Lil’ Kim is somewhat of a space cadet like those twenty-one year old college students who party and spend their parent’s money. And once she was through with that she wanted to spend sugar daddy's money.

After the initial exchange of pleasantries, Lil’ Kim became very quiet and there was dead silence in the cab on the way to restaurant. She did not utter a word to the point where I thought that either I smelled bad or maybe she thought I was too old or too ugly.

We decided to sit at the bar per my suggestion. It would have been too awkward to sit with someone who was obviously not my daughter in the middle of this fancy restaurant surrounded by adults and middle-aged people. Quite a visible age difference, almost 20 years! Also, I figured if we sat at the bar next to each other it would give us a chance to be a bit more cozy.

Still silent, I commented on what a nice checkered blouse she was wearing and she liked that. Lil’ Kim began to open up and grew increasingly comfortable as she downed various alcoholic drinks one after the other. She started with a glass of white wine progressed to a Black Russian and then on to Grey Goose Vodka with tonic and ice. She just kept drinking as if she had a wooden leg.

She seemed quite insecure of herself as she kept asking, “Do you think I’m pretty?' or 'Do I have fat arms?” She must have asked me that several times and the answer was always 'No baby, you’re great!'

Our dinners arrived and she ate as fast as she drank even helping herself to my french fries. After dinner she said that she wanted to go to Vegas and party with some friends and that's were I came in.

“I love older men,” she said, “and I want you.”
“What are you going to do to me?”
“What are you going to do to me?” she countered.
“I'll think of something really good, promise.”

At the bar we noticed a slim attractive woman in her late thirties with short blond hair - just how I like them - having a light dinner by herself and constantly checking her Blackberry. We surmised that she had been stood up and decided to stay by herself but after a while it didn't seem that way because she just lingered after her meal and read a book. We figured she was a regular and it surprised us to find an attractive lady all alone in the middle of a crowded restaurant. I wished she was with me, great looks and good age group.

But instead there I was with Lil' Kim who proceeded to say, “David, people who look like us would never be alone.” A very interesting and immodest comment. After the umpteenth drink and given the fact that it was a workday, I told Kimmie I had to head home unless she wanted to spend some quality time elsewhere if not, “I understand. Sniff, sniff.” She tried to console me by saying, “No, its...its okay. I am game” and with that we took a taxi to my favorite hotel.

Her skin was so smooth and firm; it was really obvious that she was very young. In bed she was totally wild, she just kept going. That was her trademark: eat fast, drink fast, fuck fast with no end in sight. She kept saying to me “eat me out” or “fuck me from behind” or “let me come on top” that I lost track after a while.

She hurt me, physically. Will need to take my vitamins after this one. On my way home on the Metro North I texted her.

“You fucked my brains out”
“I did”
And moments later, “You liked it ;)”

*Addendum: What gift did I give her? She asked me to pay for her trip to Vegas. She mentioned an amount and she got it in cash.

Tuesday, 2010 May 18
Lil’ Kim texted me today wanting to meet again but I told her I was busy. Will I see her again? Maybe, we shall see.

My last few encounters have been fun and interesting but they seem meaningless. Do I really look for meaning (with SBs, for crying out loud) or just another notch on the bedpost? Meanings are quite a rarity in this business.

Been toying around with the idea of hosting a little SD/SB party. Small size, discreet for about 10 people at a nice place in midtown with a few select SB's. Just to see which SDs will drop by and pay for everything - always thinking of things as trades, hilarious. My stockbroker is (still) single and loaded so maybe I will hand him the bill as I usually do for our dinners together.