ACTRESS

Cherry Winters Spanking videos

16 videos

This page collects 15 videos from Cherry Winters in 2026. The performer appears in scenes from Aaaspanking, Cheerleaderspankings, and Mommaspankings, with a strong emphasis on F/F spanking. Over-the-knee discipline is the most frequent theme, often featuring scolding and classic implements like the hairbrush. Several scenes are set within a cheerleading context, incorporating the classic spanking dynamic.

Cherrys Day Of Pranks Full Video — Spanking 101

Full HD 12 27:09

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Cherrys Day Of Pranks Full Video — Spanking 101

Cherry Winters

12 4d

Don’t Fuck My Girlfriend — Cheerleader Spankings

EXCLUSIVE Full HD 50 10:59

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Don’t Fuck My Girlfriend — Cheerleader Spankings

Cherry Winters

50 3w

Cherry Winters Dominates in Sorority Spanking Scene

Full HD 40 11:25

Cherry Winters Dominates in Sorority Spanking Scene

Cherry Winters

40 3w

Intimate Spanking: Cherry’s Sensual Submission to Lexi

Full HD 30 15:36

+2

Intimate Spanking: Cherry’s Sensual Submission to Lexi

Case Cherry

30 1mo

Cherry’s Spanking Fantasy with Step-Daddy – Worst Behavior

Full HD 27 16:16

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Cherry’s Spanking Fantasy with Step-Daddy – Worst Behavior

Cherry Winters

27 2mo

Elle McKenzie’s Intimate Spanking Debut with Cherry Winters

Full HD 25 15:16

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Elle McKenzie’s Intimate Spanking Debut with Cherry Winters

Cherry Winters

25 2mo

Lexi Spanks Cheating Cherry – Aaaspanking Video

Full HD 33 15:20

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Lexi Spanks Cheating Cherry – Aaaspanking Video

Case Cherry

33 2mo

Cherry Winters Spanks Alana: No More Charity for Rent

Full HD 19 13:16

Cherry Winters Spanks Alana: No More Charity for Rent

Cherry Winters

19 2mo

Sloppy Cheerleaders Cherry Winters & Elle McKenzie Spanked

Full HD 33 13:50

+2

Sloppy Cheerleaders Cherry Winters & Elle McKenzie Spanked

Cherry Winters

33 2mo

Cherry Winters’ Red Bottom Spanking by Strict Stepmom – Mommaspankings

Full HD 30 14:28

Cherry Winters’ Red Bottom Spanking by Strict Stepmom – Mommaspankings

Cherry Winters

30 2mo

Deception and Discipline: Cherry’s Bare Bottom Brushing – Mommaspankings

Full HD 25 12:58

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Deception and Discipline: Cherry’s Bare Bottom Brushing – Mommaspankings

Case Cherry

25 2mo

Elle McKenzie & Cherry Winters: Sensual Spanking Positions

Full HD 2 videos 31 29:33

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Elle McKenzie & Cherry Winters: Sensual Spanking Positions

Cherry Winters

31 2mo

Cherry’s Spanking and Wedgie Punishment – Aaaspanking

Full HD 48 20:52

+3

Cherry’s Spanking and Wedgie Punishment – Aaaspanking

Atomic Wedgie

48 2mo

Cheer Diva Disciplined: Cara Day Spanks Cherry Winters | Cheerleaderspankings

Full HD 19 10:52

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Cheer Diva Disciplined: Cara Day Spanks Cherry Winters | Cheerleaderspankings

Bare And Exposed

19 2mo

Cheerleader Cherry Winters Spanked by Alana Noex – Flirting With Trouble

Full HD 54 11:02

Cheerleader Cherry Winters Spanked by Alana Noex – Flirting With Trouble

Cherry Winters

54 2mo

Cheer Captain Spanks New Girl for Sleeping with Girlfriend

Full HD 28 10:59

+1

Cheer Captain Spanks New Girl for Sleeping with Girlfriend

Cherry Winters

28 2mo

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