Heeling is basically like skating but using Heelys shoes which are shoes with a wheel in the heel.
Guy1: Hey man, i have just bought my new pair of heelys, wanna go out heeling?
Guy2: Hell yeah
The sexual act of penetrating the vagina with your heel. Works best if the penetrator has tiny feet and the penetratee has a monster cunt.
Man I went home with this smokin' hot girl last night but when it got time to do the no-pants-dance, I couldn't get a grip in her vajayjay! So heeling was the only way...