Vintage Crossdresser Porn Videos

Crossdressing, as referenced in ancient folklore, literature, and music, refers to when an individual wears traditionally or stereotypically reserved clothes for the opposite gender. It would appear that cross-dressing is a longstanding practice that has existed for centuries in theatre, music, religion, and for other reasons like comfort, disguise, and as an act of expression.

Crossdressing was a typical act in English medieval and renaissance theatre, often executed by boy players cast as women in plays. Soon enough, crossdressing was incorporated into vintage porn scenes, as exhibited in these vintage cross-dresser porn videos.

The scenes from these retro stag films depict naughty men and women in the other gender's clothing. The men wear dresses, skirts, and heels, among traditionally female outfits. At the same time, women wear male hats, boots, coats, and trousers as part of a bizarre sexual act.

One scene from the 1960s shows angry whores humiliating their rich pimp by dressing him up as a woman and asking him to pleasure them all, licking pussy and fucking each one of them to gratification. Watch the ancient crossdressers, including the deviant 1920s flappers, to the kinky perverts of the '70s all under this page.