Tag Archives: Older Woman / Younger Man

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 …

Governess Worthington’s son is athletic & loves to run track. In order for him to stay focused & be as successful as possible, Governess gives him a milking on the …

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, …

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 …

It’s your birthday and Mommy arranged a birthday party for you at Hooters! It has been a day full of surprises (as in part 1) you wet your big boy …

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 …

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 …

Can Mommy not have a telephone conversation without you getting into trouble? After you see your stepsister come in from soccer and tell me she’s taking a shower, you take …

I live with my absolutely bonkers Aunt. She got it in her head that she can turn me into a girl, because she likes girls more than boys. I have …