The Prettiest Penis Contest
By Characterorder.

I looked up from my laptop at my dorm room door. I hadn’t been expecting someone to come over on this quiet Saturday morning. Shutting my laptop, I hopped out of bed and opened the door.
To my pleasant surprise, it was my friend, Mia. Short in stature but high in energy, Mia was in the same year as me at university. We were in the same program, so we had taken most of our classes together. Candidly, I harbored a bit of a crush on her – she had the biggest brown eyes that were so easy to get lost in, and a warm if not mischievous smile. She kept her cards close to her chest, which… uh… sorry, I lost my train of thought thinking about her chest. She tended to wear tight but not necessarily revealing clothing; today, she was wearing a black quarter-zip sweater that was zipped most of the way up, paired with leggings. I often caught myself in class staring at her, fantasizing about just a peek at what she was concealing underneath.
“Hey, Liam!” she said with a smile, “I was hoping you’d be here. Are you alone? Can I come in?”
Before I could answer, she pushed past me into the room. I looked out into the hall to see if there was anyone with her, or for any other clue as to why she was here. We were friends, but not best friends; it wasn’t in our relationship for her to show up at my dorm like this.
“Yeah, I’m alone,” I answered. “Everything okay?”
“Everything’s great,” she said. “You should shut the door.”
I’d watched enough amateur pornos in my time to get my hopes up immediately, but there was no way that’s what she was here for. Mia was single, to my knowledge, but the guys I’d seen her out with were what you’d expect: muscular, conventionally handsome, great hair, life-of-the-party types. I was tall but thin, and had never really dated due to some… insecurities.
I did as she asked, and I shut the door. “Okay, you’ve piqued my curiosity,” I said, “What’s going on?”
“We have to be quick, Liam,” she said, “Something is happening today, something really special, that’s going to be huge for me.”
“You’re speaking very cryptically,” I teased her. It didn’t seem like there was some sort of emergency, but she was clearly in a hurry for some reason.
“You’re right, I’m sorry, I’m just nervous,” she said. “Well, excited, and nervous. Well… you know what this is going to be easier if I do this first.” She raised her fist with her fingers pinched directly in front of my widening eyes. “Liam, just know that everything that happens from here on out, I’m just doing what I think is right.” She snapped her fingers and suddenly, I felt the room go all funny. It felt as if my brain had turned to mush, and everything was moving in slow motion while remaining still at the same time.
“What was that?” I asked, hearing my own words in my ears like I was underwater.
“I’m hypnotizing you, Liam,” Mia said calmly. “My whole life, I’ve had, well, let’s call it a gift, to get men to do whatever I say. Some people assume it’s just charm and sex appeal, but it’s a real power I have. And today, I need your help with something that requires complete obedience, and that will be much easier if I have you hypnotized. I can’t have you screwing this up for me.”
I felt almost euphoric, light-headed, and warm. I stumbled backward and caught myself on my mattress, landing sitting upright. “Okay,” I said with a dopey grin. I felt silly, but I could still comprehend what she was saying to me. “Anything you need! What are we going to do?” Whatever she had done to me, it was working, and I felt eager to participate.
“There’s a contest happening in the city,” she said, pulling a pamphlet out of her pocket. “Invitation only, and the prize is huge – $15,000 for the winner. You and I are going to go downtown and get ready backstage. I’ll explain everything there.”
“Sounds great, should I change into something nicer?” I asked.
She smirked. “Don’t worry about what you’re wearing, you’re perfect.” She took my hand, and I nearly gasped – I was probably under her spell without hypnosis, but now? If she told me to do a cartwheel into oncoming traffic, I probably would have! She led me out of my dorm and to the contest…
***
We arrived at the venue, a large performing arts center in downtown. I had never been, but it was a frequent stop for musicians, comedians, and other touring acts. Mia, still leading me by the hand, brought me to the backstage entrance, showed a pass to the security guard, and we were escorted to a private room backstage. “You guys are late,” a pink-haired stage manager said to her. “You’ve got less than an hour to get ready, so you’d better hurry.”
“Yeah, yeah, yeah,” Mia said, shutting the door on her. She stood me up in the middle of the dressing room. A mirror occupied most of one wall, accompanied by a makeup counter and a chair in the center. “Alright, Liam,” Mia smiled at me, “You’ve been such a good boy so far” – this word choice made me stand up a little straighter, like I needed to impress her – “but now is when the real test begins.”
“Of course, Mia!” I said, with nearly golden retriever-level energy, “Anything for you!”
“That’s what we’re going to test,” Mia said. “Because today’s contest is no ordinary contest. It’s, well, sort of a… male beauty pageant.”
I let out a laugh. “You may have picked the wrong guy to enter, but I’ll try my best!” I said, practically wagging my tail.
“Only sort of,” Mia said with some authority, enough that I felt my metaphorical tail stop wagging. “This is a very specific type of beauty pageant. I’ve entered us to compete in a Prettiest Penis Contest.”
Even in my woozy state, I thought surely I had heard her wrong. “Come again,” I said, blinking. There’s no way that she…
“Don’t be stupid,” she said, “it’s a Prettiest Penis Contest. You and I, along with a dozen other pairs, are going to compete to see which boy” – and I feel like she chose that word on purpose – “has the prettiest penis. The woman who entered the winning boy gets the cash.”
I was so baffled. Mia and I weren’t a couple; we’d never been intimate, and she’d never seen my penis. Nobody had! My underdeveloped member was the source of significant anxiety and shame. I’d never even changed in a locker room before.
Strangely, and surely from the effects of the hypnosis, I didn’t find myself panicking at what she was describing, merely confused. “But why me?” I asked.
“I’ve seen a lot of penises, Liam. Like, a lot,” Mia said, in a way that strangely stung a little to hear her say. “They are, almost without exception, disgusting. Soft, hard, whatever, they’re a gross, fleshy appendage that hangs stupidly between a man’s legs. Even a well-groomed man can be transformed into a beast when it comes to matters involving his penis, let alone his precious, fragile balls. Hardly the sort of thing that could be entered into a Prettiest Penis Contest.”
I nodded; it was hard to disagree with her logic, and in my hypnotized state, I actually felt enthusiastic agreement with her. Penises are disgusting. My penis, despite being small, is disgusting.
“That’s where you come in,” she said. “I know you don’t date. I know you don’t sleep around. In fact, you’re probably one of the only guys on our campus who hasn’t made a move on me, and you’re not funny enough to be a gay guy, no offense.”
“None taken,” I said, smiling like an idiot.
“So it clicked for me,” she said, stepping toward me. She put her hands on the bottom of my shirt and pulled it over my head and off of me with ease. “You must have a tiny little penis!”
My heart was pounding. Hearing her say those words felt like ice water on top of my head. She must have seen the flash of horror on my face and realized she might be pushing too far to maintain her control, so she snapped her fingers in my face again. I felt the fear washing away, and I perked right up.
“Yup, it’s true!” I said, downright gleeful. “It’s got a tiny little penis! Plus, little balls to boot!”
She grinned and looked down at my middle. “Why don’t you be a good boy and show me, please,” she instructed.
With no hesitation, I peeled off my socks, threw my jeans down to my ankles, and kicked them off. My lucid self would never realize what I was about to do – I was about to expose my most intimate part, my deepest secret, my ultimate source of anxiety and shame, to who was unquestionably the most perfectly formed woman I had ever laid eyes on.
And yet, in my current state, I felt entirely compelled. With that, I whisked my boxers down to the floor, and my little penis popped into view. Well, popped might have implied some degree of making an appearance.
A big grin spread across Mia’s face as she took it all in, or at least what was there to take in. My little nub of a penis, nestled upon my tight scrotum, barely pokes out through my bush of pubic hair. I had never considered anyone seeing me like this, so I had never given thought to grooming.
“Oh, Liam,” she said, a dirty giggle escaping her beautiful lips, “You are perfect for this.” She knelt so she was at eye level with my penis. “It’s cute! But cute won’t win the Prettiest Penis Contest! Go sit in the chair and we’ll get started.”
With no hesitation, I turned and marched to the chair. “Cute ass, actually!” Mia called out behind me. “Plumper than I would have expected, it’s nice!”
I sat in the chair, legs spread ever so slightly, so my penis was in plain view. It was soft and squishy, and looked like it was sleeping on two little pillows that were my balls, though even those were so small it was hard to tell that there were two. I rested in the chair, eagerly awaiting further instructions.
“First things first,” she said, walking toward me, an electric razor in her hand. “We’ve got to get rid of those pubes. You can barely see the poor little guy!” She knelt on the floor before me, on her knees, in a position that under normal circumstances might have triggered a visceral reaction in me. But under her control, I felt unfazed by her proximity to my minuscule manhood.
“I’m gonna need you to spread your legs so I can really get in there,” she instructed, patting my inner thigh. “Go on then, be a good boy.” Enthusiastically, I spread my legs for her. I didn’t expose my ass to her from how I was sitting, but the image of my wide-open legs and little penis resting in front of her caused her to stifle a laugh.
“Good boy, Liam, very good,” Mia smiled. “Now hold still, this will tickle.” Suddenly, she reached her hand out and wrapped her fingers around my penis. It felt like a lightning bolt had cracked through my entire body. I had never felt a woman’s grasp on the most intimate, sensitive part of my body. Every neuron in my brain fired at once. She wasn’t trying to pleasure me; she just needed to help the little mushroom while she got to work.
I heard the buzz of the razor, and she began shaving me. She was right, it tickled a little. Almost without intention, I felt her fingers gently feeling my penis. It was probably unlike the cocks she was used to handling; it was totally soft, even with her manipulating it. She played with it a little, the way someone might use a fidget toy when they were bored.
After a few minutes of shaving, she blew air onto her work area, which caused me to let out an exclamation at the sensation. “Oh!” and I nearly jumped out of the chair.
My movement caused her hand on my penis to tighten. “Down, boy,” she said, like a joke, and I settled back into the chair. She brought the razor back to finish up a few spots, but in a matter of moments, I had become totally hairless down there.
She grinned as she admired her handiwork, and I looked down as well. I had never seen myself shaved, and it definitely helped with being able to see my little penis, even if it was still utterly unimpressive. I noticed the way Mia kept my penis and balls resting in her palm, and I was struck by the erotic contrast of my small, disgusting, wholly unsexual sex organ resting on her elegant, feminine, impossibly beautiful hand.
“We need a little something else,” Mia said, reaching into her bag. She pulled out a little pink bow. “This ought to do it.” With one hand, she scooped up my penis and balls again, and with her free hand, she wrapped the bow around me. She tied it, not too tight, but enough that my penis and scrotum were now bolstered up by this dainty pink bow, resting on top of it all. It was like the saddest present one could imagine receiving. She reached up and tied a matching pink bow around my neck. “There he is!” she said proudly. “My little man looks so good!”
There was a knock at the door, followed by the stage manager peaking her head in. I was unfazed by the intrusion, even in my ridiculous state.
“Mia, Liam,” the stage manager said, looking up from her clipboard, and my penis caught her attention. She let out a snort. “Oh!” she covered her mouth with her clipboard. “Sorry, I’ve seen a lot of penises today, but…” she was absolutely beaming with amusement. She looked at Mia and said, “Really good job.”
“Thank you,” Mia grinned. “Liam was a very good boy.” I smiled proudly.
“You two are up now,” the stage manager said. “Places, please.” She stepped out of the doorway, leaving the door ajar.
“Alright, Liam,” Mia said, turning back toward me. She spoke with seriousness, but not in an overly stern manner. She was like a parent preparing her son for a recital. “This is going to be huge for me. I need us to go out there and do whatever it takes to win. Some of it may feel a little silly, but trust me, it’s going to be worth it.”
“Of course, Mia, anything for you!” I said.
Mia smiled warmly. “Thank you.” She looked down at my little penis and gave it a look of pity. Back to me, she said, “You know, under different circumstances…” but she trailed off and giggled. She leaned forward and kissed me on my cheek. I felt the blood rush to my cheeks. “Come on then.” She took my hand and led me out of the dressing room and through the backstage area.
She kissed me! I thought to myself, gleeful but stupidly, as if that had been our most intimate interaction that day. I felt like I was more in a daze than ever as we got closer and closer to the stage entrance. She kissed me! The girl of my dreams kissed me!
To this point, my penis had behaved like an old, sleeping dog, unbothered by anything happening to or around it. But this new thought, that she had kissed me —that Mia had given me a kiss —well, this new thought caused something to stir.
“Ladies and gentlemen!” a female announcer’s voice could be heard over the speaker system. “Please welcome to the stage our next contestants, Mia and Liam!”
A dazzling white light blinded me as we crossed onto the stage from behind a curtain. I covered my eyes for a moment as I regained my senses. Quickly, it all started to come into perspective:
Sitting in the audience were at least 300 cheering women, of all ages and looks. There were whistles, guffaws of laughter, there was pointing, clapping, exclamations of “Oh my!” and “Look at that thing!!”
“Oh, that’s the smallest one we’ve seen all day!” I heard from one voice in the crowd.
Mia continued to hold my hand and walked me to the center stage. She released my hand and extended her arms like a game show host presenting the prize of the day.
“Go on, Liam,” she said, laughing along with the crowd of women. “Show these girls what you’ve got!” She snapped her fingers again, and I went into performance mode. I walked confidently to the front of the stage, presenting myself in full view. With each step, my penis and balls bounced ridiculously, the pink bow tied around them keeping them in full view. High-energy music blared over the speakers, accompanied by flashes from the audience’s camera phones.
“Oh, look at that little thing!” I heard one woman squeal. “It’s too funny! Oh, what a sad little penis!”
“I feel bad for her having to handle that thing all day,” said a woman who sounded disgusted. “A pretty young thing like that having to touch such a sad little worm? I hope it doesn’t turn her off of cocks for life!”
Abruptly, the music ended, and the house lights came up. The crowd’s cheering ended, and they began whispering to one another, “Hey, what happened?” “What’s going on?”
There was the sharp screech of a whistle, and we turned to see a woman standing up from the judge’s table. “Stop, stop, stop,” she called out. “We’re calling for an immediate time out!”
“What’s going on?” Mia stepped forward, defensively. “What’s the problem?”
“Mia, this boy clearly has an erection,” the judge said, pointing to my little nub with her pen. The crowd gasped.
“No, he doesn’t!” Mia protested. “Trust me, he’s been soft all day; if he were going to get a boner, he would’ve by now!”
The judge reached out and tucked her pen under the tip of my penis. She lifted upward and released. My penis bounced up and down, but remained poking straight out.
Shamefully, and though it was difficult to tell, I was completely hard. The kiss on the cheek from Mia had given me what was, for me, a totally raging erection. While I hadn’t grown in the slightest, I was at my hardest.
The judge continued, “The rules state that all contestants in the Prettiest Penis Contest must remain totally flaccid for the duration of their performance or face immediate disqualification.”
“That’s not fair!” Mia said. “It’s not my fault this stupid little loser got his dick hard! What do you expect me to do?!”
The judge smiled. “There is one exception to the rule,” she said. “If you can bring an end to this disgusting display he’s sporting, and get him soft again in under five minutes, then you can resume your performance. Otherwise, you’re disqualified.”
There was a wave of excited murmuring in the crowd. “Only one way to deal with that!” one woman squealed from the audience.
“Nobody’s had to do this in years! Oh, this is gonna be good.”
“With a dick that small,” said one of the women from earlier, “This is either gonna be over quickly or it’s never gonna happen.”
The judge pulled a stopwatch from her pocket, clicked it, and said to Mia, “Your time starts now.”
Mia turned back to me as the crowd cheered. “Liam, I know this isn’t what we had planned,” she said, stepping toward me, “but there’s only one thing we can do at this point if we’re going to win.”
The gravity of the situation had not struck me. Under Mia’s hypnosis, I was still in a warm, trancelike state. I legitimately was just happy to be in her presence. The mockery, scorn, and humiliation that my tiny genitals had garnered did not even faze me. Twenty-four hours ago, I truly would have rather died than endured even a nanosecond of what was currently happening. But all my attention was on her.
Mia was now standing before me and reached out to cup my entire manhood again. I felt her moving her fingers on me, with more purpose than before. “I need to handle your erection,” she said. “The only way we’re going to win is to get you soft again, and there’s only one way to do that. Liam, I’m going to need to jerk you off.”
Even in my altered state, I heard those words crystal clear. I let out a wobbly whimper and felt her grip tighten around my short shaft. With great intention, I felt her begin to pull on me.
“Be a good boy, now,” she said, using her other hand to rub my chest. “I need you to cum for me, and quickly.”
The crowd let out a cheer as she got to work. She removed the pink bow from around me to allow as much skin-to-skin contact as possible between my penis and her dainty fingers.
I had never felt such a sensation as this. Obviously, I had masturbated plenty alone in my dorm room, but until today, I had never felt a woman’s fingers on me, let alone the undisputed girl of my dreams. And it was clear she knew her stuff, though at that moment I couldn’t dare to imagine her with any of the men she’d been intimate with.
“Cum! Cum! Cum!” the crowd was chanting. Many of the women were laughing, they’d never seen such a comic display as a tiny little penis being wanked in public like this before.
“I know you can do it, baby,” Mia whispered to me. She had gotten into a good rhythm and was now kneeling before me. She looked up and made eye contact with me, and I was again lost in her big brown eyes. She took her free hand and began to unzip her quarter-zip sweatshirt.
Now THIS is what I’d been waiting for all these years, I thought. Just a peak, a glimpse, a hint at what she was hiding beneath those tight little tops she loved to wear. She unzipped enough to reveal a few inches of cleavage, clearly concealing a larger secret further down.
I let out a guttural grunt, which was picked up on the microphones and projected into the crowd, causing a wave of laughter.
“That’s it, that’s a good boy,” Mia said with the rhythm of her strokes. “Do you like this? Could you imagine seeing more of this?”
Seeing the way her breasts moved ever so slightly in her tight top was driving me wild. I stomped one foot on the floor and grunted again. As she had said before, I was truly becoming a beast before her.
Despite never having had sex, I instinctively began to thrust my hips back and forth, pushing my little nub deeper into the palm of her hand wrapped around me. I was, at this point, simply fucking her hand on stage in front of hundreds of women.
I grunted with each thrust, truly giving it my all, though there was little to give.
“Sixty seconds left!” the judge called out.
Mia looked back at the judge, then up into my eyes, and she looked desperate. She released my penis and looked straight at it. She opened her mouth and, for the briefest of moments, I truly thought she might take me in her mouth right then and there. The thought of her perfectly formed mouth wrapping around my pitiful member, taking me all the way in, nearly sent me over the edge.
But she just spat on me, then brought her hand back up and began stroking again with a vigor I had not known previously.
“Cum! Cum! Cum!” the crowd chanted, clapped, and stomped.
I kept thrusting between her fingers.
“Cum! Cum! Cum!”
“Thirty seconds left!”
Mia stroked, and stroked, and stroked. “Be a good boy, Liam, and cum for me right here,” she brought my penis closer to her exposed cleavage, aiming me, stroking, stroking, stroking. “Cum for me, cum for me, cum for-”
She didn’t have to say it again. With that, I released a pitiful glob, less than a teaspoon, just below her clavicle. She released her hand from me and quickly scooped the cum off of her. She half recoiled, half laughed, and wiped my mess back on my own thigh.
The crowd let out a cheer. My penis, despite never truly growing in size, was now evidently soft from the way it rested upon my tight little balls, which had now retreated closer to me. Mia stood up next to me and held my hand. She looked up at me and said, like she was talking to a dog who had avoided having an accident in the house, “Good boy.”
“They’ve done it!” the judge declared. “Mia has successfully put an end to Liam’s shameful display, and they may continue their performance.”
“We’ve seen enough!” another judge, slightly older than the first, announced. “That was one of the most remarkable displays of feminine power we’ve ever witnessed at the Prettiest Penis Contest.” The crowd let out a cheer in agreement. “The winners are Mia and Liam!”
Confetti rained down from the ceiling, and the crowd erupted. Mia jumped up and hugged me tight, kissing me on the cheek – I felt my little nub press against her thigh, and I let out another joyous whimper. I was melting in her arms.
The judges handed Mia a check for $15,000 and a trophy, which looked a lot like a golden dildo.
I don’t remember much of what happened next. I remember being surrounded by some of the audience members who congratulated me and took photos with me (or more specifically, with my penis).
At some point, Mia snapped her fingers at me again, and the next thing I knew, I was back in my bed, in my underwear. Was it all a dream? It felt so real, so vivid… I looked around, it was pitch black, clearly the middle of the night.
Wow, that must have been the craziest sex dream I’d ever had in my life. I can never tell a soul about that.
I stood up and walked to the bathroom. I stood at the urinal and pulled open my underwear, but when I looked down, I noticed… I had no pubic hair.
The End.

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