Regular chastity training has failed for Mistress Evelyn Claire's slave. His dick still manages to always be on his mind putting his needs 1st which is a big problem for his servitude. Mistress Evelyn has been patient up until this point but needs to take it to the next level to get it thru his thick skull. Her evil chastity device firmly locked around his cock will make him submit physically and mentally whether he is ready or not. With the slightest erection, the spikes will dig deep into his cock forcing him to focus only on his Mistress's pleasure. Training is never easy though as Mistress Evilyn sexually teases his locked cock making it as hard as possible to not get aroused. The more he screams the happier it makes her.

Mistress Evelyn truly loves a man who thinks he is a big, tough guy yet crumbles at the sight of a strap-on cock. He says he can handle anything but as soon as Mistress Evelyn's strap-on slides deep in his ass he breaks and cries like a little bitch. This is music to her ears as the more he suffers the harder she pounds his tight hole. She will make him into a cock loving whore whether he likes it or not by the time she is done wrecking his sissy ass.

He may look tough but once his cock is locked in chastity he becomes a little bitch crying to be released. He said he could handle anything so Mistress Evelyn put him in chastity right from the start. The slave is so horny with always being denied that his cock presses against the bars of the cage making it far from pleasurable. The way he cries and suffers brings so much joy to Mistress Evelyn's day that she wants to push his agony even further. Using her toys of tease and denial she makes the bitch cry in sexual frustration wishing he never agreed to give away his freedom.

You have fallen deep into a state of slavery as your life is completely controlled by the young Mistress Emily Willis now. You are kept locked in your cage just like your cock is kept locked away in chastity as your Mistress demands. Not like you have any say in the matter so you better get used to a life filled with locks and cages as that is where you will spend. Mistress Emily is heading out for the evening to go get fucked by lots of big cocks while you remain locked up tight as her good-boy cuckold. She is a very slutty Mistress and just can't get enough dick as she teases you with the thought of being by her side while real men have their way with her. Just because you are in a cage doesn't mean she won't tease the hell out of you and your locked cock making you wish you were worthy enough to fuck her. Luckily you are her favorite cuckold and she is going to grace you with her cum-filled pussy to lick and clean up when she gets home. Isn't that what you have always dreamed of? To be kept in a cage and forced to lick her creampied pussy while your cock remains locked away in chastity?? Of course it slut! Now show your Mistress your sissy pink chastity so she can tease and deny that horny cock of yours...

Mistress Emily has transformed her slave from a man into nothing but 2 fuck-holes for her strap-on cock. She is going to use his whore holes and make them even looser than they already are. When she decides to finally loan his ass out to any cock of her choice he will be just a gaping hole ready to please. Her fuckboy is hooded and restrained to really cement the fact that he is just a hole made for servicing cock. He will no longer know the life he once had as a man as now his only goal will be to service and pleasure dick after dick for his Mistress.

Mistress Emily Willis has planned something very special for her cuckold slave. She has upgraded him from cuckold left in a cage to a cum lapping, sucking slut. Last night Mistress Emily had her young pussy creampied and filled up by multiple cocks and their massive loads of cum. Her slave's cock is completely worthless locked in chastity but his mouth can be put to much use. He will never get to fuck her pussy with his locked cock as the best he will ever get is cleaning load after load out of her young cunt. Mistress Emily orders him to stick out his tongue and begin fucking the cum out of her dripping pussy as she grinds away on her queening throne. He is a very obedient slut boy and licks and sucks every load out of her cunt but that just isn't enough to please a greedy Mistress. She straps a dildo to the sluts face as she want's to ride another big cock but his caged dick will never be worthy no matter how hard it tries to get. Mistress Emily slams her cunt on the slave's dick face giving him an up-close and personal experience of what it looks like to see a big cock fucking her holes. He begs to have his cock set free and used but she keeps him in his place as a cuckold bitch where he will always belong. No amount of begging will ever set his caged cock free as any time Mistress Emily want's to ride a dick she will just strap one to the sluts face. He is the perfect cuckold fuck toy to keep locked away in her dungeon to clean up her creampied pussy every morning, day and night.

Good boys get rewards in the House of Goddess Eliza and that reward is a big, thick cock in your ass. She wants to see her bottom bitch always smiling and happy when a cock is sliding in and out of his fuck-hole. Her slave will learn to love getting fucked as that is the only way he will be receiving any pleasure from here on out. His cock has been permanently locked and sealed away making sure he grows to love his reward as much as Eliza loves deep dicking him.

Enter the strange and twisted world of chastity prison.

School rumour has it one of the girls is wearing a chastity belt enforced by her parents. After bullying and humiliating her the girls are given a taste of there own medicine by the head master.Inspired by my recent trip to Japan and manga anime comics drawn by Mikoshiro Nagitoh this video explores the school girl fetish, Chastity belts and punishment humiliation with a twist of manga.

Mistress Diana's slave is right where she left him with his ass completely exposed and vulnerable for the taking. He remains locked in very restrictive device bondage leaving him defenseless to any dick she wants to fuck him with. There is nowhere for her slave to run as she grabs a hold of her thick strap-on cock and slides it deep into his slutty hole. She has trained her filthy boy to love the feeling of a dick sliding in and out of his fuck-hole now that his cock is locked in chastity. He begs for it deeper, harder, and faster which is exactly the sweet words she wanted to hear from the slut. Mistress Diana pounds his helpless hole with all her might until his ass is stretched out and ready for the next size up. Cocks will only get bigger from here on out as Mistress Diana turns him into the size queen he was born to be.

Mistress Diana Grace proves to her slave that he doesn't need to breathe when he is servicing her sweet holes. She sits on her slave's face making him suffocate deep between her ass cheeks while making him put his mouth to work. His chastity swells to the extreme from being helpless under his Mistress's ass but that only turns her on that much more. Mistress Diana takes great delight in feeling her slave kick and squirm as he gasps for air while trying to prove his worth. The best way for any man to learn his place is by being smothered under a big, beautiful ass until he is completely out of breath and unable to do anything about it. Only then will he know how helpless he truly is when in the presence of a Dominant Woman.

Welcome to the House of bizarre.The House of Bizarre starring Devine Succubus, Coal and Quinn. After replying to a job ad (Coal) for a live-in housemaid. Coal quickly discovers his new life as a Sissy chastity maid is much harder than expected. Locked up in steel, feminised and punished for the simplest misinterpretation. The House of Bizarre explores domination, feminisation, sissy, crossdressing, makeup, chastity belts, discipline, humiliation, pet play.

Goddess Demi really wants to give it extra hard to her slave and straps on her meanest and thickest black cock she owns. She shows absolutely no mercy on his slutty ass as she rams it in extra deep making sure he won't be walking straight for a very long time.

Nurse Daphne has a patient strapped down tight ready to undergo her anti-breeding program. Men that are admitted to her un-orthodox clinic have been deemed unworthy to bring anyone into this world. Their Wives, Girlfriends or Mistress's drop them off to Nurse Daphne to have every single one of their sperms completely destroyed. Using her full-proof technique of having the man's cock, balls and ass-hole filled electricity is exactly how she burns away the last of his manhood. Once they have been strapped down and filled with high powered electrical voltage for 24/hrs he will never be the same man again.

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.

It's been a few months since Amazon Goddess Damazonia has let her slave cum. She is feeling extra generous today and allows her chastity slave to release all that built-up semen. There is just one catch...He must stay locked in chastity if he wants to be rewarded with an orgasm.

Mistress Damazonia doesn't want her fuck-hole to run away from her giant dick so she strings him up like a piece of meat. Now he must embrace every inch of her big, fat cock with no chance of being able to escape the dick. Damazonia turns him into nothing but hole to destroy as she mercilessly stretches out his ass until she is pleased with her sluts progress. Her goal of breaking him down and transforming her puny slave until a gaping fuck-slut is almost complete.

Freshmen Brat Princess Crystal enjoys humiliating the sorority cuck. In this clip, Crystal has “failure” lick her shoes and worships her feet. She writes humiliating things on its face and laughs. She thinks it's funny. The poor sorority cuck is completely humiliated by the giggling laughing 18 year old freshman. She makes fun of the mini birdlock chastity tube she makes him wear for his own good. She brags about how all the other girls are going to be trying on bikinis in front of him and then shove his face in the toilet. At the end Crystal stands triumphantly on the cucks chest as she looks at herself in the mirror.

A mysterious spy just recently tried to break into the Chastity Prison and was caught trying to steal some confidential files and inmate records. Who does she work for? And what is it that has driven her to attack such a dreaded institution? The strikingly beautiful criminal mastermind, clad in tight, shimmering latex, refused to tell us anything....Cobie, a former inmate of the chastity prison, is now an agent trying to work against the organisation. Her gambit did not pay off and to her horror, she is once again a slave to the system of Chastity, and this time they will make sure she never escapes or tastes freedom again. Armed with a new chastity device and shock collar, she presents the highest security risk and is held accordingly. Cobie tried to get the secrets of Chastity Prison out in the open, now, once again she will experience the tormenting secrets and bondage this feared institution has to offer...