One of my responsibilities as a low-level supervisor at an investment firm is to attend quarterly meetings at the regional office in Chicago. I am always one of the younger people at these events and, to be fair, I am also the lowest-ranking person from our firm who attends these meetings. While the top executives are pampered and put on an airplane at the company’s expense, I am afforded a partial day off with pay to make the six-hour drive. The worst part is that the event always ends on Friday afternoon. That always leaves me having to either make a late drive home on Friday or spend a large part of Saturday doing so.

These particular quarterly meetings, I found myself looking forward to, however. More specifically, I was looking forward to what I had planned to do after the close of the day on Friday.

As a closeted gay male, I have always struggled to present my true self to others. In the time leading up to this meeting, however, I found several other men that I had become online friends with. One of them spoke about an underground club that was located in Chicago. He had moved away from the area but claimed to have frequented it many times. That was my goal for the trip. I needed to find the courage to actually show up to the club and see what kind of fun I could get myself into.

The meetings that week went the same as always. They could simply record a single meeting, play it back to us every quarter, and save us all a lot of hassle. After Friday’s meeting, I grabbed a bite to eat and headed back to my hotel room to prepare for the night's events.

While I wasn’t sure if I could actually go through with it, I had to prepare for everything. I had brought my arsenal of cleaning tools and sex toys to make sure that I was absolutely ready for action. After some extensive preparation, I put on my tightest low-rise, skinny jeans and a long-sleeved, pink mesh shirt.

Rumor had it that if you wore red, it meant that you weren’t available. If you wore blue, it signified that you were a top. Green apparel demonstrated that you were versatile, and pink meant that you were a bottom.

I left the hotel with only my wallet and the key card for my room as I searched for this mysterious club. After taking a taxi to a nearby intersection, I started to search around on foot. It was after eleven o’clock, so things should have been getting cranked up by that time. I paced up and down every side street I could find until I nearly gave up.

Then I saw two flamboyantly dressed men holding hands and walking with purpose. I decided to follow them and see where they were heading. They entered an unmarked warehouse building that I had walked past several times. As the door swung open, the sounds of distorted dance music filled the air. I had found it!

I waited a moment before entering the door. Two burly security guys stared me down as I stammered through the code that I was told that you needed to say, “I’m here for the rave.”

Whether that part was necessary or not, the men checked my identification before frisking me thoroughly. Their main objective seemed to be checking for weapons and cell phones. Fortunately, I had left my phone back at the hotel for fear of getting it stolen. After paying a robust thirty-dollar cover charge, I was ushered into the middle of the dance floor and there was no turning back.

The club, like most warehouses, was a long rectangular box. At one end was a DJ and the dance floor. Next was a lounge area with a series of risers so that patrons could get a good view of the dance floor. Behind that was the bar and a sizeable roomed-in area with restrooms.

I made my way past the dance floor as quickly as possible. The strange looks that I had received while walking the streets of Chicago looking for the club were gone. I was just like everybody else. Although I received some flirty looks, nobody approached me.

A quick trip to the restroom was surprisingly much more tame than I would have imagined. There were some people milling about, but it wasn’t the sex orgy that I had imagined. As I left, I noticed some couples making out in the hallways, but I didn’t see anything too extreme. After making a quick stop at the bar to grab a cosmopolitan, I started to circle the lounge area aimlessly.

“Hey, You!” I heard an effeminate voice shout several times. It was really difficult to pinpoint where it was coming from over all of the noise in the club. A waving hand led me to the source of the shouting.

This person, who I later found out to be named Graham, was seated in a semi-circular booth with his partner and another couple. He was kind enough to invite me to sit with them. I’m pretty sure he just felt sorry for me.

While the other couple seemed nice, as well, I mostly talked with Graham and his partner, Tad. They were probably ten years my senior and they were regulars at the club. Because of the noise, I couldn’t really communicate with the other couple very well since they were further away.

They picked up on the fact that I was new to the scene and filled me in on how things usually went down. For instance, there was a separate room next to the restrooms for hookups. Apparently, there were several little cubicles in there for those seeking privacy. As the night went on, those who liked to be watched tended to line the hallways.

Graham was a proficient talker. He started to go on about the special parties that the club sometimes has, such as the beach-themed parties where patrons are encouraged to wear their sexiest swimwear. I imagined the dance floor full of men in their Speedos and thongs. There were also sleepover parties, seasonal parties, and many other intriguing themes.

I had been chatting with the guys for more than an hour when I saw a giant African-American male on the dance floor. He towered above everyone else and I had to ask Graham if he knew that man.

Graham casually responded, “Yeah, that’s LT.”

I knew that I had heard of somebody named LT before, but I couldn’t remember where.

“The football player?” I asked.

Graham laughed at me, before explaining that that particular LT had passed away years ago. Apparently, this was the All-Star basketball player, Lamar Thomas, who I had never heard of before.

According to the guys, LT played for Sacramento and whenever he was on a road trip to Chicago, he would frequent the club. He usually showed up pretty late, probably after a game in Detroit, Milwaukee, or some other nearby franchise, and would pick up somebody and leave.

Graham suggested that I approach LT because I was his type. Even the much quieter Tad agreed. That clearly wasn’t going to happen, but it didn’t stop me from keeping an eye on him, anyway.

It took a moment for me to pick up on it, but LT was wearing a red leather jacket and matching pants that were clearly Michael Jackson-inspired. He was bare-chested beneath the jacket and the pants were tight enough that they didn’t leave much to the imagination. LT was adorned with gold chains, bracelets, and rings.

As we continued to chat, I took my eye off the action just briefly. Graham was talking about all the celebrities, athletes, celebrities, and politicians he had seen in the club. He even claimed that one politician, in particular, had even run for president. Just as I was about to attempt to get more details, I heard a deep voice shouting, “Excuse me!”

When I turned around, I found myself staring directly at an intricately detailed outline of LT’s cock. There was no doubt in my mind that he had “gone commando.” I craned my neck upward to attempt to make eye contact with him. LT outstretched his hand and asked, “Do you want to join me?”

Graham covered his mouth and warbled at me, “Told you!”

It was my first offer of the night and although I was terrified, I delicately offered my hand and was whisked away to the dance floor. I am not very comfortable on a dance floor usually, but I found that I was even more uncomfortable on this dance floor with everybody watching me. It felt like they were, at least.

I don’t know exactly how tall LT was, but I was staring at his chest. Granted, I am only 5’8”, but he had to be approaching 7’ tall. We danced through a couple of songs before LT whispered into my ear.

“Do you want to go back to my suite?”

I nodded affirmatively, and LT produced a cell phone from his inside jacket pocket. He plugged the opposite ear with his finger as he shouted into the phone. LT grabbed onto my hand and led me to a side door. He pushed it open and just a few steps away were a limousine and a driver. The driver opened the rear passenger side door and I climbed inside, followed by LT.

Within seconds, LT had opened up the front of his jacket and was loosening his pants. He pulled his cock out and briefly stroked it before grabbing my head and directing it downward. LT’s cock firmed up quickly and I was struggling to handle its girth, but more particularly, its length. Even with my mouth wide open, I could scarcely take more than the head.

I heard a humming noise and LT started talking to the limo driver. He had lowered the tinted window and left the both of us exposed to the driver. He held his hand on my head, not in an attempt to force me downward, but to prevent me from sitting up. It seemed obvious that he was enjoying showing off to the driver. The trip only took a handful of minutes before we pulled up at a hotel that I later found to be called “The Peninsula.”

Once again, LT didn’t use the front entrance. The driver stopped in front of a random, unmarked door before making a quick call. After a brief wait, he quickly exited the limo and scurried around to open the door for us. Before we could even get out of the car, the side door swung open, and somebody from the hotel staff was waiting for us.

LT climbed out of the limo first, not bothering to even conceal his weapon. In his defense, with it fully erect, there was no way that it was going to fit back inside his pants. Neither the driver nor the doorman even batted an eye at the sight of this giant man with his massive cock exposed, and his boy toy for the evening entering this fancy establishment.

Once we were inside the door, the driver handed us off to the hotel attendant. He led us to an elevator that clearly wasn’t the primary one. It required a key to open and operate. He led us to LT’s suite and opened the door for us.

Once inside, LT grabbed me and slung me against the back of a couch. He grabbed onto my jeans without even unsnapping the front and yanked them down aggressively. They scraped hard against my body, mostly because they were very tight. Before I could gather myself, LT got down on his knees and buried his face in my ass. He spread my cheeks with his massive hands as he eagerly tongued my hole. Just as I started to get into it, LT stopped and said, “Alright, you can go now.”

To my surprise, the attendant was still standing in the doorway. In the excitement of the moment, I hadn’t even realized that he was still there. It was becoming increasingly apparent that LT liked to have others watch him in action. Luckily for me, I was pretty sure that this was the last time that I would be put on display.

LT resumed the rim job as sounds of his lips smacking and slurping echoed through our small palace. He suddenly stopped and got to his feet. I was sure that his aggressiveness was going to continue and that he was going to ram his massive rod inside me unannounced.

To my surprise, LT stepped away. He entered a nearby bedroom area that had a large sliding entryway. He removed his jacket and sat at the edge of the bed as he started to peel his pants off. I took the hint and removed my clothes, much of which were already partially off.

LT pointed at the bar and told me to help myself. He asked me to grab a bottle of champagne from the refrigerator, as well. I decided that champagne was fine with me, so I just grabbed two glasses and returned to the bedroom. After pouring our drinks, we enjoyed them briefly.

As LT got to his feet, I could tell that he wasn’t messing around anymore. I was getting nervous because I simply didn’t know how well I was going to be able to handle his massive size.

I owned a handful of different-sized dildos. Normally, I would start with the smallest and gradually work my way up to the largest. Although LT’s cock was roughly the same thickness as my largest, he was much longer. To make things worse, I couldn’t handle the length of the toy, either. I feared that without a warm-up, this was going to be a real challenge.

LT handed me a bottle of lube and I did my best to lubricate my ass. I even took the initiative to slather his cock with lube, as well.

He grabbed me, bent me over the edge of the bed, and spread my legs wide. As he lined me up, I could feel the head of his cock press against me. He pulled my hands behind my back and pinned them together, leaving me completely under his control. I felt his hips surge forward until his cock popped partially inside me. The initial discomfort wasn’t unbearable, but it certainly left me gasping for breath. LT took it slow and easy, at first. Within a few minutes, I was pretty comfortably taking about half of his length.

LT stopped abruptly. He withdrew his cock and hoisted me into the air before dropping me onto my back. Holding my legs upright, he spread them apart and positioned his cock so that it hovered over mine. To say that there wasn’t much of a comparison would be an understatement. He chuckled proudly as he swung it back and forth so that it slapped against my thighs.

With his right hand gripped tightly around the base of his cock, he forced it inside me once again. I smiled at him as if to say, “I don’t care it is big. That’s how I like them.”

My arrogance would be short-lived, though. LT reestablished his dominance very quickly. Pinning my legs against his torso, he quickly gained depth until he started to hit an uncomfortable spot that I was quite familiar with.

To be honest, I’m not exactly sure what it is. I think that it's a sharp bend in the “tunnel,” but it is pretty hard to know for sure. I have pushed past it a couple of times with my longer toys, but when I did, there was an awkward sensation that made me quickly back away.

LT started to bang the head of cock against that spot over and over again. With each collision, I let out an even louder grunt. I think that my distress only fueled his fire, though. He looked at me with a sinister smile and said, “Yeah, I’m going to find a way to get all of the way inside you.”

I swallowed hard as I realized that I was going to get pushed beyond my previous boundaries. LT shifted ever so slightly with every thrust of his hips. It was almost as if he was trying to pick a lock and he just needed the right combination of angle, force, and momentum. My grunting continued for what felt like an eternity until it finally went in.

As LT instantly gained several inches of depth, I gasped for air. That awkward sensation that I had felt previously had returned, but I couldn’t stop it this time. I squirmed in LT’s grasp with little result. As my body contorted, I could feel how rigid my cock had become. I felt it throb as it begged for some attention, but none would be afforded it.

I sensed that LT could feel something different about the new territory that he had discovered, although I don’t know in what form it presented itself. He toyed with my body, never backing away far enough to free his cock from its new discovery. The sensation remained sharp and uncomfortable, but not in a painful way. I didn’t even realize it at first, but I had become increasingly loud. My cries mimicked LT’s every movement.

The look in his eyes confirmed that he was getting exactly the response that he was looking for. It was clear that I wasn’t the first white boy that he had done this with. This was what he was seeking all along. He was determined to stretch out my ass in every way possible and leave my body forever molded in his image.

LT was pushing his cock even deeper inside of me. I finally felt him start to bottom out, but not before he was bumping against yet another “wall.” He started to speed up, causing me to cry out louder than ever before. The combination of the strain, that awkward sensation, and his cock as it doinked against whatever new barrier he had found left me writhing on the bed. I tried to grab onto my cock, but he pulled my hands away.

As LT sped up, both of us were screaming like madmen. Then came perhaps the most unimaginable part of this story. LT let go of my hands and extended his body forward. Standing at the foot of the bed, he grabbed onto the headboard and used it for leverage. As his body crashed into mine, I realized that my hands were, once again, free.

I grabbed onto my cock and started stroking furiously. Within seconds, I was showering my chest and midsection with cum. LT had ceased movement by that time and I felt his cock throbbing inside me. I could feel a warm, wet sensation as he pumped his load nearly a foot deep inside of me.

LT slowly backed away. He lifted my backside into the air as his cock broke free. I could tell that he was admiring whatever state he had left my ravaged hole in. Then I felt a cold blast of air as he blew into my gaping ass, causing it to clamp shut. He told me that he wanted to keep every drop of his load inside of me.

He went to the bathroom and returned with a couple of towels. After a quick cleanup, as well as finishing the bottle of champagne, LT said that he needed to get some sleep because he had an early practice in the morning.

We cuddled up on the bed as I found myself wishing that we had time to go again, although my sore ass probably would have shut that down in a hurry. Nevertheless, I was disappointed that my adventure was already over and that I was going to have to go back to my normal, boring life. Fatigue caught up to me, though, and I did manage to fall asleep pretty quickly.

When I awoke, LT was already gone. He must have either just grabbed his stuff and left, or headed to one of the bathrooms at the other end of the suite because I didn’t hear him. I did find a handwritten note that simply said to let the front desk know when I was leaving.

So, I had to put on my wrinkled club clothes and head into this prominent hotel’s lobby. The staff, once again, were unfazed by my appearance, although I am sure they all had a good laugh after I had left. To my surprise, LT had arranged for a car service to take me back to my hotel, which was a relief. I didn’t really know where I was and didn’t have much cash left in my wallet.

On my ride back to the hotel, I couldn’t help but think about how much fun I was going to have at the next quarterly meeting.