After Penny stole his girl, Sam had to accept a new life as their little cucky houseboy. Bambi has started to like humiliating Sam almost as much as Penny and she loves teasing him about what he'll never have again. Just to give herself an excuse to punish Sam and humiliate him for fun Penny decides to trick him into walking in on her riding Bambi's eager face. With Bambi still smothered under her ass and pussy Penny starts in on Sam, smacking his balls while berating him for daring to look at his ex-girlfriend getting fucked. Penny makes him stay to watch while the two girls get each other off and then makes him beg Bambi for a spanking! After the spanking Bambi and Penny both decide to give Sam a first hand lesson in how great their vibrator is at making people cum!         

In PART 1 and PART 2 Penny tries to help her buddy Sam get a date while also having a lot fun teasing and embarrassing him about the reason he can't get a girl in the first place. His cock is just so little! Penny can't help making fun of him, even though she does really want Sam find a girlfriend. She has finally set him up on a blind date with a cute girl who already knows his boner is itty bitty! Penny is helping him get ready when the girl texts to say she wants to see pictures of his undersized unit before the date. Must have had some second thoughts about willingly accepting a puny penis. Penny is definitely not going to waste this final opportunity to humiliate an extra small stiffy! Will he even make it out to the date or will it be another night of panty sniffs and pity wanks? 

Lily Lane has been humiliating her nerdy neighbors for a long time but now she is actually fucking one of them and cucking the other. Lily is having sex with cute little Juliette and using the key to her apartment to do wedgie sneak attacks on Sam the cuck. Lily is not just using her new found access to his home to give Sam the usual pantsing and wedgies but also got Juliette's permission to dress him up in her clothes whenever Lily feels like it. Sam is used to his hot neighbor bullying him into butt kisses and stripping him naked but now he gets to learn what it feels like to get bent over for wedgies in his best friend's dirty panties. On the brightside, sissifying him turns Lily on so much that Sam also gets to learn what it feels like when a hot girl cums right in his face.