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?"