Jacquelyn Wren is the daughter of a courtesan and the Chatelaine of Dragon's Caern, a woman without a real role in society but who feels responsibility towards the five young girls, daughters of the now-dead Baron of Dragon's Caern. When she's informed that a new man is coming to take over Dragon's Caern and to turn out all the people who currently live there, she agrees (rather improbably) to kill him. However, when Jacquelyn meets Captain Gabriel Drake on the road, she discovers that he is the son of the former Baron, a man whom people thought dead who has been living as a pirate for many years. Gabriel has been pardoned by the Keeper of the King's Privy Seal and wants to return home.

Gabriel understands that he needs to marry a rich woman because Dragon's Caern is almost penniless. However, as he is trained in polite behavior by Jacquelyn, his thoughts turn to her. Is there any way that he can avoid having to marry a fish-faced gentry woman and to have Jacquelyn? Can he keep himself from being hanged as a former pirate? And what about the rumored treasure at Dragon's Caern?

The first half of this book is pretty poor - weak plot, unlikely characterization in places, and a 'romance' that feels very unromantic. About halfway through, though, Pleasuring the Pirate hits its stride with subplots and machinations, as well as the introduction of interesting new characters such as Jacquelyn's mother. Most of the characters in this story are horribly stereotyped - the pirate's first mate who's always drunk, the evil land-grabbing baron, the hellion young girls, etc. etc. - but it's definitely a better read once the halfway point is reached. Too little originality and far too many improbabilities in the plot mar the narrative, but by the end it feels more like a romance and is a reasonable read.