Ammar Haider, from Birmingham, told three woman a series of "sob stories" to get them to part with savings, take out loans and even pawn possessions, totalling £120,000, police said.
The married father-of-two said he was a trainee pilot, ill relatives needed expensive medical treatment and he was stuck in a dangerous jail in Dubai.
He admitted three charges of fraud.
When West Midlands Police looked into his finances, officers said they found transactions from other victims who had apparently been bullied into not reporting Haider to police because he pretended to be a feared gangster and threatened them and their families.
Haider first made contact with a woman from Sheffield, in 2011, having stolen her personal details from a customer database at the car insurance centre where he worked in Sandwell.
He began flirting with her via text message before they agreed to meet.
He told her he was a trainee pilot with Emirates Airlines. She ended up giving him £9,000 towards his ill father's emergency "treatment" and other bills.
The woman, who went on holiday to Austria with him, was later contacted by his wife confirming that, along with other women, she had been tricked, police said.
The 28-year-old from Acocks Green also told a woman from Edinburgh whom he met through a dating site that he needed £45,000 in bail money to escape torturers inside a Dubai prison, police said.
She gave him a total of £52,000 but became suspicious when she checked with authorities.
In police interviews, Haider said he knew the three women but said they had willingly handed over money and made up lies about him when he ended the relationships.
Det Con Debra Phillips, said his victims - all well-paid professionals - now had long-term financial problems.
"They were cynically targeted by Haider because of their financial means. At one stage he was juggling relationships with his wife and two girlfriends."
Haider admitted the charges last month at Birmingham Crown Court and was sentenced on Wednesday.
A serial liar who tricked women he dated out of tens of thousands of pounds has been jailed for five years.