Annie's Dick Measuring Contest Adventure

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5 chapters · 5688 words · Read 2 times

Annie is an ugly 18years with no sexual experience. One day, during a house party,takes a ruler and offers a blowjob to the guy who proves to have the bigger dick, lead into a dick measuring contest.

Chapter 1: Introduction

The house rocked like the beat of a drum as Annie clutched the keg with sweaty palms, maneuvering it through the pulsating mass of bodies that had invaded the usually quiet suburban dwelling. The chorus of voices singing along to the latest pop song was piercing enough to deafen an elephant. Or was that the Beats by Dre pumping out tunes from someone's phone? Not that she'd bother trying to differentiate these days.

She was already maxed out on conversations she could take that revolved around trivial things like Bassnectar and their latest psychedelic experiences. Who even knew what Bassnectar was, not like she'd ever admit it?

Glasses perched precariously on her nose, she surveyed the sea of writhing bodies, looking for her next victim. She spotted Matt first; he was standing with a group of people, sipping from a red cup just like every other person in the room. It's time to unleash the beast.

Annie rolled her shoulders back, collecting herself before she stormed through the crowd. She approached Matt like a lioness stalking her prey.

"Care to help a damsel in distress?" she challenged, nodding at the beer-laden keg that was teetering perilously close to a tipsy sophomore. Matt glanced at the scene unfolding in front of him before shrugging and abandoning his abandoned conversation. The awkward trio moved together swiftly and rescued the keg from its precarious position - much to the relief of the sophomore and anyone within a ten-foot radius who feared the worst.

"You know, you should be more careful," Annie teased Matt as they returned the keg to its throne of black tap handles and keg cups. "Reckless behavior like that could get you into a world of trouble."

Wiping the foam from his upper lip, Matt quipped, "Oh? Should I expect a visit from the cock police then?

Or maybe I should enlist in your training academy so I don't inadvertently fall prey to a fate worse than death." Matt said, smirking at her from behind those mischievous green eyes.

"Well, you're already in luck, because I just happen to be hosting a little event in the basement that could help you with your misdemeanor."

Annie and Matt lingered in their banter long enough to intrigue a group of onlookers.

With the entourage of curious party-goers egging them on, the duo descended into the basement - now a makeshift arena for Annie's competitive spirit to reign freely.

As they descended the creaky wooden steps, Annie motioned for Matt to sit next to her on a worn-out, velvet love seat where the bowels of the house came alive. The neglected corner was littered with thrift store relics, a remnant of someone's abandoned living room - a perfect place to appetize their adventurous souls.

Annie cast her glance around the motley assortment of figures now peppered across the basement. Max - one of the better looking, charismatic seniors - stood leaning against a far wall, chatting up someone with his trademark smolder.

She felt her heart thudding in her chest as she snatched a wooden ruler from the coffee table. She noticed Max's gaze tracking her movements despite the swirl of people around him. A slight smile tugged at the corner of her lip. The game was on.

Annie scanned the room, fixing her gaze on each of the young men in attendance. Their eyes widened as realization struck; they were to be the guinea pigs in Annie's experiment. She dangled the wooden ruler like a mic wielded by an aspiring rockstar, swaying it playfully from side to side, generating electricity that could truly be touched and felt by everyone present.

"Gentlemen," Annie began, her voice wavering but sure. "I'd like to invite you to partake in a little activity.

I am in search of a winner, someone who can offer the most impressive display of their - *ahem* - manly assets. If you are feeling adventurous, take a seat on this throne of absolute power!"

Annie flourished her arm towards and over a tattered velvet stool, placed on a dingy stained rug, to mark the spot of this newfound masculinity test. With just the right hint of confidence, she summoned the attention of every soul in the basement, her voice cutting through the low hum of conversations and blasting of the music with surprising ease.

As her words finally sunk in, a ripple of surprise, chuckles, and cheers ran through the gathering.

Max's laughter pierced through the room. He had an irresistible grin that curled just enough at the edges to make one question his intentions. "Someone's been dying to throw a party like this, haven't you?" he hollered, with one eyebrow raised as he nudged his way through the crowd.

"Well, we've gone through the usual debauchery, Max. Dares, truths, and a lingerie twister tournament that went just a teensy bit too far. Why not something more... scientific? I figure we have a lot of curious minds in here, so let's satisfy them a little, shall we?" she said, playfully waving the ruler again while maintaining eye contact with Max and his sculpted smirk.

Smattering of laughter filled the space, but the guys had grown contemplative; her casual quip seemed to rouse their curiosity. "What price glory?"

"Seriously, what's at stake?" Matt pressed his hands onto his knees with renewed interest, raising an eyebrow at Annie.

“I’m gonna suck the bigger cock” Annie said

with a confident smile and a sly wink.

The room vibrated with a new surge of rambunctious conversations as the twenty- something partiers present whispered to each other, sometimes chuckling with disbelief.

A thin blonde wearing bright red lipstick raised her hand to get Annie’s attention, interrupting her thoughts.

“Are you serious, Annie?” she asked.

Annie blinked twice, unmoved, staring at Max and his mischievous glare, which made the hairs on her arms stand on end.

“Absolutely,” she said evenly.

In a single moment, she watched as fear, excitement, and shame collided on the faces of those surrounding her. A flurry of emotions coursed through the room, a nuclear cloud of hormones and unspoken thoughts swirling in the space, just begging to break free of its ribbon-tied limitations.

Annie stood frozen when Max shattered the fleeting moment of awkwardness by breaking into a dashing smile. He was the first one to step up, abandoning a voice of doubt that would have otherwise persuaded him otherwise.

One by one, they followed, sitting themselves onto that “throne of power,” as Annie so eloquently referred to that unassuming velvet stool.

As the crowd thinned, only a handful of courageous men remained standing, nervously stuffing their hands into the pockets that lined their faded jeans or grabbing a newly-refilled cup as a nervous crutch. Among them was Max, his confident stature and smoldering eyes surveyed the bustling room in amusement.

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