An Overnight Date with Dan

The last time Dan took me out was on a Monday night and while we both had a great time, we had to cut things short since it was a “school night.” Thus, Dan was keen to schedule our next date on a Saturday. We ultimately ended up planning to meet up on the Friday after Thanksgiving, since it served the same purpose in that we didn’t have to wake up early the next day.

I texted Dan a week before our date and noted that I was looking forward to seeing him and wondered if there was a specific plan yet. He asked if a traditional dinner date would be acceptable and I readily agreed since I didn’t have any other ideas at the time.

We arranged to meet at a restaurant called Manhattan Cricket Club that had been recommended to me by a friend. Dan arrived a few minutes ahead of me and scoped out the process of getting upstairs. Thus, we enjoyed a lovely dinner downstairs, replete with oysters and fun cocktails, before we were whisked away to a dark room at the top of the stairs.

Since we have been friends forever, our conversations ran the gamut, but eventually we decided to leave the club and head to Dan’s apartment. We sat on his couch and talked for a long while, interspersed with kisses. After a discussion about fancy lingerie, Dan wanted to see what I was wearing underneath my dress, so I slowly lifted my dress up and off. Not long after, Dan grabbed my hand and led me to the bedroom.

Knowing that there was potential for an overnight date, I had told Viktor that intercourse was on the table if I was feeling it, but I didn’t share this fact with Dan; I simply waited to see what would happen.

Once in the bedroom, there was a lot of kissing and fondling of increasing intensity. I was having a fun time, but I was still very much in my head. Over the next hour or so, I felt myself vacillating towards and away from lust, but was unsure why.

As things progressed, Dan went down on me, which felt nice, but I never fully surrendered to orgasm. I think after the buildup of reminiscing about our having been together 25 years ago, along with the very flirtatious fun we had been having, I expected more from the experience. Fireworks? I don’t know.

Afterward, Dan invited me to stay over and I accepted his invitation. But, soon after, I was a little sorry I had agreed to stay over and wanted my own bed. I didn’t regret anything I had done with Dan, but, by then, I was done and really didn’t want to continue kissing, cuddling, etc. Plus, no matter how much I like you, I can not sleep in some one’s arms – I toss and turn an average of 20-30 times each night. Trust me, it isn’t happening. So, I kept trying to gently roll out of his arms and onto one side of the bed, which proved more difficult than you might imagine. It felt somewhat awkward and I wondered what Dan was feeling and thinking. Did he want or expect more? We really never discussed our expectations or intentions ahead of time.

I eventually fell asleep, but woke up the next morning at 7:30, which was not surprising since I usually get up between 7:30 and 8:00 AM. I managed to stay in bed until 8:00, but then I had to get up. I couldn’t continue to lie there awake. I knew that Dan relished sleeping in until late, so I quietly slipped out of bed, grabbed my clothing and left the bedroom.

I then brushed my teeth, washed my face and dressed. As I was sitting on his couch, I texted Viktor and recalled that he was leaving at 9:30. I felt badly about slinking out of Dan’s apartment, but didn’t want to simply wait around for hours until he woke up, so I rushed back in time to spend a few minutes with Viktor before he left. Yes, I suppose I could have read my Kindle for several hours, but once I was up, I was ready for breakfast, or at least coffee. And I certainly didn’t know my way around Dan’s kitchen.