Chapter 6: Reunion Revenge
Upon arriving to the guild house the next day he couldn’t help but wonder what plans lie ahead for him, what news could Eugene possibly have, as he parked in his usual spot, stepping out of his convertible Cupcake nervously sighed and grabbed his bag of slutty sissy gear and headed into the Guild house.
Entering the Guild House, Cupcake could hear the sounds of laughter coming from the basement, where the nerds usually gathered for their weekly meetings. His stomach churned with anxiety as he walked towards the noise, his feet dragging slowly across the cold floor.
“Hey!!! There’s our favorite bimboi slut!” Simon shouts, Cupcake instantly noticing the nerds are all dressed up as if they’re going out somewhere for once.
As they’re all smiling awaiting for Cupcake to hear Eugene’s plan,
the sissy feels a mixture of fear and excitement, wondering what the guild has planned for him tonight. “Alright sissy,” Eugene says, his voice carrying a hint of amusement, “you do know what today is right?” They’re all looking at the confused bimbo as Cupcake searches his mind for any major holidays or events he might’ve forgotten about…Oh god, he thought, he’d just glanced over the reunion invite a few weeks ago, but the course of his life changing unexpectedly at the hands of the nerds he’d completely forgotten.
“No…no no no no way!” The sissy stammers as the nerds all realize he knows exactly what Eugene is talking about
“Of course we wouldn’t miss this opportunity,” Simon remarks, his face breaking into a malicious grin. “Well, what’s our little bimboi gotten himself into?” Dexter adds, looking at Cupcake with an air of amusement.
This was payback time. They all chuckled, smirked, and leered at Cupcake, who looked like a deer caught in headlights.
"It's payback time, sissy!" Simon declared, slapping Cupcake hard on the ass, leaving a bright red mark. "We're going to give you a special treat tonight, little slut." Dexter added, a sinister smile crossing his face.
As Cupcake stood there, struggling to maintain his composure, he could sense the anticipation rising among the nerds.
Simon breaking in “so we’ve got a list of all the people you were an absolute asshole to, and we’ve decided, if you don’t want to be exposed there in public amongst all our peers, you’re going to have to, hmmm, make it up to them, however you deem necessary.”
“And we will be keeping tabs sissy!” Doris chimes in.
The sissy completely overwhelmed by the need “what…who, how many guys?!? No there’s no way, people will know!?”
“According to my calculations from an “anonymous” poll I programmed on our class site, you only have about 10 that will be in attendance tonight.”
As this is going on Doris seats Cupcake into a chair as she begins doing the bimboi’s makeup for the night. “Don’t worry sissy, you’ll be completely unrecognizable, unless of course you fail completely in which case, everyone will know so it won’t matter!” She smiles coyly as Eugene returns with a sequenced red dress, backless and tiny, gauging the sissy’s reaction to their choice of her attire, along with a full lingerie set to match, the black crotchless pantyhose, the seemingly see-through red thong, if you could call it a thong, the material in hand so small it won’t provide much in the way of hiding sissy arousal.
Cupcake unable to even raise an argument resigns to his fate as he is being dolled up.
like a porn star, with false eyelashes and a heavy coat of makeup, his platinum blonde wig fitting perfectly onto his head, adding to the bimbo appearance.
Doris then turned Cupcake's head toward the mirror, showing off his new outfit. "You look absolutely stunning, sissy," she said, complimenting his makeover. As Cupcake stared at his reflection, his cocklet twitched with fascination. “Oh and so nobody questions your appearance” Dexter steps to the bimboi and spreads a familiar purple slimey lotion to the sissy’s chest. Gasping Cupcake knew exactly what was about to happen as his chest began to tingle, expanding outwards as the sissy moaned, his now breast inflating inside the too tight form fitting dress.
“Damn sissy, if we didn’t have to head out you’d be absolutely fucked right here!” Simon laughs lustfully taking in the sight.
"Well, well, well, it seems our dear sissy isn't able to hold it in for long." Cupcake, ashamed and sweaty, can barely keep his hands from reaching down to adjust his dripping cocklet. The nerds all surround him, leering and snickering. Dexter comments, "We're going to have so much fun watching you get all the cock you can handle tonight, sweetheart."
Cupcake, desperate to regain some control, tries
to speak, "Look, just tell me how many of those people are going to be there..."
Eugene interrupts him, saying "Just shut up and let us handle it, you're getting a taste of your own medicine now."
Feeling utterly defeated, Cupcake accepts his fate and lets the nerds take charge as they walk to the car and head the the Hotel for the reunion.
As they arrived Eugene turned to Cupcake grinning, “oh and one more thing I’d almost forgotten,” the nerd pulls Cupcake’s butt plugged from his pocket smiling at the sissy, “don’t worry, I put fresh batteries in last night.” Sighing the sissy leaned over Eugene so that he could slip the remote operated plug into his tight hungry hole, Eugene giving the sissy a playful ass smack signaling he was done as the bimboi tried to hide a gasp. Stepping out of the car, wobbling on his 6 inch fuck me heels, Cupcake joined the guild as they all walked toward the front doors. “Cupcake if anyone asks, you’re my date,” Eugene laughs taking the sissy by the arm, “escorting” him.
As they walk into the grand hotel lobby, Cupcake’s breath catches in his throat. This was exactly the kind of place he had hoped to avoid, filled with the very people he had wronged in high school. He felt the panic rising within him as he realized he would be exposed, that his humiliation would be complete.
Doris walks up beside Cupcake, whispering softly in his ear, “You know, you don’t have to worry about anything. Nobody is going to know a thing, unless of course you fail your “tasks”, she playfully pinches the sissy’s bubble butt,
Just relax and enjoy yourself. Don’t forget why you’re here. You owe these people a chance to get back at you.” Eugene smirks, putting an arm around Cupcake’s shoulder, trying to calm him down. But deep down, Cupcake felt his heart racing, dread filling him as he entered the grand ballroom.
Inside, Cupcake could feel the eyes of everyone present, watching his every move.
I was evident he was getting everything he’d previously wanted, to be the center of attention, yet this is not what he was expecting. As a few members of the guild spread out greeting their friends, Cupcake got put to work, as Dexter pointed out the first name on his list, “here sissy, there’s a guy you might remember over in the corner, better start checking names off the list, clock’s ticking!” He hands Cupcake a marker, “have them sign your sexy fat ass when you’re done so we know you aren’t cheating.”
With a trembling hand, Cupcake takes the marker from Eugene, his palms sweaty with fear and arousal. He walks over to the first person on his list, hesitantly approaching him.
Cupcake’s nervousness was evident as he approached the man, the sweat trickling down his forehead. The dweeb seeing a buxom bimbo headed his way, face flushed staring at him eagerly, shuffles in his seat, as he’s surprised to see such a sexy beauty heading directly for him.
The nerds watch on smiling as they see Cupcake whispering to him, the man’s eyes go large and he smiles big as he downs the rest of his drink he hurriedly grabs Cupcake by the hand and leads him to a nearby janitors closet.
As they enter the room Cupcake’s heart races, he can hear his pulse in his ears. The door clicks shut behind them, plunging the room into darkness. Cupcake feels his body quivering, his balls aching with desire. Suddenly the plug jumps on vibrating at different sequences, making Cupcake’s flash turn bright red.
The man presses into Cupcake, squeezing into the small closet, his body against Cupcake’s tightly packed form. His hand travels down Cupcake’s thigh, feeling the delicate fabric of his dress. Cupcake acts before the dweeb finds his bulging thong, sliding to his knees, ass pressed against the wall, his face close the the loser’s crotch working with what little room there is in the closet.
The sissy, eager to get out of this situation relatively quickly starts rubbing the erect cock through the guy’s pants, thinking a handjob will be suffice to get the loser off quick enough, not like he’s getting any from anybody else, Ugh I mean look at him, the bimboi thinks to himself.
As the guy unzips his fly and pulls out his thick cock, Cupcake looks at the impressive length, swallowing hard. Jesus do all nerds pack so much meat, he thinks as he glides his manicured fingers over the warm thick shaft, cupping and teasing the balls with the other, “we have to be fast!” Cupcake whispers as the dweeb just shakes his head, doing whatever the buxom bimboi says as his hips start to thrust as Cupcake’s gripping hand.
Not three minutes later, the guild all having gotten drinks from the bar and talking amongst themselves at a table they’ve picked out, they see the closet door open, and Cupcake fixing the back of his tight form fitting dress, as the sissy stumbles out of the closet followed by a grinning dork, Simon waives to the sissy. Embarrassed Cupcake passes by all the tables with his friends at them making sure to look away as he passes as to not be noticed making his way to the nerds.
As he arrives they notice the cum dangling from the side of his shoulder length wig, scoffing, and laughing they don’t even tell the oblivious bimboi who is filled with arousal and shame. “You get the signature slut?” Doris asks, to Cupcake who just silently nods yes. “Good work sissy, one down, nine to go!” The smiling Simon remarks as he gives a thumbs up back to the dweeb who’d just emerged from the closet with their sissy.
Sighing Cupcake resigned his fate, asking for the next name on the list, thinking he can accomplish them all in just around an hour if they’re all quick and easy handjobs like the first one.
The nerds clap excitedly, egging him on, “Come on sissy, you know the alternative is everyone here watching a slideshow of your escapades with us, now get to it!” Doris almost can’t help from laughing as Dexter points out the next names on the list. Cupcake grabs Simon’s drink and guzzles down the strong alcohol as he tries to use liquid courage to not be so embarrassed.
As the Guild are reminiscing their school days with multiple different friends after about a half an hour they see their bimboi making his way back to them, obvious cum stains on the front of his dress from the deposits of the previous two guys.
“Nice work slut, seven more to go” the group replies all in smiles as they’re actually enjoying not only their evening but also their revenge. Cupcake gets the next name and groans, downing another drink, walking off, fat ass and tits jiggling in the tight now unkempt dress, as they see Cupcake whispering into one of their old friends ears.
The guy smiles and follows Cupcake back through the hotel kitchen past the staff only sign.
He’s clearly unaware that he's breaking the rules as he blindly follows the sexy bimbo, Cupcake thinking, “Oh God, please let this be quick!”
Entering the nearest walk in fridge, the guy pushes Cupcake against the wall, and Cupcake responds by pulling the nerd’s cock out from his pants.
“Suck my cock you horny little slut!” The loser demands, startling Cupcake and and instantly triggering all of his submissive signals
, without even a moment's hesitation, Cupcake slips down onto his knees, his own cock barely able to fit through the tight thong. Taking hold of the nerd's cock, Cupcake begins to expertly stroke it with his mouth, tongue flicking along the underside, skillfully sucking and licking while massaging the shaft with his hand. Meanwhile, the loser's hands clench the countertop, holding onto it for support as he struggles to maintain control over his urges.
Feeling the heat from Cupcake's mouth and the vibration of his lips as they rhythmically dance across his erection, he moans loudly, unable to believe how good it feels. In as much time as they began the guy was already depositing his loser seed into Cupcake’s throat. Omg he came so quick, maybe blowjobs will be faster?! The sissy thinks to himself as he’d barely even gotten to suck on the swollen member. “Fuck, you’re way too good at that baby,” he remarks, “hit me up later for round 2!” Smiling he goes to leave zipping his pants.
“Wait!” The sissy replies, “I uhmm, need you to do something for me?” Handing him the marker, lifting his skirt and bending over, the guy notices the names on the fat sexy ass, and then he notices the hot pink butt plug buzzing away, laughing he gets the picture and signs away, adding “Suck Queen” beside his signature.
Cupcake's heart skips a beat as he stands up, a mix of embarrassment and excitement coursing through him. He smiles and thanks the guy, but inside, he feels a newfound sluttiness thinking blowjobs will make this way faster.
The thought of performing oral sex on these nerds sends a thrill through him, making his crotch tingle with anticipation. The jolting plug going up in speed snaps him out of it, next on the list James Griffen, the chubby former band geek didn’t stand a chance. With smeared lipstick Cupcake whispers to James, as the guy who just followed Cupcake out spots him, he begins to wonder about how many signatures the slut will end up with tonight, and soon, whisper and word gets out about the buxom blonde bimbo giving blowjobs in the back.
James, still a bit perplexed by the whole situation but curious to see what this strange encounter might lead to, agrees to meet Cupcake back in the room he had checked into earlier that day, not passing up a chance to get lucky, he stands not even hesitating, as to his surprise the sexy slut finishes off his drink as she takes him by the hand.
Cupcake is relieved to find some privacy once again, risking being walked in on by hotel staff or being stuffed in a small closet, while exciting was equally degrading.
As the door closes to the room, James is already out of his pants, “let me see those giant tits baby!” He winks at the sissy, as Cupcake, rolling his eyes, slips the tight dress down over his expanded breasts, James doesn’t hesitate and begins to masses the massive mammaries in front of him, surprisingly to Cupcake eliciting a moan from his lips, not realizing how sensitive they were.
James, emboldened by his success, pushes Cupcake down onto the bed, positioning himself above the busty beauty. As he leans down to take one of Cupcake's enormous breasts into his mouth, Cupcake's long blonde hair whips against his face, adding to the eroticism of the moment. Cupcake, taking advantage of the distraction, reaches for James's briefs, yanking them down swiftly, releasing his large cock. Simultaneously trying to hide his own upright erection in his dress,
Unable to contain his excitement, James plunges his face into Cupcake's cleavage, desperately trying to consume the delicious flesh that was offered to him. Cupcake, feeling a surge of power and dominance, gently presses James's head deeper into her chest, enjoying the sensation of his lips and tongue caressing her soft skin. Slowly, he eases his way towards Cupcake's erect nipples, licking and sucking them gently.
Realizing what’s to come Cupcake squeezes his tits together, inviting James to fuck them,
James gleefully obliges, rubbing his engorged cock against Cupcake's jiggling tits before slowly penetrating the bimboi’s cleavage. The sissy gasps in pleasure, feeling used, and dirty, but also incredibly turned on. As James thrusts, Cupcake writhes beneath him, moaning in ecstasy, his own cock pulsing and aching within the confines of his dress.
Groaning, James picks up the pace, moving like a jackhammer.
James in complete heaven fucking a huge pair of knockers, eyes closed, as Cupcake signs rolling his eyes wondering when the eventual flood of cum is coming, degraded looking up at the band geek jumping at his tits, can’t help but focus on his buzzing ass and straining cocklet as his body is being used, realizing tonight he’s been nothing more than a pleasure doll.
With a sudden surge of desire, James lets out a cry of release, filling Cupcake's breasts with his warm semen. The sensation is intense, shooting electricity through Cupcake's body, making him tremble with excitement. The cum squirts through landing on the surprised sissy’s lips and chin.
Feeling the powerful orgasm ripple through him, Cupcake finds himself helplessly lost in the act of giving pleasure, submitting completely to the role of a sexual object.
As James continues to thrust into Cupcake's heaving bosom, the young man cannot help but feel a sense of pride in his ability to bring this nerd to such heights of ecstasy. Despite the degradation, there's an undeniable thrill in knowing that he has the power to make someone lose themselves in the passion of the moment.
Cupcake looks down at his breasts, stained with James's semen, and allows himself a moment of self-indulgence.
His gaze lingers on the milky residue that adorns his chest, a testament to his ability to bring satisfaction to others. Feeling an odd mix of shame and pride, he takes a deep breath, preparing himself for the rest of the evening.
As Cupcake goes to the bathroom, hiding his tented dress with his hand, he returns, make up freshened, most of the cum from the night cleaned up atleast, and asks James for signature, as he’s now redressed ready to return to the event.
James, satisfied yet wanting more, scribbles his name, signing as "James Griffen" on Cupcake's ass.
He couldn't resist leaving his mark on the bimbo's perfectly rounded cheeks. As Cupcake turns around, the naughty inscription visible, shimming the dress back down over his thong clad ass, James goes to ask about the others but decides against it as the sissy hurriedly heads out the door.
Returning to the smiling, relaxed guild table, Cupcake hiding the unmistakeable tent in his dress as best he can with his clutch purse, as Dexter informs him only four more to go, giving him the next set of names, lucky for Cupcake they’re both seated at the same table. “Two for one of you play your cards right slut!” Doris mocks, as Cupcake agains takes Simon’s drink and downs it, strutting to the table abuzz from the nights events, the alcohol, the plug, all of it.
A giggly conversation later and the guild watch and laugh as the sissy is leading the two guys to the restroom, no doubt to occupy a stall.
As Cupcake knelt on the marble bathroom floor, between two guys whom he used to call “small cocked virgins” the two dweebs on either side of him were watching the slut work both of their cocks at once, one in each hand, this sissy in a hurry to get these names checked off began sucking on the heads of their superior cocks, alternating one to the other.
The two nerds couldn’t believe what was happening to them as the pretty girl with the big fake boobs leaned forward to take each of their cocks into her mouth, the two watching in amazement, Cupcake working hard to get this done as efficiently as possible, the two onlookers could hardly believe their good fortune.
Their eyes glazed over as Cupcake moved from one to another, occasionally glancing up to see if anyone else was in the bathroom.
The two men found themselves hypnotized by the sight of Cupcake's lips wrapped around their respective members, expertly sucking and stroking them in perfect synchronization. They couldn't believe this was actually happening, but who were they to question getting to blowbang this sexy slut in an undersized dress slobbering down the length of their shafts asking if they were ready to cum.
As Cupcake continued to take care of their needs, the two men felt their arousal building rapidly. Unable to contain their excitement any longer, one of them finally broke the silence, stammering, "I...” that’s the only warning Cupcake got as one of them erupted onto the side of his face, while the other watching the cum splash against the bimbo’s face came into her mouth.
The liquid gushed into her throat as Cupcake swallowed without pause, greedily devouring every last drop. Cupcake wondered why he swallowed by time was of the essence, he couldn’t dwell on why he did it.
Despite the mess on his face and lips, Cupcake stood, lifting his dress, exposing his thonged ass to the two, holding the sharpie over his shoulder, they easily put 2 and 2 together, sharing a laugh about the names on the list, even going as far as saying “ewww a what a loser!” About a few of the names they read. Cupcake awaited the signatures on his plump ass as the two mocked what a slut he has been.
The laughter died down as Cupcake bent over, presenting his round, firm cheeks for the signatures. Each of the two nerds, eyes glinting with amusement, signed their names on Cupcake's ass.
As Cupcake stood up straight, brushing imaginary dust off his costume, he couldn't help but feel ashamed and extremely aroused as the double bj he’d just given,
He looked down at his torn and soiled dress, the evidence of his night of servitude still clinging to his skin and dress…”just two more” sighed the sissy, humbled by the nights events already.
Reaching the table, Simon already handing the sissy his drink this time, as he drinks it, Cupcake waists no time getting the next name and strutting off, The guild in disbelief that the slut has actually made it this far.
As Cupcake does the usual whispering in the ear, making sure his pert tits are on display he’s soon followed by the next to last suitor. This time it’s Danny Conners, a complete reject in Cupcake’s eyes, but here he was leading Danny back to the elevator after Danny mentioned his room. Only thing is Cupcake was unaware word had gotten out about his evenings antics, and James wanted more than just a blowjob or a titfuck.
Cupcake figured why not get him on edge early and slid his hand down Danny’s pants in the elevator. “Ohhh eager aren’t you sweetie?” Cupcake in no mood for small talk just fake smiled and began massaging Danny’s semi hard shaft as Danny squeeze and groped the sissy’s ass.
A surprise to them both as the elevator halted and the doors slid open to an elderly couple, eyes glued to the bimbo with a disheveled dress cranking away at a dork’s penis in the elevator. “Filthy slut!” The elderly woman said, “we’ll take the next one you disgusting perverts!”
Ashamed and embarrassed Cupcake withdrawing his hand as Danny laughed, knowing they were right. Arriving at the correct floor and getting to the room, Cupcake didn’t even bother with requests, just eased his jiggling tits out, getting on his knees and awaiting Danny’s cock for a quick blowjob.
Danny smiled and obliged, but he had plans, he needed to fuck something or someone, and the perfect bimbo was right in front of him slurping on his now hard cock. He needed to know if the rumors were true, if the slut in the red dress was getting as much cock as she could tonight.
After a few minutes, only slurping and sucking noises filling the room, Danny pulls away from Cupcake’s puffy lipstick ruined mouth, telling the sissy he wants to fuck.
Maybe it was all the drinks, maybe it was all the cock, but Cupcake not wanting Danny to see his cocklet all too eagerly said “My ass!” To Danny’s surprise, he was all to keen to ass fuck a bimbo, the sissy slut crawled up on the bed removing the still vibing plug from his ass, to more of Danny’s surprise, and hiked his dress up over his waist. Tossing Danny a condom from his purse quick succession.
With his condomed cock Danny gripped the sissy’s voluptuous ass cheeks, kneading them like dough while teasing the hungry hole in front of him, gliding the length of his dick against the sissy’s sensitive slut hole getting moans from the bimbo.
Danny grinned with a bit of cruelty and asked, “You like that don’t you slut? You want me to fuck you?” He whispered.
As Danny drove into Cupcake’s tight little hole, Cupcake groaned out loud, feeling his prostate tickled and a surge of pleasure running through his body. ”Cum inside me,, I need you to cum” Cupcake begged, feeling his own orgasm coming near. Danny grunted, the feeling of Cupcake’s warm walls gripping his cock bringing him closer to release.
Slowly, the rhythm picked up as the two bodies moved together, the sounds of Cupcake’s cries of pleasure echoing throughout the room.
Danny's thrusts became faster, harder, pushing Cupcake closer to the edge, the sissy's moans growing louder.
"Yes, yes, cum inside me," Cupcake begged, the desperation in his voice undeniable. It wasn't just about fulfilling his duty; there was something deeper, more primal within him that craved this release. His arousal was becoming almost unbearable, but as Danny pulled out and aimed his cock, Cupcake's mind was filled with disappointment that he couldn’t get off to the short fuck session. As Danny’s spunk splashed against his lower back and ass, the asshole removed the condom before erupting, Cupcake was atleast satisfied that there would be only one more to go.
Ever ready, as Danny still stroking his spent member admiring the bimbo on all fours in front of him, and the amount of cum covering her delicious ass, Cupcake handed him the marker, seeing the names as Cupcake stands upright, making sure to cover his straining tent in his dress. “Hmmm, I’ll sign on one condition,” The loser grins eyeing the bimbo’s signed ass, “I want your panties as a souvenir, only fair since I left you with my own,” he gestures as the oozing cum on the sissy’s butt.
Remember why he was such a dick to Danny, Cupcake slid the well precummed thong off, handing it over by a finger to the dork, without thinking it was doing the most in hiding his arousal he needed that signature.
As he annoyingly left the room, this time without freshening up, eager to check off the last name, the wetness on the dresses ass and back showing through and clinging riding up higher with each high heeled stride, hair a mess, doing his best to reapply lipstick Cupcake realized he twitching cocklet was super obvious now, the contrasting shadows in the dresses fabric did him no favors and now without the thong to strain against he was basically advertising his crossdressing to everyone.
He thought, “Fuck it, might as well get it over with.” Making his way back to the main hall, Cupcake nervously did his best to hide his cocklet. Feeling increasingly exposed in his disarrayed state, Cupcake approached Dexter and leaned in to got the final name. The guild all spread out amongst the bustling convention floor as Cupcake ignored nearly everything going on around him, set of finishing off this list, and possibly getting an orgasm out of it, win win he guesses.
Drunk now the sissy almost spit out his drink, “Gerald Marks?!” He squeaked to Dexter as the nerd looked up smiling. Gerald, or “skid marks” as Cupcake and his crew used to refer to him was the epitome of geeky loser, the overweight dork was also constantly checking out Cupcake’s girlfriend back then, making the then bully humiliate the geek even more.
“Oh god do I have to?!” Cupcake whined your Dexter, “please, why don’t you just take his place on the list, just anyone else please?!” Dexter laughed, “I can fuck your sissy brains out whenever I want slut, he’s the last name, rules are the rules!”
Cupcake annoyed and humiliated already looks around the room, spotting the red cheeked Gerald talking with Doris and Eugene…”damn them” Cupcake thought as he built up his courage for the final name of the night, as he approached Eugene said “ohh there you are toots!” Waiving Cupcake over to the group, introducing him to Gerald.
Gerald immediately locking onto the bouncing tits as Cupcake made pleasantries, “I’ll see you in a bit sweet cheeks, I got to make my rounds.” Eugene smiles and winks at the sissy as he’s now left alone with Gerald, needing to not only cum, but to cross of the last name, Cupcake finally asks the hefty dork if he’d like to go somewhere private.
Gerald’s eyes light up as he replies, “Oh yes, lead the way, sweetheart!” Gerald’s voice booming booming through the crowd as former classmates turn to see the sissy lead the loser by the hand, Gerald’s body odor becoming obvious to Cupcake as he tried not to groan in disbelief that this was about to happen. All the normal spots wouldn’t work, this time, and Gerald wasn’t renting a room for the night, Cupcake beginning to wonder how this was going to go down he spots the dark area under behind the stage, as the two awkwardly make their way into the shadowed curtains and find a few pieces of spare furniture, one being a small couch, that the hotel had stored for extra space.
The large loser plops down onto the small couch, hearing it creak beneath him, as he still hasn’t taken on the sissy’s jiggling assets, eager to see what’s in store, of course the entire evening each of the guys have been in on it, but they’ve done a better acting job than Cupcake not letting him have any idea. Gerald eager to not only fuck something, but a smoking hot bimboi, what more could he ask for. With Cupcake already dying for an orgasm this was a recipe for comeuppance.
Slipping off his heels, he kneeled on the hardwood floor in front of Gerald, looking up at the larger man who couldn't wait to get his hands on the sexy bimbo. The smell of Gerald's sweat mixed with his anxiety clouded Cupcake's nose, but he pushed forward, trying to ignore it all for the sake of getting this encounter over with.
As Cupcake began to undo Gerald's belt buckle, his heart raced with both anticipation and dread. This was it, the end of a long, emotionally draining night - the moment of truth when he would finally cum after so much teasing and pleasuring others. Cupcake swallowed hard, his throat dry from nerves and suppressed desire.
As Cupcake started sucking on Gerald's rock-hard cock, he felt a mix of emotions — he hated that he was actually enjoying this moment despite the situation.
Gerald moaned deeply, his thick fingers tangling in Cupcake's cum stuck hair as he pumped his hips.
The sound of Cupcake's sloppy sucking mixed with Gerald's labored breathing created a symphony of lust.
In this moment, Cupcake's mind was a whirlwind of conflicting emotions. He didn’t want to be fucked, he needed to be fucked.
Gerald tore at the sissy’s dress groping at Cupcake’s perfect pair of tits as he enjoyed the slutty performance.
Needing his orgasm Cupcake stands up, shoved Gerald back agains the couch hikes his dress and mounts the fat loser, his back now to Gerald who is reaching around still playing with the sissy’s sensitive tits. Greedily getting handfuls, “I need to be fucked Gerald, hard!” Cupcake with lust in his whispering voice, overcome by his body’s needs, humiliated by too horny to care, knowing full well that all of his peers are just beyond the curtains and stage he doesn’t care, he needs to cum.
Surprised at first but playing out exactly as Eugene told him, Gerald slipped the condom on that Cupcake supplied, along with the lube and excitedly went to work on the buxom bimbo.
The sissy's dress was lifted, exposing his tender and ripe round ass, as Gerald plunged into him. Gripping the smaller Cupcake by the hips as he guided the sissy up and down on his fat loser cock.
As the fat man began thrusting into the sissy, Cupcake bit his tongue to prevent himself from crying out. He knew his orgasm was close, and he wanted to enjoy every second of this debauchery.
The soft, silky sounds of Gerald's labored breaths filled the room, matching Cupcake's own rapid breaths. Despite the sweaty, greasy, and slightly intimidating nature of the situation, Cupcake found solace in the fact that this was the moment he had been waiting for all night. With his former classmates just a few yards away unknowing of the fuck fest happening behind the stage,
His arousal had reached a fever pitch, and every thrust of Gerald's thick cock seemed to bring him closer to the edge.
Gerald growled as he powerfully pounded Cupcake, taking pleasure in dominating the petite sissy. His hands gripped the sissy's hips tightly, controlling the pace and depth of each penetration. Cupcake's head thrashed from side to side, the rhythm of their bodies creating a sensual dance of lust and submission.
The sounds of their bodies colliding echoed throughout the hidden alcove, as Cupcake continued to beg for Gerald's hard cock, "Fuck me harder, Gerald! I need it!" Gerald took these words as an invitation to dominate the helpless bimbo. The sissy's moans were amplified by the surrounding darkness, adding to the intensity of the moment.
Gerald gripped Cupcake's shoulders tightly, his calloused palms digging into the sissy's soft skin.
"You want it bad, don't you?" he asked, pausing to allow the sissy to respond. Cupcake nodded fervently,
The sissy quivered in response, his body betraying his fear as the orgasm grew ever closer.
Cupcake closed his eyes, willing his arousal to peak before his orgasm. He loved the feeling of control Gerald had over him. It was a powerful reminder of how low he had fallen, yet it only served to heighten his arousal.
Each thrust brought Cupcake closer to the brink, as Gerald continued to verbally abuse him. "You love this, don't you, you little slut?” Gerald popped up from his seated position immediately pushing cupcake towards the couch, bent over, kneeling on the couch, his tits pressed against the back of the couch, Gerald started fucking Cupcake doggystyle, so close to orgasm Cupcake could only continuously beg for more more more!
“Fuck me harder Gerald! Please fuck me harder!” Cupcake’s begging only turned Gerald on more, causing him to grip Cupcake’s hair harder, forcing his face into the cushion, making the sissy even more desperate. Gerald’s thrusts were rough, forceful, deep, and hard, just what Cupcake needed. His arousal skyrocketed to new heights, every movement bringing him closer to the edge.
As Cupcake neared his climax, his moans became more pronounced, echoing through the alcove. Gerald was relentless in his efforts to punish the helpless bimbo, thrusting deeper and faster, using Cupcake's soft skin as leverage. "Take it, you little slut," he growled, his dominant nature fueling his aggression.
Within moments, Cupcake could feel his release approaching. The pressure within his loins built up as his body shook, unable to contain the imminent explosion.
Cupcake's eyes rolled back in his head, a mixture of pain and ecstasy coursing through his veins. There he was, giving in to the humiliation, submitting to Gerald's dominance, embracing his role as the degraded bimbo. The world around them disappeared as Cupcake allowed his orgasm to wash over him. The loud grunts and moans signaled the arrival of Cupcake's climax.
Gerald increased his thrusts, the slapping sound of flesh meeting flesh echoing through the small space. As Cupcake's arousal hit its peak, his body trembled, his muscles tensed, and he released a primal roar. Cupcake spurted all against the front of his dress, his orgasm overwhelming him. His scream of completion reverberated throughout the room, leaving no doubt about his intense pleasure.
Gerald held onto Cupcake as the sissy's body convulsed with passion.
Gerald realizing the bimbo had just sissygasmed from the butt fucking couldn’t contain his own orgasm anymore,
He let go of Cupcake and stood up, removing the condom as his fat cock erupted a stream of creamy jizz.
Watching the white fluid shoot out, Cupcake was both stunned by the wave that exploded onto his upturned signatured ass.
Gerald burying himself balls deep back into the twitching sissy’s hole, spots the marker in the purse and while he’s still buried in bimboi, Cupcake gets his last signature.
Gerald pulled out with a triumphant smirk on his face. He looked over to Cupcake.
With nothing to cleanup with Cupcake had no choice by to tuck himself away as best he could in the drenched and torn dress, sneaking out of the small alcove to the guild table trying to draw as little attention as he could to himself, but as the lumbering Gerald emerged from the same spot seconds behind it elicited some onlookers to gasp and laugh as the humiliated but thrilled to have orgasmed sissy returned to report his completed task.
Gerald followed Cupcake, a huge grin spread across his face, a sense of victory apparent in his every step.
As they approached the guild table, Cupcake could feel the weight of the past few hours bearing down on him, a mixture of exhaustion, shame, and relief coursing through his veins. He tried to maintain his composure, but his heart raced, and his legs shook under the strain of the evening's events. Had he begged to be fucked…harder? He thought as he told the group of nerds the final name was complete.
“Oh we can tell sissy,” cracked Simon, looking at the sissy’s disgraced and disheveled state. “Can we just get out of here now?” Cupcake asked hoping with the non stop humiliation he’d endured had been enough for today. The guild members all look at each other, smiling, knowing there’s one final surprise for their cum drenched sissy. “Sure why not Cupcake,” Eugene says to Cupcake’s surprise, halfway expecting it to get worse. “We got you a room you can unwind and relax, and of course show us all “the proof” you collected during the evening” Eugene snorted.
As the members said a few goodbyes around them they all headed to the room rented for Cupcake, who is relieved to finally be finished with the arousing game the guild had him completing. As Simon slid the card in the door and entered behind their sex drunk bimbo, all the lights were on, and all ten of Cucpake’s Conquest shouted “SURPRISE!”
Dorris, standing behind Eugene and Simon, clapped her hands enthusiastically, delighted to see the bimbo's reaction. “We know you didn't expect this,” Dorris laughed, enjoying the sight of Cupcake's shocked expression.
Simon pushed Cupcake forward, right into the center of the room where everyone gathered, staring at the sissy like it was some kind of sideshow attraction. Cupcake felt the familiar panic rising in his chest, struggling to keep his emotions in check.
“You really didn’t think we chose these guys at random did you sissy?” Dexter laughed “silly slut, they were all in on it duh!”
As they all sat around sharing stories of their sexual encounters with Cupcake, having drinks and laughing at the expense of the sissy slut, a few would leave calling it a night, thanking the guild for the shot at revenge, and Cupcake getting a handful of new phone numbers for when his cravings couldn’t be subsided.
“Well I know a few of you needed a round two, so we’re getting out of here, hey sissy, have some fun tonight!” Eugene says as the guild begin to leave. Cupcake never wishing more than to go with them, but as a few of the guys left in the room said their goodbyes to the guild, they began undressing, looking at the sissy like they were starving and Cupcake was a cartoon chicken.
Cupcake’s first gangbang was going to be a hit on the sissy porn site Simon had set up a few weeks prior. Dorris took a break from playing ringmaster to snap pictures of the sissy being ravaged by a group of friends, capturing the moment of ultimate humiliation for the slutty bimbo. The party-goers were all dressed in their finest formalwear, and the room was filled with the sound of champagne popping and laughter. The bimboi, in his torn dress, stood tall among the crowd, allowing each man to take their turn.