In my senior year of high school, I hung out regularly with four other guys. We were all a little nerdy and stuck to our friend group which was typical amongst all the less popular guys. However, all guys are the same when it comes down to being preoccupied with girls, sex, and of course our dicks.
One Saturday we were hiking out in the hills, and it did not take long for the conversation to turn to girls and sex. We started to brag about how big our dicks were. From what I remember, a couple of the guys were exaggerating for sure. It turned into good-natured teasing and arguments.
“Hey guys since we all think our dick is big, let’s compare them right now to see which one of us has the biggest dick,” I said.
Everyone was down and willing to show their dicks to each other until I said, “Give me a second while I search for a good porn to play on my phone to make us get hard.”
Everyone got quiet for a few seconds before the nervous laughter started. They were okay with showing their flaccid dicks but were very hesitant about having to get hard in front of each other.
I said, “C’mon guys, we’re all friends, right? So, what’s the big deal, it’s not like we haven’t seen each other naked already in the showers after gym class. I reminded them about the time, two of them took turns showing me your uncut dicks because it was the first time seeing one. If I am being honest, the only way to see who has the biggest dick is for us to be hard when we compare them to each other. Girls don’t want to know the size of your soft dick; they want to know how big it is when it’s hard.”
That seemed to ease the tension between us a little bit and we started looking for a spot. We found a little clearing that was both comfortable and secluded, off the trail and out of the view of would be passersby. We were all a little nervous and no one wanted to go first and quite a bit of time had already passed.
So, we did what most teenage boys did at our age, we started daring each other to take their dick out. After a few minutes we all were standing next to each other with our pants down and stroking ourselves while watching porn on my phone. We jerked off for ten minutes which was longer than we needed to get hard. Even though we were all straight guys I think we found it strangely exciting to expose ourselves like this to each other. Just like most guys our age, we got hard quickly. Two of us were already hard from just thinking about the situation because we were hard when we pulled our dicks out, but I think we all wanted to enjoy this session between us friends a little bit longer.
It was time to compare but we did not have a tape measure with us. I suggested we compared cocks for length and thickness by pressing them against each another. At the end of the day, it did not really matter all that much who the winner was because we were still young and growing. Today's winner might be tomorrow's loser, right? (I may not have been the biggest, but I surely wasn’t the smallest either)
After that day we continued to size each other up. We measured length and thickness and logged the results. We were obsessed with how much pubic hair some of guys had. And we always ended our sessions by jerking off and seeing how far we could shoot.
We watched lots of porn together while our parents were away from the house. The vaginal sex scenes were fun to watch. But the mind-blowing thing was seeing a girl suck a dude’s dick then watching her swallow it. Up until then, we had no idea if girls really did this kind of thing or was it only done in porn. We often wondered what it would feel like to have our dicks sucked.
In our awkward ways – we tried to get some girls at our school to suck us off. But no one would do it. Finally, we decided it was okay to suck each other off. We could not go off to college without any sexual experience and just had to know what a mouth felt like in comparison to our hands.
The rules were never to look at the guy blowing you because that would be gay. Instead, we would close our eyes and imagine our fantasy girl and we acted like we were speaking to them during the blowjob. A couple of the guys fantasized about cute cheerleaders at our school. Another one of the guys would always pretend his older sister was sucking his dick. As for me, I always thought about Ms. Wynn, the mother of one of the guys in our friend group. When he sucked me, I pretended it was Mrs. Wynn and would talk about my jerkoff fantasies about his mom and would shoot my load in his mouth when I could no longer take it.
This went on for the entire summer after we graduated high school and before we went off to college and our separate ways. We weren't doing anything gay, or so we told ourselves anyway. It sure beat hanging out at the food court in the mall to get our kicks or girls to talk to us. There was a line drawn when the subject of anal sex was brought up. We all decided that would definitely be too gay.
Would I do it again?
Well, this all happened a few years ago when we were younger and always horned up like most guys our age and yes, I would do it all again. I am the one who came up with the plan and put it in motion. Had it not been for my planning none of this would have taken place. When I was pretending that my fantasy girl was Ms. Wynn, I was really fantasizing about his older brother, which I finally confessed to after I came out to everyone three days before we were scheduled to leave for college.
What I did not know is they already knew I was gay. Shortly after our hiking trip one of the guys saw my browser history on my laptop when I left him alone in my room to use the restroom. Apparently, getting a blowjob by a guy was better than not getting one at all.
If you were to ask each of the guys about it today, their first reaction would be denial and shortly after my phone would be ringing asking why the fuck am I telling people about what happened. Off the record, they would all agree, we were having the time of our lives.
