Tag Archives: Older Woman / Younger Man

This is from the perspective of a fed up, patriotic stepmom of a college age Stepson that had stolen items from her to use them to commit Anarchist type rioting. …

Today is your big day! You have concealed your spanking & cell phone addiction enough to get a first date with Ms. Worthington’s step-daughter, Allison. Once Allison gets in your …

You knew what would happen if you were caught stealing your Sister’s car and took it out for a joyride again. You were warned… but took your chances and snuck …

My stepson and his friend Brandon were having over. I had to leave to run an errand, but before I left, I told them my full behavioral expectations. I return …

Tailgate Party Diapering! Diapered on game day by Mommy Katherine as Sister Shelley & her friend Claire watches on and helps! In this EPIC video, it’s game day & you’re …

Caught on webcam! Babysitter Alice & Katherine spanks & diapers you while Alice’s friends watch on a live video stream! – HD 1080 Mom Katherine is running errands and at …

My friend and her husband Peaches were at a weekend getaway at a hotel when she saw not only was he acting out, but he didn’t wear his chastity device, …

You know I have no tolerance for bad personal and bathroom hygiene, but today your shy little sister (Rachel Adams) brought to my attention that you (my son) made a …

Sexy social worker and enforcer Miss Katherine is a no nonsense woman from the Department of disciplinary services who thrives in her line of work and has zero tolerance for …

Miss Katherine is called to her step-son & step-daughter in law’s house. Her step-daughter in law is very upset because her step-son acts out, doing whatever he wants in the …