Take this 17th-century portrait of a lady preparing food while a black servant gives her an expression that seems to ask "Why are your boobs out?" The woman in the picture is Nell Gwyn, comedic actress and mistress to English King Charles II, who sent this lusty portrait to her lover sometime during their 16-year affair. The very suggestive piece shows a virginal white Gwyn flash ample cleavage while "stuffing sausages," which we'll assume was the Renaissance equivalent of sending the eggplant emoji. The original picture, made by a wisely anonymous painter in the late 17th century, is only a little larger than a postcard -- not big enough to hang on a wall, but probably just about the right size to carry around in a king-sized pocket and show to his ducal bros.
Flash-forward to 1828, and this self-portrait by Boston painter Sarah Goodridge might be the first sext selfie. And unlike Gwyn, Goodridge knew there was a quicker way into a man's unmentionables than some subtle iconography:
She sent this as a gift to none other than U.S. senator Daniel Webster. It's a miniature painting, measuring around 2x3 inches, which was popular at the time. Pretty useless for display, but handy for, say, keeping it hidden from your wife. Webster and Goodridge insisted they were only close friends, and historians have found no evidence they were doing the wild thing. Except, of course, for exhibit Double D.