I once had a weird, but really hot encounter with my younger coworker
We both worked the night shit as delivery drivers for a pizza chain. That usually meant getting home between 4am~7am. We didn’t much life outside of work and sleep at this point, so the night shift people were semi-close.
My (23M, at the time) coworker (20M) was the first boy I had felt attracted to before and I didn’t know what to make of it. He had curly blonde hair and cheeks that were always rosy. He was also on the chubbier side, which tended to be my type with women as well.
Well, we were basically joking around during our closing/cleanup period about who at our store would likely sleep with who, and I joked that it would be him and I since we spend the most time together and he’s cute. We laughed and nobody thought much of it, at least it seemed to me.
After everyone had left, he and I were chatting as I approached my car. As I was slowly making moves to leave (Southern goodbyes, if you know you know), he gets a bit more serious and asks if I really though he was cute or if it was just for the bit. I stammered, but said something to the effect of “I mean, kind of both”. He held my gaze a little more intensely than was normal and said he thought I was attractive, too. I stared, unable to formulate a response to the situation I found myself in (I realize now probably also because it was 4/5 in the morning and I was sleep-deprived). In hindsight, it was a really awkward thing to do but I literally was short-circuiting: I reached out and took his hand and rubbed my thumb back and forth across it. We kept staring at each other for what felt like minutes, but thank god he eventually made a move to break the impasse.
He moved his face really close to mine, I flinched a little but moved back and we kissed. My brain was far too addled by the situation and lack of sleep to question how I felt about kissing a guy, all I knew was I liked it and I wanted him. One thing to know about me is I will absolutely not be the one to make a first move for fear of misinterpretation… but once the move is made, I will take charge.
I quickly pulled him to the back of my SUV and shove the back seat down to give us plenty of space, I shut the trunk door behind us and we quickly undressed. He laid on his back, legs wide, and arms outspread. I got on top, our dicks/balls sticking and rubbing together, his thighs wrapped around my waist. His body hair was ways softer than I expected. Again, I remind you that I had no experience with guys up to this point, but was so horny I wanted every bit of what was touching me.
Now the titular weird part. After so heavy groping and grinding and kissing, he stops and tells me to fuck his dick. The short circuiting of my brain continues, trying to understand. He doesn’t really give me a chance to figure it before he grabs my dick and pushes the tip against his. Important detail: he had a very small dick that stayed mostly flaccid. He grabs my hips and pulls/pushes to direct me. I’m so fucking confused and aroused, adrenaline flooding my system, that I just go along with it. I thrust in and out, his dick pushed inside him, and our balls slapping together. My senses were flooded with it all: the weird intercourse, his soft legs, his hands on my back, our tongues wrestling. I came harder than I ever had, coating his dick and balls, moaning into each other’s mouths.
I laid there for a bit to catch my breath before peeling myself off of him. The post-nut clarity hit incredibly hard. I dressed and grab napkins to clean him with before he also got dressed. After that night, we acted as usual. It took me time to figure out my sexuality after that, but I eventually decided I wouldn’t question what I do or don’t like or try to contain it with a label. He and I would occasionally makeout and grope in my car, but nothing else. We never really talked again after I got a new job. I did see him at the gas station years later, he seemed to recognize me. He had long hair then, and the feelings welled up again, but I just nodded to him.