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Charlotte Sartre is a very disobedient inmate at the all women's prison. She's been keistering anal toys and copulating with the other female prisoners. The Butthole Prison has brought attention to the Warden on this issue. Anal Warden, Dee Williams is a no nonsense busty MILF who has been known for doing extraordinarily cruel and unusual things to her female inmates. Charlotte denies she's done anything wrong and seems to think she can prove her innocence by NOT being able to fit any toys into her "tight ass". If the anal toys don't fit, you must acquit. Unfortunately for anal hungry Charlotte, try as hard as she can to keep her asshole tight, it just wants to stay open and suck up everything in its path. You could drive a truck through Charlotte's loose butthole. Dee starts with a nice firm over the knee spanking. Charlotte's tushy turns bright red and she writhes with pain and pleasure. The spanking isn't enough punishment, so Dee starts fingering and plugging Charlotte's asshole with toys. Charlotte's ass starts gaping wide open and Dee knows right away that she has caught her Anal Toy Smuggler and needs to administer a full anal examination. Dee then has to check the entire asshole so she performs a body cavity search putting her entire fist into Charlotte's ass. Determined to understand how Charlottes has been getting all these toys past the prison inspections, Dee has Charlotte demonstrate how she was able to stretch her ass out for keistering. Charlotte puts a giant red butt plug in Dee's asshole so that Dee can see how easy it is to hide things in buttholes. After learning how Charlotte is doing her bad deeds, Dee must perform one last punishment, She straps on a huge anal dildo and strap on fucks her poor, powerless inmate, leaving her asshole gaping wide open.
4 years ago
924
4:00
Meditating in her studio, Leya Falcon is a natural holistic reiki healer with long blonde hair, big tits, and a beautiful big ass. Today, London River enters Leya's reiki studio to help channel some good energy. After a reiki session, Leya learns that London's butthole chakra is out of alignment and preventing her from achieving true happiness. Leya has London lay down so she can adjust her butthole chakra back into alignment. She proceeds to stuff a huge butt plug in and out of London's ass. She pulls it out and looks inside and checks to see if the chakra has aligned, alas it has not so she must stretch her hole even more and moves on to larger toys to get the job done. London goes deeper and harder into London's asshole. She eventually gets her entire fist into London's asshole and punches her chakras back into place. Leya needs to get deeper however. She grabs the worm toy and snakes it deep into London's asshole. Leya then has London use a toy on her own asshole and has her lick all the butt juices off of it to get a taste of what a true butt-hole chakra alignment should taste like. London then puts a big black toy thats larger than her head into Leya's perfectly aligned asshole. The two must connect on a deep level so Leya gets tied up with rope to show how free she is spiritually. She could be bound physically and still feel freedom while her asshole gets foot-fucked, licked and sniffed. To finish off this hole-istic session, Leya Falcon gets a strap-on and fucks London's butthole hard, fast, and deep until it's gaped open, ready to accept the good wholesome energy flow that Leya has channeled into the room.
4 years ago
462
4:00
Lauren Phillips sweeps into her new McMansion with her giant suitcase and her hourglass figure, ready to charm her new step-daughter with a day out on the town. But her petulant teenage charge, Maya Kendrick, has already worked her way through seven step-mothers. She's also already fought her step-brother Seth over who will have to deal with Mommy number 8, her or him. Maya and Seth are a twisted duo that spend their time playing power games and fucking when their parents aren't looking. Maya has just had her ass beaten red and fucked on the living room couch in belt bondage when Lauren shows up for some wholesome family fun. The way Maya's eyes roll back in her head as she slobbers and moans with Seth's cock in her mouth make the whole premise of a chore trade seem a farce. Maya screams and begs as her nipple clamps are pulled on her tiny little tits and she is flogged, but it's only to beg for his cock in her slutty pussy and ass. Maya is surprised when she gives Lauren lip and Lauren changes tack, grabbing Maya by the ear and locking her in her room. Satisfied by her take-charge attitude, Lauren gets cocky when the maintenance man comes by. She invites him in for some afternoon delight, only to find him filming her while she's giving him a blowjob. Upon demanding he erase the video, Seth introduces himself as her new step-son and the fun really begins! Locking Lauren's arms behind her back in metal handcuffs, Seth flogs her huge tits, degrades her with her new name "8" written on her chest with lipstick, and electrifies her, then makes her squeal like a little piggy and crawl around the living room. Releasing his little sis and outfitting her with a huge strap-on, the two siblings take Lauren down with a double fucking, each taking turns with her ass and mouth while they continue with a litany of humiliation and corporal. Lauren is placed in a pile driver with clamps all over her tits, with cuffs locking her in place. A dildo is placed in her mouth for her to hold while Maya uses it to get herself off, and Seth fucks his new Mommy's ass. Lauren squeals and begs to cum, but to no avail, the twin sadists just continue to enjoy her body until they decide it's time to cane her stretched-out calves. Lauren can only watch helplessly and her sore muscles have 8 red stripes placed upon them with a heavy bamboo cane. Tied on her stomach and ball-gagged, Lauren serves as fuck furniture, getting railed in the ass and pussy until Maya wants to have another orgasm and her brother switches to her holes. She teases and spits on Lauren until she reaches climax and her pretty eyes roll back in her head. Having been properly trained in her maternal duties, Lauren is released and allowed to service her step-daughters clit. Seth fucks Maya and steps on her vibrator mercilessly until Maya begins to wonder if her orgasms are punishment or reward. Both new mother and daughter team look perfect on their backs, taking a hot load of cum together. Perfect bonding day!
4 years ago
31274
4:00
Penny starts her day perched atop a custom device that was built to ensure she is helpless. Her legs and arms are spread out and all of her weight is resting on her pussy. The Pope enters and brings with him a dental device that will hold Penny's lips apart, which will impair her ability to speak. The humiliation starts as soon as it is applied to her face. She tries her best, but she cannot help but laugh at herself because of the way she speaks with it in her mouth. Penny's flesh falls under a full assault from a heavy leather flogger. Her tits, her ass, and everything else that he can reach is turned a bright red as the flogger flies through the air. Clothespins are applied to all of the sensitive areas as Penny helplessly watches. The orgasm reward starts and the humiliation ensues. All she has to do is just say, "pretty please". Next Penny is in a back bend and held in place with hard steel. She balances on her head as The Pope enters and adds twine lassos to her nipples, then hangs weight on the me. The flogging starts back up, only to lead to a crop used too. Suddenly, we find out that Penny is extremely ticklish, so he exploits that weakness the way he does all of the rest of them. He rips multiple orgasms from her pussy, and in a huge turn of events, he goes back to cropping her pussy into a "pain-gasm". The final scene begins and Penny is in a doggy position with her arms pulled back into a strappado. Her neck is chained to the floor, and after some more cropping, The Pope sets his sights on making her orgasm more than she has all day. Her pussy is filled up with a massive dildo, and the vibe is pressed firmly against her clit. He rotates between her pussy and mouth in a brutal frenzy of fucking. In the end, we have our Penny back, and that's all that really matters.
4 years ago
4921
4:00
Bobbi and Ariel are our favorite kind of friends: gorgeous, latex-clad, anal-whore friends. The chemistry is mind-blowing as these hot sluts take turns worshiping one another's perfect ass with fingers, shaving, spanking, licking, face-sitting, huge toys, and enema fucking. Ariel's firm, round ass is first, as Bobbi eats her ass, peels off her latex, stuffs her full with a glass toy, spanks her, and smothers her face. Then it's Bobbi's turn to get served, as Ariel tastes her asshole, shaves it, fucks it with a glass dildo, and then plugs it with a huge toy that she taps until Bobbi comes. Like a good friend, Ariel licks up Bobbi's beautiful gaping asshole after orgasm. After all that filthy fun, these ass-whores need to get cleaned up. Bobby uses the shower enema to fill her hot, dripping pussy & ass with water she sprays on Ariel's pretty face. But the cleanest ass award goes to Ariel who takes enema after enema while Bobbi fucks her sexy ass with a strap-on. We've never seen enema-fucking like this before. Not to be missed. Filthy, wet, ass-gaping fun.
4 years ago
51283
4:00
Jet Setting Jasmine sits at her leather throne looking gorgeous and powerful. Graveling at her feet in a latex hood is Tony Orlando. She makes him clean her black high heeled shoes with his tongue and so he licks them clean including the soles. Jasmine tells Tony to remove her shoes and worship her stocking covered feet. He sniffs and licks them and she shoves them in his mouth. Next he's told to remove Jasmine's stockings and he does it slowly and continues licking her now naked feet and sucks her toes. Jasmine shoves both of her feet into his big mouth. She makes him remove his leather jock and she presses her toes against his cock and scolds him for producing pre-cum without permission. She feeds it to him with her feet and he tells her he's sorry. She commands him to sniff and to lick her underarms and as he does, she traps his nose and mouth in there, gets him in a headlock and squeezes. In the next scene, Jasmine wields a giant dildo attached to her strap-on. She has Tony bent over a leather padded cage in a black straight jacket, with a blindfold covering his eyes and a ball gag in his mouth. She flogs his ass with a flogger in each hand and after his ass turns pink, she slides the huge dildo into his asshole and fucks him deep. Jasmine puts Tony on the floor with his ass in the air. She slides on latex stockings, lubes them up and shoves almost her whole foot into Tony's ass. He backs up onto his Goddess' foot, trying to fit the heel in, and she takes her foot out and makes him clean it off with his mouth for being such a greedy slut. Next, Jasmine has Tony on his back, on top of a padded table, covered in layers of plastic wrap, unable to move. She cuts a hole, made only for his cock and pulls it out. She lubes up a sounding rod and shoves it deep down Tony's urethra and fucks his pee hole with the metal rod. After that, she relieves her full breasts on to Tony's face, squeezing them and showering him with her breast milk. He frees one of his hands to jerk off and cums while the warm milk rains from his Goddess.
4 years ago
11421
4:00
London River enters the yoga studio of Alexa Nova and right away they start a breathing exercise. Alexa is unsatisfied with London's breathing, so she positions her in "downward dog" and tells her to breathe through her ass. Alexa leans in to London's ass and sniffs through her yoga stretch pants. To get a better view, Alexa rips open London's pants, spreads her cheeks, takes another whiff, and sticks her tongue down her hole. Alexa tells London that she has to open her ass more to get the deepest breath so she has her get into "child's pose", grabs some rope and ties London's legs together so she cant move. Alexa gets a large metal toy and sinks it into London's asshole to begin stretching it. She pops it in and out to make London's asshole gape. Next, Alexa lies on her back and spreads her legs wide to demonstrate a more advanced yoga technique. London cant help but stick her face next to Alexa's asshole and tongue fucks her. London gets a large metal butt-plug and slides it slowly into and out of Alexa's ass. When her ass is good and stretched, London starts slowly putting each of her fingers into Alexa's ass until all five are inside. When London's whole fist finally gets inside Alexa's ass, Alexa cums hard. London gets inspired and wants Alexa's fist now in her own ass, so she puts herself face down and her ass in the air and Alexa lubes up her hand. Alexa's fist gets instantly swallowed by London's hungry stretched hole and with a vibrator pressed onto London's pussy she has multiple huge orgasms while getting fisted. After that, London gets on her back and Alexa gets her leather strap-on with a huge dildo attached to the front. She fucks London's ass deep and hard and they end the session by pressing their assholes together and trib-fuck.
4 years ago
678
4:00
In lavender lingerie, holding a bejeweled butt-plug in her ass, Ella Nova hurriedly cleans the bathroom at the request of her Stepmother, Dana DeArmond. She gets on her hands and knees to scrub the floor when her Stepmother stomps in. Dissatisfied with the job she's been doing, Dana takes Ella and bends her over the countertop and spanks her ass hard. She pulls Ella's panties down and lifts one of her legs up onto the counter, exposing her pussy and bejeweled asshole. Dana tugs on the butt-plug, pulls it out, and tells her that her punishment will be taken out on her asshole. She grabs a double ended acrylic toy and plunges it in and out of Ella's hole, getting little gapes. Dana grabs a Bad Dragon dildo and shoves it down her own throat, covering it in her spit just before ramming it into Ella's warmed up asshole. She fucks Ella's ass with it while she presses an Hitachi vibrator onto her Stepdaughter's clit and lets her cum. Dana lifts her dress and smothers Ella's face with her ass and makes her lick her crack from the bottom to the top. Dana puts the vibrator to her own clit while Ella licks her asshole and cums hard with Ella's face buried in her big beautiful butt cheeks. Next, Dana straps on a huge dildo the size of her own arm. Ella gets on her hands and knees and her Stepmother slowly pushes her big cock inside Ella's asshole. She fucks Ella deep in her ass and Ella cums hard while getting fucked. After that, Dana shoves a rainbow colored cone plug in Ella's ass. She pulls it out and sticks her whole hand inside Ella's ass. She fist-fucks Ella's hole until she cums hard and after Dana licks Ella's big gaping asshole. After that, Dana wishes to punish her asshole even more and so Ella gets on her back and receives two extra large anal beads inside her stretched out hole. Finally, Dana shoves the entire Slink toy up Ella's ass and clean it out with a water enema.
4 years ago
1928
4:00
Kylie Ireland, holy fuck! This woman is a magical unicorn of anal play. The things she can fit in her tiny ass! She comes to set with a huge black inflatable dildo that is bigger than any of the monster toys we have laid out for her and we know we have to up the ante for this girl. The sexy Isis Love doesn't bat an eye, ready to abuse Kylie's ass with everything she's got. Isis stretches Kylie out with a progression of increasingly bigger, thicker, deeper toys to warm up our finest anal gymnast. Kylie is one of those rare, filthy birds who orgasms from anal stimulation alone, and she comes hard with her ass full to the brim. Isis puts her on the gyno table where Kylie's hot slit is already dripping at the sight of Isis greasing up her latex fisting gloves. Isis opens Kylie's pretty little asshole with a bovine speculum until her pink bud is in full bloom, fisting deep inside the spread speculum. With Kylie properly warmed up, Isis shoves both hands all the way into Kylie's ass, fist-fucking her hard until Kylie comes, babbling about what an anal whore freak of nature she is. Fucking right! Isis instructs Kylie to worship her pretty toes. Kylie is an obedient little slut, licking and sucking Isis's foot until it is lubed with enough spit that Isis can slide in into Kylie's ass. Isis foot-fucks Kylie's greedy asshole. When that isn't enough, Isis trades her foot for our biggest toy, a huge black double-dong. But Kylie's ass needs something bigger! Isis grabs Kylie's own inflatable dildo, shoves it up her ass and starts pumping. Finally, Kylie's ass is full enough, and she comes, stretched out, satisfied and exhausted.
3 years ago
2717
4:00
Watch @vek$mr Rides Dildo 2 on now! - @Vek$Mr, Aveksmr, Dildo, Riding, Camgirl, Titty Bounce, Cam, Toy, Babe, Solo, Amateur, Big Tits, Homemade Porn
4 years ago
735
3:38