Jenna Jameson - Jenna Ink (Accidental Anal Poke) (Anal Play) (Simulated Double Penetration with Dildo) (Infamous)

The legendary Jenna Jameson gets accidentally poked in her ass during a repeatedly haphazard cock motion in this infamous scene at around 5m 26s (reaching back and giving him a smiling "you were purposely not being careful you bastard" look after it happens). He also starts fingering her ass while fucking her at around 10m 02s. Additionally this is also the only scene I am aware of where Jenna performs a simulated DP with a male co-star at 11m 28s... even letting him take control of the the anal vibrator for a little while. For those who always wanted to see Jenna Jameson perform anal onscreen but were left disappointed... this scene is the closest you will ever get. With the added bonus of Jenna looking amazing because she was still in her prime.