Date: Tue, 20 Feb 2024 00:00:50 +0000 (UTC)
From: Martin <cowpokemarty@yahoo.com>
Subject: Story: MAX JOY (MM, Adult Friends, Anal Sex)

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.

If you like my stories, please consider contributing to Nifty.

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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."