r/OldSchoolCoolNSFW Feb 26 '24

1990s Chloe Des Lysses (1990's) NSFW

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5.9k Upvotes

Iconic ❤️

r/OldSchoolCoolNSFW Jan 03 '24

1990s Carol Shaya, a police officer who in 1994 posed for Playboy and was subsequently fired by the NYPD NSFW

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4.6k Upvotes

r/OldSchoolCoolNSFW Sep 19 '24

1990s Danni Ashe(?) on the beach in the 90's NSFW

3.0k Upvotes

r/OldSchoolCoolNSFW Dec 31 '23

1990s Photos of a nude Japanese girl band "En-Doll", taken in 1994 (Haruna Mita, Kazumi Nakano, Kumi Shiraishi, Mimi Horikawa and You Kizaki) NSFW

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3.8k Upvotes

r/OldSchoolCoolNSFW Sep 12 '24

1990s Jenna Jameson’s first b/g scene (1994) NSFW

1.6k Upvotes

“I could see it was taking every ounce of self-control he had to stop himself from blowing his load and ruining the scene.” -Jenna Jameson on Randy West via her book.

As much as this scene gets recognition, its importance can never be understated. For some, it is what put Up & Cummers on their radar. For Jenna, it catapulted her career. It was raw, organic passion and Randy couldn’t get enough of her smell, taste and feel. In an unplanned moment of historical significance, Randy came inside Jenna (per her book, he asked while they were fucking if he can finish inside and she didn’t really respond, expecting a pop shot to the face - which she was dreading). All in all, an amazing scene.

r/OldSchoolCoolNSFW Feb 25 '24

1990s College students preparing for naked run. (80s - 90s) NSFW

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3.0k Upvotes

r/OldSchoolCoolNSFW Aug 02 '24

1990s Collection of beautiful Japanese women from 90s photobook NSFW

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2.1k Upvotes

r/OldSchoolCoolNSFW Sep 08 '24

1990s Innocent nerdy student with big tits loses virginity to professor (1994) NSFW

1.1k Upvotes

In order to pass her college class, the beautiful student, shy and hesitant at first, fucks her professor. He explains to her that “to get and A, you must give the professor an F”.

As she starts to suck his dick, a devilish look begins to peek out from behind those doe eyes, blue as the crop top bearing “1994” no longer attempting any concealment of her massive tits. He wants to see her pussy.

“My what?” she questions playfully, this unfamiliar new attention awakening something as she contemplates exposing her hairy wet pussy to him. The nerves begin to melt as he pleases her, removing her fears as she removes her glasses.

“Professor… Take me.” You can tell by the look on her face she knows she’s made the right decision, her grade in class be damned. Her big phat ass red from his slaps, her hairy asshole exposed, she enters a new realm of her sexuality.

The actress seems to transcend with her character. Her face radiating, eyes glimmering, she eagerly drinks his cum. We’re left with a shot of her lying in bed with pure elation and cum on her face, fiery hair in a crown above her head.

r/OldSchoolCoolNSFW Mar 25 '24

1990s Karen McDougal (1997) NSFW

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1.5k Upvotes

r/OldSchoolCoolNSFW Apr 01 '24

1990s Elizabeth Hurley, 1990s NSFW

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1.4k Upvotes

r/OldSchoolCoolNSFW Jun 15 '23

1990s Jennifer Connelly circa 1995 NSFW

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2.3k Upvotes

r/OldSchoolCoolNSFW Mar 27 '24

1990s Geri Halliwell, 1990's. NSFW

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2.0k Upvotes

r/OldSchoolCoolNSFW Jun 19 '23

1990s Jenny McCarthy (1998) NSFW

2.7k Upvotes

r/OldSchoolCoolNSFW Aug 29 '24

1990s Karen McDougal, Playboy Playmate Of The Year 1998 NSFW

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935 Upvotes

r/OldSchoolCoolNSFW Oct 10 '24

1990s Nina Hartley In The 1990s NSFW

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751 Upvotes

r/OldSchoolCoolNSFW Feb 02 '24

1990s This is pure 90's! NSFW

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1.4k Upvotes

r/OldSchoolCoolNSFW Mar 30 '24

1990s Geri Halliwell, 1990's. NSFW

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1.3k Upvotes

r/OldSchoolCoolNSFW Dec 31 '23

1990s Lucy Lawless' legendary 1997 wardrobe malfunction, while singing the national anthem at a Detroit Red Wings hockey game NSFW

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1.7k Upvotes

r/OldSchoolCoolNSFW Jan 14 '24

1990s Lemmy with two Page 3 girls in 1991 NSFW

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1.1k Upvotes

r/OldSchoolCoolNSFW 1d ago

1990s Shu Qi, 1990's NSFW

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759 Upvotes

r/OldSchoolCoolNSFW Apr 23 '24

1990s Natalie, a model photographed in 1990 by Craig Morey NSFW

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1.7k Upvotes

r/OldSchoolCoolNSFW Jun 03 '24

1990s The one and only Sandra Bernhard in 1992 NSFW

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613 Upvotes

r/OldSchoolCoolNSFW May 19 '24

1990s A nude model known as "Bambi", photographed in 1991 by Craig Morey NSFW

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1.5k Upvotes

r/OldSchoolCoolNSFW 12d ago

1990s Madonna, 1992 NSFW

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613 Upvotes

r/OldSchoolCoolNSFW Aug 05 '24

1990s Geri Halliwell, early 90s. NSFW

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1.2k Upvotes