A combination of memoir and polemic, the book explores Brown's decision to give up on romantic love and to take up the life of a "john" by frequenting sex workers.

He takes up frequenting sex workers, and comes to advocate prostitution as superior to the "possessive monogamy" of traditional male–female relations, which he debates with his friends throughout the book.

[1] After then-girlfriend Sook-Yin Lee breaks up with him in 1996, Brown, who lacks the social skills to pick up women,[2] spends a celibate three years mulling over what he sees as the negative aspects of romantic love in the modern world.

[10] In the final chapter, "Back to Monogamy", he ends up with one particular sex worker, "Denise" (albeit in a strictly financial way) for seven years as of the book's publication.

[12][a] The book comes with a 50-page text section, including a bibliography,[13] footnotes and an appendix in 23 parts that argues for a system in which "paying for sex is preferable to romance-based methods".

[14] It includes some commentary by his friend and fellow cartoonist Seth, who disagrees with Brown's position and accuses him of having no emotions, but then goes on to say, "The funny thing about Chester is that out of all the men I know he’s quite possibly the one I think would make the most considerate boyfriend or husband for a woman...and yet he is the one who picked the whoring.

[18] Brown takes the position throughout the book and its lengthy appendix that prostitution should be decriminalized, and as a libertarian insists the sex trade should not be regulated by the government.

The book was on the verge of completion when Ontario judge Susan Himel struck down several prostitution-related laws in September 2010, which was to be appealed by the government of Canada in June 2011.

In a scene in which he debates sex workers' health care with Seth, his outrage surfaces not in his face, but in a thought balloon in which a thunderstorm rages and takes over the panel.

[31] Brown moved his drawing away from the overt Harold Gray influence (as seen in Louis Riel and Underwater) towards a style inspired by the "very stylized, stiff look" of Fletcher Hanks.

[33][b] Brown cites the "austerity" of the films of Robert Bresson, who "instructed his actors not to show any emotion on their faces",[34] as a major influence.

He had considered that angle, but in the end decided that he wanted to make it clear that he had a personal stake in the issue based on his own experiences as a john.

[35] New York Times critic Dwight Garner compared Brown's pro-prostitution position to that of political philosopher Martha Nussbaum.

[39] That he had been working on a graphic novel on the subject had been known in comics circles at least since 2004 when, in an interview with The Pulse, he says he explores some of René Girard's theories of the origin of desire in his then-yet-unnamed book,[40] and its appearance was much anticipated.

"Out of consideration for the women, Brown doesn’t provide any background detail on the prostitutes he visits, although he does note that he spent a lot of time talking to them and learned much about their lives.

"The advocacy displayed in the voluminous pages of the appendix may have been a detriment to the work overall, according to Tom Spurgeon at The Comics Reporter; "Give me scenes like the one where Brown argues with Seth over the issues, seething and impatient with Seth's answers and his own, desperate and human in wanting to make and win such discussions, over any number of facile dissections of each argument's actual merits.

[50] Obscuring the faces of the sex workers could be seen as Brown objectifying them, and with a feeling the book lacks a female perspective, "especially since all we see of them is their frequently naked bodies.

[40] Following poor sales of the Louis Riel comic-book serialization,[16] Oliveros relented and gave Brown the go-ahead to publish Paying for It directly in book form.

[59] Following the success of Louis Riel, Drawn & Quarterly anticipated high sales, printing nearly 20,000 copies of the first, hardcover edition of the book,[60] for its May 3, 2011 release.

[61] The introduction was by famous underground cartoonist Robert Crumb, and the book includes quotes from Brown's peers such as Alan Moore and Neil Gaiman, as well as from writer and former call-girl Tracy Quan, sex columnist Sasha, and a number of academics.