Good idea! I think it will help you feel more relaxed about it.

There isn't really an ethical issue if you pick her well. I usually go for independent girls (the ones not working in a brothel). In fact I was even in a relationship with a sex worker and I am 100% sure she and her friends were doing it fully voluntarily and even liked the work (we sometimes spoke about doing something else and she wasn't too interested). We often talked about her work and it was kinda cool, sometimes a friend of hers had a client and we'd have to sneak outside so he wouldn't see us. And then we'd be cuddling on the couch hearing them go at it.

Of course there are some forced girls but this is mainly in the more dodgy brothels. I mean really you will know when you set foot in there. You will feel it immediately. Just walk away. I have had to do this once or twice in my life. In one case I had already chosen a girl but I could see it in her eyes so I just paid up and left. But really, this is with the more dodgy places only.

What I could recommend is going to a "Sauna club". It's a German phenomenon where you just go into a sauna kinda place wearing one of those towel coats, and you can eat there and relax in the pool and there's a whole load of working girls around. You can chat with them and pick one you like. Then you pay her and you go to a room in the place. It's less forced than a normal brothel where the girls just come in a line and shake your hand and you have to decide immediately. The good thing about having more time is that you can also mention it's your first time and see how she reacts. Buy her a drink first (yes they will be expensive because you're also paying for some of her time). If she makes you feel comfortable you will have a better time. If not just don't go with her and let another one approach you. In these places they come to you. I have had some of my best times in those places. Also, don't forget you can 'pull out' (pun intended) any time. You don't even have to go the whole way the first time if you're not comfortable. Just go as far as you feel good. You still have to pay the full amount of course. But I'm guessing money is not really the problem.

Another thing I do a lot is to pick girls that work from home independently. Where I live there are some forums where the girls are active too and you can just tell by the way they respond and the reviews from other customers, which are nice. I tend to go to regular girls while I'm not in a relationship (or when I'm in an open one, though rarely) so they know me and I know them. Three of them also became friends in real life and one became my girlfriend for a while.

But anyway, one thing I want to stress to you: I felt also awkward about doing this the first time. But now I regret not doing it earlier. Life is too short not to enjoy it. Sex is fun. I don't care about how "my first time" came to pass, it doesn't matter at all. Most people's first times are in fact not too great, usually a haze of drink and stumbling around. But of course these things are super personal and sex is a loaded subject. Don't ever force yourself. If it doesn't feel right there is always another time.

I felt bad the first time because of the stigma around prostitution but seeing how some other guys get 'hookups' I don't feel so bad now. In some ways this is fairer. You don't have to tell a girl she is the only one in the world, feed her drinks, trying to coax her into going with you. It's just a fair and square agreement between two people. Some guys really lie to girls and don't care about them at all. I used to look up to them but now I'm glad I'm not like that.

Anyway if I can give you more advice let me know. I was also a late virgin. And even though I did this I am still having a hard time chatting up girls. It will probably not solve all your problems but it will make you feel much less 'left out'. At least it did for me.

PS: Sorry for the long story but I kinda wish someone had given me that talk back in the day so I just wanted to help.