Miles Caldwell, 47, who shared an Orpington flat with his OAP mother, received huge payments to book hotel rooms and business class flights, but pocketed the lot.
Even after his arrest on the earlier frauds he targeted more victims, who believed they were dealing with a reputable agent.
The biggest victim was events planner Liz Linkleter - former PA to fashion designer Alexander McQueen - who paid £155,751 to Caldwell, who promised to book 73 wedding hotel rooms, plus flights.
She said: “I am very angry at the way Miles Caldwell has treated my staff and I. We trusted him so did not draw up any business contracts when working with him, which I regret and have learned from.
“Financially, we lost out significantly although I was more worried about how our business would look if I would have had to cancel the wedding event and make clients aware of what really happened.”
She was unaware of Caldwell’s previous convictions, adding: “This could have looked bad on us and had a devastating impact on us as a business.”
Caldwell, of Seven Stiles Court, Ranmore Path pleaded guilty to defrauding Liz Linkleter and her self-titled company between February 6 and May 8, last year.
He also pleaded guilty to defrauding logistics manager Sahra Mirreh, who paid him to book long haul business class flights, out of £52,096 between July 17 and August 27, last year.
Caldwell fobbed her off with lies about airline ticketing delays and even asked for more money, creating dummy booking references to keep her off his back.
“Whilst under an immense amount of pressure I chose to show Miles a lot of grace and patience, not out of naivety, but in the hope he could get this situation sorted, carry-on trading and return the funds,” she said.
“Being unaware of the severity and enormity of his situation I just knew Miles to be an excellent travel agent and a pleasant person when communicating with him.
“This whole incident has left me highly stressed and I feel very angry and frustrated by the situation. I am shocked and stunned that Miles did this to me.
“I felt like he betrayed my trust. I felt like I had built up a good working relationship with him over the years, but now I believe it was based on lies.
“The incident has taken its toll on my mental health and has put me in financial trouble.
“The stress of having to relay what had happened to my clients and trying to find solutions to pay them back their money has been embarrassing and is likely to affect my business relationships going forward.”
Caldwell also pleaded guilty to defrauding events company Hudson Born out of £5,012 between April 4 and 15, this year and £55,800 out of Hippocampus Media on April 10.
Boss Matthew Hudson expected Caldwell to book hotel rooms for a marketing festival and an event involving the Football Association, but quickly became suspicious.
“Nothing in his actions displayed responsibility and I have no doubt he’d do it again,” said Mr Hudson. “I am lucky that my bank has reimbursed me.”
Hippocampus Media were fortunately reimbursed by their bank after transferring money to Caldwell to book hotel rooms, which was never done.
In 2017 Caldwell received two years imprisonment on eight counts of fraud and these latest offences continued even after he made admissions to police.
Major gambling companies have contributed to a compensation fund and Liz Linkleter will receive approximately £15,000 and Sahra Mirreh approximately £5,000.
Recorder Samantha Presland said: “There’s an element of not being able to stop himself. This involves huge sums of money, with sophistication.
“A pre-sentence report will not get him out of a custodial sentence.
“You have brought your overnight bag so are ready to face the music,” she told Caldwell. “You are clearly a very bright man.”
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