It took some time to work out a plan, and I was very anxious about it. Lisa liked to have fun and could have a flirty side, but if this backfired, I could be in the doghouse for some time. I needed to see how she would react and if a blowup would end the journey to HotWife.
My plan was simple. I needed to get her in the proper outfit and let things play out. There is an area downtown with numerous outdoor restaurants and bars within walking distance of each other. On weekends, I have always included a low-key night out to relax after the week. It was not uncommon for us to go downtown, and it was normal for me to help pick her outfit whenever we went out. It was summertime, nice and hot outside, and I knew precisely the outfit for this test.
I showered and was getting dressed, waiting for the inevitable conversation. She walked in bra and panties, holding a skirt in one hand and a top in the other. My first thought was how to get her in panties a bit more on the skimpy side. She almost always wore thong-type panties, so that should be too hard. Most importantly, I needed to make sure she wore no bra. Her nipples were always somewhat perky and never flat, and she was self-conscious about it, so no bra was my more significant challenge.
"What do you think of this?" she asked, holding out the skirt and top. I hesitated, intentionally. And as expected, she asked, "Do you want to pick something else?"
"Sure, let me go look," I responded as I walked toward her closet. Pretending to look around for a few seconds, I pulled out the dress I had in mind. I felt a pulse between my legs, just picturing her bending over in it. The dress, made of that super light cotton material, had a sage green background covered with numerous flowers and fern leaves. It was a halter top dress that I knew would push her boobs together with thin straps that would tie behind her neck. Its waist had an elastic band to hold the dress tightly around her middle. The skirt was short, well above the knee, or should I say barely enough to cover her ass when she stood up straight.
She looked at me and said, "That is for the beach, not here. I can't even wear a bra with that."
"Oh, come on," I said. "It looks super cute, and you don't need a bra. We will sit outside, and it's a warm night." She rolled her eyes and headed for the shower, dropping her bra and panties in the hamper. I took the opportunity to pick her most sheer set of white dental floss thongs, nothing but a sheer tiny triangle to cover her pussy, I could find, and laid them out with her dress.
"I will be in the kitchen, but there's no rush," I said as I walked through the bathroom. A short time later, she came strolling in, wearing the dress I had picked and her hair pulled up in a rooster tail.
"Nice pick on the panties," she said with a smirk. "I decided to put my hair up, so I didn't have to wash it."
I opened the car door and took a quick peek as she slid into the seat. She was wearing the panties I had chosen. Their form fitted perfectly, giving me an excellent outline of her pussy. Although I knew it was still to clear see, it was bare and smooth. My excitement for the night was growing.
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Dinner was casual. We sat at a table outside, nice and warm. We both ordered something light, and I suggested frozen margaritas, something nice and cool in the heat. I was hoping to start lowering Lisa's inhibitions early. Margaritas always had a way of doing the trick. She was self-conscious and almost constantly sliding her hands under her butt to keep her dress down or tugging at the halter top to make sure her boobs were not showing too much. Our server, a cute little brunette, was very flattering and seemed to take quite a liking to Lisa. It seemed to help lower her guard, and I considered the attention a stroke of luck. After Margarita Number Two, she grew more comfortable and less worried about what her dress was doing. It was perfect, though, as the halter was not doing a good job of keeping things in, and several times, I noticed parts of her areola beginning to peek out. Our cute server seemed to enjoy it as well, paying us lots of attention and flashing knowing smiles my way every time she stopped to "check on us."
We finally settled the check and started walking back to our car. I waited to set the next trap until we were about 50 yards from my planned stop. "Hey, let's stop in for a game of pool," I said as we approached the billiards bar. "Bet I can beat you," I said, knowing her competitive nature might not be able to resist. We hardly ever played, so I thought she would assume a fair matchup.
"Oh, you think so," she said, "well, we shall see. You're on!"
It is what I call a classy billiards bar: awesome tables, a beautiful bar, and luxurious seating. There was plenty of room between tables, and, lucky again, the table very near the center of the room was open. I pounced on it. One of the very sexy servers asked for our drink order, and I opted for another round of margaritas, this time asking for double tequila. Lisa's inhibitions should have been well lowered by the time she finished her drink.
