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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
942
4:00
Three cute and nerdy friends, Ivy Wolfe, Judy Jolie, and Alison Rey, are playing a tabletop roleplaying game called Labyrinths &Leviathans. Ivy is the all-knowing Labyrinth Mistress (LM) while Judy and Alison are the brave souls on an epic adventure.They're all getting deep into the story, celebrating having slain an ogre, when Ivy's snobby cheerleader step-sister, Whitney Wright,waltzes in. Immediately, the friends fall into an uncomfortable silence as Whitney plops down at the table with them, announcingthat she's stuck with them for the night. What game is this? One of their dorky pretend games with magic? Whatever, she wants in.Reluctantly, they let Whitney play, although it isn't long before she's mocking their enthusiasm for the game. When Ivy challengesher step-sister on what she'd have HER character do, Whitney smirks and says she'd have her character put a love spell on Judy'scharacter to make them kiss!Just like that, Whitney's cast out of the fellowship and the other girls try to get back to playing a proper game. As Ivy continuesnarrating their adventure, Whitney rolls her eyes and slides in behind Judy and Alison, getting up to no good. Whitney starts teasingthem in seductive ways, playing with their hair or caressing their backs. She even goes as far as groping their perky breasts beneaththeir shirts! While Judy and Alison first seem uncomfortable, they soon begin falling under Whitney's spell, much to Ivy's dismay.Despite Ivy's vehement protests, when Whitney dares Judy and Alison to be as bold as their characters, they're unable to resisttemptation any further. Ivy can do nothing but stare in shock as the other three girls undress before her and starts getting it on. AsWhitney fingers and tongues Judy and Alison's sweet pussies, Ivy does her best to keep her wits about her. However, it isn't longbefore her own resolve finally crumbles -- it looks like the game will just have to wait!Story inspired by an original submission by Girlsway member, Doctor Jackson!
4 years ago
1050
6:14
Alice (Sara Luvv) wakes up thrashing in bed, tormented by the voices in her head that are taking control of her body, and pitting her between two multiple personalities, lipstick lesbian Alicia and butch Al. But Al has sexual urges that make her personality harder to suppress. So, Al gets out of bed, slips on a smoker's robe and lines up a day's worth of pussy (Jenna Sativa, Charlotte Stokely, Abigail Mac). Before she can finish fucking them all, Al blacks out. Her multiple personalities flicker in and out of consciousness, until Alice comes back up. She doesn't remember what made her decide to stand outside naked, or why a stranger is offering her flowers.
<\/br>She runs back inside and cowers in a heap behind the front door, just as the councilor Ellen (Serena Blair) from Safe Spaces knocks on the door, called over by Alice's concerned roommate Christy. Grateful to see Ellen, Alice explains her blackouts and migraines. Alice suspects she had sex with a goddess the night before, and woke up possessed by two lesbians' spirits. She can feel them with her now, and she thinks they're masturbating.
<\/br>Ellen offers to hold a seance to communicate with Alice's alter spirits. She instructs Alice to remove her robe, and lie on the floor spiritually. Surrounded by candles, the medium waves her hands over Alice's naked body and summons Al, and then Alicia. But the two inner lesbians conspire to gang up on Ellen and fuck her as a team. Alicia starts kissing Ellen too sensually for her to resist the seduction. She puts her dark puffy nipples in Ellen's mouth and coos when she sucks them. Ellen tries to regain her composure, thinking she must resist having sex with her troubled and possibly haunted friend. But Al takes over and pushes Ellen's face into the floor and eats her bare ass. Al folds Ellen's naked body into plough position, with her legs thrown overhead. Al inserts her fingers in Ellen's pussy, extracting her orgasm with her tongue. Then pretty Alicia takes her turn, daintily telling Ellen she'd like to get fucked. She opens her legs, and Ellen obediently licks up and down her landing strip, till Alicia melts in her mouth. Al comes back hungry to fuck Ellen. She begins tribbing Ellen's pussy with wild abandon. When Alicia returns, the lesbians grind their pussies till they cum. Finally, Alice fights her way to the surface, but she's no match for the other two lesbian personalities. Ellen is left trapped in the closet, as the Faces of Alice head out to have more fun.
4 years ago
1916
6:15
Once upon a time, a young lady named Ashley Grace came to this site and orally gratified Mr. POV until he messed up her face with yet another one of his big pov facials! She's now Alexis Grace, and she's better than ever. She's bustier...she's naughtier...and she talks dirtier than ever before. Lemme say I love big, fake tits. I know some dudes don't, but to me, when a woman gets her tits done, it's a sign to the world that she's a fucking slut. Look how big Alexis's are! Look at her fingernails, too! But let's talk about Alexis's fetish -- a man's "pee hole". She loves them! Her favorite thing to do? Shove her tongue in it! Her nails, too! As she says, it "opens it up" of a bigger load! Which Mr. POV delivers, too! This is a fetish lover's delight! And follow @Alexisgrace_XXX if you're on twitter. She's a Fetish Queen!
4 years ago
1423
5:59
Aiden Starr and Sebastian Keys star in this special update of Divine Bitches. When these two long time BDSM practitioners and current partners get going, things get hot fast! Sebastian starts in an inverted ankle suspension with his hands tied behind his back. As the anticipation of being thoroughly used by this Goddess sets in, he begins to sweat. Aiden places four sets of clover clamps on his balls and another set on his nipples. She flogs his ass before getting a crop to work over his ass and thighs, turning them bright red. Sebastian screams gratitude and adoration for Aiden as she relentlessly smacks his sensitive thighs. When he can take no more from the crop, Aiden uses the zapper to shock him all over, paying special attention to his sensitive nipples. Next, Sebastian is collared and cuffed with a spider gag stretching his mouth open. As Sebastian drools all over himself, Aiden flogs his back and ass and canes his thighs. She fucks his face with her fat cock. Sebastian takes as much as he can, gagging on her cock as he stars up at her perfect cunt. Then she takes off his gag and chokes him with her hand before spitting in his mouth. Now that his mouth is all stretched and ready, she begins to stretch his other hole. She bites down on his balls, stretching them as she works open his ass on her fingers. Finally, she gives this hungry buttslut what he desires most -- her big hard strap-on cock. Sebastian moans his ass opens up around Aiden's dick. His groans increase as Aiden plows his ass before flipping him over to fuck him on his knees. Using the handle on his collar to hold him in place, she fucks the shit out of him as his collar chokes him with every powerful thrust. When his slut ass is good and open, she fucks him with her hand, filling his ass with four fingers. As she incessantly milks his prostrate, Sebastian begs to cum. Finally, Sebastian is tied down on Aiden's bed. She edges him mercilessly as he begs to cum. But he doesn't get to cum before her! Aiden uses his cock and sits on his face and lets this lucky slave worship her glorious pussy and ass. She cums hard all over his face as he licks her perfect asshole. Then she continues to edge him until he explodes all over her hands. Delighted, she continues to work his sensitive cock as Sebastian cries out, squirming to escape her touch. Then she gathers up all his cum, rubs it all over his disgusting face, and makes him lick her hands clean. Finally, she shocks him with the cattle prod before leaving this cumslut in his own juices.
4 years ago
480
4:00
Charlie is in the kitchen baking a cake when her son's friend Peter shows up. "It always smells so good here," he says. "What are you baking?" Charlie says she's baking a cake for her son, but Peter knows that's a lie when he sees the cake. It's a cock cake! "That's for Billy?" Peter asks. She fesses up. Her girlfriend is getting a divorce, so she's making her a cake. Isn't that nice of Charlie? The cock cake is very detailed. It has balls and veins. It even has cum. "Does Billy know about this?" Peter asks. Nope, Billy doesn't know, and Charlie's going to make sure he doesn't find out...by sucking and fucking his 22-year-old friend into silence. Charlie, by the way, is 63. She's married. She has children and grandchildren. And she enjoys doing things most 60somethings don't do. Blowing a 22-year-old is one of those things. Flashing her tits for beads at Mardi Gras is another. Of course, fucking on-camera is the biggest thing of all. Charlie lives in Colorado with her husband. She used to be a nurse. She does, indeed, enjoy baking. She also likes going to the movies. And going to nude beaches. And masturbating. "I have all the latest toys to go with my fantasies," Charlie said. Fucking young guys is one of them.
3 years ago
1924
5:21
The type of woman that really gets my balls boiling is a busty, sexy, mature woman. All that sexual experience added to an amazing figure, and you have an idea of my next patient that walked into the office today. Sandra came in complaining of a bad back and I instantly noticed her breasts thrusting out at me through her top. Great legs framed by a short skirt were making my dick twitch like a rabbits nose. I got her onto the examining table and began my examination. I mentioned that bad backs could be caused by big breasts putting strain on her back muscles. She sat upright, and now I could get a closer look at them, I noticed she had a scar down the middle of her cleavage from heart surgery years ago. Now this could be my window into getting my cock deep inside this sexy woman. I told her some lies about how I knew some surgeon friends that could remove the scar and that I could get her a free consultation. She was overjoyed at this news, so then I pulled the scratching backs card. As I was helping her out, maybe she could help me relieve some of the stress from my job. She was flirting with me so I knew that she would be up for a bit of fun. Within minutes the pain in her back seemed forgotten as she was on her knees taking my cock deep into her mouth, licking and teasing the head and running her tongue over my balls. The sexual surgery deal had been struck and was in full swing. I bent her over the examining table and fucked her tight pussy from behind. I was loving every minute of this. We fucked in a few positions and I soon had those big breasts of hers flapping around as I fucked her hard. She was an amazing shag, her body was making me so horny that I deserve a medal for holding onto my troops for so long. Eventually the horniness of the whole situation caught up with me and I pulled out in time to fire my salty salvo over her stomach and pussy lips. What an incredible day at the office, now onto my next patient.
4 years ago
580
8:00
Argentinian models Marga Cifuentes and Celeste Sablich get very, very naughty in this video from producer Mariano Rocca. With dark chocolate-brown hair, brown eyes and warm, caramel-colored skin, these Latinas are as hot as it gets “ and with the addition of a blindfold and a little dessert, things are about to reach the boiling point. Playboy is about sexual liberation, says Marga. Deep down, Im a romantic “ I want everything, but not with just anyone! Lucky for her, Celeste is not just anybody. Watch as she pours raspberry syrup all over Celeste, licking it off of her full, round behind “ before you know it, theyre locked in a long, sensuous kiss, and more than ready to take it to the next level. Hope you saved room for dessert, guys “ fill up on Marga and Celeste, only on Playboy Plus.
4 years ago
484
6:01
Planning the perfect surprise present for her husband, Tanya Tate books photographer Brett Rossi to shoot a family portrait of Tanya with her step daughter Samantha Hayes. They look like twins in matching black dresses with ringlets in their long flowing hair. But little Samantha is much shyer than her MILF step mom. Brett helps the girl come out of her shell, getting her to lighten up in front of the camera, and have fun posing like model. Brett snaps a lot of photos and gradually gets the girls into sexier positions. Tanya wants the photos to look intimate to reflect their close bond, but Samantha needs convincing when the poses get a little more risque. After all, her father will see them! She reluctantly agrees to show her pink panties in the picture, sitting with her legs spread. But then the dress comes off, followed by the bra and panties, and Samantha has nothing left to remove. That's when Brett suggests that Tanya takes off her dress. She positions the naked brunettes in various positions, depicting sex acts between mother and daughter. But soon the positions become more sex and less act. Samantha is a virgin and no one's put a tongue on her clit before her step mom. Brett puts the camera on a self-timer, and inserts herself into the lesbian sex scene. Tanya and Brett team up on Samantha, fingering and tribbing the girl's pussy, then eating her like the meat between their sandwich!
4 years ago
968
6:15
It was just another boring day at the office until Tera Joy showed up, but as soon as the stunning raven-haired MILF sat across from me, I was completely entranced. Maybe it was how her mouth moved when she spoke, with those bee-stung lips, and that sultry, sexy voice. Or perhaps it was the glint in her dark gypsy eyes, like she knew the answer to a great, sexual secret. Whatever the reason, I could think of nothing but getting this hot chick's tongue in my pussy! I led her through the usual questions and had her undress, pretending to size up her big natural tits for the agency, then I asked if she'd be willing to shoot video. When she told me she'd always had a fantasy about lesbian sex, I knew I had to take my chance! I pulled off her panties to lick her perfect pussy, then fucked the horny Czech babe with my strap-on until she exploded with an orgasm that shook her entire body.
4 years ago
1939
8:00
Angela White is laying out on her backyard taking the sun. On the other side, Markus is looking for treasures with his metal detector, as he gets closer to Angela the detector starts beeping. He gets curious, scans her body and detects something strange inside her ass, She gets nervous, but he wants to know what is going on and rips her yoga pants exposing her round ass to find a metal butt plug in her ass, he starts playing with it but Angela gets horny and decides to take him inside the house to give him the fuck of his life. They start having rough anal on a stool in the kitchen where Angela squirts many times, then they move to the living room and from this point on, the sex gets even rougher, she squirts everywhere, it becomes a violent combination of bj, ass licking, tit fucking, ass to mouth, squirting and anal sex.
4 years ago
1129
5:00