Pillow Boy Edit Meaning

1.

A boy who dry humps and makes out with his pillow, pretending it is a girl

Ricky, you are such a pillow boy.

2.

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!"

See loser, unlucky, desperate, sex-crazed, horny

3.

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.