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Its literal translation is "jockey" but the word jinitera goes much deeper than that. Sure, there are those that'll say that a jinitera is nothing more than a prostitute but I beg to differ. You should know that prostitution is technically illegal in Cuba and great efforts have been made to get hardened prostitutes off the streets.
You will routinely see police checking girls' 'carnets' Cuban ID's to see if they have any record of prostitution. Three year jail sentences are not unheard of. Also, if you sleep with a Cuban less than 18 years of age, you can be looking at a hefty jail sentence yourself. The legal age of consent in Cuba is years old but that is only for activity between Cubanos, not Cubanos and tourists.
See our Crime in Cuba section for more information. H omosexuality is becoming more and more tolerated and transvestites can be seen lining the sidewalks of La Quinta and the Malecon. Better look out for those Adam's Apples! Oddly enough, lesbianism "tortilleras" is not very prevalent among Cubanas. Jinitera o can refer to any Cuban female that accompanies a tourist in the hopes of either being taken out to places they can otherwise never afford, for a small gift the next day or better yet, an offer of marriage.
Mind you, this works both ways. Foreign women with young, handsome Cuban men arm in arm are routinely spotted. Even more enticing to them can be the hope of meeting a tourist and being "whisked away" to another country.
P lease don't confuse a hardened professional prostitute yes, there are some of those too with a jinitera. Prostitutes can be found all over the world, in any city, in any small town check your local paper for "massage" places.