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1.
To bring a girl home and wait for her to use your bathroom before jerking off on her pillow. You then proceeds to initiate intercourse - doggy-style - before pushing her face into the soiled pillowcase.
"Yeah, dude, she had no idea, but I was totally pillowing that chick last night."

"Awesome, you should save that pillowcase for next time."
by awthedarx December 26, 2011
 
2.
Acting as a place for someone to rest their head for an extended period of time. Utilizing either the breasts or buttocks for maximum comfort.
"Taylor's just sitting there while Kyle has his head in her cleavage."

"Yeah he's super tired so she's pillowing for a while. She's a professional with those 34 dd's"
by kbizzd October 24, 2011
 
3.
The act of covering ones self or another with pillows, such that you are not visible to anyone in the room or cuddle puddle.
Did anyone see Ella?" "I'm right here, I'm just pillowing!
by NomadicEntrepreneur August 04, 2011