Whenever I knew that I'd be attending a work-related conference in a city other than where I lived, there were two things that I'd typically check into as soon as it was definite: what were the must-see local landmarks and who did I know who lived there or nearby. With an upcoming conference in Washington, D.C., since I had visited there during several vacations and had already done the tourist thing a few times, my focus was on reaching out to somebody specific from my past who I knew lived nearby. Erin and I had dated in high school and had sporadically been in touch over the ensuing years, primarily through social media. She'd been a good Irish Catholic girl back then so our physical relationship had never progressed past second base though she had quite obviously been wrestling with her desires versus her upbringing at the time. As the years had gone by, though, she had lamented to me a few times that she knew the guilt had caused her to miss out.
Whenever I tried to assuage her regret by assuring her that, because of my inexperience back then, she hadn't really missed out on anything she would typically suggest that, now that we're both experienced, it was too bad that we didn't live closer together. There had even been a few times when she'd suggested certain fantasies that she'd been concocting about us, though without really going into detail. Given that she'd gotten married almost immediately after graduating from college, and that she'd dated her husband for most of their college years, it didn't surprise me that she was romanticizing having an affair. If she'd gotten over her Catholic guilt and married life was feeling a bit stagnant, there was nothing wrong with a bit of fantasizing but, as time went by, I was feeling more and more like she would jump at a chance to jump my bones.
Knowing that she lived somewhere near DC, I figured if I presented her with an opportunity, she could decide if she was serious about going through with a hook up. Once my trip was booked and there was little chance that my plans would change, I reached out and asked her whether she lived anywhere near the hotel where I'd be staying.
"It's a pretty short drive, depending on traffic," she replied, "Why? Are you there?"
"Not at the moment, but I will be," I said, "so I wanted to plant a seed about potentially getting together for coffee or drinks or dinner, whatever you prefer."
"Are those my only options?" she asked.
"Did you have something else in mind?" I asked, answering her question with a question but also making sure that she was the one making any suggestions that might lead to us finally consummating our relationship.
"Assuming that you're not sharing your hotel room," she replied, "I'd be interested in checking out the view and the bed and how you look naked."
I was definitely surprised, not only that she hadn't deferred, but that she'd immediately taken it to the next level. It was probably good that this conversation was taking place via instant messages rather than in person because I'm sure the surprise would have clearly shown on my face. While I shared more detail about my trip, I was also starting to think about the potential for this encounter. When we'd dated, Erin had been slim with small boobs, long black hair, green eyes and fair skin. I wasn't sure about her boobs but I figured it was a safe assumption that she still had green eyes and fair skin. I knew for a fact, however, that her hair was now short and gray, which made me wonder if her bush was also gray but, the more we discussed this visit, the more confident I was becoming that I'd be finding out.
Out of the days that I'd be in town, it turned out that the evening of my arrival worked out the best for her because her husband was going to be out of town that night. Her two boys were old enough to look after themselves for a few hours but she wouldn't be able to stay overnight and it would likely be too risky for her to try to visit me again once her husband was back, though she wasn't ruling it out completely. We didn't talk about details or specifics, both of us presumably good just going with the flow and seeing how that played out. On the day I was traveling, we stayed in touch so that I could keep her up to date with my progress. We'd decided against having her just meet me there in case anything changed or was delayed but she was ready to go once I let her know that I'd arrived.
I had enough time to check in and get unpacked but, once she let me know that she was in the parking garage, I went down to the lobby to meet her. Thinking about it as I was riding down in the elevator, I couldn't believe that we were finally here and it was happening. I was never completely confident that she wouldn't back out but things were looking extremely good at that point. When I spotted her in the lobby, it was looking even better and so was she. She was wearing a sundress that showed she was a little more curvy than she had been as a teen but her boobs didn't look too much bigger. I was eager to get her out of that sundress to see what was underneath but first we hugged there in the lobby.
"Are you sure you want to do this?" she asked, but not because she was having second thoughts; she just seemed to want to confirm that I was still into it.
"How did you feel as we were hugging?" I asked, once again answering her question with a question.