Thirty One Nights Of Nightmare Night!

The late afternoon sun was shining brightly over Sweet Apple Acres. The trees were cleared of most of the apples for the day but work still continued for certain members of the family. Big Macintosh was busily rebuilding the last piece to the former Cutiemark Crusader clubhouse, hammering in the new wall that he and Applebloom had put together. Though, mostly it was just him. Applebloom had been in a haze the last few days, ever since Spur left Ponyville without a trace.

She wouldn’t just leave town without saying goodbye. She wouldn’t!

The same thought kept running though her head despite evidence to the contrary. Her hotel room was empty, no pony had seen her and she’d left her key at the hotel’s front desk. Big Mac hammered in the last nail and stood back, admiring his work, but his sister was still holding up the wall, not even noticing that she no longer needed to.

“Applebloom?” He said, but she didn’t seem to hear him. The stallion sighed and then walked over to her, placing a hoof on her shoulder, waking her from her thoughts. “Look, you’ve been like this for a few days. Maybe it really is just as I said. Maybe saying goodbye was too hard for her and she caught an earlier train? It wasn’t the first one of the morning, you know.”

Applebloom looked up at her brother, he was trying to be sympathetic, but he didn’t know her like she did.

“No, S-she would have. She always has!”

“Sis, this time was different. After… what we did, it’s umm... it becomes more complicated. Try to realise that as painful as this is for you, she’s probably hurting just as much. But you’ve got to try and move on. For both of your sakes. Okay?“

Big Mac gave his sister a reassuring smile. Applebloom still didn’t truly believe Spur would just leave like that, but maybe he was right. Things were different this time. But that’s why she was positive the pegasus wouldn’t have left without seeing her one last time.

Just then and sounds of ponies approaching caught their attention. Big Mac turned and saw Pinkie Pie and the Cake family in tow. The stallion gave his sister a reassuring pat on the shoulder and went down to greet them.

“Hey ya, Big Mac!” Pinkie said enthusiastically. “We were just coming to see if you needed any help, but it looks just about finished!”

“Eeeyup.” The stallion replied simply. The clubhouse looked brand new. The fresh wood, smooth rails, glass windows that shined, it looked nice enough that they could charge rent if they wanted to. Big Mac worked hard on it to make sure Pinkie would be happy with the deal to buy her silence.

“Yeah,” Applebloom said, standing beside her brother. “It’s just missing the interior, but the outside is solid.”

“This looks amazing,” Mr. Cake said, stunned by how good it looked. “But are you really okay with our foals playing here? I mean, you worked so hard on it.”

“Aww, it’s fine.” Pinkie said, putting a hoof around both Big Mac and Applebloom’s necks. “It was all their idea anyway, right?” Both of them agreed with varying levels of awkwardness. “And besides, by the time the twins outgrow it, Big Mac’s foal will be taking over, Riiiight?” Pinkie gave the stallion a nudge with a smile.

“Well it just looks incredible.” Mrs Cake said as she looked up at the tree house. “And… you’re sure it’s safe?”

“Are you kidding?” Pinkie said, speaking for both the Apples. “This thing’s made by some of the best barn builders this side of Equestria! Of course it’s safe! Come on up!” Pinkie said bouncing up the steps.

Mr and Mrs Cake looked to Big Mac who nodded, letting them know it was okay. The entire family went up the ramp which now had a safety rail going all the way up, and they all walked into the room. It looked so different. It was bare with nothing in it, but there looked like there was so much more room than ever before. The twins wow’d at it as they ran in, looking around and checking out the view from the window.

“This looks incredible.” Mr Cake said in wonder. “How in Equestria did you build this all so fast?”

“Practise.” Big mac said, thinking back to how many times he’s had to rebuild buildings on the farm.

“Yeah, this place is great. But it needs something...” Pinkie said, tapping her chin.

“Well, yeah, like-” Applebloom started but Pinkie spoke right over her.

“Like a sofa!” Pinkie then dashed out the door and as fast as she left, she returned with a sofa and slammed it down into place against the wall. “A Wardrobe!” The mare again dashed out and retrieved one from seemingly nowhere. “A rug, a lamp, pictures,” With each word, pinkie was running out the room and bringing in various items of furniture and filling the room with them. The twins watched in awe with smiles as their new clubhouse started to look like a home away from home. The mare wiped the sweat from her brow and then turned around with a smile.

“W-w-where did you…?” Big Mac stuttered.

“Oh, just some extra things I've had lying around. So, what do you think?!”

“We love it!!” The twins cried out in glee, hugging Pinkie.

“Aww, well don’t just thank me.” She said, indicating to the apple siblings.

Pound and Pumpkin both turned and thanked Big Mac and Applebloom which brought a smile to both of their faces. This was the first time Applebloom smiled in days, but the moment the foals turned around, that smile was gone again, and Big Mac was the only one who noticed.

By late evening, the Cakes and Pinkie were returning home and talking about how incredible the clubhouse now looked. The foals couldn’t wait to go back tomorrow. However, on their way back, Mrs. Cake startled them all with a shriek.

“My goodness, I forgot all about bridge night.” The family sighed in relief, thinking it was worse than that. “I’ll see you all at home, dearies. I’ll be at Lyra and Bon Bon's if you need me!”

And like that, she was off. Suddenly Pinkie was the next to speak up.

“Wait, if it’s time for her bridge night, that means…” The pink mare jumped into the air and gasped. “That means Pound is late for Rainbow’s night flight, flying lessons!”

“Oh no! I completely forgot!” Pound said jumping in the air, flapping his wings.

“Don’t worry, I’ll get you there!” Pinkie said, pulling the colt onto her back. “See you at home, you two!” Pinkie shouted before taking off at high speeds.

Mr. Cake was then left alone with his daughter, and they both let out a chuckle.

“Seems everypony’s in a rush tonight.” He said, looking down at his daughter. They then both locked eyes and realised that they were finally alone.

“Daddy? Can we rush home quickly too?” She asked, laying the hint on thick with what she had planned. The stallion looked around and thought for a moment. They were still in the orchard and the Apples had left the same time they did.

“Hey, how about we go back to the clubhouse instead? It’s closer.”

“Daddy!” Pumpkin said a little loudly with a squeak, but her smile was impossible to hide.

He then took her hoof and then together they rushed back to the clubhouse. It was getting darker but still no pony was around. The stallion double checked that before going up the ramp and inside. It all looked so wonderful. The interior, furniture. All clean and brand new. Yet here he was with his daughter, about to defile it. Pumpkin squeezed her daddy’s hoof excitedly.

“We’re finally alone.” She said, practically buzzing.

She’d always loved their games, but they almost always had to stop, or hold back, or stay quiet. Here, on a secluded part of a farm where no pony was ever going to come at night, they no longer had to do any of that. Mr Cake leaned down and kissed his daughter passionately on the lips. She kissed him back just as hard and opened her mouth for him, his much larger tongue darted inside her mouth and dominated the little filly’s, making her moan in excitement. He then scooped her up and pulled her to the sofa. They continued to kiss with him brushing her orange mane back, pulling away and then looking upon his daughter’s beautiful face which brightened up the entire dark room. He left the lights off in here so as to not draw any attention to the clubhouse, in the miniscule chance that somepony might see it from a distance. He kissed her again as he trailed a hoof down to her tight cunny, rubbing gently against her soft flower.

“Oh, D-daddy!” She moaned gently as he touched her folds in a way that was making her wet and him very hard.

He kept it going, making his little filly moan and wiggy in his embrace. She was being driven wild.

“Pumpkin… can I… could we try to...?” He asked in a whispered breath. She opened her eyes to look at him, wondering what he meant.

She saw his cock getting harder and remembered that he’d told her that ponies had sex properly when the stallion puts his penis in a mare’s vagina, but she was still so small, and while his cock was thinner than most, his length made up for it. Though for a filly as young as Pumpkin, his size was still frightening to her. She wasn’t sure.

“I promise not to hurt you, and if it’s too much, I’ll stop. Okay?” He said, trying to appease her.

He’d been thinking about this since their first night together, her mouth was so tight around his cock, he wondered if he could even fit in her pussy. But that was so long ago and she’d grown since then. She gave him a nod.

“Promise to go slow?”

“I promise.”

He then moved away from her as she laid on the sofa, legs spread for him. He still held one of her hooves as she looked up at him very nervously. Her pussy looked so wonderful as he slowly touched the head of his cock to her pussy, rubbing it around, using her wetness to make himself slicker, he rubbed his shaft all the way up and down her folds, making the filly moan and bite into her hoof.

“Sweetie Pumpkin, you don’t have to stay quiet anymore.” He reached forwards and pulled her hoof from her mouth. “Let Daddy hear your moans of delight.”

He felt so turned on by his own dirty talk, but even more so when Pumpkin let out a moan, louder than he’d ever heard her before. His cock twitched up and then slapped down on her cute belly. He took his member in hoof and rubbed her juices around the tip and then returned it to her virgin folds. This was it, not only was he about to finally have his release that had been building up for weeks, he was going to do it by taking his daughters virginity, that had him trusting his hips and clenching his asschecks in anticipation, struggling to not blow his load over her small body. He then started to push against her, but it wasn’t going in. His flat head was too big. He tried rubbing it around a bit more, trying different angles, but it just wasn’t going in.

“Pumpkin, I need you to relax a little more, okay?”

“O-okay.” She said nervously, but she looked and felt no different, she was still tense with worry.

He leaned down to her face and kissed her gently, stroking her mane. She kissed him back and melted into it, finally relaxing proper. He then angled his cock right, and then plunged the head into her at speed. She screamed, clenching up tight, turning her head away and squeezing his hoof incredibly tight.

“OW! Ow ow ow ow! Daddy! Stop! It hurts!” Pumpkin cried out, tears coming to her eyes.

“I’m sorry, honey!” He said, stopping his advances.

Only the head of his cock was inside her, and he wasn’t sure if he’d popped her cherry right there, but maybe he had with just this much inside. She was a small filly after all. Looking at his daughter crying like this he was instantly filled with regret.

“Please, Daddy! Take it out! It hurts too much!”

“It’s okay, just give it a minute. You’ll get-”

“No...“ She said with a sniff. “I don’t like it.”

He felt his heart cracking, he’d clearly taken it too far.

“Okay, I’ll take it out.” He started to pull out but Pumpkin’s moans of pain stopped him.

“Ow ow ow! That hurts!” The small unicorn started to bite her hoof again to siffle her crying.

“I’m so sorry. I can’t-”

He stopped mid sentence. He’d heard something that sounded like a giggle coming from outside. It was a very familiar one. He felt the colour fade from him.

“Pumpkin, somepony’s coming.” Her eyes looked towards the door in fear and he tried again to pull himself out, but the filly yelled in pain once again, stifled by her hoof.

He then panicked and picked her up, still on the end of his cock which caused her distress, but he couldn’t think of that right now. The sound of hoofbeats could be heard on the steps leading up to the clubhouse. Mr. Cake looked around for an exit, a back door. Nothing! He could try the window but they’d see him without a doubt. Pumpkin pointed a shaky hoof at the wardrobe. He had no better ideas so he jumped inside. Fortunately it was still empty, so there was space to stand, but he had to stand awkwardly with Pumpkin still extremely tight on the head of his cock and only on his hind hooves, using one hoof to hold his daughter steady and the other to close the door silently.

The clubhouse door then opened and Pinkie Pie walked inside, she stood aside and following her in was Pound Cake. Mr. Cake was surprised to see them both here.

What was going on, wasn’t she supposed to be taking him to those night flying lessons?

Pumpkin couldn’t see what was going on, her focus was on her father’s slowly shrinking cock, giving her some relief. She still felt sore, but it was easing now. He continued to watch as Pinkie closed the door and then grabbed Pound Cake’s hoof.

“Told you we’d be alone here, didn’t I?” She said with a smirk. “Now, about your flying lesson!”

Suddenly she was reaching under him, fondling his small balls and kissing him. Mr. Cake froze up in shock. Every instinct was on fire, ready to jump out and help his son! But then he heard Pound moaning and kissing her back. Pinkie took him over to the sofa, his little peen growing. He wasn’t big by any means, but he certainly took after his father. Pinkie then sat him down and lowered herself to take his small cock in her mouth. He moaned loudly in pleasure..

“That’s it, hold nothing back, let your auntie hear you enjoy it.” Pinkie said, going back down on him.

Pumpkin looked up at her father in surprise. He was watching intently. His son… and Pinkie Pie?

The pink mare was expertly sucking away, rolling her tongue around, taking his cock and ball into her mouth and pulling on them, making the colt moan louder. A hoof was now slipped between the mare’s legs, touching herself as she dripped onto the rug beneath her.

Mr cake’s erection was growing again and Pumpkin was feeling it swell. The filly bit into her hoof and tapped her father's chest, warning him. He looked down at her and realised what he was doing. He patted her on the head, trying to comfort her and closed his eyes, thinking of being somewhere else, picturing his wife playing bridge, a card game, simple, boring. Not thinking about how amazingly tight his daughter’s pussy felt around his cock. Not thinking about his son’s moaning as Pinkie slurped his cock noisily like a popsicle. Those were things he certainly wasn’t thing about.

Pinkie then climbed up onto the sofa and sat over the colt.

“Come on Pound. Let’s see if you can break your record of three before we get you home.”

Three?! Pumpkin and her father thought together. The pair of them barely had time for one together, if that. Where were they doing this to get so much privacy?! How long had those two been doing this? Was this why Pinkie got the clubhouse for the foals? This was to be her new… love spot?

Pinkie lowered herself down onto the colt’s erection. He easily slid into her and while he might not have been in her too deep, the whole taboo of the situation had Pinkie shaking and moaning as she rocked her hips back and forth on his lap. Pound rolled his head from side to side in ecstasy as he moaned out her name again and again. It filled the room as did the sound of the sofa, creaking.

Mr. Cake couldn’t focus, he was trying so hard to stay focused elsewhere, that his grip on his daughter had loosened and she started to slide down his rapidly expanding pole. She bit into her hoof to keep silent, and with the other she tapped her dad’s foreleg to get his attention. Realising his daughters silent distress, he held her tight again, holding her still. He hadn’t gone much further into her and after being on the head of his cock for so long the stretching only hurt a little in comparison, but pulling out was still out of the question.

Pound Cake meanwhile was fluttering his extended wings on the sofa, the tips curling up and his face awash with pleasure. Pinkie loved seeing the tell tale signs of an oncoming orgasm from the colt and within seconds he moaned and thrust up into the grown mare as he was taken over the edge.

“Oh yes,” Pinkie said, lust oozing from her voice. “There’s my little Pound pound. Now, it’s my turn for fun!”

With that, the mare stood up off the sofa and turned away from the colt. She lifted her tail and showed off her dripping sex to the colt. Pound knew what he had to do as he pushed himself up, his cock still hard and while standing on the sofa, he plunged himself all the way into her that he could.

“Oooh,” she moaned in pleasure, her eyes half lidded as she looked forward in a daze, lost in her own lust.

Mr. Cake watched as his son plowed into the mare, their hips slapped loudly together on contact, and Pinkie's moans were picking up in volume too. Despite himself, this was really turning the stallion on and being pent up for so long had him ready to bust, even in this scary situation. His cock was still in his daughter and he was so close, if he came, maybe his cock would shrink enough to pull out of her. But would Pumpkin stay quiet enough? He hoped so. Without words, he started to move the filly up his shaft to the point of where he could feel his flat head pull on her. Pumpkin started to panic as she felt the pain spike, but her father was whispering for her to stay quiet. He slowly pushed back into her, by only half an inch till she went tight again. Lifting her up, he repeated this again and again with each time she’d stifle a yelp of pain, keeping quiet and unheard over the sounds of her brother and Pinkie yelling and moaning. The sounds of slapping flesh continued as the colt, still too young for a cutiemark, buried himself into the full grown mare who was making higher pitched noises, begging him to go harder.

Pumpkin, with her mouth still covered, was slowly getting used to the feeling the longer this went on. And as long as her father kept going this slow, she could take it. Hearing her brother and Pinkie just on the other side of this wooden door was making her feel very horny as well. The filly reached up a hoof up for her father’s, which he was already using to balance himself. Realising she needed the support far more, he held and squeezed her hoof while his other kept ahold of her waist to control his own thrusts into her body. The pair of them were moaning silently in their throats as Pinkie continued to bellow from her’s.

“Oh yes! Harder! Harder!! OOH!” She held nothing back, and nor did her tiny lover. And soon he was on the verge of cumming again.

“P-Pinkie! Ah! I’m- Oh, I’m so close!” He said, exhausted.

“W-wait!” She shouted. She then stepped forward, letting the colt slid out of her and then laid on the ground on her back.

Pinkie, unknowingly to her had just put herself into a position where Mr Cake could now see her cunt clearly and when Pound Cake zipped down, he could see them both fucking from the perfect angle. This made the stallion almost reach his limit. His son’s peen going into the mare while she cried out in pleasure, her legs twitching, spread wide, and from the sounds of it, she was approaching her own orgasm. Mr Cake was thrusting harder into his daughter now and despite how rough he was becoming, Pumpkin held on, she was getting so used to it that it was starting to feel pleasurable, yet she was sure she’d be very sore in the morning.

“Yes, Pound, do it!” Pinkie cried out. “Rut me! Cum in my pussy!”

Fluttering his wings, he lifted himself from the ground and started to fuck her with as many hard deep thrusts as he could, pounding into her from the air, not a single hoof on the floor, pulling himself down into her as he tried to fly away for extra impact. This was his and Pinkie’s favourite position, and in seconds, the two were screaming out in bliss as they came together.

Pumpkin was biting her father's hoof as she also reached her peak, after all the hurt, the pain, the fear of being caught, the pressure built up inside her from her father hitting every right spot inside her and she hit her own climax, making adorable little squeals from her fathers cock as it pulsed inside her. Mr Cake, couldn’t stop cumming after hearing his own son bucking the mare he called his Auntie so hard, and then finishing inside her. He felt pride that his boy was so good and as such a young age. His cum filled Pumpkin with spurt after spurt so fully that when there was nowhere else for it to go, it dripped out her almost airtight pussy and slid all the way down his shaft and down onto the floor.

He was breathing heavy and sweating from the excruciating effort of standing on two legs while holding and fucking a filly. He gasped for breath and felt his cock soften, shrink. He thought he could probably pull out without hurting her now. Shifting his grip to hold his daughter under her rump, he lifted her up and off of his cock with a pop. As he did so, he hit her clit on the way out which caused the over-sensitive filly to jolt with pleasure and let out an adorable squeal. Immediately the filly covered her mouth and her father's blood ran cold.

Silence. Did they hear that? Maybe they were too exhausted? Pumpkin looked up at her father, he looked down at her, both of their hearts racing a mile a minute.

Click

The wardrobe door opened. Pinkie looked shocked and then smiled nervously as she took in the scene before her.

“So… errrrr… enjoy the show?”