Lasse Braun - Pionierin des Pornos
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From Wikipedia: "The first filmed double penetration in history appeared in 1970, in the movie "Delphia the Greek", by director Lasse Braun."
This video popped up in my recommended list and I thank the algorithm for it. At 41:11 starts the first porno I ever watched over 40 years ago. A little digging on IMDB tells me the title is Top Secret: Dr. Wu.
Collection of Lasse Braun loops, 1st series is Tropical, then moves to the Top Secret series, typically 3 shorts per series. havent figured out the rest yet
1969-1970s
Looks like 1966