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.

DJ, like every other man, is a pig and drain on society. Women are fed up with this bullshit. DJ has been stressed out ever since women have been telling their story. His fragile male ego is crushed and is seeking professional help. The stunning Dr. Gia DiMarco has the perfect unconventional therapy for this loser. She blindfolds DJ and bounds his hand in rope. Unable to move, she unleashes physical pain and emotional humiliation on this man. He must repent for his sins, he must learn to respect and worship women, and she is ready to beat that mantra into him. She rips his clothes off, slaps his chest and torments his nipples. His filthy man tongue needs to be taught a lesson and she binds it with clothespins before beating on it with a cane. This filthy loser is getting hard through the treatment and still can't control his male urges so she pulls out his dick and bits on it. She ties up his cock and balls and torments them before putting on a big strap-on to teach DJ the next lesson. What it feels like to be vulnerable and humiliated. Deep anal strap on fucking gets DJ screaming and Gia turned on with excitement of a man in pain. She pulls out a Hitachi and squirts all over this pathetic man. Finally DJ must learn to worship a woman and must learn that woman come first. She shoves her perfect feet into DJ's mouth to gag on. He is made to worship her arches. Finally the true test, can DJ withstand his prostate being milked, while his cock is stroked and edged by a beautiful woman. Will he be able to resist his male urges before shooting his load?

Mistress Evelyn Claire is going to allow her slave to cum but will not make it easy. Edging a man's cock before an orgasm allows for a much more intense experience and an extremely frustrating one at that. Mistress Evelyn loves seeing a big, strong man helpless and begging to cum knowing he is at the mercy of her hands as his cock gets stroked. One final orgasm before his dick goes straight back into chastity for another 30-days.

Mistress Evelyn is an expert at edging out a slave's big load from their helpless balls. There is nothing more satisfying to her than getting a tied up boy so on the edge that he can cum buckets without a hand even on his cock. A true ruined orgasm! With every stroke of pleasure comes a bit more pain to his balls as she slowly closes the vice inch by inch making it as tight as it can possibly go. Once the vice has his balls a beautiful shade of purple then she knows it's time to ruin his orgasm the best way she can.

Goddess Eliza is enthusiastic about seeing men suffer with ball bondage & pain. She has her devotees' balls tied extra tight with the testes split making them look like ripe tomatoes. His balls are also tied around his waist to prevent them from contracting with an orgasm. The man is bent over a wedge so she can tug on his dick will pulling on his ripe testicles. She enjoys dancing the fine line between pleasure and pain. He wants to cum so badly but his balls are bound so tightly. Goddess Eliza finally permits the slave an orgasm. She is not satisfied with his cum offering so she decides to torment him further.

Step-Mommy Domme Eliza has programmed her boy-toy to only cum when a hard dick is in his ass. Her boy has grown so fondly of anal orgasms that he accidentally shoots a big load all over himself before given permission. Step-Mommy Eliza is far from happy with his pre-mature ejaculation and doesn't stop pounding his hole until he cums a 2nd time. She is going to train him to be goodboy once and for all who only orgasms at Step-Mommy's command.

Eliza is the perfect Mommy Domme who is sweet, caring but also strict and cruel at the same time. Best of both worlds! She teases and edges just the tip of her gimp's cock as that is all he is worthy of. His cock is securely locked in a device that only allows just the top of his shaft to be touched making milking day extremely frustrating. Eliza brings him to the edge and back while giving him the full Mommy Domme experience until he is finally allowed to shoot his long awaited load. She takes every last drop of cum and shoves it in his mouth as all good boys know to clean up their mess.

Mistress Diana Grace is training her anal slut to only be able to cum when his ass is filled and fucked. Using a special prostate wand she massages his male g-spot while stroking his helpless cock. She wants to make his first prostate orgasm extra special by also giving him his first anal creampie. Mistress Diana rubs her steel wand against his sweet spot until she milks out a huge load that falls right on his hole. She scoops up all of his cum and uses it as lube to continue fucking him as he begs for the intensity to stop. He has now completed the first stage in becoming a true anal slut for his Mistress.

Once a month the patients at the clinic receive a milking but are still kept locked in chastity for this procedure. Nurse Daphne is an expert at administrating a patient's milking using a high-powered vibrator pressed firmly on their chastity device giving a very explosive orgasm. Her patient is tightly secured down to the bed leaving them at the mercy of the nurse which she works her magic and releases every drop of cum from their balls. The patient is left drained and helpless until 30-days have passed and milking day comes once again.