Green’s Dictionary of Slang

1. (US) to get on well with someone.

1993		Source Sept. 48: I kick it with everyone.
1995		L. Stavsky et al. A2Z 60: kickin’ back, kickin’ it – relaxing, hanging out: I’m just coolin’ out and kickin’ back.

2. (US) to associate with.

1992		UGK ‘Cocaine in the Back of the Ride’ 🎵 Kick it with a trill nigga so you best not trip.
2000		W. Shaw Westsiders 53: Any group of boys kicking it together would give themselves a name — usually a three- or four-letter acronym.

3. (US black) to have an affair over and above one’s primary, monogamous relationship.

1994

G. Smitherman Black Talk.

4. (US black/prison) to have sexual intercourse.

1999		‘Master Pimp’ Pimp’s Rap 64: Do you believe they’re still kicking it?
2003		A.N. LeBlanc Random Family 123: All of Cesar’s friends had tried to kick it to her.

5. (US) of a man to a woman, to make suggestive comments.

2003

A.N. LeBlanc Random Family 303: The boys started kicking it to me you know trying to talk to me. One boy was like what’s up cutie.