Green’s Dictionary of Slang

1. (US, also heel-and-toe it, heel-toe) to run or walk quickly (cites 1876, 1903 refer to competition walking).

1819		Chester Chron. 23 July 4/1: This is the day for toeing and heeling it, / All are promenading it from high to low.
1844		J. Overs Evenings of a Working Man 187: Don’t he toe an’ heel it scrummy!
1876		Graphic (London) 18 Mar. 17/2: Weston walked 450 miles in six days and nights, ‘fair heel and toe’.
1893		Yorks. Eve. Post 19 Oct. 4/3: A writer on dancing estimates that eighteen waltzes are equal to about fourteen miles of heel-and-toe work.
1903		Grantham Jrnl 30 May 2/5: Miss Minnie Letta acoomplished a fine performance by walking, fair heel and toe, from Redhill to Brighton.
1932		M. Marshall Travels of Tramp-Royal 48: ‘No – no – NO!’ said I, heeling and toeing it.
1949		Monteleone Criminal Sl. (rev. edn).
1955		B. Schulberg On the Waterfront (1964) 25: He heel-and-toed along River Street.
1964		J. Gelber On Ice 244: They heel-and-toed it toward the door.
1993		H, Mantel ‘Harley St’ in Assassination of Thatcher (2014) 105: What did I see/ Only Liz bathurst heel-toeing it along.
1999		Guardian G2 28 July 9: I sat watching the seven-year-olds heel and toe it [...] across the playgound.
2004		T. Dorsey Cadillac Beach 254: ‘We have to go now.’ Mahoney nodded. ‘Blow, hoof, dust, fade, breeze, slide, heel and toe, grab sidewalk, leave leather, drivin’ the shoe car . . .’.

2. to dance; thus as n., dancing.

[1825		T.C. Croker Fairy Legends and Traditions of the South of Ireland (1862) 30: Heel and toe and cover the buckle are Irish [dance] steps].
1829		‘Pickpocket’s Chaunt’ (trans. of ‘En roulant de vergne en vergne’) in Vidocq (1829) IV 262: And we shall caper a-heel-and-toeing, / A Newgate hornpipe some fine day.
1845		Exeter & Plymouth Gaz. 17 May 4/1: Wants to dance in the fashion. oh! [...] Kickers floor cum heel et toe.
1847		A. Smith Natural History of the Gent 53: He will launch off into all sorts of toe-and-heel tomfooleries [...] at Jullien’s and Vauxhall [...] and other ten-and-sixpenny demi-public hops.
c.1849		‘One of the Boys’ in G.S. Jackson Early Songs of Uncle Sam (1933) 58: Then dancing I know beans [...] At heel and toe, oh I’m one of the boys!
1853		S. Northup Twelve Years A Slave 181: ‘Dance, you d---d niggers, dance,’ Epps would shout. [...] ‘Up and down, heel and toe, and away we go,’ was the order of the hour.

3. to have sexual intercourse where the man’s strokes are very long, deep into the vagina and then almost all the way out.

1889

C. Deveureux Venus in India I 42: Heel and toe is beginning each stroke from the very beginning and ending it with the very end. Just give me one long stroke now! [...] that’s it! You almost pull it out, but not quite, and never stop short in your thrust, but send your prick home, with a sharp rap of your balls against my bottom!