This clip was a custom, I was asked to have Ash (Ashley Benson) dressed with a specific style of skirt and in traditional school clothing. She was to be instructed …
Read More »Wayward Girls 9
Ditching school, carousing about town! These girls are in for a rough day… Lily is last to receive a final, hard caning, and she is teary-eyed before we’ve begun! Calling …
Read More »Wayward Girls 8
Ditching school, carousing about town! These girls are in for a rough day… Denise reluctantly drapes herself over my spanking bench, exposing her deeply bruised bottom for eighteen strokes from …
Read More »Housekeepers Discipline – Sarahgregoryspanking
Lady Jose has had enough of Sarah’s sloppy housekeeping. Despite multiple warnings, the dining room remains a dusty disaster. This time, there’s no escape from a well-deserved punishment. Sarah is …
Read More »Prison Disciplinary Triple Caning – Aaaspanking, Sarahgregoryspanking
In this intense custom production, three female inmates – Carissa Dumond, Dani Synclair, and Cara Day – are processed with cold efficiency before being left naked and vulnerable in the …
Read More »My Apartment My Rules – Sarahgregoryspanking
Sarah’s had enough of her roommate Jess’s disrespect! After constant disregard for the rules, Jess’s boyfriend crashing for free, and her friends helping themselves to Sarah’s food and Netflix, it’s …
Read More »Three Miscreants 8
Sadly for these girls, their instructors believe personal discipline is best achieved through severe punishment. “One, thank you Miss.” Bernadette’s creamy thighs are presented for six lashes from my cane. …
Read More »Rachel and Dolly’s Etiquette Lesson – Sarahgregoryspanking
Meet Rachel and Dolly, two spoiled sisters who think they know it all. But when their parents hire the strict and no-nonsense Miss Matthews to teach them a lesson in …
Read More »Head Girl Vs Matron – Sarahgregoryspanking
In this Custom Film, Sarah plays the rebellious head girl and Miss Bernadette the Nurse. Sarah thought faking an illness would get her excused from class – until Nurse Bernadette …
Read More »Matilda Learns Her Lesson – Sarahgregoryspanking
Just hours before the Lake Industries staff holiday party, Matilda’s boss, Mr. Lake, calls her to his hotel room for a private meeting. He’s noticed her lack of focus at …
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