Posts Tagged Halloween

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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Back On Top

In unrelated news, I came across this video from my fellow blogger, http://www.ty-curious.com/. He shared it with me, and I think it’s spectacular. Totally safe for work! Hope you like it! Take the time to check out his blog too. Great guy!

On with the story…

After my ride back to Hoboken, Smiles and I chatted on Facebook.

He described his drunken night involving too much Patron and a lost iPhone. He hadn’t had a chance to track it down, so I offered my assistance to make some phone calls for him. He was grateful, but had it under control. While he described his night, I described my time out in the sticks with no power or technology. “Yeah… It was a real Amish paradise,” I said.

Once again, I had to facilitate plans with him. He typed, “Okay. Off to go get food. I’m starved.” I quickly replied, “What are you doing later?” I knew it would be difficult getting ahold of him the second he signed off for the day. It’d been a while since I’d seen him, and I was anxious to do so. “No plans, although I may go back to the bar tonight for a Halloween thing,” he declared. I wish he had the same desire to see me to invite me without provocation, but I’ll take what I can get. “Wanna try to get together later?” I asked.

“Jump on the bike and come over and have brunch with me,” he finally stated. I explained the bike was snowed in with a dead battery, but I told him I’d meet him for brunch. I quickly made my way into the city to meet him at the Christopher Street PATH station. I arrived well before him and waited for him to show. I couldn’t call to find out what was keeping him, so I tried to occupy myself with my phone.

When he finally arrived, I wasn’t greeted with a kiss. I could have initiated the situation myself, but again, I was still in the mindset to play a little hard-to-get. We walked to a nice brunch spot neither of us have tried before, Barbuto. It was great. We got a nice seat next to the kitchen, which in most situations is a bad thing, but in this case, was entertaining.

Smiles ordered a beer after wavering between that and a bloody mary to help cure his hangover, and I ordered a glass of red wine. We took the time waiting for the food to arrive to catch up with each other. He was a little quiet, but I had plenty of stories to tell from my time home. We talked a bit about his family as well, and I started to get a better picture of the dynamic going on there.

Our food arrived, and we were both very pleased with the results. After we paid our tab, we decided to walk around a bit since the weather was so gorgeous. We walked to Doma Coffee Shop to grab coffees while we walked around. We had no plan for our day. After we grabbed caffeine, he turned to me and asked what I wanted to do. I told him I was just happy to be out, and it didn’t matter to me what we did. We started to walk around aimlessly. When we came upon Pleasure Chest sex shop, he suggested we pop in. This wasn’t the first time walking into a sex shop with him. I was game.

We looked at all the toys in the place and even asked one of the workers there to explain one of the feminine toys to us. We had more than a few laughs as we perused the store.

We spent the rest of the afternoon walking around SoHo looking for hats to replace the one he lost. I was happy to spend the day with him. We did some shopping for other things while we searched for hats. While I was checking out to pay for the flannel shirt I picked up, I could see in his eyes he was exhausted. He was fading fast. He suggested we go back to his place to take a nap. I myself wasn’t feeling very sleepy, but I rather liked the idea of napping with him.

We got back to his place and climbed into bed. I put on my new flannel and got comfortable. Surprisingly, I passed out rather quickly. He, on the other hand had a hard time falling asleep.

Warning: The following may be too graphic for some. After about an hour, we were both awake. He turned to face away from me, so I decided to make a move. I engulfed him in my arms and spooned with him. After some time passed, I gently began caressing him all over and slid my hand between his thighs. I began massaging him until he turned his head back to kiss me. It was on — FINALLY! Things only got more passionate from there. It wasn’t long before he pulled out a condom, put it on me, and climbed on top. I was finally getting my turn as top dog (even though I was on the bottom). The sex was good, and I enjoyed having sex facing him with the lights on. However, once again, he finished, and I wasn’t able to.

Embarrassment came flooding in.  I was very attracted to him, and I enjoyed the sex, but something underlying wasn’t allowing me to relax and fully enjoy the moment. I was very close, but I just couldn’t get over that last hump (no pun intended). This wasn’t the first time this happened, but it certainly didn’t make it any easier to deal with.

After sex, we both showered and cleaned up. He had plans to meet friends at his favorite restaurant to say goodbye to a bartender friend who was leaving for another restaurant. I was a little curious why he didn’t extend an invitation, but I didn’t want to dwell on it. We made some progress, and I wanted to concentrate on the positive. I was doing my best to play hard-to-get, but I really liked him. I wanted this to continue. I wanted to get to know him more. I wanted to be closer to him physically. I wanted him.

We got dressed and walked towards the PATH and Extra Virgin, where he was headed. When we reached a crossroads, we said goodbye with a quick kiss and went on our separate ways.

Later that night, I got a message from him complaining about having to go to the bar to see if his phone was found. I sympathized with him and wished him luck.

When he got back from the bar, he messaged again to tell me he had no luck. I felt bad for him, but selfishly, all I could think about was how hard it was going to be to get ahold of him without a phone. The next couple of days would pose an interesting challenge.

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The Game — Hard To Get

As predicted, Monday was the day from hell. We had a huge pitch on Tuesday morning, so it was constant work until the end.

There was already no chance Smiles and I would see each other. However, we did get to chat on the phone briefly. He had to do work with his film, and I would be working until the wee hours of the morning to finalize the content for the pitch. I didn’t end up leaving my office until 1:30am.

I really wanted to see him Tuesday. I wasn’t going to be around the rest of the week, and whenever I have a long work pitch or long work trip, I look forward to decompressing with a sexy guy, even if it doesn’t involve sex. I asked him if we could do something, but he already made plans.

I was heading home Wednesday for my grandfather’s funeral. It was going to be a while before I got to see him again, and I was really disappointed. Things were really getting strained between us, at least on my end. We weren’t having sex as often as I’d like, and I was constantly on a roller-coaster of emotions. Smiles would pay a lot of attention to me and make me feel great, and then retract and shy away from me. I didn’t know how much more I could take it.

I decided I was going to play hard-to-get. I wasn’t going to text or call at all. If he still wanted to see me, he was going to have to put in the effort. I was at my emotional breaking point.

This was no easy task for me. I struggled with it. I carried my phone with me everywhere I went in case he tried to call or text, but it was silent. Part of me wondered if he thought it was a very personal family time, and he just didn’t want to bother me. But, the bigger part of me thought he had other things with which he was preoccupied.

Finally, Thursday he texted me to see how I was doing. It was progress. He was texting to check up on me, and I appreciated it. I texted him back after some time passed.

When Friday came about, he called and left a message. It was impeccable timing. I was just about to walk into the funeral parlor when my phone began ringing. After the viewing, I stepped out from the family gathering and called him back. We had a nice conversation.

The following day, I went to the funeral. Afterwards, I came home. I have awful cell service at my parents’ house. I finally managed to get signal by using the Wi-Fi. Ironically, right after I texted him, we lost power in the snow storm, so if he responded, I couldn’t read it if I tried.

I was home with no power, no internet, no phone and no TV. It had snowed about a foot outside, so we were trapped. On top of it, I was missing the Halloween festivities with my friends back in Hoboken. I wasn’t heartbroken about that, but I was disappointed. Instead, I spent the day shaking snow off trees so the branches wouldn’t break.

I was really feeling ignored overall by Smiles. The time away wasn’t a good thing for me. It was making me realize how little attention he was paying to me. I started to think about some of the other prospects I had spoken to. I could have pursued LES, but he was young and lived in an inconvenient part of town. There were a few guys who were still sending me messages on OKCupid. While I wasn’t seeking out anyone new, I maintained communication with them. I was now beginning to think about them as prospects. All I knew was I deserved better. Was I just jumping the gun? Was it still early with him? I personally thought we should have been over that hump, and if he was interested in me, he’d want to spend more time with me.

When Sunday arrived, my sister and I made our way back to Hoboken. It was a bit of an adventure with the snowfall and trees laying across the road. Once I got back to Hoboken, I hopped on Facebook. Smiles messaged me, and I learned he lost his phone. He told me about going out for Halloween and how he lost it. We made plans to grab brunch, and I made my way into the city. I didn’t forget about the lack of attention he paid me, but I tried to concentrate on the moment at hand. I was going to proceed with skeptical optimism. It was the only way I was going to keep my sanity.

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