Testing Boundaries

Once again, today is another double post to make up for lost time. If you are just visiting for the first time today, scroll down to the previous story to keep up with the timeline. Enjoy!


It had been a long work trip. I didn’t have any spare time for anything fun other than work. The one hour I had free, I spent on the treadmill trying to get back in shape for the rapidly approaching warm weather.

After my meeting, I sped to the airport. I wanted to get home so I could start my weekend off right. I began texting everyone back home to see what they were up to so I could be efficient with my time when I landed. I sent out a flurry of texts and received a few responses before taking off. I knew at least a few people were up for drinks at the bar. I also decided to take care of my pre-game at 30,000 feet. I ordered two scotch on the rocks to help get me started.

When I landed, I got more responses to my texts. Some people were too lazy to go out. They received harassing phone calls from me urging them to sack up and join the able-bodied and willing. It was no use. I also texted my Grindr friend who recently moved to Hoboken from the city — Much closer to me. I asked him if he wanted to check out the Hoboken scene. I warned him it would be all straight bars, but he was down.

I picked up some food at the airport I could eat in the car on the way home. When I arrived, I quickly showered and got dressed. My friend took a little longer to get ready, so I had to wait for him a bit. I was getting messages from my sister and friend who were at the bar waiting for my arrival. I told them to keep their pants on… I was en route.

I met my friend on the corner and walked with him to my local watering hole, McSwiggans. I told him about the bar as we walked. He asked how my trip was, and we continued the small talk.

I hadn’t told anyone I was bringing a guy with me. They were a bit surprised. But, I wasn’t bringing him as a love interest. I was bringing him as a new neighbor and friend. He didn’t know Hoboken, so I thought I could show him around a bit. I also knew he was normal enough he would fit in. I introduced him to everyone, and we got beers. I spent a lot of the night chatting with him, but mixed in with my friends/sister as well. As the night progressed, my sister grew more and more intoxicated. She started rubbing her a$s on me like she does with people when she’s drunk. It took a lot to get her to stop.

After some time, I got a text from one of my teammates from college. He was in town at another bar, so I gathered everyone up, and we made our way to Black Bear. He was there with his new girlfriend and her friends. When we arrived, I needed to relieve myself immediately. He came down the stairs and joined me standing in line to hit up the bathroom. After we all finished using the facilities, we made our way upstairs. My group grabbed a table, and my friend dragged me over to meet his group. He introduced me while my Grindr friend followed me. His girlfriend was already three sheets to the wind and shouted into my ear, “Is this your boyfriend?” I explained he was just a friend, and we all continued chatting. When I realized I was neglecting my other friends, we made our way back to the other table.

By then my sister was wasted, and she needed to go home. Luckily, one of the guys in the group who is utterly chivalrous, volunteered to escort her home since they both lived uptown. I said goodbye to both and was left with P and my Grindr friend. When my Grindr friend went to the bathroom, I explained my predicament to her. Until this point, we were just friends, but I wasn’t sure if maybe we could be more. I asked her if I should make a move.

“Why not!? What do you have to lose?” she asked. I told her I liked having him as a friend, and if I crossed that line, I wouldn’t have a friend anymore. I wasn’t sure which I would rather have. A new friend or a new guy to date. She still suggested I go for it. I decided I would make a game time decision later.

I felt like it was mine for the taking. He always seemed interested but who could really tell? I was purposely putting out the friend vibe, but I think if I escalated things, he would be interested.

The night was dragging on, and I was tired. We closed our tab and made our way for the door. P lived in the opposite direction of my new neighbor and I. Furthermore, we decided to stop at Cluck U and get a late night snack before heading home. When he asked if we were eating there or somewhere else, I volunteered to go back to my place.

When we walked into my apartment, we sat at the counter eating and talking. When we finished, he needed to use the bathroom. I moved over to the couch in hopes he would as well when he came back into the room. He didn’t get the hint. He sat back down at the counter until I suggested he join me in the living room. When he did, he sat in the chair next to the couch. This was going to take some work.

We talked some more before I finally moved to the chair and said, “I hope this isn’t out of line, but…” and I laid a big kiss on him. He totally kissed me back. It was great. Taking the risk paid off. When I pulled back, I asked him, “Did I surprise you?” “Well… YEAH! Of course I was surprised. I just thought we were going to be friends,” he replied. “I know. I was putting out that vibe on purpose. I wasn’t sure what would come between us,” I told him. He just smiled, and we kissed again…

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  7. Valentine’s Letdown « One Gay at a Time
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  9. A Colombian Night « One Gay at a Time

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