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Best porn of Pain
Total Videos: 2039
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
939
4:00
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
579
8:00
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
488
6:00
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
4925
4:00