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1.
A sexy man that cleans the pools of the rich and famous. They are notoriously known for doing the trophy wives of the rich and famous. But then again, they're usually very hot.
Wife: Well the Pool boy is doing great today.

(gay)Husband: Hah. I know he was doing great last night.
by Kat Goblet May 31, 2005
 
2.
A handsome, studly, but officious young man who services the pool and the lady of the house with great skill
After the pool boy rinsed the filter, he gave the housewife a spin.
by Ass Clown77 March 07, 2008
 
3.
A "pool boy" is literally a servant who cleans pools.

The slang definition is a man who is a pushover and cleans up everyone else's mess. He takes crap from everyone, and lets people take advantage of him.
Gee, Robert is pool boy, I can make him do anything and not give him anything in return.

by bigballofyarn February 22, 2008
 
4.
Maneuver by which a man who is performing anal intercourse ejaculations in woman ass then proceeds to urinate in her ass.
"She's hot."
"Yeah i'd give her the poolboy."
by rodan April 11, 2004