I find that you need to see a provider a few times to so you can feel them out to see if they are open to something like that.  Also, it usually takes a few appointments before they feel comfortable enough to be submissive with you.

Looking to experiment with hair pulling and choking.... Is there a provider in Chicago that likes this?

Thanks for the advice so far guys

It would depend on what you are looking for as a "submissive".  Many use that term rather loosely.

Many gals will be "submissive" if you just ask her in the emails/texts prior to an appointment.  As this is not a sex act, it would not necessarily "put her off".  And you will find out quickly if she has any real interest in playing as a sub.

It shouldn't depend on a return session, as she won't know you any better than on the first visit.  Especially if you just had a GFE session, but on the second trip are now expecting her to be submissive to you (and again, it depends on what you are actually seeking).

In the OP's example, the hair pulling is a benign activity (unless he is looking to "scalp" her...which I didn't get that impression).  However, choking a gal may set many off (and with good reason..that can and is a dangerous activity if someone has no clue in the potential risks involved).  And it may not matter how many times he sees her...it may just NEVER happen (outside of a seasoned Pro Domme/sub experience).

WOOF!  Safety is paramount but a little kink goes right to my CUNT!