The Pentagon and The Castle

April 20, 2023
Ao Nang, Krabi, Thailand

“You better make it pop!” she ordered, glaring at me. I looked back at her, as she stood, hands on hips in her tight-fitting, white dress adorned with a sash that read “Bride to Be”.

I looked out at the crowd, all eyes fixed in our direction on the stage. Many cellphones were out, recording the proceedings. One of them was in the hand of my new friend, Amber, who was laughing at the situation she had helped put me in. ‘Ah, shit,’ I think to myself. ‘I’m going to end up on YouTube somewhere.’

“I’ll do my best”, I replied to the bachelorette. “But I doubt it’s gonna happen.”

Open position

It was early July, 2014. Chicago was enjoying a beautiful summer, hot enough to make swimming in Lake Michigan an attractive option, but not so torrid as to keep the residents inside during the day. Many were taking advantage of the lovely weather to attend a myriad of street festivals and summertime activities that the Windy City offered.

The Taste of Chicago, an annual gathering of pop-up street stalls offering samples of scores of favorites from local restaurants, was in full swing. The northeastern section of Grant Park had been transformed into a large tent city, the smells of bbq ribs from Robinson’s, burgers from Billy Goat Tavern, and deep-dish pizza from Lou Malnati’s wafted through the air. That night, thousands were treated to live performances by Jeff Tweedy and Lucinda Williams in the Petrillo Music Shell.

The previous evening, I joined a smaller group of maybe three hundred at Michigan Avenue, between East Congress Plaza and Balbo Drive, for a Summerdance event. Every weekend in the summer, the Chicago Park District scheduled outdoor dancing for free. At the Grant Park location, there was a semi-permanent stage and dance floor. There would be one hour of instruction on various types of dances, then a live band or DJ would play the style of music to accompany the style of dance that had been taught that evening. That evening, they were doing a focus on Haitian music and dance styles.

Chicago SummerDance Festival

Halfway through the lesson, I received a text message from my couchsurfing guests who were arriving. I gave them my location and about 30 minutes later five young women showed up on the sidewalk. I introduced them to a couple of friends who were at the dance event with me, and we invited them to join. They politely declined as they were hungry after the long drive from western Michigan to Chicago. I had plans to go to a bar later with some others, so I gave the ladies a key to my door and told them I’d meet them back at home when I finished.

How did I come to be hosting a group of five in my small studio apartment?

Two’s company, three’s a crowd. SIX?

Three days before, I was at a Mealsharing dinner party where the host was making homemade ramen soup. My friend Jay was there, along with three others in a mid-rise apartment building not far from the Loop in downtown Chicago. Normally, I didn’t bother with my cellphone at these meetups, but during a lull in the activities, I took a minute to scroll through the list of prospective couchsurfers who were visiting the city and looking for a place to stay. One young woman’s profile came up on the screen. Linda was looking for accommodations for herself plus four other women. I kept scrolling, because no way I was willing to host five people.

However, as her profile began to disappear through the top edge of my screen, something caught my attention. We had a mutual friend, Jennifer, who lived in Chicago and whom I knew quite well. I sent a quick DM to Jennifer to ask her if she was hosting her friends. However, Jennifer was out of the country visiting her boyfriend, and didn’t seem too worried about where her friends were staying. “They’ll find a hotel,” she said. “Unless YOU want to host them,” she laughed.

I knew that the ladies were unlikely to find anything even close to downtown due to the Taste of Chicago and other festivals going on that weekend. I reasoned that if they just needed a place to crash, I could possibly provide boarding for a couple of nights. I was scheduled to work early Saturday morning, so we wouldn’t really be in each others’ way, assuming they had plans to be outside on the weekend. I told Jennifer to let her friend know that my place was available if they couldn’t find anything else on short notice.

Three minutes later I got a notification and request to stay from Linda (pronounced “Leen- dah”, not “Lin- da” – very important). Her message exuded excitement at the possibility of staying with a stranger who had the friendship of someone she trusted. She would be traveling with her sister and three other young women, one of whom was celebrating a birthday on Saturday, which was ultimately the reason for the weekend getaway.

I sent her some particulars about the apartment, including information about Charlie, my lovely, yet still skittish cat. I told her that there were two queen-sized sleeping surfaces she and her party could share, and that I had my own roll-up mat that I would place in the kitchen by the door so as not to disturb them when I got up for work at 5:30am.

Since they would be arriving Friday evening and I already had dinner and dancing planned, I gave them directions on where they could park on S. King Drive outside my apartment complex, and how to take the bus into the downtown area. This is how I came to meet them on the sidewalk at the corner of Michigan and Balbo at 8pm.

We gon’ party like it’s your birthday

I awoke early the next morning. The summer sun was just beginning to peek over the blue waters of Lake Michigan, bathing the tops of the taller skyscrapers in an orange-pink glow. I dressed as quietly as possible in the bathroom before placing a bit of food in Charlie’s dish and slipping out the door. The ladies were sleeping soundly, having come in late the previous evening. They had mistakenly gone to the wrong building at first, trying the key in the lock of unit 1804 unsuccessfully, until they were surprised by the occupant who was wondering why five young women with luggage (and a box fan that Amber inexplicably brought?) were trying to invade his apartment late at night.

My half-day at the machine shop was uneventful and quiet, with only a few coworkers around. I drank my coffee and did a couple of crossword puzzles while my CNC milling machine performed its programmed routines. I wrote myself a reminder note to drive up to Molly’s Cupcakes on N. Clark Street after work to get one of the best chocolate confections in the city for Nia, since it was her birthday. Around 11:30, I received a text message from Linda, letting me know that they were grateful for the accommodations, informing me that they were heading out to explore downtown, and asking me if I would like to join them that night going to a club.

Up to this point, I had very little experience with clubs. The only time I remember being in a club before this was back in 2004 when I was on a large cruise ship in the Caribbean Sea with my wife and kids, her extended family, along with several dozen other Jehovah’s Witnesses who all signed up for the 7-day boat holiday through the same travel agent who accompanied the group. There was, of course, a club or two onboard the ship, and we visited. Why we felt it was okay to be doing something that we would not ever do on land back in our hometowns, I don’t know.

I watched many “good Christians”, who would otherwise be dressed very modestly and putting on a front of righteousness, now in the club, “getting low” and “backing that thang up” late into the night as the hip-hop music thundered from the speakers, the lyrics filled with explicit references to sex and drugs. While I really didn’t care anymore personally, I found the blatant hypocrisy amusing. It wasn’t as much fun to me as I had imagined it might be, and I only went the first night. I preferred to go to my cabin early so I could wake up and enjoy the morning without being bothered with my wife who stayed up late with her family enjoying the entertainment venues.

The invitation to go to a swanky club in the River North district of Chicago, therefore, was both intriguing and intimidating. The Castle, as the former Excalibur had been renamed two years prior, had a reputation of being one of THE spots to be seen. I worried a bit about my ability to blend in. But I said, “yes”, because it was going to be a new experience for me, and I wasn’t going alone.


When I am told that something will happen at a certain time, I still am naive enough to believe that the schedule will be kept. I have been told it’s my Germanic genes that makes punctuality a part of my identity, and I am still confounded when others have a different understanding about what the rotating big and little hands are there for.

So when I was informed that 10pm would be the time to go to the club, I was ready at 9:30, dressed in my best club outfit – a pair of black dress pants, a black button-down shirt, black leather belt, black socks, and black shoes which I polished up for the occasion. I may have even been wearing black underwear. I was Johnny Cash, sans the hat. I sat in the chair, patiently waiting for the ladies to come back from their excursion downtown. I gently kept pushing Charlie away with my foot. I didn’t want to get his white fur on my dark clothing. He finally jumped up on the couch and glared at me from across the room.

At 9:55, I heard the key turn in the lock, and the five young women flooded into the apartment. Still in shorts and t-shirts. Not dressed for the club. I chided myself for my mistaken belief that we would be leaving at 10. Charlie jumped up and ran into his hideaway in the small closet that was accessible only from the bathroom. While he had learned to like people and was friendly enough when I had guests, five boisterous strangers at once was still a bit for him to handle.

Linda took a look at me and stated the obvious. “Oh, you’re ready already!” I smiled back. Yes, I was ready. And I was secretly gratified to know that she thought I looked ready to go to a club, because I wasn’t entirely sure that my attire was fitting for the occasion.

Linda’s sister, Nadia, cheerfully predicted that they would be ready in 30 minutes. I smiled again, this time mainly to myself. In my experience, when a woman tells you she’ll be ready in a certain amount of time, you should multiply that time by a factor of three. There were five of them, so I understood that the minutes from that point until we walked out the door could increase exponentially. I was happy that I had eaten dinner already. I grabbed a book and tried to distract myself so as not to distract them with my presence.

Over the course of the next two hours, the five ladies took turns showering, using my iron, and asking each other about their outfits. Valiant efforts were made to put on makeup three at a time in front of the sink mirror in the small bathroom. Somewhere during this time Nadia mentioned to me half-jokingly that if I was going to be hosting women a lot, I needed a full-length mirror. She made a good point. Little did I know that two days hence, that exact item would magically appear downstairs in front of the karmic dumpster.

Left to right: Nia, Linda, and Desiree, all dressed up and waiting to go.

The transformation of the women was astounding. Already attractive in their summer street clothing, the addition of makeup, hair styling, and clothing designed for a night out on the town, they looked ready for the covers of magazines. Linda and Nadia had emigrated from Colombia with their parents several years before, while Nia was Venezuelan by birth. Their strong Latin genetics had created a natural beauty only enhanced by their expert level knowledge of how to ready themselves to be seen at a club.

Their other two companions were striking as well. Amber looked the part of the stereotypical All-American ideal – tall, willowy, with blonde hair and blue eyes. Rounding out the five was Desiree. A French citizen by birth, her heritage was Laotian, and her southeast Asian features would garner second glances anywhere she went. And for some reason I never understood, she insisted on being called “Your Grace”, “Your Highness”, or any variation of “queen”, “empress’, etc. I knew it was an inside joke, but the titles seemed to fit.

My vivid descriptions of the women isn’t out of any type of salaciousness. It’s important for you as a reader to understand how their appearance is germane to the story.

Made you look!

Happy Birthday, Nia!

As the women were completing their metamorphosis into runway models, I surreptitiously stepped to the refrigerator, grabbed the oversize cupcake, and stuck a candle in the top. After lighting it, I turned around to the ladies and started the opening lines of the song I knew by heart, even if I had never been allowed to sing it for most of my life. The other girls promptly joined in and we watched as a surprised Nia blew out the flame. That being accomplished, it was now time to go party.

On our way to the large, private parking lot, we stopped in the lobby to take pictures. One of the maintenance guys, Lester, who was on the night shift, happened to wander past. He stopped in his tracks and stared with an open mouth at me, surrounded by my new friends in their finery. I took advantage of the situation by placing my cellphone in his hand and asking him to snap a few shots for us. As I took the phone from him, he told me to have a good night as his eyes were saying, “How the FUCK???” I winked at him and led the women to my car.

Dressed to kill

Two years before, I had purchased a gently-used 1999 Toyota Avalon after my beloved Cadillac STS blew a head gasket and was old enough to not be worth pouring any more repair money into. The Avalon was a beautiful machine. Pearl white, complete with heated leather seats, moonroof, and just about every option that was imaginable at the time of its manufacture, it was a true luxury car. It was fifteen years old, but was in exceptional condition, and it was paid for in cash.

One of the best features of the Avalon, however, was that it was one of the last six-passenger sedans produced for sale in the US. The front seats had a 60/40 split and sat three adults across comfortably, provided that one of the adults wasn’t too large. This advantage meant that we didn’t have to call for an Uber SUV to get us from my Bronzeville neighborhood apartment to our destination at 632. N. Dearborn Avenue. It was now 12:30am.

After a 15-minute drive through light traffic at that late hour, I put the gear selector into the “park” position in front of the monstrous building with the gothic design and a reputation for being haunted. This was The Castle, and the thumping music was audible from the street. I stepped out of the car and opened the rear driver’s side door for my back seat passengers to emerge. The valet handed me a slip of paper before disappearing with my car to a parking lot somewhere nearby.

I’m not exaggerating a bit here when I say that I witnessed guys stopping in their tracks to gawk at my guests. I think I saw at least one of them let go of the hand of the woman he was with and almost imperceptively move an inch or two away from her side as he continued to stare in our direction. The ladies didn’t seem to notice and we quickly crossed the sidewalk and into the entrance where we were greeted by two large bouncers dressed almost exactly like me. The cover was $20 to enter, which seemed exorbitant to me, but this was the neighborhood where all the cool kids went, and my paycheck was easily able to handle it.

Dancing queens

Once inside, we first grabbed drinks at the cocktail bar, then followed the booming noise into one of the larger rooms housing a massive dance floor and stage where two DJ’s were pushing out popular club tunes. Flashing lights on the ceiling and a few smoke machines at the edges of the walls created just the right ambiance for revelry.

Arriving inside The Castle

Even though I had taken formal dance lessons a few years before, and was frequently attending the weekend Summerdance events in Grant Park, my normal choice of real estate on any dance floor was near a wall. But my companions had other plans. I dutifully followed them as they deftly made their way right up to the front, just below where the DJ’s were standing. This was Nia’s birthday, and they planned to live it up. I stood still for only a minute before deciding that looked more stupid than any type of movement I could produce. They danced, and so did I.

I should say that while I danced okay, even getting a couple of nice compliments on my abilities to keep rhythm (there’s a big reason why that meant so much to me), the ladies danced spectacularly. Linda, Nadia, and Amber had actually all been belly dance instructors at one point, and the other two, Nia, and Desiree, kept right up with them in their unbelievably fluid movements.

Dance was initially what brought Amber and the two sisters together in the first place six years before. For the next three years, they spent time together at university and on the dance floor. In late 2011, these fast friends met Desiree and Nia separately, and of course invited them to go dancing as well. Going to classes and to clubs became the part of the glue that cemented the bond these five shared. Dancing ran in their veins, and they were masters of the craft. Amber also practiced pole dancing. Suffice to say, these girls did not go unnoticed inside the club.

The bodyguard

I however, seemed to blend in perfectly. In my obsidian ensemble, I practically disappeared. Which was fine with me. All eyes were on the quintet dancing directly in front of the stage. At some point, the owners of those eyes began to feel that more than ogling was acceptable. On at least two occasions during the first 30 minutes we were there, I saw hands reaching for bodies that did not belong to them.

I don’t know what gets into a person’s head to think that it is okay to put their hands on someone else without invitation. Some blame alcohol or other intoxicants for that boorish behavior. Other neanderthals will try to blame the victim for dressing provocatively. In either case, it is not a defensible action.

“…and keep your hands to yourself”

As I saw those uninvited appendages moving in the direction of my dancing companions, I took it upon myself to grab the offender’s wrist quite firmly and push it back to him as I stared him down while using my free hand to wag an index finger in a “no, no” gesture. NOW he saw me. And I saw fear. “Uh, uh, oh! Sorry! I didn’t see you!,” was the response from one of the two as he backed away.

While I was quite happy to let the ladies turn down invitations to dance with men who asked them politely, only one guy actually did ask. And he was rewarded with a couple of minutes of being able to move on the floor with one of the women, though it was sans touching. A few other men, however, felt it was their right to grind up on the girls, which elicited a rather different outcome.

A little later, another young man feeling his oats approached Linda and tried to start dancing with her. She turned him away. I watched him go back to stand with his friend, and a few minutes later he returned for another try. Linda again told him “No!”, this time more emphatically. Again, he walked to his friend who started to whisper in his ear.

On his third attempt, I got involved. As he approached Linda from behind, I stepped directly in front of him. He stopped. I smiled. I explained in a calm voice that these girls were here to have a good time with each other and were not interested in meeting new guys tonight.

I continued in a measured tone, “They want to dance by themselves. They all have boyfriends already. They don’t want to dance with you. Don’t feel bad about it, they don’t even want to dance with me. Now from what I’ve seen, you are getting some bad advice from your wingman standing over there. I suggest you go back to him, take him into the bathroom stall, and let him give you a handjob, because I don’t want to see you back here again.”

Or something to that effect.

He looked at me with alcohol-fueled anger, and I thought for a second he was going to try to take a swing. However, he realized that I stood a head taller than he did and my imposing figure was more than he wanted to deal with. Maybe he called me a name as he turned, maybe he just said some angry words. I don’t remember. Nor did I care. It was a very satisfying moment for me.

King of clubs

About a minute later, the music stopped for the second time since we arrived. The first time was because the DJ’s wanted to run a contest. They pointed at three different women in the audience and invited them up onto the stage. Then they asked for a male volunteer, with the caveat that the guy had to be a virgin. A lot of the hands went down, but not all of them. One young man who kept his hand raised was asked, “Are you REALLY a virgin?” He was too embarrassed to answer in the affirmative, so he put his hand back to his side.

My new friends were screaming at the DJ while pointing at me, while trying to push my hand into the air. I had fathered two children already and told them as such while I determinedly kept my arms below my head.

However, there was one potential contestant who insisted that he had yet to experience the wonders of sexual relations with another person, so he was brought up onto the stage and placed in front of the ladies already up there.

“This game is called ‘The Pole’,” one of the DJ’s announced. Turning to speak directly to the young virgin lad, he continued, “You are the pole. You will stand straight, arms at your side, while the ladies use you as a pole to dance on. You may not touch them. Understood?”

The kid nodded his comprehension of the rules. The crowd would choose the best “pole” dancer by the amount of applause they gave. I nudged Amber, telling her that she should be up there. She told me to shut up.

The poor boy could not keep his hands off the women as they took turns dancing lasciviously around and on his form. The DJ’s had to remind him several times that he must remain motionless. Eventually, one of the ladies was declared the winner, and everyone was shoved off the stage while the music started back up.

The second time the music was interrupted, the DJ’s again picked out two women from the crowd for a yet-to-be-revealed contest. They then commenced to ask for two men to join the ladies on the stage. This time, my companions would not take ‘no’ for an answer. They had already been noticed by the DJ’s (and by everyone else), so I was chosen to be part of the show.

I stood up on the stage, looking out at the crowd of faces. I shot a nasty look at my couchsurfing guests for putting me in this awkward and most-likely embarrassing position. They didn’t care. It was funny to them.

So embarrassing

“The name of this contest is ‘Two-Pump Chump!” the DJ shouted into the microphone. “Each couple will have two tries to pop this balloon while simulating doggy-style sex.”

Oh. My. God.

This wasn’t happening to me. I put my head in my hand. This was going to be mortifying, and because of the wonders of streaming video uploads, it was going to live forever.

This is when my assigned partner, the bride-to-be in the tight white dress, demanded that I force the latex orb to burst. “You better make it pop!”

We watched as the other couple went first. The guy was given an oversized pair of tighty-whities to put on over his clothing, then the balloon was inserted into the front. The girl bent over and grabbed her ankles as he approached her from behind. He took hold of her waist with both hands and gave a mighty thrust with his hips. Twice.

The balloon, however, refused to rupture. It simply didn’t have enough air inside to cause the stress needed on the rubber to bring it to the breaking point. The inflatable toy simply squeezed itself into an oblong shape, pushing out one side of the underwear.

After his failure, the tall man took off the underwear and handed the balloon to the DJ. These two objects were now given to me. I sighed to myself and accepted my fate. But, since I was going to be a YouTube sensation somewhere, I decided to ham it up a bit.

I refused the oversized briefs at first, waving them and holding my nose, as they had just come off another man’s body. When I did don the man diaper with the help of my partner, I grinned out at the crowd and placed the balloon in front, making a show of it. My lady-in-waiting stepped in front of me, turned around, and bent forward.

As I predicted, the balloon remained intact even though I gave those two thrusts my best shot. As I began to remove the humiliating Hanes, the DJ stopped me. He told the lady to “finish him. Give him a hand-job!”

To me, this was even more cringe-worthy than the previous act. The bachelorette knelt in front of me, grabbed the balloon, and simulated jerking me off while she worked her fingernails into the thin rubber material. It popped. Not knowing what else to do, I pretended that it was the best orgasm I ever had. The crowd loved it.

Later, I was invited by the DJ’s to join the second session of “ladies only” dancing up on the stage. I assumed that this was because they had been watching my interactions with my friends during the previous two hours and were acknowledging that I was an okay dude. A couple other guys saw me and tried to climb up themselves, but were rudely shoved away by the club staff.

It was such a gratifying experience for me.

After the dance

A short time later, the ladies had had enough of the clubbing. We went back out into the night air. I tipped the valet as he brought my car up, and we piled into the car. Instead of going home, I took the girls on a lovely ride down Lake Shore Drive, with the moonroof and windows open. We went to an all-night diner in the Hyde Park neighborhood and ordered breakfasts at 3:30am.

Linda and Nia both fell asleep in the booth, leaving their pancakes untouched. Some guy came over and tried to talk to the girls, but everyone was too exhausted to pay him any attention, and he wandered away after a couple of minutes.

The sun was rising as I drove them back up the waterfront expressway to the 31st Street exit. Upon entering my apartment housed in the building that stands in the 2800 block of S. Martin Luther King Drive, everyone fell into their beds as soon as I could make them up.

Slumber party in my studio apartment

Somewhere in the next few hours, Charlie peed on Nia’s sleeping bag. Not sure why he singled her out. Maybe he knew it was her birthday and wanted to give her something to remember him by. I felt pretty bad about it. Charlie didn’t. I took the smelly bedding down to the laundry and washed it with some type of nicely-scented detergent. When I came back upstairs, Desiree had taken over my kitchen and prepared a stack of authentic French crepes for us to enjoy.

Mid-afternoon arrived, and my guests finished packing their belongings back into their bags. We exchanged WhatsApp accounts (as I had yet to join Facebook), then they bid me farewell and drove back to their homes in western Michigan.

Through social media, I have kept in contact with all five members of The Pentagon, as they like to call themselves. During the past nine years, at least two have gotten married, the others are in happy relationships, and two are now mothers. I was lucky enough to see Amber once more before I left the States. And I briefly visited Desiree in Vientiane, Laos after escaping China at the start of the COVID pandemic. I hold out hope that I’ll meet up with the others in the future.

After nine years, I am now in possession of the video of my turn as “Two-Pump Chump.” I hope to never find it on YouTube.