The town I grew up in was quintessential “Connecticut” complete with a big white Congregational Church, as well as a large town green lined with small local shops and tall century old oak trees with yellow ribbons around the trunks (we were still in the early days of the second gulf war). It really was a bucolic place to grow up.
Our town had one of the larger lakes in the state, it was spring fed so the water was always clear and cool. The lake, had homes all around it with docks.
My best friend at the time, we will call him Andy, had a house on the lake. It was a large beautiful craftsman style house built by his parents. Andy had his own “suite” in the basement with outdoor access to the lake and dock. We spent many days and nights out there growing up.
I had known Andy my whole life, as our parents were close friends. We were both 19 at the time of this story, but there was a lot of life lived together as friends before this story.
Andy’s father had died suddenly when we were both young and my parents insisted that I spend every moment of free time with him to help him through the grieving process. We did everything together, he was like a brother (I loved him like a brother too), and his mom was like a second mother to me. We had a lot of fun in our younger years swimming, going on vacation together, skiing at the local mountain, and most fun of all spending time out on the boat when we were old enough to drive it.
Fast forward to our senior year of high school. Again, when we were both 19. It was the last few weeks of summer before I went to college up in northern Vermont. I spent almost every day with Andy that summer.
I had always been attracted to Andy, but I thought he was straight. He always had a multiple “girlfriends” at the same time, he was honestly a true player. This was something that I always envied and never had the balls to do myself lol.
I myself knew I was gay since the late nineties (damn Justin Timberlake!) but I was very much in the closet and at that time saw no route out of the closet.
In high school I was a short Italian guy 5’6”, with a buzz cut, always well dressed in prep attire (voted best dressed in high school). I had a shy demeanor at the time but knew I was attractive as many girls swooned after me. I, unlike Andy never took the bait because I knew I had no interest in women and it wouldn’t work so I resisted any of those advances.
I didn’t play team sports but was an avid, lifelong skier with thick tree trunk thighs and a strong core. You could call me beefy but not fat.
Andy was taller than me with longer crew cut brown hair, a chiseled face with deep blue eyes. He tended to dress a little more “urban” than I with straight rimmed baseball hats and oversized basketball jerseys with timberlands. He had the inklings of a six pack and bulging muscles from his years of working out, playing basketball, and training to be a mechanic after high school.
I was taking a more white collar route; I worked on a few political campaigns in my late high school years and was going to school for international relations and politics at UVM.
Our first sexual encounter occurred during our senior year of high school. I was staying at Andy’s house and we were drinking, ultimately straight porn came on and we both jacked off together in the same room. It was hot as all hell. We had seen each other naked many times but this was the most “sexual” we had ever been together. This happened a few more times over the school year but nothing else ever happened and it didn’t turn into anything else during the school year.
That was until that last week of summer before I left for college. I was hanging out at Andy’s house, we had been in the boat all day, smoking a few blunts and listening to Tom Petty and Creedence Clearwater with a few of his neighbors. It was a wonderful day and by the time we made it back to the dock the sun was going down and we were both exhausted and very stoned.
Andy’s neighbors walked through the woods back to their house and we went inside and cracked some bud lights and went down to Andy’s room which was basically like an in-law suite. He had the whole floor to himself.
We chatted for a bit, talked about how the upcoming year was going to be weird since I was going to college while he stayed back in town to work. Andy kept saying he was going to miss me and this summer. I could see true sadness in his eyes. He quickly changed the subject to his girlfriend at the time and we stared talking about sex. Out came the pictures, which then led to him showing me a porn video of something he said he always wanted to do.
The video was of a man with a large dick facefucking a beautiful woman. He said his current girlfriend would never let him do that. It then took a surprising turn, he said “I just love watching guys shoot cum out on someone’s face”. He then said “often times when I watch porn alone I fast forward through all the fake moaning just to see the money shot” “it really gets me going” he sighed.
When we watched porn together we always watched through the whole thing and he never looked at me. His eyes were always glued to the screen and the vibe he gave off was totally straight. Unlike me!
The surprises kept coming however. He whipped out his thick 7in cock and said I have another one to show you, I felt my dick start to grow in my bathing suit. He put on another video on his laptop, this one had two guys and a woman. He fast forwarded about half way through and the two guys were standing in front of the woman’s face. One guy grabbed the other guys dick and finished him to completion on her face. Andy then said “that’s so fucking hot I’ve always wanted to try that too”.
I now had a raging hard on and knew something was about to happen. He said “don’t be shy man whip it out, let’s get off”. I obliged and pulled my bathing suit off.
My summer tan lines were intense and my black Italian pubes were all bushy from a day of swimming. My 6in dick was standing at full attention. He looked right at me with his deep blue eyes and said “can I touch it”? I responded “of course, I have been waiting for this moment for a long time”. “Really?” Andy said, “why didn’t you say anything, I have been trying to make this happen all year”. With that he reached out and grabbed my dick, he told me to sit down. I sat on the edge of the futon in his room and he started to jerk me off, he then grabbed my hand and put it on his throbbing cock. He moaned loudly.
Andy then stood up bent over and gave me a big kiss and said “I love you man, I have for a long time, I’m really going to miss you”. I saw his eyes well up a little. I leaned into Andy and kissed him back, “I love you too man” I said back. We kept making out rather intensely.
Andy then told me to stand up, he got on his knees and said “I want to be like one of those girls in the video we watched”. He started sucking on my dick again. He started slowly and then started to deep throat it until he gagged with his nose buried in my musky, sweaty bush.
I grabbed his head and guided him up and down on my cock, increasing his speed. I could tell he was new to this and needed some guidance. I knew I was getting closer and closer. He had one hand on my thigh and another on my ass and he was pulling me deep into his throat. It was honestly one of the best blowjobs I had ever had, even to this day.
At this point, I started to get that familiar twinge in my nuts reminding me I was at the point of no return. I gasped and said “I’m really close”. He pulled my dick out and said “rub it out on my face bud”. I furiously started to rub my dick as he licked the tip. A few seconds later my dick erupted a multi-day load right on his face. Three thick ropes spread from his lips to his eyes. I collapsed onto the futon.
He took some of my cum off his face and started to jerk himself off and within a minute he also came on the floor. As he was cumming he leaned in and kissed me, I could taste my salty cum on his lips. He then said “that was the most amazing experience” he grabbed his t-shirt wiped off my cock, then he wiped his face. He got on the futon with me and we cuddled, spooned, and fell asleep within minutes.
I woke up the next morning and had to go to work driving delivery to pay for books. We quickly showered together and he walked me to my car. I was leaving in two days for Vermont. It was bittersweet as I knew things were going to change in my absence.
As I turned on the car, I rolled the window down. He poked his head in gave me a big kiss on my cheek and said “don’t forget about me up there in Vermont, we have something special”. I responded “I wont forget about this, you can always come up and visit and ski as well” he nodded and waived me off. I drove away, with one of the most warm and satisfying feelings I’ve ever had.
