It's funny. Without the Internet, and websites like this one (and WSG, Ignatzmice etc.) I would probably have never mongered.
Oh sure, I had a CBJ at my bachelor party (and the bitch from whom my best man hired the dancers tattled to my wife, but that's another story...), but I had never traveled specifically to get laid for payment.
My first time with a hooker was a disaster. I was nervous, overpaid, didn't know the game and almost quit the hobby right then and there. Here are few things I've learned by staying in the hobby and working out the difficulties.
Some of these tips are specific to Costa Rica, but most are applicable wherever you play for pay:
* You're not a porn star and never will be. If you're like most guys, you have some concerns about your sexual performance. Maybe you've been out of the game awhile and are just starting over. Maybe you have some ridiculous conception that your penis is somehow too small, or that you're unappealing to women.
Forget it! While it helps make sessions better to have some game with women (and a large penis can be an advantage), such game and skill is not strictly necessary. Keep in mind that these girls are skilled in making you feel like you're the only man. It's their job, not their social life. Also, you've got nobody to compare your sessions with but yourself. Relax. (The "relax" tip will be repeated here, just so you get it...)
* No, you don't have to f*ck them.

Seriously...sometimes it's fun to just have her do a private dance or toy show for you. Sometimes you just might want a nice relaxing massage and some conversation. There is no law that _requires_ you to perform any particular sex act with her. And again, there's no need to compare yourself to other guys. Each of us rolls his own way, and there is no single "right way" to enjoy P4P! If all you want is a BJ, fine. If all you want to do is snuggle and watch T.V., also fine. Never forget:
It's Your Money.
* Health risks. No extreme sport is 100% safe, and that includes sport f*cking. Yes, there are diseases and insects, but you can minimize your exposure to the nasties by practicing safer sex. Yes, that means using a condom, but it doesn't stop there. Educate yourself about safer sex before you travel. It will add to your peace of mind and make the sessions more fun.
* The "gross out" factor. Many guys are squeamish about rolling around on sheets that have been repeatedly stained by other dudes. Get over it. Frequent showers after the act will help ease your mind. Remember that you're traveling to a developing country; you'll see a roach now and then, encounter spooge-stains on the linens, etc. Again, get over it. If you keep yourself clean during your trip, all should be well.
* Crime. There can be no argument that violent crime is increasing in Costa Rica and probably other mongering destinations. There are ways to stay safer, including walking around only when accompanied by wingmen, taking taxis at night, "chica-proofing" your room by locking up/hiding your valuables before going out to hunt pu$$y, and staying sober enough to stay aware in your room and out on the streets. Don't tempt the good folk of Costa Rica by wearing jewelry or flashing cash. Try to blend in as much as a gringo can.
* Comportment. Sadly, many guys in this hobby are downright losers whose Mamas never taught them how to behave and how to treat others.

Remember, some of the places we play are in local residential neighborhoods, and loud drunken shouting, boorish behavior, aggressiveness and disregard for local customs will offend the folks who have to live and work in the places we play. Yeah, it's your vacation, but it's also mine. Don't Phuck it up for me, or we'll have problems.
* Drugs. Don't. I myself am a regular pot smoker, and I've partied hearty with the best. Problem is, C.R. is not the U.S., and if you get caught with drugs, you have a problem which *might* be solved with a small "tip" to the police...but which could just as easily land you in jail for a year. (The ticos call it "preventative detention."). Costa Rican law is essentially based on the Napoleonic code; you're presumed guilty unless you can prove yourself innocent. "Just Say No" is truer in C.R. than in your home town. Be careful. Even a joint can land you inserious trouble.
* Screw legal. Check the girl's I.D. ('sedula") very carefully if you have any doubts. Your hotel security or reception will also demand to see her I.D., but the responsibility for determining her legal age rests soeley upon your shoulders, not the hotel's. When in doubt...pass.
* Kink/gay/transvestite/orgy/swinger sex. If you're into that sort of thing, it's all there in San Jose. There are swingers' clubs (B.Y.O. chica), orgy clubs (B.Y.O. chica), gay discos/bars and dozens of hot trannies. However, be forewarned that many hotels do not allow T.V. guests. Be further forewarned that many guys on this forum are knee-jerk homophobes who will at best shun you and at worst, pick a fight to "re-educate" you. Be discreet.
* Research before travel. You'll feel more prepared to brave your first prostitution experience if you read, read and read some more here on CRT.
* Spanish. It's a good idea to at least have the basics: Numbers, directions, common greetings, sex words. If you need language help, many of us speak Spanish and are very willing to help you out (if you're not a dumbass or dickhead), so no worries.
* After the trip. You'll have so much fun that you'll be tempted to tell everyone you know about how great C.R. play-for-pay can be. Don't do it. Loose lips sink marriages, careers and social standing. Most of your friends will not understand, many will harshly judge you...and if you have a wife or GF, it could easily land you in a shitpool of trouble. Shut the f*ck up.
* Finally, and most importantly.... relax. You'll have a great time! But be forewarned again: One trip to C.R. and you may be hooked for life (pun intended). You might be embarking on your longest and most powerful addiction, so beware.
Any newbies with specific questions are welcome to send me a private message. If I don't know the answer, I'll point you to a resource which will get your question answered.
Pura vida! (Pure life!)