Tag Archives: Older Woman / Younger Man

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, …

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 …

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 …

Governess Worthington takes her diapered Step-Mommie’s boys on a road trip to the in-laws house. While out, they stop by a fast food restaurant. The boys begin to get unruly …

Governess Worthington wakes her bedwetting Mommie’s boy to discover a big wet spot and that once again he has wet the bed. She chastises him, does an OTK spanking with …

Charlie has changed a lot, from the sweet boy his Aunty used to sit on her knee. He has turned into a very bad boy, and now she has come …

Charlie and his strict Aunty continue their disciplinary relationship, during her visit to the States. This time she introduces him to the strap. She gives him several strokes across his …