Tag Archives: Shy Sky

“Soaped, Strapped, and Paddled” is the follow up to “Return to Sender” and Shy Sky gets her bottom severely punished! Previously, Shy returned home from college for a visit and …

Shy Sky had already been grounded and was given several restrictions earlier in the week. She was supposed to focus on bettering herself and catching up on homework. So, you …

“Bare Welted Bottoms: A Caning Punishment” is the third and final part to a trilogy that includes the videos “Hearing Her Suffer” and “Sharing Her Pain”. This video is loaded …

Several months ago, Samantha Storm was spanked for her last time at home before heading off to college She vowed that she’d never have her bottom punished ever again. Upon …

Samantha wasn’t far off from graduation and she thought her butt was safe from her step-dad’s belt and paddles, but as you’ll see she gets her firm cheeks lit up …

The last thing that Mr. Sky expected to hear yesterday morning was that his step-daughter (Shy Sky) had been going wild with guys at the gym, several of them in …

In “A Summer of Hard Spankings” part 1, Shy Sky was discovered at a hotel with a boy and she was in serious trouble. She had lied and hurt her …

It’s best to be on good behavior when you have a strict step-dad. Shy (Sky) knew all too well that breaking the rules around her house could lead to a …

It was just another day for Caroline Adams (Shy Sky), she was getting her things together to take off for work, ready for another day of making people miserable. As …

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 …