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Upskirt galleries

Upskirt galleries featuring the all natural nude models from abbywinters.com. There are 156 upskirt galleries available at Abby Winters Girls.

Cute redhead with puffy nipples stripping in the backyard

16 5,855 Jun 7, 2026

Freckled redhead spreads her wet hairy pussy outdoors

16 8,377 May 31, 2026

Redhead amateur exposes her meaty pussy and big clit in a park

16 8,444 May 30, 2026

Blonde amateur with firm tits stripping outdoors

16 6,924 May 28, 2026

Brunette amateur with firm tits lifts up her skirt outdoors

16 7,176 May 25, 2026

Short-haired amateur lifts up her dress in a field

16 10,572 May 23, 2026

Cute redhead lifts up her skirt on the balcony

16 8,344 May 22, 2026

Nerdy brunette amateur spreads her ass and pussy in bed

16 7,595 May 13, 2026

Blonde amateur shows off her flawless shaved pussy

16 7,680 May 10, 2026

Short-haired amateur shows off her hairy blond bush

16 8,107 May 4, 2026

Cute brunette with puffy nipples stripping on the couch

16 10,798 Apr 20, 2026

Busty brunette amateur spreads her hairy pussy on a balcony

16 10,664 Apr 19, 2026

Freckled brunette spreads her hairy pussy outdoors

16 8,867 Apr 16, 2026

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16 13,924 Apr 13, 2026

Cute amateur spreads her creamy hairy pussy in a field

16 16,617 Apr 10, 2026

Freckled blonde girl spreads her wet pussy in the backyard

14 12,061 Mar 31, 2026

Cute blonde with firm tits naked by a window

16 13,504 Mar 30, 2026

Cute nerdy amateur exposes her hairy bush in a field

16 10,298 Mar 27, 2026

Busty brunette amateur exposes her hairy bush in public

16 11,736 Mar 23, 2026

Hairy brunette stripping and pissing outdoors

16 10,436 Mar 22, 2026

Freckled brunette amateur exposes her creamy pussy outdoors

16 9,598 Mar 19, 2026

Cute amateur fingering her hairy pussy on a chair

16 14,185 Mar 5, 2026

Hairy brunette amateur stripping on a balcony

16 14,111 Mar 3, 2026

Redhead amateur plays with her huge clit on the couch

16 20,657 Mar 1, 2026

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Hairy brunette amateur stripping after a rave party

16 7,555 Feb 28, 2026

Cute shaved girl lifts up her skirt on a chair

16 10,375 Feb 26, 2026

Brunette amateur toying her thick hairy bush

16 17,185 Feb 22, 2026

Muscular brunette with short hair stripping on a chair

16 13,504 Feb 8, 2026

Cute amateur spreads her hairy ass and pussy on the couch

16 19,603 Jan 27, 2026

Upskirt pics of a cute shaved brunette stripping in a tree

16 17,290 Jan 25, 2026

Cute flexible amateur stripping in bed

16 13,441 Jan 24, 2026

Blonde amateur exposes her big firm tits

16 9,923 Jan 19, 2026

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16 15,504 Jan 15, 2026

Chubby brunette with big tits spreads her shaved pussy in bed

16 20,901 Jan 12, 2026

Australian amateur stripping in the rain

16 13,344 Jan 9, 2026

Cute shaved brunette exposes her wet pussy in bed

16 13,412 Jan 5, 2026

Freckled brunette lifts up her skirt in bed

16 16,510 Jan 2, 2026

Sporty blonde amateur shows off her huge puffy nipples in a field

16 15,168 Dec 27, 2025

Freckled redhead amateur lifts up her skirt in bed

7 11,295 Dec 24, 2025

Upskirt pics of an athletic blonde amateur with pencil eraser nipples

16 12,854 Dec 19, 2025

Chubby brunette lifts up her dress and exposes her hairy pussy

16 11,009 Nov 24, 2025

Petite redhead teen with a big hairy bush

8 12,453 Nov 20, 2025

Freckled redhead with big natural tits masturbating

17 14,747 Oct 10, 2025

Chubby 18 y/o blonde showing off her big tits

17 10,399 Oct 6, 2025

Brunette amateurs with tan lines rubbing her big aroused clit

17 21,306 Oct 5, 2025

Flat-chested blonde amateur in panties in a forest

12 19,810 Sep 30, 2025

Cute redhead amateur exposes her thick ginger bush

16 29,196 Sep 14, 2025

Lesbian amateurs having sex in bed

16 14,021 Sep 5, 2025

2,079 Nude Girls | 7,238 scenes | 9,954 videos | 998,408 images

Upskirt galleries

Chubby amateur with huge tits and nipples

16 14,473 SamaraAug 9, 2025

Busty freckled blonde with huge pancake areolas stripping

17 15,752 Aug 4, 2025

Cute blonde amateur pulls down her panties on the terrace

12 14,235 Jul 28, 2025

Flat-chested 18+ teen fingering her dark asshole

8 12,772 Jul 2, 2025

Sexy brunette amateur with a perfect ass

16 19,500 Jun 11, 2025

Chubby redhead amateur exposes her thick hairy bush

21 23,333 Apr 4, 2025

Brunette amateur plays with her hairy pussy

16 24,524 Jan 8, 2025

Hairy lesbian fingering her lover's asshole

12 25,526 Jan 3, 2025

Top 15 must-see upskirt pics from Abby Winters

21 24,842 Oct 7, 2024

Chubby brunette amateur shows off her big saggy tits

20 24,949 Sep 6, 2024

Cute nerdy amateur exposes her hairy pussy and asshole

20 27,920 Jul 21, 2024

Blonde amateur lifts up her skirt and reveals her hairy pussy

20 26,415 Jul 11, 2024

Nerdy brunette lifts up her skirt and spreads her hairy pussy

16 69,127 Sep 25, 2023

Cute freckled redhead lifts up her skirt

16 42,320 May 22, 2023

Freckled brunette amateur lifts up her skirt and reveals her hairy bush

16 45,430 May 9, 2023

Shaved brunette amateur lifts up her dress in the library

16 29,122 Apr 8, 2023

Gorgeous busty girl toying her shaved pussy in bed

16 46,767 Apr 6, 2023

Freckled blonde amateur toying her hairy pussy

16 35,477 Mar 19, 2023

Cute freckled blonde with firm tits lifts up her dress

16 39,762 Mar 13, 2023

Chubby blonde amateur toying her meaty pussy in bed

16 33,848 Feb 11, 2023

Blonde with fair skin lifts up her skirt to fuck her shaved pussy

17 28,873 Feb 1, 2023

Cute blonde lifts up her dress to finger her hairy pussy

16 60,596 Jan 8, 2023

Cute shaved brunette lifts up her skirt and spreads her legs

16 50,219 Jan 4, 2023

Cute hairy blonde toying her ass and pussy

16 36,559 Jan 2, 2023

Upskirt galleries

Cute brunette musician lifts up her skirt and strips naked

16 36,520 Olivia LustDec 28, 2022

Cute brunette pulls down her panties and fucks her shaved pussy with a toy

16 30,055 Dec 20, 2022

Cute blonde amateur Alice lifts up her skirt and spreads her ass and pussy

16 42,172 Dec 6, 2022

Insanely cute freckled redhead lifts up her skirt and exposes her tight bald pussy

16 41,479 Myra GlasfordDec 4, 2022

Arie in Meaty Lips by Abby Winters

12 48,338 Dec 3, 2022

Roselina in Tiny Breasts by Abby Winters

16 30,298 Nov 12, 2022

Pearl in Naked In The Forest by Abby Winters

16 44,817 Hot PearlOct 22, 2022

Wendy T in Outdoors by Abby Winters

16 32,504 Oct 9, 2022

Upskirt shots of an hairy amateur

15 38,309 Sep 4, 2022

Oksana B in Lacy Lingerie by Abby Winters

16 26,160 Sep 3, 2022

Curly-haired brunette amateur lifts up her skirt

16 36,392 Aug 16, 2022

Hairy brunette amateur nude in the pool

12 24,389 Jun 25, 2022

Cute brunette amateur stripping on a chair

15 37,438 May 1, 2022

Pale cutie with black hair fingering her hairy bush

15 48,831 Apr 22, 2022

Chubby brunette amateur toying her shaved pussy

12 36,326 Mar 27, 2022

Busty blonde lifts up her skirt to reveal her bush

14 45,373 Feb 22, 2022

Good looking brunette Eve S strips off her blue dress and flashes her tits

16 41,293 Feb 10, 2022

Cute nerdy girl masturbates with her pearl thong

16 34,722 Jan 5, 2022

Curvy brunette amateur toying with a toothbrush

16 29,029 Jan 3, 2022

Busty redhead amateur stripping in a forest

16 41,359 Oct 23, 2021

Cute brunette amateur shows off her creamy pussy

16 31,488 Sep 28, 2021

Cute amateur with blue eyes fingering her hairy pussy

12 62,537 Sep 22, 2021

Nerdy brunette fingering her hairy pussy

14 43,417 Sep 6, 2021

Lovely blonde stripping in her backyard

16 47,355 Aug 17, 2021

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