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If you have nice accent, potentially. Clubs, like in any other city, have a very specific customers. And I'm sure you'll see hookers there as well. As far as prostitutes are concerned, then prostitution isn't supported by the state, so there is no official site. Prostitution isn't illegal, but organised prostitution is. So good luck trying to find anything that even looks like legit and official.
Google is probably your friend here since your best options are probably individuals trying to promote themselves online. Since state doesn't support it, so organized crime will take the state's rightful spot and run it themselves.
So if you ask tourists where they get their information and where to get prostitutes, then taxi drivers tend to be the top leading culprits. But hey that is how it works for most cities that don't have state support for legal prostitution. You are bound to find someone there. Good luck. All other places are the usual: truck driver stops and so on. Old Town is probably filled with them too - the usual tourists spots, you know just like in any other city that has prostitutes trying to make a dime.
If you are less attractive, use google - put the right search terms in and you'll find plenty of legit sites with legit estonian or estonian-russian girls willing to do it for money. Some of them have introductions written in english for the sole reason of attracting tourists. Yeah, it's over here. They're mostly guys, not girls, though, but they're willing to do anything.
