When I started chatting with and mailing letters and stories to him, it was just fun sexy electronic play. We talked about everything. Most of the time it was real hot and we’d both cum to the stories and chats.
Then after about three months of this we began making suggestions to meet each other. I live and work in Long Beach. Jerry lives in Cleveland. So the hardest part was where and when to meet. I had been planning to take a vacation and wanted to go to Mexico for a few days. When I suggested this to Jerry, he was all for it. So, we planned our visit to Mexico over the Internet. Each time I received or sent an e-mail about the trip there would be a fantasy story.
During the first chats and letters, the fantasies would surround the idea of massages, showers, and mutual masturbation and would usually end with a healthy session of anal sex. During the four months of planning, the excitement was getting to be unbearable. During the last two weeks, we began calling each other and having phone sex. The build up was great!
Then the day was at hand. We took off from our airports at basically the same time. However, I arrived at the hotel in Cancun three hours earlier than Jerry. I went to the room and began to get everything ready. The room was beautiful. We had a balcony, which was semi-private but I saw nobody from the adjoining room. The view of the beach was great. We were up high enough that nobody could see passed the railing of the balcony, but not too high that we couldn’t see the people on the beach. There were bikinis, and thongs, sun tan oil and all sorts of goings on.
Back inside the room, I checked the wet bar, poured myself a drink and took it with me to the shower. I got into the shower and began a long, hot rinse. I was so nervous. The hot water and the scotch slowly began to loosen me up. While I washed myself, I began to think of Jerry and all of the fantasies we shared. I was wondering which one we would fulfill first. I began to get hard and had to pay attention to my erection.
I soaped my penis and my shaved balls. I began to slowly stroke my cock from the base, to the head. Then, when I reached the head, I squeezed and rotated my hand. Then worked back to the shaft. While I was slowly pumping my hard cock with my right hand, I began to massage my anus with the other. I used some conditioner, (I like conditioner, because it’s slow slippery), I began to massage my hairless ass, moving my hand all the way from the top of my crack, to my hole and slowly inserting one finger inside myself. When I began to get real hot, I slipped two, then three fingers inside me. Before long, I was so hot that I was matching my finger fucking to the pumping of my cock. When I came, I came hard and almost collapsed on the floor of the shower.
After my self-pleasuring was soooo successful, I got out and toweled off. I did some touch-up work on the shaving of my crotch and ass, looked my self over in the mirror and decided that I was ready. I figured that I only had about another hour before Jerry arrived. So, I dressed in a light shirt, white thong and cotton pants.
I was really getting to the point that I didn’t know if I wanted to do this. It wasn’t my first time with a man, but I didn’t know about meeting someone in Mexico that I had only written to, chatted with and came over the phone with. However, my thoughts of security were abruptly interrupted, when I heard the door to the room opening. There he was!
Jerry had described himself as an average man. But, I couldn’t believe how handsome his idea of average was. He was about my height, and weight, he had brown hair and the most intriguing grayish-blue eyes I had ever seen.
Jerry smiled at me; I smiled back and could think of a damn thing to say. So what were my first words? Well, here we are. What? Jerry sensed my uneasiness, and smiled a wonderful smile. He said, “don’t worry, I’m just as nervous as you”. He approached me and we shook hands.
While we made some small talk, I showed him around the room. We had a honeymoon suite that we both chipped in for. It was expensive, but very well worth it. The room opened up into an entertaining area with marble (like) flooring, two steps up to the corner window and balcony. There were two bedrooms and one bathroom. I showed him to his room and he began to unpack.
While he was unpacking, I stood in the door way and we continued our talking. He was telling me of his flight and how excited he was to finally be doing this. I told him that when he came into the room, I was seriously considering getting lost in Cancun and not going through with this. He looked at me with a surprised look on his face, walked to me and lightly kissed me on the mouth. He stepped away, took his hand in mine and said, “I almost didn’t get on the plane”. I dropped his hand and asked him if he wanted a drink.
After we had a few drinks on the balcony and took in the view (of the ocean). We decided that we’d go have dinner in the hotel restaurant.
Downstairs in the restaurant, we had a great meal. Steak for both, salad and a few more drinks. A few times during the meal, he ran his foot up my leg. We brushed hands a few times and were beginning to get turned on. Neither of us is gay, we are both bi-sexual and there were no outward signs that I could tell, that we were together. We exchanged a few knowing glances and smiles, but other than that, I think we appeared to be a couple of buddy’s in paradise.
After dinner and a few more drinks, we decided to go into town and find a bar. I agreed and thought that I couldn’t drink too much more, because I wanted to be conscious for the night ahead. We found a quite Mexican bar about three blocks from the hotel. We entered and settled into a couple of wingback chairs. We ordered drinks and began to talk about more personal topics.
Jerry asked me if I was still up for some “playing” around that evening. I smiled ruefully and told him that if it were up to me, we’d leave right then and go back to the room. He laughed and told me that he wanted to have a few more drinks and flirt with me. I was all for that too. I liked the idea of building up to the moment with flirting, anticipation and maybe a little bit of seduction from and to each other.
There were a few women in the bar and we danced with them a few times. During the time that we were in the bar, the crowd went from quiet and reserved to a loud, laughing gaggle. Apparently, the bar was a favorite of the local area. We had a great time. During the night, and more and more the drunker we got, we became more and more adventurous in our flirting.
At one point, while we were walking to the restroom, Jerry grabbed my ass from behind. I stopped walking so that he would get closer and I reached back and grabbed a handful of his crotch, giving him a little squeeze. While we were in the bathroom, relieving ourselves, we each took little peeks at the other. But, I couldn’t get a good enough look.
