This is an original story based on a real situation and real people in my past. Sadly, the sex is pure fiction. If you like my stories, please consider contributing to Nifty (https://donate.nifty.org/). Help them keep these stories alive.
Coming Out On Top
I held a variety of short term, crappy restaurant jobs, but I finally reached an age and level of experience where I managed to get hired as an assistant manager at a local pizza restaurant. The manager worked the lunch shift and then turned it over to me to manage the late shift. It didn't require any real skill, and it wasn't any less work. But I was old enough to serve beer and wine and apparently that also qualified me to wrangle a half dozen teenage employees.
The first part was fine. I really liked working the bar. People were always happy when you handed them booze and the only bad part was having to cut someone off when they overdid it. The wrangling part was okay too and I liked most of my crew. I wasn't a whole lot older, but I was old enough that they all accepted me as an authority figure. That is, everyone except Josh, and Josh was a little shit.
That's probably a bit harsh. He was a hard worker, and he even stepped in a couple times to help me usher out unruly drunks. But he had to be the most competitive person I have ever met, and for some reason I was the one he needed to beat.
Everything was a competition. How many garbage bags could you carry? How fast could you wipe down all the tables? We had customer comment cards and one stated that "the bartender has beautiful eyes" and even that, Josh had to claim as a win for him. A couple of the other kids had to remind him that he didn't work the bar, but he still wouldn't concede.
Like I said, everything was a competition. So, when Josh showed up to work in a really nice, if used, Chevy Nova, he started up with how cool his car was. He even blew a ton of money upgrading the stereo, and he wouldn't shut up about how "awesome" it was.
I drove a ten-year-old Volkswagen Beetle, so I knew his car was cooler than mine, and everything on my car was cheap and bodged together from whatever I could afford. It just happened that I had a halfway decent car stereo that I hooked up to an extra pair of home speakers, tucked in behind the back seat. I wasn't too surprised when Josh demanded that we compare sound systems. It was a stupid thing to compete over, but that's just how he was wired. So, I acted like I was reluctant, but I knew had a surprise for him.
There was still some work to do, but we had closed down for the night, and everyone had come outside to witness the competition. Josh cranked up his expensive stereo and then stood there, arms crossed, grinning, and waiting for me to admit defeat. I made a show of reluctantly clicking on my stereo and then gradually upping the volume. As the volume rose and began to overwhelm what was coming out of Josh's car, the crowd of kids all started to cheer. You could see Josh physically deflate as my homemade sound system beat out his fancy, overpriced stereo.
When the novelty wore off, everyone else took off, but Josh was scheduled to help me with the final clean and lockdown, which meant it would be the two of us left to close the place up. I wasn't sure how that was going to work go, so I just tried to act like it was no big deal.
Back inside. I went to the office to count the tills and get the deposit ready for the morning manager, while Josh was tossing out the garbage and doing a final wipe down. I could hear him banging garbage cans and swearing every so often, so I knew he was still steaming about what had happened.
I was putting the money bags in the safe, ready to help Josh finish his work, and I looked up and saw him standing just inside the office doorway.
"Hey Josh! You finished already?" I asked, hoping to cool the waters. "Nice job."
"Yeah, thanks." He grunted. He didn't move. "I bet I have a bigger dick."
I knew I hadn't heard that right. "What's that?"
"I said, I bet my dick is bigger than yours."
Okay, I guess I had.
"Fuck, dude! It's just a car stereo! I got lucky that my speakers worked out like that."
"Are you afraid?"
"Of what? Are you kidding?"
"I bet mine is bigger."
I was getting pissed. "I don't fucking care, Josh. So, what if it is?"
"I can prove it!"
Was this high school punk actually challenging me to a big dick contest? I was about a head taller, so I was pretty sure he was full of shit, but it was just such a stupid thing to do.
"You're fucking nuts."
"C'mon..." He sounded like he was pleading now. "You beat me at everything else... You can't let me have this one thing?"
"Whatever dude. If you want to believe that your dick is bigger than mine, then so be it."
"No! I want to prove it!"
"Why?"
He looked deflated. "I don't want you to think I'm a loser."
"Oh... hey... I don't think that..." Actually, I sort of did.
"Then bet me."
"What? What are we even betting?" I asked, still annoyed.
He pondered his answer. "If I lose, I'll clean the grease pit every night for a month."
Everyone hated that job, and they hated me when I assigned it. So, it was actually a hell of an offer.
"Okay, but what do you get if you win? I can't make other people do your work."
"I don't want that." There was a long pause that made me wonder if he might be backing out. But then he blurted it out. "I really need to fuck somebody."
I shrugged. "So go hook up with one of the girls. I don't see how I can help."
He shook his head. "All the girls think I'm a jerk."
"Whose fault is that?"
"I know but... it doesn't have... to be a girl."
"Well, sure but..." The lightbulb suddenly flicked on. "Oh! No way! You're not serious."
He gave me a crooked smile. "Why not?"
"Well, for starters... I'm not gay!" I challenged. "And though I doubt you've ever seen one, all I ever hear you talk about is pussy. So, I assume you're not either."
"No," he agreed, "but I am still a virgin... and I'm horny... and I know you won't tell anyone... and I know you're not getting any."
This was a whole new level of crazy for Josh, but it was at least based on fact. I remembered what it was like when I was his age, virgin, and I was fucking my pillow every night. Any tight hole would have been better than that. He was also right about my sex life. While I wasn't a virgin anymore, I could barely even remember the last time I had sex.
I was always broke so I never went out and the only girls I knew were at work. They were all young enough to get me in real trouble. Besides... I would probably win. Right?
"Screw it. Fine. It's a bet." I sounded confident. I'm not sure that I was. Even if I expected to win, there had to be at least a sliver of willingness to accept the consequences of losing. A shiver ran up my spine as I considered that.
"Should we do it right here?" Josh asked.
The office felt tiny and cramped. I decided we could use the banquet room instead. It was blocked off from the exterior windows, so we would have privacy and some time to react if anyone came in. It wasn't likely to happen, but the manager would sometimes show up, and I didn't want to risk it.
The banquet room was lined with padded bench seats, and all the loose chairs and tables were piled at one end of the room until they were needed. This gave us some open space for the competition.
I wasn't too sure how to even go about it, but Josh completely stripped off his slacks, so I figured I could do the same. Then we stood facing each other and I actually breathed a sigh of relief when I saw that our dicks were pretty close in size, if still soft.
Josh started slowly stroking his cock, and I figured I better do the same or it wouldn't be much of a competition. As weird as this was, it was also kind of hot. We were both getting harder, and given the circumstances, it was happening easier than I expected. I was actually into watching this punk kid stroke his rod. Except...
We both grew at about the same pace and I was pretty satisfied with the hardon I had on display, but... after I hit full erection, I could see that Josh's dick was still filling out. In my head I kept telling myself that was just a matter of perspective. He was shorted than I was, so naturally his dick would look bigger by comparison.
Josh finally seemed happy with his results, and he stepped closer so we could match them up. I had been right about perspective, but only to a point. His dick did look big compared to his shorter body, but it also looked big compared to mine. It wasn't a huge difference, but it was enough bigger that I couldn't pretend any different.
Josh was elated. "I don't have to clean the grease pit."
"You still have to clean it when you get scheduled for it." I reminded him.
"Yeah, sure," he admitted, "but I still would have kept my deal if I lost."
He didn't have to say it outright. He was challenging me not to back out on the deal. In truth, my mind had been shifting back and forth between being terrified I might lose and wondering what it be like if I did. I wasn't even sure if I could make it work, and as I stared at his cock I wasn't getting any more confident about it. But I was hard... and I was horny.
"Oh, shit..."
"What?" He asked.
"I should have brought something for lube." I explained. "I didn't even think about that. I just assumed... I wouldn't lose."
"Be right back."
Josh dashed, half-naked, through the darkened restaurant, fully exposed to anyone who might look in the windows. He disappeared into the kitchen and was only there for a few seconds before he raced back and proudly showed me a paper towel holding a thick glob of shortening.
"Yeah... I guess that will work." I admitted. I looked around the room. "How do we do this?"
"Maybe you can lay down on the bench."
At least it would be padded. "Okay, but... you need to go easy. I never did this before."
Josh suddenly looked every bit the high school kid. "Oh, I will! I promise! I will make it so good for you!"
He was so sincere, and grinning like a kid at Christmas. It made me smile, even knowing I was about to let this happy kid shove his oversized pecker up my poop chute.
The bench seat chilled my skin as I stretched out on my stomach. The seat wasn't very deep, so my outside leg was inclined to slip off the edge, leaving me in a position that felt incredibly exposed.
I looked over my shoulder and saw Josh slicking his shaft with the vegetable grease. That was too scary, so I just dropped my head into my arms and waited.
A few seconds later I felt the cushion compress as Josh knelt between my legs. Then I felt a slick finger prod my butt pucker. He was so gentle. Maybe even a little afraid of pushing inside.
"It's okay." I told him. "Just push it in slowly. You'll need to loosen me up."
"Okay... I promise. I'll be careful." The tip of a lubed finger began to ease inside of me.
That was something new. I would give myself a thorough scrub during showers, but this was blazing whole new trails. It wasn't at all unpleasant, but it was totally unnerving. My sphincter couldn't decide if it was supposed to tighten, loosen, or push out the intruder. It mostly just trembled and fluttered and sent shockwaves straight to my nuts. Very interesting.
"That looks so cool."
In spite of the finger tickling my guts, I had sort of forgotten I wasn't alone, and his voice in the empty restaurant made me jump, pulling me out of my stupor. At the same time, the probing finger was abruptly pulled out of my anus. It felt like the soft muscle was trying to nip at the withdrawing digit. Very interesting, indeed.
"Can I do it?" He was giving me a choice, but I had already reached a point where there was no other choice.
"Yeah... you can do it."
Josh shifted his weight forward and I felt the blunt, soft knob of his cock push between my buttocks and against the still nipping rosebud. The difference between his finger and his dick were immediately obvious and there was a brief flash of my earlier reluctance. Thankfully it passed.
He never really pushed, just letting the head nestle in my crack while my body decided what to do with it. Much to my surprise, it made up its mind quicker than I expected, and the previously tight muscle relaxed to let him in.
It seemed like it was going in pretty easily, but then I realized that there were a couple layers of resistance, and even when I knew he was partly inside me, there was still a barrier that was not quite ready to let him all the way in.
I have to give the kid some credit. I would have probably shoved in by then, but he held perfectly still. Well, not perfectly still. I began to realize that his body was shaking, either from excitement or tension, or both. He was desperately struggling to hold back, and I could tell how much he needed this to happen.
Pleasing Josh had never been up at top of my list, but it was now. I knew that this experience would have a huge impact on him, and I was starting to consider the impact it could have on me. I was determined to do it. I pushed back.
At first his cock head seemed to flatten against the reluctant muscle but then, suddenly, it popped through, and the full length of his cock slid into me.
"Oh fuck... oh fuck... oh fuck..."
Looking back, I still can't remember if that was him or me. Maybe it was both of us.
Almost on instinct, Josh began to fuck my hole. At first it was slow short strokes, but gradually he built up speed and length until he was literally hammering into me.
I knew this would be different. Whether I was jacking off or even back when I actually had sex, my prick was always the primary focus. It was the source of all the good feelings, and I assumed I would need to jack off to get anything out of this. I assumed getting fucked might be tolerable, maybe even pleasant, but it was so much more than that. Each stroke through my bowels, felt like a mini orgasm, and I knew if I even toughed my cock, I would blow.
My cock was jammed uncomfortably against the bench seat, and I didn't even care. I knew if he fucked me long enough, I was going to cum, just from that. I hoped he could fuck me that long. I wanted to know what that would feel like. I even hoped he could fuck me even longer than that. I wanted to feel like this forever.
The little shit was proving to be an amazing stud. The girls who had all dismissed him had no idea what they were missing. I was fairly certain I would still get annoyed with Josh when he went back to his usual antics, but I also knew I would let up up my ass anytime and anyplace he wanted it.
Quicker than I expected we reached my first goal. Josh was stroking into me, and my body went rigid, my ass clamping down hard on his shaft. I was cumming and it was explosive. I can't remember ever cumming that hard before.
It then looked like I wouldn't make my second goal. The clenching of my sphincter was too much for Josh, and he rammed into me one last time, flooding my guts with teen spooge.
We both trembled and shook with the throes of orgasm, eventually settling down, with me stretched out on the bench seat, and Josh draped across my back. Our breathing was ragged.
"Thanks... thank you." Josh gasped.
I had to chuckle. "Thank you!" I told him. "That was way better than I expected."
"Really?"
"Oh, yeah."
I felt his cock pulse inside me.
"Can we do it again?"
"Um... yeah! I'd like that. Maybe next time you're on late shift..."
"I mean now."
His cock pulsed again, and I realized it was getting harder, and then he was starting to move inside me.
"Are you serious?"
I bet I could fuck you all night long!"
I guess wishes do come true.