She was wearing a very low-cut black mini dress. It accented her in all the right ways and I couldn't take my eyes off of her. She must have sensed that I was a bit overwhelmed and she smiled and said, "Well how do I look?" I told her she looked great and she thanked me. Trista sat down at the bar and ordered a merlot as the bartender gave me a second vodka/tonic; my first one had gone down pretty easily with how nervous I was. We talked about the game and baseball in general. I tried to impress her with the fact that I pitched in high school and I was impressed with her baseball knowledge as well. That didn't alleviate my nervousness however, as I was soon on my third drink as I continued to try to steal glances at her.
I was definitely tipsy, the vodka/tonics doing the trick, as we headed off to dinner. Trista was turning quite a few heads and I was very pleased to be dining with her. Over dinner, we got to know each other better, her controlling the conversation for the most part, asking all the usual questions. I was still trying to steal glances at her low cut dress, probably not doing a very good job due to the whiskey sours, having a couple of more over dinner too.
As we finished our dinner, Trista asked me if I wanted to join her to do some gambling. I suggested we go back to her room. She laughed and asked why we should do that. I told her that she looked very good and I would love to see her without that dress on. I suggested we make a bet and if she lost I'd get to see her without that dress. After some deliberation, we ended up deciding we were going to go to across the street to the casino and place one bet on roulette. The loser would have to do what the winner wanted for the remainder of the trip. I readily agreed.
By the time we got across the street to the casino, my mind was racing with all the things I was going to have her do. The main thing was first remove that dress and after that, it was going to be repeated acts of debauchery.
