Tag Archives: Sarah Gregory

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 …

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 …

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 …

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 …

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 …

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 …

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 …

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 …

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 …

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 …