Posts Tagged feminine

Late Night Rendezvous

I nailed down plans to meet Connecticut Cutie after work that Tuesday night. He told me he’d be in my neighborhood, so it would work out well.

He ended up running late from dinner with friends, so I stayed in the office and did a little blogging until he was ready. When I go the call that he was on the corner, I went down to meet him.

My favorite date spot in the city lately has been The Breslin, so I suggested we go there. It’s a short walk from my office, and we had great flirtatious conversation on the walk there. He joked about going to a psychologist for mother issues, and I made more than a few Oedipal comments in jest. I told him I don’t go to a therapist nor need one because I have free therapy sessions all the time. I use my friends for that service. I’m sure they all just love to hear all about my problems and issues, but hell. What are friends for?

We also talked about our days at work. I had a very easy day involving a lot of personal work with just a little professional work.

When we got to The Breslin, it was very crowded. I couldn’t believe how many people were there on a Tuesday night. We had a hard time finding a seat, so he ordered drinks at the bar while I tried to hold some ground in the corner. I was standing next to some of the most obnoxious men I’d ever met. You could tell they were a real “boys’ club” type, making lewd comments. I knew it was only a matter of time before I heard the f@ggot term thrown out. I decided to move away from the group before they p*ssed me off more.

I ordered my usual dark and stormy, and he followed my lead. He’d never had it before, and I told him it was a good winter drink. He tasted it, and was happy with his selection.

FInally a table opened up, so we jumped on it. Space was limited, so we sat with our legs intertwined. This was good body language once again and made it easy for a little leg touching. Our conversation was going very well. We were both telling stories and laughing a lot. I told him about how much I get into Halloween and started showing him pictures from Facebook. He was shocked because he never got into the holiday. It was always something haphazard and last-minute for him.

Throughout the course of the night, there was a lot of leg touching. It was nice because we could flirt in this way without making a spectacle of ourselves. The only people who had a view of this were the bartenders, and I didn’t care if they noticed. It was mutual. As much as I was rubbing his legs, he was rubbing mine.

When he needed to use the facilities, I told him how to get there. I joked about the long journey he’d have to make through the basement of the hotel. He looked at me like I was insane. I equated it to backlot Disney. When he returned, he detailed his journey through the underground labyrinth he encountered. He detailed the myriad of characters he passed on his journey and joked about how strenuous it was. I liked his sense of humor. It was all something I would say. We were meshing well.

However, I was still having a hard time getting past the flamboyance. I had a feeling he was holding back some as well. I liked the guy quite a bit, but I also wanted a real man, not a man who acted in a feminine manner. The distance thing was still in the back of my mind. The vetting process was far from over. I’d have to continue to see where things went and evaluate if it was worth the extra effort.

I hadn’t eaten any dinner, so I ordered some fries from the bar. We joked about working out and my being fat as of late. I know I’m far from fat, but there is a certain level that is fat for me. I don’t like it, and it makes me want to eat better and work out more.

After three dark and stormies, when I brought it to his attention, he realized he needed to make his way to the train. If he missed it, he’d have to wait another hour for the next. I told him I’d walk him half way — Basically back to my office. He needed to stop at the bank along the way, but we also really needed to hustle. When we got to my office, I told him I’d walk him one more avenue before heading home. When we got to Fifth Avenue, we embraced on the corner. We started kissing, and this quickly turned into a bit of a makeout session. He was a great kisser, so I didn’t mind one bit. I was starting to worry he’d miss his train. We’d already joked about how his parents extended his curfew for the evening. I knew they’d be royally p*ssed if he made them pick him up at midnight.

It was comical as we both acknowledged the other’s hardon as we pulled back. We were both really enjoying each other’s company. I said goodbye, and he sped off to Grand Central Station.

I made my way home, and made it a point to text him and tell him how much I enjoyed myself that evening. I learned he did in fact make the train and would get home at a decent hour. He responded, and I could tell he was really into me. I needed to make a decision fast, or I would risk really hurting him. But, I still wasn’t sure. I had a lot to think about. I would be traveling to Chicago for work, so this would allow me time apart and time to think about what I really want.

We talked about possibly getting together over the weekend, possibly in Hoboken. I knew once that happened, things were going to escalate fast. I already knew he had a great body from his revealing pictures on a4a. I knew he had a healthy sex drive, so that wouldn’t be an issue. I just needed to decide if the flamboyance thing was something I could get over — Something I could either look past or fully embrace. It wasn’t my style, but after all, I was constantly expanding my horizons…

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Human Resources Part II

This is a follow-up post to the earlier “Round 2” post…

HR and I were finally able to set a time to go on a second date.

This time, we agreed to go to Industry, a popular gay club in Hell’s Kitchen, after work. I had never been before, but this was happy hour on a Monday, so my fear of gay clubs was a little easier to get over.

I walked uptown to his office and waited for him to finish his workday. When he came down, I noticed he obviously changed his clothes. He wore a suit to work every day, and today, he was wearing very tight brown pants and a polo shirt. He looked gayer than a $2 bill. Yes, I know how bad that sounds.

Thinking back, I think it was then I realized we weren’t a match. Maybe that makes me shallow, but I’m really more into masculine guys. However, I still didn’t completely write him off.

We got our drinks and found a comfortable couch to relax on in the back of the bar. We talked casually, facing each other. I was trying to convey a more flirtatious body language. I could tell he was doing the same. After some time passed, I placed my hand on his leg when talking to show my interest.

Out of the blue, one of the drag performers began practicing “her” sets. Drag queens make me feel very uncomfortable, but I’m cool with them as long as they don’t try to interact with me. I don’t need to be a part of the show. When I thought it couldn’t get more awkward, the drag queen came on in nothing but a feather boa barely covering the necessary parts. HR and I discussed drag queens and our feelings about them. I respect them and their choice. I admire their confidence in themselves and their apathy towards others’ judgement.

We talked more, but then the night began to get a lot more physical. At one point, I just went in for the kill. We were facing each other, and I took the opportunity to kiss him. After our missed opportunity to kiss last time, I decided one of us needed to make a move. I usually never have the courage to do so, but tonight, I was properly lubricated and just went for it.

We spent a majority of the rest of the night kissing and cuddling. He had his hand in the top of my polo and was rubbing my chest. He expressed how much he enjoyed it, and said, “Even if you tell me to stop, I don’t think I will. Your chest feels too good.” I was enjoying it, so he had no complaints from me.

Before we knew it, it was 11:30. I couldn’t believe how late it was, and I needed to get home. He both walked over to 9th Avenue, kissed, said goodnight and went our separate ways.

I expressed how good of a time I had that evening, and we talked about seeing each other again…

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