One Gay at a Time

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…