Chapter 3: Dinner With Jack

Wednesday night came quickly and I drove myself to the restaurant. During the day I had debated a while over what to wear and in the end went for the “girl- next-door” look more so than the “slut” image he was probably expecting (hoping?) for. I decided that I wanted to hear what he had to say before I gave him anything more than what he’d already seen at the party. Hopefully he remembered me from the last few minutes of the party when I finally took off my bra leaving my boobs exposed along with my bare ass while my pussy was barely concealed by a flimsy G-string. Granted, they only got to see me like that for a few brief minutes but I would be willing to bet that good ‘ol Jack had masturbated that night at home imagining me going even further - a LOT further.

I loved going home after parties and try to picture how many men were jerking off at that moment because of what I’d showed them or maybe even done to them at the party. Now that I’d seen Jack’s family, it made me even hotter to think about their loving father and husband, stroking himself in the bathroom behind a locked door as he closed his eyes and imagined how it would feel to have me suck his dick and then even fuck me.

Mmmmmmm, the thought of his cum shooting out onto his hand while he dreamed of cumming inside of me was SO hot!

As I stepped into the restaurant, I was surprised to see there was a waiting list. Fortunately, I was a little late so Jack must have already been seated as I didn’t see him in the waiting area. I took off my jacket and I could almost feel the eyes of the men seated around me boring into me. It wasn’t that I was wearing anything that particularly revealing, just pants and a t-shirt, but rather how it was how they fit me that caught their eyes. The t-shirt was pure white with glittery letters spelling out “Daddy’s Girl” across the front. Being it was about two sizes too small for me, it clung to me like Saran-Wrap leaving little doubt that it was ALL I was wearing above the waist. It was opaque enough that my nipples didn’t show through but being as tight as it was, they poked out even when I WASN’T cold. It was too short to reach my pants and even when I pulled it down there was about an inch of my tummy left showing.

In the process of pulling off my jacket, it pulled up and now there were two to three inches showing which I didn’t bother to do anything about. My light tan pants were just as tight and seamless, fitting my ass like an expensive glove. Even the so-called “no-show” panties would have revealed themselves had I chosen to wear any - which I hadn’t.

Around my waist I was wearing a studded leather belt my mom’s best friend from Oregon had sent me for Christmas, more for show than anything as there was no way those pants were coming down even without it. The pant legs came down to the tops of my ankles, revealing my strap-on, three-inch high-heels. A simple gold necklace around my neck, a Pandora bracelet, watch, and diamond earrings were all the jewelry I was wearing.

My vain attempts to curl my hair enough to keep it from being completely straight had met with only with moderate success. At least it didn’t look like I’d just gone swimming and dried it out with the car window open. As I approached the snobbish-looking high-school girl who was taking names, I felt a bit of satisfaction in seeing her glaring at me with barely disguised contempt. She was pretty good looking but still had that high-school image about her. I knew that when we were standing together, the guys were looking at me and not her, even though her skirt was about as high as her manager would have dared to allow anyone to wear. There were times I wouldn’t mind being sixteen again but sometimes, being a little more sophisticated with just a touch of slutty was all a girl could ask for in situations like this.

I gave the little bitch Jack’s name and she noted from her list that he had already been seated so she took me to his table. She didn’t stay an extra second and promptly turned her back on me and strutted away. Jack looked just as he had in his photo which was a relief. It wouldn’t have shocked me to see someone totally different or perhaps thirty pounds heavier with half the hair. I’m not a big fan of on-line dating but I’ve heard enough horror stories from friends that do to not have to have worried a little bit about who I would actually be meeting.

“Hi, I’m Kelly,” I introduced myself.

Jack, ever the older gentlemen, stood up and pulled out my chair while introducing himself to me. His eyes gave me the once-over, well, make that two or three times over, and I couldn’t help but notice they lingered on my bosom each time. What was interesting to me was that unlike most men, he made no attempt to hide what he was doing, almost like he WANTED me to see him basically undressing me with his eyes. Well, it’s not like he hadn’t already seen 99% of me before so there shouldn’t have been much to leave to his imagination.

A waiter appeared promptly to take our drink orders. Jack waited for me and when I just ordered my usual Diet Coke, he took the same direction and ordered one for himself. While we waited for our soft drinks, we traded some small talk about the changing weather, the unexpected crowd this evening, and other minutia.

The waiter was quick and within a couple minutes had our drinks. Jack probably had plenty of time waiting for me to have perused the menu and I ate here enough to know what I wanted so we made our meal orders with Jack making sure the waiter understood it would all be on his check.

“Well thank-you for dinner this evening, Jack,” I said as the waiter departed.

“Trust me, it’s worth every penny to get to spend the time sitting across from you,” he said with a smile, “Damn, you look hot.”

I just smiled and shrugged, as if to say he was just being nice.

“Don’t give me that,” he chuckled, “You know damn well every guy in the joint was staring at you when you walked in ... just like you had all of us eating out of your hands at the party.”

It was the first mention by him of the party, or for anything related to it or his intentions for that matter so I took him up on it.

“So I take it you liked the party?”

Jack rolled his eyes and smiled at me, “Nahhhhh, overall the party sucked ... just bunch of drunk guys and porn movies ... but YOU dancing, now THAT was the only good thing all night.”

“So why didn’t you ask me to do more?”

Jack took a deep breath, his cheeks puffed out and he released it slowly, giving himself time to formulate his response. “Trust me babe, it wasn’t for any lack of DESIRE. I just know the wife would have killed me if she ever found out and with THAT bunch, she would’ve for sure.”

I studied the straw in my drink like it was a cryptic manuscript, waiting for him to make the next move. The silence was a bit awkward for a moment until he finally started to unveil why we REALLY were here this evening.

“OK, so I guess you want to know why I asked you to have dinner with me?”

I looked up from my fizzing drink and raised my eyebrows, signally he was 100% correct.

“Well ... I just wanted to see if you were interested in ... well let’s just say I was wondering if you do more private parties?”

“MORE private?” I replied coyly, “As in ‘just you’ private?”

“Well ... yeah.”

“And just what KIND of party are you looking for Jack?”

Jack hesitated for a moment and then looked around, as if to make sure nobody was listening to our conversation. At least he didn’t have to worry about me being wired - there was no hiding so much as a pea under THIS outfit without it showing through.

“Before I say anything more about that, I wanted to tell you that when I saw you at the party, the first thing I thought was how much you look my daughter Jenny.”

Now I’d seen his Jenny in the portrait photo he had sent me and frankly, I didn’t see the resemblance but it was a nice line so I let it pass. I couldn’t help but poke him a little just for fun though.