Quick Trip to Chicago

By Arch Hopkins

Published on Nov 20, 2024

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Quick Trip to Chicago

Awesome Art

This is a true story that happened to me many years ago. As it floated through my mind, I decided to post it on Nifty.

Please remember to contribute to Nifty to keep it alive. I'd appreciate your comments on this story or any other of my stories under prolific author Awesome Art. My email is archhop14@gmail.com

My Fling

There was a seminar in Chicago that I had to attend. It started at 1:00 and ran for the afternoon. I live about 100 miles west of Chicago so the two-hour drive is not bad. I started out about 8 AM so that I could have a relaxing drive and maybe a couple hours to enjoy downtown Chicago before the seminar.

I traveled east on I 80 and then decided to stop at the rest area before I took I 55 north into the city. It was a lovely sunny spring day. At the rest area, I parked and strolled to the restroom. Not too many people were around but I noticed a very handsome younger man approaching me down the sidewalk. He was about 35, about my height, blonde, and a bit more of a robust body. He was neatly dressed in a dress shirt with a tie and some well-fitting dress slacks. Of course, he caught my eye as I stared a little too long for polite company.

What surprised me was that his eyes were locked on mine and didn't look away as we approached. As we passed, we nodded and smiled at each other. I was about 55 at the time so I didn't expect this younger man to show much interest in me. After we passed, I turned quickly to get a glimpse of his backside as he strolled to his car. He was very fit and his pants hugged his full ass perfectly. Just as I was turning back to continue to the restroom, I saw him turn toward me and smile broadly. I guess we were connecting in a provocative way.

I entered the restroom and did my business, washed my hands, and checked my hair. Luckily I was dressed in a nice outfit and looked pretty damn good for an older guy. Walking back to the parking lot, I saw my man slowly getting into his car and rolling down the window. He had his eyes fixed on me, so I didn't shy away but walked right past his driver's door. He smiled at me and greeted me with a pleasant "Good Morning". I responded in kind and asked him where he was headed. He responded "Chicago".

I stopped by his door to see if we could have a little chat. Surprisingly, he didn't beat around the bush but said he had been watching me and wanted to meet up. He said he liked my looks but, then when he saw my ass, he wanted to fuck me in the worst way. I was shocked by his lack of caution but didn't run away.

I replied, "Wow, I'm shocked. You are a great looking man but I'm surprised you're interested in me."

He replied, "I know what I want and I want that hot ass. Where can we go to get it on?"

"Well, I don't usually drop my pants in the parking lot and besides that, I'm not a bottom. I'm tight as a drum and prefer oral exchanges."

He said, "Let's exit at the next interchange and see if we can find a quiet parking lot. Follow me."

Although I was surprised by his forthrightness and concerned for my safety, I followed him for a couple miles and exited into a large, fairly empty parking lot. He got into my passenger seat and started undoing his pants. I then said, "Not so fast. You really turn me on but I'm not willing to be your bottom. Pull out that cock and let me have a taste."

Joe undid his pants and opened his shirt. His chest was furry and chiseled and his briefs were bulging. I looked around and then went down on his hefty cock. It was a gorgeous cut cock with a bulbous head. He had about seven very thick inches. He groaned wildly as I worked his cock up and down and felt his full hairy balls. Then he said, "Stop. I don't want to cum now. I want to deposit it deep in your ass. "

I sat back up and told him again that I wasn't a bottom and where would we do the deed even if I were. Joe said, "I am just dying for a hot fuck and you are exactly the type of man I want. You're mature, handsome, articulate, and hot. You have the ass I have to have. Let's go to the next exit and I know there are some inexpensive motels there."

Without my confirming anything, he jumped out of my car and started to drive out of the parking lot as he waited for me to follow. I was at a loss as to what to do but, by this time, I was thoroughly under this stud's spell. I followed him as he drove to Motel 6 and got out to get a room. Soon he reappeared and said, "room 231."

As we entered the comfortable room, not much was said. He went to the bed and pulled down the blankets. He sat down on the bed and told me to slowly undress as he watched. I removed my shoes and socks and then my shirt. He hummed in approval and then motioned for me to continue. Off came my pants and I stood there in my tented boxer briefs. He bid me come to him and he slowly pulled down my briefs. "Okay, nice cock. I wish I had time to worship it but we have another project at hand." He gave my cock a quick kiss and then pushed me away and told me to turn. He started growling and grabbed my buns. He dropped to his knees and kissed my ass all over. Thank goodness I had just jumped out of a long cleansing shower. Then he told me to lean over as he licked my hole and then slipped in a finger. I resisted some and he said, "Don't resist me. It is no use. I'm going to have this perfect ass so just try to relax and enjoy it."

Just so you know what he was observing, I'm about 5'10", 180 pounds, with a light dusting of golden fur all over my chest, legs, and arms. When hard (and I was very), I'm a solid six cut inches with a lovely mushroom head. As Joe confirmed, I have a full, shapely ass. Although not usually a head turner, I've had my share of hot men pursue me. I've learned my red hair often attracts men so I take special care to always have it perfectly groomed.

He quickly shed his clothes and pushed me back onto the bed. He ran his hands all over me and cuddled up on top of me. We rubbed our cocks together and there was an abundance of pre-cum between us. He then told me to roll over and he grabbed the tube of lube he had nearby. He massaged my back and whispered into my ears as he nibbled and kissed my neck. By now, I was on fire and ready to let him have his way. He pulled back and I felt his big cock head pushing at my hole. "Don't fight it. I don't hurt my bottoms. In fact, they always come back for more. Take a deep breath and push out. "

I should give you a better picture of Joe. He was about 35. He stood about six feet tall and probably carried about 200 pounds of well-muscled flesh. He had dark brown, neatly trimmed hair and piercing brown eyes. He was very handsome and carried his body in a beautiful manor. Once he stripped, I admired his big, hairy chest and prominent nipples. His legs and arms were hairy and strong. His cock stood up at a 45-degree angle and was average in diameter and about seven inches. He too was cut and his head tapered to a sharp end. His balls hung tightly and full.

Surprisingly his slippery hot cock breached my sphincter and he was lodged in me a couple inches. Again he lay on my back and this time he was biting and sucking my neck. Oh no, that feels so hot but I can't go to my meeting and home with a big hickey. He brought my tender skin to a point and then backed off. "Ready for more?" I replied out of breath, "yes."

Now the steady slide began. He backed out some to relube but was not letting up. I protested and groaned but he kept up his assault. Soon I felt his hairy pubes pushing against my ass. I have been fucked before and it always was uncomfortable for me, but I still came back for more. My tops were a variety of sizes and shapes but none very big. Joe was the biggest I've had but it hurt the least. He was a magic fucker. Joe started sliding in and out and I started moaning more and more. He adjusted his angle some and soon my prostate was being pushed here and there. Without knowing what was happening, my cock exploded all over the sheets. Joe yelped as my constrictions grabbed his member. Suddenly he was pouring his seed deep in my ass and I could feel every pulse.

We lay there for a few moments as we came down from that great high. He rolled off me and cuddled up to me as we exchanged a chaste kiss. "I knew you were who I needed," he whispered.

"I need to get going; I have an 11:00 appointment." Since it was only 9:30, I begged him to stay and cuddle some more. I urged him to roll onto his belly, as I climbed on his back into massage position. He groaned as my fingers did their magic on his neck and shoulders. He begged for more so I worked down his back, massaging his spine and ending at the top of his ass. He lifted his ass in anticipation so I firmly rubbed his strong and abundant ass cheeks. He spread his legs which I felt was an invitation to explore his crack. I put my face down there and licked his crack and tongued his hole. He was now loudly groaning.

Suddenly he pushed me off and rolled onto his back. His cock was again fully aroused and leaking abundantly. "I need more," he said as he grabbed me and pushed me onto my back. He grabbed my legs and pushed them up to my chest as he climbed between them. Since I was well lubricated with the lube and his abundant cum, he quickly slipped into my stretched hole. I was shocked at the suddenness of this move but realized I was in the possession of a strong macho top. After bottoming out in my ass once again, he slowed down and leaned into me deeply. It was magical and I was deeply in lust. He then started to slowly rock in and out. Both of us were groaning in ecstasy. The pace picked up and soon he deposited another load deep in me.

He kissed me again and stated, "I'm not usually a kisser, but you deserved that for being such a perfect bottom." I smiled warmly and tried to hold him tightly to me as he withdrew, looked at his watch, and quickly left the bed. He cleaned a little in the bathroom, dressed, and was on his way. While he was cleaning up, I slipped my card and my private phone number into his pocket. Unfortunately, I never heard from Joe again but was happy he had persuaded me to join him for a morning delight.


Please let me know your response to my story. archhop14@gmail.com

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