One Gay at a Time

That time of year finally arrived — The end of summer. It’s always both a sad time and a happy time for me. I am a sun worshiper. I love the beach, and I love a good tan. It means the days get shorter, and the nights get longer, which isn’t necessary a bad thing when you have someone to share those nights with. Of course if you’ve read this blog at all, you know I don’t have that someone. However, it is a happy time for me because it means the annual Martha’s Vineyard trip many of my friends and I take has arrived. We always have a blast, and it’s one of the best crews I’ve ever traveled with. Everyone is mature and responsible, yet they still know how to have fun.

Since things ended with N, I kinda went on a whoring rampage. My time in OCMD was nothing short of scandalous. But, I was having fun. And, why shouldn’t I? I’m a single 27 year-old who is still finding himself in this new gay world. While everyone was having sex in high school and college, I was a good boy. I had my share of awkward hookups with women, but nothing successful enough to blossom into a relationship and rarely something worth revisiting again. Plus, the only way I would get better at sex was practice. So practice away I shall.

We hopped on the ferry to the island, and I fired up Grindr. I was beginning this trip with five other straight friends and ending it with ten. I knew I would crave some stimulation from other like-minded gentleman. Many of my friends were in relationships, some of which were tagging along on the vacation. I didn’t want to always be the third wheel. I made an effort to find someone to maybe sneak off on my own with.

Of course I found a few attractive men right off the bat, but pickings were actually quite slim. Many of the attractive ones happened to be on the mainland. One guy in particular messaged me. He was on the Vineyard covering the President’s vacation and had stayed on longer to cover Hurricane Irene as a photojournalist for CNN. He was staying in Vineyard Haven, where we were pulling into port around 9:00am. He could see my ferry coming in to port from his hotel window. He suggested I come by. I was definitely intrigued since he appeared to be quite an attractive man — Fit and handsome. I was also intrigued because originally he told me he was a CNN journalist in the President’s press corp. I thought it would make for an interesting story for the blog (This thing can be such a bad influence on my decision-making process sometimes!). He was a bit older, but I was on vacation, so my standards could also take a vacation. I explained to him I was just arriving on the island and would need to get settled in. Coming over for a quickie was not a solid option. That didn’t deter him. He certainly was persistent. He was waiting for a ferry, but was unsure which one he would get on due to the cancellations from the hurricane.

We arrived at our house and began unloading the car. We settled in and unpacked. I was originally under the impression we’d be heading directly to the beach, but everyone seemed to be lounging about. I inquired if I would have time to go for a run before we went anywhere. Everyone agreed they weren’t heading anywhere fast. I wasn’t really all that into meeting this guy, but at this point, there was no reason why I couldn’t. Am I proud of this? HELL NO! I was stupid and saw it as a challenge. So, I told the guy I was on my way.

In my haste, I left for the run shirtless. I hate running in a soaking wet t-shirt, so I left it behind. I wasn’t thinking ahead to the part where I would be walking into a hotel without a shirt on soaking wet from a run.

I texted him the whole way, almost getting hit by a car twice. He told me his room number and planned to leave the door ajar. He would be waiting for me in the bed. I was not really comfortable with this. I really felt like a gigolo, only I wasn’t getting paid. I explained my need for a towel when I arrived to help with the sweat from the 1.5 mile run, so he left one hanging on the door knob for me.

When I arrived, I walked right past the front desk straight to the elevator. When I go to the door, I entered the room. He was waiting on the bed for me. I removed my shoes and began to take off my shorts. He pulled me in, and we started to make out. I didn’t realize from his pictures he was quite the redhead. His entire body was freckles. He was my first ginger. Without getting into the details, we had our fun. SAFE fun. When all was said and done, I picked up the towel again and cleaned up as best I could. He couldn’t stop telling me how sexy I was and how great my body was. I don’t embarrass easily, but he was certainly making me start to blush. He told me if he didn’t get on the ferry that night, he would be calling upon me to go on another morning run the following day. I knew this wasn’t going to happen, but I humored him anyway. We exchanged a kiss, and I was back off on my run home.

Of course, the second I left for my run, everyone back at the house began speculating on my reason for leaving. I knew this was going to happen, and I could tell the second I walked back into the yard they had been discussing this. One my friends, a very loyal reader, immediately grilled me on how my run was. I saw right through her intentions, and I wasn’t going to give her the satisfaction of being right — Until now. I lied. I denied any lewd behavior on my part. I simply told them I was stuck on the other side of the drawbridge and had to wait for it to be lowered again. They bought it, and with that, I went in the house to shower and get ready for the day.

Ironically, later that night we had dinner on the beach in Menemsha. We stayed to watch the sunset and had a blast. We had no cellphone service out there because it is a remote part of the island. When I arrived home, I notice a message from the ginger mentioning seeing me on the beach that night. It was a little creepy knowing he didn’t take a ferry that day and saw me that evening. I was very grateful he didn’t walk up to me and say anything. And, of course, the following morning I had a request for a repeat, but there was no need to revisit that again.

I wasn’t on the island an hour, and I had already gotten myself into trouble. This was certainly going to be an interesting vacation…