The most thrilling night of my life. Part II

On the drive back to Chicago from Disneyworld, I was kind of hoping my dad would pull back into the same motor lodge so we could stay the night there again. All I could think about was Trent and the phenomenal encounter we had that very special night. Of course I knew the odds were a million- to-one that he would be there again. But I didn’t care. The odds were worth it to me. And besides, we had to stay someplace. So it might as well have been there.

But my brother and sisters wanted to try some place different. So we passed the motor lodge by and drove about 120 miles further up the interstate because everyone but me wanted to get a jump on the final leg home the following morning. My heart sank as we passed by the exit. There was a large freeway sign that read: “best Motor Lodge-- This Exit”.

However in my mind, the sign read : “Best Time Collin Ever Had Motor Lodge--This Exit.”

When we arrived home the following afternoon, I pulled the ring out Trent gave me and put it in my lock-box that I kept under my bed. The whole time we were at Disneyworld, I kept his ring in my pocket so I could admire it at least five or six times a day. And every time I stared at it, I thought about that wonderful night and especially how much Trent’s hot sexy body turned me on. It had to be a true Godsend that made me walk into his room that night by mistake.

As the weeks passed that summer, I could tell I was changing. I no longer had the same feelings for my girlfriend Brittany or for that fact any girl. The simple fact was girls just couldn’t satisfy my urges the way guys did. When I jacked-off in the bathroom, all I could fantasize over were guys. And every so often, I would picture Trent fucking me on my back with my legs over his shoulders while my girlfriend Brittany looked on in spite.

When the last week of July rolled around, I was climbing the walls for another gay encounter. Not only did I want to suck a nice juicy cock like Trent’s again, but I desperately needed one up my ass. And it wasn’t as though I lived a nurtured and sheltered life. I knew where gay guys mostly congregated. Aside from the bars, they hung out at the coffee shops along Halstead St, the Museum of Fine Arts, the beach by the Gold Coast and the three downtown YMCAs.

Given we lived on the north-side of town which was only about nine miles from the downtown area, or the “Loop” as downtown Chicago is commonly referred to, I decided to pull some money out of my savings account and purchased a monthly metro pass so I could ride the “L” (above ground subway) into the heart of the Loop. Once I got onto the “L” for the short ride, I would pull Trent’s ring out and place it on my finger. I wanted him to be with me and I knew he always would be whenever I wore his ring. Normally I dressed in summer casual-- wearing docker shorts, a tank top and sandals. I also wore my 18 karat gold men’s necklace that my parents gave me for Christmas just to make myself look a little more flamboyant.

The first week, I mostly hung out at the coffee shops along Halstead St. and paid a couple of visits to the art museum. But I really didn’t have any luck. What few guys that I did talk to, I wasn’t interested in. Some were way too nelly, some were too fat, some were too old and some just weren’t my type. In my mind what I was really looking for was another Trent. I wanted a masculine & mature straight-acting good looking professional kind of guy.

The following Tuesday, I met a guy I liked at one of the coffee shops during lunch time. I was sitting at a table reading a magazine and drinking coffee when he kindly asked if he could join me. When I looked up, I gladly agreed for I thought he was pretty good looking and I wanted some company. He was about 5’11, black hair and really pretty green eyes. He was dressed in very sharp dark blue conservative business suit, white button down pin-point oxford shirt, bright red silk tie and had a beautiful gold Rolex strapped around his wrist. Indeed he was the good looking professional guy I had my heart set on.

The minute he sat down, he reached across the table to shake my hand. He introduced himself as Dean. I gave him a firm handshake and introduced myself as Collin.

At first, we talked about the weather to kind of break the ice. Then we moved on and talked about ourselves. I learned he was originally from Joplin, Missouri and had gone to school at DePaul University a few miles away. He had just turned 34 and was director of operations for a small bank just around the corner. After he graduated, he decided to remain in Chicago and started working at the bank. During our conversation he admired my ring and asked where I got it. I didn’t want to tell him the exact circumstances, so I just said it was given to me as a present and left it at that.

When one o’clock rolled around about an hour later, he kindly said, “ Collin I need to get back to work. But would you like to wait around for a few hours and I will take off early? I can meet you back here at, say, three o’clock. Then we’ll go back to my place which is just about a half-a-mile from here and hang out for a while.”

I thought about it for a few seconds, shrugged my shoulders and good-naturedly replied, “Sure, why not.”

He looked at me with a pleasant smile and replied, “Hey Great”.

He casually got up from our table and said, “ OK Collin, I need to get going. Why don’t you go over to the new IKEA they just opened down the street and check out the store. It’s supposed to be their largest one in the country.”

I replied, “Well thanks, I just might do that.”

After he turned and walked out the door, I thought about what was going to happen in a few hours. We were definitely going back to his place so we could have some good old fashion hot sex. I thought it was interesting that he never asked me if I was gay. I quickly concluded that guys just didn’t just come right out and ask that kind of question. Rather they could sense it which I was sure he perceived in me just like I could in him. I mean why else were we going back to his place? It certainly wasn’t so we could just hang out together and talk about sports like good friends would do so or something like that.

And one thing I could definitely tell from almost the moment I met him. He was extremely a picky guy. I knew he wasn’t the kind of person who fooled around with just anyone. Maybe that explained why he didn’t have partner--he was just too picky. I think that’s why I liked him. For one thing I wasn’t worried about getting any kind of transmitted disease which of course I knew rocked the gay community.

The two hours flew by really quick. I went over to IKEA just like he suggested and looked around for a while. Then I talked to some gay guys I met there who were also looking the store over. I got back to the coffee house about 10 minutes before three o’clock Unexpectedly I became apprehensive and nervous for some reason and starting shaking a bit like I did the night I first met Trent. So I took about three deep breaths to calm me. I ordered a cup of decaffeinated coffee cause I didn’t want to get too wired. No sooner did I sit down and take a few sips when sure enough, Dean walked in. Again he had a pleasant smile on his face as he sat down and placed his satchel on the table.

While he waited for me to drink my coffee we talked about the new IKEA store. What I liked about Dean was that he didn’t appear to be rushed. He just sat back very calmly while we chatted and I told him all about the place. When I got down to about half-a-cup I said, “ Why don’t we get out of here, I think I have had enough of this place for today.”

Dean smiled and calmly replied, “OK, I’m ready whenever you are.”

We both got up and walked out the door. When we stepped out on the sidewalk, I felt a little odd in public with a man dressed in a business suit given I was wearing shorts, a tank-top and sandals. But my attire didn’t bother him a bit. He said, “Why don’t we walk back to my place, it’s only about half-a-mile”.

That was just fine by me cause I was still rather nervous and I wanted to get to know him better.

When we turned the corner, Dean began telling me about the art museum. I learned he volunteered his time on Sundays and actually worked there for a few hours collecting admission fees. He informed me that if I ever wanted to give my time, the museum would certainly welcome me given they were short handed.

The walk seemed to go by rather quickly. Before I knew it we reached his apartment building. He lived in a high-rise along the Gold Coast. As we got on the elevator to go up to his place which was on the 28 floor, he informed me that mostly single professionals lived in the building. After we walked in the door, he threw his keys on the table and fixed us a cold glass of iced tea. Then he invited me to sit on his sofa and pulled out a scrapbook of pictures he took on his recent trip to England. He wanted me to flip through the pages while he went into his bedroom and changed. The apartment was rather small, but no doubt his rent was expensive given the location and the impressive building itself.

As I flipped through the pictures, my mind was really a thousand miles away. No doubt we both wanted sex. The only question was, how was it going to happen. Was he going to go real slow, or was he just going to jump my bones. Surely a guy his age couldn’t wait to get it on with a young smooth teenager like me. The only question was, how was he going to go about it.

When he came back out into the den, he looked rather preppy. He was wearing a bright green Polo pullover, tan shorts and had on leather sandals just like me. He refilled our glasses of tea and then sat down right next to me as I continued looking over the pictures. Just as he began to explain each one, he gently placed his hand on my upper thigh. The simple touch of another male gave me an instant rush. It was the feeling I had been climbing the walls for after that night with Trent.