OF COURSE ITS AWKWARD WHEN YOU START!
Ever since you were old enough to know your name you have been taught not to get naked for strangers. Ever since you were old enough to know what sex was you have been taught that the only girls who do it for money are dirty, drug addicted, less than human types, or ruthless golddiggers. Ever since you were an adolescent, you have been taught that "paying for it" is proof of your lack of worth as a man. When faced with a cute girl with a hot bod, who may be "out of your league" by conventional standards, you will feel self conscious!!
Hell, I have been in the "hobby" for well over a decade. I still feel a little awkward, especially with a new girl.
BUT!!!!! Be reassured. You are getting naked for a stranger in a mutually agreed upon arrangement. If you chose well (wwhich is easy to do with some research on terb) you stand a very good chance at meeting with a great girl with a head on her shoulders, who is smart and practical about the biz. As for "paying for it" just look at the news. Some of the most desireable, eligible, and manly guys have paid for it. It is more a matter of convenience, and an ability to differentiate a need for sexual satisfaction from a relastionship - the two are related, but not the same. As for the girl being out of your league, and maybe looking at you with less than a lusty stare - keep in mind that there have been tons of guys far more disgusting than you, and also keep in mind that escorts, WAYYYYYYY more than your average civilian hottie at a bar, appreciate a kind, gentle guy, WAYYYY more than they appreciate six pack abs, tans, and big biceps.
Think of it like jumping off the high diving board at the pool when you were a kid. Sure it is bloody scary - awkward, and you have never done it. But odds are in your favour - you will be fine, and tons have done it before you and survived just fine.