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Someone was overdue for their Milking... 😈

Helena Quest Milks Cock

Slave restrained for ruthless prostate milking procedure -Institution X-

Fucking Machine Prostate Milking 4 Orgasms Hands-free

Restrained for Ruthless Prostate Milking Procedure [hismith machine]

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

Ass wiggle, prostate pulsate, cock explode

I love when my wife milks me til I explode 🔥

I want you to spend the rest of the day thinking about how good it would feel to have your prostate milked like this..

Student locked for prostate milking at Institution X

Student restrained on the Sybian and examined for behavior flaws while his prostate is getting milked and he is orgasming over and over again. 🏴Institution✖🏴

Let me bend you over and milk your prostate 💕

Fucking Machine Prostate Milking 4 Orgasms Hands-free

Maitresse Madeline Marlowe Prostate Milking Extravaganza

Njoy wand + massage gun = huge messy handsfree load

Student is moaning like crazy while his prostate is being stimulated. He is restrained and there is nothing he can do to escape until anal probe milks him completely dry and professor releases him ___Institution X

Fucking Machine Prostate Milking 4 Orgasms Hands-free Restrained 🖤INSTITUTION X🖤

The end of a long milking session!

He came like 3 times more than usual with my prostate milking[oc]

My sub gets some pain, teasing and a prostate release.

Intensely milking his prostate

Fucking Machine Prostate Milking 4 Orgasms Hands-free Restrained Femdom

Shot one hell of a load with the prostate stimulator in ;)

[OC] Admit it, you wanna be milked by like like a ketchup dispenser?

Fingering his prostate and pounding his hole drives me crazy 😍💦

Fingering his prostate perfectly prepares his ass for my big dick 😏

Ever watched a gymbro flex and milk his prostate in the same video?

Anal prostate milking is the only way chastity students are allowed to get a release. 👍

Fucking Machine Prostate Milking 4 Orgasms Hands-free Restrained

This is how we milk slaves at Institution X. Our mission is to make every man reach orgasm from anal prostate stimulation. This is the superior way to reach orgasm. It produces more powerful and longer lasting orgasms with a minimum refractory period.👍

This is how we milk slaves. Our mission is to make every man reach orgasm from anal prostate stimulation. This is the superior way to reach orgasm. It produces more powerful and longer lasting orgasms with a minimum refractory period.👍

sloppy blowjob while stimulating prostate

More twinks should be milking their prostates 😈

Its fun locating the prostate in his ass. Milked him like a ketchup dispenser.

Seducing my patient 👩🏻‍⚕️🩺 I made sure his cock was throbbing before I milked his prostate... 🩺

Fucking Machine Prostate Milking 4 Orgasms Hands-free Restrained

Chastity Sub Moaning and Growling While Vibrator is Milking His Prostate Handsfree HFO Orgasm 🙂

Fucking Machine Prostate Milking 4 Orgasms Hands-free Restrained

Anal prostate milking for chastity slaves

Intense anal probe prostate milking - 4 squirting anal orgasms💦💦

Decided to go up to the medium length of my sounding rod kit (there’s 3 of them) this one definitely hits my prostate 🤤

It’s time for your milking 😈

One more! Milking and drinking it

This is my favorite way to milk him. Can I do you next?

Cock Milking GIF by nosubstance

Chastity milking with Njoy wand

[Private] Belle Claire Ends a Hot Yoga Session With a Prostate Milking (Part 2 In Comments)

Sunday milking-

Love milking his prostate 😘

Second cumshot in a row for total milking

Nothing hotter then bending him over and milking his prostate

Loves, how come you don't come to meet me. I have had to play alone. And I have milked my prostate with my dildo. I have experienced an indescribable feeling WOW WOW WOW 😈🥵🤤

This makes him so hard! I can feel his prostate swelling to cum!

Restrained Sub Twitching Impaled on Devil Dildo until he Reaches Handsfree Anal Prostate Orgasm

Combination from HELL- Slow Prostate Stimulation + Penis Electro Edging = ORGASM THAT SHUT OFF HIS BRAIN

Only thing sluttier than wearing compression shirts is milking your prostate while wearing a compression shirt!

Bound and Ruined: Watch the Sex Machine Perfectly Hit His Prostate and Trigger a Ruined Orgasm

6 Cumshots from MILF Prostate Milking Session! [OC]

Any goonettes willing to finger my bussy and milk my goonstick

Cock locked. His body’s trembling. The machine’s hitting his prostate perfectly, and keeps him right at the edge, helpless…moaning...🙂 When your turn comes how long will you be able to handle this?