The most thrilling night of my life, Part IV

After we both took dumbs to relieve our fudged packed selves, we got in the shower together like the good gay boys we were. Once we washed and cleaned our cocks & holes we hopped in the hot tube. For the next half-an-hour, we kissed and felt each other’s bodies. I knew he was in love with me given our long friendship and the hot sex we just had. Then I sat up on the edge of the tube and let him suck me off. Of course after I came in his mouth, we switched positions and I sucked him off.

For most of the day we laid naked in bed together, talked and watched a couple of movies. I learned from him which I suspected all along that his so called girlfriend Mary was in fact a friend only. He was actually seeing guy he met of all places at church named, Marty. But Tuffy boosted my ego when he said he didn’t love him half as much as he loved me.

When I told him about my first gay encounter with Trent on our family trip to Disneyworld, he thought that was the hottest gay experience he ever heard. But he was definitely surprised and kind of jealous I think to learn that older guys like Trent & Dean were really more my type. He asked with genuine curiosity why I liked older guys so much. I really didn’t know how to answer his question other than to say that mature men kind of aroused me. Perceiving his enviousness I didn’t want to make him feel like he was playing second fiddle to Trent or Dean. So I rolled him over on his stomach, spread his legs and gave that sweet hot pink hole of his an extraordinary rim job. I knew that made him feel more secure about our long standing friendship.

After we watched the second movie, we went for a short walk together and talked some more about our sexual desires and what turned us on. I was a little more careful this time about what I said. I certainly didn’t want to say anything that might make him feel inferior. Just about the time we got back and looked out the window the men were driving in after finishing their golf round.

That night at dinner I was seated next to Tuffy’s father and Tuffy was seated next to my dad. While I thought the seating arrangement was rather odd (almost like I was sitting next to my father-in-law and Tuffy was sitting with his after our hot fuck session that afternoon), nevertheless less I went along with it. I was sure Tuffy found it unusual as well, but he didn’t say anything either. It wasn’t but a few minutes later when I looked across the table and noticed that Tuffy and my dad were involved in what looked like a heavy conversation. No sooner were they talking when Tuffy’s dad asked me what we did while they were out playing golf. Well I sure as hell wasn’t going to tell him the truth in that I fucked his son right in the ass and then I let him fuck me. So I just said that we hung out and watched TV. Then he and I went into a long conversation about Chicago and just how much he and his family missed living there.

The next morning I decided I better play a round of golf with my dad cause I wanted him to think that I really enjoyed these little outings he invited me to. Tuffy did likewise and played with his father and two other guys who were paired with them. We teed off very early that morning because we had to finish by noon so everyone could eat lunch, pack and then depart.

After we finished 18 holes, Tuffy and I passed on lunch. We figured we had about an hour to fool around again before lunch was over. This time we headed over to his suite where we quickly stripped, fooled around in bed for a few minutes and then fucked one another again. After we took a quick shower and got dressed we even had enough time to down a burger & fries over at the club house before the luncheon was over.

Just as we were getting ready to leave, Tuffy and I agreed to make it to the spring outing in May. My dad and Tuffy’s thought that was a great idea given we enjoyed each other’s company. I thought to myself, “Boy if our parents only knew how much Tuffy and I enjoyed each other’s company while they were out playing golf, I think they would have both been stroked out.”

One the drive back to Chicago my dad and I talked about what a great outing we had that weekend. And while I certainly enjoyed the hot sex with Tuffy, nevertheless he couldn’t fully satisfy my urges the way men did. I mean I knew almost from the moment I sucked both Trent and Dean off that guys like them really turned me on. I guess Tuffy reminded me more or less of being with a female. But I sure did think he made a fine substitute when no one else was available.

My next encounter happened by chance right after the new year. I was sitting in our family study on a freezing Sunday morning just after e-mailing our vice-principle the typed minutes from our first student council meeting of the second semester. I thought I would fool around on the Internet for a few minutes given everyone else was still asleep and check out a few chatrooms. I hadn’t been into a chat in eons, so I clicked on the list to view the various rooms to see if any of them peeked my interest. Of course by now I wasn’t interested in the straight ones anymore, so I immediately moved my cursor over to the gay list.

After I scrolled up and down a couple of times, I noticed one that said,
“ GayMensChicago.” Naturally, it got my attention, so I clicked into the room. The chat had about 30 or more people in it, therefore it was kind of difficult to the follow the dialogue given so many conversations were taking place all at one time.

Once I got hit with a flood of instant messages asking the usual stupid questions like my cock size, top or bottom, into younger or older, my age ect. ect., I was just about to click out when I got a private message that said, “Hi” from someone named, “SkidooEngland”. I thought about whether I should answer the IM for about thirty seconds given I figured whoever it was, was probably half-way around the world anyway. But I finally decided to reply given I was in a courteous mood that morning to anyone who was at least respectful of me. So I typed, “HI” and sent it. Within a few seconds the person replied back introducing himself as, Ian.

After I introduced myself as Collin, he didn’t go right into talking about sex like most everyone did in cyberspace. Instead I thought it was kind of cute when he asked if I had my wool socks on cause it was so damn cold outside. I replied that I did and ask if he had his on as well. He IMed me back and replied that he sure did even though he was in a nice warm hotel room. But he added that he still had trouble keeping his feet warm. When I asked what he was doing in a hotel room, he IMed me back and said that his company over in England had sent him across the pond to their Chicago office for a twelve week course in American accounting standards and methods.

When I asked if he liked the course, he replied that it was very challenging and felt like pulling his hair out at times. He also added that the freezing cold weather did help matters for he couldn’t even go outside and take a nice long walk to clear his head. I laughed and replied back, “That’s how Chicago is in the winter.”

Before I knew it we were talking about everything from the weather, to our families, to my school, all about his job and our hobbies. I found Ian to be a rather interesting guy. He was originally from Chester, England, grew up in a large family of 4 brothers, 2 half brothers and two sisters. He worked in the steel industry as a corporate account, was 33 and came out to his family when he was 28. Of course I told him that I was a student, was still closeted, and was thinking of working in computer programming when I got out of school. I could tell by the way he wrote that he was certainly a professional kind of guy who was hardly looking to have sex with just anyone.

At one point during our conversation he told me that after being in Chicago for about a month he missed his family & friends more than anything. He went on to say that he would just about give anything to go out to lunch or dinner with someone-- anyone--for that fact for he was lonely and just wanted some company. Needless to say, I could certainly relate to the circumstances he was in. I mean I knew how I would have felt if I were sent out of the country for twelve weeks and didn’t know anyone. No doubt I would feel exactly the same way he did.

Just about the time he was getting ready to sign off and thanked me for chatting with him, out of curiosity I asked where he was staying. He replied that he wasn’t right in the downtown area, but was up on the north side of town. I quickly replied that I lived on the north side as well. He then quickly replied, “Really?”

I replied, “Yea Really.”

When I asked what hotel he was staying at, he said that I probably wouldn’t know the name cause it was a really small place that his company contracted with to house their employees on long term stays. But he told me he was staying at the Lincoln Gardens Hotel.

Well I knew exactly where his hotel was---it was right across the street from the mall where JC Penny was located--the very same store that I bought the sexy zebra briefs to wear for Dean the first time I spent the night with him.

I quickly replied that I knew exactly where his hotel was and that it was only about a mile from my house. He replied, “Are you kidding ?”

I replied, “ No, not at all,” and that it was right across the street from JC Penny. He eagerly replied , “Yea exactly --I was just there yesterday and bought a few shirts---wow---small world isn’t it”.

I replied, “Yea, it sure is.”

Then he IMed me and said, “Well Collin, I better get going---I’m going to study for a while and then I think I’ll go over to the mall and get a burger or something”.