This is an original story (M/M, anal sex) based on a real situation and real people from 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.
Technology Trap
I had worked my way up through the ranks of line workers and shortly before my 25th birthday I was promoted to night production supervisor.
It was the early 80s and like most companies, we had functioned forever with old school, handwritten, carbon copy, record keeping. So, there was a lot of resistance and fear when the company suddenly brought in the first MS-DOS 3.0 office computers.
"They'll increase productivity," we were told, but I could tell that most of the staff weren't buying it.
They started with computers in the finance department, but eventually the production office got one. The department manager assumed it was a waste of time to learn how to use it, and if we ignored it long enough it would just go away. However, the General Manager had supported bringing in the PCs and he finally put his foot down and said that someone in the shop had to learn how to use it. It was a unanimous decision that I would be the guinea pig.
That was fine by me. I was curious about it, and I managed to pick it up fairly quickly. Before long I was even doing simple programming. I set it up so the day managers could track the inventories and production schedules. After some resistance, they finally gave in and started using it.
There were times when all the managers would get together for meetings, and other managers would corner me with questions about their computers. I could usually talk them through the problem, and it was cool interacting with the higher ups.
I even felt like I had hit it off with our General Manager, Tony. He seemed like a really good dude, and he said he appreciated all the ways I had made the shop more efficient. During breaks in the meetings, he would seek me out and we would chat. I liked having him pay attention to me.
Not long after we upgraded to MS-Windows and the World Wide Web, the company decided it was time to hire a legitimate I.T. manager. I was actually relieved. For a couple years, I was effectively the shop's computer expert, but it got even more complicated when we upgraded.
I was already spending too much of my work time solving everyone else's problems and now we were getting into stuff, like networks, that were beyond my skillset. Barry, the new I.T. manager, seemed to know his stuff. I thought we might hit it off, but it bothered him that a lot of people still came to me with computer questions. So, he gave me the cold shoulder.
Then, I showed up to work one night and found out that one of the ladies in the office had cleared out the shared printer, and she had found pornography in the stack of printouts. Someone had apparently printed and forgotten it or had just missed their chance to grab it unseen. The office had been buzzing about it all day.
When we first got access to the Web, it was like discovering treasure. Everyone started web surfing and suddenly computers were considered cool. It didn't take long before a few people were caught with inappropriate stuff on their computer, and the company implemented some computer use policies. Then Barry installed a firewall that blocked out websites that weren't directly business related. Even then, we frequently had to get a site approved before it would clear the filter.
I couldn't figure out how someone had managed to get past the firewall to download porn. I knew if the company could figure out who did it, heads would roll.
I went right to work, figuring I would get updated in the morning. So, it came as a surprise when I looked up from my work and saw Tony standing in the doorway.
"Hey boss! What brings you in?"
He looked concerned. "Did you hear what happened with Cindy today?"
I nodded. "I heard she found porn in the printer. Did you figure out who printed it?"
At first he didn't say anything but then he sighed. "Barry said there are likely only a couple people who could have pulled it off."
"Yeah... it would have to be a short list. I still can't figure out how they did it." I realized that if Barry thought there were only a couple people with the skill to do it, my name would be on that short list. I added defensively, "At least it couldn't have been me. I just got here an hour ago."
Tony nodded. "That's what I thought... at first. But Barry said you could have set up a scheduled print time last night. So, it could happen even if you weren't here."
"Well..." I stuttered, "that doesn't make any sense. Why would I print something when I'm not here to pick it up?"
He hesitated, looking uncertain, but then seemed to regain his resolve. "Barry told me he checked the printer log, and your PC showed up."
"That's crazy... I didn't print anything on day shift. I don't even know how to do that."
Tony shook his head. "I'd like to believe you, but the I.T. Manager is telling me we have evidence that you did."
"But I didn't!" I was now feeling angry and defensive, and it bugged me that my computer proficiency was now being used against me.
Tony was holding a manilla folder and he pulled some pages out of it, spreading them out on my desk.
"Cindy shouldn't have seen stuff like this."
I looked and was shocked by the images of men grappling sexually. "Oh my god!" I gasped, confused and even a little scared.
Okay... full confession. I had not printed the pictures, but I also knew I wasn't totally innocent. When I first discovered the World Wide Web it had been like discovering an adult bookstore with everything available for free.
I totally immersed myself in it, and working night shift, I found opportunities to lock my office door and whack off to it. It had started with the usual straight stuff, but it didn't take long before I discovered the variety of porn that was available. For someone with an open mind and no sex life, even the images with men having sex were intriguing.
One of the things that drew me to it, was realizing that I could take either role, top or bottom, and in my mind it was like I was doubling my odds. I did realize that zero times two is still zero, so I knew it was just a fantasy.
When I learned we were hiring an I.T. Manager, I immediately stopped using the work computer for porn, purging everything I had saved and making sure I didn't leave any traces of my search history. I was still terrified that they would figure it out.
So, I was guilty of having viewed gay porn on my work computer, but the pictures that were lying on my desk were not mine. I didn't print them, but I had no way to prove it.
"Am I getting fired for this?" I asked, resigned to the fact that I was the prime suspect.
"That's what the head office wants, but... it doesn't have to go that way."
I was relieved that there might be another option. "Thank god! What do I need to do?"
Tony gave me a long stare. "I have always really liked you."
"Thanks! I really like working for you."
Tony continued. "You're smart and you do great work, but I also... really like you. Do you know what I mean."
I pondered the question. I looked up to Tony. I know I thought of him as a friend, because I wanted him to see me that way too, and I guess in a way I was even attracted to him. But I didn't think that could be what he was talking about.
"I... I'm not really sure."
Tony closed the office door. "I don't have a lot of options here." He explained. "I can fire you... and there is a pressure on me to do that. Or I can try to make this go away, but to make it go away I have to put my ass on the line with the head office and... I would need a really good reason to do that."
"Anything... Whatever you need me to do."
Tony hesitated, like he was afraid to say what he was thinking, but I figured it was only way out.
"C'mon Tony! This is killing me. What do you need me to do?"
"I need you to have sex with me."
I heard him correctly, but it still took some time to have the words make sense. "I don't... I mean... how is that supposed to save my job?"
Tony nodded. "I was directed to fire you, but I told them I needed to talk to you first. If I don't fire you, I need to tell the head office that you didn't do it, despite the evidence. They won't like it, and I may even have to threaten to quit. So, I want to believe you, but I don't think I can put my job on the line... not without a good reason."
"But how... would this help?"
He actually smiled. "I can get fired for having sex with one of my staff. I figure, if you're willing to keep that a secret for me, then I'm willing to keep your secret."
"Well... I don't have a secret because it wasn't me." I confirmed again, but then I added more calmly than I would have expected, "But if it will save my job... I'll do it."
I needed my job, but I also wasn't totally opposed to what was being offered. After all, I had been jacking off to gay porn for over a year. Only, now Tony looked uncertain.
"You really didn't print these?"
"No, I didn't."
I started to think he might be changing his mind, and I couldn't decide if I was relieved or disappointed.
"Shit... that's a problem." I could tell he was upset that the mystery was unsolved, but then he looked up. "Wait... you're still willing to do this?"
I shrugged. "I've thought about stuff like this. I just never thought I would."
"But you're willing?"
"Well, I don't want to get fired."
Tony looked distressed. "I don't want to make you do it. I mean, I thought you were printing out gay porn, so you might want it. I wanted you to... want it."
"Well, I wasn't printing porn... but I have been looking at it... and... I sort of do want this."
"You realize that what I want is what's on those pictures."
I didn't even need to look again. I knew. All of the pictures were of men fucking. That had been what struck a nerve with me because it was a fantasy that had stuck in my brain when I started viewing gay porn. I had even tested the waters with various phallic shaped objects, and the experiments had left me undecided, but still curious.
Yeah... I know."
Tony shook his head. "This isn't going at all how I expected."
"How so?"
"Well... I assumed from what Barry said that it had to be you, but I believe you when you say it wasn't." Tony explained. "I also assumed I would have to fire you because I didn't think I'd even have the nerve to propose this, and I definitely didn't think that you would be willing. I just needed some excuse not to fire you."
"Is that the only reason?"
Tony actually blushed. "Well, no... I do want to. I've thought about it, but I was never going to bring it up. I didn't think it could happen."
"You've thought about me... that way?"
He blushed even more.
I realized that we were only talking to delay whatever else was going to happen and I decided I was done waiting.
"Do you want to try and do it here?" I asked, getting the discussion back on topic.
"Is it safe here?"
"The crew almost never leave the machines, but we keep the job folders up here, so they do show up once in a while."
"That won't work."
I pondered it. "I think I have a better option."
I led Tony downstairs and through the production area. A couple of the printers saw us passing.
"Hey chief! Are you in trouble with the boss?"
"Could be." I hollered up at them. Then, sticking with the usual patter in the shop, though getting dangerously close to the truth, I said. "I don't want you guys to see me cry so I'm taking Tony out to the warehouse. Out there, he can ream my ass out without any witnesses."
They both laughed but I figured I better come up with a better story.
"I need to show him the shipping log. The sales office thinks we shorted some customers on a couple deliveries. I need to prove we didn't."
As we walked away they both shouted at us.
"You better be nice to him, Tony. He's the best supervisor we got!" And then added, "If you need any help, hit the fire alarm. We'll keep working but the fire department can save you."
I shouted back. "Very thoughtful! You guys are the best."
Tony chuckled. "The crew seem to like you."
"I try to look out for them." I explained.
We got to the warehouse which was a separate building on the same lot.
"This is more private?"
"I'm the only one with a key." I explained. "And they won't leave the machines until morning."
Tony nodded and looked around.
At first glance, the warehouse didn't seem like a reasonable place for what we had planned, but at the back there was a breakroom with a refrigerator, a microwave, some chairs, and an old leather couch. Connected to that was a small bathroom. It was private, secure, and reasonably comfortable.
When we got there, I first checked the bathroom and came up empty. I tried the fridge and was relieved to find a tub of spreadable margarine. Tony had been watching me with curiosity, and when he saw what I found the light went on.
"Oh damn! I never even thought about lube."
"Solving problems. That's what I do, remember?"
"Yes it definitely is," he agreed, with a smile. "Does this mean we are really doing this?"
"Oh god... I hope so. I don't think I could work up the nerve again if we don't do it now."
Tony stood, not moving, unsure of the next step to take. So, I stepped up to him and started undoing his shirt. Once I had that off him, he started doing the same for me. It gave us an excuse to touch each other, and the nervousness and reluctance slowly melted away.
"You look really nice." Tony sighed as he stepped back to scan my naked body.
I thought of myself as scrawny and unattractive, and as I looked down at my body, the flickering fluorescent light wasn't doing much to change my opinion. But the look on Tony's face told me different, and as I scanned his body I am pretty sure Tony saw the same look on mine.
He wasn't gym toned and he had softened over the years, but it still showed the basic structure from his college football days. I thought he looked perfect. But it was his cock that really captured my attention.
I knew from porn that cocks came in all shapes and sizes. I didn't really care if they were big or small, but I liked some more than others, depending on the proportions and shape. There were a lot of them that I liked and some that I absolutely loved.
I have a nice cock and I love it. I'm sure familiarity is a factor. It is average size, but I really like the shape and feel of it, and over the years my cock and my right hand had become inseparable friends.
Tony's cock was actually surprisingly similar to mine, that is if you gave mine about 50% more length and girth. It was perfect, and there was more of it. It was definitely more than I had ever tried poking up my poop chute, and that gave me some concern. I had felt some twinges of pain during my earlier experiments, but it always went away, so the pain wasn't my worry. My concern was I would try, find out he was too big, and I would fail. I didn't want to disappoint Tony, but even more... I really wanted to feel him inside of me.
"How should we do this?" He asked, still giving me control.
I looked around the room and settled on the couch. "I want to watch this." I told him, and I sat back with my ass at the edge of the seat, my legs spread for him.
If someone can look like they are drooling without any actual drool, that is how Tony looked. I don't think I had ever felt desired like that before. The only girls I had been with treated sex like an obligation I had to talk them into. That clearly wasn't the case with Tony, and it clearly wasn't the case with me. As scared as I was, I was practically aching for it.
I reached out and grabbed him by his cock, pulling him closer. Then I opened the margarine and spread a shiny layer along the length of his shaft. He scooped some onto a couple fingers and slowly worked them into my butt pucker, twisting and spreading me open.
That's when I realized what had been the missing element with my experiments. That had always felt clinical, and I could always stop when I wasn't sure about what I was feeling. I had no control over what Tony was doing down there, and when I looked up at him and saw the almost feral expression on his face. I wasn't sure I could stop him, even if I begged. So, I just begged him to fuck me.
Tony shuffled closer and lined his cock up with my hole. The soft press of his knob gave me chills, and I felt the muscle stretch, gradually letting him ease inside. My arms wrapped around his back and held him tight, not pulling him in, but also not letting him pull away.
"I don't want to hurt you." He whispered into my ear, and I realized that he was holding back, just barely pushing. The head of his cock was still locked just inside the outer ring of muscle, short of slipping inside me.
I took a long deep breath and leaned up to tell him, "It's okay."
Then I lifted and forced it to pop in and slide deeper into me. I gasped. It hurt, like a kick to the groin, but I kept lifting until I had most of his shaft.
Then, shaking, I let my weight drop and his cock pulled back, far to almost pull free, but this time Tony was ready for it and he pushed back in again. Three strokes like that and he had completely buried his cock up my ass, his groin pressed flat against my buttocks.
"Holy fuck!" He groaned.
"Yeah..." I sighed, no longer feeling the pain.
"Are you okay?"
I nodded clumsily, taking a second to find my voice. "Yeah... but it's... so crazy."
"Tony laughed. "Is it crazy good?"
I smiled up at him. "Yeah, it is... crazy good."
Without any more hesitation Tony started stroking into me. Each plunge sent shockwaves up my spine. My dick had gone soft when he first entered me, but I was right back to a raging hardon, and slowly dripping precum.
"God that's hot!" Tony huffed, looking down at the stringers of scum.
"You have no idea!" I grunted blissfully, as his pace increased.
"It feels good?"
"It feels like... ungh... nothing else... it's... ugh... amazing!"
My breath was being knocked out of me by the force of each hammering lunge into my bowels. Tony, still fascinated by the trickle of precum, reached down and gripped my dick while still pounding his into me. That was all it took for the slow drip of precum to be replaced by the flood of my orgasm. He continued fucking me, as my cock spat out a deluge of sperm, spray painting my chest, one blast even flying past my head and hitting the wall behind me. It was the most intense orgasm I had ever experienced. And even after the last pulsing shot, I stayed hard.
My ass clenched and flexed through my orgasm, giving Tony's cock one hell of a ride. He responded by fucking me even harder. I was being hammered, the force of it sliding the couch backward until it hit the wall and finally stopped moving. Then I was taking the full force of each blow, and I could almost imagine what it must have been like getting tackled by the former college linebacker. I have to assume it was different. Those players likely weren't cumming as a result. Their loss.
Tony's strokes abruptly halted, and he pressed tight against me, holding me and filling me completely with his cock, and then with the warm torrent of his spooge. His body was shaking as he released his load, and as I watched him cumming, I did the same, firing off for the second time.
About the time I stopped shooting, Tony stopped shaking. He stayed buried inside me, and he leaned in and rested across me, gasping to catch his breath. We stayed like that until our pulses slowed and our breathing came back to normal.
"That..." Tony grunted, as he cautiously pulled out of me, his cock still dripping, "...that was so much better than I ever imagined."
"Definitely." I agreed, feeling my sphincter struggling to close and lock in the slow dribble of Tony's sperm. "So... do I need to print porn to make that happen again?"
Tony laughed. "I think we better lay off the porn, but we're definitely doing that again. I usually work late, but I don't know how often I can stay until you get here."
"Hell, I'll come in early for this." I offered.
"That might work. By the way," Tony added, "I do believe you. You didn't print those."
"So, what are you going to do?"
"I'm telling the office it wasn't you and... I am having I.T. tighten up the firewall. It looks like someone else figured out how to get past it. Apparently we aren't the only two with this interest and I don't think I want to start a witch hunt. We can post a warning and I'll just tell Barry to let it go."
We got cleaned up, dressed, and back to work. By then it was only an hour before shift change, so Tony hung out in the shop, until everyone else showed up.
I finished my production report, then I started to head out, but on the way I crossed paths with Barry.
"Tony says you're off the hook." He said.
"I guess so," I agreed. "By the way, is there a reason you pinned it on me?"
"The network printer log showed it was you."
"No, it didn't." I answered with confidence.
"How would you know?" He sputtered. "You can't access the network logs."
"No, but I can access my computer's printer log. That print command never happened."
I could see a sudden flash of panic on Barry's face. He said he had proof, but no one asked him to show it. I knew I could if I had to.
"Don't worry." I told him. "I won't let on. Your secret is safe with me."
He looked defeated. "Why would you protect me after that? I mean... I didn't plan to pin it on you... but I panicked. If I got caught. I'd never get another I.T. job."
"I understand... I will say, it was a shitty thing to do, but I worked it out with Tony."
"Well, I'm glad you didn't get fired." He apologized. "You were the only other computer guy in the office."
"I saw the pictures. I think we may have more in common than just computers."
The panic on his face became a flash of understanding. "Wait... really?"
I shrugged. "Let's just say we seem to have some similar interests."
"You saw the pictures?"
I nodded. "Yeah, I did."
"And... that interests you?"
"Yeah, it does."
"So... are you interested in giving... or taking?" I could see where this was heading.
I chuckled. "That's the same thing I was going to ask you, but... I did recently discover that I do like taking."
"That's cool! I really love to fuck... but I can go either way." He admitted. "I'm always working... so I can't ever meet anybody. And I don't know anyone else, except... uhm... well I guess I know you!" He suddenly brightened.
I smiled. "True. If you ever need to come in early to work on the network, feel free to stop by. Maybe we can see how it goes." Then I added. "But if you really do go either way, and you're interested, I may know someone who can help with that too."
"Wait... Tony?"
I didn't answer. I just smiled.
"Damn!" Barry, paused for a moment. "So... do you think maybe I could come in early tomorrow? I mean... I'd really like to... see where this goes."
"Sure, I'd like that," I answered. "But between you and Tony, I don't know how I'm going to get any work done."
Barry brightened. "It just so happens that I'm getting ready to install some programs that will automate most of your work."
"Really? God, I love computers."