Green’s Dictionary of Slang

(US black) to take advantage of someone.

1953		F. Paley Rumble on the Docks (1955) 135: ‘You’re a real pal!’ He slapped Jimmy on the back. Jimmy shook it off and his face got red with anger. He knew they were trying to lollipop him.
1961		Sat. Eve. Post 11 Mar. 67: Don’t try to lollipop me, Burton. I’m too old to be taken in by a line like that [HDAS].