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Description: Brianna wants to show her son how to pleasure a woman. It’s about time he finally learned. After today he will do this for his mother and sisters. Brianna’s son has already been locked into a very tight chastity cage. He won’t be pleasuring anyone with that little nub. Instead, Brianna straps a dildo into her son’s mouth. It will be one of her son’s responsibilities from now on to make mommy cum. Brianna’s son does not like the gag, but mother straps it on anyway. The dildo is a nice decent size, unlike Brianna’s sons locked-up little parts. Brianna’s going to be so proud of her son when he finally learns how to get a woman off. Brianna has her son lay flat on the bed and sits on his face while riding the dildo. Mommy climaxes on her son’s face while he remains locked in his little cock cage. Brianna then teaches her son another position. This position, the one with him kneeling at the foot of the bed, is the position his sister favors for her orgasms. Brianna enjoys a second climax in this position. Very satisfied with her son, he decides now is a good time to bring up some of his problems at school. Brianna’s son confides in her that one of the teachers does not approve of how he dresses. Brianna assures her son that she will go to the school and have a talk with his teacher about the feminine clothing she prefers her son to wear.

Description: Marcello is so happy that Raven allowed him to take her out on a date! Raven is less than thrilled. It wasn’t a great date. Her steak wasn’t cooked right, she had to send it back. It was just sort of meh. Raven is used to being wowed. While discussing the mediocrity of their recent dining experience, Raven notices Marcello looking at her feet. She pries a bit and discovers that her date has a foot fetish. It amuses Raven to have discovered this about Marcello. Marcello is excited that Raven seems interested in his foot fetish and offers to give Raven a foot rub. Raven takes the lead, though, and commands Marcello to get on his knees before allowing him to touch her feet. Once on his knees, Raven allows Marcello to smell and worship the stockings that she has been wearing all day and night. Raven admires Marcello’s penthouse while he indulges himself with her feet. Raven is curious what Marcello does for a living. Marcello responds that he doesn’t really work because he’s received a large inheritance. Raven knows almost instantly that she can financially drain this wealthy foot fetishist, take him for every penny. Raven is very dominant about exactly how she wants her date to worship her stockings and feet. Marcello asks Raven out on a second date. Raven responds that she’d love to go out again, but she wants to go shopping first so that she can have something new to wear for their second date. Marcello wants to make the beautiful Raven happy, so he agrees to buy her whatever she wants to wear. Raven gets really excited! Marcello is so easy to part with his money! She pulls him in closer and allows her date to worship her wet pussy after he has agreed to treat her to the spending spree she desires. After her orgasm, Raven wants to hear more about Marcello’s trust fund.

Description: The very sexy Princess Mia bounces her oiled ass on a slave boy’s face. She giggles and grinds while the slave boy is all locked up in chastity beneath her. Mia bounces harder and higher and the slave boy’s nose is thrust deeper into her bottom, where he cannot breathe. The boy’s face turns purple and Mia thinks that’s funny. She jiggles her bottom and presses down into him with her full weight. Mia grinds the slave boy’s face hard. He is just a toy for his Keyholder. Mia decides to put the boy to sleep. She wraps her thighs around his neck and squeezes him until he goes limp beneath her. Mia thinks it’s funny that she can overpower a boy with just the strength of her legs.

Description: Amber’s financial slave got her an all expense paid vacation to Las Vegas, just like she wanted. While Amber stays in a Palms penthouse suite, the slave stays in the Super 8 a few miles from the strip. Amber is mad that the slave spent money on a motel for itself. It should be sleeping in its car so that it has more money to give to Amber, and so that it can drive straight to her whenever she needs something. The slave agrees to do anything. It is just so desperate to be near its beautiful, young, Princess. It tries and tries to keep her happy, but all Princess Amber wants from the slave is more and more of his money.

The slave voices that its upset that Amber is going out with another guy in the evening. Amber just laughs at him. She explains that her date is very attractive. Her date doesn’t have a lot of money like the slave, but she has the slave to pay for things, so her date doesn’t really need to be well endowed in every way. Amber tells her slave to give her money so that she can go to a nice place on her date with the handsome man. Amber counts the funds she has just collected from her financial slave while it kisses her feet. She’s upset that the money isn’t enough, but the slave agrees to go get more cash.

While the slave is getting cash, Amber’s room service arrives. She wanted filet mignon as a snack, but the financial slave ordered it at the wrong temperature. Amber likes medium rare but got medium. Everyone knows that overcooking fillet mignon ruins it completely and make it totally inedible. Amber has had it. She decides to give the slave a strict caning before taking its cash and leaving to go out on her date. Amber angrily hits the slave with the cane several times on cold skin. It leaves deep red welts. The crying slave agrees to get Amber even more money to help calm her down.

Amber counts the additional money she has collected from her financial slave while admiring the freshly made cane marks on the slave’s ass. Satisfied with the damage she has done to his body and wallet, Amber contentedly leaves to enjoy her date with the handsome man.

Description: Raven Hart enjoys the view from her penthouse balcony while her cuckold husband kisses her ass. Her husband must follow his wife’s instructions exactly. If he is good, he might get to taste her pussy, which she almost never lets him do. Raven is teaching her cuckold husband to be a good listener. He must call her “Mistress” and obediently kiss her ass before he gets to lick it. Raven lets her husband smell the pussy that he never gets to fuck. His wife keeps him locked up nice and tight in chastity, so he knows that he will never get to fuck her the way she lets other men fuck her. Raven’s husband is grateful just to be able to smell where the other men fuck her. She lets her obedient husband lick her pussy, just three times. That’s all he gets for today. Raven goes back to enjoying the view. She has complete control over him with the pussy that he will never get.

Description: Chloe and Sasha make a loser crawl back and forth on the deck kissing their toes in flip flops and sandals. The loser is naked and locked in chastity. He must crawl to whichever girl calls him and do what she says. The girls pass the loser back and forth between them, getting their feet licked. They remind the loser that it is pathetic. The girls get tired of standing. They sit in lawn chairs and make the loser take off their sandals. They verbally humiliate him while he worships their feet. They want to take the humiliation even further. The girls decide to go inside to find something to sodomize the loser with. He has never gotten fucked before and is very scared. The girls send him away to get the big tub of Vaseline as they conspire and giggle.

Description: Bratty besties, Anabelle Pync and Dakota Charms, have been exploiting a loser they found on their Vegas vacation named Stanley. Stanly is a pushover and will do anything for the two pretty girls he was fortunate enough to meet. The girls have known Stanley now for a couple days, and they decide that its time for him to go into chastity and be collared. Stanley has no idea what any of this chastity or collaring business means. The besties make Stanley strip out of his preppy khakis. He won’t need clothes in his new life as their collared slave.

Once Stanly is naked the girlfriends make fun of Stanley’s small penis. Pretty girls are not used to seeing penis’ as small as Stanley’s. It’s a real oddity to them. After marveling at Stanley’s small penis for a while, the girls lock it up. They are very excited to own a slave together. The girls are best friends and they share everything. Their new male slave will just be another thing that the girls share.

Anabelle and Dakota send Stanley into the bathroom to figure out how to put the chastity device on. Once Stanley has figured out how to wear the chastity device, they will collect both the master and spare keys. Each best friend will wear a key around her neck! One girl gets the master and the other gets the spare!

Stanley emerges from the bathroom with the chastity device on. The girls close the lock. Then, they make Stanley kneel and put a collar around his neck. Stanley is now officially their slave! Even locked up, Stanley’s anatomy is disgusting to the girls.

They want to try out his foot worship skills. Anabelle and Dakota tell Stanley to lick their toes. Stanley is very humiliated to be licking the girls’ feet. He doesn’t even know how he got here. Anabelle makes Stanly gag on her foot while she and Dakota laugh. They inform Stanley that he will no longer have access to his own penis, ever.

Now that Stanley is their slave, the girls get meaner and meaner to him. He is no longer even a loser in khakis. He has become nothing but an object for their use. The girls tease Stanley’s chastity to remind him of what he will never have in his new life as a slave to two bratty best friends.

Description: Carmella wants to play an edging game with her slave. He may even get the opportunity to cum. The slave is so excited! He hasn’t been out of chastity in nearly a year and has almost completely forgotten how to masturbate. Carmella reveals that she has only allowed the slave out of chastity because she wants it to learn to be her toilet. It’s going to have to learn to lay on the floor and drink all of Carmella’s and her girlfriend’s pee. Carmella slaps and spits on her filthy slave. It truly disgusts her. Serving as a human toilet is perfect for a slave that is so naturally revolting to women. Carmella puts a funnel into her slave’s mouth and spits in it. The funnel is going to stay in the slave’s mouth when she and all her friends use it as their human toilet. Carmella does not allow her slave to cum. She locks it back up in chastity and leaves it on the bathroom floor with the funnel in its mouth.

Description: Three cruel girls, one old loser. Can he survive being smothered by the trio of big, perfect booties? It might just be too much ass! The girls take turns smothering and riding him. They want to control his breath completely. Losers shouldn’t think for themselves, let alone breathe. They should be told when to do that, too. The old loser’s face turns purple and blue. He will never even get to touch the ass that’s controlling his life. The girls all take off their leggings so that they can face sit him in their thongs. They take turns bouncing their bare cheeks on his loser face. What a tease! The loser must admit that he could never date or fuck a girl like the hot trio riding his face. The girls get very excited watching the loser’s veins start to pop out of his bald head from lack of oxygen. They giggle gleefully while he suffers.

Description: Kimber wants to win a strap-on contest at her sorority and she’s enlisted her mom, Raven, to help. Kimber’s mom won the strap-on contest two years in a row back in her sorority days. And she still regularly ass fucks her husband, Marcello. Raven invites her daughter to practice for the contest on her step-father. The mother and daughter each grab a hole and start to fuck Marcello. He’s used to getting ass fucked by his wife but having his step-daughter join in is too much to handle! Marcello tolerates the indignity, even when his step-daughter straps on the largest rubber cock in the family’s collection. He begs his step-daughter not to put the huge dildo in his ass, but Kimber is set on winning the sorority contest. She knows that having the biggest rubber cock will really set her apart. Raven passes her husband off to her daughter. She makes Marcello clean her dildo with his mouth after it has been in his ass. Kimber is so happy as she pushes the enormous dildo into her step-father. With a feat like this, she’s a shoe-in for the winner! A look of pure anguish registers on Marcello’s face and the mother-daughter strap-on team just laughs! The women giggle and play pattycake as they violate two of Marcello’s holes. Raven dangles her husband’s chastity key in his face while his step-daughter takes him from behind. When Kimber is done fucking her step-dad, she spits in his face and leaves him tied up. She and mom are going to take his credit cards and go shopping. When they get back they might practice some more for the contest.

Description: Veronica hates her step-dad so much but can manipulate him because she is a 19-year-old cheerleader and he is a pervert. Every once in awhile the old fart gets out of line and tries to act like a real dad to Veronica and lay down the law. But he’s isn’t Veronica’s real dad and she knows that she doesn’t have to listen to him. Veronica’s step-dad asked her to please stop smoking in the garage. Veronica will do as she pleases, and in fact, she will use her perverted step-father’s mouth as her ashtray. Veronica puts her cigarette out on her stepdad's tongue. She makes him swallow the butt and all the ashes for her so that mom won’t find out she’s been smoking in the garage, again. Her step-dad is such a pushover. He does exactly as his 19-year-old step-daughter commands.