Thirty One Nights Of Nightmare Night!

“Welcome everypony, once again to the annual ‘Running of the Leaves’ festival!” Pinkie Pie’s voice boomed out over the speaker from up high in her hot air balloon. “We’ve got an amazing lineup of ponies from all over Equestria here to participate in the race today, which’ll surely make this a race to remember!”

Applebloom was sweating, and the race hadn’t even started yet. She couldn’t believe she was about to go through with this. Spur stood right beside her but was looking towards another pony. Big Macintosh was talking to his wife, Sugar Bell, who was several months pregnant and she looked like the baby could be due any time. He gave her a kiss and then approached the starting line.

“I must be crazy.” Applebloom said under her breath.

“Yeah, this is a little crazy.” Spur admitted before turning to face Applebloom. “I really hope this’ll work though. Are you sure he’d actually want to? I mean, I am all excited after last night’s errr…”

Spur didn’t finish her sentence. Too many ponies were crowded around them but Applebloom knew what she was talking about. Just remembering what happened last night made the filly blush, in fact she had been thinking about it all night. She wanted this to happen just as much as Spur did.

“Ponies, to your marks!” Pinkie called out from above. All the ponies formed a line as Applebloom made a beeline to stand next to her brother, with Spur following in toe.

“Hey Big Mac!” Applebloom called out to him. “Umm, d-do you mind if we run with you? I mean, Applejack is running to win, but… it’d much rather race alongside you.”

The red stallion looked down at his sister. His orange mane was now trimmed neatly and his Yolk was left at home. He was now wearing a blue plaid shirt.

“Eeeyup!” He said with a smile.

“Okay, Ponies! On your marks!” Pinkie’s voice boomed. “Get-set-GO!”

She yelled fast and everypony took off unsteadily, not prepared for such a rushed countdown. But with it being Pinkie Pie, they shouldn’t have expected anything less. Applejack expected it though and was ahead of the pack, with a whole crowd of ponies just behind her as Pinkie called out the play-by-play. Ponies started to thin out after a few minutes of running. Some slowing down to pace themselves, others going at a full sprint, not realising how long this was going to take. Once Applebloom, Spur and Big Mac were deep into the forest, the yellow earth pony looked around her. Only a few ponies were behind them. She knew they were at the latter quarter of the racers, but she needed to be at the back, alone with Spur and her brother. The yellow filly then enacted her plan.

“Whoa!” she yelled as she fell over and landed hard on the dirt floor.

“Applebloom!” Big Mac yelled out, stopping to check on his sister. Spur also turned back. “Are you hurt?”

She sat up, holding her foreleg.

“Ow, I’m fine. It’s just a-” She stumbled a little, unable to stand on her leg.

“Nope!” Big Mac turned to call for aid, but Applebloom stopped him.

“No! Don’t. Just… just let me rest a moment on the sides?” She nodded her head towards where all the leaves had fallen. A few runners had stopped to check everything was alright, but Spur was keeping crowd control, letting them all know everything was fine, she just scraped her knee.

As soon as they were finally alone, Applebloom slowly stood up with her brother supporting her. But really, she needed no help.

“Thanks Big Brother, but… I’m alright. I’m not actually hurt.”

“What do you mean, you’re not hurt?” Big Mac asked, confused.

“I tripped on purpose because... we wanted to talk to you... in private!”

Big Macintosh looked between the two ponies, each half his size.

“Couldn’t this wait?” He asked.

“Well, there wouldn’t be time. Spur is leaving in the morning and has to pack tonight. This was her only chance. Our only chance.”

Big Mac looked towards the brown pegasus who was trying to avoid eye contact, but yet she couldn’t take her eyes off him.

“See, she’s going to be moving so far away and we might never see her again, and… she wanted to ask... we wanted… umm... “ Applebloom wasn’t sure how to continue. She rehearsed this in her head a million times, but now the moment was here, her mind was blank. ”Umm, you see. She wants… I mean, she was hoping to…”

“Applebloom, What is this about?”

Big Mac was getting confused. Why was his youngest sister turning red? Why were they both going red? He couldn’t understand what was going on. What could Spur want from him that required them to be completely alo-

Then it hit him like a ton of bricks. He looked to Spur again, his eyes wide. She was blushing more now, smiling with her eyes locked with his. Applebloom was blushing and looking away embarrassed.

“NOPE! Nope nope nope nope nope!” He said, taking a step back. “Applebloom, how could you even think I would agree to this? I’m married! My wife is back there pregnant with my foal.”

“But...“

“No, young filly. Spur, how could you even put her up to this?” He sounded so disappointed in her. He used to think she was a good influence on her.

“I’m sorry, sir. It’s just… I-I’m in heat and I-”

“You’re not in heat. Stallions know the difference. This is… you’re just…”

He didn’t want to finish.

“But… didn’t you say you wanted to?” Applebloom said, looking to her brother.

Big Mac froze as he turned to Applebloom.

“I heard you before. In the bathroom a few nights ago. You said that you were getting more frustrated because Sugar Bell hasn’t had sex with you since she learned she was pregnant. Y- you said you wished that some mare would just let you rut her, just for some relief!”

“Y-y-you heard all that?!” He said, shocked. His own little sister had heard his whispered conversation while talking to himself in the mirror. “Applebloom. That was… It’s…”

“Please, Big Mac.” Spur said, speaking up. “I know I’m not much, but if what Applebloom is saying is true, you could… you know… with me. I promise I’ll tell no pony, not even after I move away! I just… When I see you working on the farm, I feel-”

“I don’t think you realise what you’re asking.”

“But I do! Please, Big Mac.” Spur pleaded. “You’re right. I am horny. I’ll admit it and I promise, it’ll be a one time thing. We’ll never have to speak of it again.”

“Please, Big Brother. This’ll be our secret. And... you still owe me a favour since I helped you clean up the kitchen.”

“Applebloom, I don’t think that favour can be used for something like this!”

The red stallion looked around. They were all still alone but he couldn’t do this, could he? She was so much younger than him, not even of legal age in Equestria.

“Spur, I…”

“Please, my first time was such a disappointment, that… I’m not even sure I’d want to be with another stallion. I was hoping an older stallion might, you know, do it right? And I know I’m not a very attractive young mare compared to most, but-”

“Now wait a moment.” He interrupted. “You are plenty beautiful. Don’t ever doubt yourself like that again. You’re gorgeous and any stallion would be lucky to be with you!”

“So you’ll do it?!” Spur said excitedly.

Big Mac had put his hoof in his mouth now.

“Please, Big Mac! We’ll tell no pony, we swear.” Applebloom added on top of it.

The filly had been fantasising about this all since last night. Even in her sleeping bag during the clubhouse sleepover she’d touched herself at the thought, but she’d dare not finish with her friends right beside her. The stallion sighed and then looked behind him. He nodded his head towards deeper into the words. The two fillies giggled with excitement and followed him.

After a few minutes of walking, Big Mac decided that they were far enough into the woods that there was no chance anypony would find or hear them out here.

“Alright, this’ll be far enough. Applebloom, you go back to the race and tell-”

“What?! No, I wanna stay!”

“B-but you’re my sister.”

“I… I promise, I’ll not say anything! You won’t even know I’m here.”

Big Mac sighed. He was not going to get his own way with anything it seemed. Spur stood in front of Big Mac and then turned around, flagging her tail.

“Is… this good?” Spur asked, a little nervous but definitely wanting this to happen.

He looked at her most private area which seemed to be a little bit wet already. She was definitely excited. He couldn’t believe he was really going through with this.

“Wait.” He said. “I’m not ready yet. If we’re really doing this, then… You’ll have to get me ready first.”

She turned around and faced him again.

“Okay, just tell me what to do!” She said, clearly excited about this.

Big Mac looked about and then found a large rock. He brushed a few leaves off of it and then sat down. The entire area was covered in fallen golden and orange leaves, but many remained on the trees giving them aerial cover for passing pegasi, not that there would be any. The majority of ponies here were racing and the three of them were so far off the track now, they’d never be found.

“Alright.” Big Mac said spreading his legs, there was a blush on his face as he realised his little sister was looking directly at his balls “Y-you’re going to have to get me hard.”

Spur didn’t hesitate, she immediately stepped forward and sat between his legs. The pegasus leaned in slow and then started by using her tongue on his sheath. Big Mac wasn’t expecting her to be so bold about it. She went down to his balls next. The young mare went down to his balls next. Heck, he’d even dare call her a filly still due to being underage and her only being slightly taller than his sister. She started sucking one of his balls into her mouth and then went to the other one, licking them both and holding his scrotum up with her hoof. It was so erotic, and he’d been so pent up for months. His cock finally started to emerge and Spur moved up and ran her nose along it very very slowly as it came out. Her mouth was open too, her hot breath on his cock made it twitch, especially when her tongue began to follow after her nose.

“Oooh… I-” Big mac took in a steady breath then exhaled. “I thought you said your first time was a... disappointment?”

“Mine was. But theirs was incredible. And we’ve had practise, but he never satisfied me. But this...” Spur kissed the tip of his now fully exposed, almost rock hard shaft. “This looks like it’ll do the job.” And then she took the entire head of his cock into her mouth.

He was certainly as big as Applebloom had said, but seeing it in person like this gave Spur chills. When the yellow filly said that Big Mac was too big to fit in Scootaloo’s mouth, she may have been right. He was huge, but she wasn’t going to hold back. Holding the head in her mouth, she began to lick in circles around it taking occasional sucks, as if wanting to take him in deeper, but this might have been beyond her limits, He was rock solid now anyway. She then pulled his cock out her mouth with a pop, and then stroked it up and down. Big Mac moaned as his cock twitched in her hoof.

“Are you ready?” Spur asked with as must lust in her voice as she could manage beyond the giddy excitement.

Big Mac climbed down from the rock and grabbed Spur to lie her down, face first, on top of it.. He then gave her pussy a quick lick to test her. She was already soaked and she also tasted divine. Her squeal was muffled only by her hoof as she buried her face. Her grin was huge though, she was finally going to live out a fantasy she’d had ever since she met the stallion. She felt his massive cockhead pressing against her pussy. She was ready, he was ready. However, Applebloom wasn’t sure if she was.

Watching from the side had gotten Applebloom very hot and seeing her friend suck him off was incredible, but looking at him bend her over, she could see that there was no way he was going to fit. He was too big. Her brother pushed hard against her friend's entrance and Applebloom saw her friend’s face scrunch up in pain. Big mac pulled Spur’s legs further apart.

“Mmm, come on you sexy filly! You wanted a real stallion's cock didn’t you? Loosen up then, relax and just… let… me… IN!”

He thrust hard and Spur’s pussy gave way to the Mac’s huge penis, making her arch her back in a silent scream of pleasure. He was inside her moist tunnel, barely a quarter of him was, but he was in, and she felt so full.

“Spur?!” Applebloom ran up to her friend. “Are you okay?”

Spur just looked back at Applebloom with a doopy expression on her face.

“So full. So good!” Was all she said. Big Mac smiled proudly and then began thrusting. Spur was moaning, gasping, her insides were alright like she was on fire. This was what she was missing, this was what true sex was meant to feel like, the feeling of being complete, like this dick was always meant to be inside her, but she was far from being completely filled. Each thrust was getting her more stretched out, and the longer this went on the closer her first orgasm was approaching. Spur was banging her hoof on the rock, scraping against it, wanting to hold onto something as the older stallion pounded into her all the way to his medial ring, halfway down his cock. As she was about to cum though, Big mac pulled out. She was about to protest before she was flipped over and then before he plunged back in, he leaned close to her.

“I want you to look at me while you cum! I wanna see the look of a satisfied mare!”

And she did! The moment his cock reentered her warm folds electricity charged through her body and she was instantly gushing along his cock, soaking him and the rock beneath them. Her face was exactly what Big Mac had hoped for. Eyes wide open, head tilted back and mouth wide open, gasping and moaning in absolute pleasure.

Applebloom watched her friend clench, buck and twitch as her brother cock impaled her. How was she able to take so much? How big was her own pussy? Could it fit something in like that?

Big mac then picked Spur up while she was still riding her orgasm high and then leaned her against a tree, he was now standing and thrusting upwards into her, letting her fall down as gravity helped impale her as deep as he could go into her.

She was moaning loudly now, almost screaming and he bucked her harder, hitting the tree with force. It was hurting Spur a little, but she was riding such a high from being so totally stuffed that she didn’t care. The leaves were being shaken loose as he plowed into her, each falling slowly but making a large pile beneath them.

Applebloom was sitting on the floor now, touching herself. She couldn’t help it. Watching this happen right before her was an incredible sight and so erotic. Spur was grabbing a hold around Big Mac’s neck just holding on for all she was worth as he plunged up again and again, stretching her around his ring, but no further, she was at her limit. Each time the medial ring slipped inside her, she screamed loud, the pleasure was so intense that she couldn’t do much else. Opening her eyes, she saw Applebloom sitting with her legs spread, masturbating. Seeing her getting fucked hard made her friend this horny? Spur smiled with a wicked idea and then whispered to Big Mac. He looked back, saw what his little sister was doing and then grinned.

“Want a better view, sis?”

Applebloom squealed and covered herself up, ashamed. Mac then carried Spur, still all the way on his cock, and placed her between Applebloom’s legs and then continued to plow into her pussy while looking at his sister. Her face was so red from being seen, but now her friend was right between her legs, head tilted back to look her in the eyes.

“A-A-Applebloom! D-Don’t stop!” Spur said between thrusts as Big Mac continued to plow into her.

“Go on sis, you wanted to watch, right? Or, really, did you want more than that?”

Applebloom had never seen her brother like this. Normally he was so silent, but here in this situation, he was a different stallion. She then felt a hoof on her’s. Spur was taking the hoof that had been touching herself and was pulling her closer. The brown pegasus pulled until the yellow filly stood up and then was over her face. Spur pulled her down and then started licking her cunny! Applebloom’s jaw dropped and her whole body went rigid. She was shaking and her brother was getting so close to his climax, especially seeing his sister getting eaten out by the young mare he was fucking. It was one of the hottest things he’d ever seen.

“S-S-Spur!” Applebloom called out. “Y-you’re... OH!! SPUR, PLEASE!!” Spur herself was in heaven, she was getting to taste her closest friend’s cunt and it was so sweet, while meanwhile the lower half of her was going numb from the intensity of Big Mac’s thrusts. She didn’t know how long she’d last before cumming again. Big Mac himself had been so pent up that he was on the verge of cumming, as was his sister.

“OH GOSH! I Can’t- I’m gonna!” Applebloom squealed as Spur's tongue masterfully went to work on her young folds.

“L-let it all out Applebloom.” Big Mac said, exhausted. “Cum in your friend’s mouth and say it! Scream it! Tell her what you’re doing!”

“Sp-S-Spur… I-I’m..c-c... I’M CUMMING, SPUR! AHHH!!”

Spur sucked hard on her friend’s yellow cunny lips, knowing she had to be the first to do this to her and taste her cum. It was enough to drive Spur again over the edge and buck harder against the red stallion as she felt him cream pie’d her! Shooting all the way deep into her cunt and filling her womb with his hot sperm. All three ponies were moaning and crying out, Big mac grunting especially hard as he tried to push the rest of himself inside the young mare, but he couldn’t. Instead he pulled out of her and jerked himself off, shooting the last spurts of cum over Spur’s belly and one particularly strong spurt splating against Applebloom’s face, making her cry out.

Exhausted, spent, and oh so satisfied, the three fell down onto the ground, leaves falling around them all as they tried to catch their breaths.

“W-wow!” Applebloom said, barely able to move.

Spur wiggled over to atop of Applebloom and then licked the line of cum from her face, and then she kidded her on the mouth, making the farm filly’s heart skip a beat.

“Thank you.” Spur whispered, and then rolled to the side, onto her back.

Applebloom didn’t know what to think. That was her first kiss! Yes, they’d just done something much more intimate, but… in her head, that meant so much more.

“So... “ Big Mac said between breaths. “Was that satisfying enough for you?” He chuckled as he sat up. Spur wasn’t moving a muscle, apart from her chest rising up and down, as she was catching her breath.

“That… was… the best… sex... I’ve ever… had!”

Big Mac grinned and turned his attention to Applebloom who looked stunned. Just as he was about to ask if she was okay,they were interrupted by a voice from above them.

“You know, that’s a very effective way to shake leaves off of a tree, but not exactly efficient.”

All three ponies looked up to see Pinkie Pie in her balloon looking down at the three of them. The leaves from the tree they were under were gone! Big Mac had knocked all the leaves down while rutting Spur against it. None of them had even noticed that Pinkie had been floating there silently, watching them from above.