Esmi, Tristen, and Melanie are having fun partying, but with parents coming home soon, they need somewhere else to go. They remember that the local nerd boy, Eugene, is home alone for the weekend. The cruel girls decide to have some fun at his expense; they are going to make him into a chastised sissy bitch for their amusement while they use his house as a place to party! Eugene is so happy that hot girls are actually coming to his house that he quickly agrees to everything they ask – especially when they start flashing their tits, asses, and pussies at him! He agrees to get naked for them, causing them to burst out in laughter at how small his dick is, especially when compared to a real cock! Because his cock is so small, they let Eugene know that the only way he can be around them is to have his sissy dick locked in a cage – while he is dressed like a sissy as well. Of course, the pathetic geek is all too eager to agree to anything for these hot girls. So happy to be around hot girls, Eugene quickly agrees to be dressed in a sissy maid’s outfit and locked in chastity, cleaning house as the girls play poker and drink. The girls have an interesting twist on playing poker; as Eugene soon finds out. After getting the strapon locked on his head, Eugene is told to face fuck the pussy of the winner of the hand. If that girl actually show in any way that she enjoys it, she has to drink! How pathetic it makes Eugene feel, that the girls don’t even want to admit accepting pleasure from a dildo he is wearing on his face! The girls decide to play another game with Eugene: having him smell and lick their dirty asses clean, then guess which girl’s ass he was licking! The girls laugh as they order Eugene to breath in their ass odor, then rub their asses all over his face. Of course, the nerd guesses wrong several times before finally identifying the correct girl. Eugene is all excited, wondering what his prize is for finally winning the game. Knowing what they have planned next for him, the girls just burst out in laughter. The girls decide to order some pizza, ordering Eugene to answer the door in his sissy maids outfit. The girls tell the pizza man they have no money for a tip, but would he like a blowjob instead? He quickly agrees, but then gets told it will be Eugene giving it! Eugene does not want to do it, but the girls tell him it is the only way they will let him out of chastity, so he reluctantly agrees. The girls just laugh as Eugene sucks the pizza man’s cock, giving him directions and even forcing his mouth wider to get more of the cock in. When the pizza man blows a huge load all over Eugene’s face, they laugh at his humiliation, then order him to clean up so that they can use him some more. They leave him alone and sobbing, cum dripping down his face.