Green’s Dictionary of Slang

kiss-my-ass adj.

also kiss-my-arse, kiss my back cheeks, kiss-my-tail
[kiss my arse! excl. (1)]

1. a general pej.

[UK]‘May Day Morning’ in Capt. Morris’s Songs in Spedding & Watt (eds) Bawdy Songbooks (2011) III 222: No blast me, says Satchel arse Jackey — / I shan’t drink no kiss my arse chaps / As what claps a new tax upon ’baccy.
[UK]G. Lamming Emigrants (1980) 63: Dat is a lot a kiss-me-tail nonsense.
[US]S. Longstreet Flesh Peddlers (1964) 181: It’s depressing, this fake O’Casey, fake Joyce, Ole Sod of Erin kiss-my-arse place, isn’t it?
[WI]S. Naipaul Fireflies 167: But don’t try and play too smart with me. Is not I who make the kiss-me-arse plug.
[WI]A. Clarke Growing Up Stupid Under the Union Jack 65: An inswinger that travelled at ‘ninety kiss-me-arse miles an hour, boy!’ .
[US]S. King Gerald’s Game (1993) 262: Just some swinging dick [...] playing Paul Kiss-My-Ass Bunyan, roaring away with his Stihl.
[UK]‘Q’ Deadmeat 46: We see one ah dem kissmearse Movin Shade man.

2. arrogant, undaunted, proud.

[US]S. Ace Stand On It (1979) 94: What he meant was that yer gonna grow up into a regular kiss-my-ass, mean bugger.
[US]S. King Dolores Claiborne 303: ‘What can you be thinking about, Dolores?’ she ast in that haughty Kiss-My-Back-Cheeks voice of hers.
[US]Source Oct. 116: George Jefferson’s blunt language and kiss-my-ass attitude.