Maitresse Madeline in 'Kink' Oops, she did it again: Prostate Milking (Thumbnail 3)

Maitresse Madeline,Mirko in 'Kink' - Oops, she did it again: Prostate Milking (Divine Bitches)

Maitresse Madeline picks up a new dude who has never done porno and beats him and milks his prostate until cum is bubbling and boil out his cock!

Released : December 12, 2012
Tags : Wax, Whipping, Femdom, Straight, Dominatrix, Slave, Male Sub, Corporal Punishment, Bdsm, Prostate Stimulation, Pussy Eating, Face Sitting, Humiliation, Fingering, Bondage, Pegging, CBT, Orgasm denial

Pictures from Maitresse Madeline,Mirko in 'Kink' Oops, she did it again: Prostate Milking

Download 'Maitresse Madeline in Oops, she did it again: Prostate Milking'

Video from Maitresse Madeline,Mirko in 'Kink' Oops, she did it again: Prostate Milking

More 'Kink' scenes from Maitresse Madeline,Mirko

Maitresse Madeline in 'Divine Bitches Halloween Special: FemDom Freakshow! SPH cock edging!'

Maitresse Madeline - Divine Bitches Halloween Special: FemDom Freakshow! SPH cock edging!

A Divine Halloween Special. Jimmy Bullet tries out for Madeline's freakshow with his cute litte horny cock. She edges his dick to insanity!

Maitresse Madeline in 'The Maitresse Milks Virgin Prostrate and Punishes Dripping Cock!'

Maitresse Madeline - The Maitresse Milks Virgin Prostrate and Punishes Dripping Cock!

Maitresse uses her legendary prostrate-milking talents to steal the cum from this eager anal slut after fucking him with the biggest strap-on at Kink!

Maitresse Madeline - Lesbian Dungeon

Sexy red headed dominatrix dominates and ass fucks all natural gorgeous slave girl.

Aiden Starr in 'Corporate Scum CFNM Humiliation Take Over: Part 2'

Aiden Starr - Corporate Scum CFNM Humiliation Take Over: Part 2

The Divine Bitches Corporation humiliate yuppie scum with CFNM, extreme humiliation, coerced bi, involuntary cum eating and prostate milking!

Maitresse Madeline in 'Sex Magick: BRUTAL and EXTREME sounding!'

Maitresse Madeline - Sex Magick: BRUTAL and EXTREME sounding!

Maitresse Madeline gives an EXTREME and BRUTAL sounding teasing and fucking her slaves cock from the inside out!

Maitresse Madeline in 'FemDom Sperm Thief'

Maitresse Madeline - FemDom Sperm Thief

Maitresse Madeline prostate milks and steals the sperm from her aching balled slave.

Maitresse Madeline in 'The Return of Maitresse Madeline'

Maitresse Madeline - The Return of Maitresse Madeline

Clit zapping and electric tickling, pussy licking, EMS pads, ANAL electric strap on, strict bondage and intense electrified orgasms!

Maitresse Madeline in 'Purchased Goods: EXTREME squirting and lezdom anal sex!'

Maitresse Madeline - Purchased Goods: EXTREME squirting and lezdom anal sex!

Savannah Fox is bought on the black market punished and strap-on ass fucked with EXTREME squirting by gorgeous lezdom, Maitresse Madeline

Lorelei Lee in 'Barbarella and the Black Queen'

Lorelei Lee - Barbarella and the Black Queen

The kinky adventures of Barbarella continues with Lorelei Lee & Maitresse Madeline dominating each other with strap-ons, whips, bondage & humiliation.

Cherry Torn in 'The Secret Femdom Society of Prostate Milking.'

Cherry Torn - The Secret Femdom Society of Prostate Milking.

Slave is used and prostate milked by 5 gorgeous nude masked goddesses for all his sperm.

Lorelei Lee in 'The Black Queen and the Essence of Man'

Lorelei Lee - The Black Queen and the Essence of Man

Part 3 of Kink's cross site Webseries Barbarella: A Kinky Parody. Maitresse Madeline as The Black Queen disciplines Lorelei Lee on the Essence of Man.

Maitresse Madeline in 'A Divine Vacation: FemDom Reality'

Maitresse Madeline - A Divine Vacation: FemDom Reality

Maitresse Madeline beats chastity slave, makes him eat cum from her pussy and strap-on ass bangs him with a bag on his head for her neighbors to see!

Maitresse Madeline in 'EXTREME FEMDOM Prostate Milking Extravaganza!'

Maitresse Madeline - EXTREME FEMDOM Prostate Milking Extravaganza!

Watch Maitresse Madeline savagely humiliate Alex, John, and Ruckus. Each give up their unworthy prostates for a milking extravaganza!

Elyssa Greene in 'Happy Birthday Princess! Enjoy your presents! (part 1)'

Elyssa Greene - Happy Birthday Princess! Enjoy your presents! (part 1)

Pretty presents make for a happy Princess! 2 blonde playthings pitted against each other in devious games.

Maitresse Madeline in 'MILF Destroyed: Filthy Milfy Mommy Cunt'

Maitresse Madeline - MILF Destroyed: Filthy Milfy Mommy Cunt

Perverse employment recruiter Maitresse Madeline dominates desperate MILF housewife Simone Sonay fisting and strap-on ass fucking her MILFy holes!

Maitresse Madeline in '19 year old male gigolo prostate milked for the very first time by Maitresse Madeline!'

Maitresse Madeline - 19 year old male gigolo prostate milked for the very first time by Maitresse Madeline!

Maitresse Madeline hires 19 year old male prostitute and bends him over her knee to spank him then milks his prostate!

Maitresse Madeline in 'Hypnotizing Foot Worship with Maitresse Madeline'

Maitresse Madeline - Hypnotizing Foot Worship with Maitresse Madeline

Maitresse Madeline hypnotizes, teases and milks the cum from foot lovers cock while he gives me orgasm just from sucking her toes!

Maitresse Madeline - POV foot tease masturbation instruction, solo foot masturbation, foot pissing and favorites collecti

POV foot tease masturbation instruction, solo foot masturbation, foot pissing and favorites collecti

Maitresse Madeline in 'Maitresse And the City Part 2: The Hospital'

Maitresse Madeline - Maitresse And the City Part 2: The Hospital

Maitresse milks slaves cock while immobile in a vacu bed and denies him her pussy while he's made to fuck her with a dildo gag.

Gia DiMarco in 'Obsessed foot fanatic punished and made to worship sweaty feet!'

Gia DiMarco - Obsessed foot fanatic punished and made to worship sweaty feet!

Foot fanatic is punished and made to worship sweaty feet then drained of his cum from a tormenting footjob!

Ella Nova - The Pussy Parlor

Massage therapist gets punished and strap-on ass fucked by sadistic lesbian for giving happy endings.

Maitresse Madeline in 'visits famous Midtown Manhattan dungeon!!!'

Maitresse Madeline - visits famous Midtown Manhattan dungeon!!!

Maitresse Madeline travels to notorious Midtown Manhattan dungeon!

Maitresse Madeline in 'Milking the Undertaker: A Divine Bitches Halloween Special!!!'

Maitresse Madeline - Milking the Undertaker: A Divine Bitches Halloween Special!!!

The undead Maitresse Madeline teases, torments, and fucks pervy undertaker Alex Adams as revenge for his depraved ways.

Maitresse Madeline in 'A Soul for a Sole: A Foot Worship Halloween Special'

Maitresse Madeline - A Soul for a Sole: A Foot Worship Halloween Special

Troubled foot fetishist Lance Heart makes a deal with the devil and her minions for the ultimate Halloween foot fantasy!

Maitresse Madeline in 'Whips, Fucks and Teases Fresh Euro Meat'

Maitresse Madeline - Whips, Fucks and Teases Fresh Euro Meat

Maitresse Madeline Whips, Fucks and Teases Fresh Euro Meat

Melody Jordan in 'Lesbian Foot Lab: Maitresse Madeline Submits To Feet!'

Melody Jordan - Lesbian Foot Lab: Maitresse Madeline Submits To Feet!

Maitresse Madeline submits to two foot goddesses worshiping their gorgeous feet and shoving them in her pussy until she cums all over their toes!

Gabrielle Gucci in 'Czech Whores in HELL: Military Debasement'

Gabrielle Gucci - Czech Whores in HELL: Military Debasement

2 Czech sluts try to escape their miserable lives. Maitresse Madeline drills them to see if they are obedient enough to earn a ticket to America.

Maitresse Madeline - Cinderella

Armory guard is made to worship maitresse Madeline's feet and get a teasing footjob!

Maitresse Madeline in 'Click, Pay, Stroke!'

Maitresse Madeline - Click, Pay, Stroke!

Maitresse Madeline dominates you POV while showing you how she would milk your prostate, make you worship her ass and get a tease and denial footjob!

Maitresse Madeline in 'Construction worker ass-fucked and humiliated in the back of a van.'

Maitresse Madeline - Construction worker ass-fucked and humiliated in the back of a van.

Snatched into a van, ass-fucked, humiliated, used up and tossed out.

Maitresse Madeline in 'Una Decisione Suono'

Maitresse Madeline - Una Decisione Suono

Madeline teases & denies slave stroking him with a sound from the inside of his cock & uses her gloved hands on the outside for sensory overload!

Maitresse Madeline in 'Maitresse Madeline's Foot Worship POV!'

Maitresse Madeline - Maitresse Madeline's Foot Worship POV!

Maitresse Madeline seduces 21 year old college student with her feet and makes him loose his hot load all over her feet from a teasing foot job.

Maitresse Madeline in 'FemDom Theatre 2'

Maitresse Madeline - FemDom Theatre 2

Maitresse Madeline & a group of her friends make a slave cum without touching his cock and massaging his prostate at a femdom theatre!

Maitresse Madeline in 'Maison De La Maitresse: A Brutal Cuckold Fantasy! WARNING: Not for the faint of heart!'

Maitresse Madeline - Maison De La Maitresse: A Brutal Cuckold Fantasy! WARNING: Not for the faint of heart!

The most brutal cuckold film ever made with Maitresse Madeline getting fucked hard by her bull!

Maitresse Madeline in 'Size 8 12: Maitresse Madeline Gets Fucked!'

Maitresse Madeline - Size 8 12: Maitresse Madeline Gets Fucked!

Maitresse Madeline wanders into a eccentric shoe store seducing the clerk with her perfect 8 1/2 feet and demanding her fuck the shit out of her!

Maitresse Madeline in 'Submission Of Sasha Knox'

Maitresse Madeline - Submission Of Sasha Knox

Submissive lesbian slut submits to Maitresse Madeline in a tough lesbian domination movie with orgasms from heavy spanking and flogging.

Maitresse Madeline - FemDom Predator

Maitresse Madeline seduces random stranger in men's restroom, fist fucking him milking his prostate spewing his cum then leaves him in his filth.

Felony in 'Kinky Lesbian Politician: The intern's submission'

Felony - Kinky Lesbian Politician: The intern's submission

High profile politician hires badass lesbian to kidnap her intern to perform filthy lesbian sex and punishment for her sick desires!

Maitresse Madeline in 'Pre med student's virgin ass gets punished and fucked to get into medical university!'

Maitresse Madeline - Pre med student's virgin ass gets punished and fucked to get into medical university!

Virginal pre med student is made to get punished and ass fucked by her lesbian professor to get into med school!

Maitresse Madeline in 'One In A Million...........'

Maitresse Madeline - One In A Million...........

Fan of Maitresse Madeline gets a once in a lifetime chance and has his prostate milked by her.

Maitresse Madeline in '18 Year Old Foot Tortured, Foot Tickle, Foot Job Slut!'

Maitresse Madeline - 18 Year Old Foot Tortured, Foot Tickle, Foot Job Slut!

Fiesty 18 year old has her feet tied and tickled, tortured and give a hot foot job until her toes are covered in cum!

Aiden Starr in 'The Divine Bitches Corporation takes over LIVE!!'

Aiden Starr - The Divine Bitches Corporation takes over LIVE!!

The Divine Bitches corporation takes over a failing company punishing the corporate scum with humiliation, spanking , bisexual punishment and denial p

Maitresse Madeline in 'searches for a personal slave for her home.'

Maitresse Madeline - searches for a personal slave for her home.

Slave wannabe applies for Maitresse Madeline's personal home slave and fails miserably. Prostate milking with ruined orgasm and orgasm denial!

Syren de Mer in 'Happy Birthday Princess Donna!! FILTHY ANAL FUCK FEST (Part Two)'

Syren de Mer - Happy Birthday Princess Donna!! FILTHY ANAL FUCK FEST (Part Two)

Syren and Simone continue their depraved submission to the rowdy crowd as Donna decides to use Zander's dick for her very own BIRTHDAY FUCK!!

Maitresse Madeline in 'Two lingerie models get punished and fucked by Maitresse Madeline'

Maitresse Madeline - Two lingerie models get punished and fucked by Maitresse Madeline

2 sexy lingerie models, Dani Daniels and Ana Morna are dominated, punished and fucked by Maitresse Madeline.

Courtney Cummz in 'BONUS!!! Promo photo shoot turned BDSM scene with Courtney Cummz!'

Courtney Cummz - BONUS!!! Promo photo shoot turned BDSM scene with Courtney Cummz!

Courtney Cummz gets surprised dominated by Maitresse Madeline doing things she has NEVER done before in her entire career!

Maitresse Madeline in 'Milked To The Very Last Drop!'

Maitresse Madeline - Milked To The Very Last Drop!

3 of the sexiest femdoms in history keep a male slave locked away in a pit and bring him out once a day to milk his prostate and fill a bucket with cu

Maitresse Madeline in 'A Convent Of Foot Sinners: Footsploitation, Nunsploitation, Blasphemy and FULL FOOTING!'

Maitresse Madeline - A Convent Of Foot Sinners: Footsploitation, Nunsploitation, Blasphemy and FULL FOOTING!

2 nuns live in a world of sinful foot worship taboo & fuck each others pussies & asses with their feet! Includes FULL FOOTING & squirting on toes!

Gia DiMarco in 'Gia Dimarco Completely Destroyed By Three Dominatrix!'

Gia DiMarco - Gia Dimarco Completely Destroyed By Three Dominatrix!

Gia Dimarco taken down & destroyed by three evil dominatrix with fisting in suspension bondage, squirting & an evil caning while strap-on ass fucked!

Maitresse Madeline in 'BONUS FOOT FETISH FEATURE! From FootWorship.com!'

Maitresse Madeline - BONUS FOOT FETISH FEATURE! From FootWorship.com!

A goofy bellhop is made to worship, lick, suck, sniff and clean a gorgeous guests feet and then she gives him a oily foot job and makes him lick her f

Aiden Starr in 'CAUTION: EXTREME FEMDOM HUMILIATION! Live SissyBisexual humiliation'

Aiden Starr - CAUTION: EXTREME FEMDOM HUMILIATION! Live SissyBisexual humiliation

EXTREME FEMDOM HUMILIATION with live sissification with bisexual humiliation, extreme pegging and whipping.

Claire Robbins in 'Dirty Confessions: Live Lesbian BDSM'

Claire Robbins - Dirty Confessions: Live Lesbian BDSM

Cute redhead dominated by fierce redheaded lesbian dominatrix whipping her to orgasm with the sybian and strap-on fucking her ass deep.

Maitresse Madeline in 'Sissification and Humiliation'

Maitresse Madeline - Sissification and Humiliation

Maitresse Madeline totally humiliates slave with full feminization then trains him to service cock and pussy for a party while fucking him in the ass.

Syren de Mer in 'Happy Birthday Princess Donna!! BOW TO THE CATTLE PROD!!! (Part One)'

Syren de Mer - Happy Birthday Princess Donna!! BOW TO THE CATTLE PROD!!! (Part One)

HAPPY BIRTHDAY, PRINCESS!!! Princess Donna tests the perverted loyalties of her subjects with her CATTLE PROD. Beg for it, BITCHES!!

Maitresse Madeline in 'New Submissive Slut: Bailey Blue'

Maitresse Madeline - New Submissive Slut: Bailey Blue

Sexy new comer Bailey Blue is taught the ropes for lesbian BDSM with sadistic bitch Maitresse Madeline.

Maitresse Madeline in 'The Last Prostate Ever Milked On Earth'

Maitresse Madeline - The Last Prostate Ever Milked On Earth

Maitresse Madeline teases slave with her mouth, pussy and handjob then denying him, then milking his prostate till prostate fluid oozes from his cock!

Penny Pax - Let Them Eat Feet!

The queen of foot fetish uses her servant for lesbian foot fetish sex with cake crushing, foot worship, anal sex while licking feet, hot foot bondage!

Maitresse Madeline in 'Bailey Blue: Destroyed by Electrosex'

Maitresse Madeline - Bailey Blue: Destroyed by Electrosex

Maitresse Madeline destroys Bailey Blue with electrosex and the help of a very special male guest.

Annika in 'Sexy submissive lifestyler suffers with rough and kinky lesbian sex!'

Annika - Sexy submissive lifestyler suffers with rough and kinky lesbian sex!

Sexy submissive lifestyler suffers beautifully with rough and kinky lesbian sex and and anal pounding!

Maitresse Madeline in 'Room 417: The Foot Fetishist'

Maitresse Madeline - Room 417: The Foot Fetishist

Maitresse Madeline checks into swanky hotel seducing bellhop with her feet demanding foot worship then steals the cum from his cock with a footjob!

Maitresse Madeline in 'Babes In Toeland'

Maitresse Madeline - Babes In Toeland

Maitresse Madeline and Bobbi Starr demand a begging foot fetishist to sniff, lick and suck their dirty boots, socks and feet and give him a spit cover

Maitresse Madeline in 'The Stalking of Chanel Preston: An Electrosluts Feature'

Maitresse Madeline - The Stalking of Chanel Preston: An Electrosluts Feature

Chanel Preston sub to the Electro hands of Maitresse Madeline and completely give in to her powerful seduction.

Maitresse Madeline in 'Bonnie Day: Masochist Anal Slut'

Maitresse Madeline - Bonnie Day: Masochist Anal Slut

Maitresse Madeline punishes, suspends and ass fucks all natural adorable local masochist girl giving her a full day of lesbian BDSM and hardcore sex.

Maitresse Madeline in 'Kiss My Feet Deadly'

Maitresse Madeline - Kiss My Feet Deadly

Femme Fatale, Maitresse Madeline seductively uses her foot slave for toe sucking, trampling, toe spreading induced orgasms and a hot oiled footjob!

Maitresse Madeline in 'A Very Long Milking: Episode 1'

Maitresse Madeline - A Very Long Milking: Episode 1

Maitresse Madeline declares slave the official Divine Meat for the Bitches to pass around and milks his prostate and makes him lick her asshole clean.

Maitresse Madeline in 'LIVE and PUBLIC slave humiliation, degradation, prostate milking with horny sadistic women!'

Maitresse Madeline - LIVE and PUBLIC slave humiliation, degradation, prostate milking with horny sadistic women!

Room full of wicked femdoms party it up and destroy three lucky slaveboys in public!

Maitresse Madeline in 'The Doctor Is In'

Maitresse Madeline - The Doctor Is In

Two kinky doctors buy a prostitute and do sadistic and kinky sexual medical fetish experiments on her and have multiple orgasms!

Maitresse Madeline in 'The Prostate Milking Queen'

Maitresse Madeline - The Prostate Milking Queen

Maitresse Madeline milks slaveboy's prostate making him ooze milky white cum uncontrollably and without touching his cock!

Francesca Le in 'Porn Star Royalty: Francesca Le'

Francesca Le - Porn Star Royalty: Francesca Le

Maitresse Madeline gives Francesca Le no breaks and dominates and fucks her with tough lesbian bondage and hot strap-on ass fucking!

Maitresse Madeline in 'Sadistic Cock Tease'

Maitresse Madeline - Sadistic Cock Tease

Maitresse Madeline pushes new slaves buttons with heavy corporal, wicked prostate milking and painful tease and denial.

Ashley Jane - The Girls Next Door

Two kinky blonde lesbians take advantage of the girl next door, tying her up, shocking her cunt, and using her mouth to clean their pussies and asses

Maitresse Madeline in 'Maid Humiliation'

Maitresse Madeline - Maid Humiliation

When Maitresse Madeline's maid fucks up in front of company she is punished and humiliated by three rich bitches

Ariel X in 'Maitresse Madeline Pushes Tough and Sexy Ariel X to her Electro Limits!!!!'

Ariel X - Maitresse Madeline Pushes Tough and Sexy Ariel X to her Electro Limits!!!!

Maitresse Madeline goes nuts on Ariel X, who is tormented by cattle prods, sticky pads and metal probes!

Angell Summers in 'Fist Fucking The Lawyer'

Angell Summers - Fist Fucking The Lawyer

Sexy lesbian prisoner dominates, punishes and fist fucks her hot lawyer!

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!!!!

Maitresse Madeline in 'Calico returns for first lesbian double penetration!'

Maitresse Madeline - Calico returns for first lesbian double penetration!

Calico returns dominated and fisted then does her first lesbian double penetration with Maitresse Madeline & Skin Diamond

Maitresse Madeline in 'returns with a vengeance!'

Maitresse Madeline - returns with a vengeance!

Maitresse Madeline punishes and milks slave prostate with expert precision making him loose his filthy load twice without stroking his cock.

Tia Ling in 'Maitresse Madeline and Tia Ling: A Three Year Reunion!'

Tia Ling - Maitresse Madeline and Tia Ling: A Three Year Reunion!

Maitresse Madeline dominates tough submissive Tia Ling in an explosive brutal yet erotic lesbian BDSM update!

Alani Pi - Bobbi Starr and Maitresse Madeline Break Down Two Blonde Sluts LIVE in the Brand New Electrosluts Set!

Bobbi Starr & Maitresse Madeline Unveil the New Electrosluts Set by Breaking Two Blonde Sluts for Electro

Maitresse Madeline - The Maid

Powerful lesbian femdom catches her maid stealing and makes her pay her debts with sexual servitude

Ashley Fires - Medical Testing

Micah Moore has sexy science experiments performed on her by two hot doms!

Maitresse Madeline in 'Maitresse Madeline's Small Penis Humiliation POV Bonus Teaser'

Maitresse Madeline - Maitresse Madeline's Small Penis Humiliation POV Bonus Teaser

Maitresse Madeline usesmall penis humilation to remind you what an inadaquate pindick you are POV style!

Maitresse Madeline in 'Maitresse Madeline's POV foot fetish teaser BONUS!'

Maitresse Madeline - Maitresse Madeline's POV foot fetish teaser BONUS!

Maitresse Madeline's solo foot fetish POV teaser.

Lily LaBeau - Maitresse Madeline and Bobbi Starr unite to destroy two hot blondes LIVE on Whipped Ass!

Maitresse Madeline and Bobbi Starr unite to destroy two hot blondes LIVE on Whipped Ass!

Princess Donna Dolore in 'Maitresse Madeline, Princess Donna and Isis love., captured and bound. The Daddy's Back trailer.'

Princess Donna Dolore - Maitresse Madeline, Princess Donna and Isis love., captured and bound. The Daddy's Back trailer.

This 2 minute Trailer was created to promote Matt Williams return to Hogtied after a 2yr hiatus. Maitresse Madeline, Princess Donna & Isis Love star.

Isis Love in 'CLASSIC ARCHIVE SHOOT! Slaveboy For Dinner!'

Isis Love - CLASSIC ARCHIVE SHOOT! Slaveboy For Dinner!

Two sexy dominatrices use a piece of slaveboy meat to get off then completely tease and deny him pleasure and release!

Tia Ling in 'CLASSIC ARCHIVE SHOOT! Tia Ling's first time and Maitresse Madeline's second time at the Armory EVER!'

Tia Ling - CLASSIC ARCHIVE SHOOT! Tia Ling's first time and Maitresse Madeline's second time at the Armory EVER!

Hot Asian in Lesbian BDSM action.

DragonLily - LAMENT: A Ghost Story

3 dominant bitches come back from the dead to haunt ex-boyfriend by humiliation, tease & denial, strap-on butt fucking & have aggressive sex with him.

Maitresse Madeline in 'Kinky Nurses LIVE!'

Maitresse Madeline - Kinky Nurses LIVE!

A kinky lesbian nurse takes advantage of her assistant with extremely intense lesbian bdsm and hardcore medical fetish sex!

Maitresse Madeline in 'A Very Cherry Wedding'

Maitresse Madeline - A Very Cherry Wedding

Cherry Torn gets hijacked by her bridesmaids bound, ripped from her wedding dress humiliated, punished and double penetrated and left in a pile of cum

Maitresse Madeline in 'Erotic Humiliation'

Maitresse Madeline - Erotic Humiliation

Maitresse Madeline transforms a rough and tumble guy from New Jersey into a perfect little sissy slut maid to perform dirty sex acts!

Melina Mason in 'Second Times A Charm: Melina Mason'

Melina Mason - Second Times A Charm: Melina Mason

Curvy 20 year old is pushed to her threshold and fucked by Maitresse Madeline having the best sexual experience of her life.

Lorelei Lee in 'Visual Sensation: CFNM FemDom Theatre'

Lorelei Lee - Visual Sensation: CFNM FemDom Theatre

3 hot dominatrices milk surferboys cock and prostate till he doesn't know whether to scream cum or piss!

Maitresse Madeline in 'Lesbian Virgin: Sophia Lauryn'

Maitresse Madeline - Lesbian Virgin: Sophia Lauryn

19 year old lesbian virgin is bound, whipped, made to worship feet and strap-on fucked to orgasm by Maitresse Madeline

Asphyxia Noir in 'Los Angeles Fetish Doll'

Asphyxia Noir - Los Angeles Fetish Doll

Fetish model is completely destroyed by two sadistic dommes and gets strap-on fucked with two dildos in her pussy at once!

Maitresse Madeline - Just The Tip

Maitresse Madeline tease and denies hot slaveboy by letting him fuck her pussy with only the tip of his cock.

Maitresse Madeline in 'Where In The World Is Rain Degrey'

Maitresse Madeline - Where In The World Is Rain Degrey

Seductive lesbian dominatrix boss makes her employee into her plaything for the day with fisting, foot licking, pussy licking & strap-on ass fucking.

Audrey Rose in 'Adorable math major takes a break from abstract alegbra to be brutally fucked by Maitresse Madeline!'

Audrey Rose - Adorable math major takes a break from abstract alegbra to be brutally fucked by Maitresse Madeline!

Local college math major takes a break from algebra to be dominated, used, have her pussy licked, fucked in the ass and made to worship another woman.

Bobbi Starr in '40 women gangbang slaveboy for Bobbi Starr's birthday LIVE and PUBLIC!'

Bobbi Starr - 40 women gangbang slaveboy for Bobbi Starr's birthday LIVE and PUBLIC!

40 women gang bang slaveboy's ass for Bobbi Starr's birthday soiree LIVE and PUBLIC!

Maitresse Madeline in 'Foot Fetish Extreme'

Maitresse Madeline - Foot Fetish Extreme

Footslave is made to worship, sniff and clean two hot dominatrix sweaty beautiful feet while spanked and enduring CBT with a final kinky footjob.

Sophie Monroe in 'Day 3 - dolly meats Princess Donna and Maitresse Madeline Take Their Turn'

Sophie Monroe - Day 3 - dolly meats Princess Donna and Maitresse Madeline Take Their Turn

Maitresse Madeline, Princess Donna, and The Pope take turns putting dolly through their versions of hell!

Maitresse Madeline in 'Ode to Men In Pain Part 2: The Madeline Era'

Maitresse Madeline - Ode to Men In Pain Part 2: The Madeline Era

Whipping, small penis humiliation, foot licking, ass worship, CFNM, pegging and tease & denial with Maitresse Madeline and a piece of slavemeat.

Dia Zerva - Farewell Dia Zerva

Dia Zerva submits one last time on film, getting brutally whipped, made to lick ass and feet, suspended then tickled and ass fucked to orgasm.

Maitresse Madeline in 'A CLASSIC FAVORITE: Vendetta in the Wall!!! Maitresse Madeline's'

Maitresse Madeline - A CLASSIC FAVORITE: Vendetta in the Wall!!! Maitresse Madeline's

Maitresse Madeline gives Vendetta an extreme caning and a strap-on fucking of a life time!

Maitresse Madeline in 'New Slaveboy Tryouts LIVE with Maitresse Madeline'

Maitresse Madeline - New Slaveboy Tryouts LIVE with Maitresse Madeline

Maitresse Madeline turns out three newbie pieces of meat with CBT, CFNM humiliation, strap-on ass fucking, ass worship and tease and denial!

Nyomi Banxxx in 'Cute red head plucked off the street hung upside down and double penetrated!'

Nyomi Banxxx - Cute red head plucked off the street hung upside down and double penetrated!

Aiden Starr, Nyomi Banxxx & Maitresse Madeline pluck a redhead off the street then punish, humiliate and double penetrate her to orgasm after orgasm!

Bobbi Starr in 'A Man With Three Balls Means One For Each Domme!'

Bobbi Starr - A Man With Three Balls Means One For Each Domme!

Dude with 3 balls is abducted off the street by girl gang then painfully milked to see if a man with 3 balls produces more cum than the average Joe.

Kristina Rose in 'Whipped Ass LIVE in December'

Kristina Rose - Whipped Ass LIVE in December

Porn star Kristina Rose and amateur Missy Minx are whipped, plugged, clamped and butt fucked into submission by Maitresse Madeline live.

Maitresse Madeline - Yearning Slut

Slut seeks out Maitresse Madeline for a day filled with spanking, tit torture, humiliation, punishment and a strap-on ass fucking pile driver.

Maitresse Madeline in 'Examining The Teachers Pet: Episode 5 Eat your cum for me bitch'

Maitresse Madeline - Examining The Teachers Pet: Episode 5 Eat your cum for me bitch

Maitresse Madeline covers slaves cock with a cock extending cock sheath, fucks it and humiliates him about how he would never feel her pussy.

Maitresse Madeline in 'A Divine Holiday LIVE!'

Maitresse Madeline - A Divine Holiday LIVE!

Maitresse gives one of her world famous teasing handjobs edging slave over and over again until he blows his load without her even touching his cock!

Gia DiMarco - Maitresse Madeline cuckolds her boyfriend with a woman!

Maitresse Madeline cuckolds her boyfriend with a woman!

Maitresse Madeline in 'Educating a Bitchboy: Episode 5 Ultimate Denial'

Maitresse Madeline - Educating a Bitchboy: Episode 5 Ultimate Denial

Slaveboy strap-on fucked in humiliating pile driver while locked in chastity and brutally teased and denied!

Chloe Camilla in 'La Seduction de Chloe Camilla'

Chloe Camilla - La Seduction de Chloe Camilla

Three lesbian witches use seduction witchcraft & BDSM in order to seduce a lesbian virgin into a world of pain, punishment and hot lesbian fetish sex!

Lorelei Lee - Subbing Is In The Air

Lorelei Lee is reduced to common whore status and dominated by Maitresse Madeline

Maitresse Madeline - Mean Girls Club

Porn Star Mckenzie Lee is a sexy co-ed who gets dominated and fucked deep in all her holes by Maitresse Madeline.

Maitresse Madeline in 'and Aiden Starr's Divine B-day Bash LIVE and PUBLIC!'

Maitresse Madeline - and Aiden Starr's Divine B-day Bash LIVE and PUBLIC!

Maitresse Madeline invites 40 local girls, from San Francisco, to The Armory to humiliate, punish and gang bang a male stripper for her birthday

Maitresse Madeline in 'More Cheering, Less Slacking'

Maitresse Madeline - More Cheering, Less Slacking

Coach Madeline corners a cheer leader in the locker room and fucks her brains out with electricity!

Maitresse Madeline in 'The Sexy Cat Burglar'

Maitresse Madeline - The Sexy Cat Burglar

Newcomer Brooklyn Lee gets punished & fucked deep in her ass by Maitresse Madeline only two weeks into her porn career in a sexy cop/burglar roleplay!

Maitresse Madeline in 'Madeline the Mind Fucker'

Maitresse Madeline - Madeline the Mind Fucker

David confesses his masturbation fantasies to Maitresse Madeline and she takes advantage of his weaknesses with humiliation, strap-on and chastity.

Princess Donna Dolore in 'Maitresse Madeline PUNISHED and FUCKED and hazed in as director of Whipped Ass by Princess Donna!'

Princess Donna Dolore - Maitresse Madeline PUNISHED and FUCKED and hazed in as director of Whipped Ass by Princess Donna!

Maitresse Madeline bound, humiliated, fucked and hazed in as director of Whippedass.com

Vivienne Del Rio - Lesbian Revenge

Two lesbian bitches abuse and fuck an innocent bartender when they are thrown in prison they get a taste of lesbian punishment and sex!

Maitresse Madeline in 'Milking Raw Multiple Orgasms'

Maitresse Madeline - Milking Raw Multiple Orgasms

Maitresse Madeline slaps a cock sheath on a horny slave to fuck. When he blows his load inside the cock sheath she makes it her goal to make him pay!

Gia DiMarco in 'Whipped Ass LIVE in June'

Gia DiMarco - Whipped Ass LIVE in June

Hot hard bodied slut gets punished, abused and ass fucked by Maitresse Madeline LIVE for Whipped Ass members!

Mellanie Monroe in 'Big Tits, Big Ass, Big Orgasms'

Mellanie Monroe - Big Tits, Big Ass, Big Orgasms

Big titted milf gets punished and fucked by Maitresse Madeline

Maitresse Madeline in 'Kink.com's wardrobe stylist punished and ass fucked by Maitresse Madeline!'

Maitresse Madeline - Kink.com's wardrobe stylist punished and ass fucked by Maitresse Madeline!

Kink.com's wardrobe stylist is punished and fucked deep in the ass by Maitresse Madeline

Maitresse Madeline in 'June's Divine Live Show'

Maitresse Madeline - June's Divine Live Show

Maitresse Madeline, Goddess Isis Love and Mistress Bobbi Starr are worshiped and dish out sadistic femdom action to three worthless slaveboys in June'

Maitresse Madeline in 'Foot freak gets heavy punishment!'

Maitresse Madeline - Foot freak gets heavy punishment!

Foot freak gets caught masturbating in a shoe boutique. Sexy sadistic shop girl foot teases, punishes, humiliates and buttfucks him in bondage.

Aurora Snow - Marina Babe

Aurora Snow is tied up, spanked, then ass fucked till she's gapping by sadistic domme Maitresse Madeline.

Krystal Main in '1 Blonde, 1 Brunette, 1 Redhead equals Hot Lesbian Punishment and Sex!'

Krystal Main - 1 Blonde, 1 Brunette, 1 Redhead equals Hot Lesbian Punishment and Sex!

A smokin hot blonde, smoldering brunette and fiery redhead get together for a day of intense lesbian BDSM and girl on girl sex!

Maitresse Madeline - FEMDOM 2.0

Veteran slaveboy shows his devotion to his mistress with self-flagellation, enduring CBT, predicament bondage and tease and denial.

Maitresse Madeline in 'Whipped Ass Academy for Wayward Girls Holly's Reform'

Maitresse Madeline - Whipped Ass Academy for Wayward Girls Holly's Reform

Disobedient slavegirl punished, spanked, and fucked deep in her ass till she cums like a bitch in heat!

Maitresse Madeline in 'The Making of a Dominant: Episode 2 Reality Check'

Maitresse Madeline - The Making of a Dominant: Episode 2 Reality Check

Sadistic domme milks slaveboys prostate till he ruins his own orgasm!

Aiden Starr in 'Divine Slave Battle LIVE!'

Aiden Starr - Divine Slave Battle LIVE!

Maitresse Madeline and Aiden Star pit to pathetic worms against each other in the slaveboy Olympics LIVE!

Maitresse Madeline in 'Training of a Houseboy: Episode 5 Kade's Graduation'

Maitresse Madeline - Training of a Houseboy: Episode 5 Kade's Graduation

Aiden Starr in 'Training of a Houseboy: Episode 4 Objectify'

Aiden Starr - Training of a Houseboy: Episode 4 Objectify

Slaveboy is objectified, fucked and fed his own cum by hot blonde dominatrix!

Maitresse Madeline in 'Student Humiliation'

Maitresse Madeline - Student Humiliation

Hot exotic student gets sexually humiliated by lesbian teacher.

Maitresse Madeline in 'Divine High Tea Party LIVE!'

Maitresse Madeline - Divine High Tea Party LIVE!

6 of the hottest and toughest dominatrixes ever demand worship and sexual service by three lucky slaveboys at Divine Bitches tea party LIVE event!

Maitresse Madeline in 'Three Slaveboys Milked'

Maitresse Madeline - Three Slaveboys Milked

Three pathetic worms are milked and denied by cock milking machines with two evil bitches at the helm!

Maitresse Madeline in 'Merry Christmas Slaveboys! Bonus: Live Divine Bitches Launch Show!'

Maitresse Madeline - Merry Christmas Slaveboys! Bonus: Live Divine Bitches Launch Show!

Maitresse Madeline effortlessly uses and abuses two pathetic worms LIVE all for her own pleasure!

Satine Phoenix in 'The Training of Satine Phoenix, Day Seven'

Satine Phoenix - The Training of Satine Phoenix, Day Seven

Exotic sex slaves training to serve the Upper Floor of the Armory

Maitresse Madeline - Rich Bitch

Rich women made into a prison bitch by sexy officer.

Maitresse Madeline - Rumor Queen

Angelica Saige spreads a rumor about the Head Mistress Madeline and gets called into the office for a some kinky lesbian corrective punishment involvi

Dia Zerva in 'The Training of a Houseboy: Episode 1'

Dia Zerva - The Training of a Houseboy: Episode 1

2 sexy bitches dominant slut boy painfully draining his cock and fucking him up the ass at the same time!

Maitresse Madeline in 'Holly Heart Submits'

Maitresse Madeline - Holly Heart Submits

Busty blond submissive gets dominated, fisted and ass fucked.

Maitresse Madeline in 'Sperm Extraction'

Maitresse Madeline - Sperm Extraction

3 sadistic lesbian scientists use unconventional ways to stimulate patients prostate and potency then drain him of sperm to get impregnated!

Maitresse Madeline in 'Who's the Little Bitch Now'

Maitresse Madeline - Who's the Little Bitch Now

Latex clad dominatrix fucks up pain slut and makes him her little bitch then leave his face covered in his own filth!

Maitresse Madeline - Prison Slave

Ass licking prison slut anal fucked by guard and scientist.

Maitresse Madeline in 'Head Mistress Madeline and the Anal Whore'

Maitresse Madeline - Head Mistress Madeline and the Anal Whore

Head Mistress & the Anal Whore

Maitresse Madeline in 'Complete Submission of Kristine'

Maitresse Madeline - Complete Submission of Kristine

The cameras keep rolling as Kristine gets an intense and unusual Whippedass experience.

Krissy Lynn in 'The Modeling Experience'

Krissy Lynn - The Modeling Experience

A young aspiring model tricked into pornography and kinky sex.

Maitresse Madeline in 'The Zucchini Incident'

Maitresse Madeline - The Zucchini Incident

mason gets a zucchini removed from her ass and fisted!

Maitresse Madeline - The Gentle Approach to Heavy Ass Fucking!

The Gentle Approach to Heavy Ass Fucking!

Sarah Shevon in 'Job Applicants Competition'

Sarah Shevon - Job Applicants Competition

Two girls compete for one job in lesbian BDSM..

Maitresse Madeline in '- Orgasms are not given, they are earned'

Maitresse Madeline - - Orgasms are not given, they are earned

M Madeline pussy whips, electrifies and fucks new girl

Maitresse Madeline - Felony

Felony submits to Maitresse Madeline.

Mason Moore in 'Mason Moore: Extreme Rehab'

Mason Moore - Mason Moore: Extreme Rehab

Busty Mason Moore bound and fisted in extreme rehab.

Nina - Crybaby

Nina cries from painful domination by Maitresse Madeline.

Maitresse Madeline in 'Slave Girl Earns a Bed'

Maitresse Madeline - Slave Girl Earns a Bed

Prison girl submits to hard punishment by Dominatrix.

Maitresse Madeline - Nina Returns

Nina returns to Wiredpussy to be dommed by Maitresse Madeline

Satine Phoenix - Satine Phoenix

Lesbian BDSM and strapon sex.

Wenona - Ballerina Sluts

Two Ballerina girls dominated and fucked by lesbian instructor.

Maitresse Madeline - vs Bronte

Maitresse Madeline wires up an innocent sub and shocks her pussy

Maitresse Madeline - Bad Servant

Servant Girl caned and fucked by lesbian.

Maitresse Madeline - The Night Nurse

Blonde girl fisted in bondage by sexy nurse.

Lorelei Lee - Night Club

Busty girl dominated by two badass lesbians in night club.

Syd Blakovich - Interrogation

Syd Blakovich gets interrogated and fucked by three hot doms

Maitresse Madeline in 'Calico Surrenders'

Maitresse Madeline - Calico Surrenders

Sexy girls in real lesbian BDSM.

Maitresse Madeline - Natalie Minx

Busty lesbian sexually dominated in bondage.

Maitresse Madeline in 'makes her debut at Wiredpussy!!!'

Maitresse Madeline - makes her debut at Wiredpussy!!!

January's hot round ass gets spanked and zapped with electricity

Maitresse Madeline - Mina Leigh

Girl next door in extreme lesbian BDSM!

Scenes from other sites featuring Maitresse Madeline,Mirko