Date: Mon, 14 Sep 2020 23:03:42 +0200
From: Game Dog <mrgamedog12@gmail.com>
Subject: Pleasing the boss

My second semester at college was coming to an end, unfortunately so was
my money. I was not exactly looking forward to it but I had to find a job
for the semester break, lest I wanted to eat nothing but dry rice for a
month.

Thankfully, complaining to one of my friends, Simon, was the right
decision. His uncle owned a company doing gardening and water features.
He offered to put in a good word for me and actually managed to secure me
an interview with his uncle.

Then I met the Uncle for the interview, I was pretty quickly overwhelmed
by his personality. He introduced himself as Thomas and without even
waiting for an answer, he started talking about the company, the work,
the weather and the good ol' times. He was walking me through the
company grounds and I actually had a hard time following him, while also
trying to retain as much of the information he threw at me. As we walked,
I had a bit more time to look at him. He was in his late 40s I guessed,
but in seriously good shape. His biceps were huge from hard work, the
dirty t-shirt he was wearing doing nothing to hide his muscular back. He
sported a pepper and salt scruffy beard, his hair mostly hidden by a cap.
Although he was wearing thick working pants, it was obvious he had a
nicely shaped, firm butt.

"Got any questions? No? Alright, then I leave you in the hands of Eva.
You will do fine around here!", he told me as we found our way back to
the front office again. He did not actually wait for me to ask him a
question and went off again. Luckily, I was greeted by a nice lady who
introduced herself as Eva. Apparently, she already knew the boss' antics
and made sure to properly introduce me to my tasks and gave me ample time
to ask questions. In short, my job was to answer emails, phone calls and
the occasional walk-in, directing people to the proper technicians and
workers. Still had to learn about the equipment, the services and
terminology, but nothing to major.

Over the course of two weeks, I got to know most of the people in the
company. Although I mostly interacted with Eva in the office, sometimes I
would also hang out with the boss and his "boys". Apparently, Simon was
also working here over the semester break.

Thomas was a very charismatic guy, the kind of person you could easily
get along with. However, he NEVER stopped talking. Even while eating, he
went off adding sometimes very "colorful" commentary to the discussion.
I'm a relatively quiet person, but that was not a problem for Thomas.
Any void or pause was immediately filled by him talking again.
During my last week, Thomas approached me to make an offer:

"Hey Michael! I know you can use some extra cash, got an offer for you.
There's gonna be an exhibition show soon, I want to present the company.
Think is, last year I kinda got swamped by people, plus I had to set up
the booth and everything by myself. You already deal with customers,
answering questions and so on. Three days, two nights, business casual.
You in?"
"I mean sure, I would love the extra cash. But wouldn't it be better to
take Eva? She got more experience than me."
"True, but she's a married woman. Got kids and everything, she would
rather stay home." Lowering his voice and whispering he added: "Also
wouldn't be proper to share a bed with her, me being a man and all you
know." He started laughing loud and slapped me on the back. Not sure
what joke I just missed but I agreed to accompany him on the trip.

Boy I had no idea what I got myself into. After loading the truck, we
started our trip. A seven-hour trip with a person that keeps talking
endlessly and has a bit of a Mad Max attitude to driving. Throughout the
trip I learned more about gardening than I ever imagined (or wanted to
learn), praying to every God I knew of to not let me die in a car crash.
While Thomas kept switching topics through his incessant chattering, only
interrupted by occasional yelling and swearing at over drivers, we
eventually landed on a dreadful topic. Relationships.

He is divorced ("Awful bitch, don't know how we lasted 10 years!"),
hasn't had any luck with the ladies ("How do you even date nowadays?
What the hell is tinder?") and the lack of sexual activities in his life
("I swear I jerked off more than I did during my teens!") he eventually
started to ask me about my love life.
This was not exactly a conversation I had in mind, but unfortunately, he
was rather insistent this time, actually expecting some answers from me.
I tried to dodge the question but he was relentless. Eventually, I caved
and told him I was not in a relationship. That made him shift the topic
to something even worse, Sex.

And so, he began to talk about his various experiences at high school and
college. His preferences and in general way too much information. By this
point I was already pretty embarrassed but he decided to up the ante and
started to ask me for MY experiences ("You're pretty good-looking guy,
you must have the girls all lined up"). I tried to tell him that I was
rather not interested in girls, hoping the topic of homosexuality would
make him switch topics again.
And he actually was quiet for about a minute! And then the question
started flooding in. What's it like kissing a guy, what's it like to
suck a dick, you like pitch or throw, how back in his days gays were
rare, and so on and on. It was the absolute longest seven hours of my
entire life.

Thankfully, we eventually made it to the hotel. We checked in and I had
to notice the singular queen-sized bed in our room. Oh joy, he really
meant sharing ONE bed. Well, after the long drive we were both pretty
exhausted. I took a shower first in the very small but clean bathroom.

While the warm water washed over me and I enjoyed the temporary silence
of a shower, the door opened. I had not locked it, figuring Thomas was
well aware I was in there, but he did not seem to mind. The shower was
just a corner, with no curtain or wall to hide, so I turned around,
rather embarrassed.

"Sorry, I just really have to take a leak.", he said and already began
to fish his dick out of his jeans. He aimed at the toilet bowl and let
out a powerful stream of piss. I could not help myself but take a peek.
His dick was one of the biggest I had seen and that was just flaccid.
About 6 inches long and very thick with a big pronounced head.

Quickly, I turned around again, feeling my cheeks flush red and my dick
starting to get hard. How long was he going to piss?! I heard the sound
of a zipper, a quick "Sorry for interrupting" and he was out the door.
I finished my shower, dried off and wrapped a towel around my waist. As I
stepped out of the bathroom, I got another surprise. Thomas had already
taken off his clothes and was only holding a towel in front of his
crotch. Seeing him naked confirmed my first impression of his body. He
was in excellent shape, with muscular legs, a very well-defined butt and
an impressive chest. His abs were still quite visible despite his age and
his back was thick, trained and hardened by his work. His body was
covered in black and white hair, he was definitely rocking the
salt-and-pepper look. Thankfully, the towel around my waist was hiding my
growing erection long enough for him to squeeze by me into the bathroom.
I quickly put on some underwear and slipped under the covers. When Thomas
came out of the bathroom, I pretended to be asleep.

The next morning, we got up early. For the exhibition we both dressed in
slacks, shirts and ties. Watching Thomas getting dressed made it that
much more challenging dressing myself. He looked absolutely stunning in
proper clothing. So far, I had only known him in dirty t-shirts and work
clothes.

The booth was quickly set up and when the first people came over to show
interest, Thomas really showed his charm and business expertise. He had
no problem handling multiple conversations, making people laugh and enjoy
themselves. My job was almost too easy, only having to hand out
pamphlets, noting down contact information or answering a question or
two. Still, the exhibition went on until late evening.
"Good job! Made the right call to take you with me!", Thomas told me
with a smile and a slap on the back. "Let's go to the bar, drinks on
me!"

Oh, the magic words every student loves to hear! We spent a good two or
three hours at the bar both drinking our fair share of beer and spirits.
Thomas loved his whiskey, while I settled for some rum and coke. It was
almost midnight when we made it back to the hotel room. Both quite a bit
drunk.

I went into the shower first and the same thing repeated itself. While I
was washing the sweat of the day from my body, Thomas came in to take a
piss. This time however, he did not leave after shaking the last drops of
his cock. Instead, he started to undress.

"Hey, so, you know. Late already, should we, should we share shower?
Saves time!", he asked with a bit of lull to his voice. I don't know if
it was the alcohol or my own horny mind but I just nodded and made room
in the already small shower. It took not long and we started to lather
each other's body with soap. By now we were both sporting full
erections. I always considered my 6 ½ inches as pretty decent, but he had
me easily beat with about 7 ½ - 8. And his cock was thick, very thick!

"Fuck, it's been so long!", Thomas moaned as my hands roamed over his
body, worshipping his muscles. He placed a hand on my head and slowly
pushed me down. With a husky voice he said, almost whispering: "Please,
I just... I just need it so bad."

At this point I was beyond any embarrassment. He may be my boss, he may
be almost twice my age, I did not care at the moment. I wanted his dick
in my mouth. And so I got on my knees and took his erection in my one
hand, my other hand grabbing his butt cheek to steady myself. My tongue
licked his head, before I swallowed as much as I could. Not even half on
my first try, but Thomas let out a loud moan that reverberated through
the small bathroom.  Invigorated by his display of lust and forced a
little by his hand on my head I began to more eagerly suck his dick,
taking more and more of the shaft in my mouth. Finally, I felt his head
push against my throat. Relaxing and taking a deep breath I took him all
the way in, pushing my nose in this thick bush.

Thomas let out a hissed "Yes!" and now with both hands holding my head
in place began to move his hips back and forth, slamming his cock in my
mouth again and again. He was a strong man and I was in no position to
resist him and so I just did my best to please him. He was lost in
pleasure, his eyes closed he stood slightly hunched, the water hitting
his chest and flowing down his body. Both my hands were holding onto his
ass, sometimes roaming over his powerful calves, feeling the muscles work
as he pumped himself into me.

Through gritted teeth he shouted "Fuck!" and slammed his dick all the
way into my mouth. His balls drew close, his muscles tensed and he came
deep into my throat. After a few shots straight down my throat he pulled
out a bit, just enough to fill my mouth with his cum. I tried to swallow
as fast as possible, but it must have been a long time since he last got
off. It seemed he was shooting forever, his cum overflowing from my
mouth. Eventually, the tide of his seed stopped. I swallowed the
remaining cum, then licked his cock clean. Thomas was breathing heavy,
his eyes still closed, water still flowing over his body.

I really hoped he was not second guessing this, now that he had relieved
himself. My worries were unfounded. He turned off the water, lifted me up
and carried me out of the bathroom. He threw me onto the bed, still
completely wet, and quickly got on top of me. He pushed his lips on mine
and began to kiss me, his tongue forcing its way into my mouth. While
kissing me he grabbed my cock and began to slowly stroke me, a bit clumsy
and unsure. Probably the first time he had another man's penis in his
hand. We stayed like this for a while.

I could feel something moving against my leg and when I looked down, I
saw his cock starting to become hard again. He stopped kissing me and
flipped me on my stomach. Kneeling between my legs he started to rub my
back, his hands slowly moving lower and he began to massage my ass.
Pulling it apart and just looking at my hole. He was exploring my lower
body, sometimes letting a finger glide through my cleft over my hole.
Then he tried to push a finger in, dry. I winced and tensed up.

"Thomas, my wallet." I told him; my voice almost cracking from my
arousal. He got up, picked my pants off the chair and took out my wallet.
He rummaged through it and found a small packet of lube. Quickly, he got
back between my legs. I was expecting him to use the lube on a finger,
but he had other ideas. He ripped the packet open and began to drip it on
his hard cock, spreading it all around. He smeared the rest onto my hole
and got in position already trying to push in.

"Fuck, take it easy! Go slow!", I shouted. Thomas at least had the
decency to shoot me a quick apologetic look. He pushed in a finger, again
rather rough and fast but manageable. After finger fucking me for a bit,
he started to push his dick in again. I wanted this man, really wanted to
get fucked by his huge cock, so I tried to relax and let him in. It was
painful and I bit into the pillow to stifle my groans of pain. But
slowly, ever so slowly he pushed into me, sliding more and more of his
hard rod into my guts. And then, finally, I felt his balls making contact
with mine, his hips hitting my ass. Now completely inside of me, he let
out a loud moan and laid his chest on my back, stroking my hair and
whispering into my ear:
"It's been so fucking long. You're so fucking tight. Fuck!"

Slowly he began to pull his cock out again and just before the head
popped out, he pushed it back in slowly. He was clearly enjoying the
tight hole; god knows how long he had any proper hole to fuck. After a
minute of sensual slow fucking, he lifted his chest up, grabbed me by my
hips and pulled my ass up. He continued to pull out slowly, but now
slammed it into me with force, smashing his hips against my ass with a
loud smack, holding me in place. The initial pain of getting fucked had
subsided and pleasure began to shoot through my body with every hard
thrust. My dick had gone soft but was now getting hard again. And Thomas
began to really fuck me. No longer going slow he was increasing the tempo
of his thrust, still pulling almost out, just to slam back in, over and
over.

My hands were clawing at the bed sheets and I was moaning in tact with
the pounding I was getting. My cock was spraying the sheets with pre-cum,
swaying back and forth. I could feel myself getting closer, the
stimulation to my prostate driving me slowly over the edge.

To my frustration Thomas pulled out. He threw me on my back, pushed my
legs down to my chest and quickly slammed his cock back inside me. He
leaned into me, looking at me while he was fucking me hard. Sweat was
dripping from his body. His breathing was getting more irregular and he
started to make short, rapid thrusts. He started to kiss me again, before
slamming his dick deep inside me as he started to unload. Moaning into my
mouth, I felt the warmth of his seed spreading in my hole, as he shot
more and more of his cum into my guts. While still riding out his own
orgasm, he grabbed my leaking cock and with a few quick jerks I started
to shoot my own load, decorating both of our bodies with my cum. My ass
was squeezing and milking the last bit of cum from Thomas' cock. He
collapsed on top of me, smearing my cum all over us and we fell asleep
exhausted from alcohol, hard work and even harder fucking, in sticky, wet
bed sheets. Poor housekeeping.

We overslept the next morning. We hurried under the shower, together and
quickly tried to get ourselves representable. Thomas took two aspiring,
nursing a pretty bad headache. Nothing was said about the events the
night before. The rest of the day was spent at the exhibition, Thomas
being a bit more reserved but still did his best to reel in potential
customers. Later in the evening we started to pack up, still being too
busy to really talk. Even as we started heading down the highway with our
truck, Thomas still driving like a mad man, we remained silent. I was
starting to worry, that we took it too far and frantically was trying to
think what to say to ease the situation. Before I could come up with
something, Thomas spoke up with an unnerved voice:


"I'm sorry. I really am. I drank too much and I forced myself onto you.
I should not have done that, any of that and I'm really sorry that I
hurt you. When we get back, I will drop you off home and send you the
payment. You don't have to come in for the rest of the week, I know you
probably want to get away from me. I'm just really sorry. It's been so
fucking long that someone touched me, I just couldn't control myself.
I'm sorry."
He unloaded all of this in record speed, repeating "I'm sorry" again
and again. I had to put a stop to it:
"Okay, stop saying sorry! Look, I actually enjoyed this okay? You're
pretty fucking hot and yeah it hurt quite a bit because you got a fucking
big dick, but I still enjoyed it. No need to panic okay?"

Another awkward silence. After a minute of driving, Thomas spoke up
again, this time with his usual cheerful voice.
"So, you think I got a big dick huh?"

I groaned and rolled my eyes, but could not hide a smile. Slowly, he got
back to his usual chatty self. By now it was already dark outside, the
road starting to get empty. My mind drifted back to last night and I
could feel my dick growing in my pants. With that I got an idea. We were
sitting pretty high up in a truck, it was dark already. I placed my hand
on Thomas' leg and began to slowly caress him, squeezing his muscles.
Thomas looked at me with a quizzical look before focusing back on the
street. I started to open his pants and pull his underwear down a bit to
pull out his flaccid cock.

"Oh wow, really?", he said, his eyes going back and forth between me
and the road. Moving my head to his crotch I took his penis in my mouth
and began to slowly suck it, using my tongue to play with his foreskin. I
could feel him getting harder in my mouth. One of his hands left the
steering wheel and softly stroked my hair. I could hear him moan ever so
slightly. I was in no hurry to finish this blowjob, we had plenty of time
on the road. I began to slowly bop my head up and down, making sure to
swirl my tongue around his shaft and head. Taking his dick out of my
mouth, I kissed his hairy balls, stroking his shaft and licking the
pre-cum from his cock head, then taking him down to the root pressing my
nose into his stomach and swallowing to massage his cock with my throat.

This went on for the better part of an hour, with me taking short breaks
when I felt him getting close. Thomas' hands were gripping the steering
wheel, he was forcing himself to look forward trying not to crash the
car. Only his hips betrayed his concentration, occasional humping into my
mouth. I figured he had endured enough and went back to sucking him with
vigor. Moving my head fast, my hands playing with his balls, he finally
gave me my reward. I placed his cock just on my lips, I wanted to taste
this load. Edging him like that made him cum hard and I could feel the
spurts of cum hitting my mouth. I kept swallowing, this time managing to
keep up. Seems like I did drain his balls pretty well last night, today's
load was a bit smaller. With a satisfied smile, I stuffed his dick back
in his pants, patting it for a job well done and leaned back in my seat.
Surprisingly, he remained rather quiet for a while. Seems the secret to
keep this man from endlessly talking was to blow his dick.

We finally made it home and he dropped me off rather unceremoniously.
After all, I still had two days of work left.

The very next day was rather boring. Some emails had started to pile up,
Thomas was working on some gardening project. On my last day, Thomas did
something rather unusual. He was asking me to do some work that would
take me quite a long time, way past my normal work hours. Seems like he
wanted to milk the cheap labor!
Everyone else was long gone while I was still typing away at the
computer. Thomas knocked on the door, came in and handed me an envelope.
"Here is the extra money for the exhibition job.", he said with a smile
on his face.

I opened the heavy envelope. It was a lot more money than I expected.
Besides the cash, there was also a photo included in the envelope. It was
a naked selfie of Thomas, not a great one but it showed of his huge dick
in a nice way.
"Well, that is certainly a nice bonus. Would love to get home and think
about what to do with that, if only my tyrannical boss had not given me a
shit load of work." I said with a theatrical sigh.

Thomas smiled at me and pulled out his dick through the fly of his pants.

"How about I add another load to that?", he said waving his flaccid
dick in front of my face.

Without answering I grabbed it and began to suck him, getting out of my
chair onto my knees. While I was sucking Thomas, I opened my own pants,
pulled down my boxers and started to play with my hardening dick. We took
it slow, Thomas moving his hips slowly, enjoying the feeling of my wet
mouth. I began to swipe my pre-cum with a finger and began to use it to
lube my ass. Not a great substitute but I was enough to get a finger in
to loosen me up. Thomas pulled me up, flipped me around and pushed my
chest down onto the desk.

"You know I looked a thing or two up on the internet.", he said and
kneeled down, bringing his face closer to my hole. He began to kiss and
swipe his tongue over my hole. He then began to push his broad tongue
into my asshole, really rimming me.

From the door came a different voice:
"Seems like you really took advantage of the job I got you." It was
Simon. He was standing in the office door, without a shirt, pants open
and his hard dick in his hands. Simon was almost as big as his uncle, not
quite as thick though. We had previously fooled around at college; I
suppose we were sort of an item. He came closer to me holding his
throbbing cock in front of my face. So, I started to suck him, while his
dear Uncle was rimming my ass. After some time, Thomas stood up. I could
hear him shuffling around for a bit and when he placed his cock head at
my hole. He had apparently brought lube this time and pushed much slower
and more carefully into my hole. Once he was inside, he leaned forward
and grabbed his nephew's head. The two started making out while pushing
and pulling their cocks into my mouth and ass. I was getting spit-roasted
and my dick was rock hard, leaking onto the carpet.
After getting used like this for a few minutes, Thomas and Simon switched
places. They both began to increase their speed, fucking my ass and mouth
in earnest now. To my surprise, Thomas pulled out of my mouth and went
behind Simon. He pushed Simon's chest to my back and began to rim
Simon's ass while the latter slowly fucked my hole.

After deeming Simon ready, Thomas stood up and pushed his cock into his
nephew's hole, both of them moaning loudly. Now Thomas began to fuck
with powerful thrust, every time he pushed into Simon, he pushed him into
my ass, fucking us both at his rhythm. Simon was getting louder and
louder, my hole massaging his dick while his own ass was filled by his
Uncle's big cock. It soon proved too much for him and he began to shoot
his load into me, filling my guts with his seed. Thomas pushed his hips
forward, holding him deep inside me.

As Simon's orgasm slowed, he pulled his spent cock and kneeled under the
desk, taking my cock in his mouth. Thomas quickly took his place in my
ass and began to fuck me with hard deep thrusts. All too soon I came,
shooting my load into Simon's mouth and with a roar Thomas followed me,
adding his own seed to his nephew's, deep inside my guts.

The three of us laid down on the carpet, a disheveled mess.

"Told you I would deposit another load!", Thomas said with a grin.
"And a bit extra from me.", Simon added.

Well fucked, two loads in my hole and a big stash of money. This would a
great start into the next semester.