Transgressions is a novel in the form of a diary of a young man from Woodstock, Vermont, who is sent to Trinity College, Cambridge, in the early 1930s. He studies languages, history and art, travels in Europe and settles in London. During the Second World War he writes political and current events commentaries. The book contains explicit descriptions of sexual acts and fine and decorative art objects.

Some characters in the book have the names of real people, such as Guy Burgess and Bernard Berenson. Others are similar to, or parallel to them. There are also greyhounds and wild cattle.

The settings, in addition to Woodstock and Cambridge, include Florence, Venice, New York, London and Northumberland.

The title refers to both political and sexual transgressions.