Hot Sex, Chicago Style

By Miles Long

Published on Apr 12, 2005

Gay

This is a true experience. Send comments to miles_long@hotmail.com

I put the do-not-disturb sign on my hotel door and slept late. When I finally did get up I was still pretty worn out. My cock was sore from getting sucked so much, and my jaw and asshole were sore from the stretching they'd received the night before. Still, I wanted to get the full Chicago experience, because I knew I wouldn't have all this free time for a while in this great city.

After a long shower I found a restaurant in the hotel still serving brunch and enjoyed a leisurely meal. I went back to the room and pulled on a black t-shirt, my tightest jeans and a pair of work boots. I drove the rental car over to North Wells street, looking for parking near a famous theatre that Kevin had written down for me. I finally found a place to park, then walked to the theatre. At first I went past it because it was a non-descript entrance, but I did find it and paid my entry fee.

First I explored the place. Right in front was the theatre, with a big screen showing porn and at least a dozen rows of seats. Beyond that was a hallway, with a circular stair leading up to the second floor, where I'd been told most of the action happened. Off the hall was a small bathroom, and then it opened to a courtyard that was something of an outdoor maze. I went upstairs. There were a number of guys cruising, probably a good number for the middle of the afternoon on a summer Saturday. It was fairly dark, but you could see pretty well. Nearest the stairs was a series of private booths, many with glory holes. At the back was a video area, with a small TV showing porn. At the front were two rooms, one with a sling and one labeled as a "blow job" zone.

I went back down to the theatre. I was startled to see a woman had come in and was sitting on the asile toward the back. I sat down right in front of her, and as I did I realized it was actually a guy dressed in a blonde wig, sheer blouse, short red miniskirt and thigh-high fishnet hose. I tried to concentrate on the movie. It was a pretty good scene. A guy had a big-dicked young blonde boy tied spread-eagle to a bed and was having his way with him.

The CD behind me began rubbing a long, nylon-encased leg on the outer armrest of my seat to draw my attention. After a few minutes of that, he leaned forward and whispered "Why don't you come back and sit with me?" I rose and moved back a row, sliding past him into the seat beside him. Almost immediately he took my right hand and placed it on his thigh. I felt the bare skin along the edge of the hose and the heat of his cock. Then he started feeling around in my crotch. When he finally touched my hard dick, he cooed his approval. He massaged my cock through my jeans for a few minutes as we both started at the screen. Then he leaned over and whispered "Follow me."

The CD rose and headed through the doorway. I thought he was heading upstairs but he kept walking down the hall and into the courtyard. I followed into the far corner. He sat on a small bench, straightened his skirt and reached for me. In seconds he had my cock out and was licking the head. It was almost as strange as fucking in a public park; I could hear the sounds of the city all around and the warm air felt great, but in this shaded, walled courtyard no one could see us, and there were no other theatre customers around. My cocksucker was doing a fabulous job, working down the length of my shaft with his long tongue and licking my balls as well. He then began to deep-throat my length. Suddenly he stood, spun and raised his skirt, exposing a very nice round ass. Without a word passing between us I stepped in close and slid my cock into his tight channel. He threw his head back as I sunk my 11 inches into his ass. I braced my hands on his slim hips and began fucking with long, steady strokes. My balls rose quickly, at least considering what I'd enjoyed the day before. I shot a huge blast into his bowels, both of us groaning. After resting a moment with our bodies hunched together, the CD adjusted her outfit, thanked me with a quick kiss and disappeared.

The edge of my horniness was off, but I was still eager for sex in the dark play area upstairs. I climbed the stair and went to the back part of the second floor. In the video room two very tall and well hung guys, one black and one white, were sitting on a platform along the back wall taking turns sucking each other's cock. A small crowd had gathered to watch this excellent live show, and I joined it. Some of the guys had their cocks out, stroking. When I pulled mine out the young college jock standing next to me looked over and did a double-take. He swiftly manuvered me over to the platform on the side of the room and quickly put his head in my crotch, sucking cock. Now several guys stood around us, watching him make a show out of sucking my big dick. I could still see the twosome along the back wall, and they were still going at it. Eventually I was able to ease my cocksucker off my hard shaft and let someone else join him. An older guy had been practically drooling over my cock, so I let them share. They seemed intent to coax a load out of me, so after a while I came, and both got a taste.

I zipped up and moved toward the opposite end of the building. In the room on the left a guy was on his knees sucking anyone who came close enough. He had three guys lined up in front of him and was giving all of them a heck of a blowjob. As I watched someone reached for me out of the shadows. He felt my ass and dick and pulled me close for a kiss. I lost myself in the kiss for a moment, but then moved on.

In the other room a weighlifter type had shed all his clothes and was positioned in the sling. He was filled at both ends, and there was a lines of guys waiting their turn at both his mouth and his ass. I pulled my dick out and joined the scene. Several guys bent to take my cock in their mouths as we watched, and I returned the favor for several of them. Eventually I plowed the guy in the sling as a growing crowd urged me on. I pulled out and shot a big thick rope of cum across his six-packed stomach, as several others had done. As another guy took my place, I reached for the weighlifter's cum spattered dick. After a dozen strokes he fired his own blast across his stomach and chest.

After that, I wanded back down to the first floor and out into the street. The brighness of the day -- even in late afternoon -- was a shock my eyes after spending almost three hours inside. Now there was only one more place on my list to experience.

More to cum...

Next: Chapter 4


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