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Prostitution in Trinidad and Tobago is legal but related activities such as brothel keeping, soliciting and pimping are illegal. In Trinidad , Port of Spain is the main place of sex work,   including street prostitution on Roberts and Murray Streets. Some regularly commute between their home nation and Trinidad.
Prostitution in less common in Tobago , some prostitutes from Trinidad move to Tobago for the tourist season. The country is a sex tourism destination. Sex trafficking is a problem in the country,  as is child prostitution. Being a former British colony , much of the prostitution law mirrors that of the UK :. During the slave period, slaves could sometimes be hired as prostitutes. Prostitutes were required to be registered and have regular examinations for STIs.
In Port of Spain, a Sergeant Holder was given unlimited power to enforce the ordinance. He abused his position and, following an investigation brought about by a complaint, was dismissed from the force. The sugar slump of the s  brought many more women to the towns, turning to prostitution to try and make a living. During the Great Depression in the s, more women turned to prostitution. In his book, Calypso and Society , Gordon Rohlehr noted: "Some singers, indeed, presented the vocation of prostitution as the only alternative to that of housewifery, and warned young girls against leaving their mothers' homes.
The high percentage of promiscuity in the Colonies puts prostitution into the category of a luxury profession. When this profession is followed, it is usually for economic reasons and because the wages earned by the woman in her other occupation are often too low to obtain the necessities of life for her.
Prostitution was a boom industry in the s after the allied troops, especially American, were stationed on the islands during WW2 ,    especially around Port of Spain Arima. The spread of STIs was a problem in this era. The Governor of Trinidad and Tobago considered licencing the brothels in the country to ensure proper testing of the women, but this was never brought into force. Fox recalled that when he visited in , he was assured that every taxi driver could take him to a house of pleasure with any race of woman he desired.