Former Nissan worker Alan Barrie, 24, shouted a sickening tirade of hateful slurs and sexual questioning at the woman, who was travelling from North Tyneside for a night out in Newcastle with a friend.
Newcastle Crown Court heard the victim, who has undergone gender reassignment to become female, was forced to leave the train before her destination.
She was left "extremely distressed" by the abusive attack by a man who was a stranger to her.
Barrie, of Selby Gardens, Walkergate, Newcastle, pleaded guilty to a public order offence.
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The court heard Barrie shouted "highly offensive" abuse when he spotted the victim on the train, including a threat to knock out her teeth, and questioning her sexual preferences.
While out on bail after the incident in February last year, Barrie broke into a house of a woman he knew suffered from arthritis and osteoporosis, the court was also told.
He then pushed the victim, who returned home during the offence, as he tried to get away.
The 24-year-old pleaded guilty to burglary and assault in relation to the raid. At the time of the offences he was on a suspended sentence for violence.
Mr Recorder Richard Woolfall sentenced him to a total of two years and 10 months behind bars.
The judge said Barrie's shocking train comments were "utterly odious" and added: "It is clear you are ashamed, in the sober light of day."
Mark Saunders, mitigating, said Barrie started to "fall apart" after the death of his brother and started to misuse drugs, despite having a good job at the car plant.