A rough sleepover

“Oh, I forgot to mention that Kristen, Kourtney, and Cayleigh are coming to stay over tonight.”

Tammy shouted it down the hall as if it was an afterthought to their conversation, as if the entire premise of having those girls in their home didn’t send a chill down his spine. Still, there was something to be said for his Mother bringing it up, at least they had plans together to keep them busy, rather than bugging him all night long.

“And be nice! Don’t ruin our fun, or you’ll regret it…”

Slightly puzzled by her foreboding words, he did his best to ignore things until it became too much to ignore, the first of the girls beginning to arrive.

Cayleigh was first, a rather short girl with long curly hair, strikingly blonde, and a personality to match. She’s the perfect picture of a ‘Hot Blonde’ stereotype, gifted in every physical asset, she was the fantasy of many men at this point. She often teased him about anything she could, not in the ‘I like him’ sort of way, but purely out of a desire to see him squirm under her gaze.

Kristen came next, arriving not long after Cayleigh. She had always been the ‘Mean Girl’ of the group, constantly looking for spiteful ways to hurt people, or to make curt comments to one another. Despite her foul personality, she had an amazing body, curves that you’d only find in a dream, and an ass that even a pornstar would be jealous of! It often made him confused about how aroused he got simply from being yelled at by her, but he’d learned to shrug it off by now.

Lastly was Kourtney, looking as if she brought the night with her, the usual gothic motif accompanying her even at a sleepover. She was certainly the ‘Hot Goth’ type, the kind you see exaggerated online, big breasts, thick thighs, and a plush set of lips that brough sex to the mind each time she spoke, no matter the subject.

With everyone there, Tammy quickly ushered them into the main room, handing out snacks, and even trying to get a few rounds of some board-games going. Though he soon learned that there were sinister plots at play, Kristen purposefully knocked the board every few minutes, then quickly looked annoyed at him in response, acting as if he had done it in the first place. After half of the game had passed, Tammy seemed as though she reached her limit with him, silently standing up before grabbing him by the ear and dragging him away.

Once out of earshot, Tammy whispers biting words toward him, giving him a stern warning.

“Don’t you dare ruin tonight for us! Stop acting up, or you’re going to have hell to pay, understand?!”

He could only meekly nod in response, shivering enough that his Mother had to grab him by the arm and drag him back to the table, sighing before jumping back into the game with everyone else.

Things continued without much of an event from there on, Kristen even inviting him over to play ‘Spin the Bottle’ with them! Things started rather tame at first, a few joking dares and truths taking place, a few flushed faces, and even some cop-outs of tough questions, but then a big one finally came.

“I dare you to give Tammy a wedgie!”

He instantly felt a cold feeling of dread wash over him, staring back at Kristen, he knew she was dead serious, and the punishment for refusing likely only getting worse. He didn’t have long, but he built up the courage to get up and move over to the kitchen, listening to her humming getting closer as he felt his hands shaking with a mix of anticipation and fear.

They didn’t even hesitate, Kourtney shouting out loudly for him to stop messing with them, Tammy turning around just as he grabbed the hem of her panties.

“He’s still fucking with us. This is getting annoying!”

That was the last straw, Tammy visibly breaking out of her fun demeanor and into something else, something cruel and uncaring.

With a faint terror glinting in his eyes, he was dragged off by Tammy, feeling his underwear ride up between his cheeks from being pulled across the ground. Still in his sights, he let out a defeated whimper as the girls each took their own enjoyment from the show playing out before them, shirking their punishments onto him as the cherry on top of their little sleepover.

“You’ve really pushed me tonight!”

Tammy’s stern words were practically spat down at him as she continued to drag him across the hall, ignoring his pained squeals while his underwear began tearing under the strain. When Tammy finally stepped through into her room, she reeled back and flung her arm, tossing him into the middle of the room, but also ripping his pants and underwear in the process. While he tried desperately to cling to the scattered cloth, he was effectively left on the floor, exposing his stiffening shaft to the group of girls and his own Mother!

“What the fuck… you really?...”

Tammy couldn’t hold in her instinctual disgust with what she was forced to witness, her own Son trying to pat-down his cock in front of her, smearing precum across his palms, a clear indicator of how aroused he had gotten from his torment.

“Just… Whatever, this punishment suits you even better now~!”

Kristen broke the silence everyone was stuck in, making them toss away any thoughts of mercy as they realized that he really did deserve what was coming to him. Still, not wanting to leave him naked in front of them, Tammy rummaged through one of her drawers for a moment, leaving the girls giggling to themselves as they pointed at him on the floor.

“I don’t think I’ve ever actually laughed at one before~”

Cayleigh let her feelings come out clearly, causing Kourtney to laugh, joining in on the fun, despite her hesitance.

“You know he’s probably tugged it thinking about us, right?”

The other girls gasped in disgust, glaring down at him still trying to cover his crotch. Kristen took a step forward, a faint fury in her eyes, but was pushed out of the way by Tammy, who had returned with what she was after.

“Right! Time to get you sorted.”

Without awaiting his response, Tammy leaned down closer to him, uncomfortably close to his cock, her breath even brushing up against his tip as she breathed down on him, sending shivers down his body. While lost in the subtle stimulation, he barely noticed Tammy shimmying what she had brought up his legs, a gray pair of briefs that clung tightly to his body. His resistance was much too late, only letting out a single kick of his legs before Tammy let go of the hem, allowing it to snap against his skin, eliciting a yelp from his lips. The girls looked down at the faint bulge, Tammy trying to encourage them to compose themselves, but failing to hold in her laugh all the same.

“Alright, come on then. Help me lift the little perv up!”

Tammy snapped her fingers, pointing down at him as a signal for the girls to each take a side, following Tammy’s lead as she gripped the hem of his new underwear and yanked him to his feet. A shrill squeal escaped his lips as he found himself dangling in the air, hanging as if in a harness, his balls squished up against his crotch, and his dick being forcibly rubbed against the front of the underwear as he bounced.

He was too lost in the baffling scenario to properly understand what was going on, only until he felt himself lifted higher into the air, then suddenly dropped, did it finally click. Initially it was the fiery pain of dropping into his new wedgie, squealing out as precum soaked the front of his briefs and his legs frantically kicked around for some kind of support to escape with. Only to his dismay, there was nothing, only the realization that this was his punishment, a pair of wedgie-underwear and a hook to hold him up with.

“He looks so much better this way~!”

Kristen certainly wasn’t afraid of speaking her mind, especially now that he was effectively locked away for the night. The girls worked together in restraining his arms behind his back, tying them securely with rope that was hidden away in the closet.

“Damn right! But it feels like he’s missing something…”

Pondering for a moment, Kourtney bites her lower lip, smearing the black lipstick before her eyes light up with an idea. Practically skipping away, it’s not more than a few moments before she returns, an unfamiliar pink object in her palm.

“This will make it more of a punishment, don’t you think?”

The girls leaned in to see what her idea was, each of them breaking into a sadistic smile after seeing it. Tammy came to see as well, smirking with the others, but taking it from Kourtney, opting to do it herself as she came closer.

“W-wait, I’m sorry! Whatever it is, please don’t!!”

His desperate pleas for mercy fell on deaf ears, if anything, it only encouraged Tammy to continue with their plans, taking a short piece of tape and rubbing it against the front of the underwear, right on the tip of his cock. For a moment, he was somewhat lost in thought, wondering what was to come next, but a painful and humiliating answer soon rushed across his body. Whatever it was that Tammy taped to his crotch suddenly sprung to life, buzzing against the tip of his dick and stimulating him in a way that he hadn’t felt before. He couldn’t help from bucking his hips forward in response, helplessly trying to grind against it, only achieving his wedgie digging deeper between his cheeks in response.

“Ew! Close the door, close the door!”

Cayleigh made it a point to shout out in disgust over what they were witnessing, the pathetic throes of passion of a wedgie-loving guy with a bullet-vibe taped to his cock. Tammy was all-too pleased to oblige however, giving a mocking smile as she flicked the door closed, the light disappearing from his view too quickly to allow panic to set in. Before he knew it, darkness had settled in, the prying eyes had disappeared and the giggling slowly faded beyond the door, signaling how the girls had left him there to suffer.

Downstairs, the girls began diving into the supplies for the sleepover, several packets of sweet treats, and Kristen was even preparing a bowl of popcorn for everyone! Within minutes, they were all sat down on the sofa, kicking back to enjoy a little movie-night with one another. Only a few side-comments of his suffering were mentioned, the rest being ignored to the point that they likely forgot he was there, until Kourtney paused the video suddenly, straining her ears to listen.

During all of this, he was still struggling upstairs, the vibrations becoming too much, as each time he attempted to gain any additional pleasure from it, he only suffered at the hands of his wedgie even more. It squeezed his balls and brought a searing pain between his cheeks as he flailed helplessly in the air. Before he could stop himself, the sudden rush of arousal he felt reached its peak.

He tensed up in the air, thrusting forward one final time, accepting defeat at the hands of the tiny bullet-vibe stimulating the head of his dick. The blissful and shame-filled cries of a broken man echoed out of the closet and down the halls, annoying the girls as it interrupted their movie night. Resentment building, they each made their way back up, not thinking about what they would see until Tammy flung the door back open, exposing him as he still leaked a thick load of cum through his underwear and onto the closet floor.

“Fucking ew! Put him back away, that’s fucking disgusting!”

Not pleased with the sight, Kristen covered her mouth and turned away, leaving it to the others to sort their little ‘issue’ out. There’s a silence for a while, each of them simply savoring the sight of him dangling in front of them, but Tammy breaks it with an idea.

“Come on girls, let’s shut him up, shall we~?”

Without explaining how, Tammy closed the door to the closet, leaving him, quite literally, in the dark about what he was going to be subjected to. After a few moments of giggling, the door flung open again, only he was quickly assaulted by a flurry of hands shoving something into his face. Tammy pushed past to force his lips open, giving way to an assortment of panties being shoved into his mouth, right before Tammy wrapped his mouth in tape to keep them secured.

“So much better! Let’s go finish our movie~”

Before leaving, each of the girls loudly stuck one of their fingers into their mouths, sliding their tongues across it and lapping their spit as much as they could. Then, without warning, they forced their fingers into his ears, one-by-one they gave him a dreadfully soaked wet-willy, giggling as they ran off, leaving him with the cold and slimy sensation trickling inside of his ears.

With their solution finished, he was left alone once again, treated like nothing more than a problem as he came, once again the light was taken from him and solitude overtook the closet. Minutes bled into hours, the boredom only broken up by the occasional orgasm wracking his mind, forcing involuntary jitters from his body, despite the agony it brought from bouncing in his wedgie prison.

Soon, the day came, light bleeding through the cracks in the door, he simply hung there, waiting for the girls to take pity and let him down. His eyes were lazily staying open, making him look like a wedgied-zombie at this point, but thankfully they came, the familiar sound of giggling coming closer as he perked up slightly.

“I bet it snapped and he’s on the floor!”

Their teasing had already started before they even opened the door, but all the same, the welcome feeling of the sun against his skin calmed any frustrations he had, but the girls weren’t not feeling the same.

“What the fuck did he do?!”

Completely lost for words, the group of girls simply stared at what a mess he had made, their faces twisted in abject disgust. Looking down, he realized why…

In the moment, it didn’t seem like so much, or even that often, but he could clearly see an incredibly thick puddle of cum pooling beneath him, a thin strand of his previous load still dripping from his tip and down into the puddle. Tammy was the only one that found amusement in his predicament, gleefully smiling as he twirled around in his wedgie, the faint buzzing still audible after all these hours. With more plans still in mind for him, Tammy decided to give him some mercy after all, reaching out with a pair of scissors, she cut the strained fabric, letting him plummet to the ground.

“Holy fuck you’re a psycho! Fucking bitch!”

As he slapped against the floor, his face smeared into his puddle of cum, flinging several strands into the air, Kourtney getting the brunt by the sounds of her insults.

“Oh grow up! Just find something to wipe yourself down with, we’ve still got to clean him up~”

The prospect only sent a shiver of dread down his body, looking up through his sticky mess, he saw their mischievous grins trying to decide what to do next with their little pervert. Snapping her fingers, Tammy manages to come up with an idea, flicking her head over to the hallway, the girls lead on ahead, leaving Tammy to grab their toy by the tattered hem of his underwear, tearing off the tape and pulling the panties out of his mouth before dragging his cum-stained body down the hall after them.

It didn’t take long before he found himself tossed down to the floor again, only this one was cold and hard, rather than soft. Looking around, he saw the upstairs bathroom around him, hoping they were going to simply wash him down and be done with it, but one look at Tammy’s evil smile melted that hope away.

“You’re awfully dirty~”

He didn’t even have to turn around to know that the other girls were encroaching upon him, instead doing his best to ignore his impending fate, staring at Tammy as she spoke.

“Let’s flush away your filth~”

As she finished, the girls grabbed hold of his body, pushing him closer to the toilet, forcing him to look down into the crystal-clear bowl. After a brief pause, Tammy joined them, taking hold of his head before clutching his hair tightly, forcing his face into the cold waters.

“Flush him.”

Her cold tone only made the sudden rush of water sting more, Kristen doing the honors of twisting the handle, watching and listening to his suffering. Between each flush, Tammy pulled him out of the bowl, examining his face, but tutting to herself each time, clearly displeased. Time after time he found his face shoved into the cold water, feeling the swirling rush as it felt like they were trying to flush him at times. He gasped for air and squirmed in her grasp, eventually giving up, her iron-grip too strong to resist, he simply accepted his place as their plaything.

Pulling him up again from the water, Tammy examined him once again, only this time she smiled to herself, lifting his chin to examine him closer.

“Much better~”

After a brief hope of his ordeal being over, he was given a stern reminder of how sadistically cruel these women could be as he felt a painful flick against his still-hard cock.

“Though I think he still has a few lessons to learn in that closet. Maybe we should come and get him out later tonight~?”

The other girls agreed readily, each helping as they dragged him back to the closet, picking out a new pair of underwear before starting the entire process over again, listening to his squeals all throughout the day, savoring every moment of his suffering as he slowly broke to their will.