Caller of the Week for September 16

My caller of the week for this week is "Jim" who likes to be humiliated.
Jim is not content with having me call him names, or pretending to dress him up in slut’s clothing, or tell him he’s got a tiny dick. Nope. He wants the real thing. He likes to go out in the world and put himself in situations that will cause him humiliation, and of course, sexual tension.
How do I pull this one off? Well Jim has discovered an adult bookstore/boutique that sells sex toys and feminine clothing. The first week we did a session about this, I called the store and spoke to Svetlana, who is Slavic, and doesn’t seem to understand much English. But she did understand enough to let Jim come in the boutique and try on a teddy, hose, and heels, which he then bought. But according to Jim she’s very hot. In fact, when he called afterwards, we used Svetlana in a fantasy.
The next week I spoke to Kim, who is American, and understood English very well. Not only did I ask her to make Jim try on a teddy, this one much more revealing than the first, but also she had to look at him after he was dressed in a teddy, hose, and heels. Once again he called me and was very excited when he got home.
This next week, I will probably get Svetlana again when I call, as she is due to work the day he goes up there. From his descriptions of the clothes there, I’ve picked out a mostly sheer bodystocking I want him to try on, of course with heels. And of course Svetlana will have to look at him with it on. Then we’ll have to see just how excited this little episode will get him.