Untitled

Would you rather have to get an increasingly strong hanging wedgie on a game show in tighty whites,

 or 

This was Josh’s new life:

Just one day after his humiliating wedgie at the hands of his peers and he’s now officially the wedgie bitch of the campus frat. As these two frat bros has already told him, “we can’t have fucking dweebs who cum from having their little undies tugged crashing our parties”

“You want out? Too bad!”

My friends decided to leave me in my new toy while they went to the other room to play with legos (and the vibrator)

Tonight was a good night for me, won quite a bit, the others left not long ago, i was telling him I'd be getting ready myself too when he asked for one more game, i had woon most of his money, i could give him a chance to win it back. I still had time, so i told him that given my luck of today, chances were not looking good for him, he still insisted.

As predicted, he lost three hands in a row, betting big each time, sitting without any funds opposite of me at the table then. But he wanted to go on, one more, he asked, but having no money to bet i asked what he'd think on that, he did not know, but kept begging for one more game.

In the background his boy still struggled in the bouncer, i looked at that and grinned, looking at him then i told him about an option: I'd put in the amount of money he lost this evening, he'd bet time in the bouncer. If he won, we'd be done for tonight, if he lost, he'd have to spend every poker night, which we held every other weekend, the whole day in that bouncer the way he kept his boy usually. Since i was putting up 1500 bucks, 15 of those weekends it would have to be. He agreed without thinking.

Cards dealt, i had a great hand, a straight flush, eight to queen, no concern about that, i did the 'official' bet of the 1500 bucks, he thought a little, then said: 'I of course match that, but i want to raise, what would it take to get you perform an 'all in' with everything you won tonight?'

That was a surprise, i thought a little, cards exchanged, cards on the table, cards in my had, chances of loosing were extremely little, so i returned the question what he'd be willing to offer, knowing that chances will be high that he lost that again. But i also added a suggestion to it, maybe if we'd change the 15 planned 'days we play' into whole weekends, from arriving after work on Fridays to leaving for work Monday morning without interruption.

He turned and looked at his boy bouncing there like nothing was happening at all, then thought a little and returned: 'I really am certain this time i get lucky, so i go all the way. I place the prior agreed 15 poker-night days in the bouncer, but i raise to permanent poker night weekends in the bouncer in the way you suggested against all your money winnings AND 100 poker night weekends in the bouncer for YOU, starting with the remaining time of this weekend for the looser.' He also added that we would sign a mutual promissory note in the amount of 500,000, payable immediately upon refusal to comply with the agreed weekend penalties, so the looser could not refuse for sure, no matter what.

I asked if he was serious, i looked at my hand again, no way I'd be loosing, so i mentioned whether he is sure, permanent, he'd never participate on our games but every time, so every other weekend, be over there like his boy was, asked again if he was truly sure about that. But he did not even listen, typed the promissory note already on his mobile and after pushing the print , i heard the printer already. He presented the doc for our singing. I again asked if he was certain, it was clear to me that he'd loose that one, but he countered with a 'chickening out, now that your stake raised too?' Well, that did it for me, i accepted the bet and stakes and signed right then.

I laid out the straight flush i had with a major grin on my face, but when he placed his hand on the table, fuck… double fuck…. mega fuck…. he also had a straight flush, but 9 to king. He yelped out, somehow only then realizing he actually won, at the same time i sat there, could not believe with that hand i lost this one…

But after grabbing the money on the table and the document we signed, he grinned at me, then pointed at his boy in the bouncer, telling me: 'The weekend still goes on for a while, time to get you ready.'

I still could not believe, but there was also no doubt about 'paying up' the losses, in all the years we played that was at no time ever a doubt.

We went into their bedroom, he had me strip and said: 'Exactly as my boy is the deal, that means double of the thickest night diapers we have, with double inlays to boost capacity, onesie and sicks only on top of that, the pacifier head harness locked on, mittens locked on behind the back, in the bouncer. but it also includes what you do not see, the flat chastity cage and the dildo up his butt.

I did not know indeed, but did not say much about it either, 'as his boy' was the agreement, not 'almost as his boy'. I was definitely not looking forward to any of it, so was not at all horny, it did not take any troubles for him to lock another flat chastity cage on me, making me think about the troubles to come when i DO get hard again, which i did regularly during evenings and nights. The bigger issue was the dildo then, i wasn't a virgin, but the amount of times and sizes of tools back there were limited in the past, so it took quite some work to accommodate the one he had, about 1.75 inch diameter and 7 inch long, with a base simulating a ball sack also.

Doing it all the time, the diapering up was no trouble for him at all, getting those two diapers and inlays in place neat and snug, by that also forcibly preventing that dildo from fully sliding out. But when i got up to get that onesie on, i noticed, sitting would push that thing deeper into my butt again, moving around meant slightly moving that thing in and out also, I'd be fucking myself slightly then, feeling totally weird to me right then.

But after onesie and socks were on, we went over to the living room, his boy still innocently bouncing around, unaware of anything. He unlocked the mittens of his boy and released him from the bouncer, then also unlocked and removed the head harness with the pacifier in place, while he then cleaned that dummy a little, he sent his boy 'to bed'. That harness went on my head, with it the huge dummy into my mouth, he even added the brim cap his boy wore earlier then before it was time to get into that bouncer.

I followed his guidance on that and minutes later was actually hanging in that thing, feet off the ground, my hands now also locked in those mittens on my back, and of course, with my weight on it, that dildo fully pushed up my butt now. He then took a little clip showing me off, all that was on, my helpless bouncing diapered, patting the thick padding in front of that flat cock cage also, not that i felt much of that anyway, then he said:

'It is Saturday morning 2 am now, so you have the time until Monday morning 6am, enough time to get ready to go to work then, I'll fetch the clothes you need to go to work from your place during the weekend.

I'll send this clip to our poker buddies, telling them that you won't be able to attend the next 100 game nights, because this is how you spend each of those weekends without exception.

So let it sink in during the remaining weekend now, I'll be snuggling up to my boy for the night.'

Olympic Judo participant Neil Adams is for some reason sent to the gunge tank wearing just his white speedos lol.  He gets two well deserved servings of gunge here.

Original video 

Why would he stop? He had you right where he wanted you: humiliated as you were made to watch in horror through the mirror while the behemoth of a man flossed your ass, your cock straining and leaking as the friction and pressure from your emarsssing undies increased. Or, rather, by your “tighty whities” as he called them - harkening back to your school days when the football jocks would give you the same treatment. Your mind began to wander, maybe you really did like this…

But your day dreaming was cut short as he spun you around and forced you on your knees. He pulled your head between his thighs, the smell of his post workout musk was almost too much to bear, although the relief from having your briefs rammed up your ass felt good while it lasted.

Unfortunately for your nerdy butt, the relief would be short lived. He bent over and you could feel his rough hands latching onto your waistband again. You were in a full on pile driver wedgie now. He pulled you off the ground, legs flailing in the air, as each yank of your briefs smooshed your face further and further into the bully’s sweaty crotch. It’s like he was marking his prey with his scent, your face will be smelling like his swollen nuts for a week. You didn’t have the luxury of worrying about that now though. All you could do was scream into him as he manhandled your undies. Your only hope now was for the briefs to rip completely, taking away the bully’s toy once and for all. Unfortunately for you, this guy was a wedgie giving pro, and he wasn’t going to let you off that easy.

He changed his grip from the waistband to the leg holes. “Sorry nerd, no pain, no gain” he said as he pulled with all his might. The sound of the seams from your tighty whities popping echoed in the empty locker room. The pain truly was next level, but your body was turning against you, as your cock continued to swell up from the situation. You could even feel the bully’s cock growing beneath his sweaty gym shorts. Was he enjoying this as much as you were?

Your daydreaming was cut short again as he switched his grip back to your waistband. With your undies stretched beyond recognition, they were already reaching the back of your head. There’s no way… He couldn’t… It’s not possible… but it seemed like he was trying to give you an atomic wedgie! That shit only happened in cartoons, or so you thought, until your bully heaved with all his might, successfully hooking your waistband over your forehead. He was laughing his ass off at this point, circling around you to admire his handywork. There you were, on all fours with your tighty whities yanked over your head. You didn’t dare move, not only out of fear of pissing your bully off, but because even the slightest movements resulted in the wedgie driving deeper between your butt cheeks. It can’t get more humiliating than this… But you were about to find out that it could, in fact, get worse.

Suddenly, you felt a cool breeze on your ass as your shorts were pulled down. There you were, in the middle of the locker room, fully atomic wedgied for anyone to see. The fact that anyone could walk in at any moment added to your humilaition, but it added to your excitement too. A stain was forming on the front of your briefs from all the precum you were leaking. This was the intended outcome of your bully, who now stood before you in all his muscley, sweaty glory, looking down on his little wedgie nerd with that smirk that drove you wild. “Seems like you’ve been enjoying yourself, huh dork? I think it’s time I get some enjoyment out of this too” he said with a wink. He lowered his shorts, revealing his own tighty whities underneath. “What a hypocrite!” was all you could think before he pulled his fully erect cock through the fly. You were drooling now. He had you right where he wanted you, and honestly, where you wanted to be too.

Without hesitating, you opened your mouth and got to work. You could hear him groaning from above, he began thrusting, holding onto the back of your head, worsening the atomic wedgie in the process. Eventually he changed his grip and grabbed onto the thin strand of cotton connecting your ass to your head. Back and forth, he bobbed your head on his cock, working it deeper into your throat, and your undies even further up your ass. This brute of a jock turned you into his wedgie boy flesh light, and you couldn’t get enough. The friction of the underwear rubbing against your hole and crushing your dick became too much, you couldn’t help it when your body gave in and released a pool of cum in the front of your briefs. You knew he could tell, too, since he chuckled as it happened. That’s when he grabbed both leg holes for the grand finale. Your underwear began making those popping and tearing sounds again as he pulled harder while fucking your throat. Finally, the underwear reached it’s breaking point, and he shot a warm load as he ripped your underwear completely off.

There you were, naked on your hands and knees, panting from what you’d just experienced. You looked up at your bully who was still towering over you, holding the shredded remains of your underwear up like a trophy. “Ha I knew you’d enjoy that dork. No denying it now that I’ve got your cum coated tighty whities as proof. You like getting fucked by your underwear, you’re so pathetic. I’ll be keeping these as a souvenir” he said as he walked past you, slapping your ass as he sauntered away, “hopefully I’ll see you again soon”, he said menacingly.

It was over as quickly as it started. He made his way out of the locker room and left you to collect yourself. Still processing everything, you pulled your shorts up, put your shirt on, and headed home. You were going commando at that point, another reminder of the intense wedgie blow job session. You managed to take a shower once you got home, the cool water feeling nice on your sore crotch and balls, although you couldn’t quite wash off the smell of his sweaty cock and balls from your face. After showering, you carefully put on another pair of briefs, or as he insisted, “tighty whities”, and laid on the bed. Looking back on how everything transpired, you couldn’t help but pitch another tent in your briefs, wondering what your bully was up to right now…