Of Joy Boys and the Joys of Boys
Button Mash sat alone in the hallway in a dead-end corridor not far from the school library. In his hands, he held what was currently his most treasured possession: his beat up old Joy Boy. Since coming to the Canterlot Higher Education Institute—Canterlot High for short—he valued every chance he got to duck away for his gaming fix. Just being allowed to bring this much to school was a small victory in his eyes. After all, his mom sent him to this college-prep school to get away from the distraction of his video game consoles.
So here he was, in between classes playing through a level of Banana Quest 3: Straight to the Moon, where he had peace and quiet. Normally, he’d be off with his classmates, migrating to his next class, but he had to get away from it all. It’s not like he had any real friends here. None of the students in his age group at the private school shared any of his interests, and none of the older guys in the geek clique wanted to put up with a runty nineteen-year-old whose only interest was video gaming.
That left Button incredibly alone, and easy pickings for bullies like Snips and Snails: two unicorn bullies whom he shared many of his classes with. When the pair weren’t following around that horrible Sunset Shimmer unicorn, they were picking on him. In class, they’d throw paper balls at him, or try to get him in trouble by passing notes, but outside of class it was worse; beyond being called horrible things like a no-account, basement-dwelling loser they liked to trip him up in the halls, spill his backpack, and steal his lunch tickets. They once even locked him in a locker. He couldn’t just go to Vice Principal Luna or Principal Celestia though; they’d beat the shit out of him. Just the thought of what they might do gave him the willies.
“Well lookie what we got here, Snails,” a familiar voice called out from the end of the hallway, causing the fur on the back of Button’s neck to rise.
“Oh no!” Button whispered under his breath, watching out of the corner of his eye as the two guys approached. Hurriedly, he hit the off-switch on his Joy Boy and tried to tuck it into the front pocket on his black hoodie. In his rush, he fumbled and the durable little handheld dropped to the floor, skittering a few feet away.
“Looks like it’s Butt Mash, tryin’ to hide from us,” the other laughed grimly. “He’s even dumber than people think I am.”
Reaching out one hand, Button snatched up his prized possession before leaping to his hooves. “C’mon guys, just lemme alone!” he nearly shouted, backing his way into a row of lockers. “You already got my lunch ticket!”
If the two were listening, they didn’t show it. The taller, green maned man just gave him that mockingly dopey grin, pointing at his hand. “Whassat you got there, Butts?”
The pudgier of the two snorted before rolling his eyes. “It’s one of those queer girly games, obviously.” Snips waves a hand dismissively. “Look at him! All short and skinny, and his mane’s way too long for a dude. He’s practically a chick, anyway.”
“Cut it out guys!” Button cried, sliding along the wall of lockers, backing himself further into the dead-end hallway. “I don’t care if you beat me or steal my lunch tickets, but you guys back off and leave my Joy Boy alone or I will tell, regardless of what you’ll do.”
The taller brute strode closer, an unimpressed look adorning his goofy face. “Wow, I’m quaking in my horseshoes,” he replied dismissively. “Nah, you won’t tell anybody. You wouldn’t want the VP to know you were cutting class, would you?”
Snails was right in front of him now, towering over Button. “I won’t give it to you!” Button cried. Without thinking, he struck out with his free hand, landing a feeble blow on his bully’s horn.
“He hits like a chick, too,” Snails laughed maliciously, before slamming his hoof into Button’s gut and snatching away the treasured device. He grinned as Button fell to the tiled flooring, clutching his stomach. “Since he’s such a bitch, he should have no problem going into the women's bathroom to go get it back, right?”
“Yeah!”
Just like that, Snails threw the Joy Boy down the hallway to Snips. The shorter, chubby guy caught it with his magic and took off at a lazy jog down the hallway around the corner. Without even waiting for the winded Button to come to his senses, Snails booked it after his partner in crime.
The hoots of laughter floated back down the hallway as he heard the crack of bouncing plastic and a closing door. They really did it? Why did the two have to be such jerks? He’d never done anything to them, but they insisted on targeting him. Now he had to go into the women's restroom to get his game system back!
Groaning in pain, Button pushed himself onto his hands and knees, trying desperately not to cry. After a few strained breaths, he felt steady enough to get back onto his hooves without bursting into tears. If he got caught, he could very well be expelled, regardless of whether or not it was his fault. Why did those guys have to be such... such... assholes?
Warily, he trudged up the hallway and around the corner. With each step, his sense of dread amplified. What if he was seen? “Damn it!” Button moaned, coming to a stop in front of the restroom. “This is so stupid! Why here of all places?”
Frowning, he looked at the door. It had an out-of-order sign up, partially covering the sign marking it as the women's room. If the rumors were true, this was the bathroom the popular chicks came to do things they weren’t supposed to do on school property, like smoke or trade medication. This was definitely the worst bathroom to risk being caught in, for entirely different reasons.
“Gotta make this one quick,” he promised himself. Making sure the coast was clear and he didn’t hear anyone inside, he ducked into the bathroom, quietly easing the door shut behind him. Almost immediately, he paused out of morbid curiosity to take in the sights of the bathroom. Unlike the men’s rooms in the school, a nice mix of light blue and yellow, this bathroom was done up with light pink stalls and counters, with a faded floral print wall. Whereas the bathroom he was used to had a mix of urinals and stalls, this one had only stalls, and what he could only imagine was a tampon dispenser by the counter.
Shaking the curiosity from his head, he looked frantically about the chamber for his electronic device. It wasn’t near the counters, or in the middle of the floor, so did that mean it ended up in one of the stalls? There was only one way to find out!
Lowering himself onto his hands and knees, he crept along the line of stalls, peering under the doors in search of his precious toy. His spirits dropped more and more the further he got along without finding the thing. What if Snips and Snails had duped him? Now he was probably going to get kicked out of the school, and all the money mom had spent sending him here would have gone to waste!
Just when he’d given up all hope, Button’s eyes alit on the object of his desires. Glancing at the doorway, he realized he was at the final stall. The Joy Boy wasn’t within his reach, though, so he stood up and entered the stall. “Thank God, I found it!” he whispered to himself.
Leaning down to pick up the abused piece of plastic and circuitry, his fingers grazed something else beneath it. It was smooth and soft, like some of his mother’s clothing. Was it some women's handkerchief? Momentarily pushing aside his prize, he picked up the soft fabric and held it out in front of himself with both hands. It wasn’t a discarded kerchief, but rather a pair of white cotton panties with a tiny pink heart on the front.
Just then, he heard the door open. “Are you sure you didn’t leave them in the locker room, Silver Spoon?” a classmate’s voice—that older, snobby earth pony Diamond Tiara?—came to him. “I don’t wanna waste our entire break looking for your damn underwear.”
“It has to be here!” another woman, presumably another earth pony classmate, Silver Spoon, responded almost too quickly. “The only time I even took them off was when we did that before class!”
Oh shit! They were here looking for what he currently had in his hand! He felt his stomach drop beneath him as panic set in, and he hurriedly sat down on the toilet seat, bringing his legs up to hug his knees to his chest. Almost as an afterthought, he reached over and silently closed the lock on the stall. Maybe if she didn’t see her panties on the floor, she’d assume she left them somewhere else?
“Do you remember which stall we did it in?” Diamond asked as the clicks of their high-heel horseshoes drew closer. “You’re always kinda rough, so I don’t really remember.”
“Easy!” Silver giggled in a playful tone. “It’s always the last stall, remember?”
Button froze as he spied a pair of purple booted horseshoes beneath the stall door. The door jiggled a few times before he heard, “It’s locked!” There was a short pause before a gentle knock. “Um, excuse me, I think I might have forgotten my... underwear in here. Have you seen them?”
Oh great! Now they expected him to reply? “U-um, no,” he replied, trying his best to imitate a chick’s voice. His ears folded against the sides of his head in shame. “I t-think I saw those Snips and Snails jerks in here before.”
From the other side of the door, Button heard hushed muttering, and what sounded like a phone being dialed. After a few moments, he heard Diamond Tiara speak up. “Snips, what did we tell you about encroaching on our turf!” Diamond all but shouted into her phone. “You know Sunset only tolerates you two because you promised to stop going into the women’s bathrooms!”
There’s a long pause from her as she listens intensely to the person on the other end, and then Diamond asked, “What do you think he meant by ‘a surprise waiting for you,’ Silver Spoon?”
“I don’t know, but whoever’s in there had to be lying,” Silver answered crossly. “Open up in there and gimme my panties back.”
“N-no!” he countered. “D-don’t come in!”
Button almost wished at that moment that he had just decided to throw the panties over the door at them and hope they went away, because almost immediately after he told them no, the lock snapped and the door burst open. Standing in front of him were the livid forms of Silver Spoon and Diamond Tiara, and they were staring at him. To make things worse, they saw the balled up cloth poking out of one of his hands.
“Ohmygawd, Silver Spoon!” Diamond crowed with laughter. “It’s that wimpy Button newbie, and look! He’s got your panties!”
He stared back in horror at the pink-furred vixen and her queen-bee themed outfit. She had her phone out, and it looked like she was filming everything. Blushing through his coat, he dropped the panties and covered his face. “N-no!” I denied. “I was just in here looking for my—”
“Feminine side?” Silver Spoon completed for me, mockingly. “A girly freak like you would, wouldn’t she?”
Why did everybody think he was girly? So what if he was short, skinny, and had longer mane than most guys did. Mom liked his mane that way. “I’m not girly!” he shouted, leaping to his hooves, coming snout to chin with Silver Spoon. “I’m just underdeveloped!”
A disturbing smile crossed Silver Spoon’s face, and she pushed him back down onto the toilet seat. “It’s okay, Button!” she crooned mockingly. He watched in abject horror and fascination as the person in front of him began loosening the spoon shaped brooch holding her white neckerchief beneath the collar of her blouse. Oddly, he found himself remembering the foreign schoolgirls in one of the special picture games he saw on his mom’s computer, and the more he stared, the more her clothing reminded him of those outfits. “We can help you.” Dropping her smile, she ordered him in a flat voice, “Strip.”
“But—”
“Button it, Button,” Diamond Tiara cut him off, making sure she caught everything on her camera phone. “If you don’t want us to blab, you’ll do exactly as we say.”
For what must have been the third time today, Button felt like crying. He was in an impossible situation that could only end badly for him. They were either going to get what they wanted from him, or they were going to get him expelled, just like Snips and Snails—possibly both. Maybe if he just did what they wanted, they would only make his life hell. He didn’t want to disappoint mom!
Sucking in a shameful breath, he grabbed the hem of his hoodie along with the band tee beneath, and lifted both above his head, doffing them onto the floor between him and Silver Spoon in a single motion. Raising his hips, he unbuttoned his denims and lowered them down his brown-furred legs. Removing the pants, he kicked of his high-tops before looking pleadingly at his two new tormentors.
“The boxers too, Button,” Diamond Tiara commanded, a malicious grin plastered on her face. His shame intensified as he raised his hips to lower his boxers to the floor. Despite trying his best to hide his shame, the women got more than an eyeful of his manhood before he snapped his hands over it. “Wow, he’s so small! No wonder he wants to be a woman!”
“I don’t!” he whimpered feebly.
Grinning, Silver Spoon leaned down in front of him to pick up the discarded pair of panties. “Put these on, girl,” she said in a domineering tone like nothing he’d ever heard before. She dropped the panties on his lap, trying her best to stop snickering. “They’ll suit you much better than those ugly guy clothes.”
Swallowing shallowly, he obeyed and stood up, putting his legs through the holes before running them up his legs. A shiver of unease and excitement ran up his spine at the sensation of the silky-soft cotton rushing up his legs to cradle his small genitals. “Look! You can barely even see it!” Diamond guffawed. “Give him the rest of your clothes so he can complete the look!”
Silver Spoon gave Button a sensual smile before turning around and gingerly removing her blouse. Hanging that on the door for a moment, she removed her white little brassiere, turning back as she passed it to him. He looked in confusion at the breast supporter before glimpsing the older woman’s petite breasts, covered in a fine gray fur and capped by two rosy-gray nipples.
The bra sat momentarily forgotten in his hands as he stared at the first breasts he’d ever seen in real life that hadn’t been his mom’s. They weren’t really big, and most of her small bust was accounted for almost entirely by her large areola, capped by two pert little nipples. In spite of the situation, he found himself growing hard, straining against Silver’s panties.
“Don’t just stare; put the bra on!” she scolded, crossing her arms in front of her chest. Her ears twitched visibly in agitation. “All girls your age need to wear bras!”
Button didn’t really agree—he had no breasts, thus no need for the support—but he didn’t think it wise to voice his objection. These chicks held his life in their hands. Slowly and clumsily, he managed to slip the bra on and do the clasp in the back. Much to his chagrin, the band fit perfectly around his chest.
“Eww! He got a boner!” Diamond laughed, pointing one hand at his burgeoning erection. “Gross!”
Frowning, Silver Spoon undid the side-clasp to her pleated magenta skirt, letting it fall to the floor. Button got only the slightest glimpse of her bald mons pubis before she stepped out of the boots and the skirt, bending over to pick up the skirt and hand it to him. “Put these on, and then put on the blouse,” she ordered, turning around and gathering up all of his clothing. She walked out of the stall, taking only a moment to snatch up a backpack laying beside Diamond’s hooves.
“Once that’s done, I’ll help you do your make-up, Buttonette!” Diamond trilled giddily. “Silver Spoon has a very special surprise for you!”
“I really don’t like the sound of that,” he whispered to himself, pulling the skirt up his legs and doing the side-clasp up once it was at his waist. Again, he found himself frowning at how well her clothing fit him. Surely he wasn’t that girly, right? The question once more popped into his head after putting on the boots and blouse, both of which fit disturbingly well.
Resigned to his fate of degradation, Button stepped out of the stall, making sure to adjust the neckerchief and brooch. “Let’s get this over with,” he muttered to Diamond Tiara before looking dejectedly at his reflection. Aside from the purple outfit clashing with his long orange-ish mane, he couldn’t say it looked bad on him, if not only for the fact that he barely recognized himself. The blouse was cut in a manner that exuded femininity, and coupled with the skirt and high-heeled boots, there was no mistaking himself as male. Instead, he saw an underdeveloped young woman.
“There, see? Was embracing your femininity that hard?” Diamond asked softly, taking a container of blush from her purse and applying some to his cheeks. “If you took better care of your mane and tail, we might even make a proper woman.” Putting that away, she moved on to eyeliner, and then a mascara pencil. “It’s just a shame you’re really a guy. You might have been my type,” she added, applying some lip gloss. “There, say cheese!”
Button put on as best a smile he could muster as she snapped a picture of him with her phone. For the most part, he hoped that picture, and whatever video she’d already taken, never saw the light of day, but at the same time, this was all getting rather exciting. They’d blackmailed him into doing this, sure, but at the same time, he didn’t even recognize himself. The woman in the mirror looked like someone he might have even pined for.
Staring at himself in the mirror, he caught sight of a stall door opening. Out stepped Silver Spoon, clad in his black hoodie and blue-jeans and everything else. With an exaggerated swagger, she strode out of the stall, coming right up behind him before firmly grabbing his ass through the skirt. Turning to her in surprise, he did not like the lascivious look on her face.
“Mmm, girl, you are looking fine,” she said in her deepest voice possible. She pulled him chest to chest against her, one hand still firmly on his butt. “I’ve got a big surprise for you. Get on your pretty little knees and close your eyes.”
Again, Button Mash couldn’t help but feel this was taking a weird direction, but these two were clearly in control. If he did the wrong thing at the wrong time, he didn’t really want to know what would happen. Lowering himself onto his knees, he waited curiously for the big reveal.
At the sound of a zipper, he frowned. “Open your eyes now, girl,” Silver commanded, making it clear that it wasn’t an option. When he opened his eyes, he was greeted by the sight of a long, erect penis just jutting out of the fly of his boxers and jeans. Upon closer inspection, the gray phallus was entirely rubber in make, but it matched Silver Spoon’s fur perfectly. “You might want to start sucking that, girl. You’re going to need the lubrication.”
Wide eyed terror filled Button’s face as he stared up at Silver Spoon. Out of the corner of his eye, he glimpsed Diamond Tiara hauling herself up onto the bathroom counter, ass almost flush against the mirror, phone clutched firmly in one hand while the other looked to be rubbing her belly teasingly. “Don’t you think this is going too fa—”
Silver Spoon never got the opportunity to hear him finish his thought. As soon as she had the right opportunity, she thrust forward with her strap-on, filling his mouth with rubber. Instead of tasting only of rubber, however, he found the toy to have a rather musky, slightly acidic flavor. It wasn’t bad, but it also wasn’t great. All the same, he found himself willfully taking more of the rubber shaft into his mouth, past the medial ring, even, in order to taste more of that odd flavor.
“You should be happy, girl,” Silver Spoon jeered, grabbing at the back of his head. “That was inside Diamond earlier, and she doesn’t let just anybody taste her.” He looked up at her warily, before glancing again in Diamond’s direction. To his surprise, Diamond wasn’t rubbing her belly anymore; instead, her fuzzy white skirt was hiked up, and her hand was now sensuously caressing her vagina through her spats. “If it makes this any easier, pretend you’re eating her out instead of sucking cock,” she added, drawing a pleasured moan from Diamond Tiara.
By Button’s guess, this might be the closest he’d ever get to eating a chick out for some time, so he figured he might as well savor the flavor. Extending his tongue, he lapped greedily at the rubber length, bobbing and twisting his head sloppily in order to get as much of the taste as he could. The sloppier he got, the more his saliva coated the rod, and the greedier he got in turn.
“Okay, that’s enough,” Silver Spoon commanded, pushing his head away and snickering as the flared head popped free from his mouth. “You really got into that, didn’t you?” Button barely paid her any mind. He was too focused on pooling all his saliva in one spot in his mouth, determined to consume what remained of Diamond Tiara’s juices. “Now, stand up, and lean over the counter,” Silver ordered, guiding him up placing him at an angle where he could see Diamond’s crotch through her drenched spandex shorts. “Ass up in the air.”
Following the dom’s instructions, Button thrust his little chocolate bottom in the air. A big part of him was horribly put off by the idea of being fucked in the ass with that big rubber dildo, but with his boner aching, and the sight of Diamond’s damp cameltoe mere inches from his face, he figured it might not be that bad. He was grasping for straws more than anything, but maybe if he behaved, he might be allowed to reciprocate.
With an amused snort, Silver Spoon flipped the skirt up over his back, and grabbed ahold of the sides of Button’s panties. She lowered them just enough to have free access to his tiny pucker. “Now, this might hurt a bit,” she explained, placing one hand firmly on his shapely little ass and grabbing his tail with the other. She giggled a bit, lining up the rubber rod with his anus. “That’s okay though; it just means you’re becoming a woman! A woman’s first time always hurts!”
Gritting his teeth, he clenched his eyes shut as the strap-on forced its way past his sphincter. It hurt, feeling himself stretch to accommodate the girth, but he’d felt a similar pain when taking a particularly large dump, so it couldn’t be that bad ‘cause those felt good in the end, right? He groaned as she eased the shaft slowly in, and he was unable to suppress a moan when the head of the dildo brushed a certain spot inside him, eliciting an involuntary twitch from his penis.
As Silver Spoon began to slowly ease the shaft out of him, he moaned once more. The feeling was definitely not unlike taking a particularly satisfying shit, he found. The babe obviously had some experience doing this, as she drug it out slowly until only the flare remained inside, at which point she thrust in hard, striking that spot—his prostate, wasn’t it?—inside him once more.
“Button, if it bothers you thinking about this as sodomy,” Diamond Tiara said in an almost dreamy tone, “Perhaps you could pretend you have one of these, instead.” Opening his eyes, he saw Diamond Tiara had taken off her spats—at least, in part, as they hung from her fetlock—and was now spreading her pink, winking vagina for him. The phone sat completely forgotten in the sink.
He watched in fascination, momentarily distracted from Silver Spoon’s slow withdrawal, as Diamond angled her hips so he could get a better view of her pussy and ass. Slowly, teasingly, she traced one moist finger down her furless snatch to her butt, pointing at her anus. “Instead of fucking you here,” she moaned encouragingly, watching the scene before her with half-lidded eyes. She moved her finger up to her spread labia, indicating her birth canal. “Pretend she’s fucking you right here.”
Silver Spoon thrust into his ass once more, synchronizing with Diamond Tiara as she pressed one finger into her pussy, straight up to the knuckle. Moaning again as the dildo caressed his young prostate, he did his best to do as Diamond Tiara asked. Instead of being fucked in his ass, Silver Spoon was fucking him in his incredibly tight formerly virgin pussy. With that mental image in mind, he found Silver Spoon’s ministrations felt somehow better than before.
Strangely, the fantasy didn’t stop there for him. He really began to buy into the whole roleplay, and started imagining Silver Spoon was a guy, thrusting his warm, hard cock into her sopping wet pussy, eager for him to cum and impregnate her with his foals. Up until now, Button’d never thought about any of this beyond sex-ed, but feeling it put into practice, he couldn’t imagine life without this.
Again and again, Silver Spoon thrust into him, her own quiet moans adding to the chorus of Diamond’s and Button’s rising voices. Each battering of his prostate drew out another twitch from his little joystick, and he began leaking a steady stream of pre-seminal fluid into the gusset of his borrowed panties. Eventually, he began to feel a pressure build up between his loins, and his moans turned into cries, and near shouts.
“Quick, gag him with something before someone hears!” Diamond exclaimed, rubbing her young mound with fervor. “Anyone sees this and we’re all expelled!”
Silver Spoon looked at her crossly. “Gag him with what?”
Groaning at having to alter her pace, Diamond shifted her leg in order to place her spats in Silver’s reach. “Hurry! He’s getting louder.”
The rubber-endowed woman wasted no time pulling the underwear from her friend’s ankle and shoving it into the howling man’s mouth. Button’s muffled screams grew in frequency and intensity as he gripped the counter with all his might, his arousal doubled by a fresh dose of Diamond Tiara’s intoxicating vaginal fluids. If only Silver Spoon would—
She thrust hard into his ass, hilting the dildo in him. She released his hips and tail, and quickly screamed into her arm as her climax washed over her, soaking the harness and the borrowed boxers with loosed femme ejaculate before slumping onto his back. At the same time, Button grunted, thrusting his hips back against hers, bashing his battered prostate with the gray rubber bludgeon—just one last time. He all but screamed into his makeshift gag as his balls clenched and he let loose strand upon strand of thick semen, coating his panties and thighs.
Diamond Tiara’s voyeuristic climax wasn’t far off. Watching her friend climax with the help of their new toy, she fingered herself furiously while tweaking her small clitoris with her other hand. Stuffing her juice-laden fingers into her mouth, she tugged her clitoris one last time, spraying both individuals before her with a shower of femme-cum.
The three students lay there, ears twitching and breathing heavily, basking in the afterglow of the fun they shared. Eventually, the pink one regained enough of her senses to reclaim her spats from the poor guy’s mouth. If it bothered her that they were all soaked with her fluids and his saliva, she didn’t make any complaint about it. “Wasn’t that fun?” she asked, tracing one juice-covered finger down his cheek.
He could only nod weakly, nuzzling against the finger and smearing more juices on his fur. “Y-yeah...”
“That was pretty fun, but I think I’m going to need to get a new outfit,” Silver Spoon complained, slowly withdrawing the dildo from Button’s gaping anus. “He may be small, but he sure cums like a horse.”
Button shakily stood up, lifting the front of the skirt to reveal his cum-soaked thighs and panties. “W-wow,” he gasped. “I did that?”
“What do you say we take our new toy back to the dorm and play some more? We’ll just call in sick!” Diamond asked mischievously. “I’m sure she would like to play more dress-up.”
Button frowned, suddenly remembering how he got into this whole situation. “What about Snips and Snails?” he asked. “They’re just going to beat me up some more, especially if I look like this.”
“They know better than to fuck with our toys,” Diamond scoffed, wiping his face off with a moist towelette from her purse before reapplying the make-up she’d painstakingly applied before. “You’re too much fun to be wasted on them.”
“Yeah,” Silver Spoon whispered, coming up behind Button and pulling the cum soaked panties all the way up. “You can keep these, by the way.” She winked seductively, licking some loose cum from her fingers. After helping him wipe up the cum on his legs as best they could, she pushed him toward the door. “We can work out a payment plan if you want to girl it up some more on your own time. If you want, we could even arrange dates for you.”
“That sounds...” Button gasped and ran back to the stall. “My Joy Boy! I nearly forgot it.”
The two women shared a look before watching Button bend over in his cum-soaked panties. “Oh we’ll definitely teach you the joys of boys.”