At one point, the undercover police officer said the estate agent showed him photos of young boys on his iPhone.
"[The estate agent] said he was 14 years old and he had taken him to bed," the officer told the court.
In one of the recordings played to the court the estate agent can be heard saying: "He's 14 and um, he was very, very yummy... And he was very keen. I took this boy, this boy and that one to bed and this one here was really, really eager to spend the night with me."
The estate agent can also be heard talking about picking up boys in Thailand for sex.
"I mean, I couldn't believe it the first time that I um picked up a young guy, probably, I don't know, 14 maybe, um at a park where some of the locals were, and um I said to him oh f*** you know, how are we going to, and he said oh we just get a taxi..."
A little later on, the estate agent can be heard saying: "...and the taxi driver turns around and says: 'You know this boy's only 14' and I said: yeah, yeah, no that's all right and he said 'but which hotel are you', so he wasn't interested, he didn't care."
Yesterday the court was told that police began a covert investigation after Customs officers at Auckland International Airport found suspicious photographs of the man with young Thai boys.
Crown prosecutor Natalie Walker said the undercover officer, using the pseudonym Michael Grey, emailed the man and expressed interest in travelling to Thailand.
Ms Walker, in her opening address, said they discussed sex in Thailand "at length".
The trip was booked and the man was arrested soon after and charged with organising the tour and operating and maintaining an objectionable website.
She said the man's website did not have any direct reference to sex, but intimated it through "suggestive" language.
Meta data, or coded words to help search engines locate and offer the website when people search for particular words, found on the website included the words: gay, gay sex, Thailand, boys, get together and tour.
"There can be no dispute that the aim of the tours was to have sex with underage boys by paying for it," Ms Walker said.
"This is a man who is sexually attracted to boys and has no moral problem having sex with Thai boys."
The man's lawyer, Chris Wilkinson-Smith, said in his opening address that his client did not dispute creating the website - but it was innocent and purely for travel.
He said the officer was the man's one and only customer in the three years the website had been operating.
"He candidly accepted that yes, he has an attraction to teenage boys. But he is very aware ... of how much care he needed to take not to cross the line," Mr Wilkinson-Smith said.
He said his client used the word "boy" loosely when discussing his sexual experiences and did not mean underage males when using it.
"It can encompass underage boys or be a reference to people aged 18 plus, particularly in a Thai context.
"Referring to a boy in gay culture denotes a social status, rather than a biological age."
The trial continues.
