Anal MILF Training Holly Heart, Final Day

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Slave trainee Holly Heart is fucked hard in all her slutty holes on TrainingofO… (more…)

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Janice Griffith – Up & Coming Starlet Gives her Pussy to the Machines

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Janice is so fucking hot with her perfect skin, tight body and perky tits… (more…)

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India Summer’s Principles of Servitude, Day Three

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MILF Slave Training: India Summer has the most rockin body, especially when it is tied up and getting fucked hard in the ass… (more…)

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Blond newcomer anti’s up with her Pussy vs. The Machines

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Jenna Ivory is the girl next door type… (more…)

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90 Minutes of Servitude

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When Veruca James signs over 90 minutes of her life to Training of O, we get real time action of the pretty applicant being stripped, tied, interrogated, tested and fucked hard in all holes… (more…)

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The Untrainable Slut, Day Three

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Savannah Fox’s inability to control her own pussy, do her homework, follow the simplest of orders make her untrainable in my book… (more…)

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Special Feature: Anal MILF Training Compilation

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Highlights from the BEST Anal MILF Training Movies!Favorite MILFS Veronica Avluv, Simone Sonay and Holly Heart in the best anal MILF Training scenes that Kink… (more…)

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India Summer’s Principles of Servitude, Day Two

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Gorgeous, horny MILF of the Year India Summer is put into a domestic setting and taken down a notch on her journey to learn her Principles of Servitude… (more…)

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Strict Discipline and Oral Training for Ana Foxxx, Day Two

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Ana Foxx is truly lovely and wants to please… (more…)

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Training That Ass, Savannah Fox, Day Two

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Let me add to my original assessment: not only is she a Voracious Whore, she is an undisciplined, greedy black hole Pain Slut of a Voracious Whore… (more…)

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