August 9, 2025

Sex has been coming to me in fast waves I could hardly keep up with it. I’ve become so invested and preoccupied with finding guys online, an addiction that I’ve realized was starting to separate me from the real world. The city has thousands of men who aren’t on online hookup sites, so I decided to venture out and explore the vast array of men the city offered.

Making eye contact with anyone I found attractive while walking on the sidewalk is always scary for me, mainly because I’d be putting myself at the risk of being rejected if the other person doesn’t reciprocate. Then I came up with a better, risk-free way to do it. Walking on the sidewalk, instead of staring directly at the person, I’d pretend to be window-shopping when I’d actually be carefully watching the oncoming person’s reflection in the glass to determine whether or not the attraction was mutual. This technique worked, but only occasionally since I eventually realized that my method only proved to be effective if we were both walking at a similar pace. If the pace differed, I’d often end up missing on my chance of making actual, direct eye contact with the person.

I met Frank at an art fair. I was instantly drawn to his paintings, all done in pop art style and featuring semi-nude male figures either in or out of swimming pools. He had a unique style and his personality oozed with charm. We exchanged phone numbers and decided to meet the following week. Since he knew the city better than I did, I asked him to pick where we would go.

Walking arm to arm with a man I’m marvelously in love with used to be a fantasy of mine. Ever since I became a cynic, though, that romantic side of me has totally vanished. The world has become flat in my view. Frank and I strolled down the streets of River North and entered art galleries and luxurious furniture stores. Inside, we pranced through the different sections, lingering far too long in some and making out and groping each other’s hard-ons in quiet, empty corners. It was fun and exciting to see how far we could go before someone noticed us. Finally, at one of the galleries, an old creepy woman almost walked in on us jerking each other off in the back room. It was fun. By the end of our three-hour long tour, our stomach started to growl, so we stopped at an organic grocery store and made ourselves a salad at the salad bar. We ended the day fucking at his place and he came up with the idea of using me as his model for a series of paintings, and I was absolutely flattered to be painted by him. Although I enjoyed his company tremendously, the whole experience was put behind me the day after. I’m not sure why; I’m guessing it’s because there was no glimmer, only a superficial connection. Our romantic stroll was nice on the surface, it had only the semblance of an authentic connection. We liked each other because we only presented an ideal version of ourselves and weren’t too interested in establishing anything deeper than that.

After some hesitation, I’ve decided to give bathhouses a try since they’re known for being an easy path to sexual gratification. Steamworks has a small, isolated entrance door on the side of its four-floor building. The interior was gleaming, with an electric and futuristic feel. I walked inside and checked in with a man sitting behind thick glass window. I then proceeded and entered the establishment to the sight of a veritable buffet of men walking around in towels firmly wrapped around their waists and others, completely naked; some of them were better off with their clothes on. A few minutes into my visit, I noticed I was quickly becoming a pursee. Inside each room, I spotted individuals who fell under the five distinguished categories of guys which to me consisted of: “just-looking”, “here-to-boost-my-ego”, “cheating-on-my-boyfriend”, “only-into-fit-and-masculine” and “boyfriend-twins.” Smell of poppers was pernicious; its stench filled my nostrils. Each room had a large flat screen TV playing porn videos; from twinks to kink and everything in between. In each area, a different kind of action was happening; handjobs, blowjobs, bareback sex. I walked into one of the private rooms which door was slightly open and found a naked guy casually stroked his penis and sat next to him. He eyed me for a little bit as I enjoyed the heated, moist air before making his move; he groped my crotch through my towel and started kissing my neck. I was initially fine with it until he said he had a couple of loads in him and wanted more which I found disgusting and an instant mood killer. I pulled away and left the room immediately. Back outside, I bumped into a creepy old man hunting down a group of young boys walking towards the back area where a plethora of glory hole configurations was located. I skipped that part and went to kill some time in the sauna instead. The room was big and surrounded with frosted glass which offered some privacy. On my way there, I found two attractive men sitting next to each other in the whirlpool bath, so I aimed for the tub instead.

Dillon was tall with dark features and enough metrosexuality to be attractive and not come off as a narcissist. Michael had strawberry blond hair and an overall natural look to him. Both of them were high on drugs, but  it wasn’t too obvious. As a matter of policy, drugs aren’t allowed inside the complex, and while some were able to sneak in some, I assumed they had taken a few hits before they got there because security was tight (I was often blinded by flashlights appearing out of nowhere due to suspicious activity; an older man and a young boy were both escorted outside for solicited sex). The lights in the room were white and blue which gave it a sexy subdued look and added an overall nice ambiance. The water was crisp and hot. I sat across from them and it didn’t take long for them to notice me. After some brief eye contact, Dillon slowly reached out to me and pulled me to him. They squeezed me in between them and surprisingly, they flirted with class, their touches smooth and seductive. We fooled around for a bit before heading back to Dillon’s apartment on Lake Shore Drive. None of us really talked on the way there. Dillon was reserved while Michael was more on the shy side. In the bedroom, Michael was totally submissive. After we all got naked, Dillon watched us fuck. He seemed to enjoy the voyeuristic side of sex, ordering both Michael and I to do the things that aroused him. At some point, I felt white-hot and my cock went limb, so I moved away and let Dillon get some action while I watched, my hand aguishly jerking my cock craving to get hard again. Once it did, Dillon moved away and let me pick up where I left off. My thrusts were fast as I was eager to pump my load. When I got close, I asked him if I could ejaculate inside him, and he turned to Dillon who approved my request. I immediately did.

When Michael got up and went to the bathroom to clean up, I asked Dillon if they were boyfriends and he said they weren’t. Michael was a closeted married man who he occasionally slept with. Apparently, once a week he allows him to come to his apartment so he could get fucked by a different guy each time. What I couldn’t understand, though, was Michael’s submissiveness and total obedience to his requests. Dillon said Michael would do anything he asked him to do, no questions asked. When I left, I drew my own theory: Dillon seemed to harbor feelings for Michael, and so I knew they were once lovers. Maybe their affair ended when Michael revealed he was married and Dillon, although disappointed, couldn’t let him go. Instead, he asserted his dominance over him as a coping mechanism.

Some of my adventures included some intense drama. As I became a conveniently perfect tool for unhappy couples seeking side dishes, things became a little complicated. For instance, I’ve received a message from a guy asking for a quickie; his profile picture shows him hugging his partner. In their bio, it’s clearly listed that they only play together. I decided to mess with him by pointing out that fact, and he said his husband wasn’t around. When I told him I was only attracted to his other half, he immediately got offended and accused me of trying to wreak havoc in his marriage which I thought was laughable. To make things even worse for him, I lied and said me and his husband had sex once. I bet that made the topic of conversation at dinner that night which most likely led to an argument or maybe, an intense fight.

I’ve realized that when it comes to sex, relationships between gay men is often founded on lies and mutually accepted delusion.

Most recently, I was contacted by a guy who refused to send me a picture of him. He was hosting a sex party at a fancy hotel downtown and wanted me to attend. I was skeptical as to how authentic the whole thing was, and I didn’t hesitate to let him know how I felt. He eventually agreed to expose himself to me and followed that with an information sheet he sent me through email containing the “do’s and don’t’s”. The location was revealed half an hour before the event started, and we were to strictly bring ourselves only. 

The lobby area was swarmed with middle-aged men all arriving together for some sort of conference. They were all in black suits, unkept and exhausted. I had to wait a few minutes until all the elevators were loaded before I could sneak into one of them. We made different stops along our way to the highest floor, the elevator slowly emptying as it got there. I was the only one remaining in it when the doors opened. The floor was so quiet and moody. Looking outside the window, all I could see was blackness and all I could hear were far away echoes coming from the busy streets of Michigan Avenue. I felt like I was in some sort of spaceship, some sort of erotic fantasy. I started making my way to the room and soon, another man showed up behind the corner of his side of the corridor and started walking in my direction. Our steps got slower and slower as we got closer and closer to the suite. We met halfway and faced the door.

“We’re both coming to the same place”, he said.

I smiled and he knocked. We heard the muffled sounds of guys conversing and laughing as well as footsteps slowly approaching. I took a deep breath. The door opened.

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