The Shadow of the Torturer by Gene Wolfe

Winner of the BSFA award for Best Novel in 1981.
Winner of the World Fantasy award for best fantasy fiction novel in 1981.
Winner of the British Science Fiction Association Award for Novel in 1981.
Winner of the World Fantasy Award for Best Novel in 1981.
Winner of the T�htivaeltaja award in 2013.

Severian is a torturer, born to the guild and with an exceptionally promising career ahead of him . . . until he falls in love with one of his victims, a beautiful young noblewoman. Her excruciations are delayed for some months and, out of love, Severian helps her commit suicide and escape her fate. For a torturer, there is no more unforgivable act. In punishment he is exiled from the guild and his home city to the distant metropolis of Thrax with little more than Terminus Est, a fabled sword, to his name. Along the way he has to learn to survive in a wider world without the guild - a world in which he has already made both allies and enemies. And a strange gem is about to fall into his possession, which will only make his enemies pursue him with ever-more determination . . . Winner of the World Fantasy Award for best novel, 1981 Winner of the BSFA Award for best novel, 1982

This book is part of the "The Book of the New Sun" series.
Here are some other books from this series: