second date

The second date with Gregory.

My original plan was to leave work early and have a nap before I showered and got ready. I was recovering from a bad cold and thought it would help. It was supposed to be a relaxing late afternoon.

Work had other ideas. I managed to get home early, but was still sitting in my kitchen on my laptop at 5:45 pm. I’m managing a huge issue on a deal and it’s taking up almost all of my time.

Suddenly I realized I had only 45 minutes before I was supposed to leave to meet Gregory. Yikes!

I managed to get it all together just a few minutes late. I knew I wanted to wear a dress because I was keen to wear stockings. I’m more fond of garters but they show beneath many fabrics, and I always try to avoid having my underthings visible. So I wore beautiful black stay ups with a wide lace band.

I wore an amazing pink and black striped demi bra from Agent Provocateur and black lace panties from Hanky Panky. I was irritated because the fabric of my dress was silky and I could see the pattern of the lace underneath. I couldn’t wear a full slip because my dress had a low-ish square neckline. I tried a half slip with lace but that showed too. So I added a smooth and boring half slip that at least hid the pattern, and figured I’d take it off at some point.

I arrived five minutes after I was supposed to. I met him at the private club to which he belongs. There was no sign on the door so I stood in the lobby like a dope, not knowing where to go, until he came to get me. He greeted me with a hug and a kiss and helped me off with my coat. He commented I was more dressed up than I needed to be but looked lovely. I told him there was no way I wasn’t wearing a dress.

He showed me around the club and introduced me to a few people. I liked his openness and self-deprecating humor. He told me how much it cost per month (it wasn’t much) and said it allowed him to look like a “big swinging dick” with his clients.

I wondered inwardly how many dates he’d been on there. He was pretty smooth.

We went back to our table and chatted a bit with a young woman who works there whose father knew Gregory from school. He’d brought her a bottle of wine to give to her Dad. She mentioned she was no longer with her boyfriend which led to a humorous conversation about dating, in which she said (among other things) she’d never have sex with a guy on a second date. I roared inside given I was pretty sure that was going to happen with Gregory and me.

When we were finally alone we toasted each other. He put his hand on my leg and on my side – he’s very tactile – and I liked the affection. We sat on the corners of a table so one knee was touching.

Like before, we covered all kinds of topics. I tried to better understand what his dating life was like. He mentioned one woman he’d dated but who was way too clingy. He didn’t specify how clingy, unfortunately, since I think its always good to define one’s terms. He also didn’t give me any sense of how many women he was dating or having sex with. I wasn’t about to ask for more details. Didn’t need or care to know.

Honestly, it could be that he could be like me, with others I’m dating and a few men in my stable, or there could be nobody else. There was no conclusion to be drawn by anything he said or didn’t say.

I made a comment that once I met someone I really connected with, the others tended to fall away. He didn’t particularly acknowledge the comment, ask about it, or reply in kind. Of course, I was worried after the fact that I shouldn’t have said anything. At times I’m prone to oversharing when I’m trying to get information but don’t want to ask directly. After all, it was only our second date and I didn’t want to give him the wrong impression.

We ordered a cheese and charcuterie platter to go along with the wine. When we were almost done the bottle he said: “so we are done the first bottle, did you want to get out of here?”

I was surprised he didn’t order dinner for us. The platter was fine, but it wasn’t overly filling.

“Where would we go?”

I told him I had to leave to pick Liam up the next morning so while I wasn’t being presumptuous, my place would give us more time to spend together.

We settled on my place.

But before we left I had to go say hello to three people I noticed who I knew. They all happened to work for my ex-husband Will in his prior job and I knew them well. One was one of his close friends. I popped over to say hello.

They asked if I was the member and I said: “no, that would be my date.” The close friend of Will’s joked that he could check out Gregory’s wine collection to vet him for me (there is wine storage at this club). I called Gregory over and introduced him. I made the joke offer, we all talked about wine, and before I knew it the men were off showing each other their wine lockers.

I liked that Gregory was comfortable, and I hoped he liked that I introduced him. It’s important to me to be with someone who I can take to all kinds of different events and meet different people. Gregory had “gregarious” on his list of things he was looking for, so I hoped saw me that way as well.

The men came back and I got the report that Gregory passed the test. As we left, Gregory commented how much Will’s friend knew about wine (he’s a true oenophile) and mentioned he gave him a bottle of wine. I liked that he did.

He helped me on with my coat and we walked to the lobby to wait for the Uber he ordered. He put his arm around my waist and we kissed. It was really nice. When the car arrived he went to open the door to let me in and I scooted across to the other side. He saw me do it and re-opened the door, telling me I didn’t have to do it. Seemed I was on a date with a real gentleman. He told me even in the last years of his marriage, he still opened the car door for his ex-wife.

As much as he was a gentleman, I was hoping to see the other side of Gregory when we got back to my place.

What do you think?