Before ever stepping on a plane to Florida, I told the friends I would be traveling with I was giving myself a hall pass. If Broadway went to Barcelona alone, possibly with a bottle of lube, then I was going to Florida with some new found freedom.

I didn’t break up with him prior to my trip. If you recall from my previous post, he wasn’t my “boyfriend” either. I never heard the phase “I love you” pass his lips. We had been dating for almost 10 months, but I no longer had any indication this was destined for the long term.

I have never been single and gay. I met Broadway, and shortly after, I came out. I needed to give myself the freedom to date. I needed to explore and experience. Is this healthy for a relationship? Was I setting myself up to cheat on the man I was dating for the previous 10 months? Maybe. But was it something I needed to do? Yes. Yes, it was.

Before heading to South Beach, Miami, Boston and I discussed meeting up. When my friend K and I arrived, we checked into Essex House and went down to the beach. I noticed a guy who vaguely resembled Boston. I pointed him out to K, and she said, “Ooooo. Go for it! He’s hot!” But when he walked down to the water with a female companion, the chemistry between them seemed more than just friends. Their body language suggested they were dating. Furthermore, this guy was wearing what I would later come to describe as “straight shorts.”

It wasn’t until I overheard their conversation as they were leaving the beach that I realized it was him. We were texting each other from 10 feet away for over 2 hours and didn’t even realize it.

Later that evening, K and I walked over to the sister hotel for happy hour. The other 2 in our party would be arriving any minute, but we were anxious to start drinking. I texted Boston and told him that if he could find us, I would buy him a drink. He was staying at this sister hotel, The Clevelander. After spotting us, he joined in our happy hour pitchers. Over the course of the next couple of hours, I drank about 4 pitchers. I was truly cutting loose.

Before this trip, I had no plans of attempting anything with Boston. He was just a solid friend. We were going to meet up for a drink or two, but after K made the comment on the beach, the possibility of more was planted in my head.

When my 2 other friends arrived, we discussed dinner plans at The Royal at The Raleigh and extended an invitation to Boston and his friend.

At dinner, I made a bit of a fool of myself. I had quite a bit to drink. When we finished eating, we walked back to the Clevelander for a night cap.

At the bar, I bought a round of beers. Boston tapped the top of my bottle to make it overflow. The only problem was I didn’t have a strong grip on my beer and it shattered on the floor. Minutes later, I retaliated, only to have the same thing repeat again.

After a short while, Boston’s friend went off to bed, shortly followed by my 3 friends. Boston and I were still sitting at the bar chatting when some guy came along interrupting us talking about real estate. Boston turned to me and told me to get rid of him. This was a window of opportunity. I was drunk and Boston is hot. I started getting a bit physical with him, rubbing his leg and petting his neck so the guy would leave. Finally, he got the hint and took off.

After my third trip to the bathroom, I asked him if he wanted to go for a walk. We strolled along the beach and found a comfortable spot to chat. We talked about careers and futures for some time before the authorities chased us. We moved our discussion to a wall at the edge of the sand. At one point, we were both just awkwardly staring at the ocean when I turned and kissed him. He immediately responded, and we proceeded to make out for what could have been a half hour. People passed by making cat calls, but we continued as if no one was there.

Things started to get hot. My hands were up his shirt feeling the chest I admired on the beach earlier that day. Finally, I put my hands down his pants and felt how much he was enjoying it. And he did the same. Me being 6’2″ and him being no taller than 5’6″, I picked him up and leaned back against the wall so I didn’t have to hunch over anymore. I was really enjoying myself. He was a great kisser and the wandering hands on both parties was rather pleasing. At one point, he pulled back and said, “But you have a boyfriend.” This didn’t stop me from going back in. Between kisses, I was able to utter, “He’s not my boyfriend, remember?” He was torn about the issue. He was obviously enjoying himself, but he didn’t want to get in the middle of a relationship.

After a while, I asked if he wanted to go somewhere more private. He pointed out we were both sharing rooms. I noticed the uneasiness on his face. I responded back, “I’m not trying to have sex with you. I’m not that easy. I just don’t want to stand here making out in public…” At this point, I could see his level of comfortability dropped significantly, so we went back to our separate rooms. I sent him a text explaining my enjoyment and my respect for him.

Stay tuned. The remainder of the trip will have to wait ’til Monday’s post.