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Condom Cum Swallowing & Bareback Dirty Ass-to-Mouth: Anal Assfucking Humiliation from Britney Swallows' Vintage Teen Archives (1999-2019)

Daniella Rush was 29 years younger than Randy West when she fucked him in 1999. In a very sensual scene, he not only came in her pussy, but he also gave her ass special attention (including his famous cock). Full scene link in comments.

EXTENDED: Danielle Rogers doing anal in Chamber Of Whores 2: Porn World (1999)

Malone Contro Tutti (1999)

Silvia Saint does one of her first double anals ??. Circa 1999

Daniella Rush (Maximum Perversum: Junge Fotzen, Hart Gedehnt, 1999)

Danielle Rogers - Anal Doggystyle and Reverse Cowgirl (1999)

Silvia Saint - Hotdorix (1999)

Danielle Rodgers - Chamber Of Whores 2: Porn World (1999)

Sylvia Saint (1999)

Briana Banks (First Anal) - Kelly the Coed 5 - (1999)

Bonita Saint - Pickup Lines 40 (1999)

Ashlyn Gere was my favourite porn star in the early 90’s. She took time out to do some mainstream stuff like the X-Files, then came back at 40 to do more extreme porn than she’d done before, like Tom Byron’s Whack Attack series… 1999

Nikki Anderson - Hot Sex on the Riviera (1999)

[Meridian] Anal Riding | Babettes Saftbienen (1999)

Lidija Sunjerga [HR] - Das diebische Trio (1999)

Sonia Russo - Il Mostro dell'autostrada Napoli-Roma (1999)

Hungarian Sylvia Laurent getting fucked hard by Rocco Siffredi's big dick on a motorcycle in True Anal Stories 7 (1999)

Laura Bellini - Network (1999)

Stacy Valentine in Forever Night (1999)

Tavalia Griffin in Sexual Society 2: Push It Through (1999)

Karma Rosenberg in Rocco's True Anal Stories 6 (1999)

Zana Sun a.k.a. Kitty Jung [Beach Bitches, 1999]

Jazmine Rose [North Pole 7, 1999]