Sadistic dominatrix humiliates new ass kissing slaveboy having a field day with his pathetic penis!

Filed under :Painful masochish sessions

Divine Bitch: Mistress January Seraph

Pet: Zak Tyler

I found Zak Tyler when he was poking his head around the Kink.com booth at the Folsum Street Fair. He’s been creaming his pants to serve The Divine Bitches and I thought what the hell let’s give him a shot. He’s the type of slaveboy who’s a complete brownnoser, ass kissing, teachers pet wanna be and oh so much fun to tease and torture. Mistress January Seraph had a field day using him for her pleasure. With Zak’s eager attitude he endured bare handed spanking, caning, CBT, SPH (small penis humiliation), shoe and ass worship and sexual service.

Continue to follow this ass kissing slave’s training with The Divine Bitches and see if his eager attitude will pay off!

Maitresse’s Evaluation

Objectives

  1. submission
    learn his place
  2. protocol
    gain knowledge of house protocol
  3. humility
    curb ego

Closing assessment

  • not extremely egocentric as he stated
  • complete ass kisser
  • more training in humility by way of ass worship
  • pleasure slave potential

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Dominatrix with a big ass smothers slave, puts his dick in a cock crimper while he tries to get hard and drenches him with her squirting pussy!

Filed under :Painful masochish sessions

Jack Hammer has been pleading for the honor to train with the Divine Bitches and be invited to serve on The Upper Floor. Madeline decides to throw him to the dirtiest dominatrix she knows Mistress Flower Tucci! She’s not scared to get her hands dirty and takes on the task of testing Jack out in the dirty bowels of The Armory. Mistress Tucci chews him up, soaks him with her squirting pussy and tortures his cock with a cock crimper. The harder he gets while she teases him with her ass the more it hurts! She uses a rat trap on his balls, fills his ass with an ass hook, smothers him with her big juicy ass and drains his balls till he is left raw and out of breath. It’s safe to say Mistress Tucci puts Jack through the ringer. Will he ever have a chance to get out of the bowels of the dungeon and train with the Divine Bitches? Only Maitresse Madeline can decide his fate!

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Two escorts play with anal toys and get ass fucked!

Filed under :Painful masochish sessions

Bobbi Starr runs an escort service that specializes in anal sex. Seda comes to the service looking for work and receives training from Bobbi on how to please men with her ass. Bobbi then goes with Seda to her first client to make sure she properly pleases. The two girls become dirty anal sluts and get their asses pounded and stretched with toys and cock.

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Bad ass dominatrix hobbles dogboy and reams him in the ass with her fist!

Filed under :Painful masochish sessions

Divine Bitch: Miss Dia Zerva

Dogboy: Derrick P

Dogboy Derrick P has progressed to his second day of training with Divine Bitch Miss Dia Zerva. Maitresse Madeline’s convinced she will never find a proper hellhound to serve her on The Upper Floor. Derrick P is put away in the dog cages of The Armory not knowing when someone will unlock him. When someone finally does it’s drill sergeant Miss Dia. She trains dogboy with flogging and proper pussy licking. When he doesn’t get it right he’s beaten with a rolled up newspaper like dogs often are. Miss Dia stretches dogboys ass with a fist and uses his cock for her pleasure. He fails miserably and is made to eat his own cum off of the rolled up newspaper!

This hot update includes flogging, oral servitude, fisting, cum eating instruction, CFNM and dog boy training!

Don’t miss the rest of dogboy’s training as he continues on to episode 3 at Divine Bitches!

Maitresse’s Evaluation

Objectives

  1. Grace
    learn to have elegance or beauty of form, manner, motion, or action
  2. To be used for entertainment
    train to be fisted for amusement

Closing assessment

  • elegance and form messy and unsure
  • relatively useless cock
  • anal fisting was promising but needs more training
  • still lacks endurance

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Tears and Torments

Filed under :Painful masochish sessions

Tears and Torments
Presented by The Pain Files

Masochist Chaos tied and tit tormented outdoor in the barn. The blonde slavegirl is crying from the cruel pain inflicted on her sensitive nipples. Her devious bondage restraints leaves her wriggling helplessly suspended from the beams, whilst her tits endure severe torments.

Tears and Torments

Tears and Torments

Blonde sub Chaos is a british submissive with a love of intense SADO and deep brunette humiliation games. Watch as she is being taken to the old barn for spanking and pain. See more at The Pain Files

Tears and Torments

Tears and Torments

See all of Painslave Chaos in BDSM and Pain at: The Pain Files


Madison Scott bound and fucked by Felony.

Filed under :Painful masochish sessions

Madison Scott goes to an agency to get work as a model for movies and TV. Felony, the shady agent, has alternative plans for innocent Madison which involve the power of persuasion, rope, steel devices, a big strapon cock and ass licking.

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Sammi caught with Mistress Kendra’s toys in her ass, again.

Filed under :Painful masochish sessions

Sammi was an anal slut while at college & is still an anal slut today… Been years since Sammi was using Kendra’s toys in the dark dorm rooms of the University but she knows that when she is invited to visit her old room mate, she will have loads of anal fun! Caught once again shoving Kendra’s toys up her ass, Sammi finds that Mistress Kendra has grown a dark side and makes her pay for their use.

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Busty Submissive in Pain

Filed under :Painful masochish sessions

Presented by The Pain Files
Featuring Masochist Cherry

Busty blonde blindfolded fetish masochist Cherrys bondage tit torments and sado pussy pain. Blonde british fetishmodel and lifestyle sub Cherry securely tied, gagged and caned on her bare bottom.

Slavegirl Cherry

Slavegirl Cherry

Painslut Cherry – Presented by The Pain Files

Cherrys huge tits are put in biting bondage and painfully metal clamped – followed by a thorough hotwaxing. Cherry is blindfolded and securely bound up, her huge udders in tight bondage and hotwaxed. Her innocent pussy is clamped. The gagged cuties disciplinary BDSM training session continues with multiple pegs place on her tits and pussy. The blindfolded beauty has tears in her eyes when the session is finally concluded.


Exotic Submissive Michiko

Filed under :Painful masochish sessions

Starring Masochist Michiko

Presented by The Pain Files

Pretty eastern slavegirl Michiko chained to a wooden cross and painfully pegged on her tits and nipples, inner thighs and pussy.

Asian Slavegirl

The pegs are pulled and toyed with – and finally pulled off – leaving the poor painslut screaming and in tears.

Asian Slavegirl

To see more of Painslut Michiko: Visit The Pain Files
Real slavegirls in real pain and tears
Extreme SADO and Pain


Dana DeArmond and Gia DiMarco worship one another’s perfect ass.

Filed under :Painful masochish sessions

Dana and Gia are two very beautiful, very dirty young women. These filthy lovelies had never met before, so we let them spend some time getting to know each other. Turns out they have a lot in common: they are both hot-ass anal whores.

Watch as these two sluts explore one another’s firm and gorgeous ass. Gia really opens up in bondage, chained to the ceiling she lets Dana know some of her likes and dislikes: moaning when Dana puts a hand up her pussy, coming when Dana pushes beads up her tight asshole. We can tell Dana’s into Gia, showing off for her by fisting her own ass. Gia is so impressed, she fucks Dana’s ass with a dildo gag, so she can get a closer look at that asshole open and close.

Dana ties Gia up for her first strap-on ass-fucking. Gia warms up Dana’s cock with her hungry wet mouth. By the last scene, these girls are like old friends, happy, tired and dripping cum.

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