I had known James since high school. He really wasn't all that freaky but he did like to have fun. James was a big fan of strip clubs and loved, like most of us, naked women. I told her that he frequented them so often, he was often asked to provide security for "special guest" at the club he went to most often. She didn't say much about it but seemed intrigued.
I had invited James over for dinner a few weeks after she met him. After a great meal, James said his favorite part of dinner was always the dessert. Danielle responded that we didn't really have anything sweet but if we wanted to run to the store and pick something up, she would be more than happy to bake it for us. With that, we headed to James' truck.
Before getting in the truck, I told James that I needed to go grab my wallet. I went inside and told Danielle that she should change into something super sexy. She said she wasn't sure if it was a good idea and didn't want to make it awkward for James. I told her that the guy goes to a strip club about 8 nights a week, he likes scantily clad women. She said she would think about it.
At the store, James and I decided on Lemon Bars, always a good choice. When we got back to the condo, I noticed that I could see Danielle changing through our bedroom window. Danielle and I made it a point to leave our blinds open so that people could see in if they wanted to. You had to be a little taller to see over our fence which usually meant only taller men got a peek. I pointed it out to James and we sat on the tailgate of his truck for about 15 minutes, watching her try on one piece of underwear after another. My favorite was when she put on a cute white g-string and a "wife beater" tank top. Once she had that on, I told him we should head in.
We intentionally made a noisy entrance so she would know that we were there. I had hoped we caught her attention before she changed out of the preferred outfit. Upon hearing us she said she would be right out. We waited, anxiously.
When Danielle came out, she was wearing...the same jeans and a t-shirt as when we left. I gave her a confused look and we went about our evening. After dessert and some conversation I walked James out to his truck. "I'm not sure what happened" I said. He wasn't overly concerned and said that he was heading to the club and could see boobies there.
I went back inside and she immediately apologized. I told her there was no reason to be sorry. I told her that I was a bit surprised, considering her comfort level in the pool She said that she didn't mind showing off, she had just never done it in front of somebody in close quarters. Again, I assured her not to worry about it. What she said next surprised me. She said "I want to do it, I'm just unsure of what to wear and how he will react." My first response was that she should wear something she feels good about and that she thinks she looks good in. I assured her that he would enjoy whatever she wore. I told her about us watching her trying outfits on. She didn't believe me until I mentioned a couple of the outfits that she tried on.