This fantasy roleplay shoot is an ode to sexploitation, women in prison, revenge plot movies. Ariel X gets popped for roughing up an innocent bartender while her accomplice Princess Donna Dolore leaves her high and dry. Shes placed in a womens correctional facility and subjected to heavy lesbian punishment by warden Maitresse Madeline. Bondage in chains, singletail, spanking, foot worship, ass licking, nipple torture, strap-on fucking, anal sex and humiliation are all included. When Maitresse Madeline brings in a new psychiatrist who has unconventional ways of rehabilitating the female prisoners she is more than meets the eye and the plot thickens!
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Her First Punishment

When girls think that they can get away with whatever they want in Russia, they're quickly brought to the realization that their behavior won't go unpunished! See them learn their lessons here at Her First Punishment, where these bad Russian babes are bent over and spanked, paddled, whipped and flogged until they realize the error of their ways, and until their asses are sore and purple.

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Perfect Spanking

Submissive babes who get out of line soon realize that there's only one way to right the ship when it comes to their attitude, and that's via a firm, relentless smacking of their behinds! At Perfect Spanking, these chicks are in for the punishment of their lives, as they get put over the knees of men or women, get their panties pulled down, and take hands, paddles, canes and more to their butts.

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Corner time and caning for two school girls - hot welts and swollen cheeks
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Young schoolgirl on all fours with her pert bottom in the air
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Stunning brunette strapped to the bench for brutal caning on her bare bottom - tears of pain

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Russian schoolgirl is spanked to tears with a highly monstrous wooden paddle
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Clown School Spankings
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and submission but comes with an eagerness to learn and please. Maitresse Madeline shows Bailey the ropes and teaches her that all little pain sluts have to start at her feet. Bailey takes gloved OTK spankings, evil zipper, pussy torture and is made to lick Madeline's pussy to earn a deep strap-on anal fuck!
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and submission but comes with an eagerness to learn and please. Maitresse Madeline shows Bailey the ropes and teaches her that all little pain sluts have to start at her feet. Bailey takes gloved OTK spankings, evil zipper, pussy torture and is made to lick Madeline's pussy to earn a deep strap-on anal fuck!
Brutal Vintage Spanking
Brutal Vintage Spanking
Our guy hits hard on the blondes white panties. Then a woman gets in on the act and takes her licks.
Our guy hits hard on the blondes white panties. Then a woman gets in on the act and takes her licks.

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This fantasy roleplay shoot is an ode to sexploitation, women in prison, revenge plot movies. Ariel X gets popped for roughing up an innocent bartender while her accomplice Princess Donna Dolore leaves her high and dry. Shes placed in a womens correctional facility and subjected to heavy lesbian punishment by warden Maitresse Madeline. Bondage in chains, singletail, spanking, foot worship, ass licking, nipple torture, strap-on fucking, anal sex and humiliation are all included. When Maitresse Madeline brings in a new psychiatrist who has unconventional ways of rehabilitating the female prisoners she is more than meets the eye and the plot thickens!

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