Urban jungle

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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sunset
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Urban jungle

Post by sunset »

“Almost 11:00 PM,” I thought to myself as the moon shined through the scattered clouds. I was out later than I intended, especially considering I had an 8:00 AM class the following morning- just another dreadful thought that lingered in the back of my mind. However, going to bed a little later than I expected was certainly the least of my worries during that unforgettable night.

I had just parted ways with a friend of mine from high school who also happened to go to college in downtown Chicago. It was a pleasant night: we reminisced a bit and eventually saw a movie at an old theater in the South Loop neighborhood. Having just moved to the big city, I was rather unfamiliar with this part of town. I knew it was rather far from my apartment on the North Side so I decided it would be best to take the subway back to my neighborhood. 

As I descended down the steps to the main platform, I was overcome by how empty the station was at this time of night. Bear in mind, I’m someone with an average build and timid nature, so this was naturally a very intimidating site. I sat down on a bench and gazed upon the battered structures of my surroundings. Graffiti completely covered the walls and trash swayed from the cool winds coming from the spring night. I kept rubbing my arm, somehow thinking this small act would make the train miraculously arrive faster. Just when my racing mind couldn’t get any more paranoid, I heard distant laughter emerging from the far end of the tunnel.

The laughter and voices grew louder. Before I could properly react, five thugs emerged from the shadows and gazed in my direction. I instantly froze with fear as one of the members shouted to his friends, “Hey, look who we have here!” As the strangers trotted in my direction, I noticed the three men and two women were absolutely covered in various tattoos and piercings. Once they got closer to me, they started circling my presence like a pack of sharks closing in on their helpless prey. 

“What’s your name? You, my friend, look like you have some money. Why don’t you hand it over and we won’t hurt you,” one of the skinnier men said in a raspy voice.

“Matt. And n-no. I don’t have any. Please leave me alone,” I sheepishly replied.

“Then what’s this thing bulging out of your pants pocket?” One of the girls exclaimed as she gently, but menacingly, stroked the side of my leg.

As I squirmed and tried to talk my way out of giving my money to these thugs, one of the bigger men shouted in a deep voice, “When we tell you to give us you money, you do it...NOW!”

Before I could react, the other young women reached into my pant pocket and snatched my wallet containing my cash and train ticket. “Wait! Take the money, but at least let me keep the ticket. I’m just trying to get home,” I pleaded. To my disappointment, they just laughed as my request.

As the leader searched through my wallet, one of the two girls with beautiful green eyes approached him and began whispering something in his ear. As she exchanged her thoughts, the man smiled and laughed to himself.

“Hey, guys, Tanya just told me a great idea. Our new friend here looks very clean, doesn't he? So clean, in fact, he probably goes to a fancy school and thinks people like us are nothing more than dogs. So how about we teach him a lesson,” proclaimed the leader.

“You have my wallet and my ticket! What more do you want? Just let me go!” I shouted.

“Not yet, friend. Tanya here wants to see you without your fancy clothes on.”

“What?!” I shouted abruptly as my heart began racing.

“You heard me. Strip. NOW!” The leader shouted menacingly as he cracked his knuckles.


As I attempted to plea for some salvation, Tanya interrupted me, “Quit stalling, kid. You can either undress yourself or we can do it for you. Either way, you’re gonna be naked.” 


Suddenly, two of the boys grabbed my arms and prevented me from fleeing. The two punk girls chuckled as they unbuttoned my shirt and paraded it over their heads. The embarrassment already began sinking in as I knew these muscular crooks were looking at my skinny physique with judgmental eyes. Then, Tanya bent down to unbuckle my belt while the other girl pulled my pants down around my ankles. She then collected my shirt, pants, shoes and socks while I stood there shivering in my underwear. It was a strange sensation to feel the cold asphalt on my bare feet. As I stood motionless in my black underwear in front of these complete strangers I hoped it was all over. Unfortunately, this was not the case. As the others laughed, Tanya slowly approached and slipped her fingers behind the waistband of my underwear. My gut churned. In a split second, she swiftly pulled my underwear down to my ankles and forcefully lifted my last article of clothing out from under my feet and into her possession. In that moment, I was completely naked.

Laughter erupted among the group of thugs as they mercilessly mocked my penis which had shriveled due to the brisk air.

“Hey, do all you students have small dicks or is it just you?” One of the boys shouted. “Turn him around, let’s see his ass,” one of the girls joked. Meanwhile, I noticed Tayna putting my clothes in her backpack. “Wait, give those back! You can’t leave me like this!” I screamed loudly. As the group of thugs packed up and ran away, Tanya replied with a hint of snark, "Go back home to your mommy, little willy!"

Absolutely flabbergasted, I stood in the middle of the platform covering my genitals and shivering from the cool air consuming my bared skin. I was so angry, scared and humiliated. Why would this happen to me? 

Once I explained my situation to the conductor (which he found hilarious) I shuffled to an empty car and sat my bare bottom on the cool porcelian chairs of the CTA. It was a strange feeling sitting there totally naked. While I'm not proud to admit this, it was somewhat arousing at times; but the fear of the events that led to my naked adventure definitely overwhelmed any feelings of pleasure. At every station, when the subway stopped and the doors opened, I trembled at the thought of someone seeing me in my state of vulnerability. How would I even explain this to someone?

"I'm almost there. Just three more stops," I thought to myself. However my optimism was short lived. As the trained pulled into the next stop, a young couple walked into my car and immediately locked their eyes on my body. I could feel the blood rush to my cheeks and my knee violently shaking from the sheer embarrassment. As the couple found their seats, I glanced over and noticed them giggling and motioning towards me. Maybe they thought it was a joke or that I had gone crazy. The girl kept sneaking glances at me, causing a strange sensation of humiliation and pleasure. Ultimately, though, I still think she thought my predicament was humorous. I tried explaining to them what had happen to me, but I kept tripping over my words. Luckily, the two strangers eventually recognized I was the victim of a crime and a certain level of guilt was expressed on their faces. 

The couple got off at the stop before mine and I let out a sigh of relief. As the train pulled into the station closest to my apartment, I swiftly exited the car and headed to the sidewalk with my genitals cupped in my hands. While walking down the street, I passed several people, many of whom took out their cell phones to document my naked adventure (I later heard a picture of my butt made the front page on a social media website the next day). As I turned the corner, the street cleared of people and I assumed I was free of any more wandering eyes. Or so I thought.

"Hey, what do you think you're doing? Are you drunk or something?" a commanding voice from the shadows erupted. As my eyes focused in the darkness, I realized the voice came from a police officer leaning out his car window. My knees buckled at the thought that I could be getting into legal trouble for my indecent exposure. I quickly explained the reason for my public nudity. Luckily, the officer took pity on me and subsequently offered me a ride to my apartment. I eagerly agreed, until I realized the policeman was not alone.

As I entered the squad car, his partner, a beautiful blond policewomen in her thirties gazed upon my naked body as I entered the back seat. I could tell she was holding back her laughter as she asked me questions about the thugs who assaulted me. She urged me to file a police report in the morning and jokingly suggested I wear clothes for the occasion. I sheepishly laughed at her quip. Unfortunately for me, she would ultimately have the last laugh. The beautiful face of the policewoman coupled with my naked body pressed against the leather seat stimulated an erection I desperately tried to hide. I could tell she noticed my arousal when she let out a small gasp which caused my embarrassment to skyrocket. After a five minute ride, we pulled in front of my apartment building. The officers wished me a good night and I quickly walked up the stairs to my front door. I could feel the policewoman's gaze upon my butt while I ascended the stairs. I just need to go to bed.

I let out a timid chuckle as I subconsciously attempted to locate my keys, which I quickly remembered were stolen along with the rest of my clothes. In defeat, I rang the doorbell and awaited the inevitable confrontation with my roommate, Carl. As the sound of footsteps grew louder, my body tensed up awaiting even further ridicule for my predicament. I closed my eyes as the door swung open.

Matt?! What the hell are you doing? Are you drunk or something?" Carl shouted the instant he noticed me standing in the front porch cupping my genitals. 

I pushed myself inside to our unit while muttering, "No I'm not drunk, I'll tell you about it ins- oh, fuck!!"

Gasps filled the air as I staggered straight into the height of my embarrassing journey. Just when I thought the nightmare was over, I noticed two girls sitting at the kitchen table drinking wine. One of the women was Carl's girlfriend, Heather, while the other was Julia. My heart sank once my mind processed Julia's presence in my home as I stood in front of her stark naked. She was a plump, red-headed bombshell who I had a crush on since the beginning of college. She sat in complete silence and blushed as her eyes scanned my body.

"Why are you naked, Matt?! Did you lose at strip poker?" Heather blurted out.

"No, I-I was robbed," I muttered.

I quickly fled the scene and headed straight to my bedroom. During my retreat I could hear Heather shouting, "Nice ass!" Once inside the safety and seclusion of my bedroom, I buried my shame-ridden face into my pillow. I kept thinking to myself, "There goes any chance of successfully flirting with Julia ever again. She must think I'm a joke."


I quickly got dressed and built up all my courage to join my friends in the main room again. Upon my return, Carl and Heather giggled while Julia continued to blush. As Carl handed me a beer, he ask me to retell the story yet again. I let out a long sigh and started from the beginning.

"I'll be honest. It's always been a fantasy of mine to have my clothes stolen while I was in public. It must have been exhilirating to wander around in the nude," Heather admitted upon hearing my story. It did make me feel a little better. And while I did openly say it was a horrible experience, it was rather erotic at certain points. It was a confusing mix of emotions, to be sure.


At around 3:00 AM Heather and Julia were ready to go home. As I walked Julia to the door she turned to me and whispered, "Matt, don't worry about what happened tonight. All that matters is you didn't get hurt. And, also, I happen to be free tomorrow, so if you want someone to come with you to file the police report, I'd love to join you." Taken back by the offer, I stuttered, "Oh, T-thank you. That sounds great!" She then leaned in and gently gave me a kiss on the cheek. My cheek burned even redder than any other point during that night. Before she turned around and left she said in a flirting tone, "By the way, Heather was right. You do have a cute butt."


I suppose, in the end, it was a good night after all.
Xirix7
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Joined: Thu Dec 09, 2021 6:01 pm
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Re: Urban jungle

Post by Xirix7 »

Very turned on by the punk girls getting to see him forced to be in the nude with his small penis on display and totally humiliated. The guy called him out for his having a small sized penis, but I wonder what the women thought of his naked body and penis size?
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