Sydney sailing instructor groomed boy

With an ill father, a struggling sailing business and in the throes of depression, Timothy Russell Crossman was not thinking straight.

The then 29-year-old Sydney sailing instructor turned to a teenage boy, a student of his, for someone to talk to.

But his conversations, conducted over Facebook, took an inappropriate and sexual turn.

Crossman pleaded guilty to using a carriage service to procure a person to engage in sexual activity between December 2011 and May 2012.

He was discovered sending sexually explicit messages to his teenage sailing student via Facebook's instant chat message service.

In the Downing Centre District Court on Friday, the crown submitted the messages spread over six months were persistent.

However, of the 47,000 instant chat messages exchanged, the crown could not say how many were sexually explicit.

Crossman asked his victim to send photographs, which he conceded was for his own sexual gratification.

In court on Friday, he explained he was experiencing personal difficulties when the offending occurred.

"My father was quite ill," he said.

"The business that I was running was not going so well financially and I was feeling very lonely and depressed."

Crossman also attributed his behaviour to severe depression.

The court heard Crossman wrote in one message to the boy: "if you are not interested, you are not interested but the offer is always there".

The boy replied that it wasn't for him, but Crossman continued to pursue him, the court heard.

There was also a suggestion the victim wanted alcohol bought for him but there was no evidence that eventuated.

Judge Helen Syme said Crossman was in a position of authority, which made the grooming easier.

She sentenced Crossman to a 15-month suspended jail term.

Crossman was also ordered to enter into a $1000 recognisance to be of good behaviour.