Painful Chastity Clip Fuck

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His pain is my pleasure ;) (HJ33-9)

New anal only chastity video! EvilKitties

Painful Cumming in Chastity

Bound with EStim urethral plug, giving him some pained release.

Dominant Wife Locks Slave Husband Up In Chastity

Pain is pleasure

This morning was painful ?

If you managed not to cum, you would've get two weeks of freedom from chastity!

New girlfriend got a bit carried away while filming… (sound on to hear how much fun she’s having and how much pain I’m in)

Small key hanging betwen my breast... All I need to control you cock, cum and cause you pain

He Thinks His Blue Balls are Going to PoP in Ball Crusher! But I know They Can Take More Pain for Mistress Loow. 😈

And I hope it's painful 😈

A little pain with our pleasure this evening. [m]

This will be serious, painful and very educational!

Most underestimate the level of pain a hard cock in a spiked cage can produce!

Squirming and moaning in pain while slapping my full balls.

The Doxy is the most pleasurable pain, for a slut in chastity ? [domme]

A little chastity acceptance training… If he asks to be let out he pays a painful price 😈

Starting our adventure down cbt, remind him I own his pain and pleasure

Flattening his Blue Swollen Balls in Chastity Cage with all my weight between Seat While my Parents are Home… I hope they did not Hear us since he Did Not Shut Up about his Stupid Painful Balls.

alls in Metal Crusher While he Stays in Micro Chastity Cage for our Pleasure!

Throwback to when pain and pleasure were the same

Its time for a game of pleasure or pain. Roll an even number and get pleasure. Odd equals pain. Full 12 minute game on OF!

Pain Slut said he wanted to use the Vibrator on his Small Chastity Cage because he has Bad Blue Balls so I Crushed them with All my Weight in between the Toilet Seat and allowed him to use the Vibrator. 😈 I am so Nice to my Pain Slut. 😇

Day 5 of Locktober! 🔒 Using my New Strong Ball Crusher on Pain Slut’s Swollen Blue Balls!

I allowed him to Worship my ass While he is Locked in Small Chastity Cage but I want his balls in between the Toilet Seat with all my weight as I smother him in my Ass! 🍑🚽💦😈

Sissy in small chastity

I'm not sure what was more painful. The ruined handjob or the overstimulation afterwards. This was after a month of chastity 😭😭

No release for you, only a painful tease...

these were painful

I left town for a few days and came back to this 👿. His balls are in for a world of pain 👊 sorry hubby. You brought this on yourself 😜

Pain is always a pleasure to give- and one my sub will eager accept if I'm sitting on their face!

She gives you pleasure and pain!

I have been getting more and more desperate after a while in chastity, so when my hole isn't ready, I start harshly kneading my balls, it's painful, but it does quench the thirst, and it's the closest I can get to touching my clit

Cute skinny tranny locked in chastity gets her asshole torn apart with massive cocks.

[💜OF] i used to feel pain but now i just feel pleasure!

Bondage, Chastity, Punishment and beautiful clothed Mistress

I don't care if it's painful, I'm still going to tease you!

My GF said she loves hearing me moan in pain while trying to escape the chains I'm locked in. She told me the sound of me suffering turns her on... [CD]

All locked and denied..would you give my sensitive nipples teasing pleasure or clamping pain

I don't know what made me moan more. When my GF teased me with her hands or the pain of the super tight armbinder

My Small Cock Coming Out Of A Chastity

Banana BallBusting Hard Mistress Loow and Pain Slut

After I tortured his pathetic prejac , we went out walking for hours. Should have seen him hide the pain!😂 Back home it took him another 45min to get 'em back out bc the lock stays closed. 🔒😜

A little bit of pain always makes my boy’s cock throb in the chastity cage 😉

Cucky’s balls aren’t completely useless! I can use them to add a little physical pain to the mental pain of watching me fuck a real man.

NEW FULL VIDEO - My caged leather gimp is subjected to pain and denial

I tried asking out of my cage and my Mistress made me go through a series of humiliating and painful tasks in order to try and persuade her😖, it didn't, but still had to lick all of her feet and treat it as the huge privilege it was 😣.

28 (Finland) #Helsinki / Pori Chastity Sissy Slut

A little teasing before a painful session

I wanna see how hard you’re trying to endure the painful coldness😈🧊

Ball Crusher Waffle Balls: A Deliciously Painful Treat - Natalia Vega

Sorry I'm a little late to locktober but finally painfully locked and pinched my pathetic clit into chastity

My little cock started peeking through my chastity belt, so I showed it what happens if it tries to escape!

Pain is a treat. So i treated my good girl to it

Hubby's balls or better said my tiny little stress balls 🤭 It's fun slapping them around and see them bounce back and forth. Even though hubby is in obvious pain, he let's out such naughty little moans. I guess he likes it too? 🤭

Watch closely what you’re missing out on because from here, pain will be your pleasure

It's surprising how much pain you can inflict with a flick!! Sitting on his face and Flicking balls in a cage

In the medical room, pain and denial is pleasure

Chastity GIF by vigarlunaris

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