My approach has evolved over time. Back in the prior century my standard procedure was to be upfront and clear about what I wanted which more often than not included role play.

The earliest exception to this was Mistress H. While she was delighted that I could take a full throttle thrashing with a belt she had some ideas of her own that she introduced into the sessions without asking my approval. She was also bossy and belittling. At first I found that erotic and was a frequent customer but eventually it grew annoying and I called it quits. It left me with a lingering unpleasant aftertaste. It was several years before I again did a session with a Domme.

When I finally resumed I still spelled out clearly what I wanted at the beginning. However as I noted in another thread I went through a phase where I played more from the Top than the bottom.
During that period I met Switch C who was a stripper at the time. She claim to have worked as a house Domme for half a year before becoming a stripper. At first we did spanking sessions in the club's champagne room though we also did a lot of lap dances. Eventually she agreed to do sessions at my place where we could do things we weren't permitted to do in the champagne room. We switched roles. Sometimes when she was at the club doing a lap dance we would discuss ideas and we were often on the same page. It was similar to phonesex except we were face to face and groin to groin. If she really liked the idea often a strange glassy eyed look would come over her face eventually and she would move very little for 2-3 minutes. I had deciphered this as being a "tell" for her having an orgasm.

My experience with C was in pivotal point in developing my interest in pleasing the kinky fantasies of the lady. This however was one of those Twilight Zone situations and one day she out of the blue informed me that she would no longer meet me outside the club and would soon stop working there as well.

A few years after that there was Mistress L a house Domme. I developed a very good chemistry with her despite the fact her spanking skills were only medium grade. With her the sessions became more and more about what she wanted to do.

She was very fond of strap on. One session she wanted to take me in an unusual position. However it involved me scrambling on top of some equipment in the medical room I refused because I thought there was too much risk on my falling and getting a fracture. It was uncomfortable having to refuse because I could she really wanted to do it.

Why did she want to do it?

Was it to impress me and earn my affection? Nope
Was it because she thought I might session more often and maybe tip a little more? I don't think that was it

The reason she wanted to do it

WAS

because she wanted to do it

And at the beginning of the very next session she announced that she had figured a safer alternative which she proceeded to do. One of the things about this position is it allowed her to move her face close to mine while she was pounding away. I could see lust in her eyes

There was an unusual form of CBT I devised when I was with Switch C. I suggested it to Mistress L and she LOVED it. Did it every session. More often than not she would invite any of the other Dommes not in session to come and watch. Now usually this adding other Dommes as an audience is done for the sake of the sub but in this case I really got the impression she meant this primarily as a treat for them not me.

Eventually she came up with what she thought was an enhancement to this technique. The first time she tried it things did not work out as she wanted. Indeed there was an unexpected result and the session ended early. That did not deter her and she devised what she was a clever workaround. This time she invited the audience very eager to share her kinky gratification with them. Once again the result was bad (and not in a good way) though not as bad as the prior time and the session did have to be cancelled. We talked a while afterwards and she said she felt guilty. I think she would've taken a few paddle swats at that point had I suggested that even though she normally didn't switch. But I didn't.

Afterwards I realized that she had devoted a lot of thought between sessions to this project during which she was wetter than the ocean.

My experience with C and L catalyzed a fascination with the kinky fantasies of women. Sometimes I do go into "Her fantasy is my fantasy" mode. On Mistress Ayn's forum in the thread about butt plugs I discussed one of those sessions.