful smack on the butt. She uses his own belt on his bare ass and even drips a little hot wax on his vulnerable bottom. Sam will not forget this important Halloween lesson- frightening Penny just ends with her humiliating you.