Extreme Painful Caning

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Cheyenne Clitoris Disciplined with Ejaculations and Mean Iron Bondage!

Cheyenne Nub is no stranger to Implement..

Added: 2025-05-11 Rating: n/a

Enduring Together

Holly and Jeze have one goal to complete today,..

Added: 2025-05-07 Rating: n/a

Kate Kennedy is Demiralized in Extreme Restrain bondage and Made to Spunk

Kate begins in a violent predicament bondage..

Added: 2025-03-16 Rating: n/a

The soldier

ThePainFiles is by far the most frantically..

Added: 2025-02-07 Rating: n/a

Disciplined at work

ThePainFiles is by far the most insanely..

Added: 2025-01-25 Rating: n/a

IR - Mona Wails - Pretty Platinum-blonde Mona Wales, OT

Mona Wales is an accomplished player. We like..

Added: 2025-01-23 Rating: n/a

Smallish Sex Gimp Isabella Lovely Ball-gagged and Smashed in Taut Cable Restrain bondage

diminutive lovemaking kitty Isabella Uber-cute..

Added: 2025-01-19 Rating: n/a

Devasting Torture And Extreme Suffering!!!

Ashley has every look that makes you think that..

Added: 2024-12-04 Rating: n/a

Disciplined with Ejaculations and Mean Iron Bondage!

Cheyenne Joy button is no stranger to Device..

Added: 2024-11-30 Rating: n/a

Serena Blair Restricted and Made to Cum in Rope Restrain bondage

Serena Blair is a classic, petite HogTied model...

Added: 2024-11-19 Rating: n/a

Intercourse of Bondage & discipline Players Teach Ass fucking Submissives to Boink and Serve

The Upper Floor hosts its messiest Domination &..

Added: 2024-11-04 Rating: n/a

Magnificent Ache Mega-slut in Extreme Bondage, Tormented, Penalized

Ingrid has an amazing all congenital body, likes..

Added: 2024-10-05 Rating: n/a

Sex of Domination & submission Players Instruct Buttfuck Submissives to Nail and Serve

The Upper Floor hosts its dirtiest Sadism &..

Added: 2024-10-03 Rating: n/a

Hook-up of Domination & submission Players Teach Assfuck Submissives to Fuck and Serve

The Upper Floor hosts its muddiest Domination &..

Added: 2024-07-27 Rating: n/a

Ariel Anderssen Lengthy Term Horse Dame Teaching pt.2

The next thing she knows she wakes up in a bed,..

Added: 2024-02-28 Rating: n/a

IR - A Tremble - Young Hottie Grace West

Nip rings are a give away that a nymph is into..

Added: 2023-09-24 Rating: n/a

IR - The Shiver - Pretty Chick Grace West and OT

Nipple rings are a give away that a doll is..

Added: 2023-08-24 Rating: n/a

Lystra - Flow

With sensitive face and diminutive body, Lystra..

Added: 2022-11-28 Rating: n/a

IR - Rain DeGrey - The Booty Trauma

I've spoke a bunch about the lovely Rain DeGrey...

Added: 2022-02-17 Rating: n/a

IR - Bonnie Day - A Bonnie's Culo

Bonnie Day and O.T. are having a perfectly..

Added: 2022-01-27 Rating: n/a

Flying Inverted Category 5 Skull Poke

The outstanding Cassandra Nix comes back to..

Added: 2022-01-16 Rating: n/a

Calipig - Part 1 - Calico

Calico’s primary perversion was to endure ache..

Added: 2021-11-27 Rating: n/a

Yui Misaki - Torture Apartment

This series requires realistic spectacle and..

Added: 2021-11-10 Rating: n/a

IR - The Culo Trauma - Cyd Black and Rain DeGrey

I've spoke a bunch about the lovely Rain DeGrey...

Added: 2021-10-14 Rating: n/a

HT - Sheer pleasure Bi-atch - Redhead Cici Rhodes

Cici Rhodes is a tall gangly ginger-haired that..

Added: 2021-09-07 Rating: n/a

IR - The Ass Trauma - Cyd Black, Rain DeGrey

I've spoke a slew of about the lovely Rain..

Added: 2021-08-05 Rating: n/a

IR - The Bonnie's Arse - OT and Bonnie Day

Bonnie Day and O.T. are having a perfectly..

Added: 2021-07-19 Rating: n/a

IR - Rain DeGrey - Arse Trauma

I've talked a plenty of about the lovely Rain..

Added: 2021-06-05 Rating: n/a

Intotheattic - Starlet 2009Dec17

Next Iris finds herself getting prepped for a..

Added: 2021-05-08 Rating: n/a

Failure Pudding Part 1 , Nora Riley

Nora Riley is known to be pretty respectful and..

Added: 2021-03-29 Rating: n/a

Weekend Londons Part 5 , London River

London Sea is at lengthy last well-prepped to..

Added: 2021-03-29 Rating: n/a

Devilynne-The Calling

Devilynne is rambling around a fresh..

Added: 2021-03-26 Rating: n/a

RTB - Rain DeGrey and PD - La Cucaracha Part 3

There's nothing like witnessing the finale of a..

Added: 2021-03-20 Rating: n/a

Night24 Part 333 - Extreme, Bondage, Caning

Matt provides her with a ball gag and a eye mask..

Added: 2021-01-04 Rating: n/a

HT - The Fantasy Realized - Emma, Elise Graves

The Princess of Pain Elise Graves leads Emma..

Added: 2020-11-19 Rating: n/a

RTB - La Cucaracha Part Trio - Rain DeGrey

There's nothing like seeing the finale of a RTB..

Added: 2020-11-10 Rating: n/a

RTB - Rain DeGrey, PD - La Cucaracha, Part Trio

There's nothing like witnessing the finale of a..

Added: 2020-09-23 Rating: n/a

HT - Deep Facehole - Violet Monroe and Jack Hit

Violet Monroe has her desires predominated by..

Added: 2020-09-22 Rating: n/a

Sierra Groans - Sierra Cirque- Matt Williams

Matt Williams has has a lengthy week, all he..

Added: 2020-09-22 Rating: n/a

IR - yes, Yes, YES! - Winnie Rider

Winnie Rider enjoys pussy torture. I'm not sure..

Added: 2020-09-19 Rating: n/a

IR - A Bonnie's Donk - Bonnie Day, OT

Bonnie Day and O.T. are having a flawlessly..

Added: 2020-08-21 Rating: n/a

HT - The Dream Realized - Emma and Elise Graves

The Goddess of Ache Elise Graves leads Emma thru..

Added: 2020-07-23 Rating: n/a

Perfect Sluts Broken & Punished

A beautiful, big-titted blonde like Rain DeGrey..

Added: 2020-06-22 Rating: n/a

IR - Iona Grace and OT - The Subject 146

“Wake up, Subject 146. You will now begin your..

Added: 2020-06-10 Rating: n/a

IR - Ass Trauma - Rain DeGrey, Cyd Black

I've talked a lot about the lovely Rain DeGrey...

Added: 2020-06-10 Rating: n/a

HT - Blaze-in Bondage - Jack Hammer, Marley Blaze

Lots of women just fall apart once they've had a..

Added: 2020-05-26 Rating: n/a

IR - Bonnie's Butt - Bonnie Day, OT

Bonnie Day and O.T. are having a perfectly..

Added: 2020-05-18 Rating: n/a

HT - Violet Monroe and Jack Hammer - Deep Throat

Violet Monroe has her dreams dominated by..

Added: 2020-05-06 Rating: n/a

Ass Up, Mouth Out

At 19 years old Cassandra Nix is as cute as they..

Added: 2020-04-16 Rating: n/a

Never-Ending Orgasms Make Pain Sluts Cry

Rain DeGrey says she loves to be challenged..

Added: 2020-04-16 Rating: n/a

Creamy Cunt Part One , Bronte

Her wrists, ankles, and neck are cuffed to a..

Added: 2020-04-15 Rating: n/a

Stocked Slut Part One , Sybil Hawthorne

Maybe sometimes he wonders why he likes to hurt..

Added: 2020-04-15 Rating: n/a

In a Bind Part Two , Kali Kane

In part one, PD mindfucked Kali to the max as a..

Added: 2020-04-15 Rating: n/a

Shocked Slut , Lavender Rayne

A metal rod fills her cunt. It's wired. He..

Added: 2020-04-15 Rating: n/a

HT - The Blaze-in Bondage - Marley Blaze and Jack Hammer

Lots of women just fall apart once they've had a..

Added: 2020-04-13 Rating: n/a

Cunt Hole , Arachnia Web

She's packed into a cage in a painful kneeling..

Added: 2020-04-11 Rating: n/a

Doll Face featuring Mya McKay

Tattoos on the backs of her fingers read DOLL..

Added: 2020-04-11 Rating: n/a

Processed featuring Erika Kole

Gravity plus mass plus steel equals a vicious..

Added: 2020-04-10 Rating: n/a

Ms. Hercrack featuring Hollie Stevens

The Grand Inquisitor sits at his desk. The..

Added: 2020-04-10 Rating: n/a

She Rides featuring Star

A true professional, Star suffers for PD. She is..

Added: 2020-04-06 Rating: n/a

HT - Redhead Violet Monroe, Jack Hammer - Deep Throat

Violet Monroe has her dreams dominated by..

Added: 2020-04-06 Rating: n/a

Freedom in Pain Part Two

Whips and canes get so much worse when..

Added: 2020-03-24 Rating: n/a

Please and Thank You

Instead of me getting pleasure I like other..

Added: 2020-03-23 Rating: n/a

Screamer

It's all about Ashley Lane's amazing body today...

Added: 2020-03-03 Rating: n/a

Sexy Bdsm Subject

“Wake up, Subject 146. You will now begin your..

Added: 2020-03-03 Rating: n/a

Yes, Yes, Yes!

Winnie Rider likes pussy torture. I'm not sure..

Added: 2020-03-02 Rating: n/a

Purple Rain

Today we have the beautiful Rain DeGrey on hand..

Added: 2020-02-27 Rating: n/a

Ass Trauma

I've talked a lot about the lovely Rain DeGrey...

Added: 2020-02-27 Rating: n/a

Compliance Part 2

What can I say about Cherie DeVille that her..

Added: 2020-02-27 Rating: n/a

Queen of Pain

What makes Elise Graves our Queen of Pain? It..

Added: 2020-02-22 Rating: n/a

IR - Rain DeGrey and Cyd Black - Ass Trauma

I've talked a lot about the lovely Rain DeGrey...

Added: 2020-01-01 Rating: n/a

Scream Test Part II - Elise Graves

Elise's journey into the depths of pleasure and..

Added: 2019-12-11 Rating: n/a

Rain Degrey

RealTimeBondage exists because there is no other..

Added: 2019-12-07 Rating: n/a

RTB - La Cucaracha Part 3 - Rain DeGrey, PD

There's nothing like seeing the finale of a RTB..

Added: 2019-11-13 Rating: n/a

Explosion - Lystra

With mushy face and diminutive body, Lystra..

Added: 2019-11-08 Rating: n/a

Bonnie Day - Bonnie's Butt

Bonnie Day and O.T. are having a perfectly..

Added: 2019-09-28 Rating: n/a

Simmered Suffering

When we get started on Nikki Darling she thinks..

Added: 2019-09-25 Rating: n/a

Devilynne-The Calling

Devilynne is strolling around a new..

Added: 2019-09-24 Rating: n/a

HT - A Sensation Slut - Cici Rhodes

Cici Rhodes is a tall lanky redhead that clocks..

Added: 2019-09-22 Rating: n/a

Mei I have More

Mei is a masochist. If she could beat herself..

Added: 2019-09-22 Rating: n/a

Squirting Fountain

When cumming makes you squirt a river you have..

Added: 2019-09-21 Rating: n/a

Screamer , HD 720p

It's all about Ashley Lane's amazing body today...

Added: 2019-09-20 Rating: n/a

Compliance Part 2 - HD 720p

What can I say about Cherie DeVille that her..

Added: 2019-09-18 Rating: n/a

Scream Test Part 1 , HD 720p

Elise Graves reaches new heights of pleasure and..

Added: 2019-09-18 Rating: n/a

Purple Rain , HD 720p

Today we have the beautiful Rain DeGrey on hand..

Added: 2019-09-18 Rating: n/a

Ass Trauma

I've talked a lot about the lovely Rain DeGrey...

Added: 2019-09-18 Rating: n/a

Kunt Log part 2

Clad in head-to-toe white like an angel awaiting..

Added: 2019-09-04 Rating: n/a

Jingle Sluts Part 2 - Cadence Cross, Nikki Darling

Cadence Cross is still looking for more from her..

Added: 2019-07-28 Rating: n/a

Scream Test Part II - Elise Graves, Cyd Black

lise's journey into the depths of pleasure and..

Added: 2019-07-27 Rating: n/a

RTB - La Cucaracha, Part 3 - PD and Rain DeGrey - HD

There's nothing like seeing the finale of a RTB..

Added: 2019-07-25 Rating: n/a

Rain DeGrey, Ashley Lane

Broken Blonde Part 2 A beautiful, big-titted..

Added: 2019-07-18 Rating: n/a

Broken Blonde , Part 2

A beautiful, big-titted blonde like Rain DeGrey..

Added: 2019-06-26 Rating: n/a

Kunt4Sale Rain Degrey

RealTimeBondage exists because there is no other..

Added: 2019-06-19 Rating: n/a

Jingle Sluts , Part 2

Cadence Cross is still looking for more from her..

Added: 2019-06-19 Rating: n/a

Confessions of a Greedy Slut , Part 3

Cherie DeVille isn't even close to done with her..

Added: 2019-06-18 Rating: n/a

Trial by Fire

Cici Rhodes is about to experience the most..

Added: 2019-06-18 Rating: n/a

Trial by Fire , Part 2

For just a few minutes Cici Rhodes was telling..

Added: 2019-06-18 Rating: n/a

Penny Dreadful , Part 3

Penny Barber and Mollie Rose are two sides of..

Added: 2019-06-18 Rating: n/a

China Doll , Part 3

There is time honored torment that is..

Added: 2019-06-17 Rating: n/a

Caned Lane - Hard Bdsm

Watching Ashley Lane get off is a thing of..

Added: 2019-06-14 Rating: n/a

Meat and Potatoes

Sasha doesn't masturbate. When she's at home and..

Added: 2019-06-12 Rating: n/a

Cant Stop

Rain DeGrey told me everyone has their specific..

Added: 2019-06-11 Rating: n/a

The Sweetest Kiss , part 2

What a wonderful gift I found upon entering the..

Added: 2019-06-11 Rating: n/a

Crybaby , Hard Bdsm Action

Simone Sonay said she loves to be tied down and..

Added: 2019-06-10 Rating: n/a

Back for More Part 3 , Nikki Darling

In the third and final installation of Nikki..

Added: 2019-06-08 Rating: n/a

Weekend Londons Part 5 ,London River

London River is at long last ready to finish her..

Added: 2019-06-08 Rating: n/a

RTB - Winnie Rider, Amy Faye - Winnie the Hun, Part 2 - HD

All suspensions are brutal but there aren't many..

Added: 2019-05-15 Rating: n/a

IR - Ass Trauma - Rain DeGrey

I've talked a lot about the lovely Rain DeGrey...

Added: 2019-05-13 Rating: n/a

Bella Rossi , Matt Williams

Oh, Bella Rossi is one hell of a beauty, and she..

Added: 2019-04-23 Rating: n/a

Just a Whore- Lauren Phillips

This languishing torment is like brainwashing..

Added: 2019-04-19 Rating: n/a

IR - Ashley Lane and OT - The Screamer - July 25, 2014 - HD

It's all about Ashley Lane's amazing body today...

Added: 2019-04-16 Rating: n/a

Kay Kardia, London River-Cunty Part 2

We'll get back to Kay Kardia in just a second..

Added: 2019-04-15 Rating: n/a

Abigail Dupree-The Extended Feed of Miss Dupree Part 5

You would think that after all of this time we..

Added: 2019-04-13 Rating: n/a

The Extended Feed of Miss Dupree Part 3

We've done water torture before. It's one of the..

Added: 2019-04-13 Rating: n/a

Syren De Mer, Matt Williams-The Art of Suffering

Suffering is almost as much of an art form as..

Added: 2019-04-11 Rating: n/a

Simmered Suffering- Bdsm , HD 720p

When we get started on Nikki Darling she thinks..

Added: 2019-04-10 Rating: n/a

Harley Ace-Bind-her Clips

Harley Ace is a crier. OT LOVES criers. They..

Added: 2019-04-09 Rating: n/a

<b>caution:</b> extreme bdsm and ass-fucking with ariel x

Scene 1 Arms strapped to a cold metal pipe..

Added: 2019-04-07 Rating: n/a

Krysta Khaos Is Locked Down , Fisted Hard

Krysta Khaos describes herself as a huge pain..

Added: 2019-04-06 Rating: n/a

The Sweetest Kiss, part one

Mira Raine sat on my table and told me that her..

Added: 2019-04-02 Rating: n/a

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