There are a lot of things that could be said in trying to answer this. So, is there anything in particular you would want to know about in relation to piracy and prostitution?
I will say this, the "Black Sails" presentation of it is highly glorified. This is from my season 1 review of the historical aspects of the show:

This is a show on the STARZ channel. Female nudity and lesbianism is somewhat expected from this channel for this kind of show. It has to be remembered that the most significant reason for their portrayal in Black Sails is to draw and please the male audience (especially the highly desired 18-30 male demographic). Practically all the prostitutes here are portrayed with nice clean skin, no scars or blemishes, and amazing figures. They are closer to looking like modern fashion models than eighteenth century prostitutes. So far, none of these women have signs that they suffered diseases typical of the day (for example, scars from surviving small pox would not be unusual). It would be surprising if physical signs of venereal diseases did not appear among these women. It should be noted, there are still many episodes for these problems to show up in. Diseases aside, none of the women appear to be average looking or below, which is surprising considering that back in the day (and today for that matter) prostitution came in all sorts of appearances, shapes, and conditions. These women are idealized versions of prostitutes so they can appeal to the audience, and are not historically correct by any means. Branching off from this topic, the other main actors of the films seem too well groomed as well. Extremely white teeth on a pirate would have appeared quite exceptional for this period (and for the greater world population for that matter), along with neat and clean body waxing. All of this is typical of Hollywood pirate films and shows.