(31M) Talking from experience here. I did it with an escort at 18 since I had (and still have) no clue how to seduce a woman. It was not exactly awkward, but it felt fake. Tbh though, first times are probably always weird. After that, because I was still having those raging hormones, I went to prostitutes about once every 2 months. Felt dirty and cheap afterwards every time. Until I got 28, that's when it just clicked that nothing was to gain anymore with prostitutes. Now I just don't do anything anymore. Thinking about sex leaves an empty hole inside and the fact that women (or social interaction altogether) are a hopeless riddle to me has led me to a life where sex has become non existent and masturbation has become purely a health thing to do to prevent cancer. If you would ask me if I'd redo my first time with a prostitute, I'd say not in a million years. Maybe it would've motivated me more to pay attention to actual woman who could have given a fuck about me. (Idk if that pun was intended, but it's there nonetheless.)

Don't get me wrong here either. I think prostitutes are invaluable (and honestly, many of them are respectable women). Society would definitely be a worse place without them. But I'd recommend not going there unless you're really out of options. And I'm pretty sure not everyone is like me, so at 20, you've still got a lot of potential. Just be more assertive and confident in yourself, put yourself out there, don't put the bar too high, don't meet women with sex as a goal but for who they are, etc etc (yeah, I've heard them all, and I hope that maybe they'll work for you at least.)