Mistress Isabelle loves to own sissy boys as she knows they are much more in-tuned with the female body. Sissies will always work their hardest to please their Mistress as they are never selfish when their cock is made useless by the form of strict chastity. Mistress Isabelle unlocks her sissy from its cage and put's the bitch's whore mouth to use. If her sissy does a proper job and makes his Mistress cum all over his face then a big, fat cock will be waiting to use the bitch boy's fuck-hole.

Officer Deltore has been making her rounds all day and sweating profusely in her pantyhose. She could use a little relief and has just the prison bitch-boy to give that to her. He has been beaten down to be an obedient bitch and finally knows his place as Officer Deltore's toy. She unlocks the prisoner from his cage and uses her pantyhose covered ass and pussy to smother his face making sure she gets a proper orgasm.

Shock collars have an extraordinary ability to transform the most unruly to the most subservient with just the push of a button. Officer Isabelle Deltore has her bitch right where she wants him now that he is under her strict control. On his knees, locked in chastity and licking her pussy for the rest of his house arrest sentence.

Kade is under strict house arrest but can't seem to obey the rules of his probation. Correctional Officer Isabelle Deltore makes an unexpected visit to send him back to the big house. He begs and pleads to Isabelle for one more chance willing to do anything and everything to not be sent back. Using her high voltage shock collar she puts the bitch in his place making him become her personal doormat. He will worship, lick and adore her beautiful feet just the way she likes for him get back on her good side. Kade quickly learns she means business as she shoves her toes deep in his mouth making him gag for forgiveness while shocking him into obedience.

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.

Mistress Isabelle needs to show her sissy just what it's like to be fucked by a big, fat cock before she sends him out to the real boys. She bends his tight ass over and slides her big, strap-on cock deep in his fuckhole. There is no escape for her sissy from a life filled with dick as Mistress Isabelle fills him up and gives him the ride of his life.

Mistress Isabelle is going to train that clitty of yours to cum just like a bitch. She has extra pinky sissy lingerie picked out just for you to dress up in and become her sissy slut doll. Now be a good girl and burn all those boy clothes as from here on out you will only wear pink. You will only cum when given permission and you will always be on your knees with your mouth wide open. Good girl! Now show your Mistress how you touch that clit stick of yours in that pair of soft pink panties...

Goddess Isabelle Deltore takes complete control of your cock giving you a 1-on-1 lesson in edging yourself to new heights of sexual exploration.

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.

Kade is about to find out Correctional Officer Isabelle Deltore means serious business and won't tolerate any more house arrest rules to be broken. If he fucks up even once more it won't be just her big, thick cock being shoved and plowed deep inside him. To help with his obedience training a shock collar has been locked tightly around his neck so he can be quickly and efficiently corrected at the push of a button. His cock remains locked in chastity but his asshole is completely exposed and vulnerable to be punished with her merciless strap-on dick.

Officer Deltore has a growing suspicion that her captive prisoner is smuggling something deep inside his ass. She spares no time and straps on her anal probing cock to find out if the bitch has anything to hide.