Mark and I had been friends since I moved into town in the sixth grade. We were both kind of jock types while being sports hating goths at the same time. Weird combination, I know, but it worked for us. I had always been the "experienced one" in our friends group because...well...I essentially lied about my past in my hometown. As far as anyone knew, I had lost my virginity in the fifth grade to my ex girlfriend. This, in a serpentine kind of way, lead up to my actually losing my virginity in the seventh grade to my then girlfriend. NBD if you've already lost it, right?
As a result of being so sexually charged at such a young age, I found myself curious about everything. I have distinct memories of fingering my own ass while I jerked off before I could even cum. The rare instances that I stumbled across porn (this was the 90s) I remember obsessing over the dicks. Not the dude or his body, just the dick. Which leads me back to Mark.
On the afternoon of seeing and feeling my first cock, Mark had come over and we were doing typical American teen bullshit. Joking about drugs, lighting incense in new and exciting ways, talking about girls we wanted to fuck. The conversation, as I'm sure you're expecting, turned almost directly to sex every time Mark and I hung out.
On this particular occasion, however, we found ourselves beating around the bush about our jerking off techniques (yass pun). I remember my dick, which I now know is relatively big at 7", growing rock hard in my blue cords as Mark described his approach to stroking his dick. I'm just now realizing I haven't introduced myself. My name is Mike (fake). Why did I introduce myself and immediately tell you it's a fake name? Because you're a slut for making it this far in the story.
Anywho, remember what I said at the beginning about Mark and I being goth/jocks? Here's what you end up with: I had brown hair down to my shoulders, an 8 pack, and was ripped overall. Around 5'5" at the time Mark was a full head taller than me, again, ripped out of his mind, and had the typical mid-part hairstyle and brown hair as well.
We were both hot as fuck.
So back to the scene, my dick is straining my blue corduroy pants, wondering why Mark describing jerking off made me so horny. I suggested, in 7th grade logic, that we jerk off to see who cums faster based on their technique. Mark finds this a grand idea and proceeds to reach into his black khakis to get himself going. Not to be outdone, I do the same.
I closed my eyes and tried to picture "straight things" and found myself thinking "his dick is right there" over and over. This sent me over the edge in, what felt like, 30 seconds. This also did nothing for how horny I was.
Mark hadn't come yet so he asked if I'd like to watch. I nodded so he laid down next to me in my bed (lower bunk) and started beating off but inside his pants. I jokingly suggested that maybe he'd like some help. He nodded. I wasn't prepared for this. I was just joking! He pulled the waistband of his boxers up and held it there. I will never forget this moment as the one when I decided to jerk a cock for the first time.
I reached into Mark's pants and grabbed his dick. I felt so threatened as I realized how big he was. I couldn't get my hand all the way around it and, in my awe, started tugging on the thing like an idiot. He allowed me my shameful attempt at jerking him off for a little while but eventually pulled my hand away and finally pulled his magnificent cock out of his silk boxers (again...90s). I laid on the bed, mesmerized by his dick, and came again as I watched someone dump a load on their stomach for the first time.
Mark and I continued to give each other a bisexual complex for the next year. I still jerk off thinking about sucking his dick and regret never begging him to fuck my ass although I did ask politely. Maybe these are stories for another day...