Wegman was born as an androgynous person,[5] and felt like a woman since 1960.[10] Janine was known as the first transsexual person in Rotterdam to present in public as a woman in the late 1950s. Together with trans pioneers such as Aaïcha Bergamin,[11] she was one of the first people in the Netherlands to openly manifest herself as transsexual.[12] She was being treated by Dr Otto de Vaal[13] and received hormone tablets.[14]
Since 1959 there was a General Police Regulation in Rotterdam in which Article 56, “Walking in disguise or masked”, was used to prevent transvestism. Section 1 read: "It is forbidden to show oneself on the road in the clothing of the sex to which one does not belong."[15] Wegman was regularly arrested by the police for walking down the street in women's clothing. She had a run-in with the police after hitting a police officer in the face in the Benthuizerstraat, after which six police officers beat her up until she bled.[16][5]
She had to try for several years before she could become a member of the COC, a Dutch organisation for LGBT people.[7]
In 1978 Wegman managed to change the name in her passport to Johanna Maria Wegman through a lawsuit. In an attempt to get the V for Female in her passport, she showed her breasts several times at City Hall. After the first action in 1978, a civil registry officer scratched the V for Female in her passport, but this was not a legally valid change. After her second action in 1995, the registry office stated that there were no valid documents of gender reassignment,[17] which was a prerequisite for gender reassignment on ID cards between 1985 and 2014. In 1996, after being castrated, and again appearing bare-chested at the counter and threatening with suicide, Janine Wegman was finally allowed to register as a woman at the registry office.[18]