Mistresses January and Esmi decide to play a cruel game with their helpless slave bitch. Knowing that he is terrified of the cane, they decide to whip him instead, promising only to stop when he sincerely begs to be caned! The bitch is soon begging to be caned, but the Mistresses continue the whipping until they are convinced he is sincere. Things go from bad to worse as the Mistresses cane the bitch; he is soon screaming and shaking helplessly in his chains, much to the delight of the heartless Mistresses. When they have finished with the bitch, they are so hot from his punishment that they make out, leaving him still bound with a cane in his mouth, waiting for further punishment
"We need some entertainment" Goddess Kendra says. Goddess Brianna calls over the bitch boy from the corner and they decide they will be very entertained hooking him up to the fucking machine and stretching both of his holes. They shove their fingers in his mouth and see how much it will stretch. "You´re holes belong to us, bitch!" Kendra says. "Let´s break him in!" says Goddess Brianna. The bossy and demanding women hook him up to the fucking machine and stretch his pathetic mouth and pussy for them.
Goddess Nadia White and Goddess Nyssa Nevers punish their thoughtless slave who thought it was a good idea to bring them chocolates and roses for Valentine´s Day. Goddess Nadia and Goddess Nyssa mock his attempt to get them gifts, as if he knew what could possibly make his Goddesses happy. Instead of wanting bullshit gifts, Goddess Nadia and Goddess Nyssa want a slave who knows how to take a cock like a good whore. Goddess Nadia forces the worthless slave to slobber all over Goddess Nyssa´s big black dick before stuffing his mouth with her own strap on down his throat. The Goddesses take turns fucking their slave´s mouth until their cocks are wet with his spit. That´s when they bend him over and start pegging his tight man-pussy. Goddess Nadia shoves her cock up his slut hole while pulling him back by his harness so he is forced to take the whole cock up his chute. After Goddess Nyssa makes him hold a ridiculous rose in his mouth, she takes up position the slave so she can DP his ass with Goddess Nadia. When Goddess Nadia and Goddess Nyssa have their fill of their slave, they leave him a mess on the floor with one rose sticking out of his ass, hoping he will grow a rose bush in his worthless hole.
Domina Helena grabs her slave by the head and forces him to lube up her black strap on cock with his spit. Domina Helena then pushes her hands into his man pussy to prepare it so she can fuck her slutty slave. She then slides her big cock deep into her slave´s man pussy and begins pegging her useless slave.
Jade and Nikki have very high expectations for their live in sissy maids. The girls conduct their weekly sissy maid inspection to ensure the sissy slaves are up to their standards. Sissies line up so the girls can inspect their chastity devices; a proper sissy maid always has their little cock pellet locked away. Danielle is first up for pussy inspection.Jade asks, "Are you tight for me today?? Or loosey goosey?? Have you been dildoing your ass-pussy?"Jade gives Danielle´s ass-pussy a fingerbang inspection, revealing that Sissy Danielle´s slut hole is definitely loosey goosey!! Danielle Sucks on Nikki´s strap on while Jade takes a to her ass. Danielle yelps in excitement from having her pussy pounded so hard. Jade gets so excited while spinning that huge cock inside sissy Danielle´s pussy-ass. Nikki keeps Danielle quiet by pushing cock down her throat.Next up for inspection is Sissy Maid Sasha. Jade cuts open Sasha´s pantyhose, exposing her plump little ass just ready for fucking. Sasha´s ass-pussy is much tighter. Jade warms Sasha up with some finger fucking. Next Nikki straps on a head harness dildo onto Slutty Danielle.While stroking Sissy Danielle´s head harness dildo, Jade asks, "Do you know how to use a cock properly? Do you want to show me how you use a cock?"Sissy Danielle is made to fuck Sissy Sasha´s ass with the head harness dildo. How humiliating and hot! Jade instructs Danielle on how she wants Sasha fucked. While Sasha is getting ass fucked, Jade teases Sasha with her panties. "Your sissy dick is locked away, and you will never have my pussy. Next the sissy maids are made to kneel facing each other. The girls make the sissy slaves fondle one another and kiss. Jade eggs them on to make out passionately. When Jade is satisfied with enough amusement from her sissies, she orders them to go clean their whored out selves up!
Mistress Raven has some very cruel plans for her wimpy slave, and she is eager to put them into action. Her slave has learned through hard service to fear her, and for good reason as he will again find out. The heartless Raven has no mercy for the terrified slave and beats him sadistically with a metal crop as he wails in pain. This is just the beginning of his torment as she moves on to violating his asshole with a brutally large black cock. His pained moans and desperate whimpering are music to her ears as she relentlessly rams the huge phallus into his tight hole. Her twisted imagination is as boundless as her cruelty, and she laughs at his pain and degradation. Mistress Raven has no compassion for her slave, fucking him mercilessly well past his breaking point.
It is the countdown to the New Year and the women are pissed! They are dedicating the new year to abusing and enslaving all men! They start by strapping down this hoe to to the saw horse and giving him a fierce spit roasting with huge strap-on´s. New Years wouldn´t be complete with out a toast!. The bitch boy uses the face gag dildo to please Ms Yasmin, She drenches him with her squirt! The ladies have a sparkling toast then the make the slave drink from his asshole. They shove the bottle straight up his ass!
Mistress Adriana is not satisfied with just fucking her slave in the ass; she wants him to beg for it and totally submit to every thrust of her cock into his ass. Adriana starts by making him suck on her cock, laughing as it bulges out the side of his mouth. She then mounts him with her cock and fucks him long and hard. Adriana then puts him on his back and continues the fucking, smacking his cock and balls as she takes his ass. After Adriana is finished with her slut´s ass, it is open and gaping, ready for the huge butt plug Adriana shoves into it as her slave gasps out in pain.
Mistress Summer has had her boy toy slave locked in chastity for a long time and knows he is desperate to be released. She just might relent and unlock him, but only if he proves himself to her satisfaction first. It won´t be easy as she intends to put him through a long strapon ordeal with her huge cock. He needs to take it properly and without complaint or he can forget his reward. For her it is fun plowing his ass deeply and hearing him moan. For him it seems endless and he tries his best to take it well for his mistress. Mistress summer loves to see him wince and squirm as she rams the dick deep in his"pussy" as it demonstrates her total dominance and superiority over her slave. The slave is suffering well for her, but will it be enough to earn his chastity release?