The sissification of Button Mash

by Cloper69

Rating: mature
Tags: My Little Pony: Friendship is Magic, Button Mash, Fetish, Other, Porn, Sex, Non-consensual, Big Macintosh
Length: 2645

Button Mash's Mom comes home to find her son wearing her panties. She decides to teach him a lesson about cross dressing. But she'll need some help....

When Button Mash's mom catches her son wearing her underwear, she decides to teach him a lesson, with the help of a certain big, red, farm pony. "You want to dress like a mare? Then you're going to have to fuck like a mare!"

Warnings:
Chapter 1: Dergrating, gay sex, incest
2)more incest, impregnation

Published 2018-05-13 21:00:06 UTC
Last updated 2018-05-15 03:02:46 UTC

A sissy is born

Love tap closed the front door quietly. She was off early today, and she wanted to surprise her son.

She looked all over the house, but he couldn't be found. Finally, she came to her bedroom. It was odd that he would be in here, but it was the only place left. She opened the door.

"Button, I'm home er- OH MY FAUST!!!"

There, on the bed, panic quickly taking hold of his face, was her son. He was masturbating. In a pair of her best neon green lingerie panties. As in he was wearing them. She gasped.

"Mom, it's not what you think!" he shouted.

A devious plan suddenly cut through her anger. She smiled a false smile.

"Of course. You just wanted to know what it felt like to be a mare!"

There was something in her tone that Button didn't like, but he played along, seeing a possible way out.

"Yeah, that's what it was. And now that I have..." He began to take off the panties, but his mom stoped him.

"No, dear, you need the full effect. Now give mommy a few minutes to make a call, and I'll be back to give you the full make over."

As she left the room, Button sighed. This was going to be torture, but it was better than the grounding he had probably just dodged...

30 minutes later

Button looked in the mirror, and he had to admit, he looked good. He certainly made a convincing mare, the only give aways being his mane and the bulge in the panties. His mom had him in the nightie and socks that went with the panties, along with matching green lipstick. She was dressed similarly, but in pink. He had a hard time trying not to get an erection just looking at her.

The door bell rang.

"Go to my bedroom sweetie. I'll be back in a moment."

Not wanting to be seen by whoever it was at the door, he obeyed. He sat on the bed and waited.

A few minutes later, the door opened. To his dismay it was not only his mother, but also Big Mac.

"Uhhh, mom, why is he here?"

"I decided that, if you wanted to know what it felt like to be a mare, you were going to know what it felt like to get fucked like a mare!"

He gasped, but he was frozen with fear. Yet there was still something arousing about this...

His penis popped out of its fabric confines, growing steadily.

"We can't have any of that, now."

His mom pulled a scrunchie from out of a drawer on the nightstand, and, folding it over once, put it around the base of his penis.

The pain was instant, if minor. Yet each pulse that tried to inflate his flaccid stallion hood only brought a wave of greater pain.

"Now," came Big Mac's deep voice, "let's get to it ladies."

Button, still frozen in shock, watched as Big Mac sat on the bed, haunches splayed, and his mom started to lick his growing erection. Big Mac looked at him.

"Ah meant you, too."

As if in a dream, Button, realizing there was probably no way out of this, slowly approached the big, red stallion, who further splayed to make room for the new arrival. Button stared at the growing penis.

A slightly darker red than the rest of him, it, at half erection, was already far bigger than Button's was at full. Button's nostrils filled with a powerful musk from him, and a less powerful yet equally maddening scent from his mother. His cock strained painfully against it's restraint.

"Well, filly, are yah gonna stare at it, or are yah gonna taste it?"

Still in a dream like state, he got down and stuck his tongue to it. It's taste was nothing like he expected. It was savory, salty. It had a hint of sweat to it from it's owner's hard work, but it was faint. Big mac had probably showered before he came here. And that musk was just so, so, arousing.

As he began to lick, part of him screamed that this was wrong. Another part, however, quickly overtook. It reasoned that this was only right. After all, Big Mac clearly was the better stallion. Surely this meant that Button was meant to pleasure him.

His train of thought was broken by his mom's hoof pushing him away. He looked up to see her lips close around the end of the cock. Her watched as she took a deep breath, and lowered her mouth, her throat bulging out as the massive cock slid down it. She gagged, and quickly pulled up, leaving pink streaks, until only the tip was left in her mouth. After a moment, she repeated the action.

Big Mac looked at him. "Hey filly! While your mom's busy with that, why don't you play with my balls."

Slowly, Button laid down on the bed, inadvertently sticking his nose to one of the tennis ball sized testicles. His sinuses were filled with the intoxicating musk.

Slowly, his body trembling, he leaned forward, planting a kiss on the warm ball. He pulled back, smiling at the green lipstick mark he had left. It was his mark, his claim on this hansom, sexually superior stallion.

He leaned in, this time sucking on it. Then he licked. He continued kissing, sucking, licking, covering that testicle in his green mark. It felt right.

His mom reached the base of the thick cock, then sat back, letting it come out of her mouth.

After catching her breath, she looked at Button.

"Ready, sweetie."

By now, any inhibitions had faded. He was lost in his arousal.

"Yes."

He sat up as she laid down, going after the testicle he had left alone. He looked at the massive dick in front of him. It was nearly two feet long, precum bubbling from the end, pink streaks from his mom's lipstick. He smiled, ready to leave his own.

He took the tip in his mouth, moaning at the taste of the pre. It was like the liquid embodiment of the musk he had been smelling. It was wonderful.

He pushed his head down, the tip rubbing the back of his throat. He gagged, and began to pull up. As much as he wanted it too, it simply wasn't going to work...

He felt a hoof touch the back of his head, and before he could react, it pushed him further down, to the medial ring. He moaned again. This was the best sensation he had ever felt. His throat stretched by this massive penetration. The hoof left his head, probably to let him get some air, but he didn't want air right now. He wanted more!

He pushed his head farther down, eyes tearing up at the lack of air. His lungs screamed for air, but everything else cheered him on. He loved this sensation, and wanted it to go on forever.

As he reached the base, he puckered his lips, leaving a nice, big smooch mark around the shaft. He was claiming this cock as his own.

He heard Big Mac and his mother gasp at the same time.

"S...sweetie! Look at your flank!"

He pulled himself up and off of Big Mac's cock, and pulled down his panties. There, on his flank, was a neon green kiss mark!

"Oh my faust! My cutie mark!"

The next few minutes were filled with tears of joy. Once mother and son had settled down, Big Mac spoke up.

"So, are yah ready for round two?"

"What's round two?"

His mother smiled deviously. "You'll see."

As Big Mac got up and moved behind him, his mom bent him over so that his ass was up in the air. It didn't take Button long to figure out what was going on.

"Uhh, mom, are you sure he'll fit?"

"Yes, sweetie. Just relax. It'll hurt at first, but you'll enjoy it."

"Are you sure?"

"Yes. Your dad did. When we lived in Canterlot, we went to this night club up town. We'd always bring a stallion back, and your father loved to get topped first."

"Ew, mom! TMI!"

She smiled, putting a hoof down her panties.

Button felt something rub against his little dick, cause a new series of painful pulses.

"Quite a clit yah got here, little filly. Way too small to be a cock, though."

Button felt that he was right. Big Mac was easily four times his size. He deserved to be the bottom. He felt Big Mac's superior cock rub up against his own as it drew back.

"Yah ready, little filly."

"Yes!"

His eyes went wide as his virgin anus stretched around this massive intrusion. It felt big enough in his throat. Now it was huge! He screamed half in pain. It was TOO big!

He felt Big Mac push, barely making any difference.

"Damn! You're tight!"

As he began to thrust, Button's muscles began to relax. It became less painful and more of a feeling of fullness. He moaned again.

His mom looked at him. "I guess you're just as much of a slut for anal as your dad was. I wonder, though..." She looked down at her soaked panties.

She lowered them, and a wave of scent hit him. Where as Big Mac's scent made him want to suck and be fucked, this made him want to mount her and fuck her until he filled her with his seed, until he had put a foal in her womb.

He shook his head. He couldn't possibly do that. That would be incest, which was wrong. Of course, so was what he was already doing.

She spread, revealing her glistening pussy. She scooted closer, where he could reach it with his tongue.

"Come on, baby, I know you want to taste the place you came from."

He gave an experimental lick. The taste was the opposite of Big Mac's pre, yet just as good. He felt her shudder from the sensation.

"Yeah, like that!"

He began exploring her pussy, licking her folds and her love tunnel it self. However, he got the best reaction out of licking her clit, so that's where he settled.

Button squealed as Big Mac pushed his medial ring in. He was only half in!

Button began thrusting back, pushing himself further on to the shaft. He moaned, his prostate stretched by this massive penetration.

His mom pulled away. He looked up to see her turn around, facing him, and flipping on her back, wriggling her way up under him. He felt the scrunchie release, his cock rushing to full erection. Then he felt her tongue.

He leaned forward and resumed licking her clit as she began to suck his cock. It was all so much at once.

He felt Big Mac's balls slap his own, and realized that he had finally reached the base. Big Mac now began to thrust faster, his flare forming and making Button moan. Button began to thrust into his mom's throat, and began sucking on he clit, making he moan around his cock. He felt a pressure building behind his balls, and he knew what came next.

All three of them climaxed at the same time. Button shot a load down his mother's throat as she squealed, spraying him in the face with her femcum. He felt a hot stream of cum begin to fill his insides, causing his belly to bloat. There was just so much of it, and it was so warm!

After a few minutes, Big Mac pulled out, unleashing a stream of cum on to Button's mom's face. Button collapsed, exhausted, and drifted off to sleep.

His mom smiled and rolled him off of herself. "Guess he couldn't handle all this excitement, ehh Big Mac."

When she got no answer, she turned over to see the great red stallion sound asleep. She sighed.

"Typical colts. Either fucking or sound asleep."

She yawned. It had been a long day. She deserved a nap. She closed her eyes, and all three slept as the sun set and night came to equestria...

Author's Note

Happy Mother's Day!

Button fulfills a fantasy

Button stretched in the bed. That was one heck of a dream he just had.

He looked over at the alarm clock. It was 3 a.m. Odd. He normally didn't wake up at this hour. And wait, that wasn't his alarm clock!

He got up out of bed, and looked at his flank. There, where it had appeared just a few hours earlier, was a large, neon green kiss mark.

So it hadn't been a dream!

Not knowing what else to do, he crawled back in bed, laying on his back. As he did so, he bumped in to his mother, who woke up.

She stretched and yawned. "So, sweetie, did you enjoy your first time with a stallion?"

"Yeah."

"Well..." she suddenly stood over him, so that they were nose to nose. "How would you like to try a mare?"

Before he could answer her, she leaned in and began to kiss him. It wasn't like how she had kissed him on the cheek when he was younger. Her tongue twirled in his mouth, entwining with his. He felt passion, not that of a mother, but that of a lover.

His cock began to grow. Before long it brushed against her pussy. He felt her moist, hot foal maker, and it took all that he had just to not thrust in to her, break into wild abandon and pound his mom's pussy. But he would resist that urge. He couldn't give in. He would never forgive himself. It would be a sin too far.

He may not have wanted to fuck her, but his mom had other plans. Feeling her son's cock rub against her entrance decided it. She had to feel him inside of her. She threw herself back onto his cock.

Button let out a loud moan. This was far better than he had ever imagined. Her warm, tight love canal wrapped around his cock, it was too much.

His mom began moving up and down, clenching her muscles with practiced precision, nudging her son to full erection. As he reached this, he began to thrust with her. Screw wether this was wrong or not. He was going to fuck his mother!

She sat up so as to take him deeper. She moaned as he pushed against her cervix. It had been ten years, since her husband had died, infact, since a stallion had been there. And now her son, whom she had fantasized about so many nights, was inside her. The thought made her want to cum right then.

Button moaned as his mother rode his cock. Never before had he penetrated a mare, and now it was his mom, the subject of many a perverse fantasy, that was ridding him. He was lost in ecstasy.

His mom picked up the pace, and both knew it wouldn't be long before they orgasmed. Sure enough, after a few more minutes, his mom slammed down, squealing as she came. This sent Button over the edge, blowing a load directly into his mother's womb.

His mom smiled in bliss. She had forgotten what it felt like to have a stallion fill her with his seed. And, considering his size, it was a huge amount. She licked her lips, imaging how hung he would be as an adult.

Button sighed in bliss. The moment was perfect. One of his most perverse (and favorite) fantasies had just come true. Nothing could spoil it.

That's when his mom leaned in and whispered into his ear: "I'm not on any birth control."

He gasped.

"Yeah. You're gonna be a daddy!"