Winter thinks she can escape her chores and hit the town in a ridiculously slutty dress, but her mom, Samantha, has other plans. Catching her bratty daughter trying to sneak …

Winter is summoned to Coach Gregory’s home after her latest bout of nonsense. This collegiate freshman is on the verge of losing her scholarship if she doesn’t shape up, respect …

Please welcome back Winter Leigh in this spirited tale of a mischievous porch pirate who has been tormenting Madame Samantha B for far too long. When Samantha discovers the culprit …

Our spanking flight attendant series is back and Winter Ryleigh looks stunning dressed in the AAA Airlines uniform. She has been summoned to the local offices where HR manager, Miss …

We are excited to welcome Winter Ryleigh to our website receiving her very first caning! Winter has been a very naughty girl who has been sent to Headmistress Matthews to …

Winter’s new stepmom (Miss Matthews) has been given permission to deal with her whenever and however she needs to… using the “old-fashioned” methods of correction. This means that a rude …

Please welcome our fabulous newcomer to our network of sites, Winter Ryleigh, in her first-ever spanking shoot alongside Clara Matthews. This is a most memorable debut appearance and we decided …