Friday afternoon, I had a pitch in the New Jersey suburbs. When the meeting finished, I hopped in my car service home. It would be nice to get home earlier than a normal workday after many late nights at work that week.

Smiles and I made plans to spent the night together. Since I finished early, I took the opportunity to call Smiles and ask him to come over. He wasn’t busy, so he began to get ready and make his way to Hoboken.

When I got back, I wanted to do a few things. I wanted to make a quick run to the grocery store to grab some food to make for dinner, but I also wanted to get a haircut. I was in desperate need of one. I didn’t have time to do both, so I decided to choose the haircut.

I hopped on the motorcycle and hit up my usual spot to get my ears lowered. Of course, I had less time than I originally expected. He began calling the second I sat in the chair. I texted him and asked him to hang out at Starbucks until I could make it down to meet him.

All the while he was waiting for me at Starbucks, I was getting the worst haircut of my life. She completely removed my sideburns. I was not a happy camper, but there was nothing I could do about it.

I quickly paid, hopped on the motorcycle, and made my way down to meet Smiles. He was sitting in a comfortable chair sipping his coffee when I arrived. I hung out for a few minutes while he finished because it doesn’t exactly work out well taking a coffee on the back of the motorcycle. While we waited, I pointed out my new botched haircut. He didn’t sugar-coat it for me, and he told me what he thought.

When he finished, we hopped on the bike and went to my apartment. We walked in to find my roommate finally cleaning up his mess in the kitchen. We left him to his work, and we sat and watched TV until we decided what to do with our Friday evening. I introduced Smiles to my new favorite show, An American Horror Story. I was curious how he’d feel about it because he used to be a television producer.

I posed him a decision about food for the evening. I told him I no longer had the energy to cook dinner, so we could grab takeout/delivery, or we could go out for dinner. He suggested we go out for a nice dinner since he’d never really gone out in Hoboken much. I made a few suggestions and showed him them online. We decided on Dino & Harry’s, a great steakhouse I’d actually gone to with N when we were dating. We took a casual stroll up there around 7:30. I knew there would be a long wait since it was such a popular weekend dinner spot. When we arrived, Smiles spoke to the hostess and got an estimated wait for a table. It was 45 min. to an hour. We decided to check out a few other options. We weren’t thrilled with the other options, so we decided to head back to grab a drink at the bar while we waited.

We ordered the calamari appetizer and adult beverages while we talked. Before long, and after a little sweet-talking on Smiles’ part, we were offered a table. I could see in Smiles’ eyes, he was already feeling his drink. It was cute to see his tolerance in juxtaposition to my own high tolerance. I wasn’t turned off at all by it. In fact, I was enjoying it because he was being more playful than usual.

Throughout dinner we had great conversation. I was very happy. It was a very nice night together, and it was nice to be on my home turf for the first time in a while. We shared dessert and had our fill. This was one of the nights on the high end of the spectrum that seemed to make up for the nights on the lower end.

We paid our tab and made our way back to my apartment. The temperature dropped pretty drastically, so we walked as briskly as one can after consuming big steaks and desert.

When we got home, we hopped into my bed and cuddled while we talked for a while. I can’t remember what we talked about, but the conversation was very relaxed and casual. I finally felt he was comfortable with me and was opening up. This led to me removing his shirt and rolling him onto his stomach. I loved pleasing him, so I massaged his shoulders and back.

I wasn’t really in the mood for sex that night. We both had a fair amount to drink and it was a long day for me. I wasn’t going to push the sex issue since I wasn’t into it myself. I would attempt to jump his bones in the morning, the time I am usually at my horniest.

Instead, we both got ready for bed and dozed off. Tomorrow was a new day. Who knew what it would bring?…