Man in Pain

He's a good guy except for the fact he was born male. And that is enough reason for Mistress Harmony to come out and play.

After a fierce whipping on the rusty box spring to put him in his place, Harmony ties his nuts to a leash and spreads her legs, amused watching him nearly rip his balls off trying to get to her pussy. Always hungry for sex, she uses the boy's otherwise useless cock then makes him lick the come off her beautiful pussy.
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Miss Adams dominates Rico the pain slut and Sarah the fuck slut in this very hot MIP update. Featuring, PAIN, electrical play, whipping, clamps, ass fucking with a HUGE strap on and of course a heaping dose of hardcore sex.
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Gwen Diamond gets bored easily, and Billy is not holding her attention lately. Determined to keep herself satisfied, Gwen decides it's time to introduce a little more beef to their relationship, and calls TJ to come give her a good hard fuck while billy is tied tied to a chair, forced to watch.
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It's Johnny's last day of school and Head Mistress Penny Flame stops by the dorm to administer one final lesson. Ass paddling, glory hole CBT, bondage, tit clamps and cum eating are all on the test.
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Mistress Kendra likes to hurt boys. Slave girl Devaun likes to fuck boys. Why not put them together and see what happens?

Sensory overload is the result when Kendra is whipping, clipping, slappping and butt fucking kade as devaun sucks his dick, shoves her ass in his face and fucks him silly.
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She has her hands full with two submissive sluts, but Miss Adams has enough sadism to keep them in check. Kade is a little pain slut and takes a vicious cane and clamp scene. He is quickly made to understand that he is indeed weak and has no control, reinforced with a fierce ass fucking.



Gimp girl is far from safe if she does not impress the Mistress with her cock sucking skills. The little fuck puppet is soon bouncing on the hard cock as Claire pours hot wax all over them both and whips it off.



Miss Adams pushes both these sub's limits and brings them out the other side smiling. Good show, Miss Adams.
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Lefty thought he was a lucky fucker when Samantha Sin walked onto the set to team up with Cassandra Cruz, but these two mean bitches were not impressed with our boy's worthless little prick. Cruelty comes in twos for Lefty and despite his straining hard cock and best efforts, he just gets fucked over as he struggles to please these demanding women. Clothespins, cock sucking, heavy ball weights, dildo gags, whips and a strap on up his ass as he tries to eat Samantha's gorgeous pussy are his reward.



They laugh at him and humiliate his worthless ass for sporting such a tiny prick, then they tease him and use him by fucking his face with their cunts and taking their fill of his pathetic cock in their hungry cunts.



In the end, as the beauties orgasm by themselves and hold Lefty down at the end of a leash, it is clear that they are just not into him and his tiny little prick.
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Isis turns the tables on this pushy office executive when his condescending attitude gets out of hand. She quickly teaches him the meaning of the word humility when she ties him up, beats him and fucks him in the ass. She gets off on her bosses face jammed in her ass and pussy, and finally takes her fill of his miserable cock before forcing him to sign off on raises for all the females in the company.
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Sandra's verbal humiliation is first rate, and today she has 'lefty' eating out of her hand and begging for more. Mistress Sandra's tight latex, tall boots and bitchy demeanor accent lefty's painful screams as he is fucked in the ass with a dick on a stick. As usual his hard cock gets him in more trouble, and he is soon in a predicament that has his balls tied tightly to a weighted line. The more weight he takes, the closer Mistress's mouth and delicious pussy get to his straining cock.



Sufficient begging, pleading and pain get lefty in a situation where Mistress can make good use of his hard cock and dildo-gagged face, and she makes short work of getting off and milking his cock of every ounce of cum.
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Kade thinks he has what it takes to work at Kink.com as a security guard, so we asked gorgeous, 6 foot tall Annette to stop by to help out in his interview. It didn't take long for him to realize that he is sorely lacking in experience, but Annette is quick to illustrate some basics.



After humiliating him and roughing him up the tall German beauty strips him down and puts her strap on up his ass, all the while cursing him out in her thick, sexy accent. Finally he admits the real reason he is applying, to fuck porn stars, and she gives him a little bit more of this than he bargained for.
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You may dream about these two gorgeous ladies dominating and fucking you, but as Lefty can tell you, be careful what you wish for. Being forced to choose who is the hottest is a very difficult proposition, and Lefty pays for his foibles over and over again with pain and humiliation. Predicament bondage, strap on ass fucking, beating, slapping, and hard fucking take this lucky boy to the extremes.
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Beautiful Daphne Rosen is brand new to MIP, and we slated her with pain pig Mr. Rico for a trip to a stuffy convention. When they return to the motel room that nite, Mr. Rico tries his hand at promoting Miss Rosen to Personal secretary, but she has other ideas.



She first canes him into submission then fucks his ass with a HUGE strap on that makes his dick so hard that she orders him to stroke it off while sitting her gorgeous, round ass on his pathetic face. Mr. Rico is HER bitch now.
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Rico is put to the test with this cold hearted bitch! Raven uses CBT, paddling and strap-on ass fucking to torture her slave.
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Nika Noire is relentless on Jack Hammer. She doesn't give him any slack whats so ever and why should she? After all the only reason around is to please her for as long as she feels he is worthy of being in her presence. This update includes heavy flogging, humiliating strap-on ass fucking, ass and pussy worship and one lucky slave who gets to be in the presence of a true sadistic goddess!
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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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    >Week 41 of 2009