A selection of letters written by beat writer Jack Kerouac (1922-1969) while at college will be offered at Skinner in Boston on November 16.
Estimates range from $2,000-5,000 each, the Guardian reports.
The majority date to 1940-1941 when he was in his late teens and were written to George J Apostolos, a friend from his hometown of Lowell, Massachusetts.
Kerouac writes of a friend's sister: "There is no doubt in my mind that you or I have never laid our eyes on such an exquisite creature as Jacqueline Sheresky.
"Her neck has that stamp of blueblood; it curves up delicately and like ivory to a perfectly moulded almond chin, and thence to quivering scarlet lips, covering a row of alabaster teeth.
"Her eyes are dark as ebony, with a flash of fire in them. Her hair topples down in rippling cascades of black sleekness, over a pair of resilient, lush shoulders. She is slim, blooming and graceful; I have never seen anything like it."
Skinner told the Guardian: "In these letters Kerouac comes through as playful and brilliant, an eager student who seems perfectly at home first in the unfamiliar prep school culture at HM, and later as a freshman at Columbia.
"One is also reminded that this is private correspondence exchanged between two teenaged boys in the late 1930s and the early 40s. Kerouac refers to old high school adventures, his homesick love of Lowell, and describes his social exploits, drinking, partying and explorations with girlfriends..."
Last year a first edition copy of On the Road made £22,500 ($33,972) at Sotheby's London.
We have an exciting selection of books and manuscripts available.
Please sign up to our free newsletter to receive exciting news about books and manuscripts auctions.