On a particularly hot summer I found myself bored and restless. My wife and kids were leaving on an extended vacation to visit her family in Europe. The plan was for them to be gone for two months. Of course I could not go because of my job and that was okay since I was establishing myself as a valuable asset. My manager, Dan, was my mentor and he sympathized with my situation concerning being alone for two months.
"Tony, you are a very dedicated employee and I do appreciate your loyalty. If you are interested, I would like to invite you to my summer home in Fire Island for a long weekend." What could I say but yes of course. He planned it for the following weekend after my family left.
"Thank you boss but I would not want to impose on your hospitality."
"Nonsense! Now pack up some clothes and make sure you pack a bathing suit."
And so he picked me up at my home early Saturday morning and we drove to the dock where we caught a boat leaving for Fire Island. The trip from beginning to end would take at least a few hours so I was deep in thought. I can describe Dan as a charming older man. He had been married but was now divorced. Dan seemed very happy and enthusiastic. As we traveled, he casually mentioned our final destination. "My summer home is located in the Fire Island Pines section close to Cherry Grove. You should know that this part of the island consists primarily of a gay population. I hope you don't have a problem with that." At this point what could I say. We were almost at the dock and although I was surprised, to be honest, I was a little excited at the prospect of immersing myself into the gay community. I wasn't aware that Dan was gay and I had begun to question my own sexuality. Up until now I considered myself a heterosexual but I did have feelings for men.
"Not a problem Dan. I just did not realize that you were gay."
"Like you Tony, up until my divorce, I considered myself a heterosexual, and then I discovered my true sexual identity. Forget about all things gay. We are here to have fun. You will never be forced to do anything that you are uncomfortable with." And with that said, we arrived at the island and headed straight to his summer home. I felt very comfortable with Dan. Actually he was kind of a hot guy. But I did not want to spoil our friendly relationship so I smiled and acted as if nothing had happened out of the ordinary.
When we arrived at his home I was taken on a tour of his place. It was really a beautiful home. Dan told me that we would be heading out to the beach to have lunch and relax a bit. That night we would be going to a party with some friends. "Tony, put on this speedo. It's a little skimpy but you'll be able to blend in with everyone." Although I was hesitant to wear the speedo, I wanted to make Dan happy and so I put it on under my pants and we left for a short walk to the beach. We arrived just in time for lunch. The restaurant/bar was already crowded. Dan knew just about everyone there. Apparently one of his friends had reserved a table for us, together with some of his friends. I felt very comfortable eating and chatting with this new group of men. I never identified as gay but now I felt a yearning to belong.
After lunch, we all headed for the locker room located conveniently near the beach. I stripped and put my clothes into a locker. Now I noticed that my speedo was pink and very minimal. Dan had arranged a private cabana for our small group and thankfully all the men wore speedos. Dan had prepared drinks before we left his home and now we relaxed on comfortable beach chairs sipping our mixed drinks. Was I gay? I wasn't sure but it definitely felt good to be with a group of like minded guys.
"Tony, we've been invited to a party tonight. Everyone will be there." This weekend is getting better and better. We returned to Dan's home and prepared for the party. Dan laid out a set of clothes for me to wear. Dan sure knew his fashions. The clothes were beautiful but to be honest they seemed a bit feminine. Who was I to complain. So far Dan had been a gentlemen who was very caring. And so I put on the outfit. The outfit consisted of tight white pants that highlighted my butt. The top was a see through pink blouse. The underwear was essentially a thong. Finally the shoes were white with inch high heels and no socks. I would never have worn an outfit like this before today but somehow I really enjoyed looking like a hot and sexy guy. Dan's outfit was more conservative. And so we left for the party.
The party was held at one of his friend's home. I recognized his friend from the beach. When we entered his home his friend kissed me on the cheek and told me that I looked delicious. As strange as it seemed, I enjoyed the attention. The party was in full swing with music blasting and everyone dancing. Oh yes, and there were only men at the party. Dan held my hand and guided me to the bar. With a drink in hand, we mingled with everyone. It did seem that all eyes were on me. My outfit seemed to be the most feminine one.
