Hey mongerloid2
I didn't consider myself sexually experienced either (and still don't) which is why I took up punting in the first place. I considered it like training because no one wants to be inexperienced in bed, plus the money you spend taking someone out on a nice date or multiple nice dates isn't guaranteed to lead to action and I bet it'll cost about the same if not more than what it costs for a punting session. At least you know that the WL is likely to be experienced and show you a good time (assuming you didn't pick a dud).
Anyway, I also treated it as a way to learn to become relaxed when you need to do the deed, and whilst I'm still learning this, maybe I can share some other things I learnt about punting. Note all of the following points tie into each other so try and make the connections where I'm, not explicit since it can be hard to connect ideas when typing stuff out.
1. Don't consume alcohol and punt (or caffeine).
Whiskey dick is a thing and as a result the computer ain't computing.
Also, alcohol and decision-making doesn't mix. On a number occasions, I've decided to book a session whilst under the influence with the train of thought in my head being, "Should I? Eh fuck it why not ay?" I tend to find these last-minute bookings result in me not being able to finish, whether it be due to whiskey dick or just anxiety.
Also, avoid caffeine. Don't make the anxiety worse.
2. Deciding whether to punt book a punt or not.
I've learnt that if I have doubts about whether to book a session or not then I shouldn't, that's it. The sessions where I spent some time trying to decide if I should or not resulted in anxiety kicking in at some point either before or during the session (e.g. having second thoughts on the way there, will the WL meet expectations, what time do I have to leave to get there on time, how long into this session are we, or anxiety about finishing too quickly (see the next paragraph)). I learned that for me punting basically needed to be the first thought that came into my head when I woke up because that's how I know I'm feeling pretty damn horny. I haven't had a bad session where there was no hesitation in booking whatsoever. The downside of this is that I might not be able to book the S-tier (top looks AND top service) WL because of the people who booked as soon as the roster came out (I'll get back to this in dot point 3).
But if I'm THAT horny then honestly, a 6/10 is probably going to be feel enjoyable. (LINK)
Additionally, you won't be anxious about finishing quickly if wake up horny as fuck because all you'll care about is finishing and you'll be lost in the moment trying to do so. Isn't that what you're paying for really?
3. The WL you pick.
I recommend starting off by seeing someone who has a lot of experience under their belt and is rated highly for their service and not necessarily their looks. They'll make you feel more comfortable when you start off. And then see them a few more times, as you'll already have an idea of what you're getting yourself into and there's the bonus of rapport. Both will definitely reduce the anxiety. You'll figure out what you like with experience which will reduce your anxiety too. For some appearance might be the be-all and end-all of whether you get off. For others decent-looking might be enough if the service is top-notch. Just focus on being in the moment for the timebeing when you're punting.
4. Managing expectations.
You've probably seen a bunch of the ARs on here where people rave about a particular WL which results in you having high expectations about the looks or service. The reality is that YMMV or beauty is in the eye of the beholder. I don't think there's anyone who is 10/10 in looks AND service. That's a unicorn. What isn't a unicorn is 10/10 service with say 7/10 looks. Try not to go in having preconceived notions. What's the best way to avoid this? Book when you're horny as fuck as I mentioned previously as you'll be lost in the moment trying to finish.
I hope this helps mate