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.