In the early 90's all my sessions involved role play. By far the most common scenario is that the Domme would play my boss and she was receiving complaints from some of the women at the firm that I was sexually harassing them. She tells me that because I am otherwise a good employee she is not going to fire me if I take a very severe physical punishment.

In a variation of this the Domme would play a double role. We would start where she played one of the employees and I would harass her then switch to playing the supervisor (in one instance a quick apparel change was done with the hair altered a little to highlight the character change)

Then on one occasion it was a double Domme session. Younger Domme played the victim whom I would harass at the start. She would then accuse me in front of Older Domme who played the boss. Younger Domme got to witness my punishment and expressed vindication. I have found a majority of double Domme sessions to be not worth the extra cost but this one worked out nicely.

Later when I was doing a lot of switching there was a scene where where the Switch and I pretended to be two people who hated each other. They had a deal that they would play strip blackjack and the winner gets to torture the loser. If one player jumps to a clear lead they would start telling the other about the terrible things they were going to do (exaggerating somewhat but we did agree in advance that the loser's punishment would be a little bit nastier than usual to add some spice)

Several years later with a Domme who did not switch we acted out a variation of this where we played chess. I would set up the pieces so I had a small advantage at first and teased her about what was going to happen to her and she would squirm a little but then I would make a blunder and she would gain the upper hand and begin telling me what she was going to do to me (with a bit of exaggeration) And then she did checkmate me with a big grin.

A few years ago a certain Domme was involved in a fund raising effort for her favorite charity. The Role Play was that I would make what she regarded as a ridiculously small contribution. I refused to increase my contribution. She then persuaded me to do the right thing. At that time I was a bit obsessed with punishment enemas. The deal we worked out was that she would start by torturing me with an enema. If she could force me to capitulate with the enema I would write a check for a certain amount. If the enema didn't work then she would torture in other ways but the amount of the contribution would be less.

I was thoroughly restrained and a double Bardex nozzle was inserted and inflated. I held out for as long as I could but gave in eventually. She stopped the flow but at first only released one hand so I could write the check while still in agony and only when it was signed allowed to get relief.

There were a few others that were not very unusual (e.g. college student caught cheating)