Date: Sun, 10 Dec 2023 17:57:54 -0800
From: Ben Nelson <lentus.diligo@gmail.com>
Subject: Work Trips 3

Disclaimer: This story is based on real experiences from my life, but I
have changed some of the times, locations, and names. This story contains
explicit male-on-male consensual sex.

If you enjoyed this story, please donate to Nifty to help maintain the
site and archive: http://donate.nifty.org/

A few weeks after the Hawaii trip, my boss told me that I was going to be
traveling on my own. Another region needed help as their FSR caught
COVID-19 and so I was going to Chicago.

The next week I was off. My flight to Chicago went on without a hitch;
the flight attendants were both sexy men with their muscular physique
made their uniforms seem painted on. I was staying at a hotel in downtown
Chicago that was kitty-corner from where the Army national guard unit had
its armory.

As soon as I got into my room, I threw on a pair of blue swim briefs and
went down to the pool. A good swim always helps get rid of any jet lag
and relax my body. I was hoping to see some eye candy while I swam, but
no one was there. I called it a night and went to bed.

Early the next morning I woke up and went to the gym. This hotel had a
rather large gym and there was a handful of people already in it. During
my session, I could see this handsome black guy checking me out a few
times. I was wearing short track shorts that were a tight fit so I made
sure to give him a little bit of show whenever I could. I was hoping you
would come over and give me a reason to talk to him, but at one point I
turned around and he was gone.

I went to work and set up my equipment like I normally do then went back
to the hotel. I was just about to leave to go explore the city when my
room phone rang. When I answered it was the concierge telling me that the
hotel was giving me a complimentary massage session if I was available
right now. I accepted and went down.

The receptionist was a very cute woman with a large bust which I'm sure
made it easy to get money out of men. Only a few minutes went by when my
masseur came out. It was my dark admirer from the gym. He was in black
scrubs that seemed to be the uniform of the hotel spa. He introduced
himself as Deshawn.

He took me back to his room and told me to get undressed then lie down on
the table. When he came back inside, he went right to work. His fingers
were magic as they roamed over my body. He worked over my neck, back, and
arms before moving down to my butt, legs, calves, and feet with a deep
massage. He nearly put me to sleep when he worked my feet over. My dick
was hard from the moment he touched my body.

After my feet, Deshawn stepped away for a moment. I thought he had run
out of oil and was refilling, but, in reality, he was stripping out of
his uniform.

When I felt him come back to the table, he spread my feet so they were at
each corner of the table. He then got up on the table I felt him knead my
butt before spreading my cheeks. Deshawn buried his face into my butt and
I felt his tongue lick around my hole and taint. I reached back and
grasped his hands that were on my ass. He held my hands as he ate me out.

Deshawn finished rimming me and then rubbed my ass and his dick with the
massage oil. I felt his black snake slide into me. It was larger than
Bryan's, but after being fucked and double-teamed by him and Jake,
Deshawn's hog slid in easily enough. I still felt my sphincter stretch,
but it didn't hurt.

"Mmmmmm...oh, yeah," I moaned, "that feels...amazing."

I pushed my butt back as fast forward and he drove every inch of his
thick member into my butt.

"Oh, God," he moaned into my ear, "I wanted to do this when I saw you
in the gym yesterday."

"Mmmmm...me too," I cooed back.

We couldn't make a lot of noise, so he slowly thrust his manhood in and
out of me. After he had fucked me from behind for a few minutes, we
switched places on the table, and I rode him in reverse cowboy. I loved
feeling his huge dick stretch my ass as I rode him. When he came, he
pulled me down, shoving the full length of his cock into me, and sprayed
a huge load into my bowels.

I got off of Deshawn and we both got dressed. He gave me a long kiss and
then walked me back to the receptionist. She asked me if I wanted to
leave him a tip and I said, `yes,' so she gave me a manila envelope
which I stuffed with several bills folded around my spare room key.

After a quick shower, I walked around the city for a bit and grabbed a
bite to eat for dinner. I went back to my room wondering if I had missed
Deshawn, but no one had left me any notes or voicemails. I slipped into
bed and dozed off to sleep.

I dreamed about dozens of faceless men fucking me every which way I could
imagine. Leading the group was Deshawn with his huge swinging member
practically splitting me in half. In real life, I was asleep face down,
with my cock hard as a rock and leaking precum all over my bed sheets.

That's how DeSean found me, face down in my bed, slowly gyrating my
hips, and moaning deeply into the pillow. He got into bed with me naked
and parted my cheeks with his hands so he could see my smooth, pink hole.
My dream was so intense that I didn't wake up as he gave me a rim job.
It wasn't until I felt his cock shove into my body that I woke from my
slumber.

"Mmmmm...I thought you'd forgotten about me," I moaned sleepily.

"Nah, baby," he said still pumping into me, "I couldn't leave work
until now."

Being away from work, he no longer cared about noise. He sped up and
rapidly drove his meat into my ass. I felt bad for anyone in the room
next door as my bed smacked against the wall and I moaned loudly.

"Oh...fuck...your dick is so big..." I let out.

I felt Deshawn lying on me. When I turned my head, he kissed me with his
full lips. I loved the way his cock filled me up and rubbed just right
against my prostate. After a few minutes, I cried out and sprayed a load
into the bed.

Deshawn flipped me over onto my back. After licking my semen from my
body, he folded my legs back and started fucking me again. I reached down
and started masturbating. I edged myself, but slowed down until he told
me he was going to cum. When I climaxed, I shot a load all the way up to
my upper chest. He flooded my guts with his man milk.

We fucked throughout the night, and I fell asleep in his arms. We both
had to work the next morning, but he kept sending me dick pics throughout
the day. It was hard trying to stand and teach with an erection.

When I got back to my hotel room, I opened the door to find Deshawn lying
naked in my bed. He has his dick in his hand and was twirling it around.
I dived into bed and took his manhood into my mouth. His dick tasted
delicious. The head was slick with precum and I sucked on it like a
popsicle. After cleaning the head of his cock for a bit, I started
licking and sucking on his rather large and smooth ball sack while
continuing to stroke his massive cock.

"Ohhhhh...yyyeeeaaahhh...mmmmmm," Deshawn moaned.

I licked around his balls one last time and then up the length of his
shack before swallowing his cock. It hurt my throat slightly, but I was
able to take nearly the entire length down my throat.

"Fuck, man!" He exclaimed, "Not many could take that much."

`No. Not many,' I thought as I felt my mouth and throat stretch. I
deepthroated him a few times before working over the head again. I had
been blowing him for about 5 minutes when he finally exclaimed that he
was getting close. I had started to swallow his cock when I felt his body
spasm and he coated my throat with his milky goodness.

I thought we were going to spend the rest of the day fucking, but Deshawn
said that we were going out. We went to a popular gay bar on Halsted. We
spent a few minutes getting drinks at the bar before dancing together. A
few guys came by and said hi, then Deshawn dragged me to the backroom. I
was drunk by this point and felt flirtatious. I was groping Deshawn; my
hand hand found its way into his pants and stroked his monster. I felt
multiple pairs of hands feeling me up.

I was standing there thinking something felt amazing when I looked down
and some cute twink in leather had my dick pulled through my zipper hole
and was sucking on it. Several bears were standing around us with their
dicks out, slowly stroking them. When I blew my load, one of them dragged
me over and bent me over. He pulled my pants down exposing my ass. I put
on a jockstrap so he didn't have to take off my underwear.

I felt the tip of a large cock push against my sphincter. I relaxed and
pushed back, this man's hog sliding right in. He fucked me hard for a
few minutes before he blew a load into my rectum.

As soon as this first dick was out of my ass, a second one shoved in.
None of them were as large as my co-workers or Deshawn so I easily took
them. Two. Three. Four. Five guys fucked me before I was allowed to stand
up again. I could feel their semen trickling down my thigh.

I found Deshawn in the corner of the backroom. He was naked and sweaty.
Without a word, I grabbed his semi-hard cock and sat down on it. With
that much jizz in my ass, I easily glided up and down his rod. He reached
around and played with my nipples as we fucked.

"I'm surprised that place doesn't get rated by the police," I said
later as we walked down the street from the bar.

"I'm not," Deshawn said laughing, "One of the guys that fucked you is
a cop."

I was going to feel in the morning, but what a night.