Tag Archives: Cherry Winters

Sassy Cherry Winters is bored, so she sets up a bunch of pranks to goad Tubaman into spanking her. First, a face full of water from a sabotaged sink sprayer …

Alice is still coming down off a high from a special caning film she recently made and wanted to hang out with Case Cherry, her beautiful submissive. Case wants to …

Spoiled model Cherry Winters shows up for a shoot completely unprepared and her bottom pays the price. First, she keeps messing up her lines, so every time she messes up, …

Elle has only been at her new school for about a week and has already been accepted into the prestigious cheerleading team. However, she has certainly made herself known to …

Cherry Winters has no idea what awaits her when Alana Noex invites her over after a successful cheer practice. Fiery and fiercely protective, Alana refuses to let anyone threaten her …

Please welcome the gorgeous flame-haired Elle McKenzie, making her unforgettable debut with us at AAA in our renowned Positions series. Equally exciting, stunning Cherry Winters takes on her very first …

Cherry Winters and Cara Day have just finished their latest practice on a special school team trip, and the competition is fierce, especially with the coveted cheer captaincy up for …

Cherry’s patience has finally run out with her deadbeat roommate. For three months, Alana hasn’t paid a penny of rent. Calm but firm, Cherry makes it clear she isn’t running …

Lexi and Cherry are at a Spanking Party and have found some free time to spend alone. The hedonistic atmosphere of the gathering has fueled gorgeous Lexi’s desire to play …

This release is a thrilling “double debut” for Intimate Spanking. Please welcome the stunning flame-haired Elle McKenzie in a beautifully submissive role, paired with the irresistible Cherry Winters taking charge …