Tag Archives: Regression Session

Essie has been left sitting bare bottomed on the punishment pad to reflect on her recent bad behaviour. Her poor welted bottom is in agony as the sharp spikes prick …

Essie is a grown woman who acts like a silly spoilt brat. Step Mommy Sarah knows exactly how to treat ladies who do not know how to behave and is …

It’s been a while since Essie has been to visit her Step-Sister in Law Step Mommy Sarah and standards have been slipping. Sarah receives a call informing her that Essie …

It seems that Willow is beginning to get used to life under the care and control of her her Step Mommy Sarah. She hasn’t been in trouble for some time …

A very sorry, sore and contrite Essie has been sent to bed by her Step-Sister in Law Sarah. She knows she is going to be punished some more and is …

You are never to old to get your bottom spanked by Step Mommy Sarah. Jane found this out recently and has been trying to follow the rules laid out in …

This film starts with young Willow in the corner of the office. Her knickers are at her knees and her hands are on her head. Her Boss Sarah Stern has …

Poor Essie is in so much trouble. Not only has she fallen foul of her Step-Sister in Law Sarah and been made to dress like a maid and do household …

Essie has been told that as she has been behaving like a spoilt then she should be dressed as one. We see her in the bedroom getting changed and putting …

It’s been a few weeks since Essie has seen her Step-Sister in Law Sarah Stern. They did not part on the greatest terms as Essie and Alora had been at …