Tarjit Singh, who was born a female named Hannah Walters but now identifies as a man, was dubbed "controlling and manipulative" for his crimes in court.
He had abusive relationships with each of his three victims between June 2010 and March 2016.
Singh, 32, wore clothes during intercourse and used strap-on sex toys in the dark.
He was convicted of three counts of assault by penetration, six counts of assault occasioning actual bodily harm, and one count of making a threat to kill, after a trial at Snaresbrook Crown Court earlier this year.
Singh, of Enfield, north London, kept his head down throughout the sentencing and was jailed for a total of 10 years in prison with another three years on licence.
A sexual harm prevention order was imposed.
Tarjit Singh, 32, wore clothes during intercourse and used strap-on sex toys in the dark
Judge Oscar Del Fabbro told Singh he represents a “risk to the public of serious harm in the future” and described him as a “dangerous offender” who had committed repeated acts of violence and assaults against three “vulnerable” victims.
The victims lived in a “dangerous environment for them, riddled with violence” with Singh and problems he caused them emotionally, the judge said.
He added that Singh had not been “open and honest” about his gender issues, describing him as “an accomplished and manipulative liar”.
The judge told Singh he had been “aware that these women were vulnerable” and deceived them by “not truly revealing” that he had been born biologically female.
He said: “Instead of opening a frank and honest discussion about your gender and how you wanted to live your life, you chose a different path – you chose a path of deceit.
“You persuaded them you were male and acted like you were male.”
His troubled victims included a teenage girl who had just turned 16 and two women who had been previously sexually abused.
Snaresbrook Crown Court
PA
The judge added that they must have been taken in by his charm, humour and the fact that he appeared willing to lend them a “sympathetic ear".
"Nothing could be further from the truth," he added.
The judge praised the victims and their families for “reliving the trauma” of the “gruelling” events by giving evidence during the trial to ensure Singh faced justice.
The court previously heard that when the victims began to ask questions, Singh became abusive and manipulative.
He told one of them there was more to a relationship than sex and that she should learn to talk about her feelings more.
Describing the sexual contact, one victim said: “He looked like a guy, he acted like a guy.”
The victim only discovered Singh had female genitalia after finding a sex toy some months into their relationship.
She told police she felt “so stupid” that she had fallen for such lies.
Singh told another victim he had been born male, had a sex change to become female, and now wanted to be male again.
The third victim met Singh after receiving a message through the dating website Plenty of Fish in 2014.