Tag Archives: Sarah Gregory

Lily Swan makes a return to prison where the introduction to her long sentence behind bars is a judicial caning punishment. Alongside Lily is new inmate, Delta hauser, found guilty …

This is a special custom prison punishment film that is over 2 hours in length, showing the build-up and detailed intake, processing, and discipline including the aftermath shots of all …

In this special custom film, Audrey and her friend Sarah have been left alone and in a position of trust for a long weekend while Sarah’s stepdad goes on a …

Anastasia Rose learns firsthand the sheer humiliation of a wheelbarrow spanking at the merciless hands of Sarah Gregory. The poor girl is utterly unprepared for just how exposed and degrading …

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 …

We are very excited to welcome Matlida Caesar to MommaSpankings in this bedtime spanking film alongside Sarah Gregory. Sarah is a guest in Matlida and Miss Iceni’s home as an …

When gentle reminders fail, sometimes love must sting. I’ve been neglecting my meals, and despite gentle reminders, I just couldn’t break the habit. Miss Bernadette, my loving Mommy and Mistress, …

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 …

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 …

In this custom film, Sarah is a naughty schoolgirl who complains that she isn’t feeling well to get out of class. Nurse Bernadette has dealt with this lying behavior from …