Gender bending: 1595

It wasn't considered moral (or legal) for women to perform on stage, so all shows were drag shows.

Now, imagine Romeo and Juliet like this:



...because it was the norm.

Baby safe: 1630

Yeah, it's a boy in a dress again. But what's that stabby thing in his hand, on the strangly necklace wrapped around his neck? That's his pacifier. It's a rock.

Boy wearing a dress: 1659

How dainty! All part of a traditional upbringing.

Sexy Tranny, circa 1600

I grew as impudent a thief, and as dexterous as ever Moll Cutpurse was, though, if fame does not belie her, not half so handsome.

--From Moll Flanders--

Moll Cutpurse, AKA Mal Cutpurse, AKA Mary Frith; thief, pimp and cross-dresser. She was also known for smoking which was said to have added years to her life.

Boy wearing a dress, 1849 edition

Everyone was doing it.

Voyeurism, 1781 edition

Two ladies getting ready to kiss, and a putto watching in the background. Dirty! But have the woman in blue (Diana) be the God Jupiter in disguise (the final title was Jupiter and Callisto) and everything is fine. So, if you're ever worried about lesbianism offending people, just make one of the women a transvestite and everything becomes tasteful.