Category Archives: pain

Penny’s Anal Embezzlement

When Penny Pax is confronted by her employer’s security officer for suspected embezzlement of funds, she denies any wrong till she is cuffed, frisked and fucked by Stirling Cooper. Includes tight bondage, gags, nipple clamps, beautiful anal, deep throat fucking, zappers, vibes and all of Penny’s favorite things.
After tearing Penny’s clothes off and frisking her big tits and sexy ass Stirling offers her a choice between going to prison or coming to a special agreement. Well Penny can’t deny she is curious about what’s going on inside Stirling’s trousers so maybe just a quick blow job to find out. With hands cuffed behind her back and drool dripping down her tits Penny gets a deep sloppy throat fucking with Stirling’s big hard shaft and Penny can suck cock like a champ. Wearing sexy fishnet stockings Penny is gagged and tied up perched on a stool with ass spread high in the air for easy access. He teaches her a lesson about stealing first with the flogger, then the crop and then his big dick! Stirling fucks Penny’s puffy pussy and then slides it inside her tight ass for a deep pounding which she loves. Finally tied up on her back with legs spread wide open and clothes pins on her nipples Stirling zaps Penny’s tits, sensitive pussy and thighs and gets her to admit she is a thieving slut! But the pain turns to pleasure when Stirling hammers both Penny’s slutty holes one after the other with his grade A prime man meat until she is begging to cum. With the vibrator on her pussy and his dick pounding her ass she is loosing it but Stirling makes her wait which makes it all the sweeter when she can let it rip and Stirling shoots his white hot load all over Penny’s pussy. Pleasure doing business with you Mr Stirling!

BOUND PRISON Part 3: Paying The Piper

Officer Michael DelRay waits impatiently in an open, empty jail cell. Officer Jeremy Spreadums is late for their meet-up to split the money that Officer Spreadums has collected. When Officer DelRay suspects that Spreadums is holding out on him, DelRay …

She Smiles When The Pain Comes

There are a lot of beautiful women in this world, and The Pope is one lucky SOB to be able to work with so many of them. This, however, is the first time that he’s able to walk up to one of them and they can look him directly in the eye. At a towering …

She Smiles When The Pain Comes

There are a lot of beautiful women in this world, and The Pope is one lucky SOB to be able to work with so many of them. This, however, is the first time that he’s able to walk up to one of them and they can look him directly in the eye. At a towering …

Dungeon Muscle Challenge: Two Pain Sluts Pushed To Their Limits

Welcome back to Master Keys Dungeon. Today on the menu we have two submissive pain sluts ready for torment. Draven Navarro is 200 pounds of thick muscle meat suspended in fully restrictive rope bondage. Every muscle bulge makes the bondage tighter. And…

Beefcakes Pierce Paris and Blake Hunter Battle for Dominance!

Leather men Pierce Paris and Blake Hunter stumble into the dungeon in a heavy make out session. Their muscles ripple and flex as they wrestle for dominance. Finally, Pierce gets the upper hand and slams Blake into the wall. Hand around his throat, Blak…

Bad Boy Toy

Lounging on the couch, talking on the phone, Mistress Arabelle Raphael rests her feet up on the back of her piece of human furniture, DJ. Through his leather mask, he tries to slyly lick the tips of Arabelle’s high heels and she notices. She digs her h…

Executive Discipline: Cherie DeVille Humiliates Her Boss Mike Panic

The beautiful blonde MILF Cherie DeVille is a very hard worker. In fact this strong woman has worked soo hard on this last assignment for her boss, she did all the damn work. She has devoted all her important and valuable time to his company but patria…

Sexy Blonde Cougar is Destroyed in Device Bondage

Helena has proven that she can handle the most diabolical bondage and torment, but can she take what comes next? Her first showing was impressive and we know that The Pope isn’t going to stop there. He is going to take it deep into the next level, and …

Hard Up Hole: Max Adonis gives up holes for protection

Max Adonis doesn’t know how he’s going to survive in prison. He narrowly escapes his first shower with his holes untouched. Luckily Max’s bunkmate, Dominic Pacifico, is a man no one will mess with. Dominic offers Max protection for a price — exclusive…

Statuesque Blonde, Ashley Lane, Drenched, Defiled, and Shamed

Ashley Lane is truly beautiful, but nothing is more exciting to Mistress Kara than the beauty that pain brings to her submissive. As the elegant blonde is led through the town square she sees the edge of a breaker wall that falls into the sea and Mistr…

Lonely for your pain: Aiden Starr dominates partner Sebastian Keys

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 h…

Pierce Paris Manhandles Tony Orlando

With his face covered by a leather hood, a ball gag in his mouth, and completely bound in rope, Tony Orlando is dragged across the floor by Pierce Paris into his lair. They settle under a bright light and Pierce flips Tony over, takes down his jeans, c…

Buck Wright Bound and Beaten

Standing on a wooden box, shirtless and wearing black leather pants, Buck Wright is bound in red rope. Both of his wrists are tied to the ceiling and both ankles are secured to the wooden platform on which he stands. He waits, smiling in anticipation a…

New Male Dom Made to Submit and Take Pain from Goddess Bella Rossi

Bella Rossi finds male dom Dozer in her dungeon confined in strict bondage! Electricity pulses through his cock as he kneels with his hands tied above him. Dozer is a typical male dom — he’s arrogant, mouthy, and needs to be put in his place. Nothing …

New boy Tom Bentley fucked by leather doctor Trenton Ducati

Tom Bentley awakes to find himself chained down to a metal table in a bizarre operating room. His calls for help summon mad leather doctor Trenton Ducati, masked and wearing a leather apron. Dr. Ducati has plans for his newest specimen. He can’t wait t…

Busty Blonde Sienna Day Disgraced Fully Nude on Dirty Public Streets

Come join Steve Holmes one last time as we celebrate LGBTQ Pride with the beautiful busty blonde Sienna Day. This bouncy fully submissive slut is nude outdoors and running around barefoot on the dirty busy public streets. Her body is on dsiplay for hun…

Busty Blonde Sienna Day Disgraced Fully Nude on Dirty Public Streets

Come join Steve Holmes one last time as we celebrate LGBTQ Pride with the beautiful busty blonde Sienna Day. This bouncy fully submissive slut is nude outdoors and running around barefoot on the dirty busy public streets. Her body is on dsiplay for hun…

Syren de Mer Submits Every Hole to Helena Locke

Helena Locke has high expectations of her subs, especially Syren de Mer, who comes to her ready to submit. The chemistry between them is dripping hot as Helena uses Syren in every way, punishing her when she disobeys, and rewarding her for a job well d…

Date Night: Eliza Jane Stuffs Pierce Paris’ Balls in His Ass

Couple Eliza Jane and Pierce Paris finally have a night off together! Eliza really wants tonight to be special and orders new toys to try out with Pierce. Pierce is hesitant at first, but will try anything for Eliza. He strips for her, revealing his to…

Muscle stud Cliff Jensen lays claim to prison bitch Tony Orlando

C.O. Sebastian Keys drops off fresh faced inmate Tony Orlando with his new cellmate, ripped bad boy Cliff Jensen. Cliff knows a bitch when he sees one and immediately starts pushing Tony around to see what this little quivering prison mouse is made of….

Pretty boy Zak Bishop gets trained by Master Pacifico

New meat Zak Bishop is reporting for slave training at the feet of leather daddy Dominic Pacifico. Master Pacifico wastes no time having Zak strip before binding him to a cross with his limbs spread and starting his lessons. He flogs Zak all over his c…

Svelte Blonde Delirious Hunter Punishes and Fucks Buttslut Slave

Delirious Hunter has her sights set on pain slut slave DJ. She covers his chest in plastic clips and has him tied in place by his wrists, ankles, cock and balls. Hooded, unable to see his Mistress, DJ waits anxiously, yelling in pain as Delirious brush…

Olive Glass Puts Up Every Hole For Whipped Ass

Olive is super excited to shoot for Whipped Ass, and she wants it all: spanking, flogging, fucking, anal, pussy licking…everything! She’s a natural submissive, ready to please, and with Cherry Torn calling the shots, she gets it all and more! Cherry …