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Upskirt galleries

Upskirt galleries featuring the all natural nude models from abbywinters.com. There are 160 upskirt galleries available at Abby Winters Girls.

Hairy brunette amateur pulls down her thong

16 2,979 Jun 23, 2026

Cute blonde amateur fingering her shaved pussy

16 6,312 Jun 20, 2026

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16 8,831 Jun 16, 2026

Cute amateur pulls down her panties on the couch

16 4,244 Jun 10, 2026

Cute redhead with puffy nipples stripping in the backyard

16 8,063 Jun 7, 2026

Freckled redhead spreads her wet hairy pussy outdoors

16 10,112 May 31, 2026

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

16 11,808 May 30, 2026

Blonde amateur with firm tits stripping outdoors

16 7,954 May 28, 2026

Brunette amateur with firm tits lifts up her skirt outdoors

16 7,977 May 25, 2026

Short-haired amateur lifts up her dress in a field

16 11,930 May 23, 2026

Cute redhead lifts up her skirt on the balcony

16 9,158 May 22, 2026

Nerdy brunette amateur spreads her ass and pussy in bed

16 8,181 May 13, 2026

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16 8,223 May 10, 2026

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16 8,845 May 4, 2026

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Freckled brunette spreads her hairy pussy outdoors

16 9,333 Apr 16, 2026

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16 14,709 Apr 13, 2026

Cute amateur spreads her creamy hairy pussy in a field

16 17,492 Apr 10, 2026

Freckled blonde girl spreads her wet pussy in the backyard

14 12,527 Mar 31, 2026

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16 13,952 Mar 30, 2026

Cute nerdy amateur exposes her hairy bush in a field

16 10,770 Mar 27, 2026

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16 12,197 Mar 23, 2026

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16 10,818 Mar 22, 2026

Upskirt galleries

Freckled brunette amateur exposes her creamy pussy outdoors

16 9,886 Mar 19, 2026

Cute amateur fingering her hairy pussy on a chair

16 14,536 Mar 5, 2026

Hairy brunette amateur stripping on a balcony

16 14,372 Mar 3, 2026

Redhead amateur plays with her huge clit on the couch

16 21,408 Mar 1, 2026

Hairy brunette amateur stripping after a rave party

16 7,681 Feb 28, 2026

Cute shaved girl lifts up her skirt on a chair

16 10,666 Feb 26, 2026

Brunette amateur toying her thick hairy bush

16 17,739 Feb 22, 2026

Muscular brunette with short hair stripping on a chair

16 13,805 Feb 8, 2026

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16 20,053 Jan 27, 2026

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16 17,572 Jan 25, 2026

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16 13,682 Jan 24, 2026

Blonde amateur exposes her big firm tits

16 10,093 Jan 19, 2026

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16 15,817 Jan 15, 2026

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16 21,314 Jan 12, 2026

Australian amateur stripping in the rain

16 13,588 Jan 9, 2026

Cute shaved brunette exposes her wet pussy in bed

16 13,635 Jan 5, 2026

Freckled brunette lifts up her skirt in bed

16 16,732 Jan 2, 2026

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

16 15,382 Dec 27, 2025

Freckled redhead amateur lifts up her skirt in bed

7 11,488 Dec 24, 2025

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16 13,060 Dec 19, 2025

Chubby brunette lifts up her dress and exposes her hairy pussy

16 11,233 Nov 24, 2025

Petite redhead teen with a big hairy bush

8 12,708 Nov 20, 2025

Freckled redhead with big natural tits masturbating

17 14,987 Oct 10, 2025

Chubby 18 y/o blonde showing off her big tits

17 10,480 Oct 6, 2025

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

Upskirt galleries

Brunette amateurs with tan lines rubbing her big aroused clit

17 21,707 Oct 5, 2025

Flat-chested blonde amateur in panties in a forest

12 20,105 Sep 30, 2025

Cute redhead amateur exposes her thick ginger bush

16 29,530 Sep 14, 2025

Lesbian amateurs having sex in bed

16 14,253 Sep 5, 2025

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16 14,695 SamaraAug 9, 2025

Busty freckled blonde with huge pancake areolas stripping

17 15,952 Aug 4, 2025

Cute blonde amateur pulls down her panties on the terrace

12 14,372 Jul 28, 2025

Flat-chested 18+ teen fingering her dark asshole

8 12,911 Jul 2, 2025

Sexy brunette amateur with a perfect ass

16 19,709 Jun 11, 2025

Chubby redhead amateur exposes her thick hairy bush

21 23,456 Apr 4, 2025

Brunette amateur plays with her hairy pussy

16 24,605 Jan 8, 2025

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12 25,711 Jan 3, 2025

Top 15 must-see upskirt pics from Abby Winters

21 24,960 Oct 7, 2024

Chubby brunette amateur shows off her big saggy tits

20 25,053 Sep 6, 2024

Cute nerdy amateur exposes her hairy pussy and asshole

20 28,008 Jul 21, 2024

Blonde amateur lifts up her skirt and reveals her hairy pussy

20 26,497 Jul 11, 2024

Nerdy brunette lifts up her skirt and spreads her hairy pussy

16 69,284 Sep 25, 2023

Cute freckled redhead lifts up her skirt

16 42,375 May 22, 2023

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

16 45,549 May 9, 2023

Shaved brunette amateur lifts up her dress in the library

16 29,176 Apr 8, 2023

Gorgeous busty girl toying her shaved pussy in bed

16 46,891 Apr 6, 2023

Freckled blonde amateur toying her hairy pussy

16 35,556 Mar 19, 2023

Cute freckled blonde with firm tits lifts up her dress

16 39,846 Mar 13, 2023

Chubby blonde amateur toying her meaty pussy in bed

16 33,952 Feb 11, 2023

Upskirt galleries

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

17 28,961 Feb 1, 2023

Cute blonde lifts up her dress to finger her hairy pussy

16 60,803 Jan 8, 2023

Cute shaved brunette lifts up her skirt and spreads her legs

16 50,361 Jan 4, 2023

Cute hairy blonde toying her ass and pussy

16 36,699 Jan 2, 2023

Cute brunette musician lifts up her skirt and strips naked

16 36,642 Olivia LustDec 28, 2022

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

16 30,141 Dec 20, 2022

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

16 42,238 Dec 6, 2022

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

16 41,588 Myra GlasfordDec 4, 2022

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12 48,530 Dec 3, 2022

Roselina in Tiny Breasts by Abby Winters

16 30,392 Nov 12, 2022

Pearl in Naked In The Forest by Abby Winters

16 44,997 Hot PearlOct 22, 2022

Wendy T in Outdoors by Abby Winters

16 32,576 Oct 9, 2022

Upskirt shots of an hairy amateur

15 38,405 Sep 4, 2022

Oksana B in Lacy Lingerie by Abby Winters

16 26,208 Sep 3, 2022

Curly-haired brunette amateur lifts up her skirt

16 36,446 Aug 16, 2022

Hairy brunette amateur nude in the pool

12 24,419 Jun 25, 2022

Cute brunette amateur stripping on a chair

15 37,498 May 1, 2022

Pale cutie with black hair fingering her hairy bush

15 48,949 Apr 22, 2022

Chubby brunette amateur toying her shaved pussy

12 36,413 Mar 27, 2022

Busty blonde lifts up her skirt to reveal her bush

14 45,517 Feb 22, 2022

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

16 41,378 Feb 10, 2022

Cute nerdy girl masturbates with her pearl thong

16 34,804 Jan 5, 2022

Curvy brunette amateur toying with a toothbrush

16 29,075 Jan 3, 2022

Busty redhead amateur stripping in a forest

16 41,487 Oct 23, 2021

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