Just introduce yourself and be chill

Taking into account what Julia told me about Colin, it would be wiser to have a not so head-on approach. I'd introduce myself and hang out. It may take a while, but once I made him comfortable enough, I'd let him know who I really am.

Colin apparently was headed to his room. But, as Julia had shrewdly observed, he was on his own. I could not start a conversation dressed-- or rather undressed, as I was. So I followed him from a decent distance. I wanted to know what his room number was. 3012 was the lucky number. Once he got in, I rushed back to Julia.

"I think I have to approach him discreetly" I said to Julia. "But that would mean I need a night off the balcony and I need some clothes for the night. Is that ok with you Mistress?"

"There's a much bigger prize to gain if you succeed than another chilly night at the balcony. And I can live with you appearing to be a normal guy for a few hours. Go ahead, you have my permission to wear whatever you want and come back to the room as late as you need. If you succeed, you know what will happen. However, if you fail, you'll have to make it up to me for not spending the night as I wanted. You'll be punished accordingly."

It was a typical win-win situation. For Julia, that is. For me, it was a lose-lose situation. If I succeeded, I'd get cuckolded and probably have to witness it happening right in front of my eyes. If I failed, I would get punished. And knowing Julia, she would not go easy on me...

After I got dressed as a regular human being, I stalked Colin's room. He spent at least two hours in there. What was he doing? Is he a work-aholic? Or was he just having an extra long jerk-off session? When I heard the sound of his door opening I started walking his way, as if coming out of a nearby room.

"Howdy neighbor," I said in my most friendly voice.

"Hello, good evening," Colin replied.

"All alone this evening, Mr...?"

"White, Colin White is my name. It's a pleasure to make your acquaintance. Yes, I came to Jamaica on my own. I won a reward on my job and my wife couldn't come..." his words started to come out softly, as if he was making an effort saying them.

"Something bothering you Mr. White? I'm here on my own as well, would you like to join me for dinner?"

"Please call me Collin. I'd love to have company for dinner!"

Dinner was fun. We spent three hours talking, getting to know each other, I told him nothing but truths except for the fact that I have said to him I was alone in Jamaica when I first met him. And he spilled the beans about his life as well.

Despite being so loyal to his wife, his marriage was in deep crisis. She didn't want to join Colin on this trip to Jamaica, even though it was a free trip, won by his efficiency in making money for the company he worked for. He opened up so much to me that he even cried a bit when telling me all about his ups and downs with his better half. So this gave a way to talk about making me a cuckold...