Green’s Dictionary of Slang

1. (US black) an effeminate homosexual man.

1934		H. Sebastian ‘Negro Sl. in Lincoln University’ in AS IX:4 288: skippy A sissy.
1935		E. Freeman ‘The Whirling Hub’ in Afro-American (Baltimore, MD) 23 Feb. 15/1: What local Joe Rank pleaded with a certain gossip columnist to soft-pedal the romance between Connie Simms and a certain skippy.

2. (US campus) an over-energetic person.

1999

Eble Campus Sl. Apr.