The 24-year-old man was called to the stand as prosecutors in the current molestation case against Jackson began trying to show the jury that the singer has a habit of molesting boys.
The witness said that over a span of several years, Jackson twice touched his groin over his clothes during tickling games at Jackson's Los Angeles-area condominium, which he and his mother referred to as "the hideaway," and in a third incident reached under his clothes at Jackson's Neverland ranch.
Jackson gave him $100 after each of the first two incidents but nothing after the third one, he said.
"We were tickling. He was tickling and I was laughing and the — it was, he was — he was tickling me in the...," the witness said before asking the judge for a break. He wiped his eyes and drank some water.
"He was tickling me. I was wearing shorts again. ... He reached on my leg and I'm still laughing and he reached up to my — privates," the witness said.
As he began to describe the alleged molestation he apologized to prosecutor Ron Zonen for his halting testimony and said: "This took a lot of counseling to get over, just to let you know."
The defense asked that the comment be struck from the record and Judge Rodney S. Melville agreed.
The witness said that Jackson touched him in that incident for two or three minutes and that he remembered thinking, "I should probably go." Asked whom he first told of the incident, the witness said, "Probably God."
Jackson is on trial on charges of molesting a 13-year-old boy in February or March 2003.
Monday's testimony was part of evidence prosecutors hoped would show a pattern of improper sexual behavior by the singer.
"We're at a turning point in this trial," courtroom observer Jim Moret tells CBS News. "We're leaving the allegations about this one boy and about to bring in allegations of other boys."
Judge Rodney Melville ruled a week ago that the jury could hear allegations the pop star molested or had designs on five other boys, including actor Macaulay Culkin and two youngsters who reached multimillion-dollar settlements with the singer.
In his ruling, the judge said prosecutors could mention that the housekeeper's son and another boy received civil settlements from Jackson but could not tell the jury the amounts. Prosecutors have said the housekeeper's son received $2.4 million in 1994.
The housekeeper's son, now married and working in an anti-truancy program, was asked at the outset of his testimony if he could identify Jackson in court.
"He's the light-complected gentleman," the witness said, smiling at Jackson.
The witness also described two earlier alleged incidents that involved Jackson touching him over his clothes.
"We were watching cartoons and he just started tickling me, which was — cool," he said of the first incident, which he described as beginning while they were seated in a chair and then later on the floor.
"It eventually moved down to my little private region, I guess ... around my crotch area. You know, you're 7, you didn't think it was wrong. ... I probably did think it was weird but not super-weird because you were tickling," he said.
In another incident, he said, Jackson began tickling him as they were cuddling on top of a sleeping bag while watching cartoons. He described the tickling proceeding in the same way.
CBS News Legal Analyst Andrew Cohen said the witness presented "damning details" without the excess baggage the accuser brought to the stand. His credibility wasn't in question, so Cohen said he put Jackson's defense in a hard place.
"This is precisely the sort of testimony that Jackson's attorneys feared when they fought so hard last week to convince the judge that it shouldn't be a part of this case," Cohen said. "They knew it would be devastating, and hard to overcome, and it was and is."
The witness said he never talked about the incidents with anyone until 1993, when investigators came to him after another boy made allegations against Jackson in a civil case. The other boy also would later receive a settlement, reportedly in the multimillion-dollar range. No criminal charges were filed in either case.
On cross-examination, Jackson attorney Thomas Mesereau Jr. sought to show that the witness' mother had a financial interest in his story, asking if she had received $20,000 to appear on the television show "Hard Copy."
The witness said he learned of the payment just days ago, but saw the show when it aired. He said he didn't know if his mother ever met with The National Enquirer.
The witness also testified that he told police he tried to block out the memory of the tickling episodes. "I didn't want to ever talk about this stuff again," he said.
Mesereau inquired whether police had once asked the witness, "This is what happened, right?" to which the witness allegedly replied, "I'll have to work on that."
The young man said he had no memory of making that statement.
The witness also was asked why, when he first talked to police, he denied anything had happened. "I was scared," he replied.
Jackson fans who showed up over the weekend to rally on his behalf also stayed for Monday's court session, chanting and shouting when he arrived and later as he went home for the day.