Note: Doing another story from highschool (HS) (both of us were 18). If you want to hear more or ask anything, feel free to message me. Read some of my other stories on my page. Again, my stories are based off memories of things that happened to me, there’s some stylized additions to add to the entertainment that connects dots. Enjoy!
Since middle school, I had been the only out gay kid and HS was no different. During my senior year, I was semi bummed out I couldn’t ask another gay guy so I decided and told all my friends that since I couldn’t go with a guy, I’d rather go as a group. My friends all agreed. However, on a random day, I noticed suspicious things around my friends. I shrugged it off as nothing, mostly because I had other stuff to focus on.
But later that day, I walked into my class to my straight best friend (let’s use the fake name Franco) with flowers, candy, a stuffed bear, and a sign. I’m my head, I imagined he was promposing to someone else, so I looked around but realized he was walking to me. I had second thoughts but said yes.
The day of our prom was interesting. He had explained that he wanted someone to be a gentleman and take me out the right way but to not get the wrong idea. I would laugh because eventhough I knew it would never happen, I sort of had a puppy crush on him.
We spent the time before prom going to eat at a French restaurant, he got me flowers, and we then went to a nice park to take scenic pictures.
Prom was fun but ended around 10pm. Everyone split off into their own groups. We went out with some mutual friends to eat and celebrate our friends winning prom king and queen. After we ate, he asked if he could take me somewhere nice. I of course said yes. Imagine my confusion when he drove us to our highschool campus (It was close to a forest and nature trail). He drove deeper into the back of the school into a rocky trail where we finally got to an empty parking lot that overlooked a nice pond. He began telling me about memories he had here and memories he had with his ex.
We both went to the back of his truck and opened the back and set out the blankets he had there. We laid down and looked at the stars.
Me: so what would you and your ex do here?
Him: we’d watch the stars and makeout, sometimes fuck.
Me:out in the open? I knew you were horny but damn.
He laughed but then got serious. I knew his recent ex was a sensitive spot but he would always laugh. He got up and turned to me.
Him: can I be honest?
Me: sure, what’s up dude?
Him: my girlfriend broke up with me because she said I was too small
Me: small? Like short? Aren’t you like 5’9?
Franco was 5’9, Mexican with bouncy/wavy black hair. He had a small mole under his eye that I found cute. His skin was tanned and well taken care of. He’d always been into being fit but never played any sports. You could clearly see his round pecs in every shirt he wore as it stretched it out and his tree trunk legs in all of his pants.
Him: no, like she said my dick was small. She cheated on me and said the other guy was bigger.
Me: damn dude… I’m sorry.
I proceeded to hug him and he sighed. He told me the story of what happened and he laid on my shoulder as I played with his hair.
Me: well, fuck her. She doesn’t know what she’s missing out on. You probably have a nice ass dick and she’s out there probably getting STDs when she could be making a good man like you happy
He laughed and thanked me.
Me: plus, I doubt you’re actually small dude. You give off the energy of someone who’s got a good sized dick
He didn’t laugh this time. He just stayed serious, like if he was thinking.
Him: can you help me measure it?
I hadn’t ever thought it would lead to this but I wasn’t about to let this opportunity pass.
Me: sure dude, how can I help?
Him: help me find my tape measure and watch porn with me. I don’t want to be the only one jacking off
We went about his dad’s tool box in his truck and found a yellow flexible tape measure. He pulled out his phone and we both sat there as he started to play porn. He always mentioned being into dominant things so it was interesting to see him put on porn of a woman getting absolutely destroyed by a big cock. I could sense that both of us got hard. I looked at him but he wasn’t yet stroking and I could sense he was waiting for me to start. I began to slowly rub my own dick over my suit pants and took off my jacket. He did the same.
We both unzipped our pants at the same time and took out our hard cocks. You could feel the steam rising from our dicks due to all of the dancing we had just done. After a couple minutes, we were both fully naked. Our arms were rubbing up against each other as we continue to jerk off to the sledgehammer type fucking in the porn. Both of our heavy low groans were becoming intertwined while the low buzz of the forest around us continued.
I looked over to Franco.
Me: do you want me to measure it now, before we cum?
Him: yeah sure
He stopped and laid back, catching his breath. Leaned over him to get the tape measure, feeling the warmth of his body as I rustled through his clothes. I jumped slightly as I was startled by his hand tracing the center of my back.
Me: what’s up?
Him: nothing, sorry, you just looked very nice under the moonlight.
(God I wanted to suck the skin off his dick right there but I chuckled and felt myself turn red)
I got on my knees and placed the tape measure around his dick.
Me: do you mind if I grab it?
He laughed and gave me the go ahead. I grabbed his dick by the base and moved the measuring tape from his shaft along the upwards curve of his dick. I then measured around the thickets part of his shaft.
Me: hey, i don’t think you’re small, you’re bigger than me, 6.75 inches long and 5.1 inches in girth. Dude you’re decently big. I don’t know what’s wrong with her tbh.
To be continued in next part