A big strong boy does all he can do to escape this tiny girls silly little velcro chair. I even stroke his dick and make fun of him to help. Let's see if he can escape the inescapable restraint chair!

I tricked him about the duration and subject matter of this scene. Couldn't be more real, he's been there hours. The prisoner wants out and I flatly won't let him. The ruin at the end is a piece of precision work that I am proud of and happy to share. An explosive cumshot gets all over me, shooting for many long seconds and yet he goes crazy with anger and dissatisfaction. Still, no freedom.

Opening visits from a five hour edging scene with my vanilla boy who I got to try a scene because he was "curious". Now he's in an institutional chair and that means he's mine. And over two intense visits I tell him how I know he's been watching my videos and I know he's been following my projects and now he's getting the most intense edging treatment I've ever given because he's not the beginner he said he was and I don't like dishonesty. Two major visits here, so only highlights is the part you see on this clip.

I tease the boy for over an hour, this is just the highlights. I have fun forcing him to stay on the edge, he knows from our past encounters that I'm capable of punishing him if he cums. Later he told me he has never been edged so intensely in his life. I'm not really surprised, I'm talented at keeping someone on the cusp of finishing.

When Princess Jill Kassidy demands an orgasm from her slave she makes sure she always gets one. No man can resist cumming when there is a high-tech machine milking their cock.

Mistress Jill Kassidy loves when you are being such a good boy that it makes her proud to call you her property. She loves just how hard you work to please her every desire and thinks all good boys deserve a special reward in the end. Your 7-day chastity sentence is officially over as Mistress Jill starts to stroke your raging hard cock just the way you love. She knows all the right spots and all the right moves to really make you explode. Hope you enjoy this special reward slave as your cock is getting locked right back into chastity as soon as you cum. Just because you have been a good boy doesn't mean your cock is going to be set free. It's mine just like you! -xxo Jill Kassidy

Mistress Jewelz slave is finally getting what he wants today..except there is a twist. He's been wanting to feel that sweet release of an orgasm for far too long after being teased and denied for months on end. He is on perfect display with his body completely exposed and vulnerable for his Mistress to have her way with. She just loves the look of a man tied up knowing they have no control whatsoever. Mistress Jewelz lubes up his helpless cock and strokes it until he is begging to cum for the 1st time in forever. If he is going to be allowed to cum it's going to be her way and her way only. She edges out a massive cum load all over the floor and scoops it all back as a boy needs his dinner. Growing boys need to eat and a big, sticky load of cum is exactly what Mistress Jewels has planned for the bitch. She knows how much he hates the taste of his own cum which is exactly why she loves shoving it down his throat.

Mistress Jenna has transformed her slave into a helpless leather gimp. He failed as a human and hopefully will become a much better slave now that every choice has been taken away from him. Miss Jenna is pleased with his 1st week of training as her obedient gimp and rewards him with a slow, teasing orgasm. What he doesn't know is Jenna has one more special reward in store and makes him lick and suck off every last drop of cum from her hands.

Before Goddess Jane Wilde rewards her slave with his weekly milking she wants to really make the helpless bitch suffer. She truly gets off on teasing her slave with her tight, young holes being smothered right in his face. The only hole he will ever be fucking though is the one her hands make as she tightly grips and strokes his slave cock to orgasm.

Sherman Maus and Kacie Castle are supposed to be sitting silent, in bound punishment, imposed by the fierce and sexy Isis Love, but Sherman can't keep his mouth shut. He mocks Kacie and calls her a brown-noser and a kiss-ass since she's generally an obedient little slave. They bicker back and forth until Isis Love catches them in the act. Startled by her presence, they blame each other for the disturbance. Isis has no choice but to punish both of her subs. She begins with corporal punishment just to warm things up, flogging and whipping them into redemption. Then she clamps these two little slaves together with their tongues and nipples so they learn to get along. After all, "teamwork makes the dream work". Kacie then gets a little imposed pleasure with the vibrator as Sherman is made to watch. Tied up and with his cock in chastity, poor little Sherman can't do anything but helplessly watch Kacie orgasm. Isis then pulls out a huge strap-on for Kacie to suck on. Kacie gets it nice and wet so Isis can pound Sherman's ass with it. Sherman then gets pounded hard by Isis's huge dildo as he eats Kacie's pussy. He gets flogged and pounded and close to orgasm but he is denied. Isis then makes Sherman fuck Kacie's hot wet pussy. This steamy punishment gets hotter and hotter as Isis makes Kacie lick her pussy too, so she doesn't forget who is in charge. Isis then uses the vibrator on herself and squirts all over Kacie, as Kacie gets pounded by Sherman. Now that the team is coming together, Isis lets Sherman bust his load all over Kacie's wet mouth. Now that these little slaves have been taught a lesson in teamwork, they are ready to serve.

Mistress Isabelle allows her newly trained sissy bitch one final milking before his transformation is complete and his clitty stick is locked away forever. His balls are tied, tucked and pulled as far back as they can possibly go. Isabelle strokes his horny clit stick edging it until he is ready to burst. She makes the sissy throw his legs over his head and shoot a huge, nasty load all over his face and into his gaping mouth. He is going to be a very well-trained sissy cum dump but needs to learn how to take and swallow gigantic loads like a good whore.

Finally Mistress Isabelle has turned Kade's disobedient behavior around showing him how good life can be when one follows the law. Due to his past infractions, his reward isn't exactly what he had in mind only being allowed to feel the firm grip of Isabelle's hands on just the tip of his cock. She has him in strict bondage and his cock locked in a steel device making only the tip accessible and everything else completely out of reach. Maybe when he proves he can remain an obedient boy he will one day receive the pleasure of having his entire cock stroked..maybe

Officer Deltore had her prisoner's cell tossed but it came up clean meaning he has deserved a special reward for being so compliant. Milking day only comes around once a month and when a prisoner has not been on his best behavior he gets skipped. Good behavior is certainly rewarded so Officer Deltore makes sure her prisoner is properly milked while he stays locked in his kennel. As his special reward on milking day he is allowed to fuck her pantyhose covered legs with his rock hard cock. She knows how much he adores her shiny patent leather boots and milks his cock all over them as a lovely treat to lick right back up. 30 more days until milking day comes around so he better continue to stay extra compliant to her rules or he may not be cumming again for months.

We filmed this clip last year right after Isabella’s 18th birthday! Bratty Isabella teases you with her fingertips, then starts stroking up and down your shaft. You grow even harder as Isabella wrinkles her cute little bare soles. Even though you have a suspicion of how this milking will end, you can’t help but spill a massive load for her. Bratty little Isabella ruins that nice big orgasm. She is exploring sexuality and learning how to control men with her newfound power over them.

Amen, I say unto you, this is the place of the worst sin - the house of a humungous tyrant and his grisly family. They threw a feast and the tables are flooded with food. At the table, kidnapped women being fattened up for the insatiable master who likes to munch on their fat pussies and huge tits full of milk. This is the place where the orgy of gluttony and sex happens. Nobody leaves the table until he's full of sin!

When men first have a prostate orgasm they fall in love with rectal orgasms, Gigi Allens knows how to milk a prostate properly. She slides her fingers into his hole and applies pressure to his male G-spot while stroking his shaft. The slave is overwhelmed with intense pleasurable feelings as her fingers circle his prostate. Gigi stimulates his prostate until making him erupt then feeds him the result.

Goddess Gigi uses a vibrating prostate milking wand to thoroughly drain every last drop of cum from inside her slave. She turns it on to it's full power giving him no option but to have his prostate completely milked like a slut.

When you belong to Mistress Gianna you give up complete control of your cock and every last one of your orgasms. Her slave still needs to understand this simple concept that his orgasms are no longer under his control. Mistress Gianna slowly and sensually edges his cock while making sure he is paying complete attention with firm slaps to his helpless balls. She shows him how good ownership can be for obedient slaves that know their place by edging out a thick load of cum.