Strapon Mistress Cassy has a new deliciously wicked way to torment her chastity locked up latex sissy. She decides to bring a Sex Doll into their play. As Cassy fucks sissy Molly with her long strap-on cock, sissy must lick the Sex Doll’s pussy. The only pussy sissy will ever get close to. Then Mistress releases Molly from the chastity cage so sissy can fuck the sex doll. As Molly slowly enters the Sex Doll’s wet pussy, Mistress takes her from behind, sandwiching sissy right in the middle. Once Mistress is satisfied, she ejaculates, shooting cum all over sissies face and inside her mouth.

Just when you thought Part 1 of Gimp Entertainment couldn't get any hotter you stumbled onto Part 2. Temptress Pixie, Raquel Roper and I were just getting started with TheTsSlayer when we decided to unhook our gimps arms and bend him over our spanking bench for another round of aggressively deep pegging with our massive strap-on cocks. Each of us rotate as we gang bang our little fuck toy making sure he's nice and worn out by the time we're through with him. It's a sluts dream come true to receive this level of attention from 3 power Dominatrix's and as you can tell by the end of the clip he is left beyond repair.

Slave Fluffy tries so hard to be the best boyfriend so ultimate mean girl Sarah DiAvola will finally let him fuck her. He lets her spend all his money, humiliate him at the mall, fuck all his friends, outfit him with a chastity device which she can zap his cock from a phone app, worships her feet and endures a hard spanking and paddling with various nefarious instruments. Is is that finally enough? Well, yes, he does get to fuck, but not in a way that gets him anywhere close to Sarah’s pussy. Instead, she straps on a dildo and gives him a thorough pegging in several positions — with his pathetic cock still locked in chastity!

(Custom, no name. Part 2/3) You've been in chastity for the whole week, desperate and helpless. You wanted to see me (your Queen) again so bad. You will do anything for a possibility to have an orgasm. How about you giving up your anal virginity? I will be gentle. Look, I have a nice big dildo. It will spread your ass so well. But first, get down on your knees and lubricate this juicy cock with your saliva. Suck it good if you want to have your permission to cum. Now undress and get on your back. Be ready to receive this juicy cock inside you. Feels so good when your Queen is pegging you. Beg me to allow you to stroke. Your dick is so hard. You love to be fucked! You are getting so close, you went to cum all over my dick. Will I allow you or you will be blueballed again?

Alec works at his computer at home when the lights go out. When he goes to check out the problem, he is captured by Sabien Demonia. He’s stripped naked and tied to a stripper pole. Sabien squats to his level and begins the torment. She slaps his face and calls him a bitch. She smothers his face with her gigantic tits and big beautiful ass. In the next scene Alec is cuffed to a metal pipe. Sabien dresses him in ladies lingerie and puts lipstick around his mouth. She shoves a giant dildo down his throat and makes him gag, spit, and drool. Next she gets a strap-on and puts Alec on his back. She fucks his ass deep and hard as he grunts and squirms beneath her. In the final scene Alec is standing naked, bound to a wall with a white latex gimp mask. Dressed in a slutty latex nurses outfit, Sabien rolls a medical device with spikes across his pale flesh and then jerks his cock until she milks every last drop of cum out of his pathetic cock.

When Gunnar Stone gets caught watching Femodom porn, his girlfriend Freya knows just what to do. She gifts him a cage for his cock and then calls and makes an appointment to see her Friend Ruby who is a professional Dominatrix. The couple meet Ruby in her private dungeon. They lock Gunnar’s cock in a cage and use him as a stepstool. The two spank his ass and spit in his face. They tie him up with rope and slap is cock with a leather crop. They beat his ass with a paddle and whip him with a single-tail. They lay him down and Freya uses his face as her own pleasure device. Freya fucks Gunnar’s ass with a strap-on while Ruby fucks Freyas pussy with her strap-on.

Mistress Riley Reid has a new pony in her stable who needs to be properly broken into submission...by a Big, Fat Dick!

Tony Orlando is in the hospital. Dr Charlotte Sartre tells him that he doesn’t have long to live. He asks if there is anything that can be done and she tells him there is one very risky procedure…. It involves him getting fucked hard in the ass with a huge strap on while someone sits on his face… Fabiana Fox strolls in with a giant pink strap on and slides it in his hole while Bunny Colby assists with the face sitting and also some feet in his mouth.

Bunny Colby is a registered sex offender and has to knock on her neighbors’s doors to tell them that she lives in their neighborhood. She held a dude down and had her way with him with her strap-on. On four separate occasions…Lance Hart invites her in, and she quickly has her way with him.

Muscle jock Sean Costin is one of our most testosterone filled alpha males on our roster, but the roles flip slightly in this one. Our platinum blonde bombshell Victory Hobbs has one fantasy, to be on top and peg the fuck outta a big burly muscle man. Success.

Mistress Payton's slave has been mouthing off all week and needs to learn a lesson before his behavior continues on a downward spiral. Payton gives him a femdom punishment of ATM pegging. Mistress Payton fucks his slave ass with her big dick then shoves it directly into his mouth over and over again. This will teach her slave to stop opening his big mouth unless there is a fat cock being shoved in it.

Why You Shouldn’t Cheat on Pissed Off Hotties Olivia Jay and Mia Molotov. Olivia Jay and boyfriend Tony Orlando are enjoying a quiet evening of basketball and chill. But Tony keeps getting text messages, which he insists are from GrubHub about their food delivery. Olivia is suspicious, so when Tony goes to the door to get the grub, she checks his phone — and discovers he has a side piece! She arranges a meeting with other girl Mia, who insists she had no idea Tony wasn’t single. The two women vow revenge. On his birthday, Olivia blindfolds Tony and takes him to a secret location for an extra special surprise treat. But once they arrive, Tony is shocked to see he’s in a dungeon, and Mia is there, rope in hand and really angry. The women bind Tony to a metal chair and proceed to torment him with crops, flogger and clothespins on his dick and nipples. Tony thinks his punishment is almost over, but no! Next thing he knows, he’s tied to the top of a cage with ass up for easy access with paddles and strap. Once his butt is good and red, it’s time to attach him to a spanking bench. Mia and Olivia return wearing strap-ons, and pound him on both ends till he’s helpless and drooling. Finally, Olivia lets him see her pussy one more time before kicking him out of her house — and then she squirts all over his face before leaving him there for the dungeon Mistress to find.

Welcome Olive Glass to Divine Bitches! Olive can disarm a man with one glance, leaving him helpless. Her beauty and power show no mercy. She chops slave Eli’s ego down into little bits and builds him back up a better specimen. She starts with pouring hot wax all over his back and thighs. Stuck in a cage, with no escape, all Eli can do is scream as his Mistress starts her training. Seeing how well he takes his first punishment, she lets him out of his cage. He kisses her feet, thanking her for making him better. He crawls on the floor after her, just like her dog. She positions him over his cage and flogs him relentlessly all over his ass and back. Then she flips him over to tenderize his front. She paddles his sides, thighs, and belly. Her pristine milky white skin is relentless when brushing up against Eli and he can barely control himself. She whips him into shape, pegs his ass with hard strap-on fucking and even uses the fuck saw power tool deep in his ass. The joy on her face when he takes it for her is priceless. Eli’s body shakes with the intensity of the fucking and he begs over and over again to cum but is denied. She then uses him for her pleasure and denies him any of his own. She sits on a dildo gag strapped to his face and as she rides it, all Eli can do is stare up at his beautiful Mistress’ cunt. Seeing his cock straining in chastity, she laughs delighted, before taking it in her mouth to further torment him. Mistress Glass is a Goddess you will not be forgetting anytime soon!

Officer Jane knows her prisoner is hiding something deep in his ass and whips out her big, black probing cock to hollow the whore out. No hole will go unsearched as Officer Jane stops and nothing to find the evidence she needs to keep him locked up for life.

Natalya plays with her makeup while her brother danni cleans her bedroom. Danni is in chastity and has to do everything his sister says. He’s been cleaning and organizing Natalya’s extensive closet for hours. Natalya made an agreement with him that if he completed the task, she’d let him out of chastity. Now danni has finished cleaning, but Natalya doesn’t feel like upholding her end of the bargain. Danni complains. Natalya doesn’t like him badgering her. Danni’s acting up. Their mother has said that if danni acts up, Natalya has the authority to peg her brother, to bring him back in line. Natalya ties her brother to her bed. She comes around behind him with a big thick cock she’s borrowed from their mom. Natalya fucks her brother long and hard with his chastity key around her neck. Her brother’s chastity jingles while she fucks him. Nobody in the household will come to danni’s aid. The women in his family are against him. Danni and his father are beta males. Danni doesn’t bother to cry out for his mother, because if she were to hear him, she’d just come in and fuck him with an even larger dildo. Danni deserves for the women in his family to hate him. It’s all his fault for being who he is. Natalya grabs her brother’s slender hips and thrusts the cock in deep. She’s decided that she deserves a bigger cut of his allowance next week. Ass fucking isn’t punishment enough.

If it's one thing all sissies need it's to be constantly filled with cock. Mistress Naomi's sissy rubber maid has proven to be very useful and deserves a reward of a thick, strap-on dick fucking his slutty holes.

Mistress Naomi's slave has been properly trained to be completely addicted to her strap-on cock now that his dick is forever locked in chastity. He is such an obedient fuck-toy that he will willingly take any size dick that she throws at his hole just so he can have some form of pleasure. His locked cock is totally useless making his holes the only way he can get off. Slaves are meant to be ass sluts and Mistress Naomi puts his hole to work making him beg for more.