Top Definition
A boy who dry humps and makes out with his pillow, pretending it is a girl
Ricky, you are such a pillow boy.
by Dpac March 19, 2005
A young, sexually inexperienced boy who masturbates and fantasizes about girls (or boys) with a pillow. Often lonely, and incapable of getting a girlfriend (or boyfriend), explaining the resort to using a pillow. Acts include humping, fucking, and sucking on/making out with.
Billy: "I can't get a girlfriend. I have to resort to using pillows... I'm a fuckin' pillow boy!"
by .Truth. November 16, 2005
a pillow boy is a young man who has sex with an old lady because she is rich and take care of him. like a pool boy.
Dave is a damn pool boy for Mrs. Robinson.
by Mikeagod March 21, 2005
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