As we both got out of the shower and dried off, I was torn. I had just had what was easily the best sex of my life with the most beautiful girl that I had ever screwed. I knew that I wanted to get every moment out of this weekend. I also knew that I had never come three times in the same day. It was only about 8:00 PM, so there was plenty of time for another round before we went to bed.
"What do think about getting dressed up and going out for a night of dinner and clubbing?" I asked her.
"I don't think that's a very good idea. What if someone we know sees us together. I don't think there is a real good explanation for that."
I could tell that she didn't want to be seen with me. After I thought about it, it made sense. What beautiful woman wants to be seen with an average looking man on her arm? Everyone would just assume that either she was a hooker or a gold digger. But, it made me mad in a totally irrational way. I had just given this woman multiple orgasms, and I had nothing to be ashamed of in the sex department. If I wanted to go out and show off my "girlfriend for the weekend," then we were going out. "I'm hungry and I want to go out. Please get dressed in something that shows the world how hot you are. In fact, I would like to go with you to your closet to help you pick out an outfit."
"Something else I want to discuss. Are you on the pill?"
"Yes," she told me. "I have been on the pill for years to regulate my cycles. I can't get pregnant from you this weekend. So, feel free to come inside me. I don't have to swallow every time." She had made her point, and I was relived that I was in the clear having forgotten the condoms again.
We brushed our hair while it was still wet and then I followed her into her bedroom. I opened up her closet and began picking out outfits that were a combination of classy and slutty. She had several choices, but I settled on two that I wanted her to try on. The first was the classic little black dress. The second was a short tan leather skirt and tight white blouse combination that I thought would look amazing on her. I sat them both on the bed and asked which she thought she would look better in.
"I look great in both of those outfits. It really just depends on where we are going. If we are eating at a nice restaurant, the black dress would be more appropriate. If we are going to some trendy club, the other outfit would be more appropriate. Why don't you tell me where we are going, and that may help you make your decision."
She really was a smart girl. She had just told me the answer to my question, but had worded it in such a way as to still make it my decision. I chuckled and told her, "I think we could have a use for both outfits. Why don't you try on the little black dress and let me see what you look like in it."
She put the dress on without any bra or panties, then asked "Do you want me to wear only the dress? Or, do you want to see what I would normally wear with it?"
"Why don't you let me get a look at you with just the dress on? Please turn around so that I can see." She looked amazing in the dress, and as she turned, I could see the outline of her tits on the side of the sleeveless dress. "Please bend over like you are looking at the floor." When she bent over the short dress rode up her thighs, and I could almost see the start of her ass. "Why don't you put on a black push up bra and some thong panties," I suggested. "I would also like to see some nice heels with that outfit. Not five inch stilettos, but something more like this." I reached down and pulled out a nice pair of black pumps, with about a three inch heel. They would still make her look hot, but not like a hooker. She looked great with the bra and thong on.
"I also want you to try on the other outfit. Go ahead and take off the dress and put on the other one. Let's start with no bra and panties with this one." She did as told and I couldn't help but feel a stirring in my cock as she again was naked in front of me. She put the leather skirt on and it came about halfway down her thighs. Then, she put the tight white blouse on, and it showed just how amazing her tits were. I asked her, "Would you wear that blouse with no bra normally?"
"No. In the right light, it is basically see through. I wouldn't want to be quite that bold in public."
"OK, that settles it. I want you to wear the black dress to dinner with the black bra and thong panties. Then, you will change into the other outfit before we go to our next location." I liked being in charge.
Amy did as she was told and went into the bathroom to finish putting on her make up. I went back out to the car to get my stuff. I hadn't thought to bring it in before. I had a sport coat and slacks that would be an appropriate compliment to her black dress. I put them on and finished getting ready myself. As I looked at her in the mirror beside me, I knew that I would have no problem coming a third time tonight.
I knew of a fancy steak place that my bosses had taken me to in the area. As she finished getting ready, I made our reservation at Ruth's Chris. "Amy. I want to use some of the money you have stolen for our night out tonight. I can't use my credit card for obvious reasons. So, why don't you give me a few hundred dollars to make sure that I can pay for everything tonight?"
I could tell that this rubbed her the wrong way. She started to complain, and then she turned around and went into the bedroom. She came back out with four hundred and fifty dollars, handed it to me, and told me that was all she had in the house. I was going to bet that she was lying to me about the "all in the house comment," but we had enough money to go out on the town tonight. We could address that issue tomorrow.
I walked into the restaurant with her tucked into my arm and was instantly the envy of every man in the place. She looked so beautiful with the black dress on. The bra made her tits sit even higher than the implants, and I could tell that every man in there wanted to fuck her. I asked if they could give us a quiet table with some privacy.
We were directed to the bar to have a drink while they made our table ready. We sat down in an open table. On one side were four men apparently there for a business dinner. They were still wearing their suits from the day. The other side had a married couple in their mid forties. They appeared to be rich and the man tried to be casual as he kept looking at Amy.
One of the businessmen turned to me after we sat down and asked, "Excuse me. You look familiar to me. Do you happen to be a developer with properties in Florida?" I told him that I wasn't a developer. "Do you mind me asking what business you are in? You look awfully familiar. My name's Dave Roberts. I'm with the Ottoman Group. These are my associates. We are just celebrating the completion of a deal to acquire some hotels in Fairfax County."
I laughed. "Well congratulations Dave. My name's Edward. I don't suppose your desire to find out about me has anything to do with the fact that I am here with my girlfriend, the most beautiful person that you've ever seen. I'm not in the real estate business, and I don't believe that we have ever met. Has this approach ever worked for you before? Talk about how rich you are and hope that somebody's date or girlfriend decides that she has to have you. Has she ever dumped her date and gone home with you?"
The couple next to us had apparently heard the exchange and they both laughed out loud. Dave's friends were dumbstruck and didn't say a thing. I figured that they worked for him. Dave blushed deeply and said, "I'm sorry if I have offended you in some way. I really did think you looked like limited partner on deal we did in Florida last year." Then he got up and left. Before the situation got any more awkward, we were seated.
They honored my request and gave us seating in a corner booth that was next to three tables. After a few minutes, all of the tables were empty, and we had the area to ourselves. The restaurant was slightly dark, and I began to get ideas about what I could do in this fancy restaurant with this gorgeous girl. After the tables around us cleared, I put my hand on her leg, and moved it slowly up her thigh until I was massaging the area about two inches from her pussy. The waiter came by and delivered our food.
The food was fabulous. I cut up my steak several bites in advance so that I could eat with my right hand and explore Amy with my left. I moved her thong to the left, and began rubbing her pussy directly without the interference of underwear. Then, after her pussy got slick with the excitement, I put the tip of my finger up to the first knuckle inside her and began moving my finger up and down the length of her pussy. She made a little surprised sound, but let me continue. After a few minutes of this, I pulled my finger out to cut the rest of my steak. The waiter came back by, but he couldn't see anything. The table had a long cloth table cover, and it went all the way down to the floor. It hit me then that I could make her go under the table and no one would be able to see her.