Chapter 5: Game Night
In the dim light of the Guild living room, Cupcake stands naked except for the tiny bimbo lingerie, a paper bag over his head, complete with mouth and eye holes, and words scrawled across his body in black marker, he couldn't read due to the bag. The scene around him was chaotic – laughing and shouting as the four nerds played Dungeons & Dragons around the table. He tried not to draw attention, anymore than he’d gotten already, and the shame of serving the nerds made it difficult.
But, despite the indignity, there was something else, something he couldn’t quite put his finger on, pulling him deeper into this web of humiliation. Maybe it was his newfound submission, maybe it was the thrill of doing things he never thought possible. Maybe it was his need to cum nonstop for the nerds, they certainly knew how to make him tick. Whatever it was, it consumed him, leaving little room for anything else.
Eugene laughed as he watched Cupcake squirm.
It was amusing how Cupcake would always try to resist, but ultimately succumb to their games. Eugene could see that he had taken Cupcake beyond his limits, and now he wanted to push even further. Dexter, who had been observing the scene, approached Eugene with a mischievous grin.
"You know, we haven't used the remote control butt plug in a while," said Dexter, casually.
Cupcake flinched, knowing where this conversation was heading. "Maybe it's time we give our sissy some more stimulation." Eugene looked at Cupcake, the small device hidden in his pocket. The sissy trembled with anticipation, his ass already twitching. "Just think, Cupcake, you could experience even more sensations," taunted Dexter. Cupcake glanced at Doris, whose expression remained unreadable. She seemed unfazed by Cupcake's predicament, her stare cool and collected.
Cupcake gulped, his heart racing at the thought of having the remote control butt plug used on him. He knew just how powerful it was, how it could bring him to his knees with just a few clicks.
“Duh, let’s roll the for it, see if Cupcake is a dashing rogue able to escape a trap!” Simon excitedly shouts grabbing up the two D20 dice.
“I got a 19 and a 16!”
Cupcake’s face falls into panic, fearing the consequences of these high numbers. With a sickening sense of dread, he understands that the nerds will take advantage of the dice rolls. The room becomes silent, everyone waiting for Cupcake’s fate.
Simon hands the dice to Eugene who rolls them carefully. As Eugene looks at the results, a cunning smile spreads across his face.
"Congratulations, Cupcake," he says in a mocking tone. "Your luck has run out." Cupcake's heart thudded wildly in his chest, his anxiety mounting as he realized that the nerds were going to use the remote control butt plug on him. He swallowed, struggling to maintain his composure.
"Let's begin," announced Dexter, his voice firm and commanding.
“Assume the position sissy slut.” Eugene coyly says gesturing towards the large table for Cupcake to crawl onto as Simon and Dexter clear off the table top game pieces. Looking utterly ridiculous with his body covered in humiliating “art” and a paper bag on his head, in a very revealing see through nylon leoatard already wedgied up his ass, he crawls onto the table, slowly at first making sure it will support him, but in anticipation quickly spins with his ass towards Eugene assuming his trained position with his head down and ass up on display.
“What a table decoration!” Simon snorts eliciting mocking laughter from the other nerds.
Cupcake's cheeks flush, his face contorted in a mix of embarrassment and desperation. Eugene's grin widened, his eyes gleaming with excitement. Doris, her arms crossed, merely observed, her expression unreadable.
The room fell silent, an electric tension filling the air. It was as though time itself had slowed down, the anticipation palpable.
Eugene dipped the silicone sex toy into the nearest discarded plate of left over frosting from none other than cupcakes, and slowly teased Cupcake’s eager hole with it.
Cupcake squirmed impatiently, wanting nothing more than to be filled.
Doris, taking no part in the humiliation so far, watched intently, her fingers stroking the soft material of her pants. Her long legs crossed, she took a step forward, leaning over Cupcake. Her lips curved into a smirk, seeing Cupcake’s anticipation grow.
As Eugene began to slide the sex toy into Cupcake’s tight hole, Cupcake whimpered and shivered in response. His body trembled with excitement, the sensation of the cold silicone pressing against his hot hole eliciting a moan for his crowd.
Eugene moved slower than he usually did, drawing out the anticipation, allowing every nerve ending in Cupcake’s ass to feel the intrusion. Doris stood nearby, her dark eyes glinting with perverse satisfaction as she watched Cupcake writhe under Eugene’s touch.
As the sex toy reached Cupcake’s prostate, his entire body shook with ecstasy. Every muscle tensed, his face scrunched in blissful agony.
The feeling of being controlled by the nerds, combined with the invasive sensation of the plug in his ass, created a perfect storm of humiliation and arousal.
Eugene continued to thrust the toy in and out of Cupcake's body, increasing the pace and intensity. Cupcake couldn't help but moan loudly, a mixture of pleasure and humiliation surging through him. His hips bucked involuntarily, trying to accommodate the foreign object in his ass.
His muscles clenched and released, milking the invader. Eugene buries it to the hilt as he slaps his sissy’s bubbly ass as he then tells the dazed and horny bimboi to get off the table so they can continue their d&d session.
Cupcake obeys reluctantly, climbing off the table with his limbs wobbling slightly from the intense sensations and the high heels causing a slight imbalance. He then steps back and watches helplessly as the nerds return to their respective seats, picking up their respective characters.
Annoyed Cupcake impatiently watches on as the nerds go about ignoring his presence, or turning to mock the small tent in his leotard from his unimpressive erection, occasionally Eugene will changed the plugs patterns with the remote which they all get a laugh about the moan or squeak that Cupcake would make. Still having to fetch them drinks or snacks as he’s body was groped and fondled each time he returned, he was completely on edge and anticipating being fucked silly later by Eugene.
After hours of play, the nerds finally called it a night.
As they gathered their belongings, Cupcake could only stand idly by, his heart heavy with anticipation. He knew what lay ahead - a night of degradation and servitude to the head nerd.
Eugene grinned as he whistled as if calling a dog as he headed to his room, the nerds all laughing as Cupcake eagerly followed while adjusting his tented leotard and paper bag on the way. The sissy needed to cum so badly that he was willing to make a mockery of himself as long as it led to an orgasm.
As they entered Eugene's room, Cupcake felt an unexpected wave of relief mixed with excitement. He was familiar with this territory, having been here many times before when Eugene had his way with him.
Eugene closed the door behind them, locking it securely. He tossed the remote control on the bed. Eugene motioned for Cupcake to come closer, his smoldering gaze demanding submission.
Cupcake complied without hesitation, stepping closer, the sound of his high heels clicking on the floor adding to the sense of domination. Eugene grasped Cupcake's jiggly ass, guiding him to the center of the room. Cupcake eagerly wiggled it, anticipation burning in his undersized lingerie. He knew that this was the moment he had been waiting for all night.
What the sissy didn’t anticipate was Eugene pulling out his phone and snapping all sorts of photos of the sissy’s drawn on body, commenting and laughing about certain areas such as “Size Matters” above the sissy’s erect cocklet or the caption of “Butt Slut” on his lower back, of course he zoomed in on the withered and crumpled paper bag on the bimboi’s head, the silly face drawn on it with cartoon oversized glasses with giant pink lips decorating the mouth hole, “BOZO” written on what would be his forehead.
Cupcake blushed crimson, mortified and yet thrilled by the attention his body was receiving.
“This should be quite entertaining,” Eugene said snapping a few more pictures before setting the camera in the normal spot to record their fuck session, gesturing for Cupcake to crawl over and open up his high waisted pants, as Eugene slid off his shoulder suspenders. Grinning ear to ear as the submissive sissy complied dutifully going right to work on the nerds zipper and sliding Eugene’s pants to his ankles, all the while Cupcake's own tiny cock straining against his nylon crotch.
Eugene pushed Cupcake to his knees, his hand resting on the bimbo's head, forcing him to look upward, his lips parted as if begging for permission.
“You know the drill, right?” Eugene purred. “Yes, Master,” Cupcake replied breathlessly, his voice thick with desire. “Well, get those cock pillow lips of yours to work,” Eugene responded, amused. “Be a good slut tonight and maybe I’ll let you have your own cupcake tonight” Eugene smirked knowing he already planned on having the sissy cum into a cupcake just like he was planning on cumming into Cupcake.
Cupcake nodded enthusiastically, practically salivating at the prospect of being used in such a deliciously humiliating manner. His cock twitched, a sign of his arousal and excitement at the thought of serving his master in this capacity and finally getting his orgasm.
Sucking cock through the paper bag as Eugene giggled at the sight of it, Cupcake enthusiastically gave the blowjob of his life, deepthroating the dominant nerd’s long erect cock, leaving a saliva trail from inside the bag to the tip of the throbbing penis, as the bag got drool logged around the mouth hole from the constant bobbing back and forth the sissy knew he was putting on an absolute show for the camera.
Eugene stepped away, giving Cupcake a chance to admire his hard cock in front of the mirror, his hands reaching to stroke it, imagining it deep inside Cupcake's tight, wet hole. His desire building rapidly, a fierce passion flaring in his chest.
Eugene stepped away, giving Cupcake a chance to admire his hard cock in front of the mirror, his hands reaching to stroke it, imagining it deep inside Cupcake's tight, wet hole. His desire building rapidly, a fierce passion flaring in his chest.
As he looked into the mirror, he could see the reflection of Eugene standing proudly behind him, towering over him, his dominant stance reminding Cupcake exactly who was in charge. This image served to further intensify Cupcake's arousal, pushing him even deeper into submission.
The idea of being dominated by Eugene, the head nerd, while wearing the shameful leotard and paper bag covering his face, brought immense pleasure to Cupcake. His desires were being played out, and there was no denying the power of these emotions as they coursed through his veins.
Feeling confident and eager, Cupcake positioned himself on all fours, presenting his eager hole for Eugene's takeover. His entire body trembled with anticipation, and his mind raced with thoughts of how pleasurable this night would be. Eugene popped the sissy’s plug from his tight cock hungry ass, causing the bimboi to moan knowing what’s replacing it.
Eugene reached for his trusty bottle of lubricant, drizzling it liberally onto his rock-hard cock. Cupcake as Eugene applied some to his ass, probing his hot wet hole with his fingers.
Taking a deep breath, savoring the power he held over Cupcake. "You know, you really should be thanking me," he told Cupcake, his voice low and commanding. “If it wasn’t for me catching you that night you’d probably be at home disappointed that sexy girlfriend of your with that worthless little cocklet!” Eugene smacking the bimboi’s bent over ass.
"Fuck me already!" Cupcake demanded uncharacteristically. Eugene caught off guard at first smiled and obliged, impaling Cupcake's tight hole with his rigid cock. Cupcake groaned, feeling Eugene's length slide in, stretching him painfully but oh so pleasurably. "That's it, Cupcake," Eugene growled, taking hold of Cupcake's head underneath the ruined paper bag, controlling the sissy's movements.
"OOOooohhhhhh fuckkkkk!” Cupcake moans his eyes closed in pleasure, not even realizing he demanded to be fucked.
His whole body quivered in ecstasy as Eugene drove deeper and deeper into Cupcake's tight hole. The bimboi cried out, begging for more as his body shook with every thrust.
"Oh god yes, fuck me!" Cupcake screamed, clenching his ass tightly against the superior nerd cock. His legs trembled as Eugene continued his assault, thrusting in and out with increasing force. “Fuck my dumb sissy ass Eugene!”
“My my I see the ‘Butt Slut’ above your ass was just Dexter being funny, but you sure
are enjoying it aren’t you, you cock drunk sissy Butt Slut?” Eugene replies resting balls deep inside the Cupcake, smacking Cupcake’s exposed cheeks, the bimboi enjoying the verbal abuse as each ass smack makes him buck his hips backwards impaling himself more.
"Your cock is so big! It feels amazing." Cupcake gasped, his brain fogged with desire, his thoughts swirling with the sensations of Eugene's powerful thrusts. The sissy loved how much bigger Eugene's cock was compared to his own, Eugene on cue reaches around Cupcake’s hips and teases the sissy’s erection through its nylon encasement, wet with precum just from being fucked.
"So small, isn't it? Not enough to satisfy anyone, especially a real woman.” Eugene mocked, grinning at Cupcake's discomfort. "But you must love it, since you're always showing it off."
Eugene teased, smacking Cupcake's exposed ass cheek again.
Cupcake whimpered, the mix of pain and pleasure pushing him closer to the edge. "Please, please cum inside me," Cupcake implored, his need for release becoming increasingly desperate.
Eugene grinned wickedly, relishing the power he had over Cupcake. He pulled out, then thrust back in harder than ever, sending Cupcake reeling. Cupcake gasped and moaned, writhing in sheer ecstasy as Eugene continued his brutal assault. Eugene kept up the verbal domination, calling the sissy every name in the book
“Sissy” “Slut” “Cum Dump”
as he plunged deeper into Cupcake's now well-trained anal passage. Cupcake's cock twitched violently against his nylon crotch, begging for relief as he felt himself getting closer to the brink.
Eugene paused briefly, grabbing Cupcake's cock roughly and jerking it. "Not yet, sissy," he taunted, thrusting back into Cupcake's ass.
Cupcake's eyes rolled back in his head, his body shuddering with each powerful thrust. "Oh god, oh god!" Cupcake screamed, his nails digging into the carpet beneath him as his release neared.
Eugene increased the pace, driving himself deeper and deeper into Cupcake's hot, tight hole. "Fuck me harder!" Cupcake screamed, desperately seeking his release. "Is that all you want?" Eugene mocked, pulling out and slamming back in.
"You're going to cum soon, aren't you?" Eugene continued, teasing Cupcake mercilessly. Cupcake nodded frantically, desperate for release, his cock spasming violently in his nylon crotch.
Eugene picked up the pace, hammering away at Cupcake's stretched hole, each thrust hitting a new level of intensity. "This is what you wanted, right?" Eugene said, the sound of his heavy breathing filling the room.
He took his weight on his arms, leaning down to Cupcake, pinning him down on the floor. "Just remember, you can only take one more round before your tiny pathetic cock gives out, so make it count."
Eugene shifted, aligning himself with Cupcake's opening. With a swift push, he entered Cupcake fully. As Cupcake moaned, Eugene began to thrust, his rhythm punctuated by grunts of satisfaction.
Eugene increased the speed, pounding into Cupcake like a battering ram.
His large cock was a perfect fit for Cupcake's tight hole, and Cupcake couldn't help but moan in pleasure as he felt his body being taken by the dominant nerd. Each thrust sent waves of pleasure throughout Cupcake's body, amplifying his desire for more.
The bimboi's moans filled the room, growing louder as Eugene's rhythm intensified. The sissy's body quivered in ecstasy, feeling as if it were about to explode from the sensations.
Cupcake's arousal grew stronger, his thoughts consumed by the incredible sensations flooding his body. Each thrust brought him closer to the edge, making him beg for more.
"Please, please cum inside me," Cupcake pleaded, desperate for the release that would bring him both relief and shame. Eugene smirked, reveling in his power over Cupcake as he continued to thrust deeper into the sissy's tight hole. With each thrust, Cupcake's body quaked in response, as though it couldn't contain the pleasure building within him.
Eugene's large cock sliding in and out of Cupcake's tight hole created an intense friction that seemed to amplify the young man's desire.
Cupcake lost in sexual bliss, although he’d deny how incredible it felt, then felt something cool slip over his throbbing cocklet, looking down he realized Eugene had stuffed an icing drenched cupcake over the sissy’s little cock as if it was a pastry pussy. Cupcake gasped at the new sensation, knowing the nerd intended for him to blow his pathetic load inside the pastry.
He didn't understand why Eugene was doing this, but he knew it was another way for the nerd to dominate him, to control his orgasm.
Eugene continued to thrust into Cupcake's tight hole, increasing the pressure as the sissy's climax drew near. The feeling of having his tiny cock stuffed into the icing-covered pastry added a new layer of humiliation to Cupcake's already tortured experience.
Each thrust became more intense, more demanding, as Cupcake approached the edge of his release.
He could feel his body trembling, his heart racing, as the feeling of pleasure engulfed him. It was in these moments that Cupcake experienced the full extent of his vulnerability, his submissiveness. It was the thrill of losing control, knowing that Eugene held his fate in his hands.
Eugene, seeing the imminent explosion in Cupcake's eyes, picked up the pace. He hammered into Cupcake, each thrust echoing throughout the room. Cupcake moaned, his entire body quivering with each penetration.
As the intense sensations coursed through him, he felt a rush of shame at being taken so roughly by the nerd. Just as Eugene landed another ass slap the sissy came, blowing his pathetic load inside the now cream filled cupcake, as his ass clenched around Eugene’s superior cock the nerd’s orgasm followed, filling up his Cupcake.
Eugene grinned, enjoying the victory, feeling his warm semen pulsating inside Cupcake's body.
"There you go, sissy." Eugene said, his voice filled with triumph, “Enjoy your dessert,” laughing ass he jerked his remaining load onto Cupcake’s spent ass.
Cupcake laid there, panting heavily, sweat dripping down his face. He felt empty and ashamed, a mixture of feelings that he could not comprehend. He looked down, feeling the weight of his cum inside the pastry and the aftermath of his submission.
Eugene rolled the exhausted bimboi onto his back, taking the cum filled cupcake in his hand, “once you’ve finished your dessert get this place cleaned up and I’ll see you tomorrow, we have very exciting news for you Cupcake!” With that the nerd shoved the pastry into Cupcake’s dumbfounded mouth
, leaving him to enjoy his own cum inside the sweet treat.
Cupcake lay there, stunned, as he processed the events of the evening. The thought of eating his own cum filled him with a mixture of disgust and arousal. What kind of news could be more exciting than this? He wondered nervously. As he got up, his exhausted sweat coated body, he made the walk of shame past the other nerd’s open doors to the shower, finally removing the ruined paper bag as nerd cum dripped down his quaking thighs.
Cupcake stepped into the shower, allowing the steaming water to rinse away the sweat and shame. He stood under the pounding water, letting it wash away the lingering remnants of his degradation. He didn't know why Eugene had given him such a challenge, why he had put him through this humiliating nightmare. But he knew one thing for certain: he had no choice but to submit to his every whim.
The next day, Cupcake arrived at the Guild, eager to learn whatever new information Eugene had planned for him.