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Dee Williams in extreme bondage

Casey Calvert endures bondage, wearing a dental retractor

Alien Cartoon Electric Electro Fuck Machine Pain Sadism Screaming Tentacles Whipping Porn GIF by slimyalien

Sir likes to take a video of my face during our sessions and keep note of which parts of play were the most painful

I give him pleasure and he gives me pain, fair trade - wouldn't you say? The best part about it is I never know what's coming because of the lenses!

Decorating the Slutmas pain tree with hot lights crotch rope, heavy bells on nipple piercings, and bows stapled into its flesh.

I Just Love That Reaction When Their Pussy Is Too Sensitive After Cumming Too Much. When Pain And Pleasure Are One In The Same

I was surprise by the intense pain. I totally lost it and burst into tears. [F] [M]

Squirming in Pain and Pleasure

Butthole whipping + anal insertion = screaming pain

Sir likes to use my latex thong to whip my asshole before inserting my anal hook for maximum pain. (Sound on)

BDSM BBondage Fetish Gagging India Summer James Deen Pain Slave Submission

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

i love when the real pain comes in a moment ~after~ the impact

Relief before some Pain

Gia DiMarco hangs by her wrists until she whimpers in pain, only to be lowered back onto the wooden horse

[Amy_Ink] Pain Of The Day 😈⚡

Emerald's Pain Slut Training (Full video in comments)

[F] Some pain and pleasure with Daddy [M]. I definitely made some fun sounds during this session 😅 (Click redgif for sound)

Me and Elizabeth Thorn each trading off pain and pleasure by Royjack during movie night ❤️💦

Pleasure is always better with a little pain [F][M]

told to wear a skirt over it to run errands, every move to remind me painfully of my place.

College rope bunny cumming hard in painful predicament bondage

Bobbi Starr squeals in pain as she's forced to walk the crotch rope

Bobbi Starr squeals in pain as she's forced to walk the crotch rope

Make me WET with my PAIN😍

Jessie Cox gets trained to handle the pain

She's in a little pain

[Amy_Ink] Playful Pain Tongue🍭🤪

[Amy_Ink] Master my delicious Pussy is craving for pain🥵💛

Hypnotized my slave to only feel pleasure from pain - and make her cum that way

Anal Hook Atomic Wedgies! Pain, Pleasure, and Humiliation!

Genesis Fae strapped to bondage table and made to orgasm [F][M]

I love struggling against the pain

Here's the full video with sound of this painful experience. This stopped me from bratting for a few days.

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

If you feel like you are in a spot, here is some predicament bondage to lighten up your day [M][F]

Sometimes pain is the only way through.

Literal burn or muscle pain burn? Tough choice :o

Lorelei Lee knows she has to bear the pain in order to have the pleasure of an orgasm

The only way to get some relief on my nipples was to pull down hard on the rope tied to my collar - I had to choose between pain and choking! [F]

Keeping the rock filled buckets level to save her nipples from the wire-connected clamps. Her tight bondage makes it all the harder when she's unable to stop the distracting vibrator or rest her outstretched arms.

Forced between a slow strangle or sensitive pain, with no freedom for a moments rest.

She broke quicker than she thought when the whip came out, her cute whimpering cries a mixture of disappointment and pain.

Sasha Grey locked in metal bondage and screaming from multiple orgasms (sound on!)

Sasha Grey completely loses her mind while locked in metal bondage and vibrated into multiple orgasms (Sound on!)

Learning to control her screams of pain

Bonding through pain and denial...

Rough Femdom Bondage Ballbusting

The Pope: "We're gonna find out how good you are with anal, and how good you are with pain while you're getting anal."

My little pain slut. The harder I go, the harder she cums.

Does the pain in my nipples stop me from cumming...? Watch with sound to find out!

At least he’s at the beach [public] [bondage] [handjob] [exhibition]

For the first time in a while master [f]illed his dumb whore's cunt with a toy, but not without making its clit and nipples throb in pain

Breaking a slut and teaching her how to beg properly to be fucked… In my opinion, Master’s dick should be earned for being a good pain slut.

oof banding and clamping is a new kind of pain that I love ofc

My fucktoy learning to orgasm with pain and pleasure

Rewiring and reprogramming a cunt to be a free use 24/7 pain slut… Zapping out all thoughts of defiance, arrogance, ability to think for self - a perfect slave in making!

Mixing pain and pleasure, depriving you of your senses. I’ll break your mind to the point it can’t think what’s going on… and your body would be so exhausted it will feel like it’s broken. You’ll truly be nothing but a broken little fuck toy!

Enjoying yourself much? Let’s decorate you with accessories, you’ll enjoy a lot more. Especially when pain joins pleasure… would tell how feeble and easy your mind is to break