Biggest Challenge

Biggest Challenge

Biggest Challenge Cheyenne is as tough as she is hot. She loves a good challenge, so The Pope starts this eager beaver with a brutal predicament stress position. Next a nasty crotch rope that destroys her pussy before a vibe is added to devastate her sore cunt. Her back side is the next target. Her amazing ass ad muscular back are begging for torment. She is flogged, spanked, caned, and tormented just to fill the room with her screams of suffering. Now she finds herself helpless in a side suspension that has her wrapped up like a nice present. Her feet get the full treatment of bastinado, before her holes get filled and fucked. Finally Cheyenne is spread wide against the wall. Her nipples are tied to her toes and weights are added to ensure her suffering. Her feet are caned and then hot wax is dripped all over her legs and feet. Her final orgasms are as painful as the rest of her day


Download Video

Video

Wrestlers get Bribed with Anal Pain to throw the Match of

Wrestlers get Bribed with Anal Pain to throw the Match of Jenevieve Hex and Amber Ivy are practicing for the Big Tag Team Wrestling show happening on Friday night. Their Coach, Cheyenne Jewel, is showing them how to pin their opponents, trap them and fuck them op. Savannah Fox barges in on their training and lets the group of big ass girls in on a deal. Savannah tells the girls that shes going to bet Big on the OTHER team to win and Jenevieve and Amber need to throw the match so that everyone can walk about with a lot of cash. Jenevieve isnt into the game. Shes been training really hard and she doesnt think her sponsors will be happy if she loses. Shes confident that She an Amber are going to win. Cheyenne and Savannah have an interesting way into coax the girls into throwing the match. The bend them over and spank them, Rub their tushys, ram toys in and out of their assholes until they gape, make each other clean up the ass toys with juicy Ass to Mouth. Then they strap on fuck each girl until their muscles are so worn out they cant possibly recover by Next Friday. Being a wonderful coach, Cheyenne Jewel shows the girls how to take REAL anal. Cheyenne Jewel gets her asshole fisted. Then she take the entire 2foot long Slink into her asshole, Nice and deep. Amber Ivy licks up the slink after it comes out of Cheyennes Asshole

Velvet Gloves, A Fisting Compilation
video

Velvet Gloves, A Fisting Compilation

Velvet Gloves, A Fisting Compilation Marica Hase does as shes 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 Danas beautiful ass and spreads her hole like a speculum. She tongue fucks Danas ass and Dana grabs Maricas hand and jams it in there. Dana uses Maricas 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 shes knuckle deep inside Toris 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 Toris asshole cums hard. Dee moves over to Syren De Mer and slides her whole fist inside her ass and licks Syrens 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 Caseys ass and Casey cums hard with Jennas 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

Six Slaves
video

Six Slaves

Six Slaves The Upper Floor throws a party to welcome the largest congregation of slaves and trainees it has ever had under one roof. Six girl zippers, nipple stretchers, ass hooks, and girl on girl on the floor is just the beginning of the fun

Pussy Burn
video

Pussy Burn

Pussy Burn Cheyenne is a famous, bigtime bondage model and MaX has hired her to make a film. He explains his concept to her she will be suspended, spread eagle, from the ceiling and MaX will light a fire underneath her, burning her pussy. Being the pro that she is, she seems fine with the scene. When the filming actually begins, however, Max finds her acting to be subpar. He wants his audience to be able to taste her fear, feel that pain that she should be feeling. Finally, he has had enough and decides to give her some proper motivation. With a propane tank, he starts a real fire underneath her. Cheyenne screams in pain and struggles with her bonds, as the flesh on the inside of her legs, and even her tender pussy, begins to char and blister. On and on it goes, her voice growing hoarse from her shrieks, smoke coming off her as the room fills with the smell of roasting flesh. Satisfied with his work, MaX prepares for his big finale. Pulling out a gun, he shoots her in the head, leaving her lifeless and bleeding body to hang from the chains that suspend her

TSAnal immigration Brutality
video

TSAnal immigration Brutality

TSAnal immigration Brutality Cheyenne Jewel and Charlotte Cross get stuck at the airport after an executive order comes through from the president to stop anyone who doesnt hold a US passport. Casey Calvert takes her job very seriously. She detains the two sluts in a back room. Charlotte and Cheyenne must sniff and lick each others gaping assholes. Cheyenne takes the entire slink deep into her asshole. Charlotte is tied up and fucked until her asshole gapes wide open

Bachelorette Party Debauchery.
video

Bachelorette Party Debauchery.

Bachelorette Party Debauchery. Casey Calvert is tying the knot and has a lot of kinks she wants to get out of her system. She makes her friends play a dirty version of truth or dare. She gets the girls to star sniffing each others assholes and then they give each other rim jobs. Casey can be very persuasive and eventually she gets a fist in Cheyenne Jewels ass and fucks both girls with a huge Strap on. This is Cheyenne Jewels giant Anal Debu

Cheyenne Jewel vs Chad Diamond
video

Cheyenne Jewel vs Chad Diamond

Cheyenne Jewel vs Chad Diamond Chad Diamond has been taking some Jiu Jitsu Classes lately and hes confident hes going to be able to get Cheyenne to tap to some of his sneaky moves. Cheyenne Jewel has been wrangling bitches for nearly a decade and she is confident that her rock hard solid muscles and years of experience are going to get her the W. The match displays some brutal submissions which means there are a LOT of penalties. One of these wrestlers is used really badly and is utterly humiliated. The Loser is given orgams denial, used for the winners pleasure and the lift and carried off the mats like the little useless slut they are

Strip Poker Three Anal Whores Go All In
video

Strip Poker Three Anal Whores Go All In

Strip Poker Three Anal Whores Go All In 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 others 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 Cheyennes asshole. She pushes it in and pulls it out, making Kimber lick and gag on the long toy that was buried deep inside Cheyennes ass. Kimbers 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 Aidens fists which makes Cheyenne drool puddles of spit down into Kimbers pried open asshole. Aiden really wants the girls to ante up more so she lays them down and ass fists both the girls holes until they beg for mercy. Both girls have explosive anal orgasms. Cheyennes 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 Kimbers pretty face. Kimber waits with her tongue out to suck the cock right when it comes out of Cheyennes ass. Cheyenne gets pounded good and hard until her asshole is dripping with her own anal cum and Kimber licks it all up

Bondage Jewel
video

Bondage Jewel

Bondage Jewel Cheyenne struggles. Her bondage lets her roll over, but nothing else. The red tape gag mutes her struggles to a dull frustrated moan. As she struggles her short skirt rides up revealing her plump ass. Hes seen enough and he has to get some. Ravenous for her he licks, sucks, and bites her feet. He even mounts her as she fights and screams, but hes not going to let her go before hes satisfied. With each position he gets more and more use out of her. He makes her put her mouth on his cock. He puts it in her cunt and finally her asshole. With each torment he gets harder until finally he explodes on her face.