What is Pillow Boy?
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
Billy: "I can't get a girlfriend. I have to resort to using pillows... I'm a fuckin' pillow boy!"
See
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.
