As we had scheduled, tonight was my second date with Tom. We spent a lot of time at the beginning discussing logistics. We are caught in the middle of two difficult situations. The first is that he doesn’t have infinite money to spend on my time. The second is that I can’t afford to spend time with him for free. So I suggested a flat rate per date. That way he can budget accordingly and I can allocate as much time as I can afford.
I still feel weird taking his money. I enjoy his company and the experience is as much fun for me as it is for him. I have never been in this kind of situation, so maybe I just need time to adjust. He has done this before and he says he is comfortable with the arrangement.
After we got the business aspect out of the way, we chatted for a little while. Mostly about our perspectives on the BDSM community and the kinds of things we’re into. We also set up the rules for our own BDSM arrangement. It was all very exciting. The only thing that kind of threw me was that he said he didn’t think he would ever be comfortable meeting me in person. I hadn’t though of it in any real way, but to me it was an exciting proposition. Maybe I misjudged when I made my comparison to “Tom” from ‘Milk Money’.
I did strip for him near the end of our date. It was nearly five hours of camera time before he asked me to take my clothes off. If I think about it in terms of hours, that is probably the longest date I have ever had before I ended up naked. It’s an interesting thought.