My Second Date With Tom

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.


My ‘Milk Money’ Moment

Have you ever seen the movie ‘Milk Money’?  It’s this really cheesy 90’s film where these young boys want to see a naked woman for the first time, so they pay a prostitute.  One of the boys thinks this woman would be a perfect match for his single dad, so he befriends her.  His dad falls for her and it’s a romance from there to the end.  It has always been one of my favorite movies.

I had my own ‘Milk Money’ moment today.  I was on camera and I got pulled into an exclusive room.  At first, the client just wanted to chat.  Then he began to subtly suggest we find a way to chat offsite.  This is directly in violation of my contract with my company.  If we solicit experiences off the site, we will be immediately terminated.  I was curious though, I had been enjoying talking to him and, like I said, he was being subtle.  So we made arrangements for me to meet him on Skype.

Once we were there, he offered me $80 for an hour of my time for what he referred to as a “date”.  How could I refuse?  That’s twice what I make modeling and I was actually having a nice time.  So I started my camera.  He kept his camera and mic off and typed me all of his dialog.  He is a dom in the BDSM community and wants a sub that he can learn and have new experiences with.  This is perfect for me, because that is what I enjoy sexually in my personal life.

Tonight we just talked and learned a little bit more about each other.  We stayed up talking for almost two hours.  He offered me compensation for my extra time, but I declined because I thought his original offer was incredibly generous and I didn’t mind staying on longer.  By the end we both agreed that we had a really nice time and we wanted another “date”.  So we made arrangements to meet this Wednesday around midnight.

I like to think of this experience like a “patron” from the Renaissance.  A man who pays an artist for her work and for her company.  I feel badly taking his money, because I did genuinely enjoy myself, and it didn’t feel like work at all.  At the same time, I can’t afford to take a night off from modeling for dating.  I’m hoping we can find a balance that works for both of us.  I’m going to call him “Tom” in my head, after the dad from ‘Milk Money’.