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
920
4:00
Cybergirl Alana Wolfe makes a splash in this poolside video from producer Joel London. All natural, with pale blonde hair, blue eyes and soft, pale-pink skin, Alana sure looks good in a bikini—she’s got a tight little body, and she’s not afraid to show it off. “I’ve worked very hard to become a part of the Playboy family,” she says. “I was a Painted Lady at Midsummer’s, which was a dream come true. I had to walk around naked—well, wearing body paint—in front of hundreds of people. I’m comfortable with my own body and have no issue being nude!” Speaking of issues, Alana’s got her sights set on International editions of Playboy magazine. With some of her Aussie peers gracing those pages, we think it’s only a matter of time before Miss Wolfe lands her own centerfold. Hit the pool with the unbelievably hot Alana Wolfe, right here on Playboy Plus.
4 years ago
460
6:00
In a city like San Francisco, smoking cigarettes is a crime without comparison. While thieves, murderers and bankers might be taught the error of their ways and rehabilitated, the smoker is a degenerate who deserves no mercy. Or so teacher's assistant Ashlynn Leigh learns when Bobbi Starr, the dean, catches her while taking a few drags and thinking about flavor country in the locker room. As punishment for the facility's strict no-smoking policy and for possibly corrupting the students, Bobbi places Ashlynn in a rehabilitation center for 24 hours. Though she protests, the need for a paycheck outweighs her sense of injustice about the situation. In the rehabilitation center, head warden Isis Love lays down the rules on the otherwise indifferent Ashlynn. Restraining her with handcuffs, Isis shows how the tools of her trade can be the agents of pleasure and pain. Ashlynn is teased with Tasers, sparking with electricity while she removes her clothes for the prurient interests of the warden. Rehabilitation is far from her mind and to start, Ashlynn's elbows and chest are wrapped, framing her tits for Isis to play with. Then, with legs spread-eagled on a bed, Isis takes control of Ashlynn's muscles, the current causing them to spasm at her will. But Isis can't resist administering as much gratification as she does discomfort, fucking Ashlynn's worn pussy with an acrylic plug. Isis concludes the sentence with a metal plug in Ashlynn's ass and a dick-on-a-stick in her cunt, double penetrating her while tied in doggy.
4 years ago
945
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
4920
4:00