Winter is summoned to Coach Gregory’s home after her latest bout of nonsense. This collegiate freshman is on the verge of losing her scholarship if she doesn’t shape up, respect …

When Sarah and Matilda, mischievous stepsisters, attempt to hide their teacher’s letter about their classroom behavior, they think they’ve escaped punishment. But their strict teacher, Miss Zee, takes matters into …

Naughty Cara Day is really sore from two hard spankings by Sarah Gregory and is currently standing in time out with a mouthful of soap. She tattles on Sarah, only …

There’s noting quite as hot as a naughty girl bending over for the paddle. In this compilation, you get five gorgeous women bending over and getting their bottoms paddled hard! …

Matilda is supposed to be the best girl in the house, and yet, along with Sarah, who is also being punished alongside her, she has let important clients down, by …

Watch Mistress Sarah Gregory initiate a new sub, beautiful model, Macy Nikole. She has been a fan of Sarah’s so when they got together at a Fetish event, Macy crushed …

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 …

Sarah and Luci are on a first date. Sarah is hot for Luci and cannot wait for them to get back to her place. It is no secret that they …

Cara’s confession of infidelity sets off a chain reaction of discipline and desire in this intense lesbian encounter. Sarah, determined to reclaim her trust, unleashes a punishment fit for the …

Meet Sarah, a rebellious little slut who’s been caught red-handed standing on street corners, flaunting her provocative attire. Officer Bernadette arrives at Sarah’s doorstep, determined to teach her a lesson. …