WINTER RYLEIGH’S HAIRBRUSH SPANKING 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 slutty brat can, at last, be taken over her lap for a long overdue and richly deserved spanking. Miss Matthews has…
DISCIPLINED FOR DECEPTION This is Winter Leigh’s first appearance on Cheerleader Spankings, and also her first ever rectal temperature taking on film. It’s Casual Friday and the school’s cheerleaders are allowed to wear their uniform. It’s also a Double-Math Day for cheergirl Winter and she doesn’t want to endure that in the afternoon. Winter decides…
Winter’s First Caning
We are excited to welcome Winter Ryleigh to the website receiving her very first caning ever! Winter has been a very naughty girl who has been sent to Headmistress Matthews to be dealt with. She has received 3 demerits and that means a caning. She is soundly spanked over Miss Matthew’s lap on her bare…
