Smiles and I made plans over the Christmas break to share a home-cooked meal my first full night back in town. I was greatly looking forward to it after not seeing him for a week. We’d spent a week apart before, but not over Christmas. Something about it made it tougher for me to get through.

That morning, Smiles sent me a text. He was wishing me luck on my first day back in the office after being away for some time. It was a truly sweet gesture considering how out of character this was for him. Since I left him, he was showering me with attention I didn’t normally receive. I attribute this to our conversation the night before I dropped him at the airport. That was just my assumption, but the only other factor that changed was spending time apart.
Out of the blue, in the middle of the afternoon, he picked up the phone and called me. I’d told him I had to go to the office that week, but there was little chance I would actually be working, so I guess he felt I’d have the free time to chat. It was a very welcomed distraction from my Facebook status perusal and email correspondences.
He called out of boredom. He couldn’t seem to motivate himself to work. He was still in vacation mode from being away. “My head is still at the beach,” he added. I told him there was no need to dive back into everything unless it was urgent. We all have lazy days. Why not ease back into the workload?
Before Christmas, I bought two cashmere hats from Bonobos. Smiles had mentioned interest in similar hats. I bought them just in case we made a last-minute decision to exchange presents. I could ship them back free of charge and Smiles would be none the wiser, but that seemed like a waste. I got a great deal on them considering how much he paid for the last one he purchased, so I decided I was going to ask if he wanted them. It wouldn’t be a gift — I would just be facilitating the deal.
“Are you still interested in cashmere hats, and what is your price point?” I asked. He told me anything under $80 each, which was $20 more than what I paid for them. I decided I was going to show him the hats and come clean about how I came to purchase them. I was worried I would look anxious in his eyes, but since we had our talk about where we were, I decided I needed to start being more of myself. It’s very much like me to do something slightly awkward and come clean about it. I’m very honest when it comes to things like that, shame or no shame. If he didn’t like it, then he didn’t like me.
That night after work, he came over. He texted me as he was getting on the PATH. When I didn’t hear from him for over a half hour, I tried calling and texting. I was getting no response. I wasn’t sure what happened, but I was hoping the meal wouldn’t be overdone waiting for him. Finally, he told me he’d arrived in Hoboken. When he got to my apartment, he told me he’d gotten on the wrong PATH train and ended up in Jersey City. He had to switch over and come back towards Hoboken.
I filled plates for the two of us, and we sat on the couch to eat dinner while we watched TV. Smiles loved the meal. He said it was cooked perfectly and everything was delicious. I was very proud and thrilled with how much he enjoyed it. One thing I love to do is cook for a man, especially when I get such rave reviews.
While we watched TV, my attention was constantly stolen by the reflection of headlights on the windows across the street. He kept asking what I was looking at, and when I told him, he poked fun at my inability to keep my attention fixed. We had a good laugh about it.
Smiles asked if I had any ice cream to finish our meal (you know him and his sweet tooth). I didn’t have any. We had two options. We could venture back out into the cold to pick up a pint, or we could settle for a variety of candy I had stashed in my room. He settled on the candy.
After dinner, we moved things into the bedroom. I was anxious to hop into bed with Smiles, just to feel his body against mine. I didn’t even care if it involved sex. I just wanted to be close to him. But, before we hopped into bed, I decided to bite the bullet on the hats. I explained, and he decided he wanted to keep the gray hat and have me return the black since he already had one. He gave me cash, and the transaction was complete. I was glad I didn’t just send the hats back without consulting him as many of my friends suggested (I have a habit of doing what I want even against my friends’ better judgment).
We laid in bed and exchanged random stories. We discussed how he was healing after his appendectomy. Like I said before, I was going to start being myself, so I told him the ridiculous story about my belly button. For some unknown reason, when I was in college and I got drunk, I would encourage my friends to feel my belly button. I was a swimmer so I had a flat stomach, and when I got drunk, I like the way it felt (maybe the beer pushed it out a bit). I insisted it was incredibly sexy and even took some of my friends’ finger and guided it to my belly button. I also proceeded to tell him about the time my belly button was handpicked as the body shot glass for a bachelorette party when I was in Key West. “ ‘Wow! You have the Grand Canyon of belly buttons!’ one girl shouted,” I told him. He laughed and looked at me like I was from another planet as he examined my belly button.
The rest of the night was more of the same — Lots of cuddling and chatter, but no sex. I was fine with this, as I was just happy to have him in my bed. We both brushed our teeth and climbed under the covers. I was going to bed a happy man that night, and I was looking forward to waking in the morning to a sexy man in bed next to me.
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It was that time of year. The annual family trip to Ocean City, Maryland. Every year I both looked forward to and dreaded this vacation. While it was a week to disconnect and relax, I knew I was surely in for some excessive boredom. Don’t get me wrong, I love my family, but we’ve been going to the same place for years. I can only take so much of it before getting tired of it.
We arrived on a Sunday, and one of the first things I did was turn on Grindr. I’m addicted. I know. It’s an issue, but I also knew it would be my salvation from the boredom that would ensue. After riding in the back of the car with crap piled around me feeling like a twelve year-old, I needed to get out and do something. My parents plopped down in front of the TV, a position they would take for the next three nights as well. I wasn’t feeling so lazy. On top of that, I was already getting grief for playing on my phone while we sat and watched TV. I needed to get out.
I managed to find a nice guy on Grindr not far from where I was staying. He was from Pa, not far from where I grew up. He certainly wasn’t around the corner, but he wasn’t far either — 2.5 miles. I decided to go for a run. I could run down to his condo, say hi and turn back. It was also a good way for me to squeeze in a run as well. I told him I was going to run down there. As I got near, it appeared he was going to chicken out on me. I told him, “You’re really going to flake on a guy who just ran 2.5 miles to say hi to you!?”
Eventually, he came out to say hi. I think he had ideas in his head of us blowing each other on the beach, but I was just there to say hi. We walked around the block and talked about a few things. He was no adonis, but he was certainly a nice guy. I thought it would be nice to grab a drink with him later in the week just to chat. I wasn’t looking for anything sexual while down here on vacation. I was turning over a new leaf, remember? I said goodbye and ran back home.
The next day, a local guy found me on Grindr. He was a bit of a sweetheart. We swapped a lot of pictures, and he expressed his interest in getting naked with me. This would be very tough. I would have to plan a way to get away from the family without raising suspicion.
That’s when I created my friend “Will” from college. He was down in OC with his family. He was based on a real guy, so it wasn’t difficult to come up with material on how we knew each other, but he was not real.
Monday night, the guy I met on the run hit me up for a hookup. I told him that’s not what I was looking for. He managed to find service elsewhere. A guy invited him over, and they gave each other head. He told me how incredibly hot this guy was, but also about how he wasn’t fully comfortable with his sexuality.
In any case, “Will” and I were going for a run that Tuesday morning followed by breakfast. In reality, I was meeting this cutey for breakfast at his favorite local spot and then heading back to his house if we hit if off for some fun. Breakfast was very nice and we hit it off. I followed him to Ocean Pines, a ten minute drive from breakfast.
We went into his room and had great sex. It was just what I needed. We both really enjoyed ourselves a lot! The time came to say goodbye and head back to the family. On the drive back, I was beaming. Sex always looks good on me. Just then, N texted. He totally ruined my high. I was on this vacation to completely forget about him for a while, and he was making this nearly impossible. This was the second day in a row he texted. I called Boston to brag about my morning romp and bitch about N once again. Poor Boston.
That night, the guy from the run explained to me his boyfriend was arriving. This was the first time he brought up the fact that he had a boyfriend. My relationship wounds were still fresh. Infidelity was a BIG turnoff. He proposed we all go out, but we would have to meet “by chance.” I said, “What? So I sit at the bar looking all sad, and you two come sit next to me and chat me up? Not gonna happen.” Besides, Tuesday night was an annual tradition for my father and I to go to Hooters for wing night. He knows I am gay, which makes it even more ironic, but we always have a good time. It’s the one time of year he orders a beer when we go out. There is an element of humor added as well. My mother loves the wings, but she refuses to step foot in the fine establishment, so we order too much food and take the leftovers home to her.
By Friday, his boyfriend was back home in Pa. We made plans to grab a drink together, nothing more, but he was having a hard time committing to anything. In the meantime, another guy was hitting on me on Grindr. He was good-looking in his picture, and after talking for some time, he asked me to come with him and his 3 friends to Rehoboth for the night. I debated in my head just how risky this was. Looking back, it was a really dumb idea, and I never should have done it. But, life without risk is life unlived.

They picked me up and we went back to their condo for a few drinks before heading up to the bar. When I met all the friends, I knew I got myself into a bad situation. These guys were all hicks from right outside D.C. I wasn’t scared, but I also suspected I wasn’t going to have a good time… To be continued…
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