The Tennis Bet

By uppishcarrot.


When I was younger, I was full of confidence. I carried myself with unfounded machismo and bravado.

I joined a tennis club to get extra credit when I began my studies. It was a great way to stay in shape and had many social benefits.

The club was massive, especially in terms of members. It also seemed that there were double the number of women compared to men. In other words, there was a lot of eye candy. I spent much alone time rubbing myself raw, running through my highlight reel.

No one drove me crazy as much as Erica Vernon. This was a confident, statuesque goddess with a toned and athletic figure. She could’ve gone pro, too, if her parents would’ve been a tad more supportive. She also seemed to have an entourage, surrounded by the same group of scantily dressed bombshells.

I wasn’t that bad to look at, either. In fact, during my practice, I’d always have an eager audience, most of whom were women. I even dated a few of my ‘fans,’ but it stayed within a second or third date.

The real object of my affection was Erica. With my arrogance and bravado, I waltzed over to her and, in front of her entourage, asked her out on a date.

She politely declined.

What followed was weeks of me trying to impress her, which only made me look desperate and foolish.

I knew I could win her over if she just got to know me.

So, on one fateful day, I approached her and challenged her to a game. 2 sets. I was suave, I was charismatic, I was arrogant. “If you win, I promise to leave you alone… but if I win… you must go out with me”. I was sure this was going to work, I knew my game was impressive and was confident I could defeat her with very little effort. Unfortunately, I completely underestimated her. Eyeing me up and down with an amused smirked, she pondered and snickered before saying, “Okay. Deal…” she paused as a sadistic grin washed over her, “But, if I win the first set, you have to play the second set, completely naked” she said.

This took the wind out of my sails, and my delicate ego quickly eroded before her. Sensing my unease, she began to laugh. Her entourage, all looking on, also began to laugh in unison, all at my expense.

My plan had backfired, and I had to go through it to save face. The ruckus her entourage was causing somehow managed to capture the attention of almost everyone. I had talked myself into a corner and was unbelievably horrified and embarrassed.

Ten minutes later, we took our place on the court. Word had spread, and at least 100 friends and students attended, eager to witness the game of the decade.

As I said, I completely underestimated her. My ego had clouded my judgment. I couldn’t think straight, I couldn’t concentrate. As I played, I felt like the butt of some kind of joke. Almost everyone looking on was amused so that I couldn’t get out of my head. My game suffered. In the end, she completely eviscerated me.

In the first set, I lost 2-6. It took her 38 minutes to defeat me.

So, as per the details of the bet, I had to play the next set…. naked as the day I was born. My confidence and bravado eroded as I desperately tried to talk myself out of my predicament. “Oh, surely that was just a joke? Right? You uhh… can’t expect me to uhhh… Play naked!” I pleaded with her, horrified, mortified, embarrassed, and humiliated. Erica just laughed and mocked me, calling me out in front of everyone for my misogyny and going out of her way to destroy what was left of my manhood, “I thought you were a ‘big man,’ aren’t you?” she teased, “got something embarrassing to hide?” she teased some more before adding, “a bet is a bet! I wasn’t going to chicken out…. You pussy” she said with a sadistic grin.

The crowd quickly turned on me as I was called a coward. After a few minutes of pleading for mercy, someone from the audience called out “pussy boy”… this caught on, and before too long, everyone was chanting “pussy boy, pussy boy” over and over.

I had no choice. There was no getting out of this.

So, reluctantly, I got undressed.

I got howls and whistles as I removed my shirt, then my shoes, then my socks, then my shorts. Before too long, I stood before everyone in nothing but a pair of blue shorts. I scanned the faces of the crowd, hoping for some sympathy. Unfortunately, I got none. “Take it off! Take it off! Take it off!” the crowd began to chant. Pleadingly, I glanced back at Erica, who ran her tongue over her upper lip. She was enjoying my torment perhaps a little too much.

There was no way of getting out of this, so, conceding defeat, I decided to remove my shorts, exposing myself to everyone in the process. Nerves contributed to an insignificant little penis. Standing naked before everyone was surreal, and never in my entire life had I ever felt so exposed, vulnerable, and insecure. At first, there was dead silence as everyone studied and examined my body. A few seconds later, the entire court erupted in laughter as I stood there, mortified and embarrassed.

Looking down, I confirmed my greatest fear: my penis had retreated completely inside of me. It was gone, lost in the thick nest of pubic hair. I’m sure it looked like I had no male genitalia at all. I glanced back up at Erica, who simply howled with laughter. Internally, I was dying ‘God!!! NOOO!! Please come out! Just a little bit!! Please!!!’ I pleaded with my body. It was no use; I had completely walked into this, and now, I was exposed as the owner of a micro pee-pee.

Eventually, the laughter died down, and Erica served. I had to continue. All I could think about was how exposed I was. My insecurities are on display in plain sight. Muffled laughter, giggles, and chatter continued as I played. It wasn’t very comfortable. All the while, my little dick remained hidden, but I could feel it bobbing as I returned her serve, but from her vantage point, I’m sure she couldn’t see anything… Neither could anyone else.

I very quickly lost the second set: 0-6. This time, it was over in only 8 minutes.

A ruckus round of applause took over as Erica effortlessly defeated me on the court and socially. It was clear that she had destroyed my image. I had been publicly emasculated, and she marveled at her victory.

I kept my head down as we met in the center of the court. Erica reached out and shook my hand, “good game,” she glanced down at my little lifeless dick, the mushroom tip barely poking out of the nest of black pubic hair, “Pee-wee,” she added, before erupting in laughter, right in my face. “You wanted to date me?! With that?! Oh my god,” she added, continuing to laugh and laugh at my expense.

Yes, I was a fool to think I even had a chance with her. She was right. With what little I possessed, it was clear that I was not a man. Now, it was clear to everyone. I was nothing more than a testosterone-fuelled lug-head, parading around with false machismo, very clearly overcompensating. I was exposed.

I was quick to get dressed and retreated to the club as everyone hurled small penis insults my way. In shame, I left and never returned. That whole experience changed how I viewed myself as a man, and I was never the same again.

 

The End.

 

*This story has been edited by AI to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story has been previously published on other free sites and is now public domain, which is why we can publish it here.

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