Previously in, The Interview, Sarah was interviewed for a job as Miss Matthews personal assistant. Sarah got the job with flying colors. Now, a month later they are at a …
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Slutty Secretaries Spanked by Boss – Sarahgregoryspanking
Ashley and Sarah are humiliated to find out that their boss, Miss Bernadette, knows that they have been having sex during working hours. There are surveillance cameras at the office …
Read More »Stolen Cheer Routine – Cheerleaderspankings
At this school, it was so large that there were 2 cheer squads for the 2 rival teams. Sarah Gregory had found out that her rivals Lily & Joelle had …
Read More »Pee Pee Princess Punished – ABDL Spanking
This is a special custom film with three main scenes to the story of Ella, the naughty little “pee-pee” princess, who gets punished. Ella arrived home late and StepMommy (Sarah …
Read More »Kajira’s Long Day, Part 4 – Spanking101thevideos
Sassy Kajira Bound is sporting a tender bottom under her jeans after two hard spankings from Momma Sarah Gregory. To make things worse, she also has no panties on under …
Read More »Kajira’s Long Day, Part 2 – Spanking101thevideos
Naughty Kajira Bound’s long day continues as her Step-Mom Sarah Gregory discovers that Kajira didn’t do the laundry, and neither has any panties to wear to school or work. File …
Read More »Kajira’s Long Day, Part 1 – Spanking101thevideos
Naughty Kajira Bound spends a very long day getting soundly spanked by Momma Sarah Gregory and Principal Tubaman. Along the way Momma gets a few spankings of her own. Sassy …
Read More »Hungover and Humiliated – Cheerleaderspankings
Adriana had gone AWOL and missed the game because she had been partying the night before. Coach Gregory eventually found the sleeping brat nursing a huge hangover in a random …
Read More »Sarah’s Foul Mouth Punishment – Mommaspankings
This is another real punishment film featuring Sarah and her scene Step-Mommy, Miss Elizabeth. While they were at Six Flags this past summer, Sarah didn’t use very appropriate language while …
Read More »An intercontinental re-education – Part Eight – Well Spanked Bottom
Sarah’s torment continues with a prolonged hairbrush spanking over Auntie Rose’s knee during detention. Then it is time to fill in the punishment book while she stands on the punishment …
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