Remember, each date is an independent event with lots of variables ... to complicate things ... both independent and dependent variables are involved. Shit! you might need Baye's Theorem to get this right, here it is:
Bayes' theorem. Let A1, A2, ... , An be a set of mutually exclusive events that together form the sample space S. Let B be any event from the same sample space, such that P(B) > 0. Then,  

P( Ak | B ) =   P( Ak ∩ B )
P( A1 ∩ B ) + P( A2 ∩ B ) + . . . + P( An ∩ B )

Note: Invoking the fact that P( Ak ∩ B ) = P( Ak )P( B | Ak ), Baye's theorem can also be expressed as  

P( Ak | B ) =   P( Ak ) P( B | Ak )
P( A1 ) P( B | A1 ) + P( A2 ) P( B | A2 ) + . . . + P( An ) P( B | An )
 

If the john was decent and the session was cool, maybe. There is familiarity and comfort. However some guys think the more they see a hooker the more she will do...some of us already do, on the first date, what we will do period.

But yes, I do have expectations of the second date being better. I know I will be.

On one hand, I have found that second and subsequent sessions can often be better than the first one if and when you have built rapport and mutual comfort and gotten to know each other well during the first session. I have also found that good providers generally appreciate the repeat business and may thus provide better service (and sometimes an expansion of their menu) in the hopes of developing a new regular client.

On the other hand, I have also found that second and subsequent sessions can be worse than the first one. Sometimes it is because the experience loses its novelty or just becomes stale, so the spark dies, as can occur in any other sexual relationship. I have also encountered providers that I believe became complacent on second or subsequent visits and made less of an effort because they believed that they had already won me over as a regular.  

So I think that the answer to your question depends on what you enjoyed about the first session and how that specific aspect of the experience might improve or decline in subsequent sessions.

I always think so. There's only been 2 providers that I've had 2nd dates with and I thought they wen't a lot better than the 1st. I'm more relaxed and the provider knows a little bit more about my likes and dislikes

There have been extenuating circumstances when the 2nd date didn't work out, but for the most part seconds are way better. It goes without saying that, usually, there is no 2nd date if the 1st isn't stellar.  

Sometimes you can run into trouble on the 10th, 20th, or 30th date if one, or both start taking each other for granted. Of course, one can never really know for sure about 1st dates, 2nd dates, nor 3rd dates. The only true axiom is that no matter what, all hobby relationships will eventually come to an end.

...the first date is usually a learning experience... The second I can really relax and enjoy...

if the guy is more of a player like you, then first date is as good as it gets...the excitement of fresh meat...nothing better than that for a guy who is a serial hobbyist...lol..this type of guy usually has never been married or divorced and has a lot of disposable income usually or has a hot young wife (usually his 2nd or 3rd wife) but still need thrill of a new body. Usually over 30 reviews on TER lol

there are guys whom it takes some time to warm up to the new person to be fully open up sexually...they need an emotional connection to be able to get off better...for them second date is definitely better than the first...tend to be guys over 50 , usually married to the same person for many years and just want something stable on the side because wife is no longer feeling sexual...they turn into regulars