This is an original story (M/M, anal sex) based on a real situation and real people in my past. Sadly, the sex is all pure fiction. If you like my stories, please consider contributing to Nifty (https://donate.nifty.org/). Help them keep these stories alive.
Sub-Contracting
When I finished college, I wasn't having much luck finding work. My degree wasn't doing me any good. It was a recession, and jobs were hard to come by but luckily, I had a friend who was moving on from a construction gig he had, and he told the owner that he knew someone who could take his place.
I was hired without an interview, which was a good thing because I had no real experience, but I learned that the owner was just happy to have someone apply who didn't have a criminal record.
The construction occurred in phases, and I would follow about a week behind the framers and window installers, and I would put up siding and exterior trims. I was reasonably handy, but I had never done this work before. I was glad for the week of overlap with my friend where he could show me the basics, but it wasn't rocket science and I managed to pick up enough from him to fake it until I got more experienced.
There was so much turnover of crew, it didn't take very long before I was made crew chief on most of my jobs. The work was mostly seasonal, and there were long stretches with little or no income, so guys would come and go, chasing work wherever they could find it, but there was usually enough work to keep at least one or two people semi-busy. If I saved up during the busy period, I found I could pay the bills and get through the slowdowns. I wasn't getting rich, but I was getting by.
I had been at it for a couple years, and on my second year, after the winter slowdown, for some reason it was taking longer than usual for work to pick up. It was mid-summer before we finally got a really decent paying job, siding a massive new apartment complex. I had one other guy, Kenny, I had been working with on a bunch of small jobs, but the boss needed two new hires for the apartment project.
The two new guys, Ted, and Bobby were typical of the kinds of guys who gravitated to this kind of work. They both looked underfed, like they went stretches without a regular meal. Ted was especially rough looking, like he had been through some hard times, but he knew his stuff and was a pretty good worker. Bobby was a fresh-faced kid who looked out of place next to Ted, but he stuck to him like a puppy dog.
Once I got them set up, they pretty much kept to themselves, which was fine. They were pretty much keeping up with me and Kenny, but they were both kind of weird, so we kept them at a distance.
They showed up in an old pickup with a homemade camper, and I noticed that the truck would be on the lot at night when I headed out and still be in the same spot when I showed up in the morning. I figured out that the Ted and Bobby must be living in it. They weren't the first workers we had living out of their cars, but with two of them, that camper had to be pretty cramped.
Then one day Kenny said he had overheard them talking and he was pretty sure from what they were saying that they were actually sleeping together. He was freaked out about that, but I just told him to let it go.
"Well, don't expect me to work with them. That queer stuff weirds me out."
"They do their work and we do ours. It doesn't really affect us," I told him. What I didn't tell him was that it triggered my curiosity.
I got married while I was still in school, and I had been married long enough to get to that stage where the sex is hard to come by and what little there is gets boring. So, anything out of the ordinary intrigued me.
I wasn't gay and I couldn't even say if I was bisexual. I Know I wasn't attracted to guys at all. But when I was still in college, I used the gym a lot and I began to realize that while I could see guys all day long and never think twice about them, their cocks were a different story. For some reason I found those damn things absolutely fascinating.
Growing up, I had very little exposure to naked men and their appendages, and I guess I had always assumed they were pretty much the same. So, the variety came as a surprise to me. Not just the size, but the shape, and girth, and if it was cut or not.
I had no attraction to men, in general, but I was fixated on what they had swinging between their legs, and it wasn't a giant leap to go from thinking about cocks, to thinking about what the two men might be doing with them.
At the jobsite, on hot days, the Sani-cans got really nasty, and they weren't always convenient anyway. It was usually easier just to find a hidden spot behind a building and pull out your pud to pee. That's what I was doing one day when Ted walked up.
"Time to drain the lizard!" he barked, announcing his arrival.
He walked right up to the wall next to me and opened trouser. I had been ready to start but his sudden arrival had managed to freeze my process. I just stood there trying to get my pipes running again, while I heard what sounded like a pressure washer digging furrows in the soft soil. I couldn't help myself. I glanced over and saw what Ted was packing.
It's not like it was huge, but it was impressive, and fates be damned... over time I had developed preferences about cocks... his was nearly perfect, at least according to my personal scale. It had a nice heft, and it was perfectly proportioned, thick from the base all the way to a nicely tapered knob.
I realized I was staring, so I lifted my gaze and saw that Ted was looking right at me and smiling.
"Man! That feels good!" He crowed.
I laughed nervously. "Geez dude, how much water have you been drinking?"
"It can't be that." He challenged. "I never drink water. Fish fuck in it. I get all my water in beer form, and I drink plenty of that." Then he let out a belch, apparently as proof.
I had finally managed a slow trickle, so I stared at the wall while Ted finished. I expected him to leave, but he was still there, with his dick hanging out.
"You should stop by the truck sometime and have a brew."
"Sure... maybe sometime..." I mumbled, finally shaking out the last few drops.
"If you shake that more than three times, you're just jerking off." He accused.
I laughed nervously, and packed my junk, still zipping up as I turned my back and walked off.
I tried not to give it any thought after that, but I did catch myself thinking about Ted's cock the next time I jerked off.
After the weekend, I showed up at the job site and saw that their truck was gone. It wasn't unusual to have someone take off right after paychecks and I assumed that might be what had happened. Ted and Bobby didn't seem all that career minded.
But about an hour later, I saw Ted's truck and camper bouncing up the access road. I was moving some bundles of siding as he pulled up to where I was working. When he got out I realized that Bobby was nowhere to be seen.
"What happened to your partner?" I asked.
"He was just with me for a few weeks of summer. I had to take him to catch a bus so he could get some money from his parents to go back to school."
"Oh... I should let the boss know so he can hire someone else."
"Fuck that!" he growled. "We can get it done. More money for the rest of us."
I knew the boss would want us to keep up our usual pace so the only way that would work out is if we worked extra hours. But the truth was, prior to this gig work it had been slow, so I could really use the extra cash. I decided to go along with it.
Kenny, however, wanted nothing to do with that. "You guys can work your asses off all you want to, but I am out of here at four."
So, after everyone else would head out, Ted and I would stick around and work on making some extra money while there was still daylight.
After working a long day, Ted reminded me about the invitation to stop by the camper for a beer. I was parched, and the old lady had been giving me grief, so I was in no hurry to head home. I went for it.
When we got to the truck, I had to admit to some curiosity about what was inside his home-built camper. "Well, see for yourself," Ted offered, and I followed him in.
It wasn't as cramped as I thought it would be, but there wasn't a lot of extra space. I had half expected it would be a dump, but Ted was a pretty decent carpenter, and it showed. He had built-in cabinets and a couple bench seats with pads, with a table in between that I could see collapsed into a good size sleeping space.
"Damn, I'm impressed!"
"Thanks," Ted answered as he handed me a can of beer.
We sat across from each other, sipping suds, and just shooting the shit.
He told me how he had joined the Merchant Marines right out of high school, and when he quit that he moved around the country taking whatever work he could get, finally ending up here.
I was starting thinking Ted might not be as weird as I had first thought. He had some interesting stories, and I even envied his unconventional lifestyle.
"So how did you and Bobby meet up?" I asked innocently.
"He was having some trouble with school, and he was going to drop out. His parents got pissed and kicked him out of their house. He was panhandling downtown and camped out at a local park. I was just passing through, but I decided to stay for a few days and we got talking. He let me know he needed some cash so I'd give him a few bucks to get by, and he would blow me... or I'd fuck him up the ass. After that we just started hanging out."
"So, I guess what Kenny heard must have been true then? You guys were hooked up?"
"A marriage of convenience I guess." Ted answered. "Skin is skin. I don't really care who I'm screwing. I just don't like to go very long without."
I felt a stirring in my groin, as I confirmed that the rumors were true, and my imagination ran through a slideshow of all the various sex acts that might have occurred in that camper.
"What are you going to do now that Bobby's gone?"
Ted shrugged. "I can probably go into town and find some chick to ride my pole... or I may luck out and find someone closer."
I was nodding as if I understood, but when I looked up I saw that he staring right at me, and I realized that I had missed his point.
"Oh... hey... I've never swung that way." I explained. "I mean... I'm flattered but..."
"Did you ever think about it?"
I wasn't sure how to answer that. I had thought about men having sex, but somehow I had never put myself in the scene. Now, suddenly that was all I could think about. But I still wasn't sure I felt about it.
"Not really... I mean... I guess I have wondered what it's like... for guys who do it."
Ted took a deep breath and I saw that his hand was massaging a growing lump in his jeans. "You could find out."
I felt like I needed to get out of there, and while I knew I could make up an excuse for why I needed to leave, I didn't know how to do that and still explain the raging hardon that was tenting out my crotch.
"I don't know... how..."
"That's okay." He assured me. "I totally do... and I promise, I can make you feel really good."
"I guess..."
I didn't need to finish that sentence. Ted stood up, and like me, I could see that he had a noticeable bulge. He helped me stand and then started undoing my clothing.
"Let's get more comfortable."
I felt anything but comfortable, but I also felt excited as I anticipated what was about to happen. I had never given much thought to the whole dominant/submissive thing. I know I had no interest in controlling someone else, and I would have said I didn't like being controlled, but I realized that sex with my wife was always about me giving in to doing whatever she wanted. And when she didn't want sex at all, I went along with that too.
Having Ted take charge didn't feel like he was bossing me around. It was kind of like with my wife, except that he actually wanted the sex... and so did I.
I finally got my motor skills back and I took over removing my own clothing, so Ted was able to focus on his. I was still fumbling, and nervous and we both finished disrobing about the same time. Then we took a moment to check each other out.
I had the classic farmer tan, showing a variety of shades, depending on where the skin was exposed to the sun. Ted was a medium bronze over his entire body, and it made me wonder when and where he was sunning naked, because I didn't know any other way to make that happen.
Our bodies were otherwise similar, as far as height and build, but there was a noticeable difference in what we had packed between our legs. I had seen Ted's cock when he peed, but not swollen. It wasn't full hard, but it was moving in that direction, and it was easy to be impressed.
My cock on my body looked okay. I would even say it was better than average. Ted's cock on a similar body looked out of place, like he was borrowing it from a bigger man. It should have scared me off, but it didn't.
There was a point between drinking beer and talking about sex, and then standing naked in front of each other, where I went from wondering what it might be like to get fucked, to desperately needing it to happen. I still wasn't sure it would work, but I had to find out.
Ted was scanning my body like a man evaluating a horse he was thinking of buying. Apparently we made the sale.
"Damn! You're even prettier than I expected."
I had to chuckle. "I don't think anyone has ever called me pretty."
"Beauty is in the eye of the beholder." He stated. "Let's do this."
Ted opened a cabinet and pulled out the biggest jar of Vaseline I have ever seen. It was about two thirds full.
He saw the look on my face and shrugged. "I guess I really like to fuck ass. I want to be prepared."
He scooped some lube into a couple fingers and then turned to me. "Time to get you ready."
I swallowed hard. This was suddenly real. Really real. I turned and gripped the edge of the table giving him the access he needed.
He wasn't in any way rough or rude, but this was also clearly not a romantic encounter. This was two guys getting ready to have sex. He was almost clinical in the way he applied the lube to my pucker, and slipped one, and then two fingers up my poop chute.
To be honest, it was probably the exact right way to handle it. If he had tried to make it something more than that, something precious or intimate, I would have been put off by it. I was already married. I even loved my wife. I had that part covered. This was about getting laid.
The tickle of his fingers prodding my rosebud was unusual but oddly comforting. Then, when his fingers slipped inside me, it shifted from testing the waters into something overtly sexual. I was being penetrated, even if it was just fingers. I knew this was only the prelude, but my body was responding in ways I could never have imagined.
My dick was fully hard and looking ready to burst.
"I guess you're ready." Ted confirmed. His fingers were quickly replaced by the knob of his cock. The difference between the two was enough to make my sphincter resist entry, but the memory of those fingers was enough to make it relax a lot quicker than my pride wanted to accept.
Once the crown had breached my hole, the rest slid in smoothly. It was still a long slide before I felt him press against me. I felt stuffed, like I had to take the biggest dump of my life, but I had no desire to relive the pressure. Even when he pulled back, almost pulling free, all I wanted was to have him back inside me again.
"Holy shit!" Ted grunted. "I can't believe how good this feels!"
"I thought you said you fucked ass before." I challenged him, thinking he was just blowing smoke to make me feel good.
"Hell yeah," he agreed, "but there is ass... and there is ASS. It's not all the same. Yours is something special."
What I was feeling was pretty special. I thought it was sad that I had not known it would feel like this. I am sure I would have found a way to do it sooner if I had known. As he moved inside of me, I began to reconsider my feelings about romance and intimacy, because while he was fucking me he could have asked me to marry him, and I would have called my wife immediately to let her know we were getting a divorce.
But I knew it wasn't truelove. I mean... I loved his cock, and I loved being fucked, but this wasn't love. This was full throttle lust, and I was totally fine with that.
Almost as soon as he started humping my hole, my dick started leaking precum like a slow faucet. I wondered if I would have anything left for my orgasm, which was coming on fast. If I had touched my cock I would have blown immediately. Instead, I tried focus on delaying it, worried that I might not be able to still take his cock if I came before he was finished. It turned out I didn't have a choice. My body suddenly clenched and trembled, and my load spattered across the table in staccato bursts.
It turned out my concerns were unfounded. As long as he was plowing my hole, my dick stayed hard, and my own pleasure continued undiminished.
My orgasm, and the clench and grip of my anus on his shaft, did have an impact on him. He grabbed my hips and sped up, fucking me with all the force he could muster, driving himself to the finish.
It was still a good ten more minutes before his pace was interrupted by a sudden halt, jab, and then soft pulse as my ass was filled with his milky spooge. He pulled in close, buried as deep as he could get through the first couple pulses of his sperm, then he began to stroke into me again, but slowly, like he was wringing it out.
It worked for me. I fired off my second load of the night while he was still finishing up inside of me.
Ted dropped on top of me, pressing his weight across my back, pinning me to the table. I could hear his breath, ragged and deep in my ear.
Some time passed before either of us moved again, but then Ted slowly lifted off me and, even more slowly, pulled back, letting his cock slip wetly from my ass. I tried to stand but I struggled to find balance. Ted helped me seat myself on one of the benches.
"Mother fucker!" Ted gasped, still breathing hard. "Tell me you never did this before?"
"Never..." My voice cracked.
"Mother fucker... I think you ruined me."
I frowned. "What do you mean?"
He was shaking his head. "I was figuring I'd move on after this job is finished... Now, I don't think I can leave."
I grinned and gave him a sideways glance. "Don't shit me."
He looked at me like I was stupid. "How was that for you?"
"I... I mean... I never felt anything like that before." I admitted. "I know, I never came that hard before."
This time he nodded. "Well, that makes two of us."
"You're being serious?"
"Hell yeah. I swear, I will probably have to kill myself if we never do that again."
I chuckled. "Heaven forbid! I can't be party to a suicide."
Ted had a devious grin on his face. "I can get really depressed. It might have to be a regular thing."
"Well, it better be!"