Trick, Treat, or Milf

Chapters

Cookie
Rarity
Sweetie
Bonus: Cockholding

Cookie

Nightmare Night rolled in with its familiar crisp air and vibrant autumn colors, the small town of Ponyville buzzed with excitement. Children donned their favorite costumes, ready to embrace the age-old tradition of trick-or-treating. Despite reaching college age, Sweetie Belle was enthusiastically collecting candy. Running from house to house, enjoying the labor of a heavy bag of treats. Normally she wouldn't be alone, but this year she was. Far away from her spot, her second half, Button Mash was grappling with a new plan this year.

Now that he had shed the last remnants of childhood, Button Mash felt he had outgrown the simple pleasures of trick-or-treating. "I've got to be more selective," he mused, watching Sweetie Belle sprint further and further from his sight. What once felt like the highlight of the year now felt a bit juvenile. Once she was out of sight, Button's gaze drifted through the streets crowded with costumed friends to a house that stood slightly apart. His true target was none other than Sweetie Belle's former home, the simply cottage of Cookie Crumble, her mother.

Button couldn’t help but feel a rush of excitement. The mother of Sweetie Belle was well known for her large assortment of candies. However, while other young ponies were hunting for chocolate bars and gummies, Button had something different in mind. He decided that instead of chasing after candy, he would strike for a greater prize.

Armed with a light-hearted spirit and a dank idea in mind, Button made his way to the candy decorated home. The air was filled with the spicy scent of autumn leaves and the faint echo of laughter from fellow trick-or-treaters. As he knocked on the door, his heart raced. Would she appreciate his unique gift? Moments later, the door swung open to reveal Cookie Crumble, dressed in a stunning witch costume adorned with an elegant cape, and a witch's hat.

“Button!” she exclaimed, a warm smile spreading across her face. “What a delightful surprise and without my daughter?! Are you here to trick-or-treat?”

“Actually, no, I've planning something different this year." He chuckled nervously, holding up the basket tightly against his crotch. "I've decided to give you a snack this year." He gestured out his hand, hoping she would let him inside.

"A snack, you say? Well, thank you, Button!" Cookie smiled and led him inside.

The house was dimly lit, save for a few decorative lights that shone throughout the living room, accentuating the elegant yet spooky decorations. Button followed her, feeling his stomach flutter at the prospect of being so close to his crush's mom. Once he was passed the door, he quickly flicked off the porch light so they wouldn't be bothered and led the prime milf away from the windows. "I brought you a little something. I thought you might enjoy a snack that stands out from the rest.” He shook the basket, never removing it from his pants.

Cookie Crumble's eyes sparkled with intrigue as she looked into the basket, the aroma wafting toward her. It smelled rich, and salty, and sweet, but also a different smell she didn't recognize right away. As she dip down lower to the basket, Button got a full view of her large cleavage. With a corset that enhanced her already large bust and her nipples nearly protruding over the top, she was dressed as a witch.

"Specail... why are these snacks look no different from my own selection." Cookie Crumble exclaimed, spreading her hand over the top. She picked a single piece and examined it closely.

"Just dig a little deeper..." Button shivered as her breath blew over the basket. "Trust me, its in there.

She put her nose closer, and her nostrils flared as she breathed deep. Shrugging, she dove her hand in deep and began digging around, each second sending shivers and groan over Button's body as the fingers just barely kept missing the hardening prize growing in the basket. "I can't seem to find any--" Cookie's face went bright red, and a smile slowly grew out. "Oh... Oh my..." Her grip tightened, making the young stallion groan out. "Oh... I think I found it." The sexy milf giggled, moving her hand up and down. "What a big and heavy treat you've brought me..." Her eyes narrowed up at him. "You're lucky my husband isn't home."

"And its all for you..." He whimpered as her hand slid over his tip, teasing him.

Cookie Crumble pulled a hand full of cock free, her eyes wide in shock at the massive size. "How in Equestria are you keeping this thing contained?!"

Button groaned out, his cock pulsating in her hands. "It... its really hard to when you daughter is so dense."

"Sweetie Belle keeps turning this down." She licked her lips, her mouth watering. "How shameful can that young lady be?" Her tongue slipped over the tip. "A fine stud like yourself shouldn't go to waste."

Button's body trembled as he felt her tongue slide over the tip. "Yeah... Sweetie Belle can be so cruel." He let out a groan, his cock pulsing hard. "Maybe... Maybe you could do something to make me feel better?"

"Why, I thought you'd never ask." She smirked, taking another lick of his dick, her hand still working it up and down, dropping her head into the basket, her mouth taking his cock fully. Button gasped out as he felt the warmth of her mouth and swallowed him whole, the feeling of her tongue and teeth on his cock sending his mind racing.

"O-ohhh!" He gasped out, his hand grasping her mane. "This is amazing!" He moaned out, feeling his hips buck. "Best snack ever--" His words were cut off by a loud ringing from his phone. His eyes widened in fear, and he quickly pulled himself out, fumbling with the buttons on his phone. His eyes softened upon the name. "Rumble, what's going on?"

"I struck out with Diamond Tiara and Silver Spoon again!" Rumble growled, his voice crackling over the line. "They didn't fall for the classic dick in the basket trick."

"Oh, sorry to hear that, buddy." Button tried his best to sound sincere about his friend failing to catch what he was bluntly enjoying. "You could try a pizza box?!" He tried not to sound to hoarse given his position

"Are you okay?" Rumble asked, concern clear in his voice. "And who has pizza during Nightmare Night? The joke for this holiday is obvious!"

"Maybe they aren't in the mood yet." He grunted as Cookie took him back down her throat. "You just gotta wait for the right moment... then make your move." He could feel the milf sucking him off faster and faster.

"My hard on can't wait that long. I'll just go to Pinkie Pie. She'll eat anything covered in white frosting." Rumble grumbled, his voice sounding disappointed.

"Good luck, bud." Button moaned out, the feeling of his cock twitching in her mouth was overwhelming. "If not, try Spike's hot sister."

"Yeah... even if she does have a better rack and ass, I'm not desperate enough to rip her face away from a book..." Rumble sounded so defeated. "Tender Tap's so lucky to have such a loyal bitch like Apple Bloom... If only we both could find mares like that."

He stopped for a few moments, allowing Button to catch his breath and slowly lean over as the milf began gargling his shaft and kissing his balls. "Yeah... we have all the bad luck." He bit his lip and dug his fingers into the milf's mane. "Sweetie Belle left me... to get candy long before I could even make the suggestion."

"You, me and my brother all had shit luck with mares." Rumble sighed. "How things went better for Spike on his journey. Happy Nightmare Night!"

"Y-yeah." He gasped out, the sensation of Cookie's teeth lightly scraping over his cock was driving him insane. "Happy H-Nightmare Night."

He hung up and tossed his phone onto the couch, pulling out his cock, throwing away the basket and grabbed the milf's face. He smiled so proud at all the spit and drool falling out of her mouth. His eyes narrowed and his grin got bolder, puffing her cheeks and ramming his dick right back into the milf's throat, rough and hard. She let out a muffled scream, her body shaking with delight.

"This is what happens when you suck dick like a bitch!" Button laughed, feeling her nails dig into his thighs, her face pressed firmly against his crotch. His cock throbbed hard as her eyes rolled into the back of her head.

Cookie's tongue wiggled about, rubbing all over the underside of his cock. Her hands gripped him tight, trying her best to maintain some semblance of composure, but the stallion was not going anywhere. Her eyes widened, tears forming at the corner as he pushed his cock further down her throat, and she could feel her neck bulging outward.

Button's body trembled. His face was red and hot as he stared at the sexy milf choking on his cock, and he knew he was getting close. "Take it!" He shouted, his hips bucking, his cock pulsing. "Be a better bitch then your daughter ever was too me!" His hands grasped her ears, pulling her forward, forcing her to swallow his entire cock.

Cookie's eyes widened, her jaw trembling, as she felt the stallion's hot, sticky seed shoot down her throat, filling her stomach. She tried her best to swallow, but the sheer amount made it difficult, and soon, her cheeks were bulging with cum, her eyes rolling back. She gurgled and slobbered all over his shaft, unable to keep it all in.

He gasped, feeling his cock finally go soft. "That was... the best snack ever." He pulled himself out, his dick making a satisfying 'pop' as it came free.

Cookie Crumble fell against her table, her body shaking, her mouth gaping, her throat raw and sore. Her body was hot and wet, her hair matted to her head, her makeup running. She panted heavily, staring up at the ceiling, adjusting her corset.

Button sat down, catching his breath, a big smile on his face.

Cookie wiped her chin clean, then looked at her young friend. "Thank you for sharing this delicious snack, Button." Dragging her hands over her chest and body, down to her hips. "However, I don't think I have anything to give you in return..." With that her dress dropped and she flaunted her legs over his crotch.

"Oh no..." He gasped out, feeling her hot and sweaty pussy pressing against his still semi-hard cock.

"How about some entertainment instead?" Cookie leaned in close, kissing his cheek.

"I would like that." He nodded, his eyes glued to her massive breasts slowly popping out of the corset.

Cookie's smile grew and began dancing her pussy down his length, grinding and swiveling left and right. Button gasped, feeling his cock rise back to attention. He reached up and grabbed the milf's tits. His face was pressed against them, muffling his moans as the hot milf humped and grinded, his cock throbbing and pulsing.

Cookie's pussy was dripping, coating his shaft and balls. The warm fluid trickled down his legs, causing him to shiver. His cock twitched and throbbed, growing harder and harder. His breathing became labored and ragged, his heart pounding, his mind reeling. She leaned back, her ass now pressed firmly against his balls. His tip rubbed her pussy and she shuddered. "Oh Button... You're so thick." She cooed, her body quivering.

His body tensed, his toes curling, his fingers digging into the milf's plump flesh. Her tits jiggled and swayed, her hips gyrating, her pussy grinding over his length. Her walls clamping down on his shaft, squeezing him tightly. He dug his nails deep into her chest, causing her to squeal in pleasure. He closed his eyes and leaned back, loving every second.

Again, the phone rang.

"Damnit, who is it this time?!" Button snarled, his hand reaching out and picking the phone up. He clicked it on and heard the heavy breathing and clear sounds of dance music. "Tender Tap..."

"Yeah, did Rumble just call you too?" the dancer panted out, his voice was muffled and distant.

"Yes, he did." Button answered, maintaining his breath. "He has his brother's bad luck."

"Nah... if it was that bad, Scootaloo wouldn't chasing him down tonight." Tender chuckled.

"How's your night going?" Button grunted, his hips bucking.

"Just having a lot of fun." Tender Tap laughed, his breathing labored too. "Apple Bloom passed out some candy... And then she... Damn she's such a good mare friend."

"Good for you." Button groaned out and rolled his eyes.

Tender's voice was strained, and the sounds of flesh hitting flesh echoed through the speaker. "Her pussy is so warm and soft. Her body is so tight and firm.. breasts so big... ass so..."

"Are you wanting me to jack off to you two!!" Button gritted his teeth and screamed into the phone.

"Just saying... Having a real mare is worth a thousand magazines." Tender Tap groaned, sounding disappointed somehow. "Happy Nightmare Night, bud. Talk to you later."

"Fuck you!" Button hanged up and tossed his phone aside. "Damn it..." His anger wasn't aimed at his friends, rather it was slowly channeling toward Sweetie Belle as he plowed her mom. He rose up and began fucking back into the milf with great force. "Stupid Sweetie Belle. I try so hard... and she just looks the other way. What's a stallion gotta do to get her attention?!" He growled, slamming his hips up, driving his cock deep into her womb, causing her to gasp.

"She is such a waste, isn't she?" Cookie Crumble cooed, grinding down, her ass smacking into his crotch, her walls squeezing him tight. "My daughters are such prudes... It's shameful."

"I've jizzed so many paper towels to that mare..." Button's hips bucked wildly. His body was burning up, his balls churning. His mind raced as his cock pulsed and throbbed. He felt the milf's pussy clamping down, her walls convulsing, her juices dripping down his shaft. "I want to fuck her so bad... I want her to be my mare..."

"Such a waste of a fine stallion." Cookie moaned out, her voice low and husky, her body trembling, her hips jerking. "She doesn't know what she's missing out on."

"It's so hard to hold myself back." Button gritted his teeth, feeling the edge rising. "Every time I see her... I just want to rip her clothes off and pound that pussy till it breaks." He leaned forward and wrapped his arms around her waist, pulling her in tight.

"Then do it." She whispered into his ear, her lips brushing against his skin. "I'll help you, baby." She kissed his cheek. "I'll show you what a real mare should do."

"Thank you, ma'am." He whimpered, his cock throbbing and pulsing. "Yeah... Let me give you some cum..." On that word, she climbed off his cock and let him stand up. Cookie bent down to her knees and opened her mouth. Her eyes closed as the young stallion began jacking off to the milf's sexy visage, her eyes, her mouth, her chest, and her cunt. Button groaned, his balls twitching and tightened up his cock flexed and spurted out his cum, covering her in a layer of hot, sticky white.

******

Author's Note

Button Mash is getting ladies all the way through till Day of the Dead. Up next is Rarity.

Rarity

Before Cookie Crumble could finish cleaning off his cock, Button took a few steps away from the couch, trying to catch his breath after busting two loads over the milf. He looked at the clock and saw he had been here for almost an hour. The thought of Sweetie Belle coming back from her hunt for candy made him nervous. He looked down and saw the mess he made, trying to quickly figure out a fast escape in case she walked inside.

"So..." Cookie Crumble cooed, licking the cum from her fingers and smiling seductively at him. "You wanna do anything else?" She stood there, a dazed look on her face as she licked the jizz off of her massive chest. Her body was covered in his seed, and she was panting hard.

"No, sorry, but I need to go home." Button replied, quickly grabbing his pants and attempting to adjust his shirt. However, without warning, both clothes vanished, leaving him completely naked in front of her. "H-hey! Give those back!"

"That wasn't me..." She giggled at all his nerdy muscles and body frame exposed. "Looks like a certain somepony wants you to stay a bit longer."

Button's head whipped around as his eyes narrowed. His ears flicked at the lustful breath behind him. The sound of footsteps coming closer and the feeling of a warm presence next to him. "Oh no..." He shivered in absolute terror at the possibility. Confusingly, a purple mane drifted over his shoulders, followed by arms that were clearly not Sweetie Belle, a large pair of breasts bouncing around his head.

"Mother, dear. You are so selfish," Rarity's voice echoed behind him. "To take such a cute and lovely young stallion, without inviting me!" She tilted him around to the visage of her own sexy costume, a pirate outfit with an open front for her cleavage, and a small cut-off skirt, showing her large ass, thighs, and long legs in black heeled boots. "And to think, I was generous enough to let you ride my Spikey on occasion. The least you could do is share."

"I'm so sorry, daughter." Cookie leaned back and let her daughter enjoy the snack. "You can have him next. He's very nice and polite." She licked her lips and climbed onto the couch to watch them work.

Rarity's eyes narrowed and her smile grew. "So... how about a little trick or treat, handsome?" She spun him against the wall and dropped down to her knees, pushing his cock into her cleavage.

Button let out a loud gasp, his body shivering. He felt her soft, smooth breasts engulf his shaft. The leather of her costume kept a tight grip on his member, the coolness of the material compared to the heat of her chest sending shivers up his spine. He watched her rub her boobs together, the sensation of her hard nipples poking into his dick caused him to buck his hips, his balls twitching.

Rarity giggled, her voice low and seductive, pressing her arms against the wall and trapping him in place. She slowly moved her chest up and down, her breasts squeezing his cock, and her body shivering against his balls, the soft texture of her skin and the warm heat of her body were driving him insane. Button closed his eyes, his breathing was ragged and uneven, and his face was red and hot from the sheer thought of both women alone. His mind reeled as her boobs continued to massage his shaft.

"You have such a big and juicy cock." Rarity cooed, her breath brushing against his skin "It's so thick and hard... I can't wait to have it inside my tight ass." She whispered, shaking her chest harder.

"Please... stop teasing me..." Button begged, his eyes watering, his heart racing. He felt his body tremble, his cock pulsing and throbbing, the pressure in his balls building up. Again, just like clockwork, the phone rang again. Luckily, this time, it was Rarity's phone, not his

"Oh my, that's Sweetie's ringtone." Rarity laughed, letting the phone ring for a bit and then picking it up and placing it between her shoulder and ear. "Hello dear, did you get a lot of candy tonight?" Her eyes narrowed, and her grin got bigger as her breasts went faster.

"Sister?! Have you seen Button Mash?" Sweetie shouted, the sounds of a party echoing in the background. "I've been looking everywhere for him!"

"Well, why yes, I have." Rarity's voice was calm and collected, though the sounds of her tits squelching over Button's wet and sloppy dick was obvious.

"What's that noise?" Sweetie pleaded, sounding so desperate. "Did I interrupt you and Spike again?"

"No, he's out trick-or-treating too." Rarity's tone was casual and nonchalant. "Something about visiting Diamond Tiara and Silver Spoon. Maybe Button Mash is over there."

"Oh no..." He gulped and took a deep breath, the sound of his wet and sticky dick plopping against the fashionista's boobs was obvious.

"What's wrong dear sister?" Rarity smirked, her tits working faster. "It's not like your coltfriend is being held against his will. You can go check on him." She bit her lip at the irony of her words, feeling his cock throbbing against her chest.

Sweetie Belle huff and groaned. "He's not my coldfriend?!"

"Then why are you calling me?" Rarity asked, her eyes glued to the young stallion, who was about to bust a nut in her cleavage. Button winced harder as merely hearing Sweetie Belle's voice was too much. "I'm sure Button will call you when he's done..." She shuttered at the building pressure hung up the phone, then pushed her breasts even tighter, causing him to squeal.

"Please... Rarity, stop teasing me!" Sweetie Belle huffed and hung up, giving her final word. "I'm heading home."

"Oh Button..." She licked her lips, her hands grasping the sides of her boobs and squeezed them around his length. "You truly are a heartless stallion--" She was cut off as white sticky fluid shot from his tip, and coated her face. The young stallion gasped, his body twitching, his mind blanking. Rarity closed her eyes and mouth, but she couldn't help herself and moaned as his seed splashed her lips. "Sweetie Belle has quite the spell over you. But, we're not done yet."

Button's legs shook as his orgasm ended, his body slumped forward, his chest heaving. He was a sweaty mess, and his dick was still rock-hard. Especially as Rarity swung her body around and puffed up her ass, giving him a perfect view of her dripping pussy and perky anus.

"We better move faster." Rarity growled, rubbing her ass against his crotch, her eyes glowing with lust. "Don't want Sweetie Belle walking in on all of this." She giggled as her mother began rubbing herself out to the scene. "Since we don't have all night..." She smirked and pushed his dick against her anus, the heat making him groan.

Button moaned, his hips bucking as her ass pushed him into the wall. He felt the softness of her skin and the wetness of her flesh. The fashionista's ass was soft and plump, and her tight hole gripped his shaft like a vice. He couldn't believe this was happening twice in one night. Inside another mare so quickly.

"Fuck, your dick is amazing." Rarity groaned, her hands against the floor, gyrating her hips as the young stallion began to slowly push back. Her tits slowly swung left and right out of her pirate jacket, her hair flowing freely. "Yes, right there... That's the spot."

Button placed his hands on her ass and squeezed her cheeks. He pushed his cock back and forth, having little effort in making her scream with joy. She was so tight, and the friction of her anal walls was incredible compared to her mother's overused pussy. He gritted his teeth and leaned in, taking a hand full of her hair.

"Harder, young punk!" She screamed out, her hips bucking back into him. Her body just kept shattering any sense of composure.

His balls were aching with more lust then he had in a long time. The young stallion growled, hips moving on their own, hands slowly riging up to spank her asscheeks. He could feel her anus gripping his shaft, the heat of her body and the pressure of his cock made his heart race and body tingle. The young stallion couldn't help but yank her hair back harder and get lost in the moment. The phone rang one final agonizing time and this time, he flat out ignored it, knowing it was his phone but too much in lust to care.

Rarity let out a loud squeal, her body convulsing, her juices coating his dick and thighs. Her ass cheeks rippling with each hit and her face flushing red. "Yes, yes, yes!" She moaned, her hips jerking as the young stallion began plowing her harder, his balls churning and cock throbbing.

Button gritted his teeth as the visages of Sweetie Belle returned. Somehow, after plowing both her mother and older sister, the annoying young mare's image just keeps reappearing in his head. However, where inside her mother all he could think about was how cruel Sweetie Belle was treating him, all he could see now was all the softer and kind moments they shared.

From their many night marathon video games and binging anime. Her many trips to his house to try out some new cosplays with him and go to cons. On the rare chances that he didn't even need to ask her to wear sexiest pieces, the mare would just show up in them and tease him. And the nights he spent holding her and stroking her mane after they got drunk with friends. All the times she cuddled him for warmth on those cold nights outside. The memories flashed before his eyes as his body gave in.

"Ahh!" Button cried out, his body tensing up. "Sweetie Belle..." His breathing got worse the moment he spoke her name out loud.

"That's it, baby... Cum out at her name." Rarity whimpered, pushing him out of her anus and slapping the cock right between her asscheeks. She grinned at the sounds of the door unlocking, making sure he was in full view of anypony that dare come through the entrance. "Shower me in the white seed Sweetie Belle kept refusing!!"

"Sweetie Belle!" Button gasped, his balls tensed and his cock flexed, his body shivering. Just as the door flew open and Sweetie Belle's real voice hit his ears, all the semen rained over Rarity. A huge amount splashed her ass and back, the rest covered her costume and hair, and a little dripped onto the floor.

"What the fuck is going on here?!" Sweetie Belle stood in the doorway, her jaw hanging open. Button Mash flipped around in a mess of confusion, lust still steering within him. Especailly upon seeing Sweetie Belle's costume. He was in such boredom before hearing her choose trick or treating that he totally ignored her costume originally. However, after fucking her mother and older sister, his senses were in overdrive upon seeing her full cleavage and thighs on display in a princess peach costume, his favorite video game girl now less, all he could do was bust another rope.

The sight of her mother and sister covered in Button's cum was crazy enough for Sweetie Belle, but upon seeing Button blast off another right in front of her, all over her sister's ass, just kick things even higher. She dropped her candy, slammed the door, and charged right at him. "You bastard!"

Button's heart sank into total terror and he held his hands up, trying his best to mend anything out of all these mistakes. However, it just kept jumping from 10 to 0 then to a full 20. As with no regard that her mother and sister had just ridden him like a wild horse, Sweetie Belle braced Button against the wall and locked lips with him.

******

Author's Note

Well, Sweetie Belle seemed pretty mad... And Button was a total asshole... I guess things were bound to go this route

Sweetie

There Button Mash was, after creaming her mother and sister, he expected her to punch his lights out. However, this house continued its lustful journey regardless. Button's heart raced as Sweetie Belle leaned in, her eyes sparkling like the stars above. In a shocking heartbeat, she pressed her soft lips against his face. With her arms wrapped around his shoulders, she pulled him closer, the gentle pressure of her body against his igniting a whirlwind of emotions within him. He could scarcely believe what was happening; it was a moment he had only dreamed of.

Her lips tasted sweet, infused with chocolate, a delightful reminder of her youthful exuberance and holiday experience. This intoxicating flavor enveloped him, swirling around like the memories of all their shared laughs and secret whispers. Button's mind raced, trying desperately to process the cascade of sensations washing over him while her hands cupped his face, holding him steady.

The moment expanded as Sweetie Belle's playful demeanor transformed into something far more lustful. As she gently parted her lips, Button felt a spark of courage ignite within him. He responded instinctively, his tongue meeting hers. A tender exploration of uncharted territory turned into a battle for dominance over the mouths. It was thrilling and terrifying all at once, a dance of curiosity that neither had anticipated to be so intense. Sweetie Belle in turn could smell her mother and sister's scent all over him, driving her up the wall with a mix of jealous and lust.

Time seemed to stand still; the world around them faded into a blur, leaving only the warmth of their connection. Button's hands found their way around her back, pulling her in closer, losing himself in the sensation of their embrace. Each soft caress of her cleavage against his bare chest sent shivers up his spine, driving him deeper into this unexpected moment of intimacy.

As the kiss deepened, challenges and uncertainties melted away, replaced by an overwhelming wave of desire within both of them. His eyes rolled back and his fingers dug into the bra strap on her back, She didn't stop him upon hearing her zipper drop and feeling his touch travel over her in ways she wanted so badly for so long. And this was enough to finally break the kiss.

It took a solid three minutes before Sweetie Belle pulled away, both young lovers gasping for air. They stared into each other's eyes, pupils dilated, a faint flush spreading across their cheeks. Button's chest heaved, his heart pounding like a jackhammer, adrenaline coursing through his veins. He tried to say something, anything. Only for the slap to the face to finally happen.

"How dare you cheat on me!?" Sweetie Belle snapped, her hand striking him across the cheek, a stinging pain erupting along his face. "I was going to give you fucking virginity tonight and you pull this shit."

Button flinched, his ears ringing. His mind raced at the utter horror of his actions only to crash face-first into her second line. "What were you offering?"

The young mare rolled her eyes over the scene of her mother and sister's wasted forms and slowly turned back to him with a loud huff. Yanking his ear over, she screamed at the total of her lungs. "You asshole! I've wanted you to take my virginity all fucking night!!" She flipped him around and threw him on the floor. "And if you want to take it so badly, I'll make you have it." She grabbed him by the scruff of the neck and pushed him onto his back, mounting herself above his crotch and dropping her top.

"S-sweetie, w-wait a second." Button pleaded, his voice shaky, and his eyes widened as her breasts popped out and her lips returned to his mouth. He moaned against her, feeling her hips slowly gyrating atop his exposed crotch. "I-I don't know if I can handle another orgasm."

"Shut the fuck up and take it, you Jackass!!" She reached down and squeezed his cock so hard against the entrance to her tight and virgin pussy. Button's eyes rolled back and he grunted against her.

"Sweetie Belle." Rarity moaned, watching her sister riding her young stallion with a smile on her face. "Oh my... Did you really spend all night walking around without panties... Hoping he would take you in costume." SHe shivered and squirmed, dropping her hand between her legs. "Just like I did during Spike's last ever Nightmare Night... So romantic!!

"Shut up, sis!" Sweetie Belle huffed, her eyes fluttering to her mother. "Mom, don't look at me like that either... I've been wanting this dense freak for years!" Her hips rocked and shook against his crotch. "And now I'm taking--" She shuttered the tip came to firm attention against her pussy. The young stallion couldn't hold back, pressing himself through the barriers and leaving the young mare with wide eyes. Her mouth echoed out with hard grunts and deep moans at the back of her throat. She could feel him grow slowly erect inside her pussy into a hard and sharp pipe barreling into her.

Button gasped, his body quivering under her form. He couldn't believe how tight her virgin pussy was. Her walls hugged his cock, gripping him in the strongest vice yet compared to the previous mares. It was a whole new world of sensation, unlike anything he had ever felt. Rarity was a well-used whore by a dragon who had firmly curved those insides to his shape. Cookie Crumble was a canyon of emptiness from age and multiple childbirths. But Sweetie Belle, was so piety and crackling, each press leaving them both gasping for so much air.

"S-so big..." Sweetie Belle whimpered, her hands resting on his chest, her body shaking. "Bigger then... I ever expected." Her voice was trembling, her hips could barely keep a straight pace. Yet, as the lust of her inner desires took control, and over time a good progression began to rise. Flipping back and forth between the sensory of being stabbed and utter ecstasy.

The young stallion winced, her body so warm and tight, his cock twitching as her folds just kept consuming his length so slowly. Barely three inches in he gritted his teeth at a hard wall. The friction of her pussy made his mind melt, yet the obstruction intensified the pleasure. His hands wrapped around her hips, and stopped her firmly in place.

"Sweetie." He winced, his chest rising and falling. "Sweetie..." He repeated her name with greater desperation. The young mare's eyes flickered and her body began to slow down, his words finally catching her attention.

"Yes, Button." Sweetie Belle breathed heavily.

"Sweetie Belle." Button swallowed hard, his cheeks flushing bright red. His body sitting up, and his face leaning into her mouth. Stopping mere centimeters from the prize, he wrapped one arm around her shoulder. "I love you." He pressed his lips against her, flipped her whole body under him, and backed his cock out of her.

Sweetie Belle felt a mix of confusion from the lovely words to his sudden retreat. However, it all became clear as he crashed back into her pussy at full force. Sharp pain twisted, her teeth gritted and her eyes went the widest yet. Blood splattered over the floor as Button fucked hard through the final barrier... and then just kept fucking.

"Sweetie Belle..." Button groaned, his arms around her neck and back. "I've loved you for so long, I couldn't imagine myself doing this with anypony else." He pulled her closer and buried his head against her neck, kissing and sucking her skin. Sweetie Belle moaned, her body quaking as the young stallion thrust forward with far more effort than he ever gave any previous mare. Her heart skipped a beat, tears swelled in her eyes. "You have no idea how many times I've jizzed about this moment!!"

"I've been waiting years for this too." Sweetie Belle whimpered, her hands gripping his back. "And now that I'm finally getting it..."

"Sweetie Belle, Sweetie Belle!" Button grunted, his cock slamming back and forth through her pussy like a jackhammer. Slowly, ever so much pushing away all the blood until her pussy was firmly accustomed to his shape alone. The friction of his dick was beyond her wildest dreams, every pump making her mind go back and forth between blank and red-hot lust. "I'm never going to stop, never."

"F-fuck, that's what I'm talking about." Sweetie Belle grinned, her legs wrapping around his waist, her body rocking and shaking under his. "Keep going, I need this." She gritted her teeth as each hard slap echoed throughout the room. Her sister and mother watched onward with a mix of joy and lustful anticipation to hear her very first climax.

Button growled and pounded her harder, the heat of her cunt burning him with every push. It was an addictive sensation, and he was powerless to resist, barrel so hard that his pullbacks would lift her clear off the floor. Sweat beaded on his forehead, his heart pounding faster, the rush of blood deafening. He could barely hear her screams or the sounds of her mother and sister moaning in their own rubbing sessions. The young stallion's hips moved faster, his cock twitching inside her tight cunt, his balls churning with his final hot seed for the night.

It was one he was going to waste, never fully retreating from this mare. The lovers always wanted more, endeavoring to give each other every ounce of their last strength and passion. The mare who would finally become his one and only. She and her alone could jack off him off every night, pump him inside her till he was just shooting blanks. Sweetie Belle's pussy was a heaven he would never leave, his hand gripped her asscheeks hard and his cock began to pulse.

Sweetie Belle somehow knew and chose not to fight this either, leaning up into a final kiss. Both their bodies become too erratic to control. Their tongues clashing, drool dripping down their cheeks and necks. The young stallion's thrusts grew faster and her hips moved in a crazed pace. All they could think about was the next few moments and the greatest end to this incredibly quick but perfect night.

"Sweetie Belle!"

"Button!"

Their cries echoed in a symphony as they hit the crescendo. A rush of white heat filled the mare's womb and her juices soaked his crotch. Both young lovers froze in place, their eyes rolling back but their lips never breaking for air. Their orgasms hit harder than anything they had experienced that night. Sweetie Belle's toes curled, her fingers digging into his back, her whole body shivering uncontrollably. Button grunted and groaned so hard into her mouth. Shot after shot barreled into her virgin womb, blasting her with more heat than she ever felt in her life. Their visions blurred and both fell overtop each other and unconscious on the floor.

A few seconds later, the door opened again, revealing Cookie's husband to the whole scene. "I'm here. Did I miss anything?" He stopped upon the visage, slowly walking around it and to his wife on the couch. Dipping down and gave his masturbating wife a kiss on the lips and then a second right on her pussy, while both daughters were in the room. Lifting his head up, he finally gave a response to the scene of his youngest daughter and the other stallion. "Sweetie Belle finally got her prize."

He picked Cookie Crumble up and carried her to the stairway. Stepping over his oldest daughter rubbing herself out, he kicked her phone to her and asked. "Can you have Spike clean up this mess, dear?"

"Of course, father... As soon as he comes back from plowing Diamond Tiara and Silver Spoon..." She held up the phone, showing pictures of the two naked young mares crawling over the dragon.

"Okay... Text him to not hurt himself before returning to your side."

"Already done." She smiled and went back to masturbating, leaving her father and mother to go upstairs for more rounds of pounding in the privacy of their room.

******

Author's Note

I know the ending seemed a bit short, but I was running on smoke with that. Yes, I wrote this whole thing in a single sitting and then came back to write the bonus chapter. However, no, the bonus chapter is not some clean marriage sex.

When will the bonus chapter drop, Sunday? Nah, it needs more time to marinate. I'm thinking about dropping Monday, the same day I'll be returning to SILC.

Bonus: Cockholding

Author's Note

Sorry this came out so late, been sick all week from enjoying Halloween too much. Either way, not as big as I wanted this bonus chapter to be, but I made you all wait long enough. Here is the final chapter.

And yes, I'll be posting the next episode of SILC in a few hours.

Bonus: Cockholding

As the autumn leaves danced through the crisp end of October, Sugarcube Corner was transformed into a horror of color and sound. The familiar bakery, known for its delightful pastries and cheerful atmosphere, had taken on a new life, resonating with loud music and the laughter of dozens of young trick-or-treaters. Pumpkins carved with grinning faces adorned every corner, while cobweb decorations hung from the ceiling, creating an enchanting atmosphere for the Halloween celebration.

Mr. and Mrs. Cake found themselves at the heart of the whirlwind of hard work. The couple worked tirelessly, balancing trays of freshly baked treats and scooping swirls of frosting onto cupcakes decorated to resemble ghosts and goblins. The sweet aroma of sugar wafted through the air, mingling with the crisp scent of fall, drawing in parents and children alike, their costumes brightening the room with vivid hues.

“Honey, we’ve run out of caramel apples!” Mr. Cake called out, his voice rising above the music.

“I’ll whip up another batch! Just keep an eye on those cupcakes!” Mrs. Cake replied, her hands working to prepare more treats. She darted towards the kitchen, where the faint sound of bubbling cauldrons and the warm glow of the oven invited her in. Her heart ached and back twisted upon noticing it again... Pinkie Pie was nowhere to be found.

Just moments before her disappearance, Pinkie was in her element, leading a spirited conga line that wound through a tunnel of whimsical balloon animals fashioned to resemble spooky creatures. Laughter echoed off the walls as ponies of all ages got swept up in the delight of the moment. Each balloon animal seemed more awe-inspiring than the last, with glowing faces and exaggerated features that added a touch of whimsy to the vibrant atmosphere. With her signature poofy mane bouncing energetically in rhythm, Pinkie commanded the whole party.

As the festivities progressed, her organizational skills were on full display. Every corner of Sugarcube Corner was dotted with games ranging from bobbing for apples to the ever-popular musical chairs, while another showcased an elaborate punch bowl bursting with fizzy, vibrant colors. Every sip promised a new flavor, tantalizing the taste buds and fueling further excitement. The air buzzed with laughter, cheers, and the sound of music, all perfectly curated by Pinkie herself.

But just as quickly as she had ignited the party spirit, she faded from it. Where had Pinkie Pie gone? What could possibly pull her away from the revelry she had orchestrated with such vibrancy and joy?

“Have you seen Pinkie?” Mr. Cake asked a group of young fillies dressed as broomstick-wielding witches.

They giggled and shook their heads, their candy bags bulging. “Maybe she’s in the back, frosting cupcakes like a ghost!” one of them suggested, and they burst into laughter before racing towards the pin-the-tail-on-the-pony game.

The buzz of activity, the shrieks of delight over a successful candy grab, the sounds of impromptu dancing, grew more pronounced with every moment. Still, the Cake Parents couldn’t help but glance around, searching for the party planner who usually ensured that every detail was perfect.

Meanwhile, in the depths of the bakery, unbeknownst to Mr. and Mrs. Cake, Pinkie Pie was hard at work... getting her pussy pounded by the young stallion, Rumble.

Pinkie's legs were spread wide open, her feet flung back and forth on the counter as Rumble thrust into her again and again. He had a firm grip on her hips, holding them tight as he bucked wildly, his eyes shut and his teeth gritted in pleasure.

"Damn... the rumors are right, anything for some hot white frosting!" he grunted as his cock slid deeper and deeper into her wet folds. Rumble had his wings extended out, and he was trying to balance on the countertop. The stallion was wearing a black hoodie with a red devil design, his pants dankly on his ankles, while his cock being shoved in and out of the pretty, busty and pink angel pony.

"Just don't waste a single drop!!" Pinkie Pie laughed between breaths. Her eyes were closed as she bit her lower lip and whimpered. Her hair was flowing and bouncing as her tits flopped up and down. Her fake wings were spread in and out like real ones. Her body fluttered with a mixture of arousal and thrill. The young stallion's hips were relentless, his hands resting on her bare thighs, barely able to keep any sense of control.

On the otherside of the room, Cheese Sandwinch was tied to a chair, his cock firm in his hand in front on Pinkie Pie's waiting face. The older stallion was blatantly smiling, even with his eyes locked on the scene and his mouth gagged with a cupcake, his tail swaying around as his cock was thrusting and rubbing at the sounds of his wife's wet pussy getting pounded by another.

Rumble couldn't believe she accepted his frosting-covered offer so easily. Coming here as a last resort as he couldn't wrench Twilight away from those books. Not helping was her guards pounding into her the whole time he was talking to her early. Damn, nerd barely batted an eye at either of them, forcing him to head over here for his action.

However, he never expected to be involved in a cockholding event. Seeing Pinkie Pie's husband twist and shutter in his chair as he beat into the mare. His cock throbbing and pulsating with each shove forward. The walls of her tight, warm, and wet pussy clenching and gripping him. There was no sense of foreplay or extra movements, the young stallion couldn't think of anything else, his body just moving on instinct.

Pinkie was having a blast. She turned awau and watched Cheese's reactions. She could tell his body was eager and desperate, his balls begging for a release. His cock was already throbbing and twitching, the veins showing how tense and firm it was. She giggled and winked, knowing the poor stud was suffering for her love.

"Come on, Cheesy! You can't cum until I say so!" She teased, turning her attention back to Rumble. The young stallion's hips continued to rock, his dick thrusting in and out with great speed and passion. He grunted and groaned, the pressure building and his muscles tensing. Pinkie's body was so warm and welcoming.

Seeing that both stallions were about to cum, she turned toward the audience reading through their laptops, possibly jacking off to all this disgusting diabetic filth. "Did you really think Lighttone Gryphonstar would be cruel enough to torture the little brother too..." She shivered and shuttered, feeling the young stallion's seed rise. "Not a chance, Thunderlane is his one and only Kenny!!"

With that final word given, Rumble pulled out and showered semen all over the pink mare's angel costume. In the same moment, watching his wife get covered was enough to break the tides for him too. Cheese Sandwich smashed the cupcake down and blasted his own load of semen all over her face. She opened at her mouth and licked up every drop that reached her face of both loads of frost pipping over her.

The stallions panted, their cocks still firm and twitching as he looked down at the mare. Her wings and dress were completely ruined. Pinkie stood up, dropping her whole costume and gestured him over. She giggled and wrapped her naked breast around both cocks at once. "Oh, no! We are far from done tonight!" She cooed, pumping her tit's against the throbbing members. "I am so hungry

******