This is an original story (M/M, Adult Friends, Anal Sex) based on a real situation and real people. Sadly, the sex is just wishful thinking and pure fiction.
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Max Joy
I was a smart kid, but after high school I didn't have the money or the ambition to go to college. So, for several years, I worked a bunch of shitty jobs, with low pay and lousy hours. I had no marketable skills, and these jobs were easy to get.
The little money I made went to rent for a studio apartment, and enough food to stay alive. I had zero money for clubs or dating, and just barely managed to splurge on a movie every month or so.
Despite that I was fairly content, with no obligations or debts. My only regret was the lack of a social life and a solitary sex life.
For a couple years I worked as a night janitor. We had a crew of five guys, and we all worked at different buildings around town. We would meet with the foreman at the main office, pick up our supplies, and and then we would head out to our assigned location. We would work on our own until it was time to drop off the equipment in the morning.
Other than the late shift, it wasn't a bad job. It was easy and once you got good at it, you had a lot of free time on your hands. This allowed for a particular perk of the job.
Most of the surrounding buildings had businesses on the ground floor, and low rent apartments above. It was a college town, so a lot of the apartments were rented by students, and this provided a fairly regular display of young naked people, sometimes even having sex. It didn't happen every night, but I could usually count on at least one good show per week. When I found one, I would settle in and pound one off while I watched.
I clearly wasn't the first person at my building to discover this opportunity. Several of the offices had binoculars at the ready, so over the course of the night, I would do some work, get to an office with binoculars, then I would search the neighboring buildings, looking for a show.
My building was almost always empty at night, but there were a couple offices that sometimes had late workers. If they were occupied, I would just do my cleaning and then move on to the next office. If they were vacant, I could peep on the neighbors and jerk off.
I usually started work on the top floor, and there was an accountant up there who frequently worked late. He would frequently be on his way out as I was coming in, and we would greet each other in passing. He seemed like a good guy, and he always gave me a friendly smile when he saw me. He had one of the offices that had binoculars, kept on a file cabinet next to the window. So, I assumed he might stay late to watch the neighbors.
One night he was already gone by the time I got there, so I took the opportunity to search the neighbors from his office, and as luck would have it, there was one window, brightly lit with the curtains open. I saw some activity, so I settled in for a possible show.
At first I could only see one guy, and it took me a minute, but I remembered him from a previous sex show when I had seen him blowing another dude one night. I wasn't sure what to make of it at the time, but if anything, I was intrigued by the change of pace and I managed to get off pretty quickly that night. So, straight, or gay, I was cool with whatever would happen and I even looking forward to it.
I wasn't in any way attracted to the dude in the window, he was scrawny, and kind of effeminate, and the guy he had blown looked kind of skeezy. I concluded that meant my hetero credentials were still intact. I just liked a good show.
I watched for the first few minutes, but it looked like the guy was just cleaning the house. I was about to give up watching, but then he looked up like he heard something. He walked out of view and then returned with a second man who had his back to me. The first dude dropped to his knees, opening the other guy's pants, and started going to town on him. I quickly pulled out my pecker and got ready to join them in spirit.
The problem was the guy getting blown had his back to me. I couldn't actually see the action and that was frustrating. But then both men started stripping and once they were naked, the first guy bent over the side of the bed and the second guy moved into place behind him. This put them in profile and for the first time I got a decent look at the second guy's dick. It wasn't porn star huge or anything, but it was pretty nice. A decent length and uniformly thick from the knob to the base. The binoculars gave me a nice close-up view.
After seeing a few gay sex acts, I realized that while I might not be attracted to men in general, I definitely felt something when I saw a nice prick, and this one was very nice. It made me curious about the owner, so I took a good look at his face, and that immediately explained why the accountant wasn't working late.
As I sat in his office, using his binoculars, and getting ready to shoot a load on his rug, the accountant was getting ready to shove his dick up the neighbor's ass.
I don't know if it was because I sort of knew the guy, but I honestly don't think I had ever been as horny as I was right then. I even had to let go of my dick to keep from shooting off too quickly.
The scrawny guy was clearly experienced, and the accountant was able to slip into him with only a little hesitation. He then went to town on that ass and based on how both men were acting, the pleasure was mutual.
Now, totally into it, I gave my dick some badly needed attention, and as expected, I came super-fast. The benefit of cumming quickly was that I was still horny, so I kept stroking and managed a second orgasm by the time the two men were finishing up.
That experience was kind of jarring. I had reacted to it a lot more than I would have expected, and I suddenly had a whole new perspective on gay sex, but specifically anal sex. The part that unnerved me was that my focus was not on what it would be like to fuck a dude, but on the experience of the guy who was getting fucked. And I couldn't stop thinking about it.
I finished cleaning the office in a rush, but did remember to wipe up my spooge, and then moved on to the next one. About ten minutes later, I was calling the elevator so I could start work on another floor. As the door opened, I was startled when I almost bumped into the accountant.
"Oh! Hey!" He blurted, smiling when he saw me. "Didn't expect to run into you. You're usually done up here by now."
"Just finished this floor. I'm heading down."
"So, my office is done?" He asked.
"Yes sir," I confirmed. "Left it spotless."
"That's great... You staying out of trouble?"
"Pretty much," I answered, "but I did take longer up here than I should have. I better get back to work.
"Well, have a good night."
I finished up my shift, almost in a daze, and when I got home I was still feeling shaky about my reaction to what I had seen. When I took my shower, I spent some extra time cleaning the back forty and even tested out the muscles back there by slipping one and then two fingers inside my ass. They went in relatively easy, and it felt... interesting. It made me wonder how much different it would feel to actually be fucked.
Sleeping during the day had never been a problem for me, but for some reason I hardly slept at all before having to go back in to work. I even dozed off in the office, while the supervisor was getting my gear together.
"Are you okay?" He asked, waking me up. "You're looking pretty ragged."
"I'll be okay," I told him. "Just tired. I didn't get much sleep."
"Well," he offered conspiratorially, "if you take a nap on shift, do it until after you're done cleaning."
I assured him I would get the work done but I was running on autopilot as I headed up to the top floor to start. I hadn't even considered that I might run into the accountant, but I saw him coming out of his office, as I got off the elevator.
"Another late night? You weren't here all day, were you?" I asked. He laughed. "No. I have normal office hours, but sometimes I come back in to get caught up, especially around tax time. But now I need to get some sleep."
"Well, I hope you sleep better than I did," I told him. "My ass is dragging tonight."
"Sorry to hear that," he said sincerely, "but your ass looks okay to me."
He chuckled, so I knew he was just goofing around, but the comment hit really close to home. If I hadn't been so tired I would have laughed it off, but instead I just grabbed my cart and started to move past him without responding.
"Hey, I have a question." He stopped me. "Did you move some of my stuff around last night?"
I couldn't think of anything I would have moved, so that's what I told him. "Not that I remember."
"It's cool. I just... found my binoculars on my desk. they're usually on my file cabinet."
In my haste I must have set them down in the wrong place. "Oh... I may have done that... by accident."
"No big deal," he assured me. "Were you doing some sightseeing?"
I knew he was just joking again, but maybe because I was still loopy from lack of sleep, I decided to answer honestly.
"I did get a pretty good show across the street."
"Is that right?" He laughed, but then his expression got serious.
"What... did you see?"
"I just..." I began to reconsider saying anything, but then added, "I was just thinking that you... might not need to go across the street if... you ever want to try that again."
"Wait... You saw me?"
"I shouldn't have said anything. I just... I thought it looked interesting."
"You did?" I could see his gears were turning. "Are you... really interested in trying that?"
Now that he had fully clued in, I was feeling a lot more nervous about what I was saying. "I don't know..." I stuttered. "I guess I just got curious about it... I guess."
I could see him relax. "Man... I never would have guessed you'd swing that way... but that would be really sweet," he said.
"I never... and you have your friend, so..."
"Him?" He laughed. "We're not like a thing. I spied on him a couple times, from my office. It had been ages since I got laid. So, like you, I got curious and one night I decided to knock on his door and see what would happen."
"It looks like that worked out..."
"The sex was... okay, but I'm not really into him." Then looking me square in the eyes, "You're more my type."
"I am? I mean..." I was having serious second thoughts about bringing this up. "I don't know... I shouldn't have said anything..."
"No, I'm glad you did," he offered. "I would really love to try it with you... and I would make sure it was really good for you too."
"I don't know... maybe... someday."
We had been holding the elevator door open, and it decided this was a good time to start beeping at us. I pulled my service cart out and he stepped in. Then, before the door could close, he said, "I hope you let me do it."
That resulted in a second day with almost no sleep. Now I couldn't stop thinking about our conversation. I had no idea what I was thinking, making that offer. I wasn't even sure if I had been serious about it. I was concerned about confronting the accountant again and as tired as I was, I thought about calling in sick, but I needed the money and I decided to go in.
Considering my boss's advice on napping, I went right to work, deliberately starting on the lower floors and working my way up, figuring it would ensure that I wouldn't cross paths with the accountant. So, it was a shock to discover, when I got to his office, that he was still there.
"Oh hey... I didn't expect to find you here," I said nervously. "You must be working an all-nighter."
He nodded. "Yeah... well... no, not really... I wasn't working. I just couldn't stop thinking about what you said... and I really need to know if you meant it."
"Oh... I don't know," I admitted. "I don't even know what I was thinking. I just..."
"There's no pressure," he assured me, "but I would really like to do it with you. I've always liked you."
"Wouldn't it hurt?" I asked. All I wanted to do was run, so I was surprised I even had the nerve to ask the question.
"It doesn't have to," he explained. "We can go slow and give you time to relax."
"Oh... I don't know if I have enough time..."
He quickly interrupted me. "I'll even help you finish your cleaning. I can make sure we have enough time to do it right."
It had been a lame excuse. I already finished most of the building and I had plenty of time.
"Well... maybe we can try..." I mumbled, barely loud enough for him to hear me. I don't know if I was agreeing or just buying time.
"Outstanding!" He sighed, and I watched as he slowly opened his pants and pulled out his cock. It was still soft but hardening, and I was immediately back to how I had felt when I saw it for the first time.
"You have a really nice... cock," I told him.
"Thanks!" He answered, clearly pleased. "You can touch it... just to get comfortable with it."
My hands were shaking as I reached out and wrapped my fingers around his shaft. I could actually feel it getting harder and the sudden memory of what I had seen the night before made my sphincter clench in anticipation. I don't know that I ever got comfortable holding his cock, but I was pretty certain I knew where I wanted him to put it.
"Are you going to let me do this?"
I looked up from his dick and nodded.
"I knew I liked you." He laughed and led me a small couch.
I was still nervous about what I was agreeing to. As much as I liked watching it, prior to seeing him with the neighbor, I had never even thought having gay sex, and definitely not about getting fucked. But now it was all I could think about. It's like I was already hardwired for this. I just needed someone to flip the switch.
He had me sit on the couch and he took off my shoes. Then he helped me pull off my pants and shorts. It wasn't cold but as I leaned back I shivered.
"You're nervous?"
"Yeah." I admitted. "I've never done this before."
"You were serious about that?" he asked.
"I nodded. "Yeah... but... I still want to try."
"Okay," he assured me. "I promise. I will make this awesome for you."
I nodded again, and then watched nervously as he pulled off his clothes.
"Do you have any preference for how you want this to happen?"
"Um... I don't know..." I thought for a moment. "I think maybe I want you... to be on top... like... you're making me do it."
"I don't want to force you."
"No," I assured him. "But I want to feel like... I'm being... taken... It think it will be easier for me to let it happen. Does that make sense?"
"God you are hot!" He sighed. "Yeah that makes sense. I want to fuck you so bad... You have no idea."
I stretched out, belly down, on the couch and heard him fumbling with a desk drawer. Then he climbed between my spread legs and as he pressed closer, I could tell that he had slicked his cock with some lube. It slipped between my cheeks and nestled in the cleft of my anus.
I was excited. I was also scared to death, but I couldn't decide if I was more scared that he would get inside me and it would hurt, or if I was scared that it would hurt, and he would never get inside me.
As I pondered those mysteries, his cock was putting it to the test. The gentle pressure against my sphincter had my hole fluttering, confused by the pressure coming from the wrong direction and not sure how to resolve it.
I realized that I was panic breathing, short and quick. So, I stopped and forced myself to take in a long slow breath, and then let it out just as slowly. I repeated this over and over again, and that did help me relax enough that my panic passed, and I could even feel my sphincter begin to ease open around the crown of his cock.
There was a spot where it felt like we had hit a hard limit, but then the muscles seemed to let go, and his cock eased inside me. He stopped pushing immediately and just let me take some time to adapt to the change.
"How are you doing?"
"Yeah... I'm... okay..." I was still focused on slowly breathing, the words came out like a gasp.
"We can stay like this until you are ready..." he started.
"No... you can go deeper," I sighed. "I want to know... what it feels like."
He sounded surprised. "Yeah! I can do that... I'll just go a little at a time though." Then his shaft slipped an inch deeper inside me.
I suddenly shook violently, and I was cumming. He wasn't even in me all the way and we had only just started. He paused when he felt my body react, but I don't think he understood what had just happened.
"Do you need me to stop?" He asked.
"God no!" I gasped. Please... More."
Reassured, he slid deeper, and my body trembled again. I wasn't exactly cumming anymore, but it still felt about the same. I wasn't afraid of it hurting anymore, but the pleasure was so intense, I didn't know how much of it I could take. If every movement was going to feel like an orgasm, how long could I handle that? I was about to find out.
When his belly pressed tightly against my back, I knew I had all of him inside me. I could tell by his hesitation that he was still concerned, so I rocked my hips, causing his shaft to slither an inch or two, in and out, through my anus.
"Can I fuck you now?" His voice cracked.
"Please..."
With that he started stroking into me. Feeding me the full length of his cock, faster and harder with each stroke. I still felt the continuous, almost overwhelming, sensation of an orgasm, but there was no way I wanted it to stop... ever!
"What's that... thing in my ass... that makes it feel... so good?"
He slowed but didn't stop. "Um... You mean your prostate?"
"Yeah," I agreed. "How many of those do I have?"
He laughed. "Probably just one."
"Hmm... It seems like more than that..."
"It feels good?"
I sighed, responding to every slide of his shaft through my guts. "Way better than good."
"It's good on this end too," he told me, and picked up speed.
This lasted for several glorious minutes, but then he stopped and pulled out. "Roll over," he said. "I want to see your face while I fuck you."
I quickly repositioned, sitting back on the couch, and he climbed between my spread legs and slid into me, now with almost no resistance at all.
He held my ass firmly in his hands and he pounded my hole with his dick. He fucked like a man possessed, plumbing my depths at a furious pace. Despite the battering my body was taking, it still felt incredible. It even pushed the orgasmic sensations over the top, until I fired off the biggest load of my life.
He watched, fascinated, as my cock spray painted my chest, the ejaculation went on and on for the longest time. What he was seeing, and what my ass was doing to his cock must have done the trick for him because, as I gradually hit the end of my orgasm, he began his.
He punched into me, pressing his groin tight against my bottom, and burying his dick ball deep in my ass. I watched in amazement as his entire body reacted to his climax. His back bowed and his arms flexed, his fingers clenching and gripping my buttocks almost painfully. I didn't mind. I was thrilled to take his load and I was still glowing from my own release.
His body shook throughout his orgasm, and he only settled down as the last pulses of scum flooded my guts. He then laid out across me, oblivious to the sticky mess I had made. We stayed like that for the longest time, neither of us wanting to break contact. When we finally did pull apart, his dick slipped wetly from my ravaged anus.
"Holy fuck..." He moaned as he sat back on his haunches. "That was incredible."
"It was," I agreed, as I stared hungrily at his fuck bloated penis. It seemed surreal to think it had been inside of me. "Was I as good as the dude across the street?"
"Who?" He asked. Then, with a sideways smile, he added, "I'm pretty sure nothing has ever felt as good as that."
"Will... you ever want to do it again?"
He laughed out loud. "Friend, I am doing that whenever you have enough time and you let me."
So, I decided to let him in on my secret. "It actually only takes me a few hours to do the cleaning... then I have the rest of the night for... whatever."
He shook his head. "I better stop staying late, and start coming in early."
He brought a warm wash cloth from the bathroom, and we cleaned up as best we could and made our plan to hook up early the next early morning. I only hoped that my ass would have enough time to recover before then, but I was willing to do it either way.
"Don't worry about cleaning my office. I'll take care of it." Then he sent me off to finish the rest of the floor. I saw the wall clock and I realized that we had been fucking for a lot longer than I thought. Luckily, I knew I still had ample time to finish. It made me wonder if we might be able to go more than once. I guess we would find out.
As I was leaving his office, I noticed a stack of business cards on his desk, and I suddenly realized that we had not even exchanged names. So, I read one on my way past.
"Maxwell Joy - CPA." I laughed. "Max Joy... Yeah... that's about right."