Do you think I should book an escort with a friend or go alone? The thing is I'm very shy which is why I'm preparing so much for a casual night out. If I call my friend I'll be acting out even more awkwardly but I also wouldn't know what to do alone so can someone guide me. Is it a good idea to bring people you're already friends with or should we befriend people at these escort sites and get to know more people? The last time I went to a dating club and not a nightclub, but it was a disaster so this time I'm really keen on using someone as a support.  

Don’t be shy, it’s as normal as meeting a new person. I’m sure you don’t want to make the night a more awkward one as you already mentioned so it’s better to go with the flow and eventually you learn to explore and get hang of it. 

I can help you with this. Ping me!

Just because one experience was a disaster doesn’t mean things will never turn out your way. Give it a second chance, this is exactly how you’ll learn.I remember my first time, so much recollection but well, at first you’ll seem to be nervous but to get rid of that maybe gulping down a few shots of vodka would make you more confident, and just take the lead and your escort will follow.

I once told my escort that it was my first time and she kind enough to talk it out with me and teach me the pace for my next encounters, turned out to be a pretty good experience for me.

I would actually want my best friend with me but if things get kinky, not sure whether I’ll feel more comfortable and I definitely wouldn’t want to waste the night instead of enjoying it so I guess, I’d recommend you to go alone in case things might heat up.

It all depends on your level of comfort with your best friend, how close are you guys and what kind of a bond you share. If you feel you won’t enjoy while him being around and are unaware of how things function then just google a few searches and trust me you’ll be good to go for the night. Honey, there is a first time to everything so you can’t just be dependent on your friend, go alone and enjoy it, it will be a new experience for you and eventually you’ll learn on your own. Just go with your instincts.

Maybe have a discussion with a few people, ask your friends for some tips as a newbie. Go talk to people at the escort forums if that makes you feel good and gives you a clear picture. It’s always good to have an idea and this way you might even get a few more creative ideas by talking to different people.Don’t go for something that will make you uncomfortable, leaves no point in having the night out with your escort then, you’ll be quite awkward and conscious instead of enjoying or having a good time.

You won't improve if you keep relying on other poeple. I do believe that you should just go alone, yes there is a tendency that its gonna be awkward because you don't know what to do and probably really anxious but learn to control yourself and act confidently. You can also tell the escort about your feelings and I am very sure that she will be more tha glad to help you and will adjust with you. 

@Jade is right. Just go and ask for some tips from people and creating a scenario in oyur head. I also agree with @jessiejay that you need to go alone so that you'll build up confidence in doing it. 

You should not be shy. There are escorts that will guide you if you tell them that it is your first time. You only have to be confident for you not to ruin the night.

With a friend would be more fun. you know, if she asks you for a threesome then your friend would enjoy.

I see most usernames is already red here. I really wonder what it means. 

You better bring four friend so that you will not get bored.