Pipp's Holiday Snuggle Session

by AndrewsArchive

Rating: everyone
Tags: Anon, Second Person, Pipp Petals, My Little Pony: A New Generation, Romance, Self Insert, Slice of Life, Human
Length: 1312

Pipp gives you your Winter Wishday gift a little early. You and her cuddle each other afterwards.

While you and Pipp wait patiently for Sunny and the others to arrive to the Crystal Brighthouse, you noticed that she's more eager than she usually is about something. You would soon find out when she can't handle her patience for another second.

Published 2023-12-30 23:20:01 UTC
Last updated 2023-12-30 23:20:01 UTC

Here we go again

Winter Wishday was nearly upon you and the ponies of Equestria in a few days. The soft cold snow falling onto the ground. The night sky gave a relaxing aura. And the colorful lights that shone through Maretime Bay was a sight to behold.

You had made your way to the Crystal Brighthouse. You were excited for the upcoming holiday because of how much it reminded you of Christmas. And you were most excited to celebrate Winter Wishday with your pony friends. And more specifically, your marefriend Pipp Petals. Not too long ago, she had snuggled with you to help you with your sleeping problems. And since that day, you and she have cuddled more often because of how nice it truly felt being in each other's embrace. Now you and Pipp had made your way up to the Crystal Brighthouse. You open the doors and the two of you walk inside to find nopony else in there minus you and her.

"Looks like Sunny and the others aren't here yet." You spoke.

"Oh, it's alright, love. We can wait for them." Pipp said while smiling a little wider than usual.

She looked quite excited about something. You could tell by her tapping her hooves on the ground really quickly as well as the big on her face being dead giveaways. Not to mention, you noticed she was almost like this the past few days. She looked like she was wanting to do something, but she was having to hold back.

"Pipp, are you alright?" You ask her, raising an eyebrow. "You've been a little weird for a while..."

"Oh, well um... I..." Pipp stammered while sweating as she tried to come up with an answer. She eventually groaned loudly now seeing she couldn't hide it any longer. "UUUGH! To hay with it! I can't wait another day for this!"

Before you could ask, Pipp suddenly pulled out what looked to be a medium wide present and she held it out to you.

"I... err... wanted to give it to you under the Wishing Star... But... I may have gotten a little impatient..." Pipp laughed while scratching the back of her head.

"You want me to open it now?" You ask. "I don't know... it is a little early..."

"Oh, come on, love! I can't wait another minute!" Pipp replied, looking into your eyes with those puppy eyes again. She knew how to win you over easily.

"Alright, if you insist." You replied.

You took the gift from her and started unwrapping it. You then got a good look at your gift. It was a new set of pajamas with a pink and gold color scheme and with Pipp's cutie mark embroidered on the shirt.

"Well, whataya think?" Pipp asked. "I had Izzy sew them up for me."

"They're beautiful, Pipp." You smiled at her. "Thank you so much."

"How about you put them on now so we can test them upstairs." Pipp replied as she looked at you flirtatiously.

You decided to do what she said and started to undress yourself while Pipp looked away and covered her eyes while you did so. Once you put them on, you noticed how soft they felt on your skin. As if you were in a bed wherever you went with them on.

"Wow... these things are cozy..." You commented. "Izzy really did do a good job on them."

Pipp turned around hearing you as she squealed seeing you wear them.

"Eeee! you're so adorable in them, love!" Pipp said as she took out her phone to take a selfie with you. You and her both smiled as she took the photo, semi-blinding you from the flash. Pipp then put her phone away afterwards as she looked back at you.

"So, what now?" You ask.

"I said we were gonna test them upstairs, did I?" Pipp replied. You knew exactly what she was talking about as she flew upstairs to the shared bedroom of her and her friends with you in tow. Once you got upstairs, you saw her sitting on the edge of her bed like she did before.

"Remember when we started cuddling for the first time?" Pipp asked you.

You nodded in response, "I couldn't thank you enough for helping me with my weird sleeping problems."

Pipp then put a hoof gently right up to your cheek. "Well obviously! No alien boyfriend of mine is gonna suffer when I'm around!"

You and Pipp both laughed in unison as she spoke up once again. "Anyway, you ready for another cuddle session, love?"

In response. You then scooped up the short pegasus and held her in your arms. Pipp let out a small gasp as her rear legs flailed a bit from your sudden action. You carry her to the end of her bed and lay on your back with Pipp now resting upon your chest. Pipp was still in shock from what you just pulled before eventually shaking it off and giggled.

"I'll take that as a yes then." Pipp said before nuzzling herself head onto your chest as she spread her hooves around your body. You and she were now in a loving embrace. Feeling safe in each other's arms like nothing could ruin it. Pipp then spoke up again.

"Hey, love?"

"Yeah?"

"Wanna try new positions this time around?" She asks. "We can do more than just have me on top of you, y'know?"

You understood that you and Pipp mostly have just been cuddling with her on top of you every time. And you felt like you wanted to spice it up every now and then. So, you nodded your head in agreement.

"Yeah, nothing wrong with variety if you ask me."

Pipp smiled at your response as you and her tilted to the left side of the bed, taking her with you. You and she were now laying on your sides with Pipp still snuggling up to you. Her head was now under your chin as you stroked her back. A small yawn escaped her mouth as her eyelids started to get heavy. Before you could say anything, Pipp had succumbed to slumber as you hear her softly snoring away while holding you tightly.

You smiled down at the small pegasus who was nestled softly next to you, her right cheek squished against the mattress. She had never looked so adorable and sweet before in your life. You reached your right arm to Pipp's mane and spread your fingers into her purple wavy mane, Feeling the soft silky touch you were used to. You then noticed that your eyelids also started to get heavy as you let out a yawn. With nothing left to do now, you close your eyes, eventually submitting to the inevitable slumber.

"Pipp? Anon? Are you two up there?"

"Nonny? Pipperoni? You two playing hide and seek?!"

Sunny and Izzy called for you and her as they trotted up the stairs to the bedroom with Zipp, Hitch, and Misty behind her. They had just entered the Brighthouse a couple minutes ago only to find you and Pipp not downstairs.

When they reached the doors and opened them, the five ponies were met with you and Pipp both sound asleep on her bed. It wasn't the first time the five of them had caught the both of you cuddling each other. They all quietly giggled at the sight.

"Awww~ They look so cozy cuddled up to one another!" Izzy whispered.

"Yeah, we should probably let them sleep." Zipp replied.

Yeah... they do look cozy..." Hitch replied as they quietly made their way downstairs. Not wanting to disturb you and her.

Author's Note

Merry belated Christmas everyone and Happy New Year!

I wanted to get this out before Christmas, but writer's block had to screw with me. :ajbemused: