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I Had a Huge Prostate Orgasm while Standing in Chastity

You are not unable to cum from anal. You just haven't been fucked hard enough yet.

Caged and cumming with prostate massager

Grab her cage for full control

Newbie chastity sub goes wild during prostate milking procedure [hismith dildo]

Chastity student instructed to sit impaled on the Sybian for 20 min. Purpose of this test is to check his behavior during the most intense way of prostate stimulation while I am making him orgasm 15 times -Institution X-

bought this cage to include into some of my vids, second time trying it out

Tenga egg, chastity cage and prostate massager is definitely nice combination. He was really close to cumming but somehow managed to keep it in, second time he couldn't and got ruined ? Remember to check comments ?

Chastity Electric Electro Femdom Fuck Machine Machine Prostate Massage Sex Machine Torture gif

The longer I am in chastity the more i want a dick inside me. 😉

Institution X: Chastity student restrained for anal endurance training while his cock is being electrocuted. This procedure is preprogramed and he will have to endure it until the end no matter what.

ESTIM buttplug chastity and pads. NO STOPING NO MERCY Pure hell but he has to take it as a punishment for being caught masturbating

Chastity Edging Electric Electro Prostate Massage gif

This is how students get trained and prepared for anal. Inflatable buttplug is inserted inside his asshole and pumped more and more to stretch his hole while ESTIM chastity power is gradually being increased making him go wild. 🖤INSTITUTION X🖤

Student gets anal stretching training while ESTIM intensity is gradually being increased on his chastity 🖤INSTITUTION X🖤

Chastity student gets trained by machine at Institution X

She tried to help at the end 🔐

Tasty squirt in chastity with njoy (sorry for out of focus 😩)

Our mission at Institution X is to make every male cum from anal prostate stimulation. This is superior way to cum producing stronger, longer orgas...

Sub is instructed to get on the Sybian and position himself so the insertable part is in his asshole right against his prostate. If he fails this chal

Chastity Machine Prostate Massage Sissy gif

Chastity is the only way your gonna learn sissy..

🔥Once you try anal you will never go back😃👍 After he reached orgasm the begging started. Yea, he was begging me for more. I gave him more with pleasure. He came 4 times during this session.

Freaky Dominant GILF Lillian Tesh Prostate Play Session

What do you think… does my slave deserve to cum?

THE BEST FEELING IN THE WORLD🔥 Chastity student is restrained and machined brutally until he reaches anal prostate orgasm. Moaning, shaking, goosebumps... Perfection!!!😏Who wants to cum like this? 💦💦

When a man curls his toes and shakes his feet while he's getting anal prostate stimulation you know it's fucking good!🔥😈🔥😉

Did I do it right?

Some fun with a tiny wand, conductive chastity cage combined with e-stim device and thick vibrating plug 💦

ESTIM Chastity Anal Training At INSTITUTION X

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Behavior Test For Horny Chastity Sub. FUCK MACHINE 0-MAX. Rate Him 1-10😉

I spilled half of it =(

All this chastity wearing is finally paying off 🤤

Fucking Machine Prostate Milking 4 Orgasms Hands-free Restrained

This sex machine makes my climax last forever. I'm addicted.🥵🤪🤪

I have unlocked self-milking

Restrained Merciless Prostate Edging for Load Buildup

Anal in random parking lots turns me into a squirter.

Prostate milking in chastity

Chastity Prostate Massage Sissy Porn GIF by boneshooter9

The only way subs are allowed to get a release. Once he decides that he cant take no more teasing he has to press the button and our assistants will bring him to this room and prepare him for the milking in front of the supervisor (read comment for more)

And once sub releases his load our assistants will take him back to his cell, restrain him and start teasing him again and driving him crazy until the next shift rives. ---Institution X---

Locked in chastity, come goon to sissy hypno with me bud

Used a prostate massager on Luke. Worked a little too well, but we had a great time 😊Story inside

Daily routine of my cuck

Chastity and prostate vibration

The only type of pleasure chastity boys get! 🙂

The perfect orgasm for my slave 💦🔐

My aneros butt plug makes my caged clitty squirt prostate fluid through my panties SO MUCH

Getting the front and back massaged

That shot further than I expected

This beta deserved to cum today. Want some of this too?

Chastity Cock Milking Fountain

Pressed on his prostate while he was locked up

Anal Vibe + Chastity = ❤️

Milking it out properly 🥛💧

How to orgasm in chastity

Chastity GIF by hotwifenatalie

Fucking My Clipped Clitty 🥰