Being "Hit like Holyfield" means that the girl sleeps around a lot. She has been "hit" by many different guys.

The fighters that fought Holyfield typically took many punches and the fights lasted the full 12 rounds. There were "hit" many, many times. A girl that has been "hit like Holyfied" is probably not safe and also has STDs.
Brad: Damn, that girl over there is a dime.
Homewood: Hell yeah, but she has been hit like Holyfield so you know you will be at the free clinic on Monday wondering what is dripping from your cock if you settle for her tonight.
by ERP October 25, 2007
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used when something is serious, but not serious enough to be an emergency -- a joking way to depict an event as significant.
"We just won tickets to the superbowl!!!"

"Are you kidding me?!"

"No, this is the real deal holyfield"
by VBR213 October 14, 2009
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(Verb) The act performed when a human who is younger in age Brutally Embarrasses, Whips & Spanks (Debo's) a human of elder decent shamelessly and mercilessly resulting in a KO. This act must be performed in publicly.
Boy 1: So I went to go pick up that hottie, Aru, for the prom and guess who was there bro?
Boy 2: WHO WAS THERE BRO!!
Boy 1: Like 20 people from her family!! All taking pictures. Especially her big old DAD. He kept asking when I would have her home.
Boy 2: So what did you do?
Boy 1: I grabbed his daughters tit (Consensually) and HOLYFIELDED his ass!!!!.
Boy 2: In front of everyone bro?
Boy 1: KO Mother Fucker!!!
by September 12, 2021
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(Verb) The act performed when a human who is younger in age Brutally Embarrasses, Whips & Spanks (Debo's) a human of elder decent shamelessly and mercilessly resulting in a KO. This act must be performed in publicly.
Boy 1: So I went to go pick up that hottie, Aru, for the prom and guess who was there bro?
Boy 2: WHO WAS THERE BRO!!
Boy 1: Like 20 people from her family!! All taking pictures. Especially her big old DAD. He kept asking when I would have her home.
Boy 2: So what did you do?
Boy 1: I grabbed his daughters tit (Consensually) and HOLYFIELDED his ass!!!!.
Boy 2: In front of everyone bro?
Boy 1: KO Mother Fucker!!!
by September 12, 2021
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