A company director with a foot fetish and a "Benny Hill" approach to women has been put on the sex offenders' register for two indecent assaults.
Christopher Wood asked his victim to wear his wife's shoes to satisfy his needs, thrust his crotch towards her, joked about her "gag reflex", wanted her to feed him food through a tube and questioned her views on his private parts during "horseplay".
The married dad, who was "rude all the time" while in the woman's presence, also slapped her bottom, which he remarked was "firmer than he thought".
Wood admitted two offences of indecent assault in relation to the woman, who cannot be named for legal reasons.
A judge said the 40-year-old businessman, who works in the security trade, acted like a "social dinosaur" who treated women like the late slapstick comedian Benny Hill - who would chase females around during scenes on his sexually-charged show.
Prosecutor Jonathan Walker told the court the woman's ordeal, which happened in Sunderland, left her traumatised.
He told the court: "He used horseplay to make physical contact. He used sexually charged language.
"He asked her highly inappropriate questions regarding her sexual relationship with her boyfriend.
"He made her deeply uncomfortable. He told her he had a foot fetish. He brought a pair of his wife's shoes. He asked the complainant to wear them.
"He suggested she wore low cut tops and regularly complimented her breasts."
He added: "He asked her about her gag reflex, asked her if she thought he had a large penis.
"He asked her to sit on the floor and feed food down a tube into his mouth.
"He slapped her bottom and said it was a lot firmer than he thought it would be."
The court heard the victim was left "deeply upset" and she told police: "I cannot forget what he has done to me.
"He knew what he was doing and continued without a second thought for me and my feelings.
"He really has ruined my life."
Judge Stephen Earl sentenced Wood, of Highfield Rise, Chester-le-Street to a community order for 18 months with 140 hours unpaid work and five years on the sex offenders' register.
Wood was ordered to pay £3,000 compensation to the victim.
The judge told him: "It is highly offensive, highly inappropriate and frankly the actions of a social dinosaur.
"Sadly, our daily newspapers remind us, this is not a situation where you are the only dinosaur in society. There are many others hanging on as well.
"The days of this Benny Hill approach, treating of woman this way, was unacceptable - was, is and will be."
The judge said the ordeal must have been "awful" for the victim but he commended her bravery and said she must be a "strong woman" to have spoken out.
Jane Foley, mitigating, said Wood now realises his behaviour was "unacceptable and highly inappropriate" and has described it himself as "disgusting".
Miss Foley said at the time Wood believed his behaviour was just "horseplay" but added: "The banter was clearly wrong, sexually charged and highly inappropriate."