Jennie June was born into a Puritan family in 1874 in Connecticut as Earl Lind. As a child, Lind asked others to call her by Jennie instead of Earl, and she spent much more time with girls than with boys. She became very shy and introverted when her parents sent her off to an all boys school and also became very depressed, considering suicide. Lind realized at a young age that she was an androgyne looking to change from male to female. At the time, the term "transgender" had not been coined; instead words such as "androgyne", "invert", and "fairie" were used. She struggled throughout her life up to her late twenties with her extreme desire to perform fellatio, claiming to have partaken in over sixteen hundred sexual encounters in the span of a dozen years. As a young adult, June found safe havens in places such as Paresis Hall in New York City to take on her new identity. Paresis Hall, or Columbia Hall, was one of many establishments considered the center of homosexual nightlife where male prostitutes would do as female prostitutes did, soliciting men under an effeminate persona. Places like Paresis Hall provided a place where people like June could gather and feel more free to express themselves and socialize with similar people in a time when cross dressing was socially unacceptable and illegal. June then formed the Cercle Hermaphroditos in 1895 along with other androgynes who frequented Paresis Hall. The organization was formed in the hopes "to unite for defense against the world's bitter persecution" and to show that being transgender was natural, although there is not much solid evidence that this organization actually existed. At the age of 28, June had herself castrated, a decision that she believed would make her healthier and decrease her extreme and "disturbing" desires for sex, as well as eliminating some of her other masculine features, such as facial hair. According to Wayne Koestenbaum in The Queen's Throat, she believed that she could 'diagnose a man sexually simply by hearing him sing', and wanted to be an opera soprano.
''Autobiography of an Androgyne'' and ''The Female-Impersonators''
June published her first autobiography, The Autobiography of an Androgyne in 1918, and her second The Female-Impersonators in 1922. While June did not describe herself as transgender, since the term was not in use yet, she aligned herself with femininity, despite having been assigned male at birth. This makes her one of the earliest instances of someone who is transgender or gender nonconforming in American history to publicize her own story. In her preface to her book, June explains that she has kept diaries of her life and that her autobiography has been taken from those. June self-identified as a "fairie", "androgyne", "effeminate man", and a passive "invert". She did not separate her gender from her sexuality, as was typical of the time period, and she also tied age into that, feeling as though age changed how and what people desired. She organized the book into episode-like sections, wherein she discusses incidents in her life as well as her opinions on certain social matters. Her goal in writing her book was to make her trials well-known and to rally the support of Americans to create an accepting environment for young adults who do not adhere to gender and sexual norms because that was what she would have wanted for herself, and she wanted to prevent them from committing suicide. June discusses her desires, which she struggled with because they were so different to what was considered normal. The memoir describes in detail many personal narratives as well as her sexual encounters and desires, including the story of her castration, but also contains pleas for understanding and acceptance of these "fairies". The Autobiography of an Androgyne also describes how June felt that she lived a double life in the sense that she was an educated, middle-class white male scholar but also had intense yearnings for performing sexual acts that actually distracted her and caused her suffering.
''The Riddle of the Underworld''
In 2010, Dr. Randall Sell, a professor at Drexel University, discovered a third volume of June's autobiography called The Riddle of the Underworld, which was written in 1921. This third volume includes an encounter in which June was beaten by men whom she tried to pick up. She once again defends gender and sexual nonconformists, insisting that they were simply born of a different nature, but natural nonetheless. These newly discovered volumes provide an opportunity to look into more of June's deeply personal encounters and issues, and provide the possibility for other narratives to exist.