In an average month, Jessie and Shy might earn one spanking, maybe two at the most. This past week, they already had to bend over for two and now they’re …

Jessie Whitcomb is a beautiful young woman who happened to fall in with the wrong crowd. She wanted to live life in the fast lane while making a lot of …

Jessie’s step-dad couldn’t have been more proud, she’d been doing much better in her dance class and even getting along better with all of the other girls. It had been …

Principal Studaker wasn’t a big fan of Jessie Whitcomb. She was sassy, often disrespectful, and rarely followed the dress code. The girl was regularly sent to his office, but there …

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 …