What was your best sexual experience ever and why? What was your worst sexual experience ever and why? What was the last thing that you masturbated to?
In preparation for play I will tell a boy that I will expect answers to these questions in person.
My negotitation style comes from conducting technical job interviews. Many of the skills translate.
There's a big difference between asking open-ended questions and specific questions. Tops prefer asking open-ended questions. Bottoms prefer answering specific questions. And I tend to use a mixture of the two.
It's not really these specific events that I am interested in. Making these questions about particular events makes them easier to answer.
Much of what I'm looking for is watching the body language of the boy when he answers these questions.
I'm really looking for the bottom to talk about a great sexual experience. When a boy talks about a great sexual experience their body language is a bit similar to the body language that they might show in pleasure later.
The worst sexual experience can go a couple different ways, all useful. The worst sexual experience question will often get people to talk about limits that they hadn't really thought to mention. Sometimes it's about specific acts. Boys will sometimes talk about instances of betrayed trust. And these are emotional landmines that must be avoided in the scene later.
The masturbation question provides an opportunity to talk about the pornography that they enjoy. Or memories or fantasies. This often gets closer to the truth about fetishes than asking outright. I'm not going to be able to recreate one of these fantasies, but improvising on one of the themes raised can be really effective.
I believe that these questions really help me make the experience better for the bottom, and so makes the experience better for me.