A convicted sex offender offered a 14-year-old girl hundreds of pounds to meet him in her school uniform so he could "give her pain".
"Sinister" Gerald Niven told the teenager he would give her £250 if she would let him spank her with a belt.
The indecent offences came two years after Niven, a former director of a Dundee house building company, completed a probation order for an almost identical offence.
In 2003 and 2004 he paid teenage girls as young as 14 that he met on internet chatrooms up to £200 to let him engage in indecent behaviour.
During the latest offence, he befriended the schoolgirl on social networking site Bebo using the fake name Mark Thomson.
Dundee Sheriff Court heard on Friday the girl had received a friend request which she accepted, thinking it was someone from school.
Fiscal depute Emma Stewart told the court: "Some time later she received a message from this person asking 'Fancy making some quick cash?'
"She was curious and exchanged further messages with this man, which revealed he was a 35-year-old man from Dundee."
Niven then had private online conversations with the girl, who had revealed her age, and offered her £250 if she would meet him in her school uniform and let him "give her pain".
Ms Stewart added: "She asked what the 'pain' was and he replied he would belt her on the hands and bum. She declined his offer and told him she was not interested."
Niven, who now works as a telesales operator, then twice offered the girl more money, which she refused.
Police were then called after the girl showed the messages to family members and school staff. He claimed during an interview that he had not committed the offences blaming someone sitting outside his house who had tapped into his unsecured wi-fi network.
The 36-year-old, of Bradbury Street, Dundee, admitted that between February 4 and March 24 last year he made arrangements to meet a girl under-16 to engage in unlawful sexual activity.
Advocate Susan Duff, defending, said Niven was "fully aware" that he could face a jail term.
She added: "I would wish to address your lordship on his behalf at the later sentencing date given the position he is in."
Sheriff Richard Davidson deferred sentence until later this month for social background reports.
He said: "I regard this as particularly sinister and he should by no means think he is avoiding a custodial disposal. A risk assessment, standing the nature of the offence, is vital."