Turn of the century, fin-de-siècle Paris was iconically represented by the painter Henri Toulouse-Lautrec. Lautrec is well known for portraying a frank insider’s view of the societal underworld including the drunken corners of bars and the revelry of the Moulin Rouge dance-floor in the area of Montmartre that he called home. However, there are a few of his paintings that stand apart from the rest of his body of work. The sapphic figure studies of 1892 and 1895 are complex and delicate works that have little to no scholarship about them. This paper will investigate these paintings in depth taking into consideration the biography of Toulouse-Lautrec and the controversy of the sapphic woman during the time of their production. Lautrec’s extensive oeuvre of work is most well known for embodying the debauchery of the setting but the obscure paintings of the sapphic women he knew reveal a more sensitive approach to his art. The works in question of female couples together are not obscene or excessive but are intimate and raw. The sapphic woman during fin-de-siècle Paris was not typically painted in this demeanor, but rather were portrayed to be an image of sex and fear of the upcoming century. From piecing together clues and comments it can be said that these paintings were figure studies and therefore planned poses of intimate acts that revel more about the artist himself and his chosen subject.