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. In fact I was even in a relationship with one and I am 100% sure she was doing it fully voluntarily and even liked the work (we sometimes spoke about doing something else and she wasn’t too interested).

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.

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. It’s less forced than a normal brothel where the girls just come 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. If she makes you feel comfortable you will have a better time. 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 a poly one) so they know me and I know them.

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.

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.