Jack's Gap Year

Jack was a cocky 18 year old jock from the affluent suburb of Marsden Heights. He cut a rugged and masculine figure for his age, a killer smile and muscles in all the right places. Jack was psyched to be done with high school and was living it up at a pool party with a bunch of others from the graduating class.

Jack had everything all figured out. Tomorrow, he was leaving his cosy middle class neighbourhood behind to spend a year backpacking through Asia. He was gonna surf, drink and fuck his way through the continent before coming back home next fall to accept a deferred place at a prestigious university out of state. Jack couldn’t wait to get on the plane and begin his legendary gap year, and he didn’t mind bragging about it to anyone who would listen.

His bros high-fived and guffawed with him as he joked about all of the hot Asian chicks he was bound to have in the sack during his adventures. Meanwhile, the chicks were soaking up his ‘worldy’ charms as he regaled them with his travel plans and all the wonderful things he would see and experience – Jack was an expert at playing to his audience, presenting a gentle and thoughtful persona to the girls all while regaling the guys with plans of sexual conquest and wild parties to come.

Yep, Jack was an expert at playing to an audience – any audience it seemed except one containing Jessica. Jessica was the smoking hot 18 year old cheer captain who Jack had been lucky enough to date right up until homecoming when she caught him getting a handjob from her best friend Kirsten behind the bleachers.

Jessica remained deeply unforgiving of her ex-boyfriend and refused to engage with him throughout the pool party. This bugged Jack like nothing else, I mean who was she to resist his charms? He had dated plenty of girls before that had caught him messing around with other chicks, but they all came back to Jack in the end. Jack knew his impressive 12 inch salami-thick dick was his chick-magnet, and he knew sooner or later Jessica was bound to crack. He smirked as he took a swig from his beer watching her from across the pool….

A few hours later and the party was getting wilder, everyone was at least tipsy if not completely drunk, EDM blared from Bluetooth speakers, the guys were practicing their cannonballs and the chicks were watching them laughing from the sides of the pool.

Jack used the commotion as his opportunity to slide up next to Jessica as she stood by the edge of the pool, sipping a cocktail that was resting on the side. Jessica was as hot as ever, Jack could hardly bring himself to avoid staring at her assets. But he knew she was mad at him and would need a bit of that patented ‘Jack’ charm to get her back on his good side.

“Hey Jess, how’s it going?” He demanded more than asked as he pulled up beside her, trying to act confident, putting his beer down as she turned away from him.

“Come on girl, don’t be like that!”

“Not you girl Jack, you made that very clear” she replied cooly as she stirred the straw through her margarita.

“Look babe, it was all a misunderstanding. And hey, I’m going away tomorrow and I don’t want us to leave on bad terms, ya know?”

Jessica turned to face him, looking the big dumb jock up and down. “Oh really, is that so?... What did you have in mind?”

“Ya know” he said, not so subtly tugging on his monster cock through his board shorts “we could take a visit behind the shed over there, just once more for old time’s sake”

Jack shot her the kind of cocky smile that made her want to throw up, but she played it cool. This was gonna be her one opportunity to humble this peabrained fuck-machine and she was gonna make it worth her while.

She leaned in, letting her breasts hang tantalisingly. “Ok big boy, one last time – I’ll meet you over there in a few minutes, but don’t follow me straight away, I don’t want it to be obvious…”

Jack licked his lips as Jessica wandered over to the shed at the end of the garden. He chugged the last of his beer, overcome with amazement at his own prowess. “Still got it” he muttered to no-one in particular as he hopped out of the pool, slipping away unnoticed by his friends.

Jessica was waiting for him, dripping wet from the pool wearing her tiny bikini. 

"Fuck, you're... wow, I mean just wow" The usually confident stud was temporarily lost for words.

Jessica pulled him in for a deep, passionate kiss. A wave of pleasure washed over his body as his torso pressed into hers. 

Man, he had missed this. He had been with a hundred girls but no-one knew quite how to press his buttons like Jessica did. He felt his dick bricking up as she ran her soft dainty hands over his impressive pecs then down over his washboard abs before resting at the waistband of his soaking wet board shorts.

"Woah, you're keen to see Jack Junior huh?" he smirked. Jessica worked hard to force a smile and suppress the eyeroll that was building within her. 

"Shut up stud" she whispered into his ear as she forced his mouth back into a deep kiss while simultaneously plunging her hands down the front of his shorts. 

Jack moaned as both her hands brushed passes his rapidly hardening dick. Fuck, this was gonna be good. And to think, he almost left the country without getting off with Jess one last time.

Jack's moans continued, as he made out with her but something was suddenly off.  

His eyes opened and he pulled back from the kiss just as he felt Jess’s hands sail completely past his mighty salami dick and instead latch onto each of his hefty balls. His eyebrows furrowed as he let out a short gasp followed by a “Ooohh… easy… easy baby.”

Jessica was unmoved. “You really thought I’d want to do stuff with you again huh? After you cheated on me with Kirsten at homecoming!?” She whispered aggressively into his ears, punctuating every point with a sharp squeeze of his naked nuts.

OOooowwhhhhh…. Jack groaned, knees ever so slightly buckling as his balls got mashed between her palms.

“Unghh.. ok baby, I get it, I do.”

“Do you Jack!?” She asked firmly, giving his balls another long hard squeeze causing him to gulp and hunch over, his manly chest rising and falling with increasingly deep breaths as it rested on her upper torso, his head supported by her collarbone as he gasped for air.

Gingerly he reached down to try and free his balls from her grip, but as he reached his own waistband Jessica unleashed hell on his nuts with a squeeze so mighty it must have crushed his bollocks to within 1/3^rd of their normal width.

“AARRRGHHHHHH!!!!!!!!!” Jack let out a mighty roar – one so primal and full of terror that it startled even Jessica.

“Shh… shhh!” Jessica whispered leaning in close as she slightly relaxed her grip. “Now, now, we don’t wanna make a lot of noise do we? I mean you don’t want everyone to know that your big ballsies are getting hurt by a girl do you?”

Jack whimpered, gulping as if it could swallow up his pain.

“I mean what would people think? Jack the Man getting beat up by little Jessica? I don’t think a lot of girls would be very interested in you after that, do you?”

Jack glared down at his crotch, seeing her hands still busy working away at his nads inside of his board shorts, but he could do the math. He knew he could probably overpower her, but if he moved his hands any closer to hers she was just going to squeeze like that again and incapacitate him before he could reach his nutsack.

She literally had him by the balls and there was nothing he could do about it. With a restrained, frustrated grunt he moved his hands away from his waistband and instead brought them up over Jessica and slammed them onto the garden shed for support.

Jessica smiled, she was winning.

“Good boy” She cooed softly as Jack’s muscular arms trembled either side of her head as he tried to keep himself up. “Now, let me tell you how this is gonna work. I’m going to get all of my anger out of my system and you’re gonna take it like a man. Understood?”

Jack glared at her.

“Understood!?” she asked again with another sharp squeeze accompanying it.

“Understood!” Jack stammered, fighting a cough as another wave of pain washed over his balls.

She could see from the fury in his eyes just how much he wanted to fight back. I mean, here he was – football player, gym rat, battle hardened pecs, killer biceps, all that time lifting weights and drinking protein shakes – for what? Now, when he really needed to, he was powerless to protect his own manhood. And that was driving him crazy inside.  

“Good” came Jessica’s cold reply.

Slowly but surely she began to twist Jack’s balls around their chords, Jack’s lips let out a high-pitched squeak as he stared pleadingly into her eyes. “Please” he managed to whisper, biceps and legs really shaking now.

“There, there” she whispered back to him “it’ll all be over soon. Just close your eyes and think about your awesome trip, stud.”

Jack cursed as his dick continued to respond to her sexy voice despite the assault she was dealing out to his nuts. The tenting of his board shorts had become frankly ridiculous by this stage, his rock hard dick straining violently against the velcro fly of his swimwear.

The dumbstruck hunk gulped as he heard the tell-tale rzzhhhh-RIPPPPP of velcro parting. Immediately followed by the meaty THWACK of his dick slapping against his abs.

Jessica smiled as she say his thick and veiny member burst out of its constraints. “Oh, someone’s enjoying this.” She deadpanned much to Jack’s chagrin. I mean, who the fuck would *enjoy* getting their balls tortured?

“AH! Fuck! Come one now Jess, you’ve made your point” He stammered, a bead of sweat dripping from his brow, running down his face before falling and landing onto his purple cockhead with a wet SPLAT.

“Hmm… not quite”

Jess used the parting of the velcro to haul Jack’s hefty bollocks out of his shorts as he kept them clamped down in her hands.

She took a moment to observe the meaty orbs as she rolled them in her hands in Jack’s lightly haired sack. It was funny, she thought, that boys let themselves be so controlled by these things. They really weren’t all that impressive, honestly, they’d probably be better off without them…. Oh well.

Ignoring one final pleading glance from the jock’s puppy dog eyes, Jessica went in for the kill, mashing his two balls together like a giant lump of meat so that they were simultaneously being crushed not only by her hands but by each other.

Jake’s face went beet red, his fists pounded on the shed above Jessica’s head as he desperately tried to hold back a mighty scream.

His dick throbbed with every squeeze but held out for another couple of minutes before suddenly starting to pull back in their sack, his chords straining aggressively against the pull of Jessica’s hand.

Both of them realised exactly what was happening, for Jessica it was a moment of triumph, for Jack one of utter humiliation. The stupefied jock started babbling and groaning incoherently.

“Jess… no… Jess… baby… don’t… UNNGHHHH…. You’re gonna… AGHHHH…. STOPPP…. PLEASE…. YOU’RE GONNA…. OOOOFTT… I’M GONNA…”

Jess just smiled gleefully at her humiliated ex-boyfriend. The senior year’s heartthrob, the overconfident jerk who thought his muscles and his dick meant he could do whatever he wanted, no matter how much he hurt the girls stupid enough to fall for him. Here he was, reduced to a bumbling idiot as his useless muscles flexed and violently shook all because of what she was doing to his weak, quivering balls.

“Yeah, you are Jack. Isn’t that what you wanted? One last time getting off, with me? Or because of me at least? Right?”

Jack shook his head in frustration, grinding his teeth as he continued to supress a guttural scream like no other.

“Well you’re gonna get your wish. And when you do, just remember, I’m not your Jess anymore. I’m Jessica.”

And with that she released Jack’s balls while shoving his heaving chest off of her causing him to stumble two steps back. Before he could so much as move an inch, her left fist struck out like a jack-in-the-box and punched him square in the ballsack, while her right palm shoved the hapless jerk in the back causing him to stumble a few steps forward, just out from behind the protection of the shed.

For Jack it all happened so fast, one minute he was hunched over his ex, his boys getting the torment of their lives. Then within the space of about half a second he felt her pushing him back, then AWHHHHHH – NOT HIS BALLS!

But before he could even register the pain, he was pushed out from behind the shed into view of the whole party still hanging out by the pool. A familiar feeling washing over his groin as he stared down just in time to see his mighty dick erupt from the force of Jessica’s last punch to his nads spraying a blast of thick cum right into his face and then all over his abs and chest.

He spat out in disgust as the partygoers reacted to the sudden spectacle. The guys were either stumped into silence, or in some cases laughed. But the shrill, panicked scream of the girls sent a shiver down Jack’s spine.

Everything happened so fast, within seconds cries of “PERVERT” rang out across the backyard. Some of the guys were trying to diffuse the situation, seeking to calm their terrified and shocked girlfriends. A couple of Jack’s closest buddies shielded his modesty and passed him a towel to help him clean up. Other guys were taking sides with their girlfriends and telling Jack he needed to leave.

“NO! THAT’S IT! THIS IS THE LAST STRAW!” Came a yell, Jack was almost too dazed to see who was speaking as he crumpled to the floor, a cum-laded towel in one hand as the other cupped his aching nuts.

“That is sexual assault. Exposing us all to that. It’s not acceptable and I’m calling the cops.” Jack blinked through bleary eyes as a couple of his buddies parted around him to see that Kirsten, the girl he’d cheated on Jessica with was addressing the crowd of gathered girls who were murmuring in agreement.

A couple of the boys objected, “Look, Jack’s a dumb prankster. I know that was wrong but let’s not call the cops”.

“No Tyler, this is too much. If you turn a blind eye to this stuff it just gets worse.” Came Kirsten’s response as she grabbed her phone from her bag and started calling the cops.

“No…. unghhh… wait… it was Jessica.” Jack croaked between half-sobs as he lay soothing his battered balls.

At that point, Jessica appeared from behind the crowd having emerged from the direction of the house.

“Ummm… what’s going on here? I was just in the bathroom.” She delivered convincingly.

A panicked look flashed over Jack’s eyes as he realised how sneaky she’d been, using the cover of chaos to slip out from the other side of the shed and walk behind the bushes that lined the garden to successfully re-emerge from behind them near the exit from the main door of the house.

The girls surrounded Jessica ‘filling her in’ on Jack’s disgusting act of indecent exposure.

 

***

Nearly an hour passed before the cops turned up, two officers from the local police department.

Jack was still groggy and sitting on the edge of a lawn chair when the two officers approached him and asked him what had happened. He could hardly make sense as he tried to explain how Jessica had lured him to the sheds, busted his balls and then exposed him in front of everyone.

The cops shared a quizzical expression as they examined his figure. Jack was a tough, super muscular guy – especially for a recent high school graduate. It seemed utterly implausible that he’d ever be overpowered by a female, especially not a 5 foot 18 year old girl.

The officers took statements from the others in attendance – not one person corroborated Jack’s version of events.

It became pretty clear when they found out Jessica was Jack’s ex that he had only mentioned her presumably as a form of sabotage after realising the severity of his ‘prank’ when others started talking about calling the cops.

They’d heard enough. Jack was still babbling on about his nuts as he was read his rights and hauled to his feet. The ice cold metal cuffs wrapping perfectly around his wrists as an abrupt *CLICK* made the fact he was really being arrested sink in.

Jack looked around begging for someone to step in and tell them the truth, only for his heart to sink as he realised no-one really believed him. The girls all glared back at him in disgust, his bros sheepishly staring at their feet. In their eyes, Jack was living out the exact kind of warning scenario the boys had always heard about – the prankster who took something too far and now had to face serious consequences.

As the humiliated stud was marched to the back of the waiting police car, he gently began to sob as everything came crashing down all at once.

The door slammed in his face as he was driven off down the driveway as his friends watched.

As the cop car disappeared down the street, the partygoers headed back inside, deciding to pack things up rather than continue. As they gathered their things, Jessica made her first approach to Kirsten since homecoming. “Hey, that was really awesome how you stood up and made the call to say enough was enough.”

“Thanks Jessica. I just couldn’t stand by and let that creep get away with something like that. A joke’s one thing, but that’s just too far.”

“Agreed. Look, I know it’s been a while but why don’t you come back to mine after this, I think we’ve got a lot to catch up on.”

Kirsten was touched by the expression of forgiveness. “Yeah, I’d like that a lot.”

The two friends walked back to Jessica’s place together, reunited once more talking about all their plans for the year ahead. 

Jack on the other hand was certainly in for one hell of a gap year.

Unfortunately for him, he didn’t get to see the world after all, in fact he didn’t even leave the county. But he did get lots of what he was asking for during his 14 months in the local penitentiary: dorm style sleeping arrangements, meeting lots of interesting people, having experiences that opened his eyes and making lots of lasting memories… just not the kind he wanted to remember.