Etymology From Middle English tipto, typto; equivalent to tip + toe. Compare fingertip.
1
Standing elevated, on or as if on the tips of one's toes.
Night's candles are burnt out, and jocund day / Stands tiptoe on the misty mountain tops.c. 1591–1595 (date written), William Shakespeare, “The Tragedie of Romeo and Ivliet”, in Mr. William Shakespeares Comedies, Histories, & Tragedies […] (First Folio), London: […] Isaac Iaggard, and Ed[ward] Blount, published 1623, →OCLC, [Act III, scene v]:
And ever as they talked Beregond was more amazed, and looked with greater wonder at the hobbit, swinging his short legs as he sat on the seat, or standing tiptoe upon it to peer over the sill at the lands below.1955 October 20, J[ohn] R[onald] R[euel] Tolkien, “Minas Tirith”, in The Return of the King: Being the Third Part of The Lord of the Rings […], New York, N.Y.: Ballantine Books, published December 1978, →ISBN, book V, page 39:
2
Moving carefully, quietly, warily or stealthily, on or as if on the tips of one's toes.
with tiptoe step1782, William Cowper, Expostulation:
And stole along on tiptoe tread1819, Lord Byron, The Prophecy of Dante:
Etymology From Middle English tipto, typto; equivalent to tip + toe. Compare fingertip.
1
To walk quietly with only the tips of the toes touching the ground.
We went tip-toeing along a path amongst the trees back towards the end of the widow's garden, stooping down so as the branches wouldn't scrape our heads.1884 December 10, Mark Twain [pseudonym; Samuel Langhorne Clemens], chapter II, in The Adventures of Huckleberry Finn: (Tom Sawyer’s Comrade) […], London: Chatto & Windus, […], →OCLC, page 8:
We tiptoed into the house, up the stairs and along the hall into the room where the Professor had been spending so much of his time.1913, Joseph C[rosby] Lincoln, chapter XIII, in Mr. Pratt’s Patients, New York, N.Y.; London: D[aniel] Appleton and Company, →OCLC:
2 more examples
Tiptoe through the window By the window, that is where I'll be Come tiptoe through the tulips with me Tiptoe from your pillow To the shadow of the willow tree And tiptoe through the tulips with me.1929, “Tiptoe Through the Tulips”, Al Dubin (lyrics), Joe Burke (music), performed by Nick Lucas:
Who can it be knocking at my door? Make no sound, tiptoe across the floor If he hears, he'll knock all day I'll be trapped and here I'll have to stay1981, Men at Work, “Who Can It Be Now?”, in Business as Usual: