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.
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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.