GaySherbert

[This is another slapdash addition to a story I began a few days ago. It's probably rough around the edges as I kinda threw it together, like the last two parts. As always, feedback and suggestions are always welcome.]

Whatever it was that your bros found so compelling about your receptivity to wedgies, it was clear that they meant business. They must have privately coordinated the events immediately following your departure from the burger joint, though you couldn't even guess when or how they would have had time to do so.

The moment your seatbelt was fastened in its buckle, it suddenly and powerfully tightened against your torso. The guy behind you was pulling at the seatbelt from behind with all his might, securing you helplessly in place. Before you could even react, a second pair of hands had found their way around the seat and once again into the back of your pants, impressively maneuvering a massive wedgie as Damien, cackling along with the rest of them, started the engine and began to drive.

You kicked and thrashed in the limited legroom of the passenger seat as the waistband climbed with shocking rapidity and ease, quickly attaining the goal of being hooked over the top of the headrest. So powerful was the restraining force of your seatbelt, pulled from behind with immense force, that you couldn't even raise your arms to reach up and release the waistband from the headrest. But even if you could have, would you?

'You seriously need to stop squirming and chill out, wedgie boy,' Damien said, reaching across from the driver's seat to tousle your hair playfully, the way an uncle—or a bully—might have.

You could only stammer, the onslaught of sensations almost so intense as to impede coherent thought. 'I... oh, God... fuck, I'm not—'

'Damien's right, wedgie boy,' said Trevor's voice from behind you, followed by a wet, slippery POP noise that sounded like something being inserted into a mouth and quickly withdrawn. 'You need to chill the fuck out and try to enjoy yourself already.'

With no warning, a pair of big, meaty pinkie fingers, obviously coated with copious quantities of saliva, were jammed into both your ears at once. The involuntary full-body shudder that this triggered was humiliating enough, to say nothing of the groan of visceral, high-octane pleasure that this forced you to produce. The fingers did not retreat immediately but instead twisted and wriggled aggressively, as if to wring as many gasps and moans and expletives as possible from your mouth, by force. Though your ear canals were fully obstructed, you heard the entire car erupt with laughter at your ecstasy-torment. You didn't know if the constriction you felt in my crotch was due more to the gigantic wedgie you still had in, or to the fact that your erection, straining against your tighty whities, must have been hard enough to cut diamonds.

You shut your eyes, tight. You didn't entirely know why, but it felt like you had to, perhaps as an instinctive reflex to prevent your brain from literally short-circuiting on the veritable deluge of embarrassment, pain, helplessness, and extreme pleasure that was assaulting your neural pathways with unrelenting brutality.

'Dude, he fucking loves this so much, it's insane.'

'Our little wedgie boy's horned up out of his fucking mind right now.'

'Hey, wedgie boy, smile for the camera!'

You opened your eyes to see a phone being held in front of your face at arm's length. It was Jack who held the phone, as the only one in the van's middle row whose hands weren't fully occupied. The front-facing camera was on, and the second your eyes snapped open, the digitized camera shutter clicked, signalling that a photo had been captured.

Jack was leaning into the frame from the opposite side of the van, gesturing towards you with his thumb and an exaggerated facial expression that said 'Get a load of this!'

Visible directly behind you was Aiden, grinning maniacally as he continued to pull your seatbelt towards himself with incredible force, leaning back in his own seat to maximize his leverage.

Leaning in from the middle seat was Tyler, whose thick pinkie fingers still clogged your ears and who was beaming at the camera like he was at his high school graduation all over again.

In the back of the van were Adam and Chris, both laughing so hard that they looked like they were on the verge of passing out or giving themselves heart attacks.

Just barely in frame was Damien behind the wheel, eyes on the road and a jocular smirk on his face that said 'Boys will be boys!'

In the middle of the picture itself was, of course, you. The headrest was fully enveloped in the white fabric of your briefs, and Tyler's fingers were still plugged deep into your ears. Your face was flushed red, eyes wide with embarrassment and terror, but your pupils blown so wide as to make your arousal impossible to deny.

It was too much. It was too hot. You needed it to stop, soon, or else...

'Guys,' you pleaded, trying to wriggle free and actually managing to get Tyler to retract his saliva-covered fingers from your ears. You were so horrified by what you felt was going to happen that your voice was barely above a croak of timid protestation. 'Guys, I—'

'What is it, wedgie boy?' Damien asked. 'You'll have to speak up, we're having too much fun to hear you.'

You tried to keep your voice as level as you could, but it was becoming a mounting struggle. 'I... I can't... It's too much...'

'"Too much"? Tyler cut in, 'Bro, we've literally seen your locked photo gallery. There's no such thing as "too much wedgies" when it comes to your ass, that's for sure.'

'No, you don't understand,' you said. You felt the walls that had miraculously gotten you through the morning's earlier three-hour wedgie session beginning to crumble. 'If you don't stop, I'm gonna... gonna...' You fought hard against the waves of orgasm crashing against your consciousness, like you were an ancient mythic king in a parable, trying, in his hubris and vanity, to hold back the tides of the ocean.

'Gonna what? Cream your tighty whities just from a wedgie?' Amid the continued snickering from the bros at this comment, Aiden took the liberty of unhooking your waistband from the headrest and pulling viciously towards himself, suddenly intensifying an already monster wedgie without warning.

You groaned helplessly as the camel's back finally broke. Your overfull balls emptied impossible amounts of semen into your briefs, blasting rope after rope of pent-up jizz into your tautly pulled tighty whities. It was, by far, the most pleasurable climax you had ever experienced, tainted only by the horrifying reality of the context in which it had occurred.

A silence had fallen over the friend group. The car had come to a halt. Surely this was the end of the fantasy come to life, and also of your friendships with six other guys whom you had loved and trusted as brothers.

'Dude,' Tyler said, 'I didn't even know you could do that.' There was another pause. You said nothing. You wanted to disappear, to die. It was Tyler who broke the silence again, but now in a different tone. 'So I guess that gives us something to work towards with this wedgie boy, huh?'

There was a hearty wave of agreement that rocked through the car, and a resumption of the general, jovial atmosphere as before. You were in complete disbelief. 'Something to work towards'?

Damien clapped you on the shoulder. 'Bet you were holding that one in all morning, huh, wedgie boy?'

'He definitely sounded like it, from the way he was moaning back at your place,' Tyler added.

'Dude, I thought he was gonna bust when I gave him that piledriver wedgie back at your place,' chimed in Chris. 'He seemed so into it, but I guess he was actually holding back!'

The mortifying experience of having revealed to your close friend group that you had a 'thing' for wedgies, complete with copious photo and video evidence, had been the most embarrassing moment of your life. But embarrassment quickly gave way to arousal and then, naturally, to ecstasy as the events of the morning and afternoon unfolded.

You felt as if your boner might tear right through your briefs as your bros pounced on you, eager to make good on their part of the arrangement. Far from wanting to forget about the whole thing, they unanimously saw this as an opportunity for a huge win-win. They would get a means of channelling and expending excess academic stress through your waistband, and you would have an erotic fantasy brought to life. Where was the downside?

For three straight hours that morning after, your tighty whities were subjected to constant stretching, pulling, tugging, and yanking. Every time a slow, deliberate pull was administered to your waistband, it felt as though the resultant groan of pleasure were being forcibly extracted from deep within the core of your being, much to your bros' amusement and—could it be?—their own increasingly apparent arousal. Your rational mind screamed at you to resist, to call it all off to preserve your dignity and possibly your friendships, but your animal mind overrode all such concerns. The pleasure was simply too intense to be defied.

'Goddamn,' marvelled Damien, straddling you from above with your waistband bunched up in both fists, you lying prone on the floor. 'I didn't even know they made underwear this stretchy!'

'He probably buys them just because of that,' Jackson opined from behind you, crouching on the floor with one of your ankles in each of his hands, holding you down to maximize Damien's leverage as he pulled. 'I'm sure wedgie boys like him need the stretchiest briefs money can buy.' It went without saying, of course, that Jackson's taunting observation was, in fact, entirely correct.

'Five more minutes, Damien,' announced Tyler from the sidelines, 'then it's Aiden turn.' Tyler had been using his phone's stopwatch function to make sure everyone got an equal amount of time with their new human stress toy. Damien promptly redoubled the strength of his ministrations to make the most of his last remaining minutes.

Aiden, for his part, was scrolling through your phone with the purpose of educating himself beforehand on proper wedgie methods, techniques, and terminology. He wanted to make the most of his session, and with the contents of your Twitter feed, your Instagram DMs, your Tumblr page (and more) at his fingertips, he was both amazed and illuminated by the amount of helpful information you were involuntarily providing the entire friend group with.

Afterwards, as your group was accustomed to doing on Saturday mornings, you made your way to a local burger joint for some coffee and greasy, high-calorie grub to help wash away the lingering residue of your hangovers. To a spectator, everything might have seemed as it always was. Except, perhaps, for you. Far more quiet than usual and wearing an unreadable expression on your face, your mind reeled as it tried to process the events of the morning, as well as with their long-term implications. It was, by far, the hottest thing you had ever experienced. It was a miracle you hadn't creamed your briefs just from the sheer, relentless eroticism of the whole situation. But even if you had, would your bros have even cared?

The rest of the group behaved largely as they always did. The staff here were used to how you guys were, to your routine. You would come here every Saturday to chase your hangovers away, sometimes boistrous and inconsiderate as college guys were wont to be. You would boast a little too loud of some enviable sexual conquest made the night before, or of the attainment of some coveted set of digits from a sorority chick. Or, after less eventful Friday nights, one might brag about how well he'd whooped another's ass in this or that videogame. In a word: the usual and expected banter.

Things were different now. To be fair to them, your friends held up their end of the bargain, namely to keep this all a well-guarded secret. But every time the area around your table was empty of potential eavesdroppers, one of them would lean forward a bit to speak in a hushed, conspiratorial whisper, leering at you with a gaze half-menacing, half-hungry.

'Fuck, dude, seeing your face covered in white for the first time last night might have done something to me.'

'Did you guys hear how much this wedgie boy moaned when I started bouncing him? He sounded like he was gonna bust right then and there.'

'What a fucking night. We're gonna have to start making this a regular thing.'

There were enthusiastic nods all around. My heart pounded so fast and hard it felt like it was gonna smash through my ribs. Was this something that the guys were going to lose interest in after a few days, maybe a week? It was possible, but the manic intensity with which they lay violence to my tighty whities that morning and the night before suggested otherwise. I gulped. The future stretched before my mind's eye, both deeply terrifying and indescribably exciting. How long would it go on for? Weeks? Months? Years, even?

You don’t know who it was, but maybe it was a mistake to wedgie one particular nerd who (unbeknownst to you) spent his free time dabbling in the esoteric practices of the occult. The curse he put on you certainly changed your outlook, to say the least.

It began with the sudden sense that your usual boxers were uncomfortable. Not just one pair that had perhaps gotten a bit old, but all of them. Even your boxer-briefs and backup trunks felt somehow wrong. A stubbornly persistent, infuriating, and somehow inarticulable sensation of discomfort beleaguered you for two full days until, on the third, you could take it no more.

Thank God for the self-checkout machines at the mall, with which you hastily scanned and purchased not one, not two, but five packs of briefs for yourself before stuffing them in your backpack, desperately hoping nobody saw you. And not just any briefs, but brightly, uniformly white briefs—in other words, tighty fucking whities. How would you even explain yourself if you had been spotted, recognized, approached? You, still visually as much of a frat boy dudebro as ever, shamefacedly buying thirty pairs of tight, white briefs. Indeed, you couldn’t even begin to explain it to yourself.

You’d found the solution to your inexplicable discomfort, that much was certain. You just had to make sure that there was no chance in hell, under any circumstances, that anyone could ever catch sight of your waistband, lest they deduce what now hid underneath. The most fearsome bully on campus, now a full-time tighty whitie enthusiast! You’d never live it down if word got out.

But the consequences of the curse were only just beginning. Your mind was increasingly beset by visions, memories of the most intense wedgies you had ever dished out to the unsuspecting nerds you had once tormented. Though your desire to stretch other guys’ briefs had suddenly vanished, your inner preoccupation with wedgies had increased tenfold, if not more.

You remembered Damien, whose waistband you had cruelly used one day for impromptu bicep curls in front of twenty people. You remembered Eric, whom you had hung by his briefs for twenty minutes before he managed to bounce enough to rip them. You remembered Kyle, whose tighty whities were so stretchy that they could cover his entire face without ripping. You remembered them all, almost involuntarily, not because you wanted to replay the scenario as it had really happened. What you wanted was to experience it from the other end.

A week after the curse had first begun to afflict you, you finally gave in. A piece of exercise equipment in your basement would do, would be strong enough to support you fully off the ground without risking damage to the structural integrity of the apparatus. You were just curious, you told yourself. You just needed to try it. Just once, and that would be it. Then you would go back to being normal.

The sensation of your underwear tightening against your skin was like nothing else you had ever experienced. You thanked your lucky stars that no one was home to hear the deep, involuntary moan of pleasure that issued forth from your mouth as you sank into your first-ever self-administered wedgie. Your levels of physical and psychological satisfaction were utterly maxed out as you dangled there, a full foot off the ground, your brain practically assaulted by powerful waves of unexplainable ecstasy. The words ‘WEDGIE BOY’ pounded and throbbed relentlessly against your consciousness, echoing in your ears and dominating the screen of your mind’s eye, as if branding you with your new identity until you submitted to it entirely.

‘Morning, bro.’

As the words of your best friend roused you from your slumber, you became immediately aware of two facts: first, that the throbbing pain pounding through your skull indicated that you were very, very hungover; and, second, that you were blinded by a sea of white. Massaging your aching head, you felt the familiar fabric of what could only be one thing, namely, your briefs, stretched over your head and hooked securely beneath your nose. The additional, not-too-unpleasant pain which you then became aware of, concentrated around your groin and ass, confirmed your mounting suspicion that you were in an atomic wedgie. This was a predicament you had been in countless times before, but only by your own hand, in total privacy, and never in the company of anyone you knew. The taste of stale alcohol was still on your breath when you managed to croak, ‘What... what happened last night?’

Your friends gave you the run-down of the events of the night before. It had started as a normal Friday night with the bros, drinking and chilling and amusing yourselves as you did every week. But when your friends reached the next point in the narrative, your blood froze. Maybe you’d not eaten enough beforehand, or maybe you didn’t pace yourself as well as you should have, but eventually your intoxication reached such a point, your disinhibitions lowered to such a degree, that you confessed to your entire friend group that you had a ‘thing’ for getting wedgies. Shame and humiliation coursed through your veins at this revelation, and it only got worse from there. You had, in your drunken stupour, shown them photographic and videographic proof to verify your claim, flipping gleefully through your phone’s private media gallery as you flaunted image after image of yourself. In one photo, you were shown suspended a good two feet off the ground by your underwear, clearly in a self-inflicted predicament. In another, you were showing off a clandestine shoulder wedgie hidden under your T-shirt. In each and every one of them, though, only one conclusion could be drawn. You were very much into this, and you always had been.

You quickly pulled your waistband from your nose and let it snap back in place at your lower back. You knew with certainty that, though you hadn't looked in a mirror, your face had surely gone a deep shade of crimson as you profusely apologized, begged forgiveness, and pleaded that they just forget you had said anything at all. You couldn't even make eye contact with any of them as you swore it would never happen again and that you needed them to just act like last night had never occurred in the first place. When you finally managed to look up at them, though, you didn't see the looks of discomfort, disgust, or contempt which you had expected. All around you were devious, knowing smiles which only added to your acute sense of embarrassment and confusion, before it was explained to you how the night had proceeded from that point onward.

As it turned out, your bros had been more than willing to indulge you, and they themselves had more than enough proof. You were shown dozens and pictures and videos, taken throughout the night, of you in all manner of wedgie-centred predicament. Your eyes went wide as you were shown shots of you, utterly and shamelessly blissed out in one extreme wedgie after another, your bros enthusiastically fulfilling your fantasy of a lifetime. The recordings jogged your memory, and your mind began to piece together the events of a night that almost defied belief. To have your tighty whities pulled, tugged, yanked, and stretched all night long had felt a hundred times better than any wedgie you'd ever given yourself, and the mere recollection of the previous night, however fragmentary, was more than enough to prompt an involuntary stirring in your traitorous loins.

'Don't worry, bro. Your secret's safe with us,' one of them said with a pat on your shoulder. 'As per the arrangement, anyway.'

This last part was puzzling. 'What arrangement?' you asked quizzically. There were snickers all around, and you felt your friends starting to close in around you.