Chapter 3: Cupcake serves the Guild
After freshening up Cupcake tries to hide his small stiff cock in the tiny powder blue thong, but the hot pink fishnet bodysuit does nothing to help him hide his arousal...Taking Eugene's to do list Cupcake, awkwardly wobbles on his large high heels to Simon's room, silently tapping on the door as to not draw extra attention. "It's open" shouts the dweeb on the other side.
Inside Simon's room, Simon's eyes light up as he sees the sexy little slut in front of him, still dressed in his fetish inspired gear, and Cupcake can't believe how he went from his schoolyard bully to the sissy bimbo he has become. The transformation is evident on the outside, but what lies beneath his facade is a young man with a secret desire for feminization, enjoys being verbally abused and humiliated, but also loves being the center of attention, humiliating as it may be.
Hi, Cupcake shyly smiles, closing Simon's door, uhm so i was like wondering, uhm...Cupcake nervously and shyly says to Simon, "so i was wondering if you had any, uhm, specific request or uhm...demand for me," cupcake continues, it's just that uhm Eugene said you may require uhm, sexual release?" Cupcake asks Simon nervously.
Simon takes a deep breath "Well, yeah, I mean I've heard of your...fetish interests, so I was wondering if you'd like to engage in some kinky play” ...Cupcake annoyed and embarrassed already, thinking it would just be a simple hand or blow job, “sure, uhm what is it you'd like to do,” the sissy asks with both embarrassment and curiosity.
Simon leans in as Cupcake's eyes go wide at the request...Next thing Cupcake knows he's tied up to the bed, arms to the headboard and blindfolded, the coy shy Simon taking advantage of the tied up sissy as the nerd is mounted on top of the sissy using her glued on tits as a pair of cock pillows, humping away at Cupcake's jiggling tits, feeling up the bound and submissive sissy, "like a ride on the poor helpless sissy train!”
Cupcake, feeling very vulnerable and exposed, but also turned on having to submit to his captor's will and desires.
Simon takes immense pleasure in witnessing the downfall of his once-feared tormentor, who had mercilessly picked on him during their school days. As he watches the individual now face the consequences of their actions, Simon revels in the thought that others might eventually learn about the true nature of this person. He delights in imagining how shocked people would be when they discover the truth behind the facade.
As the dork continues his vigorous thrusting against the voluptuous bimboi’s artificial breasts, he unleashes a torrent of derogatory remarks aimed towards her, referring to her as an insignificant "sissy fuck doll" multiple times throughout their intimate encounter.
Knowing deep down inside he's not comfortable with the situation but his body is responding to the erotic and perverse nature of it and the pleasure it's providing him, even if he didn't want to be here, but his body cannot deny the erotica that's built-up by the sexual energy in the room.
“Damn Sissy, by that tiny tent in your panties I'd say you're enjoying this,” Simon laughs as he teasingly strokes Cupcake's much smaller cock with 2 fingers. Simon bursting with confidence now slides his cock into Cupcake's mouth, mounted on top of the tied-up sissy's head as the nerd humps the bimboi's mouth like it's a pussy.
Cupcake's eyes widen beneath the blindfold as he feels the warmth of Simon's cock filling his mouth, the musky scent of the man's crotch filling his nose. Gagging at first, he forces himself to relax and accept Simon's full length, even if it makes him feel like an object to be used and discarded.
Simon's rough and forceful style makes Cupcake feel like a true sissy bimbo, and it's not the first time he's been made to feel this way.
As Cupcake gets off on having his small, sensitive cock mocked while being used as a cock sleeve, he also becomes more and more submissive, accepting Simon's domination and control over him with each thrust and moan.
Despite the discomfort and unease, Cupcake can't deny how much he enjoys feeling pleasured, used, and degraded. Suddenly Simon stops and whips his well lubed cock out of Cupcake’s mouth, the blindfolded sissy finally gasp for air, wondering if the nerd came without him realizing, only to the moan in surprise as Simon is removing the sissy’s plug so he can ass fuck him, Simon still mocking Cupcake’s small cocklet while he prepares to slide his wet cock into the sissy’s tight round ass.
Cupcake moans in pleasure mixed with a hint of humiliation, Simon’s cock feeling like a hot wet dildo rod sliding into the sissy's tight twitching hole, not that he’d wouldn’t know what that was like, all Cupcake can do is squirm and moan involuntarily.
“Oh god, oh god,” Cupcake moans, trying to keep his voice low as to not alert the rest of the house he’s being fucked, but the intensity of the moment overwhelms him, “It's too big...it feels too good though…”
Simon laughs, “Doesn't it always feel too good for you slut? You're so tight you little fuck doll.”
Cupcake moans as he's slowly fucked by Simon's fat cock, his legs trembling with each thrust.
“Come on, Simon, ohhh fuck,” Cupcake whimpers biting his lip, his body begging for release.
Simon growls, his thrusts becoming more erratic as he approaches his climax. He shudders watching the bimboi’s fake tits dance to the rhythm of his humps as he releases inside of and onto the sissy, his cock pulsating with pleasure.
Cupcake moans in ecstasy, feeling the warm waves of pleasure course through his body. Filling his thong up with sissy cum as the superior cocked nerd tickles his prostate.
"You are such a dirty little slut, Cupcake," Simon jeers, panting as he pulls out of the sissy and wipes himself off on her thong.
Cupcake can barely bring himself to look at Simon, feeling too ashamed and humiliated to make eye contact as Simon removes the blindfold. But he can't deny the satisfaction he feels at being used like a toy for the nerd's pleasure. Cupcake’s own cum mixed in with Simon’s in her thong.
Simon unties Cupcake, thanks the sissy and sends him on his way to the next nerd on the fuck list, Dexter, the short fat science geek, as Cupcake wobbles out degrading my on shaky legs to Dexter’s door.
The sissy bimbo meets Doris, the petite and cute girl, at the door. They exchange a few pleasantries and move into the living room. Dexter is seated on the couch, his laptop open on his lap, as Doris flirts with the sissy, trying to get him excited for what is to come.
Dexter says, "Now Cupcake, according to Eugene you have some special talents, do you not?
Perhaps you can show me why you're here?"
Cupcake nods nervously, unsure of what's to come. Dexter stands up from the couch and approaches the sissy, inspecting the plug in Cupcake's ass. He then leads the sissy to the kitchen where he has prepared a special dessert for the afternoon.
Cupcake watches as Dexter grabs a few items for the dessert, intrigued by the possibilities.
He can't help but feel a sense of anticipation at the thought of what will happen next.
"This is whipped cream and a banana, I’m going to make you into a sissy banana split," Dexter explains, holding up the ingredients. "I thought it would be a nice addition to my dessert. Dexter leads the dumbfounded bimboi to his room and shuts the door, demands Cupcake to his knees after removing his plug.
He lubricates the sissy and teases him with the banana, talking dirty and playing with the sissy's pussy, making it wet and ready for the dessert.
Dexter takes his time, savoring every moment of power and control as he dominates the bimbo sissy. He can't help but smile as he watches the sissy's eyes glaze over with pleasure, and his mouth falls open in anticipation.
Dexter continues to tease the helpless bimboi, making him wait for the sweet treat that lies ahead.
"Are you ready for your special dessert, little sissy bimbo?" Dexter asks, his voice dripping with authority and dominance.
Cupcake without thinking shakes his head yes, as a banana hangs halfway out of his sissy ass, Dexter stands in front of cupcake, spreads whip cream all of his hard cock and tells the sissy to enjoy
"But before we begin, I have a request. I want you to suck my cock, just like you did for Eugene."
Cupcake hesitates, but ultimately obeys, taking Dexter's cock into his mouth and sucking on it enthusiastically.
Dexter leans back against the wall, enjoying the sight and sound of the sissy eagerly sucking on his cock.
"Oh, so you do remember what Eugene had you do last night," Dexter says, smirking.
"Well, let's see if you can remember this as well."
Cupcake doesn't reply, just keeps sucking on the cock in front of him, unsure of what'll happen next.
He knows he has to keep going, keep sucking, just like he's done before with Eugene.
The sissy’s mind goes blank, he just focuses on the taste and sensation of the huge cock in his mouth.
Dexter holds the sissy's head gently, he's enjoying the moment, the way the sissy's tongue and throat caresses his cock, its sensual and erotic, and the nerd enjoys exploring the bimboi's mouth and throat with his rod.
“Mmmm baby,” Dexter moans, as the sissy pleases the nerd, “That feels so good Cupcake.”
Dexter continues to savor each moment as he takes more whipped cream begins to cover the bimboi’s face with it, making the sissy a human ice cream sundae, enjoying every moment of the sissy's humiliation and degradation
And as the sissy moans and shivers with every lick, Dexter takes his time to tease him, the nerd relishes in the bimboi's powerlessness and the idea of the powerful man playing a sexually submissive sissy makes him laugh as the sissy takes any orders given.
As Cupcake is still on his hands and knees, banana and cream hanging from his ass, cock and cream in his face, Dexter decides it’s enough sucking, he squirts more cream into the sissies mouth, overflowing it with cream and another banana and tells the sissy
that he's going to take it up the ass with the cock and banana split.
As the sissy's face twitches nervously, feeling the cock and cream inside his mouth.
He is in disbelief and dismay at the same time, feeling so humiliated and desperate, wanting to cum so badly from his sissy cock. Dexter tossing the banana from his ass out the window, landing with a thud by the front door. Posturing up behind the bent over bimbo Dexter squirts more whipped cream in the sissy’s ass as he positions his cock to tease Cupcake’s overly sensitive ass.
Cupcake moans in delight as he feels the head of Dexter’s cock touching the rim of his butthole.
“Ah, Cupcake. You remember what to do, don’t you?” Dexter asks, his cock twitching with excitement.
Cupcake nodding quickly, his body trembling with nerves and excitement, as he takes in Dexter’s cock into his ass. Cupcake dying to cum slowly rocks back on the nerd without even being told, Dexter moaning with delight as the sissy takes him deep inside.
Feeling the sissy tighten around him, Dexter feels like a king in this moment, controlling the bimboi's body and mind, making him his sissy pet, a plaything toy for any guy to play with as he pleases.
"You like that, don't you, sissy?" Dexter asks, as the sissy moaned in pleasure, the thick cock sliding in and out of his ass.
"You're made for this. A total cock whore."
The sissy can't believe all the degrading comments that Dexter is giving him, it's like a dream come true for the bimboi, being called a cock whore, but the truth is, he loves it, it's what he wants, to be called a sissy and a whore at the same time.
"You're such a naughty little sissy, aren't you?" Dexter taunts, his words dripping with cruel delight. "I bet you want to be treated like a slut, don't you?"
Cupcake nods eagerly, his mind racing with excitement and lust, he wants to make Dexter happy and make him scream. All Cupcake wants is to be owned, controlled, and taken. Eagerly agreeing with anything this den or nerds have to say, anything to get that video back…and anything to cum again.
Dexter continues to pump his ass, laughing when Cupcake moans, smacking the bimboi’s ass in rhythm with his thrusts.
The sissy’s body quivers with pleasure, his hole tightening around Dexter's co
After ten minutes of humiliating and degrading ass-play, the nerd finally pulls out and tells the bimboi to get on his knees. “OMG,” Cupcake thought, “this fucking nerd is going to give me a facial like I’m a pornstar?”
He felt himself getting harder as he imagined Dexter’s cum covering his face and running down his chin. And all the while, a naughty grin spread across Dexter’s lips.
“I think you might enjoy this,” Dexter said, standing in front of the kneeling bimboi tugging his ready to explode cock in front of the sissy’s face. Cupcake eager to cum himself yet again, plunges his hand into his tented thong and begins to match Dexter’s tugging rhythm on his own pathetic stiffy.
As the nerd climaxes, he watches with a sense of satisfaction as the sissy's face is splattered with his nerd spunk, the first rope hitting the sissy right between the eyes
, the second shot smacking against the bridge of his nose and the third hit landing square on his mouth.
Dexter leans in closer to Cupcake, watching as the sissy has a trail of sticky cum dangling from his lips, as Dexter takes the whipped cream can and squirts Cupcake’s mouth full, mixing the cream and cum in the sissy’s wanting mouth.
"That was delicious, Cupcake.”
Looking down Dexter notices Cupcake’s tented powder blue thong dangling it’s own load of cum, the sissy had orgasmed into his panties yet again.
Cupcake still shaking from the experience, takes a moment to gulp down the slurry in his mouth, notices Dexter has pulled his sissy plug back out. Dexter gestures for Cupcake to turn around, on wobbling shaking legs Cupcake leans over the nerd’s bed exposing his ass for the dork to slide the plug back inside him. The slimy feeling of the plug going back inside him sends shivers down his spine but the empty feeling subsided as his hungry hole is once again filled.
Dexter gives him another slap on the ass “alright sissy, thank me for the banana split and facial and be on your way, head to Doris’ room next.”
Cupcake stammers “th, thank you Dexter,” voice shaky from the post orgasm ordeal,” thank you for the dessert and facial.”
Cupcake wiggles and wobbles out the door, legs wobbling, the high heels don’t help how he’s walking. What a sight it is as Cupcake speckled in whipped cream, cum still dangling from his chin, his own cum globbed in his thong, ass plugged, unsteadily using the hallway walls to support his quaking his post fucked shaky legs. Reaching the door to Doris’ room, Cupcake thinks to himself “just 1 nerd to go and I get that video back, Doris seems nice enough this shouldn’t be to bad.”
He knocks on the door and Doris opens it, a smile on her face, “oh hello cupcake,” she said in her sweet lilting voice, “come on in”
Eyes wandering up and down Cupcake, Doris says “you look like you had quite the dessert with Dexter,” she snickers at her own words.
Cupcake nodded, his ass feeling sore and throbbing from the recent events, feeling like a slut and a bimbo, he couldn’t help but wonder what Doris has in store for him.
Doris plucked at the hot pink fishnet encasing Cupcake’s body, “Delicious!” She teased, as she squeezed the DD tits glued onto the the sissy’s chest.
“I’ve always fantasized about revenge fucking that bitch of a girlfriend you have Cupcake,” Doris suddenly showing a more devious side, “but I think you will suffice as I just treat you like I would that stuck up diva!”
“I bet you go down on her whenever she wants,” Doris purrs imagining the sissy lapping at his demanding girlfriend’s pussy, “I mean with a pathetic cock like that,” she scoffs smiling at Cupcake, “there’s no way that excuse of a dick can make her cum, no I bet you’re all mouth aren’t you sissy?”
Doris laughs at the thought of Cupcake going down on his girlfriend, the idea of the bimbo struggling to pleasure his girlfriend with his pathetic excuse of a cock turns her on.
“I bet you’re a big fan of oral aren’t you sissy, with pouty plump lips like yours?” she says, with a hint of spite in her voice.
Cupcake nods his head, not daring to voice his thoughts as the nerd continues to torment him mentally.
Doris looks at the bimboi with contempt, examining every inch of the sissy. Taking in the sight of him with a sigh, Doris can't help but be turned on by the bimboi's situation.
“You really look the bimboi part, with those ridiculous fake tits and a sissy clit.” Doris then removes her robe, dropping it to the floor revealing her form, ordinarily in oversized shirts and jeans, her body is clad in leather like a dominatrix.
“You’re going to show me the exact tongue technique you use on that stupid bitch Trish, got it sissy, on the bed now, lay on your back!”
Cupcake, feeling defeated and intimidated, obeys Doris' orders and lays on the bed.
Doris grabs a whip from her toy box and begins to tease and taunt Cupcake. She starts by tracing the whip along the sissy's body, leaving a trail of desire and anticipation.
"You're going to learn to please me in the same way you please that stupid bimbo girlfriend," she spits, "You're mine for the night, Cupcake, and I'm going to show you how a real woman enjoys herself, and I’m going to imagine that you’re Trish as I ride you’re stupid slutty face!”
Doris sneered at the humiliated bimboi.
Cupcake wants to resist her advancements but he knows that it would be futile, Doris is too strong-willed and determined, he surrenders to the inevitable.
“Do you understand me slut?” Doris spouts, but before Cupcake could even answer she drops her heavy ass on his face
, forcing him to take a deep breath in and hold it, feeling Doris’s weight on his face as she leans back, her fingers toying with her pussy, masturbating slowly, taking her time, teasing and taunting Cupcake. The sissy's heart races with anticipation, his mind scrambled with mixed feelings, a mix of pleasure and discomfort, anxiety and excitement, nervousness and determination.
It's a whirlwind of emotions, as Doris starts to slowly ride Cupcake's face, the sissy's facial features twist with the weight of Doris' body, the heat of her musky fragrance fills the air, tickling Cupcake's senses. The sissy closes his eyes, taking in the moment, savoring it, and hoping it ends soon. He feels Doris' wetness against his lips, he can taste the flavor of her, salty, tangy, and slightly sweet.
"Mmm, that tongue," Doris moaned, "you must be a good little Bimboi, to be able to do that.
Trish is one lucky bitch."
Cupcake's body shook as Doris rode his face, he expertly used his tongue and plump lips as if he was worshipping Trish’s pussy, doing his best to get the nerdy Doris to climax as soon as possible so this could all be over.
Doris' moans and groans filled the room as she came closer and closer to exploding in Cupcake's mouth, the sissy could feel Doris' body tense up as she reached her peak. As Doris climaxed, her orgasm was like a tidal wave of pleasure, Cupcake couldn't help but feel a sense of satisfaction, if only for a brief moment as Doris’ thighs squeezed around his head still lapping until instructed otherwise.
"Oh sissy......you really know how to please a woman." Doris whispered to Cupcake, as she leaned forward, gently rubbing her body against Cupcake's face.
Cupcake felt Doris' heart racing as she leaned over him, her body enticing, leaving him in a trance-like state.
Still mounted on the sissy’s face Doris leans over opening a drawer beyond Cupcake’s view and withdrawals a large pink strap on dildo.
Doris chuckles as she brings it close to Cupcake’s face, still feeling the aftermath of his tongue and lips on her pussy, she dismounts Cupcake and slides the strap on harness up her thick thighs, Cupcake knowing what’s to come doesn’t say a word, worried only that he can’t possibly cum again for a third time in such a short period of time.
“Sorry Trishy,” Doris mocks calling cupcake by his girlfriend’s name, “No lube, but there’s still plenty of whipped cream in your ass to suffice!” She laughs as she pulls Cupcake’s legs over her shoulders and removing the plug from the bimboi’s hungry hole. All Cupcake can do is gulp and hope Doris is quick.
“I want you to beg for cock like Trish does, like a stupid spoiled whore! Come on sissy beg me to fuck your sissy ass!”
Doris’ voice was harsh and commanding, it filled the room and echoed in Cupcake’s mind as he felt himself helpless and vulnerable under Doris’ domineering gaze, forced to submit to her whims and desires.
“Play with your fake tits while you beg me to fuck you slut!”
Cupcake wasting no time begins to squeeze the fake tits together, pinching at the dime sized nipples atop the mounds of fake breasts as he begged Doris like a bitch in heat to fuck him with her strap on.
'Please, oh please, Doris I need you inside me, fuck me hard, like only you can!' Cupcake pleads, hoping Doris would fall for his desperate attempt to please her.
Doris responds to Cupcake's desires, relishing in the feeling of being in control, it's the ultimate power trip for her.
She plunges the pink strap on into his sissy ass with a wet squelch from his cream lubricated hole.
"Fuck! " Cupcake moans, enjoying the new sense of fullness and pleasure.
"Oh sissy, you have a beautiful ass, looks just like Trish's, doesn't it?" She teases him as she continues to fuck him with the strap on.
Cupcake feels so turned on and aroused, Doris' words and actions are making him go crazy with excitement and pleasure.
Squeezing and massaging his fake tits Doris mocks him, as she also begins to mock his stiffened stained thong as his cocklet strains against the fabric.
"Oh look, Trish's favorite little bitch Cupcake has a hard-on for me, too bad for you sissy, you're gonna have to wait until I'm finished with your ass!" She taunts.
"Look at you, all flushed and stuff. Just beg me to fuck you harder. Beg me to make you forget Trish and everything else. Beg me!" Her voice is cold and calculating as she tears through Cupcake's desperation.
Cupcake' pleads, his voice hoarse with need and desire. "Please, Doris. Please fuck me harder. Fuck me until I can't think anymore."
Doris smirks, the sound of his desperation only serving to fuel her enjoyment.
"You're pathetic, Cupcake," she says as she pounds his ass with the strap-on. She takes a sharpie from her nightstand, removes the cap as cupcake watches on, she begins writing above his sissy cock “USELESS” in a bold font.
Doris smiles, her eyes full of contempt as she finishes writing, snickering she plunges deeper, leaning over his aroused body, writing on his forehead “SLUT”.
Cupcake’s moans become involuntary as he whimpers to Doris between each thrust, “please make me cum, please!”.
Her gaze lingers on the words on his forehead as she pumps his sissy ass harder and harder.
“You like being called a slut, don't you?” Doris asks, her voice laced with malice.
Cupcake whimpers and nods, shame and humiliation written all over his face. He wants to resist but he can't, his body is begging for more. Doris mockingly takes his sissy cock between her finger and thumb and jerks him while continue to pump the strap on.
As she teases his cock while tugging it “you can cum cupcake, but you’re going eat your own sissy load when you do!” She laughs as she begins to push the sissy over the edge to climax, his eyes roll back in ecstasy as his body arches off the bed, cumming with a fierce intensity as it shoots out of his penis onto his own face.
Doris’ laughter echoes throughout the room as Cupcake comes down from his high, feeling completely drained and empty inside.
"Not done yet, sissy!" Doris exclaims, removing the strap-on and getting back on top of him. Running her fingers through the bimboi’s spunk she slips it into his surprised mouth
“Swallow it all Cupcake, show me how much of a good bitch you can be.”
Cupcake obeys and eagerly laps at the taste of his own fluids, salty, sweet and musky. As his tongue slides through the mixture of his sissy cock, Doris’ excitement and power trip is unleashed.
The idea of making Cupcake eat his own cum, while she watches, is exhilarating for Doris. She can feel her heart racing with excitement. She takes her sweet time, making sure to savor every moment, reveling in Cupcake's humiliation and degradation.
"Mmm," Cupcake moans, his tongue swirling around, trying to get all of his cum.
Doris finishing up with the used Cumcake, slipping his plug back into his ass, “now get out of my sight, Eugene will be waiting for you back in the living room!”
Cupcake slowly stands up, feeling completely empty inside, the pleasure from the strap on gone, only the emptiness and humiliation remain. He walks out of the room, closing the door behind him, he couldn't believe what just happened and feeling like Doris won.
He made his way to the living room where Eugene was waiting for him by the entrance. He can hear their conversation, he is feeling ashamed, defeated, and humiliated.
In the living room, Eugene is sitting on the couch, he couldn’t keep from smiling as the cum soaked sissy wondered in.
"Well, well, well, look who decided to join us Cupcake," Eugene said mockingly.
Realizing the rest of the nerds have been watching him on the living room tv perform sexual acts with the other nerds, his stomach sank as he realized he was never getting the blackmail video back, Eugene was making more!
As Eugene began to tease Cupcake with his remote control butt plug, Cupcake felt his heart race with anxiety and humiliation. He could feel the electric shocks coursing through his body, sending shivers down his spine. He begged Eugene to take pity on him, but Eugene seemed to be even more excited by his pain and suffering.
“You really are an airheaded bimboi thinking we’d just give you back that video!”
Eugene chuckles, his voice dripping with satisfaction.
“From now on Cupcake, you’ll be here at the Guild house twice a week, not only to be used as a sex toy, but any dates, any outfit requests, or any other uses the rest of the Guild has for you, got it?” Eugene says sternly to the used up bimboi before him, as the days events play out on the tv Cupcake’s record moans and begs can be heard throughout the house.
Stammering Cupcake replies, “yes Eugene,” looking down shamefully knowing he’s been played like a fool. “Good slut, now get going.” Simon remarks.
Cupcake grabs the large fur coat and shuffles his well used body towards the door, as the nerds begin all laughing in unison about how their plan worked perfectly…Cupcake rolling his eyes and sighing steps out the door, his heel making contact with the used banana Dexter had tossed out the window earlier causing the bimboi to lose his balance and slip, sliding off the banana peel with no grace Cupcake lands on his glued on tits onto the hood of his car as all the nerds cackle and laugh getting a few more photos of cucpake’s upturned fishnet clad ass.
Cursing and sputtering Cupcake plops into his leather seat, only for a wet squelch of a whipped cream pie to make direct contact with his plug filled ass and crotch, no doubt a “gift” left by Dexter after their romp. The nerds waive by to their new pet as Cupcake unceremoniously backs out of their driveway, eager to just get home for a hot shower.