Man Made into Woman by Roommate as Punishment 76 sec

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Guy Transformed into Hot Babe as Punishment by Female Roommate 68 sec

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Guy Transformed into Hot Woman as Punishment by Roommate 69 sec

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She Made Her Male Roommate Dress as Hot Woman and Get Fucked as Punishment 7 min

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Friend Transforms Male Into Woman as Punishment 73 sec

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Friend Dominates and Transformed Male into Woman as Punishment 6 min

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Anal Punishment for Christmas 2 min

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Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm 8 min

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Inverted Chastity & Candle Wax Go Together Like PB & J, Yay! 7 min

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Dommes in Heels Punish Innocent Trans Catgirl 30 sec

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Sissy Squirts Cum hard in Chastity Cage With Vibrator Jessica Bloom 6 min

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Anal Stretching Routine Training for Sissy (Part 1) 11 min

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Sissy inserts chile jalapeño inside ass! (Extremely painful) 6 min

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Sissy got some serious anal pounding with Easter Eggs!! (part 2) 8 min

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EStim in Chastity 2 8 min

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