Thirty One Nights Of Nightmare Night!

“No! No, I swear! It feels so much better if you take it all at once!” Scootaloo declared loudly.

“But doesn’t that make it worse for the morning afterwards?” Applebloom asked, concerned.

“Well, maybe. But it’s the best way really! I mean, if you worry too much, how will you have a good time in the moment?”

“I think I’ll just take it a little at a time. Rarity’s expecting me home early tomorrow and it’s a long walk. I don’t wanna go home in pain.”

The Cutiemark Crusaders all sat together in their old clubhouse. It was starting to become a little cramped for them as they were getting a little big for it now. They were entering their teenage years and they’d all grown so much in the last five years.

“Sweetie, you have to understand.” Scootaloo continued. “If you can’t take it, you’re going to have to force it down. Otherwise, you won’t really feel it.”

“O-okay..” Sweetie Belle took a hesitant breath, she steeled herself and then after letting go of it, she tipped the mug of cider up to her mussel and then began drinking heavily!

Scootaloo cheered her on as she raised her own mug of cider. Almost half way down, Sweetie spluttered and gasped for air as she pulled the drink away and coughed, evidently some of the drink going the wrong way down.

“Easy there, Sweetie,” Applebloom said, patting her friend on the back. “You okay?”

Sweetie coughed a few more times to clear her lungs before nodding. The young unicorn had spilled half her drink on the rug they were all sat on.

“Geez, girls. If you’re going to waste good cider, I won’t bother getting it for you next time.”

The young mare trotted over and took the mug from Sweetie Belle, then carried it to the wooden keg to refill it.

“Sorry, Spur. We’ll be more careful.” Applebloom said apologetically.

Spur was a friend of theirs who lived very far away. She was visiting Ponyville for a few days, a thing she’d been doing at least once a year, but it would probably be her last visit for quite a while. She was moving to another continent and didn’t know when she’d ever be back. So the crusaders organised a sleepover in their old clubhouse which was due for a complete overhaul. Perhaps it was time to hand it over to the next generation of ponies. The girls were getting so busy with their business, helping ponies discover their talents, that running it from a treehouse in an orchard was just getting out of the question. Rarity was expanding out of ponyville now and had agreed to let Sweetie run the Cutiemark business out of the Carousel Boutique from now on. It was in the middle of town, far more glamorous and would all together be more professional.

So to say goodbye proper, Applebloom had the idea for the sleepover in the Clubhouse. Scootaloo mentioned that Spur should get a cider for each of them to make it a real farewell party as a joke, but surprised the group when she arrived with a full keg of Sweet Apple Cider. Spur gave the refilled mug to Sweetie and then joined the girls, sitting in a circle.

“So, this is last night you’ll be together in this Treehouse, huh?” Spur said, taking a swig of her Cider.

“I’m gonna miss this old place. So many good memories.” Said Scootaloo.

“It’s just so sad to see it come to an end.” Sweetie pouted, taking a sip of her drink.

“Yeah, but it’s not like it’s going anywhere. It’s just… Younger foals could make so much more use of this place while growing up, and we’ve all already grown so much together.” Applebloom added.

The three murmured positively together, with Spur smiling at the group. She really liked hanging out with these girls, they made her feel young again, and yet here they were growing up, moving on and leaving the kids stuff behind. The pegasus looked to the window and saw that it was getting to the darkest part of the night. Spur stood and looked out the window to the inky blackness. Maybe, there was one last game they could play.

“Hey girls,” Spur said as she closed the curtains. “I know something we should do, to give this clubhouse one more fond memory.” They were all listening carefully to her. “Truth… or Dare!”

Applebloom giggled a little, turning pink and drank more cider to hide her face. Scootaloo’s eyes brightened up like this was the best idea ever, but Sweetie just smiled innocently.

“Oh, we’ve played that before.” The filly said. “Scootaloo dared me to get an ink cutiemark on my flank. I got in so much trouble because ink doesn’t come out of white fur easily.”

“Sweetie, she’s not talking about the foal version of truth or dare,“ The orange pegasus said, rolling her eyes. “We’re practically grown fillies now. Spur means a more… adult themed Truth or dare.”

Sweetie Belle’s looked confused before the realisation hit her and her eyes turned to pin pricks. Applebloom gave her a pat on the shoulder.

“Don’t worry, Sweetie. It’ll be fun! Just drink some more. It’ll loosen you up. I’ll go first so you can see that it’ll be fine, then you can go last, okay?”

The white unicorn quickly took a sip of the cider. The bitter taste wasn’t exactly to her liking, but everypony else was drinking it, but it was also starting to make her head spin a little.

“Okay, Spur, you suggested the game so you ask the first question.” Scootaloo said, pointing a hoof at Applebloom.

“Alright then. AB! Truth or dare.”

Applebloom didn’t hesitate.

“Truth!”

“Okay. Have you ever looked at your brother’s cock?” Spur said with a smirk. Sweetie almost choked on her cider again as Applebloom turned a deep shade of red.

“Whoa!” Scootaloo exclaimed, laughing. “Starting out strong, aren’t you?”

“I guess I don’t hold back when I’ve been drinking.” The young mare said. “Plus, I wanted to start with something big so Sweetie Belle would really understand the game.” Spur then focused her attention on the yellow filly. “So, speaking of big, tell us. Have you?”

Applebloom took another drink before she looked from the floor to the brown pegasus sitting across from her.

“Yes.”

“Ohh hoo!” Spur said happily. “Well, tell us. In detail, what did you see? Does he live up to his name?”

Scootaloo was also leaning in close with a big smile on her face.

“Well…” Applebloom hesitated and then put her mug down. “Okay, fine. We were in a bath together, I was very young and back then the three of us would always bathe together in a large tub in the yard. I still didn’t know that colts and fillies were different at this point. I mean, I knew but, it meant nothing to me. Anyway, one time my sister got out of the tub and Big Mac kept staring at her while she was drying off. He’d never stared at her like that before and… I think she knew he was watching. I didn’t understand what was going on back then, but when she left, my brother told me it was time to get out of the tub. That’s when he stood up and turned away from me but I saw it. And he was...” Applebloom took another swig of her drink before continuing. “Erect.”

“Oh wow!” Spur had a huge grin on her face. “So… how big was it?”

“...Umm... “ Applebloom said nothing. But with a cheeky grin she held her hooves apart a wide distance, wider than her shoulders.

“And around?!” Scootaloo asked excitedly, also grinning as wide as Spur.

“Well... you couldn’t fit it in your mouth, that’s for sure!”

The two Pegasi squealed in unison and covered their mouths before descending into giggles.

”Oh my Celestia!! I’ve got to see him before I leave!” Spur said with desire in her eyes “Think you could arrange a one night stand for me, AB?”

“Spur!!” Applebloom Protested.

“What?! I’ve got a thing for red stallions. Sue me.”

“Yeah, well maybe you should just go after your own brother then!” The earth filly said with a chuckle.

“I did once.” The room went silent as all eyes turned to Spur, as she casually took another drink of cider. “Next question girls. Come on AB. I asked you, now you ask somepony.”

“Alright then. Spur. Truth or Dare!”

Spur flicked her curled mane out her eyes and then looked Applebloom dead in hers.

“Truth.”

“Right, what did you mean you went after your brother once?!” Applebloom knew there was no other question to ask. Not after that bombshell.

Spur took another swig and held it before swallowing, as if delaying answering on purpose, keeping her younger friends on edge. She was getting a good buzz going too, and looking about, the other fillies were also getting messed up. Sweetie in particular was such a shade of red that Spur couldn’t tell if this was from embarrassment or if it was the alcohol getting to her. She seemed to be taking a sip every few seconds, just to hide her face.

“Right, so… we live in the middle of nowhere. We almost never get visitors or friends to meet. Especially not our own age, always adults. It’s why I love to hang with you girls so much. You’re great!” They all smiled warmly at each other and gave their support back too, saying they like being with her just as much. She didn’t treat them like kids. ”Well, I was in my first heat and there weren't many options. I’m sure you’ll all become very familiar with that soon. Well, I got desperate and I knew that stallion cum was the best relief for it.” Sweetie heartily took another swig of Cider ”Now, my brother is an idiot and knew nothing about what’s right and wrong when it comes to sex. And that night I convinced my brother to help me out, he’s a dummy but I still love him and… well… he lasted all of five seconds.”

Applebloom and Scootaloo laughed hard at that.

“Oh geez!” Scootaloo said, still laughing. “Please tell me he had the decency to help finish you off with his tongue, at least.”

“Nope, he fell asleep almost instantly, worst sex I ever had. But I'll tell you what. It’s true. Stallions cum really does put out the fire. That or my disappointment really crushed any other feeling. Seriously, Bloofy was a much that he was.”

“YOUR PET!?” Sweetie Belle squeaked lowering her empty mug, which might have been empty for a while. Spur laughed and took the mug from her to refill it, along with her own.

“Yup. I tell you, once that little fella gets excited, he can really drill up a storm!” Spur gave the mug to Sweetie with a wink and then sat down with her own. “Right. I think Sweetie should ask the next question. Scootaloo, it’s your turn.”

The orange pegasus turned to look at Sweetie, ready for whatever. Sweetie on the other hoof wasn’t. She didn’t know what to say! Everything had been so dirty till now, she’s no experience with sex and her ex-boyfriend never did anything romantic with her. So she asked the only thing she could think of.

“Umm… Have you… who was the first ever boy you kissed?”

“Ne, no Sweetie,” Applebloom interrupted, slurring her words a little. “You’re supposed to ask Truth or Dare.”

“Nah, it’s fine, Applebloom. I was gonna say Truth anyway. I doubt Sweetie could think of a good dare. No offence!” Scootaloo took another chug of her drink. “But lemme double check the question. First ever boy, or… first ever?” The orange filly smirked at the ponies looking at her.

“No way!” Spur said aloud with a grin. Scootaloo laughed and then answered.

“My first ever KISS was with a mare-”

“Rainbow Dash.” Applebloom said quietly, but loud enough to be heard before drinking more.

“That obvious, huh? Well, yeah, it was. I’d just gotten my cutiemark and after we went our separate ways that day, Dash caught up with me and said she’d been saving a gift for me on this very day. It was there that she took me to the highest cloud and we started making out. I was shocked at first, but it took only a second for me to kiss her back. And it didn’t end there...”

Scootaloo trailed off her sentence but Spur was right on her.

“And neither do you! Keep talking.”

“Well... “ Scootaloo smiled, a blush coming to her face for the first time tonight. “You’re a pegasus, Spur, so let me ask you. Have you ever used a cloud dildo?” Applebloom and Sweetie’s jaws dropped. Spur shook her head. “It’s the most amazing, tingly feeling. I couldn’t keep still! Dash had to sit on my chest and hold my legs together cause I wouldn’t stop kicking. Even stuffed her tail in my mouth to stop me screaming so loud. But that’s nothing compared to when she made one from a thunder cloud. I had to spend a weekend at her house just to walk straight. Best weekend of my life!”

“That sounds so hot.” Spur said, taking another drink.

She was getting so turned on by these stories, and knowing Scootaloo had lost her virginity to an older mare at such a young age was just having her wish she could have some alone time right now. Sweetie Belle was wishing she could have alone time too, but for a different reason. It was her turn next.

“Sweetie?”

The white unicorn squealed aloud, realising that she was being addressed by Scootaloo.

“It’s your turn. Truth or Dare?”

There was no way she’d be about to share such secrets with her friends. What if they asked her about Rarity? Of course they would, but she didn’t wanna share private stuff about her sister. She might get in trouble for it, but she decided that maybe she'd be better off getting another ink cutiemark from Scootaloo again..

“D-dare.” Sweetie said nervously. Every pony was grinning, but none more than Scootaloo.

“Brave!” Scootaloo said happily. “Okay! I dare you to… show us all your cooch!”

This time it was Applebloom who gagged on her cider. Spur looked between Scootaloo and Sweetie, but said nothing. The white unicorn might as well have been a red one because you couldn’t tell with how embarrassed she was.

“M-m-m-m-my… C-c-c-...”

“You know, pussy, vagina, cunt, flower, tight cock holder!” Scootaloo said mischievously, giggling a little at her lewdness. “You wanted a dare, you have to do it now!”

“Umm, you think maybe we’re talking this too far?” The yellow filly asked.

“Well, that depends on Sweetie.” Spur said “If she declines the dare, she’s out of the game. However, if you don’t feel comfortable doing it alone sweetie, I’ll do it with you. Just to make you feel comfortable.”

Sweetie Belle looked at Spur who was just sitting in only a faded Appleloosa State Fair T-shirt. Sweetie’s nightgown was covering her whole body. She’d have to physically lift it to show herself off.

“I don’t know...” Sweetie said, unsure.

“Aww, come on. What are you worried about? Just take another drink, then show us. Just for ten seconds.” Scootaloo tried to be more encouraging, but sweetie was still nervous.

Ten seconds? Could she do that? She looked to Spur who gave her a nod and sat back, hind legs apart with her tail up between her legs, the only thing keeping her modesty. Scootaloo and Applebloom sat in silence, looking between the pair.

“Hey Sweetie.“ Spur said, getting her attention. “It’s the last time we’ll be together, perhaps for many years. Let’s just go wild with our girls-only night. We’ll never get to do this again. And trust me, it’s only scary the first time you show off. And we’re all close friends here, right?”

The unicorn nodded. She didn’t wanna be a wet blanket. This was supposed to be a fun and crazy night. Besides, they were all girls and this was just a dare. She looked at her cider and then drank her entire mug in one go. Scootaloo was impressed, and more so when Sweetie used her magic to lift her nightgown up to her waist, sat on her haunches and then spread her legs for all to see.

Sweetie Belle wasn’t looking but she could feel all eyes on her small kitty. Though the thought of calling it that still, made her feel like a foal. She was in her teens now. But… her friends here were the first ponies to ever look at it like this.

Scootaloo scooted a little closer to her friend’s pussy. It looked so smooth and soft. Untouched and small. Nothing like her own, and certainly nothing like Dash’s. This was what a pure virgin’s pussy looked like.

Applebloom’s eyes shifted from Sweetie’s cooch to Spur’s who was also showing herself off. The young mare had a rather nice pussy too, much more pronounced than Sweetie’s. In fact, she was sure that Spur’s was actually wet. Was she getting turned on by this? The yellow filly had masturbated before using a hoof, so she knew what she was like down there when horny but Spur’s looked more… spread, like she was wanting something. Then the thought of her brother sticking his cock inside her friend made its rounds in her head, spreading her cunt open wide and making her twitch. The teal maned pegasus saw Applebloom staring and gave her a wink. A wink that made the farm filly blush and feel very lightheaded.

Sweetie decided that she’d let them look enough and then sat up, lowering her nightgown. She sat properly and found herself nose to nose with Scootaloo who’d gotten very close.

“Umm... t-that’s it… That was all the dare was, right?” Sweetie asked nervously looking away.

“Oh! The dare, err, yes. Yes, that was all.” Scootaloo said, looking away too and then returning back to her place to re-complete their circle. Spur slowly closed her legs, but not before giving Applebloom more of a show by touching her wet cunt while the other two weren't looking and spreading the slick wetness up her inner thigh, mouthing the words. ‘Dare’

Applebloom suddenly stood up with her empty mug, completely flustered.

“W... we sho-, Whoa!” She wobbled a little but just kept her balance. Sweetie Belle jumped up to grab her, but standing up that fast also made her light headed.

“Oh wow! Umm, m-maybe, umm… We’ve drunk enough?”

“Aww, but it was just getting interesting.” Spur said with a tinge of disappointment and a little seductivism that only Applebloom picked up on, the filly laughed despite herself, a huge grin plastered on her face.

“Yea, but... I don’ think I... I can think straight. Let alone stand.” She let out another laugh and then looked to Scootaloo who was finishing off her mug.

“I gues-sh you’re right. It’s gotten very late.” Scootaloo starting to feel the cider’s effects too.

Spur smiled in spite of herself wanting more, but maybe it’s for the best, before they took things too far.

“Hey girls. Thanks for tonight, this was great.”

Applebloom and Sweetie then dashed over to give Spur a hug, though she had to hold them both up. Scootaloo though was playing macho and just headed over to the keg, until getting pulled in by Sweetie's telekinesis to the group hug. Scoots sighed and then joined them propper before they all got ready for bed.