Dylan Ryan in 'Kink' One to Remember-Squirting from the Pain (Thumbnail 9)

Dylan Ryan in 'Kink' - One to Remember-Squirting from the Pain (Sadistic Rope)

Un-cut, nonstop action with brutal bondage and squirting orgasms.

Released : October 8, 2014
Tags : Bondage, Predicament bondage, Flogging, Pain, Caning, Squirting, Crotch rope, Straight, Double Penetration, Cut, Rope bondage, Domination, Submission, Bdsm, Handler, Ball gag, Fingering, Corporal Punishment, Vaginal Penetration, Humiliation

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More 'Kink' scenes from Dylan Ryan

Dylan Ryan - Under His Boot

Dylan begins in an ankle suspension with her arms stretched out to render her completely helpless. The Pope begins his assault on her flesh instantly and uses her up like the good little whore that she is. Her toned body starts to glow red as she is tormented with floggers and crops. Her pussy is tenderized before fucking it with a massive dildo. Next Dylan is locked into the scavenger's daughter, which is tormenting on it's own especially if you're tall. Then comes the nipple suction and torment, then her body is beaten with a baton. She screams and tries to get away, but the cols hard steel defeats her attempts. She is made to cum more before moving on to the final scene. She is locked into a doggy position with her magnificent ass in the air. Again Dylan is abused and tormented until she can no longer stand it, and then The Pope fucks her ass. Dylan is finished off where she craves to be most, which is under her Master's boot for her final orgasms.

Dylan Ryan in 'Squirting Screaming Orgasms and Anal Machine Fucking'

Dylan Ryan - Squirting Screaming Orgasms and Anal Machine Fucking

Dylan is no stranger to our site and as expected she is here to get fucked and squirt everywhere. After a very seductive strip tease, she lays back and tease her pussy to multiple orgasms. Next we get her set up with her first machine and within no time, she is squirting all over the studio. She is then standing over the crystal palace and as the machine increases in speed her pussy begins to quiver. Shortly after that her pussy begins to squirt again and we couldn't be happier about that. We move into the final set up are aiming to fuck her sexy ass. We line up the machine and, insert the dildo, and then start the fucking. We may not get anymore squirting but the orgasms are just as powerful.

Dylan Ryan in 'Blonde Goddess is Destroyed in Devastating Predicament Bondage'

Dylan Ryan - Blonde Goddess is Destroyed in Devastating Predicament Bondage

Dylan has is back and hotter then ever. She has a different kind of glow about her today, and is feeling a little more frisky than usual. The Pope suggests going more extreme with the bondage and she is ready for the challenge. The bondage will be part of the torment in every scene, and in one of them it's the only torment she can handle. This is one of the most grueling shoots that Dylan has had to endure, and you can easily understand why upon watching it. Her muscles are stretched to spread her legs as far and wide as they will go to expose her dripping wet pussy. The pain comes in strict and unstoppable. Her skin turns to a bright shade of red almost instantly as she is tormented. Her feet are going to be a main focus in this first scene, as well as the rest. Her pussy is filled with cock and then emptied with squirting orgasms. The second position will test her on every level. She is held up with one point to the sky and made to balance on her head and toes. Her mouth is tied to her ankles to ensure the most brutal experience of the day. She is then suspended in a side hogtie and tormented more before draining her pussy with more squirting orgasms.The final scene we bend her over a wooden horse and have our way with her one last time, fucking her pussy and finger banging her tight little ass hole.

Dylan Ryan in 'Athletic, Blonde Nympho Dylan Ryan Squirts and Gets An Anal Machine Fucking!'

Dylan Ryan - Athletic, Blonde Nympho Dylan Ryan Squirts and Gets An Anal Machine Fucking!

It is hard to believe that has been two years since the long legs and athletic body of Dylan Ryan graced our set with her raw sexual prowess. And was she ever hungry!! She first purrs as she slowly removes her lacy panty's and bra and teases us with peeks of her tight pink pussy and her natural perky tits. Her short blonde hair shines as she rubs her swollen and hungry clit through thin fabric of her panties. Dylan builds up to a huge orgasm that makes her whole body quiver before she has even taken off all her clothes. She slowly spreads her legs and points the toes of her high heels towards the floor as she ever so slightly touches her clit with a Hitachi. Dylan smiles and knows that her fun has only just begun! She digs in and grinds her hungry pussy on the head of the vibrator and makes the first of her many squirts all over herself. She is a messy girl and delights in the smell, taste, and feel of her pussy juices. Once fully warmed up she opens her legs wide for her first vaginal penetration of the day. A pretty pink dildo slowly begins to slide in and out of her hungry cunt. She begs for the machine to go faster. She can hardly breath as the fucking machine begins to pound her pussy into submission. Her back arches and sweat glistens off her body as she squirts all over the machine. The steam rises and Dylan only wants more. She then rolls over and offers her perfect ass to be devoured by the machine. On her hands and knees the dildo slides effortlessly in and out of her tight pink pussy. She cums with such explosive energy that she collapses onto the couch unable to support her own weight as the fucking machine relentlessly fucks her into breathless ecstasy. After briefly catching her breath she then stands over the machine lets us drool over the entirety of her long luscious legs and toned abdomen. Dylan squirts again and again before offering her hungry asshole to be pleasured with relentless anal penetration. She then has multiple orgasms as her tight ass gets plowed and her clits gets stimulated with a Hitachi. She can't take another moment and explodes one last gigantic orgasm all over herself and the drenched floor. Dylan Ryan gets machined fucked in the ass and squirts all over our fucking machines!!

Chanel Preston in 'Tough Electroslut Dylan Ryan Returns!'

Chanel Preston - Tough Electroslut Dylan Ryan Returns!

Tough electroslut Dylan Ryan is in a predicament inside Chanel Preston's lesbian electro-dungeon! If Dylan puts her foot down, the plug inside her pussy will shock her. Dylan struggles to maintain her balance while Chanel flogs her and uses the violet wand all over her gorgeous body. Next, Dylan is bound and gagged with e-stim sticky pads on her legs and abs. Chanel torments Dylan with pleasure and pain, and fucks her to multiple orgasms with an electrified dildo. More orgasms ensue as Dylan licks Chanel's pussy, and gets finger-banged while wearing an electric butt plug. Chanel continues to crank the electricity up as Dylan comes over and over again!

Dylan Ryan - Teacher's Pet

Dylan is as sexy as she is tough. She exudes that femme fatale sexiness and can be tormented like the bad ass she portrays with her image. She is trapped in hard cold steel and knows that there is no escaping this bondage. Dylan waits patently for her punishment and suffers like a true masochist. Her reward for all of her suffering is mind blowing squirting orgasms that soak the entire room.

Dylan Ryan - Electro Squirt Fest!

Daisy Ducati and Dylan Ryan drench each other in an orgasmic electrosex scene filled with predicament bondage, a wired ass hook, finger banging, pussy licking, face sitting, the violet wand, a vibrating electro cock, and a hard electro strap-on!

Dylan Ryan in 'Rope Slut Begs to Suffer in Extreme Bondage'

Dylan Ryan - Rope Slut Begs to Suffer in Extreme Bondage

Dylan Ryan is a tall drink of champagne. She is as sexy as they come and her beauty is accentuated when she is made helpless in The Pope's ropes. She is put is grueling predicament bondage that is punishment in itself, then her body is abused and tormented and then her pussy is made to cum with squirting explosions.

Dylan Ryan in 'Squirting Pussy and Anal Pounding Drenches Fucking Machines!'

Dylan Ryan - Squirting Pussy and Anal Pounding Drenches Fucking Machines!

It had been far too long since the mighty and awesome pussy of Dylan Ryan graced the set of Fucking Machines with their presence. Dylan never disappoints and coats our set with never ending squirting pussy delight! And if that is not enough, she takes our biggest, strongest machine in the ass which of course makes her cum hole squirt over and over! Dylan Ryan is a Fucking Machine Queen!!!

Dylan Ryan in 'Dylan Ryan's most depraved gangbang fantasy'

Dylan Ryan - Dylan Ryan's most depraved gangbang fantasy

Dylan Ryan is frightened of her deepest, darkest fantasies. She dreams of being dominated, fucked hard, stuffed full and drenched in strangers cum. When Dylan decides to seek a way to make her fantasies come to life, she arrives on the doorstep of an underground business who is making women's most twisted sexual fantasies come to life! Dylan is man handled by anonymous strangers, takes 5 cocks down her hungry throat, has her pussy filled with two giant hard dicks, is DP'd and stuffed airtight. She also takes a fist deep in her cunt and can't stop squirting all over. Watch as this depraved fantasy becomes a reality for Dylan Ryan!

Dylan Ryan - Electric First Date

Andre Shakti goes on a first date with a hot tall blonde, Dylan Ryan, when her dirtiest fantasies are trumped by the electro sex reality that unfolds! Bound to a St. Andrews cross, Dylan fucks, licks and electro torments Andre until she comes hard from the sweet combination of pleasure and pain. Tied to the ceiling with multiple tens pads attached to her ass and thighs, Andre get's fucked with an electrified dildo (The Samurai) and comes multiple times before Dylan demands a pussy licking and orgasm of her own. More pussy licking ensues when Dylan sits on Andre's face while wielding her faithful electric companion (The Violet Wand). With all five fingers in Andre's cunt, Dylan makes Andre shock herself to earn her pleasure. Dylan's squirting orgasm puts the cherry on top of a hot lesbian electro sex date!

Dylan Ryan - Pussy Assault

Dylan is tormented in strict bondage and then her pussy is destroyed with overwhelming orgasms.

Dylan Ryan - Perverted Exam

Dylan Ryan in 'Naughty Foot Nurses: Part 2'

Dylan Ryan - Naughty Foot Nurses: Part 2

Lesbian Nurses toe-fuck, lick pussy, and worship each other's feet until the can't stop cumming!

Dylan Ryan in 'Naughty Foot Nurses: Part One'

Dylan Ryan - Naughty Foot Nurses: Part One

Naughty Nurses Aiden Starr and Dylan Ryan administer two girl foot sucking, foot job, stocking sniffing, foot blow job, and squirting orgasms!

Ariel X in 'Blonde Bombshell Extreme Squirting and Electrosex LIVE!'

Ariel X - Blonde Bombshell Extreme Squirting and Electrosex LIVE!

Ariel X & Aiden Starr shock Dylan with electroplugs, dildos, strap ons, violet wand & sticky pads. Dylan takes ANAL fucking, fisting, & SQUIRTS!!

Lorelei Lee in 'THE LONG AWAITED ORGASMATRON SHOOT - BARBARELLA PARODY FEATURE'

Lorelei Lee - THE LONG AWAITED ORGASMATRON SHOOT - BARBARELLA PARODY FEATURE

Girl's squirting, machine fucking, & ALL YOUR ORGASMATRON dreams come true - anal fucking, pussy licking - all the sex that was NOT in the original!

Dylan Ryan - Part of the Process

Tall hot blonde is bound in extreme devices, tortured, and made to squirt

Ella Nova in '2 Helpless Blonde Whores in Brutal Bondage!'

Ella Nova - 2 Helpless Blonde Whores in Brutal Bondage!

Extreme bondage, 2 blonde pain sluts, crotch ropes, predicament bondage, water torment, squirting orgasms!!!

Bella Rossi in 'Masquerade Orgy with Nine Slaves,100 Horny Guests, Part Three'

Bella Rossi - Masquerade Orgy with Nine Slaves,100 Horny Guests, Part Three

Our slave girls finish off the rest of the horny guests and torture the bartender with orgasms.

Bella Rossi in 'Masquerade Orgy with Nine Slaves,100 Horny Guests, Part Two'

Bella Rossi - Masquerade Orgy with Nine Slaves,100 Horny Guests, Part Two

When the Upper Floor throws an orgy, there is so much sex and bdsm going on than we have to break it into three parts

Bella Rossi in 'Masquerade Orgy with Nine Slaves,100 Horny Guests, Part One'

Bella Rossi - Masquerade Orgy with Nine Slaves,100 Horny Guests, Part One

Nine Trained Slaves are fucked, disciplined and tested in the annual Upper Floor Masquerade Orgy

Dylan Ryan in 'Rivers of Orgasms: Squirting Babe Hoses Our Machines'

Dylan Ryan - Rivers of Orgasms: Squirting Babe Hoses Our Machines

Tall, lean hottie squirts with every single orgasm from the pounding machines. Tied up and cumming, she soaks the metal beast between her legs.

Alani Pi in 'Super Secret Anal Sex Show and Reading'

Alani Pi - Super Secret Anal Sex Show and Reading

The House slaves satisfy the horniest house party yet when author Laura Antoniou reads from the next book in the Marketplace series.

Dylan Ryan in 'Two Ridiculously hot Amazons Wage a Sex War on our Mats'

Dylan Ryan - Two Ridiculously hot Amazons Wage a Sex War on our Mats

The winner shows utter physical dominance in the entire match. She feels that there is not need to be dominate in the sex. Instead the winner makes sw

Dylan Ryan in 'Tall Blond Bombshell Taken Down'

Dylan Ryan - Tall Blond Bombshell Taken Down

Bella Rossi - New Year's Eve!

Bella, Dylan, and Odile are the entertainment for the Upper Floor's New Year's party.

Beretta James in 'Winter Solstice Party'

Beretta James - Winter Solstice Party

THe Upper Floor Solstice Party erupts in BDSM and Sex

Beretta James in 'Synchronicity in Servitude'

Beretta James - Synchronicity in Servitude

Two gorgeous slaves are trained to serve in sync at the Upper Floor House Party

Odile - Odile's Penance

House slave Odile is punished for being a bad, bad girl.

Dylan Ryan - Stefanos' Brunch

It is a lovely afternoon for debauchery on the Upper Floor. Come join us in the lap of luxury and help discipline the House slaves.

Beretta James - House Slave Review

Sex Slaves on the Upper Floor are drilled on protocol, face fucking and taking cock in the ass.

Cytherea in 'Killing the Machines with Pussy SQUIRT: Cytherea and Dylan Ryan'

Cytherea - Killing the Machines with Pussy SQUIRT: Cytherea and Dylan Ryan

10 feet blasts of pussy juice, machines soaked, camera dosed, fucking & squirting that makes legends. Two hot babes put out the fire with their cum!

Odile in 'Community Dinner: Correcting O and Debauching Siouxie'

Odile - Community Dinner: Correcting O and Debauching Siouxie

After several unfortunate mistakes, o is bent over the table and spanked. The Steward places her face between Siouxies legs and demands that she pleas

Chastity Lynn - Slave Initiation: buttons

Chastity Lynn aka buttons is initiated as the newest House slave.

Dylan Ryan - Stefanos' Brunch

The House has another Brunch filled with amazing BDSM debauchery. Tramp and pistol are punished in front of the guests by the Steward, and tramp is made an example of. The party moves to the lounge, pistol is put in a cage and the guests are allowed to have their way with her while tramp services another guest.

Odile in 'House Party:Diamonds from the Ash'

Odile - House Party:Diamonds from the Ash

A dismissal starts the evening, followed by an evening of sadistic pleasure and pain and non stop fucking.

Dylan Ryan in 'Squirt-O-Vision: She cums on the Lens so Much You will Get Wet'

Dylan Ryan - Squirt-O-Vision: She cums on the Lens so Much You will Get Wet

Hot, tall blonde breaks squirting records while getting fucked by machines. She soaks the camera lens like a sponge.

Beretta James in 'Community Dinner With James Deen'

Beretta James - Community Dinner With James Deen

The slaves make mistake after mistake, but luckily our guest of honor, James Deen, if there to punish them with his cock and creative humiliation.

Andre Shakti in 'Dylan White Lightening vs. up and coming rookie Andre The Teflon Don Shakti'

Andre Shakti - Dylan White Lightening vs. up and coming rookie Andre The Teflon Don Shakti

Dylan Ryan and rookie Andre Shakti go head to head in the hottest unscripted sexual wrestling on the net!

Odile - Stefanos' Brunch

The slaves are here to serve the House, but not always through basic service. Today they are serving as entertainment for the guests. Stefanos takes turns playing with the slaves, and eventually makes them put on a a sexual display for our guests. One of our slaves, o, has never been fisted, and kaos makes a valiant attempt, but does not succeed. Later, tramp is put on a table and brutally fucked by kaos, while Stefanos punishes her. She squirts all over the table once allowed to have the final orgasm of the day.

Dylan Ryan in 'Squirt Alert: So MUCH Girl Cum'

Dylan Ryan - Squirt Alert: So MUCH Girl Cum

Screaming, squirting, bursting, cum slinging orgasms from a tall hot babe who doesn't quit until she has soaked the machines in cum & done a great DP

Lyla Storm - House Party: Debauchery

A night of debauchery and sexual service on TUF with guest of honor, Derrick Pierce.

Dylan Ryan in 'July Tag Team Match: Rd 4 Sexually Destroyed and Covered in Squirt'

Dylan Ryan - July Tag Team Match: Rd 4 Sexually Destroyed and Covered in Squirt

Wenona, Dylan Ryan, and new ref Rain Degrey fuck the shit out of the losers, squirt all over them, and kick them out the door!!

Beretta James in 'Dinner Party: Air Tight Guest'

Beretta James - Dinner Party: Air Tight Guest

Dannika is made air tight by the House slaves during our monthly dinner party.

Dylan Ryan in 'Tits vs. Legs; Round 3 of July's Epic Tag Team Match!'

Dylan Ryan - Tits vs. Legs; Round 3 of July's Epic Tag Team Match!

Curvacious Izamar and Krissy Lynn battle slim, sexy Dylan and Wenona in Round 3 of July's Tag Team Live Show

Dylan Ryan in 'ROUND 2 of July's Tag Team Match! Wild kinky bitches fight it out'

Dylan Ryan - ROUND 2 of July's Tag Team Match! Wild kinky bitches fight it out

Izamar, Dylan, Krissy and Wenona hit the mat with a vengeance! These crazy bitches will stop at nothing to reach the top.

Dylan Ryan in 'July Tag Team: Rd 1- 4 Sexy Wrestlers Battle for Dominance and Control'

Dylan Ryan - July Tag Team: Rd 1- 4 Sexy Wrestlers Battle for Dominance and Control

Team red and Team Pink sexually violate one another while holding them in inescapable submission holds, finger fucking. Sexual Wrestling!

Lyla Storm in 'Jack Hammer's Birthday Party'

Lyla Storm - Jack Hammer's Birthday Party

The Butler's birthday party turns into a full on BDSM fuck fest!

Maitresse Madeline in 'Please Fuck My Wife While My Prostate Is Milked!'

Maitresse Madeline - Please Fuck My Wife While My Prostate Is Milked!

Wife cuckolds husband with another couple and husband cums in his chastity belt from prostate milking, TWICE!!!!

Krysta Kaos in 'Community Dinner: Slave correction'

Krysta Kaos - Community Dinner: Slave correction

An evening of correction and stripping the slaves of their beloved collars and cuffs because of disappointing the Steward.

Beretta James in 'Piano Party-Exploring TUF'

Beretta James - Piano Party-Exploring TUF

Out of the lounge and down the hall to have a piano party as we explore The Upper Floor.

Lyla Storm - Uniform Party

All of our kinky uniform fetishists are out for an amazing sexually charged evening.

Lyla Storm in 'Slave Initiation: chrome'

Lyla Storm - Slave Initiation: chrome

Lyla Storm is initiated as the new House slave, but not before she is fucked into oblivion by Mark Davis, Stefanos, and the House slaves.

Beretta James in 'House Party: Leather Appreciation'

Beretta James - House Party: Leather Appreciation

House slaves shine leather and give sexual service all night long.

Beretta James in 'Community Dinner:Table Service'

Beretta James - Community Dinner:Table Service

Grace is back and puts the slaves through the paces of table service before using them to satisfy her sexual desires.

Krysta Kaos in 'Slave Initiation: piggy Part 2'

Krysta Kaos - Slave Initiation: piggy Part 2

Piggy is tormented more and put through the paces by Derrick Pierce, James Deen, and all of the House slaves.

Krysta Kaos in 'Slave Initiation: piggy Part 1'

Krysta Kaos - Slave Initiation: piggy Part 1

A new addition to TUF comes in the form of Lily LaBeau aka piggy. She is made to serve all guests while crawling, then is sadistically fucked.

Beretta James - Promotion of o

After a lengthy service to the House as a trainee odile is promoted as a slave

Krysta Kaos in 'House Party:Consort is corrected.'

Krysta Kaos - House Party:Consort is corrected.

As the consorts body twirls in a tight inverted suspension, her masters leave an imprint of each failure on her creamy skin with a flogger.

Krysta Kaos in 'Slave Initiation: pistol'

Krysta Kaos - Slave Initiation: pistol

The finale kicks off with a wicked zipper and ends with slave pistol airtight, slave cock in her pussy and ass, and The Steward in her mouth.

Dylan Ryan - Stefanos' Brunch

Stefanos introduces slave pistol to the Sunday brunch crowd, groping her naked body and making her crawl across the table to display herself. Though she has a reputation as an excellent sex slave, pistol is made to place her head under the table top and allow her holes to be violated by another slave before she will be deemed worthy for use by a guest. Slutty slave tramp is more than happy to fuck pistol mercilessly with a strap on while the guests cheer.Once the party moves into the lounge, real life D/s couple Alpha and omega get into a deep disciplinary scene in which omega is reduced to sorrowful apologies while Alpha corrects her with a strict paddling and a tazer. Hot little bonnie gets horny and curious about the upper floor fucking machine, and soon finds herself cumming uncontrollably with the machine on high. Josh and pynki enjoy the finer points of the violet wand, fucking pynki with a glowing hot electrical wand and making her lick her juices off. The afternoon concludes with mickey mod shoving his cock down nerines throat and using his belt to hold her tight against him.

Krysta Kaos in 'Slave Competition Party'

Krysta Kaos - Slave Competition Party

a beautiful house guest decides to challenge both slaves and jumps on Derricks cock while they are both busy eating each others pussies

Krysta Kaos in 'House Party: Stretching pussy'

Krysta Kaos - House Party: Stretching pussy

The winner savors and pleases herself with the gentlemans cocks, while the loser is brutally whipped, berated, and punished with a rough fucking.

Skin Diamond - Restriction Lifted

Dylan Ryan - Tall blonde slut suffers from nipple torture, sadistic beatings, and extreme squirting orgasms

Tall blonde slut suffers from nipple torture, sadistic beatings, and extreme squirting orgasms

Dylan Ryan - Penny Pax

Adorable unassuming all natural blonde gets spanked, whipped, made to worship feet and strap-on ass fucked by statuesque lesbian dominatrix.

Beretta James in 'New Year Party Part 2'

Beretta James - New Year Party Part 2

The Upper Floor plays host to one of the wildest sex parties we may see in 2012

Beretta James in 'New Year Party Part 1 Fresh Meat for 2012'

Beretta James - New Year Party Part 1 Fresh Meat for 2012

All four slave girls are commanded to entertain the room with an all girl orgy until they are requested for use.

Aiden Starr - A Divine Giantess

Beautiful giantess commands 21 year old slaveboy into ass worship, trampling, pegging, humiliation, CBT and a cruel ruined orgasm.

Odile in 'Community Dinner Reminding the tramp'

Odile - Community Dinner Reminding the tramp

Uppity blond slave whipped back into shape as real BDSM players fuck on the dinner table

Krysta Kaos in 'Service Session: Cleaning the Halls'

Krysta Kaos - Service Session: Cleaning the Halls

The winner receives an orgasm and the exquisite pleasure of nipple torture. The other two are whipped, strung up in a suspension, and fucked.

Felony in 'Lezdom Gangbang: 19 Years Old and Kinky As Hell!'

Felony - Lezdom Gangbang: 19 Years Old and Kinky As Hell!

Cute 19 year old is spanked, fisted, squirted on and gang banged by a groups of hot lezdoms.

Krysta Kaos - Asphyxia's Initiation

Iona Grace in 'Service Session Fisted for the first time'

Iona Grace - Service Session Fisted for the first time

This is both girls first time fisting and it is a raw, explosive, and surprising sexual encounter that is not to be missed.

Krysta Kaos in 'Stefanos Brunch Two Year Anniversary'

Krysta Kaos - Stefanos Brunch Two Year Anniversary

Juliette March in 'Service Session: Pixie's birthday'

Juliette March - Service Session: Pixie's birthday

Nympho pixie is strapped down and made to swallow dildo while the other house slaves gorge themselves on cock mere inches from her hungry face.

Odile - Cocktail Party: Squirting

Tight-bodied odile is strung up in a tight suspension while tramp is punished for squirting all over the bar instead of making drinks.

Dylan Ryan - Service Session

This is a day of testing our tramp with electric zappers, smothering leather face masks, and brutal squirting orgasms torn from her sensitive pussy.

Alexxa Bound - Community Dinner

The evening turns into a raucous girl on girl wrestling match for The Stewards cock. Everyone wins and is fucked in the end.

Dylan Ryan in 'Training Dylan-Day 5 Live Show-Final Test'

Dylan Ryan - Training Dylan-Day 5 Live Show-Final Test

This masochistic slut has been trained and it is time to find out how much of her training has been retained. Her body is pushed to a breaking point.

Juliette March in 'Alone with The Steward'

Juliette March - Alone with The Steward

The slaves aim to please, but end up riding the fucking machine to entertain when they cannot properly serve.

Juliette March in 'New Slaves Struggle to Please'

Juliette March - New Slaves Struggle to Please

The Steward underlines the trade between pain and pleasure as he tortures pixies sensitive nipples in exchange for tramps face between her legs

Skin Diamond - Reminding Ash

A brutal and elegant instance of discipline and submission. Ash is degraded in front of the other slaves, flogged, made to beg, and punished.

Dylan Ryan in 'Dylan-Day 4 Sexual Domination'

Dylan Ryan - Dylan-Day 4 Sexual Domination

Dylan is fucked hard and made to deep throat all day in preparation for her live show.

Isis Love - Dylan Returns

Dylan Ryan returns to WP to overcome her fear of electrical play! Lesbian domination, bondage, and more!

Dylan Ryan in 'Tall hot blonde on tip-toes hanging from a crotch rope, made to squirt.'

Dylan Ryan - Tall hot blonde on tip-toes hanging from a crotch rope, made to squirt.

Tall long legged blond is held in a creepy room by masked man. She's bound to wall, abused with crotch rope, and made to squirt.

Dylan Ryan in 'Day 3 Facing Fears with Extreme Binds and Pussy Stretching'

Dylan Ryan - Day 3 Facing Fears with Extreme Binds and Pussy Stretching

Dylan is bound tightly, and made to face her biggest fears. Extreme bondage makes this slut work harder to make any progress at all.

Dylan Ryan in 'Dylan - Day Two Sexual Testing, Electricity, and Mummification Suspension'

Dylan Ryan - Dylan - Day Two Sexual Testing, Electricity, and Mummification Suspension

Dylan Ryan is bound, fucked, made to suck cock, suspended, and put through grueling electrical torture.

Dylan Ryan in 'Tall long legged blond is hung upside down, made to cum Choked, clamped and abused, left hanging..'

Dylan Ryan - Tall long legged blond is hung upside down, made to cum Choked, clamped and abused, left hanging..

Tall long legged blond is held in a creepy room and abused. Hung upside down, manhandled, and made to cum. Choked, clamped and abused, left hanging..

Felony - Lesbian Glory Hole

Curious blonde finds a pussy in a glory hole and is punished and fucked for making it wet!

Dylan Ryan in 'Dylan - Day One Tight Bondage, Extreme Orgasms, and Full Domination!'

Dylan Ryan - Dylan - Day One Tight Bondage, Extreme Orgasms, and Full Domination!

She is a smart submissive with the drive to excel, but her fears are what I'm interested in.

Dylan Ryan in 'Tall blonde bound and fucked into oblivion'

Dylan Ryan - Tall blonde bound and fucked into oblivion

Dylan is pounded in the ass by the fucksall. Asshooked by the mouth, whipped hard. Plastic wrapped, suction cupped and fingered into squirting frenzy.

Dylan Ryan in 'Rich blond taken, bound with tape Manhandled, stripped, exposed, made to cum like a common whore.'

Dylan Ryan - Rich blond taken, bound with tape Manhandled, stripped, exposed, made to cum like a common whore.

Rich blond captured and bound with tape. Taken & abused, stripped, groped, & fucked. Made to struggle. Helpless to resist, made to cum like a slut.

Dylan Ryan - Locker Room Fantasy

Dylan Ryan lives out her fantasy of being gangbanged in the locker room by 5 guys. Tied up, surrounded by cock, and covered in cum.

Dylan Ryan - Filthy Filthy Whore

Dylan Ryan is fucked in every hole in a dirty auto repair shop while the mechanics fondle her tits and big round ass

Dylan Ryan in 'How much do you love zippers'

Dylan Ryan - How much do you love zippers

Dylan metal bound with Sybian and zipper to bowling ball predicament.

Dylan Ryan in 'Upside-Down and Helpless'

Dylan Ryan - Upside-Down and Helpless

Sexy Dylan metal-bound upside down, helpless and machine fucked.

Madison Young - Dylan's Day Spa nightmare

Dylan's Day Spa nightmare

Dylan Ryan in 'Anal Audition: Dylan's Honeycomb Attempt'

Dylan Ryan - Anal Audition: Dylan's Honeycomb Attempt

Dylan Attempts the Honeycomb for her Anal Audition

Dylan Ryan in 'Dylan's Bamboo Bondage Dilemma'

Dylan Ryan - Dylan's Bamboo Bondage Dilemma

Bamboo Bondage for Dylan

Dylan Ryan - Dylan and John Strong

Dylan Ryan in 'The Training of Dylan, Day Four'

Dylan Ryan - The Training of Dylan, Day Four

Double Slave Sluts beg for Masters Cock in her Ass

Dylan Ryan in 'The Training of Dylan, Day Three'

Dylan Ryan - The Training of Dylan, Day Three

Slave girl trained to fuck

Dylan Ryan in 'The Training of Dylan, Day Two'

Dylan Ryan - The Training of Dylan, Day Two

Blonde Brat trained to submit to Sex and Sadism!

Dylan Ryan in 'The Training Of Dylan, Day One'

Dylan Ryan - The Training Of Dylan, Day One

Tight blonde slave girl pushed to her limits!

Dylan Ryan in 'Lorelei Lee, Keeani Lei, Dana DeArmond, Princess Donna Dolore and Dylan Ryan'

Dylan Ryan - Lorelei Lee, Keeani Lei, Dana DeArmond, Princess Donna Dolore and Dylan Ryan

After the tea party shoot, some of the girls still wanted to romp so I set up the wet dreams, sat back and them have at it! Princess Donna even makes a guest appearance to help Dana cum one more time! Have a good weekend.

Lorelei Lee in 'Dylan Ryan, Lorelei Lee, Jenni Lee, Dana DeArmond and Keeani Lei'

Lorelei Lee - Dylan Ryan, Lorelei Lee, Jenni Lee, Dana DeArmond and Keeani Lei

The last update in the series finds our five stunning girls sitting pretty at an afternoon tea party until the eagerness to eat more than cake gets the best of them. Sipping tea and sampling petit fours quickly descends into a pussy licking, machine-fucking orgy. The quaint backyard echoes with orgasms as Jenni Lee screams in pleasure, Keaani squirts, Lorelei does double penetration with the predator, Dylan swallows huge cock and Dana takes the trespasser deep and hard in her ass. The party carries on well into the night leaving our tea party guests worn out and satisfied.

Dylan Ryan in 'Dylan Ryan, Jenni Lee, Dana DeArmond, Keeani Lei and Princess Donna Dolore'

Dylan Ryan - Dylan Ryan, Jenni Lee, Dana DeArmond, Keeani Lei and Princess Donna Dolore

Two girls from my Collection, Dana and Jenni Lee get a break from the dungeon and a day to play in the woods with some newer bitches. First they fuck Keeani and Dylan with electric strap-ons, then I give Dana control of all the girls and let her have her way with them. She makes them suck her toes and pussy and ass till she cums, then I turn up the electricity till they squeal like pigs!

Dana DeArmond in 'Keeani Lei, Lorelei Lee, Jenni Lee, Dylan Ryan and Dana DeArmond'

Dana DeArmond - Keeani Lei, Lorelei Lee, Jenni Lee, Dylan Ryan and Dana DeArmond

Part 3 of the series finds Keeani and Dana in the garage with their fucking drills. Each girl take turns getting drilled until along comes Lorelei with her strap on I?ve also included a short preview of the grand finale: the five girl tea party.

Dana DeArmond in 'Dana DeArmond, Lorelei Lee and Dylan Ryan'

Dana DeArmond - Dana DeArmond, Lorelei Lee and Dylan Ryan

Picking flowers has never been so rewarding. Foxy Dana finds the minimite, has a dp session with the fucksall, and takes on the pussy wacker and predator? meanwhile Lorelei and Dylan finish their machine fucking session in the gym.

Dylan Ryan in 'The Titan (0-0) vs. The Pirate (1-0)'

Dylan Ryan - The Titan (0-0) vs. The Pirate (1-0)

The Titan is big, strong, and is not used to getting pushed around. The Pirate takes command early and punishes the Titan. The Titan is made to say the humiliating words ?I submit? twice. The Titan just can?t seem to keep the Pirates? fingers out of her pussy. In Rd4 the Pirate takes it to the ungrateful Titan US style!iPod clips now available

Lorelei Lee - and Dylan Ryan

The quiet villa is a not so quiet get away for Lorelei Lee. After a stroll of the grounds she plunges into the pool only to emerge to find machines lining the deck, waiting for her. This strange little hideaway in the hills is full of all sorts of machine adventures and sexy guests. This is the first in a five part series of fucking machine adventures.

Dylan Ryan - Dylan Ryan

Today I would like to introduce you to a hot local newbie, Dylan. Dylan had her introduction to bondage and electricity in the great outdoors. I tie her up throw her around in the mud like the little piggy she is, then I make her cum, shock her with the cattle prod, and hogtie her facedown in the dirt. Of course being the dirty whore she is, she loved every minute of the treatment I gave her.

Dylan Ryan - and Judas

Dylan makes Her pathetic boy toy pay when he gets the prison treatment by his cellmates on the same day as her conjugal visit. She beats, ass fucks and ball slaps him into a squirming, whimpering puddle of prison meat.

Dylan Ryan - Dylan Ryan

Sexy newcomer Dylan shows us how it?s done as she fucks her way to total orgasmic bliss right on top of our welder?s motorcycle! She takes the new intruder all the way up to top speed and likes it so much we just had to do it twice. The shaking knees and permagrin say it all. Dylan will be back.Also - the subclips are now entire scenes instead of two minute segments. Less downloading, same amount of porn!

DragonLily in 'Dylan Ryan and DragonLily'

DragonLily - Dylan Ryan and DragonLily

Dragonlily takes local girl Dylan on a journey of pleasure and pain. Dylan endures all the hard punishment and fucking that Dragonlily dishes out. Great interaction and chemistry in this very entertaining session!

Scenes from other sites featuring Dylan Ryan

Dylan Ryan - Under His Boot

Dylan Ryan - Squirting Screaming Orgasms and Anal Machine Fucking

Dylan Ryan - Blonde Goddess is Destroyed in Devastating Predicament Bondage

Dylan Ryan - Athletic, Blonde Nympho Dylan Ryan Squirts and Gets An Anal Machine Fucking!

Chanel Preston - Tough Electroslut Dylan Ryan Returns!

Dylan Ryan - Teacher's Pet

Dylan Ryan - Electro Squirt Fest!

Dylan Ryan - Rope Slut Begs to Suffer in Extreme Bondage

Dylan Ryan - Squirting Pussy and Anal Pounding Drenches Fucking Machines!

Dylan Ryan - Dylan Ryan's most depraved gangbang fantasy

Dylan Ryan - Electric First Date

Dylan Ryan - Pussy Assault

Dylan is tormented in strict bondage and then her pussy is destroyed with overwhelming orgasms.

Dylan Ryan - Perverted Exam

Dylan Ryan - Naughty Foot Nurses: Part 2

Lesbian Nurses toe-fuck, lick pussy, and worship each other's feet until the can't stop cumming!

Dylan Ryan - Naughty Foot Nurses: Part One

Naughty Nurses Aiden Starr and Dylan Ryan administer two girl foot sucking, foot job, stocking sniffing, foot blow job, and squirting orgasms!

Ariel X - Blonde Bombshell Extreme Squirting and Electrosex LIVE!

Ariel X & Aiden Starr shock Dylan with electroplugs, dildos, strap ons, violet wand & sticky pads. Dylan takes ANAL fucking, fisting, & SQUIRTS!!

Lorelei Lee - THE LONG AWAITED ORGASMATRON SHOOT - BARBARELLA PARODY FEATURE

Girl's squirting, machine fucking, & ALL YOUR ORGASMATRON dreams come true - anal fucking, pussy licking - all the sex that was NOT in the original!

Dylan Ryan - Part of the Process

Tall hot blonde is bound in extreme devices, tortured, and made to squirt

Ella Nova - 2 Helpless Blonde Whores in Brutal Bondage!

Extreme bondage, 2 blonde pain sluts, crotch ropes, predicament bondage, water torment, squirting orgasms!!!

Bella Rossi - Masquerade Orgy with Nine Slaves,100 Horny Guests, Part Three

Our slave girls finish off the rest of the horny guests and torture the bartender with orgasms.

Bella Rossi - Masquerade Orgy with Nine Slaves,100 Horny Guests, Part Two

When the Upper Floor throws an orgy, there is so much sex and bdsm going on than we have to break it into three parts

Bella Rossi - Masquerade Orgy with Nine Slaves,100 Horny Guests, Part One

Nine Trained Slaves are fucked, disciplined and tested in the annual Upper Floor Masquerade Orgy

Dylan Ryan - Rivers of Orgasms: Squirting Babe Hoses Our Machines

Tall, lean hottie squirts with every single orgasm from the pounding machines. Tied up and cumming, she soaks the metal beast between her legs.

Alani Pi - Super Secret Anal Sex Show and Reading

The House slaves satisfy the horniest house party yet when author Laura Antoniou reads from the next book in the Marketplace series.

Dylan Ryan - Two Ridiculously hot Amazons Wage a Sex War on our Mats

The winner shows utter physical dominance in the entire match. She feels that there is not need to be dominate in the sex. Instead the winner makes sw

Dylan Ryan - Tall Blond Bombshell Taken Down

Bella Rossi - New Year's Eve!

Bella, Dylan, and Odile are the entertainment for the Upper Floor's New Year's party.

Beretta James - Winter Solstice Party

THe Upper Floor Solstice Party erupts in BDSM and Sex

Beretta James - Synchronicity in Servitude

Two gorgeous slaves are trained to serve in sync at the Upper Floor House Party

Odile - Odile's Penance

House slave Odile is punished for being a bad, bad girl.

Dylan Ryan - Stefanos' Brunch

It is a lovely afternoon for debauchery on the Upper Floor. Come join us in the lap of luxury and help discipline the House slaves.

Beretta James - House Slave Review

Sex Slaves on the Upper Floor are drilled on protocol, face fucking and taking cock in the ass.

Cytherea - Killing the Machines with Pussy SQUIRT: Cytherea and Dylan Ryan

10 feet blasts of pussy juice, machines soaked, camera dosed, fucking & squirting that makes legends. Two hot babes put out the fire with their cum!

Odile - Community Dinner: Correcting O and Debauching Siouxie

After several unfortunate mistakes, o is bent over the table and spanked. The Steward places her face between Siouxies legs and demands that she pleas

Chastity Lynn - Slave Initiation: buttons

Chastity Lynn aka buttons is initiated as the newest House slave.

Dylan Ryan - Stefanos' Brunch

Odile - House Party:Diamonds from the Ash

A dismissal starts the evening, followed by an evening of sadistic pleasure and pain and non stop fucking.

Dylan Ryan - Squirt-O-Vision: She cums on the Lens so Much You will Get Wet

Hot, tall blonde breaks squirting records while getting fucked by machines. She soaks the camera lens like a sponge.

Beretta James - Community Dinner With James Deen

The slaves make mistake after mistake, but luckily our guest of honor, James Deen, if there to punish them with his cock and creative humiliation.

Andre Shakti - Dylan White Lightening vs. up and coming rookie Andre The Teflon Don Shakti

Dylan Ryan and rookie Andre Shakti go head to head in the hottest unscripted sexual wrestling on the net!

Odile - Stefanos' Brunch

Dylan Ryan - Squirt Alert: So MUCH Girl Cum

Screaming, squirting, bursting, cum slinging orgasms from a tall hot babe who doesn't quit until she has soaked the machines in cum & done a great DP

Lyla Storm - House Party: Debauchery

A night of debauchery and sexual service on TUF with guest of honor, Derrick Pierce.

Dylan Ryan - July Tag Team Match: Rd 4 Sexually Destroyed and Covered in Squirt

Wenona, Dylan Ryan, and new ref Rain Degrey fuck the shit out of the losers, squirt all over them, and kick them out the door!!

Beretta James - Dinner Party: Air Tight Guest

Dannika is made air tight by the House slaves during our monthly dinner party.

Dylan Ryan - Tits vs. Legs; Round 3 of July's Epic Tag Team Match!

Curvacious Izamar and Krissy Lynn battle slim, sexy Dylan and Wenona in Round 3 of July's Tag Team Live Show

Dylan Ryan - ROUND 2 of July's Tag Team Match! Wild kinky bitches fight it out

Izamar, Dylan, Krissy and Wenona hit the mat with a vengeance! These crazy bitches will stop at nothing to reach the top.

Dylan Ryan - July Tag Team: Rd 1- 4 Sexy Wrestlers Battle for Dominance and Control

Team red and Team Pink sexually violate one another while holding them in inescapable submission holds, finger fucking. Sexual Wrestling!

Lyla Storm - Jack Hammer's Birthday Party

The Butler's birthday party turns into a full on BDSM fuck fest!

Maitresse Madeline - Please Fuck My Wife While My Prostate Is Milked!

Wife cuckolds husband with another couple and husband cums in his chastity belt from prostate milking, TWICE!!!!

Krysta Kaos - Community Dinner: Slave correction

An evening of correction and stripping the slaves of their beloved collars and cuffs because of disappointing the Steward.

Beretta James - Piano Party-Exploring TUF

Out of the lounge and down the hall to have a piano party as we explore The Upper Floor.

Lyla Storm - Uniform Party

All of our kinky uniform fetishists are out for an amazing sexually charged evening.

Lyla Storm - Slave Initiation: chrome

Lyla Storm is initiated as the new House slave, but not before she is fucked into oblivion by Mark Davis, Stefanos, and the House slaves.

Beretta James - House Party: Leather Appreciation

House slaves shine leather and give sexual service all night long.

Beretta James - Community Dinner:Table Service

Grace is back and puts the slaves through the paces of table service before using them to satisfy her sexual desires.

Krysta Kaos - Slave Initiation: piggy Part 2

Piggy is tormented more and put through the paces by Derrick Pierce, James Deen, and all of the House slaves.

Krysta Kaos - Slave Initiation: piggy Part 1

A new addition to TUF comes in the form of Lily LaBeau aka piggy. She is made to serve all guests while crawling, then is sadistically fucked.

Beretta James - Promotion of o

After a lengthy service to the House as a trainee odile is promoted as a slave

Krysta Kaos - House Party:Consort is corrected.

As the consorts body twirls in a tight inverted suspension, her masters leave an imprint of each failure on her creamy skin with a flogger.

Krysta Kaos - Slave Initiation: pistol

The finale kicks off with a wicked zipper and ends with slave pistol airtight, slave cock in her pussy and ass, and The Steward in her mouth.

Dylan Ryan - Stefanos' Brunch

Krysta Kaos - Slave Competition Party

a beautiful house guest decides to challenge both slaves and jumps on Derricks cock while they are both busy eating each others pussies

Krysta Kaos - House Party: Stretching pussy

The winner savors and pleases herself with the gentlemans cocks, while the loser is brutally whipped, berated, and punished with a rough fucking.

Skin Diamond - Restriction Lifted

Dylan Ryan - Tall blonde slut suffers from nipple torture, sadistic beatings, and extreme squirting orgasms

Tall blonde slut suffers from nipple torture, sadistic beatings, and extreme squirting orgasms

Dylan Ryan - Penny Pax

Adorable unassuming all natural blonde gets spanked, whipped, made to worship feet and strap-on ass fucked by statuesque lesbian dominatrix.

Beretta James - New Year Party Part 2

The Upper Floor plays host to one of the wildest sex parties we may see in 2012

Beretta James - New Year Party Part 1 Fresh Meat for 2012

All four slave girls are commanded to entertain the room with an all girl orgy until they are requested for use.

Aiden Starr - A Divine Giantess

Beautiful giantess commands 21 year old slaveboy into ass worship, trampling, pegging, humiliation, CBT and a cruel ruined orgasm.

Odile - Community Dinner Reminding the tramp

Uppity blond slave whipped back into shape as real BDSM players fuck on the dinner table

Krysta Kaos - Service Session: Cleaning the Halls

The winner receives an orgasm and the exquisite pleasure of nipple torture. The other two are whipped, strung up in a suspension, and fucked.

Felony - Lezdom Gangbang: 19 Years Old and Kinky As Hell!

Cute 19 year old is spanked, fisted, squirted on and gang banged by a groups of hot lezdoms.

Krysta Kaos - Asphyxia's Initiation

Iona Grace - Service Session Fisted for the first time

This is both girls first time fisting and it is a raw, explosive, and surprising sexual encounter that is not to be missed.

Krysta Kaos - Stefanos Brunch Two Year Anniversary

Juliette March - Service Session: Pixie's birthday

Nympho pixie is strapped down and made to swallow dildo while the other house slaves gorge themselves on cock mere inches from her hungry face.

Odile - Cocktail Party: Squirting

Tight-bodied odile is strung up in a tight suspension while tramp is punished for squirting all over the bar instead of making drinks.

Dylan Ryan - Service Session

This is a day of testing our tramp with electric zappers, smothering leather face masks, and brutal squirting orgasms torn from her sensitive pussy.

Alexxa Bound - Community Dinner

The evening turns into a raucous girl on girl wrestling match for The Stewards cock. Everyone wins and is fucked in the end.

Dylan Ryan - Training Dylan-Day 5 Live Show-Final Test

This masochistic slut has been trained and it is time to find out how much of her training has been retained. Her body is pushed to a breaking point.

Juliette March - Alone with The Steward

The slaves aim to please, but end up riding the fucking machine to entertain when they cannot properly serve.

Juliette March - New Slaves Struggle to Please

The Steward underlines the trade between pain and pleasure as he tortures pixies sensitive nipples in exchange for tramps face between her legs

Skin Diamond - Reminding Ash

A brutal and elegant instance of discipline and submission. Ash is degraded in front of the other slaves, flogged, made to beg, and punished.

Dylan Ryan - Dylan-Day 4 Sexual Domination

Dylan is fucked hard and made to deep throat all day in preparation for her live show.

Isis Love - Dylan Returns

Dylan Ryan returns to WP to overcome her fear of electrical play! Lesbian domination, bondage, and more!

Dylan Ryan - Tall hot blonde on tip-toes hanging from a crotch rope, made to squirt.

Tall long legged blond is held in a creepy room by masked man. She's bound to wall, abused with crotch rope, and made to squirt.

Dylan Ryan - Day 3 Facing Fears with Extreme Binds and Pussy Stretching

Dylan is bound tightly, and made to face her biggest fears. Extreme bondage makes this slut work harder to make any progress at all.

Dylan Ryan - Dylan - Day Two Sexual Testing, Electricity, and Mummification Suspension

Dylan Ryan is bound, fucked, made to suck cock, suspended, and put through grueling electrical torture.

Dylan Ryan - Tall long legged blond is hung upside down, made to cum Choked, clamped and abused, left hanging..

Tall long legged blond is held in a creepy room and abused. Hung upside down, manhandled, and made to cum. Choked, clamped and abused, left hanging..

Felony - Lesbian Glory Hole

Curious blonde finds a pussy in a glory hole and is punished and fucked for making it wet!

Dylan Ryan - Dylan - Day One Tight Bondage, Extreme Orgasms, and Full Domination!

She is a smart submissive with the drive to excel, but her fears are what I'm interested in.

Dylan Ryan - Tall blonde bound and fucked into oblivion

Dylan is pounded in the ass by the fucksall. Asshooked by the mouth, whipped hard. Plastic wrapped, suction cupped and fingered into squirting frenzy.