Winter Night Snuggles

by AndrewsArchive

Rating: everyone
Tags: My Little Pony: A New Generation, Self Insert, Mane 5, Human, Anon, Slice of Life, Second Person, Romance
Length: 2434

Why would you want to cuddle with one pony when you can do it with five?

While relaxing at the top floor of the Crystal Brighthouse, Sunny comes up to give you some company. Tonight, however felt special to you for a reason you don't know why. But when a giant gust of wind forces you and her inside, you'll find out why tonight feels special when the five ponies decided to make a tradition for you.

Published 2023-12-06 07:10:01 UTC
Last updated 2023-12-06 07:10:01 UTC

The Perfect Tradition

It was a beautiful wintery night in Maretime Bay. You stared out from the balcony of the Crystal Brighthouse into the night sky which was filled with snow falling from the clouds and even the Aurora borealis which happened in Equestria more than it did back on Earth. You watched the town from afar as it was filled with colorful lights and many ponies celebrating the upcoming holiday known as Winter Wishday, otherwise known as the ponies’ version of Christmas.

You couldn’t help but feel at peace right now. You may be the only human in Equestria right now. And the chances of you returning back home are slim to downright impossible. But despite those current stressors, they aren’t affecting you right now. Because just like Christmas, Winter Wishday was to be celebrated with the ones you cared for. And you get to share that with the six ponies who made you feel welcome here when you first arrived here. Those ponies being Sunny Starscout, Izzy Moonbow, Hitch Trailblazer, Pipp Petals, Zipp Storm, and Misty Brightdawn.

Speaking of which you suddenly heard the sound of the elevator rising up to the floor you were at with Sunny Starscout there as she noticed you and smiled.

“Oh, hi there, Anon!” She said as she trotted over to you. “What are you doing up here?”

“Oh, nothing special, Sunny.” You replied. “Just enjoying the view of the night sky.”

“Aw, that’s nice!” Sunny said as she was now right at your side, “It really is pretty tonight. Well, every night is! But this one does stand out a bit more… I just don’t know why…”

You couldn’t help but let out a chuckle at that, but she did have a point. Tonight, really did feel special than any other night this month. Even you didn’t know why this was the case either. But whatever the reason was, you decided not to think about it too much.

“So, why did you come up here?” You ask the orange earth pony.

“Well…” She scratched the back of her head. “I… didn’t want to make you feel lonely up here, Anon.”

“Oh… well thanks, Sunny. I appreciate it.” You respond. You were touched to see that she wanted to come up here to spend some time with you while also hanging out with her friends too. You couldn’t help but feel a connection with not only her, but with the four other mares in the group.

Izzy was super adorable whenever she was happy. You loved her creativity, and she always gave you a smile when she was around. Pipp was also just as adorable because of how sweet she is and her being a little shorter than the rest gave her a bigger advantage. Even if she probably wouldn’t admit it, Zipp also had her moments of being cute. She was also fun to be around with her detective work. Misty also had a huge advantage of being adorable because of her being a tad awkward compared to her friends. But you alongside them always made her feel welcome. And Sunny was just as sweet and cute as them all. Her hopeful personality gave you a sense of hope of your own.

You were pulled out of your thoughts as a giant gust of freezing cold wind suddenly blew right into you and Sunny. The small snowflakes hitting your body and face. You wiped the snowflakes off your face as you turned to Sunny who also did the same thing as you.

“Whoa. We should probably head inside now before it probably becomes a blizzard out here.” She spoke. You nodded your head in agreement as you and her walked towards the elevator and back down to the second floor where all the beds of the five mares who lived here. You felt a blast of warmth from the inside of the Brighthouse as you noticed Izzy, Zipp, Misty, and Pipp all talking amongst themselves.

“Hey ponies! I got him back down here!” Sunny said as she got their attention. The four ponies all looked up at you and her as they greeted you.

“Hey there, Nonny!” Pipp said, “I thought you’d never come down from there!”

“And about time, too.” Zipp said with a smug grin on her face, “You trying to freeze yourself up there or something?”

“What?? Can’t a guy enjoy the scenery of a night sky?” You replied.

“Yeah, you can, silly!” Izzy beamed, “But you were up there for too long!”

“Well, you can thank the weather for bringing me down here.” The five ponies all giggled in unison at your statement.

“So uhh… what are we all doing tonight?” you ask.

“Well, we just finished up some small traditions we sometimes do in winter. And Hitch is staying at his grandmare's house for a while with Sparky.” Sunny said, “So… We kinda wanted to know if you have any traditions that you humans do?”

You felt stumped as you tried to come up with something with no success. You never really did any traditions for Christmas besides being with your loved ones. And anything that any other person would do just felt so generic. You wanted something new, but you couldn't come up with anything.

“I…. Umm…” You tried to find your words. “I…. Well…”

“Hey, it’s okay if you don’t have anything.” Misty reassured you. “I mean… I’m kinda new to all this as well. So… you’re not left out.”

“Yeah, don’t feel bad, bud.” Zipp reassured you as she put one of her front hooves around the back of your neck. “Besides, what if we made one for you?”

Pipp gasped as she smiled, “That’s a great idea, sis! Ohh, I always wondered what type of unique traditions humans do than us ponies!”

“Well… what exactly do you ponies have in mind?” You ask. The five mares all thought of ways to give you a tradition for your own for Winter Wishday. Many ideas were thrown such as singing some carols, snowball fights, treat baking, and the list goes on. But none of them really piqued your interest. But then, Izzy got a bright idea as she spoke up.

“I got it!” Izzy said, “What if we all got together and slept in one bed!”

“You mean we’re gonna all cuddle one another for the whole night?!” Pipp gasped before squealing in excitement as she flew in the air a bit. “That is sooo a good idea! We’ll all basically be snuggle buddies!”

“Whoa, woah, okay! That’s a bit much there, Iz.” Zipp said, sounding a little reluctant. “I mean, it just doesn't fell righ-… Oh to hay with it! I’ll do it.”

“That’s the spirit, Zipp!” Pipp complemented her older sister stepping out of her comfort zone.

“Well…” You replied, I suppose it wouldn’t hurt to cuddle with you girls…”

The five ponies all smiled as you agreed to do so. You felt a bit awkward knowing you would be snuggling with five different ponies. But at the same time, they were all equally adorable so you couldn’t help but want to. Misty then looked toward the beds and realized that something was not right.

“Ummm… I hate to have to point this out…” Misty spoke up, “But, I don’t think any of our beds might not be big enough to hold all six of us. I mean… I know we all sat together to watch that reel when I first moved in here, but Anon wasn’t there with us…”

The ponies all looked to their respective beds to see if they were all big enough to have you and the five ponies all be able to sleep together. But unfortunately, none of them seemed to be big enough to fit all of you. And you doubted the couches downstairs were even good enough for that.

“Looks like we might not be able to sleep together after all…” Sunny said as her ears drooped.

“Aww seriously?” Pipp groaned, “Uughhh! I knew I should’ve gotten that wider mattress when it was on sale!”

“Well… what can we do, now?” You ask. Izzy on the other hand felt a light bulb flicker over her head as an idea popped into her head.

“Oh, don’t worry, everypony!” Izzy said, “I got just the thing for this!”

The lilac unicorn dashed over to her side of the room and was rummaging through her belongings in search of whatever it was she was looking for. You and the four other mares just looked at each other with confusion over what was just happening. Izzy then returned to the circle with a deflated air mattress and an air pump tucked under her hoof.

“If found this king-sized air mattress in a lost and found a couple weeks ago and I felt like it would come in handy sometime soon. And soon is now!” Izzy smiled.

“Well, that’s oddly convenient.” Zipp commented. “But is it big enough to fit ALL of us?”

“We’ll have to find out, Zipperdoodle!” Izzy then hooked the air pump into the mattress and quickly started pumping air inside of it. And by that, you mean she did it incredibly quickly as the mattress inflated within a matter of seconds. And she was right, it was big enough to fit six ponies. Or in this case, five ponies and one human.

“This’ll work perfectly, Izzy!” Sunny said before letting out a soft yawn. “Hehe… guess we better hurry and add some pillows and blankets to this.”

The five mares then each went to their respective beds and pulled off some of their blankets and took their pillows along with them and set them onto the mattress. Making it look like a cozy heaven that any creature would want to sleep in for all eternity.

“So… um… who’s going in first?” You ask.

“Well, you are obviously!” Pipp said with a wicked smirk on her face while rubbing her hooves as if she were some villain.

Before you could respond, you suddenly felt hooves grabbing ahold of you by your waist and hoisting you up a bit. You then were pulled into the bed with the pony who took you with them as you now lay on your left side, making the ponies all giggle at what had just happened. You look up to see Zipp smirking down at you. Revealing she was the one who pulled you into a spooning position in the bed.

“You left yourself open, Anon.” Zipp said to you in a flirty tone.

“Alright, very funny.” You replied unamused at what she just pulled.

“Well, you two look cozy!” Sunny giggled, “But I’ll join in next!”

The orange earth pony trotted over to the bed and crawled up to you as she cuddled up right to your chest. Her face nuzzling right up to it. You couldn’t help but smile a bit at her adorable face as Sunny then wrapped her hoof around you and pulled herself even closer to you. You did the same as you felt the body warmth of Zipp behind you and Sunny in front of you.

You then felt something near your free arm which was actually Pipp wriggling herself under said arm as if she wanted it to be wrapped around her back. Once she got halfway through, her soft pink cheek was touching yours as she rested nicely onto your body.

“Ahh… There we go~” Pipp said. “Can’t have you two enjoy all the fun for yourselves.”

Zipp rolled her eyes at her sister’s comment while Sunny just snickered. “Hey, we were gonna let you join in too!”

Misty got behind Sunny as she snuggled up until her nose was basically touching yours. Her long brightly colored mane getting in your way a bit as she relaxed into the cuddle pile.

“Is... umm… Is this good enough?” She replied awkwardly.

“Don’t worry, Misty. You’re all good…” You assured the blue unicorn. The last to join the cuddle pile was Izzy as she got on top of Misty and Sunny by crawling on top of them instead of hopping on top of them and potentially knocking the air out of you and them. She laid her head down upon the warm bodies of you and the other ponies.

And here you are now. Cuddling with five different mares on an air mattress. Each sharing their body heat with you. With Sunny and Zipp pulling the blankets up close to your upper body. Izzy using her magic to turn off the lights as it was nearly pitch black in the room. The night sky illuminating the room a bit.

A white flash suddenly happened, blinding you for bit. When your vision returned, you look at the source of the flash, only to see Pipp holding her phone up revealing she had snapped a picture of everyone on the mattress.

“Pipp! Seriously?!” Zipp said, annoyed by her younger sister.

“Whaaaat?” Pipp responded, “I’m not gonna post it online this time…... Maybe~” Zipp just groaned while Pipp giggled as she put her phone away and rested back down again.

For the next few hours, you and the ponies all just laid peacefully on the air mattress. Talking about what everypony would do for the upcoming holiday or how cozy they felt against one another. It made you wish this would never end…

“Hey, girls…?” You spoke up.

“Yeah?” Sunny replied first.

“What’s up?” Zipp said.

“Do you think we could do this more often outside of this month?” You ask. All ponies just smiled at you in response. Giving you closure that this cuddle pile would happen more often.

“I like the way you think, Nonny...” Izzy said, nuzzling her head deeper into the pile.

“That sounds lovely…” Pipp said while yawning.

Before you knew it, all ponies were all asleep peacefully. You were the last to finally join them as your eyelids grew heavy. You felt so safe with these ponies cuddling all around you, like they were wanting to keep you close to them. It made you realize why tonight felt so special…

It was the start of a deep connection with these five ponies.

Author's Note

Here we are! Another fic down. Hope you all enjoyed this 5-way cuddle fest!

I won't lie. I always had an idea for a four-way G5 pony x human story. One was a sad story, the other was a similar concept, except it wasn't holiday themed.

See you all when I make another Human x G5 Pony fic someday soon.