The most thrilling night of my life, Part IV

For the last three weeks of summer, Dean and I got together another six times. Mostly I would meet him after work then we would then go up to his apartment and have some good old fashion hot gay sex. Afterwards I would catch the “L” back home usually just in time for dinner. I was even lucky enough to spend a Saturday night with him again and we had another great time. We fooled around in bed practically the whole day, watched some porno’s and then he took me out to a excellent Mexican restaurant later that evening.

When I got home on Sunday afternoon, I phoned my girlfriend Brittany. Since she wouldn’t break-up with me, I decided I had to end it. I came to the obvious conclusion that it wouldn’t be fair to either of us to continue the relationship.

So that night I took her out to our favorite burger joint and broke the news. Of course she took it really hard. But I assured Brittany it had nothing to do with her. I basically said that it all had to do with me, that I was changing, and it wouldn’t be fair to her to continue the relationship.

The next day when I told my parents, they were kind of heartbroken for they really liked her. They both said they didn’t think I would ever find a girl as good or sweet as Brittany. I shrugged my shoulders and said, “Well maybe.” I felt a little guilty for I thought to myself, “If only they knew, they would understand that I don’t want to find another girl better or sweeter than her. I want a hot juicy man.”

When school began, the days got shorter & colder. I only saw Dean if I was lucky maybe once a month. For the most part both us went back to our regular routines. I got involved in student council at school and Dean got involved in helping his bank buy out another bank down in South Bend, Indiana. But despite that, of course my mind was still on sex after having such a thrilling summer.

Over the next year, I had a grand time in my newfound lifestyle. Aside from Dean, I had three different ongoing encounters with three different guys. The way I saw it was that males, straight or gay, needed variety in their lives--especially at my young age. So I kind of wanted to fool around if I met someone that I liked and was as willing as me. Of the three encounters, one of them was kind of calculated by me, the other happened strictly by chance while the last & best took place by pure coincidence.

The first (the one that was calculated by me) happened one weekend in the fall when my dad asked me if I wanted to go with him up to Lake Geneva, Wisconsin from Friday night through Sunday. My dad was invited to a golf outing by one of his big customers. Normally my dad would occasionally take me and my brother whenever he was invited to one of these events if it was close by. Given the outing was only about 100 miles away and my dad would be driving up, he asked if I wanted to go along. My brother couldn’t make it because he had football practice and a big game that weekend.

At first, I informed him I would take a pass on the invite cause I had been with him plenty of times to Lake Geneva and there wasn’t anything to do in the fall other than to play golf, go hiking in the forest or hang out at the resort. While I played golf occasionally, it wasn’t one of my favorite things to do. But then my dad informed me that his good friend and fellow manager in their Milwaukee office, John Tales was bringing his son, John Jr. who was exactly the same age as me to the outing. My dad said that John Jr. and I could hang out together and play golf with them if we wanted, or just hang out back at the resort.

I had known John Jr. since we were kids. He and his family use to live in Chicago before his dad got transferred to the company’s Milwaukee office a few years back. The funny thing was, everyone in his family called him, Tuffy. But he was hardly anything but tuff. In fact he was the biggest sissy I had ever met. He spoke in a rather lispy voice and when he walked, he swung hips back & forth just like a girl. And at times when he and I were by ourselves-- like up in my room or his, he would wink at me especially when he talked over the phone to his so-called girlfriend, Rachel at the time which I thought was a big joke.

My brother and I once asked his grandmother at a company picnic how he got nicknamed, Tuffy. She explained that when Johnny was a little boy--like 4 or 5 years old-- he use to rip open his Christmas & birthday presents almost nonstop. So his grandfather once remarked when he was ripping away one Christmas morning that he was one “tuff” little guy and so the family nickname him that. After she finished, we did everything we could to keep ourselves from laughing.

Anyway I figured Tuffy had to be as queer as a three dollar bill by now and was probably as hot to trot as I was. And he certainly wasn’t a bad looking guy either. He was a little taller than me, about 5’8, 140 lbs. blond hair and captivating hazel eyes with a really firm and hairless body. In the summer he use to wear tight blue jean shorts and a half-cut tank-top which exposed his entire stomach and navel. It was almost as if he liked dolling himself up effeminately so he could show off his hairless and tight figure to his male friends--at least for me he did.

When my dad and I arrived at the resort early Friday evening, we drove straight up to the clubhouse for a large dinner party was being put on by my dad’s client. Just as we walked in the door, we were greeted my a number of his business associates and then were seated over at John and Tuffy’s table along with a number of other people. Right away I said hello to Tuffy and his dad.

After everyone exchanged greetings, Tuffy and I caught up on what we had been doing. I learned he was in student council like me and was trying out for the boys varsity tennis team. He also claimed that he was seeing this really hot looking girl, Mary, but I had my doubts.

While I was sure that if there really was a Mary, I was also sure she was his “girl friend” in a figurative sense rather than his “girlfriend” in a literal sense. I mean there was no way in hell I could see him making it with a female. But I sure as hell could see him with a hot cock in his mouth.

Just as dinner was served, I brought Tuffy up to speed on what I had been doing. I told him all about our family trip to Disneyworld that summer (except of course about my first time gay encounter with Trent). I added that I was in student council too and had even been appointed secretary since I could type better than practically anyone else. When he asked about my girlfriend Brittany, I informed him that I finally broke up with her (Tuffy had met Brittany several times and I always got the impression he was slightly jealous of her). He wanted to know why I ended the relationship so I kind of dropped a hint and said, “Well, I feel as though I have changed and am just not interested in girls right now”.

I didn’t know how he took my remark, but I figured it would at least open his mind and hopefully he might suspect something.

Before we knew it, dessert was being served. I chatted with my dad and Tuffy’s dad for a few minutes and then it seemed like all the men were suddenly smoking fine cigars and drinking brandy. This went on for quite a while so I began to tell Tuffy about my new friend, Dean I met one day over the summer at a coffee shop in downtown Chicago. While of course I left out the sex part of our relationship, I told him how we would hang out together, go to the beach and then out to dinner.

No doubt Tuffy was kind of surprised to learn that I had a friend who was so much older than me. But I added that older guys tend to make better friends for they are settled down in life and know what they want. I even went as far as to mention that I spent both a weekend and a Saturday night over at his place. As the conversation ended, I kindly asked him not mention Dean to my dad or anyone else for that fact because it was a secret that I only wanted to share with him. Now if that didn’t drop one hell of a hint, I didn’t know what would.

About an hour later, the party finally broke up. My dad and I headed for our suite and Tuffy & his dad headed for theirs. One thing that I liked about the resort was that it had suites rather than rooms. Each suite had it own kitchen, living room or den and two separate bedroom along with their own bathrooms. And one awesome amenity was that each suite had its own hot tube that was located between the two bedrooms.

The next morning I told Tuffy at breakfast that I really didn’t feel like playing golf. He looked at me, smiled, and said he really didn’t feel like playing either. I couldn’t imagine Tuffy being a golfer anyway with his effeminate like qualities and mannerisms. So we agreed to just hang out around the resort, watch TV, play cards and maybe do some hiking in the afternoon. I figured if ever the opportunity presented itself for some hot gay sex, it would be then for our dad’s would be gone for hours out on the golf course.