Men In Pain

Gwen Diamond and Billy

MIP welcomes a new Femme Domme to the site. Gwen Diamond, Mistress Diamond to you, turns the tables on her low life, invertebrate husband and serves up a lesson he will not soon forget. Little billy is hobbled and made to tear off her stockings and worship her beautiful feet before she allows him the pleasure of sucking her beautiful pussy. She whips him till he pleads for mercy before assaulting his tight asshole with her strap on, spilling his hot cum all over himself.

The chemistry between these two shows in all the hot fucking and domination in this update. Welcome aboard, Mistress Diamond.

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Gwen Diamond and Billy
Gwen Diamond and Billy
Gwen Diamond and Billy
Gwen Diamond and Billy
Serving Simone

Simone Kross has seen it all and she is not amused by this particular slaveboy at all. He tries hard to please her by taking the pain of the single tail followed by nipple torture. When she is still bored of him she decides to get herself off while giving him the luxury of licking and sucking on her toes while he is made to watch. In the end he has the honor of Miss Kross using his cock. She milks this slave dry till he looses releases his load down her thigh!

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Serving Simone
Serving Simone
Serving Simone
Serving Simone
Red Headed Tolerances

The tales of the red-headed reputation are true. Ask Kade about this demanding, sadistic but gorgeous dominatrix. Predicament bondage, strap on ass fucking, whipping, teasing, fucking. All with legs and tons of red hair.

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Red Headed Tolerances
Red Headed Tolerances
Red Headed Tolerances
Red Headed Tolerances
Billy and Gwen Diamond

Gwen Diamond and Little Billy's first MIP pairing revealed such a hot chemistry that we had to have them back for PART TWO - in which Gwen has the bad boy doing chores while wearing her panties under his clothing. To further remind him of his status in the household, she unleashes a very hard whipping on him, humiliates him verbally, suspends and beats him and eventually uses his pathetic cock for her own pleasure. After she finally allows the panty boy to come inside her pussy, she squats on his face and squeezes the sticky goo out all over his mouth and face, laughing at him all the time.

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Billy and Gwen Diamond
Billy and Gwen Diamond
Billy and Gwen Diamond
Billy and Gwen Diamond
Therapy

Daniel's girlfriend thinks he needs therapy to modify his behavior but decides this little whore needs more then traditional therapy. She sends him to a dominatrix instead to whip him into shape! Tina expertly administers pain then bends this slut over invading his tight ass. Rest assured he will be a changed man! In the end she feels his session wouldn't be any fun if she didn't take him for a ride just for her own kicks. Of course this wicked dominatrix takes advantage of the opportunity!

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Therapy
Therapy
Therapy
Therapy
Bitch-boy Hunting

Mistress Harmony Rose has been tasked with screening potential bitch boys for a special project. She examines Dean Strong but gets a litte sidetracked during the evaluation...

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Bitch-boy Hunting
Bitch-boy Hunting
Bitch-boy Hunting
Bitch-boy Hunting
Heavy Bondage and Mind Games

Heavy Bondage Lovers, this update is for you. Throw in some twisted psychological domination and pain play, and we have Miss Adams and Euro at their finest.

Miss Adams is all over Euro like a twisted spider, and has him screaming in pain and thanking her for it at the same time. Euro is suspended, mummified, fucked with a dildo, whipped, gagged and generally broken down to his component parts by the crafty dominatrix, Claire Adams.

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Heavy Bondage and Mind Games
Heavy Bondage and Mind Games
Heavy Bondage and Mind Games
Heavy Bondage and Mind Games
Jordan Takes Her Due

Jordon Dominates

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Jordan Takes Her Due
Jordan Takes Her Due
Jordan Takes Her Due
Jordan Takes Her Due
Gorgeous Red Headed Dominatrix

Wolf takes it like a man while MIP debuts the gorgeous Miss Keen. We lost track of how much weight hung from his balls, but all that pain just blurs into a giant throbbing hard-on anyway. The shrewd sadist knows when to apply painful pressure, and when to capitalize on a Good Thing. Lucky for us Miss Keen is savvy to more than one use for a hard cock.

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Gorgeous Red Headed Dominatrix
Gorgeous Red Headed Dominatrix
Gorgeous Red Headed Dominatrix
Gorgeous Red Headed Dominatrix
Penny And Bill + Kimberlee and Lobo

Penny and Bill + Kimberlee and Lobo

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Penny And Bill + Kimberlee and Lobo
Penny And Bill + Kimberlee and Lobo
Penny And Bill + Kimberlee and Lobo
Penny And Bill + Kimberlee and Lobo
Billy, Sarah Jane Ceylon and Claire Adams

Imagine a world where you are at the mercy of both Mistress Claire Adams and submissive slut Sara Jane Ceylon. Imagine Mistress Adams humiliating you in front of another beautiful woman, then ordering her to tease your cock, fuck you, suck you off and feed your own cum to you from her mouth while you are tied up and helpless. Imagine no more, enter little billy's reality.

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Billy, Sarah Jane Ceylon and Claire Adams
Billy, Sarah Jane Ceylon and Claire Adams
Billy, Sarah Jane Ceylon and Claire Adams
Billy, Sarah Jane Ceylon and Claire Adams
Dominatrix in Red

Yes Miss Madison

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Dominatrix in Red
Dominatrix in Red
Dominatrix in Red
Dominatrix in Red
Beauty and Dogboy

Alluring beauty mixed with a cold heart is just what this dogboy needs to be put in his place. This dominatrix puts her dog through the ringer till he is barking for mercy.

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Beauty and Dogboy
Beauty and Dogboy
Beauty and Dogboy
Beauty and Dogboy
Harmony and Nomad

Latex clad Harmony Rose sinks her teeth into trussed up nomad’s hard, bound cock and he doesn’t know whether to cum or cry for mercy. He is completely helpless as Harmony works him over, fucks him with her strap-on, and eventually pushes eight fingers into his begging, gapping asshole. After stuffing her beautiful, round ass into his mouth and riding his stiff cock with her pussy, she torments him with a latex glove hand job that has him squirming out of his skin.

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Harmony and Nomad
Harmony and Nomad
Harmony and Nomad
Harmony and Nomad
Rick Hunt and Lady Lydia McLane

Latex Goddess Lydia McLane lords her power over slave boy rick as he squirms in an escape attempt from rope bondage while under the laughing Mistresses whip. A chilling sounds scene follows, and Lydia continues her humiliating onslaught by commanding rick to recite 'I like how my little pussy is getting fucked' while reaming out his piss slit with the thick, steel rods. In the end, rick is suspended and fucked in the ass while Lydia strokes her gloved hands over his hard, aching cock. Maybe she will even allow him to come?

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Rick Hunt and Lady Lydia McLane
Rick Hunt and Lady Lydia McLane
Rick Hunt and Lady Lydia McLane
Rick Hunt and Lady Lydia McLane
Annie Cruz and CJ

Militant Mistress Annie Cruz gets new recruit CJ into heavy submission with strict predicament bondage and painful domination. Then, as if inverted suspension in a straitjacket is not enough, Annie clips the mousetraps on his balls to really ramp up the energy before stretching his ass with an inflatable dildo. CJ finally takes it in the ass like a horny [REDACTED] while Mistress Annie teases his raging hard-on in a denial scene that leaves his balls blue and aching for release.

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Annie Cruz and CJ
Annie Cruz and CJ
Annie Cruz and CJ
Annie Cruz and CJ
Training the Basement Slave

Boy in the Boiler

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Training the Basement Slave
Training the Basement Slave
Training the Basement Slave
Training the Basement Slave
Miss Starr Dominates Big Boy's Black Ass

Aiden takes. She never asks. She gags him, ties him, electrocutes him and fucks his wanna-be submissive ass. Then she takes that fat cock right where she loves it most: in her horny dominant pussy.

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Miss Starr Dominates Big Boy's Black Ass
Miss Starr Dominates Big Boy's Black Ass
Miss Starr Dominates Big Boy's Black Ass
Miss Starr Dominates Big Boy's Black Ass
Claire Adams and Patrick Andraste

Claire Adams has a new toy named rubberboy. He comes complete with operating manual, full rubber wardrobe, an assortment of enormous ass toys, and a submissive demeanor conducive to the most sophisticated, sadistic palate.

Miss Adams wastes no time in stretching his ass with a huge, electrified ass plug that firmly confirms his status for the day. Hooded and enclosed in rubbber, he is then worked through several positions that leave him vulnerable and available to the delightfully twisted dominatrix, and she takes full advantage by whipping, slapping, squeezing and fucking his ass with the largest strapon we have ever seen here at MIP.

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Claire Adams and Patrick Andraste
Claire Adams and Patrick Andraste
Claire Adams and Patrick Andraste
Claire Adams and Patrick Andraste
The Fucking Machine

Princess and Stigma

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The Fucking Machine
The Fucking Machine
The Fucking Machine
The Fucking Machine
Bitch Boy in Training

Mistress Penny Flame takes the reins on newbie bitch boy Max Powers and runs him through the ringer starting with a severe caning to his young ass. She then fucks his welted ass with a huge strap on, and makes him roll over and beg for more before finally giving him a taste of her pussy, fucking his cock and feeding him a load of his own cum.

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Bitch Boy in Training
Bitch Boy in Training
Bitch Boy in Training
Bitch Boy in Training
Double Header: Two Gorgeous Females Fuck and Control their Men

Women have all the power. Just ask these two guys.

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Double Header: Two Gorgeous Females Fuck and Control their Men
Double Header: Two Gorgeous Females Fuck and Control their Men
Double Header: Two Gorgeous Females Fuck and Control their Men
Double Header: Two Gorgeous Females Fuck and Control their Men
Lorelei Lee and Diezel

Vin has problems obeying orders and Mistress Lorelei Lee is in charge of extracting his submission. After ripping her stockings he is gagged, hooded and blindfolded in the sweaty nylon till Mistress has better use for him as a fuck toy - first his ass, then his cock. Finally satisfied, Mistress plows his ass with a rubber dildo while milking his hard cock.

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Lorelei Lee and Diezel
Lorelei Lee and Diezel
Lorelei Lee and Diezel
Lorelei Lee and Diezel
Cruel Mistress

She likes to hurt boys like Rico, the little pain sluts who crave it. She says that the power makes her pussy wet. The power to beat the little fucker till he begs for mercy. Power to fuck his little bitch ass with a strap on cock the size of her arm. Power to satisfy her wet pussy on his greedy face or his fat, hard cock. That is power.

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Cruel Mistress
Cruel Mistress
Cruel Mistress
Cruel Mistress

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