Button's Bi-Diellema

by Alphamon_Ouryuken

Rating: mature
Tags: Snails, Button Mash, Sex, Sweetie Belle, Cake Twins, My Little Pony: Friendship is Magic, Romance
Length: 3978

Button goes to a few friends for advice on getting Sweetie Belle's affection... but their methods are the last thing he'd expect...

Foalcon 2017 Contest Entry

Sweetie Belle has always been the target of Button Mash's affections, however she seems to prefer more sensitive colts. So the young colt finds assistance in the form of Glitter Shell & Pound Cake who offer to help him get more in touch with their 'feminine' side, however he soon finds out they prefer a more 'hooves on' approach...

Co-written off-site with Vault Resident

Triggers: Foalcon, Yaoi, and Crossdressing. You have been warned!

Note: Pound Cake and Pumpkin Cake are the same age as the CMC in this story.

Published 2017-01-02 13:30:01 UTC
Last updated 2017-01-02 13:30:01 UTC

Pounding My Buttons

Button knocked on Snails' door, smiling nervously. He'd had a crush on Sweetie belle for the longest time, however he had doubts that she'd ever be interested in a colt like him... at least he did until Rumble told him that Sweetie was interested in colts that were more sensitive and sweet, so he was gonna learn to be sensitive and sweet! He was petty surprised that Rumble suggested he go to Snails and Pound Cake of all ponies, but Rumble assured him that they were surprisingly knowledgeable about these sorts of things.

So, earlier that week, Button asked them for help and, after a second of them looking at each other, they agreed.

So, here he was, standing on Snails’ stoop, excited to learn about caring and emotions and all that filly stuff.

Pound Cake opened the door and smiled upon seeing the Earth Pony. "Ah, Button! Right on time! Please, come in!" He said as he lead him inside.

Button flashed a grin as he trotted into his friend's home. "Hey there Pound, so where’s Snails?"

"Snails is upstairs getting ready for our-ahem-'lesson'…” Pound explained, closing the door behind him. “I have to say though, I'm kinda surprised that you came us of all ponies..."

"Oh, well, I thought over who were the most sensitive stallions I knew, and you two came to mind! So, yeah, here I am!" He looked up the stairs. "So, how much prep is he gonna need?"

"Oh, it takes some time to become comfortable with your more… sensitive aspects…" Pound explained as they walked upstairs. "I was already more comfortable with my life, but it took Snails about a week before he finally came out..."

"Came out?" Button asked, cocking his head slightly in confusion, trotting alongside Pound. "I'm not quite following you here."

"Why, coming out of the closet of course." Pound said as he opened the door, revealing Snails wearing a see-through lingerie and makeup. "Glitter Shell, out guest has arrived!"

"T-the closet?" He mumbled before seeing the cross-dressed colt, a bright red blush formed over his cheeks and his jaw hung open like a fish. He tried to tell them he made a mistake, but all that came out was "I-I, uh, m-m, ah..."

"Oh hi Button!" Snails said in a surprisingly feminine tone, one that wouldn't be out of place coming from Silver Spoon. "I'm so glad you could make it!"

"Sna-I mean, Glitter, I think I made a mistake here..." He finally spat out, before letting out a small 'eep' as Glitter levitated him into the room as Pound Cake locked the door.

"Relax Button, you came because you needed help." Glitter Shell said as she lowered him onto the bed. "If you bail out now, we won't be able to help you."

"She's right you know..." Pound Cake agreed as he crawled onto the bed, now wearing his own makeup, his face now completely white with red dots on his cheeks. "We're both comfortable with the way we carry ourselves. And if you want be more sensitive you need to do the same.”

Button opened his mouth to reply, but thought for a moment. ’They kinda have a point.’ He thought as he shifted nervously on Glitter's bed. "Y-yeah, I guess you're right..." He said, looking from Pound to Glitter. He hadn't thought too much on it before, but it really was incredible just how well Glitter could pass for a filly. Guy was really, really good at this, it seemed.

"Now first things first..." Glitter Shell began as she gently stroked his mane. "I noticed you tend to stutter when chatting with Sweetie Belle. What seems to trouble you?"

A light blush shiver went down his back at Glitter's touch, and Button scooted back. "Well, it's just that she's so cute and… and I'm scared that I'm gonna mess up and make her think I'm a loser or a dork or something..."

"Now let me ask you, is that her talking, or you?" Pound asked as he put his wing over his back, prompting him to twitch a little at the light touch of Pound's feathers. "You really need to feel more comfortable with yourself. Doubt like that will just torpedo your self-confidence, and we can help you with that..."

He nodded as Pound spoke, recognizing that Pound was right. "Y-you can?"

"Of course, but first we're going to have to ask you two special questions…" Pound explained. "And then we move onto making you more... sensitive..."

"First question: How much do you love Sweetie Belle?" Glitter asked.

"A-A lot! She's so cute, a-and whenever we talk sh-she's usually pretty nice..." Button answered, shifting a bit.

"Good. Second question... what if she'd been born different?" Glitter asked. "What if she was born as a Colt? Would you still love her?"

"Uhm... N-no, I only like f-fillies..." He mumbled, unsure of his answer, his cheeks utterly flushed.

"Oh? But didn't you just say you genuinely love her?" Pound asked curiously. "If that's the case then why would it matter if she was a colt?"

"I mean, th-that'd be gay and... and..." He was looking down at his hooves which he was rubbing together nervously, his next words were barely a whisper. "I'm not gay…"

"And why should that matter?" Glitter asked seriously. "Are you say that if you were dating her and by some magical mishap she ends up turned into a colt... would you really be so cruel as to abandon her? Just because of a trivial issue regarding gender?"

"Button, this is what it means to be sensitive." Pound explained in a softer tone. "Suppose the exact opposite happened and you were turned into a filly, would it be fair for her to simply dump you just because she wasn't a lesbian?"

"I dunno, I've never thought of anything like this..." He put his hooves on his temples, looking pretty stressed out. "I... I think, if she was still, you know, Sweetie, I'd still like her, even if she was a colt."

"Is that so?" Glitter asked as she got right in front of him, her nose inches away from his own. "Well then, I have believe it's time you proved it..."

Pound smirked. "Yes Button, you know what they say: actions speak louder than words…"

Button leaned back as Glitter got close, but the wall stopped him from going too far. "H-how do I d-do that...?" He asked, slowly.

"It's simple... first you close your eyes... and imagine Sweetie Belle right in front of you..." Pound explained, giving Glitter a subtle wink

"Uhm, alright..." Button said, shutting his eyes and straightening up. His lips flick into a smile as he pictures Sweetie Belle sitting in front of him.

"Now… I want you to imagine her about to give you the most passionate kiss you've ever felt…" Pound whispered gently as Glitter got closer…

"Oh, uh, alright..." He mumbled with a bright blush, imagining the crusader pucker her lips slightly puckered. He puckered his own in response, and briefly considered maybe he was a little too good at imagining; he could almost feel her breath on his muzzle!

"Now, I want you to imagine her as a colt." Pound said as he felt him tense up, he gave his a gentle stroke with his wing. "Don't let that bother you, relax your body and remember one thing: gender does not matter, it's still the same pony you've fallen for, and if you truly love her, simply trust your feelings and let it happen..."

"A-alright..." He said, shifting on the bed but keeping his eyes closed. "I guess that's not too hard..." He said, his brow clenching slightly as he edited his mental picture. Once he had properly imagined his colt-Sweetie, he resumed his almost-kissing face.

Upon seeing him relax, Glitter leaned forward and kissed him on the lips. She wrapped her hooves around him and pulled him closer.

"Now let go of all those mental restrictions you're built up, gender doesn't matter when it comes to love..." Pound whispered into his ear seductively.

"Mmm?" A muffled sound came from his muzzle when Button felt contact with his lips. For a lone moment, he just thought he was still imagining. But then sense took him and he opened his eyes, and he let out a loud "Mmph!" Button was beat red with blush and he pulled back. "What are you doing!?" He cried, panicking.

"Helping you..." Pound whispered as Glitter held him still with her magic. "Like I said, you need to let go of your limitations..."

Glitter then pressed her nose against Button's. "If you keep letting the differences between genders get in the way of your feelings, you won't make any progress..."

Button struggled against Glitter's magic, but it was a wasted endeavor. "Th-that's not the problem! Th-that was my first kiss, I didn't know you were gonna kiss me!" He whined.

"You said you wanted our help." Pound said as he trotted around him. "And the fact is that you're not ready to act on your feelings."

"Not to mention you're kissing skills need work…" Glitter smirked, affectionately stroking his cheek. "It doesn't matter if it's your first kiss, it's the first kiss you give to her that matters. Would you rather give her a sloppy first kiss, or an experienced kiss that shows just how much you love her?"

"I-I... I guess you're right..." He sighed, looking down at his hooves. "If you think this'll help me with Sweetie, I'll... try and be more cooperative..." He mumbled, bringing his eyes up to the pair.

"Good... now, close your eyes and relax..." Pound cooed, wrapping his wings around Button as Glitter's aura dissipated. "Imagine Sweetie Belle, as a colt, ready to kiss you..."

Button closed his eyes and takes a deep breath to calm his nerves. Then, he brought back his mental image of Sweetie, as cute as a colt as she is as filly. He puckered up his lips as he imagined Sweetie-colt leaning in, Glitter leaned into the kiss again, only feeling a small amount of resistance this time. Pleased with this result, she opened her mouth slightly and gently pressed her tongue against his lips.

"Now comes the kissing improvement." Pound whispered into his ear. "Open your mouth a little..."

Button's cheeks flushed again, but he went along with Pound's command, slightly opening his mouth. All the while, he kept thinking of Sweetie. He reached up to brush some of the imaginary stallion's mane out of his face and ended up lightly stroking Glitter's cheek. "Oh? Becoming quite the charmer, are you?" Pound giggled as he gave Button a small peck on the cheek. "Well now, it's time to really get into it. Pretend Sweetie has small piece of hard candy in her mouth, and she's trying to share it with you..." Pound explained as he continued to stroke his back. "Stick your tongue into his mouth... pretend you're trying to take the candy from his tongue..."

Button slowly slid his tongue into her mouth, swirling around Glitter's tongue. Something like a whimper came from Button, who was starting to realize that he really, really liked kissing. Pound playfully nibbled his ear. "Now keep licking, keep kissing him..." As he continued to whisper, his hoof moved down towards his crotch area, rubbing it gently. "Remember, gender doesn't matter, only your love for the pony before you..."

Glitter moaned into the kiss as she played with his tongue, noticing where Pound's hoof was going and moved to rub him there as well. Button felt their hooves traveling towards his colthood, which at this point was utterly erect and pressing against his own soft underside, as equine erections were prone to do, and part of him knew he should pull away and leave. But that part couldn't convince the rest of him, which was under the sway of the moment. He wrapped a foreleg around Glimmer and pulled her closer against him.

After a moment, Glitter broke the kiss. "Now for the fun part..." She giggled as she leaned down towards his throbbing member while Pound gently pushed him onto his back, quickly taking Glitters place and kissing him just as passionately. Button happily got to sucking face with Pound, wrapping a foreleg around him and putting a hoof on his flank. Glitter meanwhile observed his stallion-hood, impressed by it's length, and gave it a long lick from the base, all the way up to the tip. Button shuddered and moaned into the kiss as Glitter's tongue made contact with his member. All this was making Button's heart was pounding hard in his chest, and he absolutely loved it.

"Finally getting into the spirit of things are you?" Pound giggled as he broke the kiss, batting his eyes seductively. "Well then, why don't we skip ahead a little?" Glitter giggled as she started sucking on his balls, taking them both into her mouth and fondling them with her tongue.

Button bites his lip, glancing down towards Glitter, and starting to lightly pet her mane with his hoof. Looking back up to Pound, he nods. "Y-yeah man, whatever you want..." He mumbled, somewhat nervous still.

"Well then... suppose Sweetie Belle wants to try something more... "kinky" with a strap on, you'll have to lube her up..." Pound smirked as he straddled Button, his own erect cock inches from his mouth. "You've come this far... why not keep going?"

Glitter, having teased his cock enough, happy took its entire length into her mouth, eagerly deepthroating it right to the base.

"Ooh..." Button moaned, hind legs wrapping around Glitter's head. He looked to Pound. "Y-yeah... So what would I-Ah~!- do that?"

"Suck on it like a Popsicle." Pound commanded before pressing the tip against his lips while Glitter started bobbing her head up and down his shaft, lubing it up with her saliva. "Lick and suck on every inch like Glitter is."

Button nodded opened his mouth and lowered it around Pound's flare, licking and swirling his tongue around there, before slowly moving his head down his length. "Mmmm~, good boy~." Pound moaned out, slowly pushing his cock deeper into his mouth. "Lick every inch~"

Glitter sighed contently as she pulled his cock out of her mouth and positioned her ass right above it. "Now for the real fun..." Meanwhile Button, slowly but surely brought his head lower and lower down on Pound's cock. Eventually, hips lips were pressing against the flesh around Pound's hilt. Button ground his cock against Glitter's tight rump, before pushing against his tight tailhole. Pound slowly pulled his cock out until only the tip was still inside, and then shoved it back inside, enjoying the sensation of Button's tongue wrapping around his cock he happily repeated the motion, thrusting in and out of his mouth.

Not wanting to wait any longer, Glitter pushed his ass down onto Buttons stallionhood, letting out a blissful moan in the process. "Oh sweet Celestia yes~!!" Button moaned into Pound's cock, sending vibrations throughout his colthood. Button did his best to keep up with the Pegasus' cock, but sometimes he would gag on the returning cock. Button started fucking Glitter in short thrusts, rutting him like a dog.

"Mmm, yeah!" Pound giggled in pleasure as his eyes rolled to back of his head. "That’s it big boy! Suck me off! Dear Celestia I'm getting close!!" Pound grunted as he held his head in place, the feeling of sweet release mere thrusts away, as he felt his tongue eagerly wrapped around his stallion-hood, he gave one final thrust, pouring his load into his mouth. "Swallow it! Swallow it all!!"

"Yes! Yes! Yes! YES!!!" Glitter screamed as she bounced up and down on his cock. "Oh mother of Celestia! Sweetie Belle's gonna be lucky to have you!" She giggled out in pleasure as her ass clenched around his as she let out one final moan right before she came, shooting her thick white cum all over Button's stomach and Pound's back. Button glugged down Pound's cum, letting out a loud moan as he reached his own climax, filling Glitter's rump with his hot seed. He made a slurping sound on Pound's cock as he pulled his head up and off his length. He gave Glitter and Pound a big, somewhat doofy smile.

"That was amazing..." Pound sighed as he rolled onto his back, basking in the afterglow. "Sweetie Belle is gonna love you..." He smiled, while Glitter pulled herself off his cock, his seed dripping out of her ass as she crawled on top of Button and gave him another kiss.

"Was it as good for you as it was for us?" She asked.

Button laughed, and gave Glitter a peck on her cheek. "Heh, yeah, that was awesome..." He looked over to Pound. "So, do you think I'm ready to get Sweetie to like me?"

"Well then, why don't you try asking her yourself?" Glitter giggled as the door to their room opened, revealing Sweetie Belle with a seductive grin on her face. "She's been watching the entire time."

"Speaking of which, how did you like the show?" Pound giggled as she entered the room. "I think he's a keeper!"

Button's face fell, he was horrifyingly embarrassed. His cheeks were beet red, and fell down on to the bed, covering his head with one of Glitter's pillows.

"Quite the stunning display, I must admit!" Sweetie giggled as she jumped onto the bed and pushed the pillow out of the way. "So Button, do you have something to tell me~?" She asked, her lips inches away from his own.

Button gulped and looked up at Sweetie with scared, wide, eyes. "I-I l-like you..." He mumbled.

Sweetie got closer, to the point where he could feel her breath on his lips. "How much do you "like" me?" She asked as she used her magic to grab hold of his stallionhood.

As her magic enveloped his hardening stallionhood, Button let out a little 'eep'. "I-I like you a l-lot... I l-"like” like you..."

Pound sighed as he gave his neck playful lick from the left. "Now now Button, be honest with her…"

"Yeah, after everything you've just gone through, you can't back out now…" Glitter giggled as she nibbled his right ear.

Sweetie proceeded to press her lips right up against his, not at outright kissing him, but practically in inviting him to do so. "Tell me Button, how much do you like me?" She asked again as she started stroking harder.

"I-I love you! You're the most wonderful pony I've ever met and I would do anything to be your coltfriend!" Button blurted, before wrapping a foreleg around her neck and pulling her down onto him, locking lips.

Sweetie Belle happily kissed him back as she continued to stroke his cock. 'Mmm... Glitter's advice really paid off, he's a real good kisser now!' She mentally giggled as she wrestled with his tongue.

"Awwww... you two are so cute together!" Glitter giggled as she stroked her own cock watching the two make out.

Pound however, pulled what appeared to be a bottle of lube out from under his bed. "Now comes the real test..." He giggled as Sweetie broke the kiss.

"Tell me Button, would you love me..." She paused as she sat up, revealing her own colthood. "Even if I was a colt?"

While a day earlier, such a question would've caused Button to really think some stuff over, now he just nodded with a grin. "Of course!" He said, with vim and vigor.

"Exactly what I wanted to hear!" Sweetie Belle smiled widely as she spread Buttons legs and levitated the lube out of Pound's hooves, she then proceeded to pour some out and gently levitated it towards his ass, she guided it inside his hole, making sure to get both the inside and outside properly prepared. "Well then Button, are you ready to give your anal virginity to me?"

"Do you promise to be gentle?" He asked, with somewhat of a sheepish smile. He was hesitant, but willing.

Sweetie carefully positioned her cock right up against his asshole. "As gentle as Fluttershy handles a baby kitten." She reassured him, despite being very eager to pound his ass.

Meanwhile Glitter and Pound decided to make themselves scarce, leaving the two lovebirds alone…

Button looked up at Sweetie with a soft smile. "Do you want me on my back, or on my stomach?" He asked, flicking his tail out of the way of his virgin plothole.

"Stay on your back, I want to see your goofy face when you cum!" She giggled as she slowly pushed her cock into his ass, sliding in nicely thanks to the lube. "Mmm~ so tight... so smooth~"

Button's lips tightened when she entered him, and he started taking deep breaths to relax. "G-gosh..."

"That's it Button..." Sweetie grunted as she slowly pushed herself deeper inside. "Don't fight the feeling, just let it happen…" She cooed as she continued to push, letting out a cute moan every so often.

When she finally pushed herself to a hilt inside him, his cock's head started to dribble pre onto his soft underbelly. "Y-you make me feel so full..." He mumbled, with a smile.

"Oh Button~" She moaned as she slowly pulled back out, only to push back in slightly faster. "You complete me~" She sighed as she started thrusting.

"Ah...unf...!" Button started to grunt as Sweetie took him from behind, the colt moving his hips slightly back against hers with each thrust. "R-rub me, p-please..." He panted, taking her hoof and moving it to his leaking cock.

"I got a-umf-better idea!" She grunted as her horn glowed, enveloping his cock. The aura twisted and distorted before bobbing up and down on his cock, mimicking the feeling of a mare's actual pussy. "You-ah-like that, love?" She asked as she started thrusting faster.

"Oh, oh yes, yes!" He moaned, thrusting up into the arcane aura. "You're the be~est!" He moaned.

"And you're-ugh-amazing!" She giggled, thrusting harder as she gazed into his eyes. "I must-oh-confess, I've had my-ahn-eye on you-ohhh~-since the day I m-moved to P-Ponyville!" She gasped, the feeling of sweet release welling up within her.

"C-cum inside me!" He moaned, pushing his bottom down on her cock. "F-fill me with your f-fillycum!" He said, before her magic finished him off, shooting his own seed.

"Get ready Button!" Sweetie groaned as she Button's cum shot all over her face while she continued to thrust. "I'm gonna turn you into my personal cum-dumpster!!" She screamed right before giving him one final thrust as she poured her load inside him, not stopping until his ass was practically overflowing with cum.

Button clenched up when she started cumming, doing his best to keep all her seed inside him. "Yes, Sweetie, yes, fuck me!"

Sweetie let out one final lust-filled moan as she stopped cumming, lying down on top of her lover and basking in the afterglow, not caring if her face was still covered in his seed. "That... was... amazing..." She panted.

"Y-yeah..." He said, starting to absentmindedly stroke his hoof through her mane.

Sweetie gave him an affectionate nuzzle as casually levitated Button's cum off her face and into her mouth. "I'm such a pervert... I seriously came a few times watching you do it with Pound and Glitter..." She giggled before swallowing.

He wrapped his forelegs around her neck and gave Sweetie an Eskimo kiss. "Gosh, I never knew you were such a voyeur." He giggled. "So, we're coltfriend-fillyfriend now, right?"

"Damn right we are!" Sweetie giggled, giving Button a peck on the nose before whispering into his ear. "However, I'm not opposed to an open relationship…"

"I mean, as long as you're in it, I'm happy." He nuzzled her cheek.