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Sharon Kane (the American) fucked a tranny in Passage thru Pamela, in the early 80s. There are a couple of other tranny films on her filmography (998 titles!) at IAFD but I don’t know how far she went in them.

Lois Ayres fucked a tranny in She-Male Vacation (1985), as did Sheri St Claire. Lois AYRES’ filmography has several other transsexual titles I haven’t seen.

In the pseudo-biopic Twice a Virgin, from abt 1983, pre-op Shannon got blown and fucked by Becky Savage and a redhead, in a T/F/F sequence (no cum shot), plus a simulated scene with a tiny-titted and incredibly-tanned Michelle Bauer. Shemale model Shannon also did an M/F/T threesome set for Hustler around 1984 (the set is softcore, as shown in the mag.) I vaguely remember a softcore set in US Club International from the very early 80s, with a girl photog shooting a limp-dicked tranny model — my memory says, tentatively, that Hillary Summers was the femme in the set. Seems to me there were one or two other F/T sets in Club Int of that period, though I may be thinking of the ‘Boston Bat-Wanger,” who as I recall was a fake hermaphrodite. One of these sets had a chick-with-a-dick and a blonde in a maid’s costume, and I think there was another with a tranny in femme clothes and a femme in male attire.