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PinupFiles brings you the biggest and best exclusive collection of big boob content featuring the most beautiful busty pinup girls anywhere online for your viewing pleasure. Come meet them all inside! Updated multiple times a week!

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Georgie Darby - Navy Lace - Lap Dance 1
12:08 | Sep 22, 2023
Georgie Darby
Jenny Oops - PinupFiles -25th Anniversary - Set 2
Jenny Oops - PinupFiles -25th Anniversary - Set 2
20 Photos, 00:0 | Sep 21, 2023
Jenny Oops
Subrina Lucia - Bella Yellow 2
29:41 | Sep 19, 2023
Subrina Lucia
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Jenny Oops - PinupFiles - 25th Anniversary 2
09:24 | Sep 15, 2023
Jenny Oops
Tori Hendricks - 25th Anniversary - Set 3
Tori Hendricks - 25th Anniversary - Set 3
18 Photos, 00:0 | Sep 14, 2023
Tori Hendricks
Brandy Robbins - Sunsual Shower 2
23:32 | Sep 12, 2023
Brandy Robbins
Stacey Poole - New Blue Pool 1
15:40 | Sep 8, 2023
Stacey Poole
Jenny Oops - PinupFiles - 25th Anniversary - Set 1
Jenny Oops - PinupFiles - 25th Anniversary - Set 1
20 Photos, 00:0 | Sep 6, 2023
Jenny Oops
Fiona Siciliano - Pink Sauna 2
18:13 | Sep 5, 2023
Fiona Sciciliano
Jenny Oops - PinupFiles - 25th Anniversary 1
Jenny Oops - PinupFiles - 25th Anniversary 1
11:06 | Sep 1, 2023
Jenny Oops
September Carrino - Pinup Cami - Remastered - Photoshots - Set 1
September Carrino - Pinup Cami - Remastered - Photoshots - Set 1
22 Photos, 00:0 | Aug 30, 2023
September Carrino
Demmy Blaze - White Pearl 2
24:09 | Aug 29, 2023
Demmi Blaze
Maria Body - Big Plums 2
25:58 | Aug 26, 2023
Maria Body
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Makayla Melons - Pinupfiles 25th Anniversary - Set 2
Makayla Melons - Pinupfiles 25th Anniversary - Set 2
20 Photos, 00:0 | Aug 24, 2023
Makayla Melons
Amber Campisi - PinupFiles - T-Shirt 2
10:23 | Aug 22, 2023
Amber Campisi
Makayla Melons - PinupFiles 25th Anniversary 2
13:20 | Aug 19, 2023
Makayla Melons
Lana Kendrick - PinupFiles 25th Anniversary - Set 2
Lana Kendrick - PinupFiles 25th Anniversary - Set 2
20 Photos, 00:0 | Aug 16, 2023
Lana Kendrick
Kitty Cute - Savoy Blue 2
16:48 | Aug 15, 2023
Kitty Cute
G.G. Doll - Thatch Parasol 3 - Glorious
12:56 | Aug 12, 2023
G.G. Doll
Makayla Melons - PinupFiles 25th Anniversary - Set 1
Makayla Melons - PinupFiles 25th Anniversary - Set 1
20 Photos, 00:0 | Aug 9, 2023
Makayla Melons
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Kira Liv - Floral Gold 4
29:30 | Aug 8, 2023
Kira Liv
Makayla Melons - PinupFiles 25th Anniversary 1
09:47 | Aug 5, 2023
Makayla Melons
Jana Defi - Vol. 28 - Set 2
Jana Defi - Vol. 28 - Set 2
25 Photos, 00:0 | Aug 2, 2023
Jana Defi
Jenny Oops - Office Girl 3 - Lap Dance 1
18:54 | Jul 31, 2023
Jenny Oops

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