Jessica loves to play control games with the horny men who want to fuck her. She has two young studs wanting to be her boyfriend, so she decides to play a game of chance. She flips a coin to decide who will be her boyfriend and who will be her bitch. The winner gets to fuck her, while the loser gets to be a sissy in a pink collar and a chastity belt! As the new sissy is doing his maid duties, Jessica gives him a new task – sucking on a cock. She even takes photos of the sissy’s humiliation as the cum explodes all over his face. She then puts the sissy cuck into use licking her feet while she makes out with her boyfriend, then has him clean her boyfriend’s ass as well, just for fun. Jessica then takes the bitch with her strapon, then makes the sissy suck on real cock as she rails his ass. Of course the sissy now has to clean his ass juices from her strapon. With her boyfriend gone, Jessica is so horny that she even allows her sissy bitch to eat her pussy. Jessica teases his locked up cock with the possibility of fucking her, but Jessica keeps his chastity cage locked on, making sure the bitch gets no pleasure at all from the fucking. When the boyfriend returns, Jessica makes the bitch perform for their amusement, walking all sexy in his heels as they laugh at him. Jessica completes the bitch’s cuckolding training by making him watch as she fucks her boyfriend, worshiping her feet while she gets fucked. She then orders the bitch to be their human lube, licking her pussy and her boyfriend’s cock as they fuck. After licking up the cum load the boyfriend shoots on Jessica’s stomach, she makes the bitch confess that he could never fuck her the way her boyfriend did. Jessica makes the bitch thank her boyfriend for fucking his new Mistress, then orders him to kiss the boyfriend’s cock as well. Jessica has won her game again, making yet another man a chastised cock sucking sissy bitch for her amusement.