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.

French media reported that a five-year deal had been agreed to host the race at Le Castellet, near Marseille.
Ecclestone told Reuters: "Yes, I think it will happen," adding that it would be held in late July, not a month later as the initial reports had suggested.
France hosted the first ever grand prix in 1906 but lost its slot in 2008.
There have been several attempts since to revive the race but this one looks to be the first to succeed.
A news conference has been organised for an announcement about the future of the French Grand Prix in Paris on Monday, to be hosted by Christian Estrosi, the president of the Regional Council of Provence-Alpes-Cote d'Azur.
The French sports newspaper L'Equipe reported that a five-year deal had been agreed with the Provence-Alpes-Cote d'Azur region in association with the city of Toulon, department of Var and the French motorsport association.
Le Castellet - also known as the Circuit Paul Ricard - last hosted the French Grand Prix in 1990. From 1991-2008 it was held at Magny-Cours in central France.
Ecclestone's family trust owns the track but the 86-year-old said: "It's nothing to do with them at all. I think they are renting it to the people that are going to be the promoters."
He said the race would be held on "more or less sort of the German date probably", without specifying what that meant for the future of the German Grand Prix.
That race has dropped off the calendar for next year because the Nurburgring, one of two venues that alternate as hosts, cannot meet its financial obligations under its contract with F1.
But Hockenheim, which held the race in 2016, has a contract to do so again in 2018.
The return of France will be greeted with widespread delight by both F1 insiders and fans of the sport.
This is because of its historic significance and because it is another race in the sport's heartland of Europe rather than, as has been the recent trend for new events, in a country where the sport has limited support and no heritage.
F1 is in the process of being bought by US group Liberty Media, and it has said that protecting races in F1's heartland is a major priority, along with expanding its presence in the US, the rest of the Americas and Asia.
A serial liar who tricked women he dated out of tens of thousands of pounds has been jailed for five years.
[NEXT_CONCEPT]
The French Grand Prix will return to the Formula 1 calendar after an absence of 10 years, the sport's boss Bernie Ecclestone has said.