Cherry Winters Fetish Videos & Clips
Cherry Winters Fetish Videos & Clips
Cherry Winters XXX Latest Videos
A little too Flirty- Kiki spanks Cherry for flirting with her step-Dad - Butt Angle
10/3/26 1:50 AM•10 min•431 MB•mp4•1080p
A little too Flirty- Kiki spanks Cherry for flirting with her step-Dad - Butt Angle
10/3/26 1:50 AM•10 min•431 MB•mp4•1080pDescriptionKiki sits down with Cherry to confront her about her flirty behavior. Kiki is fed up and demands to settle the score with Cherry over her lap. Continuing to scold while she spanks hard and fast, Kiki makes sure the message gets delivered. Cherry is well aware of the interest coming from Kiki’s step dad, dressing extra slutty. Her skirts get shorter, as she dresses up for attention, finding herself across Kiki’s knee with her skirt flipped up for a firm hand spanking. KIKI CALI, CHERRY WINTERS, BARE BOTTOM SPANKING, PADDLING, DAISY DUKES, DOMESTIC DISCIPLINE, TABOO, SPANKING CRUSH, TOPLESS
Cherry's Punishment Chart, Part 2, Mf, MOV
10/1/26 9:00 PM•8 min•579 MB•mov•1080p
Cherry's Punishment Chart, Part 2, Mf, MOV
10/1/26 9:00 PM•8 min•579 MB•mov•1080pPrice$8.99 USDCategorySpankingRelated CategoriesClassic Spanking,Jeans Fetish,Paddling,Spanking M/FPerformersPaul Rogers, Cherry WintersDescriptionSassy Cherry Winters is already sporting a tender behind from a sound spanking, and now she is in for more.
She tricked her three friends into playing ping pong for money, and now she must bend over for three separate paddlings with her own ping pong paddle.
After each spanking, she must call her victim and apologize.
Cherry's Punishment Chart, Part 2, Mf, WMV
10/1/26 5:00 PM•8 min•240 MB•wmv•1080p
Cherry's Punishment Chart, Part 2, Mf, WMV
10/1/26 5:00 PM•8 min•240 MB•wmv•1080pPrice$8.99 USDCategorySpankingRelated CategoriesClassic Spanking,Jeans Fetish,Paddling,Spanking M/FPerformersPaul Rogers, Cherry WintersDescriptionSassy Cherry Winters is already sporting a tender behind from a sound spanking, and now she is in for more.
She tricked her three friends into playing ping pong for money, and now she must bend over for three separate paddlings with her own ping pong paddle.
After each spanking, she must call her victim and apologize.
Cherry's Punishment Chart, Part 2, Mf, MP4
10/1/26 12:00 PM•8 min•95 MB•mp4•480p
Cherry's Punishment Chart, Part 2, Mf, MP4
10/1/26 12:00 PM•8 min•95 MB•mp4•480pPrice$8.99 USDCategorySpankingRelated CategoriesClassic Spanking,Jeans Fetish,Paddling,Spanking M/FPerformersPaul Rogers, Cherry WintersDescriptionSassy Cherry Winters is already sporting a tender behind from a sound spanking, and now she is in for more.
She tricked her three friends into playing ping pong for money, and now she must bend over for three separate paddlings with her own ping pong paddle.
After each spanking, she must call her victim and apologize.
Jeans-Lovers Special #56, Mffffff, MP4
9/30/26 1:58 PM•20 min•1080 MB•mp4•1080p
Jeans-Lovers Special #56, Mffffff, MP4
9/30/26 1:58 PM•20 min•1080 MB•mp4•1080pPrice$15.99 USDCategorySpankingRelated CategoriesClassic Spanking,Jeans Fetish,Otk Spanking,Paddling,Spanking M/FKeywordsSore Bottom,Bare Bottom,Red Bottom,Naughty Girls,Bend Over,Tight Pants,Punisment,Discipline,Asses,ButtsPerformersPaul Rogers, Rachel Adams, Cherry Winters, Lexi Holland, Cara Day, Iris Steele, Alana NoexDescriptionNaughty girls take hard spankings on their tight jeans.
- Beautiful Cara Day and leggy Iris Steele bend over for a paddling from the Principal.
- As does tender Alana Noex.
- Same for sore Rachel Adams, THREE TIMES OVER.
- Then, since Cara is not yet sore enough, she gets a sound OTK spanking to boot.
- As does exotic Cherry Winters, plus a paddling, plus a SECOND spanking.
Jeans-Lovers Special #56, Mffffff, MOV
9/30/26 1:57 PM•20 min•1404 MB•mov•1080p
Jeans-Lovers Special #56, Mffffff, MOV
9/30/26 1:57 PM•20 min•1404 MB•mov•1080pPrice$15.99 USDCategorySpankingRelated CategoriesClassic Spanking,Jeans Fetish,Otk Spanking,Paddling,Spanking M/FPerformersPaul Rogers, Rachel Adams, Cherry Winters, Lexi Holland, Cara Day, Iris Steele, Alana NoexDescriptionNaughty girls take hard spankings on their tight jeans.
- Beautiful Cara Day and leggy Iris Steele bend over for a paddling from the Principal.
- As does tender Alana Noex.
- Same for sore Rachel Adams, THREE TIMES OVER.
- Then, since Cara is not yet sore enough, she gets a sound OTK spanking to boot.
- As does exotic Cherry Winters, plus a paddling, plus a SECOND spanking.
Jeans-Lovers Special #56, Mffffff, WMV
9/30/26 1:56 PM•20 min•1176 MB•wmv•1080p
Jeans-Lovers Special #56, Mffffff, WMV
9/30/26 1:56 PM•20 min•1176 MB•wmv•1080pPrice$15.99 USDCategorySpankingRelated CategoriesClassic Spanking,Jeans Fetish,Otk Spanking,Paddling,Spanking M/FKeywordsSore Bottom,Bare Bottom,Red Bottom,Naughty Girls,Bend Over,Tight Pants,Punishment,Discipline,Asses,ButtsPerformersPaul Rogers, Rachel Adams, Cherry Winters, Lexi Holland, Cara Day, Iris Steele, Alana NoexDescriptionNaughty girls take hard spankings on their tight jeans.
- Beautiful Cara Day and leggy Iris Steele bend over for a paddling from the Principal.
- As does tender Alana Noex.
- Same for sore Rachel Adams, THREE TIMES OVER.
- Then, since Cara is not yet sore enough, she gets a sound OTK spanking to boot.
- As does exotic Cherry Winters, plus a paddling, plus a SECOND spanking.
Cornercopia #63, MMffffff, MOV
9/28/26 9:00 PM•17 min•1197 MB•mov•1080p
Cornercopia #63, MMffffff, MOV
9/28/26 9:00 PM•17 min•1197 MB•mov•1080pPrice$14.99 USDCategorySpankingRelated CategoriesJeans Fetish,Otk Spanking,Paddling,Spandex,Spanking M/FKeywordsSore Bottoms,Red Bottom,Bare Bottom,Naughty Girl,Punishment,Discipline,Corner Time,Time Out,Bend Over,Tight Pants,Asses,ButtsPerformersPaul Rogers, Kiki Cali, Cherry Winters, Lexi Holland, Cara Day, Iris Steele, Jeremy Salter, Alana NoexDescriptionSix naughty girls are soundly spanked then sent to embarrassing corner time.
- Beautiful Alana Noex gets the seat of her pantyhose heated, then her bare bottom blistered.
- Cara Day, Iris Steele, and Lexi Holland get paddled hard on their thin spandex pants.
- Cherry Winters takes a bare-bottom bottom blistering.
- Cara gets ANOTHER hard paddling on her skintight jeans.
- Kiki Cali gets a sound OTK spanking.
Each followed by humiliating corner time.
Cherry's Punishment Chart, Part 1, Mf, MOV
9/28/26 9:00 PM•8 min•555 MB•mov•1080p
Cherry's Punishment Chart, Part 1, Mf, MOV
9/28/26 9:00 PM•8 min•555 MB•mov•1080pPrice$8.99 USDCategorySpankingRelated CategoriesClassic Spanking,Jeans Fetish,Otk Spanking,Spanking M/FPerformersPaul Rogers, Cherry WintersDescriptionSassy Cherry Winters has been misbehaving while Tubaman was out of town, but now he is home, and it is time to pay the piper.
First, a hard spanking on her skintight jeans, so severe she can't sit down afterwards.
Cornercopia #63, MMffffff, WMV
9/28/26 5:00 PM•17 min•755 MB•wmv•1080p
Cornercopia #63, MMffffff, WMV
9/28/26 5:00 PM•17 min•755 MB•wmv•1080pPrice$14.99 USDCategorySpankingRelated CategoriesJeans Fetish,Otk Spanking,Paddling,Spandex,Spanking M/FKeywordsSore Bottoms,Reed Bottom,Bare Bottom,Naughty Girls,Bend Over,Punishment,Discipline,Tight Pants,Corner Time,Time Out,Asses,ButtsPerformersPaul Rogers, Kiki Cali, Cherry Winters, Lexi Holland, Cara Day, Iris Steele, Jeremy Salter, Alana NoexDescriptionSix naughty girls are soundly spanked then sent to embarrassing corner time.
- Beautiful Alana Noex gets the seat of her pantyhose heated, then her bare bottom blistered.
- Cara Day, Iris Steele, and Lexi Holland get paddled hard on their thin spandex pants.
- Cherry Winters takes a bare-bottom bottom blistering.
- Cara gets ANOTHER hard paddling on her skintight jeans.
- Kiki Cali gets a sound OTK spanking.
Each followed by humiliating corner time.
Cherry's Punishment Chart, Part 1, Mf, WMV
9/28/26 5:00 PM•8 min•251 MB•wmv•1080p
Cherry's Punishment Chart, Part 1, Mf, WMV
9/28/26 5:00 PM•8 min•251 MB•wmv•1080pPrice$8.99 USDCategorySpankingRelated CategoriesClassic Spanking,Jeans Fetish,Otk Spanking,Spanking M/FPerformersPaul Rogers, Cherry WintersDescriptionSassy Cherry Winters has been misbehaving while Tubaman was out of town, but now he is home, and it is time to pay the piper.
First, a hard spanking on her skintight jeans, so severe she can't sit down afterwards.
Cherry's Punishment Chart, Part 1, Mf, MP4
9/28/26 12:00 PM•8 min•91 MB•mp4•480p
Cherry's Punishment Chart, Part 1, Mf, MP4
9/28/26 12:00 PM•8 min•91 MB•mp4•480pPrice$8.99 USDCategorySpankingRelated CategoriesClassic Spanking,Jeans Fetish,Otk Spanking,Spanking M/FPerformersPaul Rogers, Cherry WintersDescriptionSassy Cherry Winters has been misbehaving while Tubaman was out of town, but now he is home, and it is time to pay the piper.
First, a hard spanking on her skintight jeans, so severe she can't sit down afterwards.
