Jessie (Whitcomb) was already in big trouble long before she was ordered to bend over the kitchen counter. The girl was placed on a weekly punishment program for defiance a …

Jessie Whitcomb was already sore as she’d been spanked earlier in the day for a couple of different videos. However, before that afternoon even came, she’d confessed the need for …

Shy and Jessie have found themselves getting paddled a lot lately! Both girls were repeatedly in trouble during senior year so they were sent to summer school, that would allow …

It seems like Jessie Whitcomb has been getting spanked at least once, sometimes even twice a week for the last few months. She was becoming a careless girl that that …

Shy Sky had been sneaking around the back of her step-dad and began dating Jessie Whitcomb. She knew darn well that she’d been forbidden from seeing Jessie, but Shy didn’t …

Jessie Whitcomb was enjoying the end of summer and feeling very good about life in general. Over the past year a lot had changed for the girl and she was …

Jessie Whitcomb made her spanking movie debut in “Obsession”, and here she is again getting spanked! “Spankings For an Inappropriate Girl” let’s us in on the type of girl that …

Jessie had to know that she was going to be facing some serious consequences. She’d been fighting with a girl at school and pushed her down hard to the ground! …

Jessie Whitcomb had required appointments to see her advisor after school twice a week. Once there she would sit on the couch and not say a word. She felt above …

Recently, in “A Required Spanking”, Jessie Whitcomb was spanked for getting in a fight at school and not being responsible for her part in the altercation. In fact, Jessie hadn’t …