Throughout the night, Kimber Woods and Cheyenne Jewel have been playing strip poker with Aiden Starr. Both Kimber and Cheyenne sit there fully nude having lost their last article of clothing and Cheyenne wants to play just one more hand. Aiden is mildly amused with the hubris of her two naked playmates. She is willing to play one more hand, but the completely naked girls are going to have to come up with something to bet. Kimber has the brilliant idea to wager their assholes. The cards are dealt and Aiden tells the girls to show their hand. Aiden wins and is determined to show these two little losers what it means to give up their asses. Aiden bends the girls over and brutally spanks their asses until they are bright red. She pops toys in and out of their holes, making them gape wide open. The girls lick and suck each other's assholes and the toys that come in and out of them. Aiden ramps up the energy with some heavier anal play. She puts the entire two foot long slink all the way into Cheyenne's asshole. She pushes it in and pulls it out, making Kimber lick and gag on the long toy that was buried deep inside Cheyenne's ass. Kimber's asshole gets stretched wide open with the metal speculum. We see deep into her asshole, getting a glimpse of her pink asshole walls. Cheyenne gets throat fucked by Aiden's fists which makes Cheyenne drool puddles of spit down into Kimber's pried open asshole. Aiden really wants the girls to ante up more so she lays them down and ass fists both the girls hole's until they beg for mercy. Both girls have explosive anal orgasms. Cheyenne's asshole is punished the most for her being a horrible card player. Cheyenne is bent over and strap on fucked in the asshole right over Kimber's pretty face. Kimber waits with her tongue out to suck the cock right when it comes out of Cheyenne's ass. Cheyenne get's pounded good and hard until her asshole is dripping with her own anal cum and Kimber licks it all up.

Marica Hase does as she's told and Dana DeArmond commands her to fist her ass. Dana gets her ass in the air and Marica gets to it and digs two fingers from each hand into Dana's beautiful ass and spreads her hole like a speculum. She tongue fucks Dana's ass and Dana grabs Marica's hand and jams it in there. Dana uses Marica's hand like a dildo and fucks herself with it until she cums hard with an Hitachi pressed up against her clit. In the next scene Tori Avano is next up to take a fist from Dee Williams. Dee slips in a few fingers at first and when she's knuckle deep inside Tori's asshole, Tori says she cant take any more. Tori regains composure and tells Dee to send it and soon Dee is wrist deep inside and Tori's asshole cums hard. Dee moves over to Syren De Mer and slides her whole fist inside her ass and licks Syren's pussy while she fist fucks her stretched asshole. In the next scene we have the legendary anal queen Casey Calvert completely naked on her back with her legs spread. Jenna Sativa kneels down next to her and lubes up her hand. She slowly slides it inside Casey's ass and Casey cums hard with Jenna's whole fist inside. Next up is the cute and sexy Alexa Nova who gets fisted in her yoga studio by London River. Alexa returns the favor and gets London face down and ass up. Alexa stretches London out with her fist and even gets eight fingers inside. Then Anna De Ville fists her own ass at the request of her Dom, London river who then gets her own ass fisted by Anna. For the grande finale we have Aiden Starr who has on the backs, Cheyenne Jewel and Kimberly Woods. Their legs are spread and Aiden puts a fist in each of their asses and has them both screaming, laughing and cumming from getting their asses fisted.

Kimber is upset because her boyfriend bailed on her. Since she’s horny, she decides to sexually use her step-dad, Marcello. Kimber is a bratty terror of a step-daughter, and she’s even worse when she’s sexually frustrated. Terrified of both his step-daughter and wife, Marcello agrees to orally pleasure Kimber. Kimber is moody and yells at her step-dad while he is doing his best to help her climax. As she nears her orgasm, Kimber squeals a bit and seems relieved. Marcello’s chastity jingles as he services his step-daughter’s pussy. It’s very exhausting for Marcello to constantly be expected to perform oral servitude for both his insatiable wife and his nineteen-year-old step-daughter. Kimber, of course, does not care. She eventually has an orgasm while using Marcello’s tongue, but her sour, bratty, mood doesn’t budge. After Kimber cums on her stepdad's face, she abruptly sends him away.

Kimber is training her slave for a strap-on contest at her sorority. This year she’s determined to win! She’s knows that she’s going to be up against some highly competitive girls whose slaves can take some really big cocks. To make sure that she wins, Kimber is training her slave with the biggest dildo she can find. It’s almost as thick as her arm! Kimber wants to make sure that her slave’s ass can get drilled with her enormous strap-on in every position. First, the slave must wet the giant cock and get it as deep as possible down its throat. After some throat fucking, Kimber throws the slave directly into piledriver. With the slave’s legs over it’s head, Kimber is able to drive the big cock deep. When Kimber tires of this position, she takes the slave’s ass doggystyle. The slave’s chastity cage bounces as Kimber reams it’s ass from behind. Kimber takes a little respite to make the slave do ass to mouth. Then she goes right back in. Kimber spits in her slave’s face. She pulls on the slave’s collar to the point where he almost goes out, but not quite. Kimber throws her slave into the last position that she wants to practice. She turns him around into missionary to ensure that she can get a tight grip on his chastity cage while fucking his ass. Kimber’s got her slave right by the balls while she fucks his asshole deep. She works the whole entire enormous dildo deep into her slave while gripping the chastity firmly. When she’s finished, Kimber has the slave lick the cock clean for her. Kimber is excited because her slave did so good taking it for her! It excelled with the biggest cock in every position! She’s a shoe-in for the win at the sorority this year!

Raven never wanted Marcello. She always wanted to have two daughters. Instead of a second daughter, Marcello came into her life. That’s ok. Raven will turn Marcello into the girl she’s always wanted. Thankfully, Raven has the help of her daughter, Kimber. Kimber has always wanted a sister. She’s happy to help her mom make Marcello into the sister she never had. Marcello’s gender re-training will start now. Kimber and Raven have already locked Marcello into a pink chastity.The mother and daughter are ready to help prepare Marcello for his new life as a girl. To continue his training, he will be shipped away to Raven’s sister’s house. Raven’s sister runs a home for sissies, where to earn their keep they are whored out on dates. In preparation, generously, Kimber and Raven are going to help Marcello learn how to take very big cocks. Because Marcello does not have the proper number of fuck holes for a girl, they will have to train her ass to function for men like a cunt.First, the mother and daughter play dress up with Marcello, who will now be referred to as “Marcy.” Kimber is very excited to share her clothes with her new sister, Marcy. Kimber’s clothes are very provocative, but Kimber tells Marcy that men like provocative clothing on girls. In his new role as a sissy slut, his function will be to please men and do things that they like. Learning to wear revealing clothing for men is just a start.Kimber and Raven are really pleased with Marcy’s transformation. They’ve spent enough time on Marcy’s new look, now, it’s time to train her to get fucked like a girl. Kimber and Raven spit-roast Marcy. She must learn how to suck cock while getting fucked from behind. This kind of sexual multitasking is foundational for a slut’s training. Raven begins the ass fucking with a large dildo.Marcy’s new sister has an extra-large sized dildo, even bigger than her mom’s! Kimber thrusts the enormous dildo deep into her sister’s “pussy.” Marcy cries out. It’s too big! But Kimber and Raven insist that Marcy must learn to take it. She will thank them for the good solid training once she is earning her keep as a whore. Good whores do as they’re told. Marcy must learn to be a good whore. With Marcy flat on her back, Kimber fucks her ass while Raven fucks her throat. Her pink chastity is in full view. Marcy is well on her way to becoming an excellent sissy slut.

Raven never wanted Marcello. She always wanted to have two daughters. Instead of a second daughter, Marcello came into her life. That’s ok. Raven will turn Marcello into the girl she’s always wanted. Thankfully, Raven has the help of her daughter, Kimber. Kimber has always wanted a sister. She’s happy to help her mom make Marcello into the sister she never had. Marcello’s gender re-training will start now. Kimber and Raven have already locked Marcello into a pink chastity.The mother and daughter are ready to help prepare Marcello for his new life as a girl. To continue his training, he will be shipped away to Raven’s sister’s house. Raven’s sister runs a home for sissies, where to earn their keep they are whored out on dates. In preparation, generously, Kimber and Raven are going to help Marcello learn how to take very big cocks. Because Marcello does not have the proper number of fuck holes for a girl, they will have to train her ass to function for men like a cunt.First, the mother and daughter play dress up with Marcello, who will now be referred to as “Marcy.” Kimber is very excited to share her clothes with her new sister, Marcy. Kimber’s clothes are very provocative, but Kimber tells Marcy that men like provocative clothing on girls. In his new role as a sissy slut, his function will be to please men and do things that they like. Learning to wear revealing clothing for men is just a start.Kimber and Raven are really pleased with Marcy’s transformation. They’ve spent enough time on Marcy’s new look, now, it’s time to train her to get fucked like a girl. Kimber and Raven spit-roast Marcy. She must learn how to suck cock while getting fucked from behind. This kind of sexual multitasking is foundational for a slut’s training. Raven begins the ass fucking with a large dildo.Marcy’s new sister has an extra-large sized dildo, even bigger than her mom’s! Kimber thrusts the enormous dildo deep into her sister’s “pussy.” Marcy cries out. It’s too big! But Kimber and Raven insist that Marcy must learn to take it. She will thank them for the good solid training once she is earning her keep as a whore. Good whores do as they’re told. Marcy must learn to be a good whore. With Marcy flat on her back, Kimber fucks her ass while Raven fucks her throat. Her pink chastity is in full view. Marcy is well on her way to becoming an excellent sissy slut.

Kimber sits on her slave’s face, pressing its nose deep into her ass. She loves controlling the slave’s breath with her body. Kimber rocks and bounces her cute bubble butt while sitting on her slave’s face. She presses her pussy right up against its nose. She doesn’t want to hear any breathing! Kimber decides to scissor her slave’s neck between her thighs. The slave suffers greatly, chocking, crying out, eventually going limp. The slave is on the brink of losing consciousness, face turning purple, but still, Kimber wants him to suffer more. Kimber climbs on top of the barely alert slave and rides his face while he fades in and out.

Kimber’s mom is out on a date. While mom is out, Kimber wants her step-dad to worship her ass. Kimber goes on social media to see how her mom’s date is going while her step-father licks her ass. She ignores her step-father unless he does something wrong, then she yells at him. Kimber reports to her step-father that her mom seems to be having a really great time on her date and uses her step-dad’s tongue until she gets bored. Kimber wants to play dress up while mom is away and make her step-father into a sissy girl. Her step-father is only there to play with and please her.

Throughout the night, Kimber Woods and Cheyenne Jewel have been playing strip poker with Aiden Starr. Both Kimber and Cheyenne sit there fully nude having lost their last article of clothing and Cheyenne wants to play just one more hand. Aiden is mildly amused with the hubris of her two naked playmates. She is willing to play one more hand, but the completely naked girls are going to have to come up with something to bet. Kimber has the brilliant idea to wager their assholes. The cards are dealt and Aiden tells the girls to show their hand. Aiden wins and is determined to show these two little losers what it means to give up their asses. Aiden bends the girls over and brutally spanks their asses until they are bright red. She pops toys in and out of their holes, making them gape wide open. The girls lick and suck each other's assholes and the toys that come in and out of them. Aiden ramps up the energy with some heavier anal play. She puts the entire two foot long slink all the way into Cheyenne's asshole. She pushes it in and pulls it out, making Kimber lick and gag on the long toy that was buried deep inside Cheyenne's ass. Kimber's asshole gets stretched wide open with the metal speculum. We see deep into her asshole, getting a glimpse of her pink asshole walls. Cheyenne gets throat fucked by Aiden's fists which makes Cheyenne drool puddles of spit down into Kimber's pried open asshole. Aiden really wants the girls to ante up more so she lays them down and ass fists both the girls hole's until they beg for mercy. Both girls have explosive anal orgasms. Cheyenne's asshole is punished the most for her being a horrible card player. Cheyenne is bent over and strap on fucked in the asshole right over Kimber's pretty face. Kimber waits with her tongue out to suck the cock right when it comes out of Cheyenne's ass. Cheyenne get's pounded good and hard until her asshole is dripping with her own anal cum and Kimber licks it all up.