Tag Archives: Shy Sky

Shy Sky (as seen in “Caned in a Foreign Land” and “The Worst Day of her Life”) hasn’t been spanked in years. She’s also always kept up with her grades …

One of the hottest things about life is a girl who absolutely lives for getting a spanking, one who expects punishment when it’s deserved. She’ll think about having her bottom …

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 …

Recently, Shy Sky was absent minded and neglectful of her duties on the farm, so she received a “blistering in the barn”. Her step-dad made it very clear that if …

Living out in the country has its advantages,…lots of fresh air, beautiful scenery, and of course a wholesome lifestyle. Shy Sky loved almost everything about it, especially when she could …

Repeated trouble at home and at school has brought about a serious evening of punishment for Victoria Cryer, Samantha Storm, Shy Sky in their first ever spanking together! Watch as …

This video is partially based on a true story and involves a family immersed in a tale of lies, deceit, and bare bottom punishment! It all started when a very …

Jessie Whitcomb and Shy Sky were so excited for their first year of college! They’d heard a lot about sorority living and hoped that they’d have even more fun than …

Shy Sky had been warned, she was always supposed to take the long way home after school. The longer route was thought to be much safer than cutting through the …

In “Taken to the Woodshed” Shy Sky was given a very painful spanking for disobeying her step-dad and walking home from school through the woods. “Off the Beaten Path” takes …