
Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/5540162.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      F/M
  Fandom:
      My_Little_Pony:_Friendship_is_Magic
  Relationship:
      Princess_Luna/Pipsqueak
  Character:
      Princess_Luna_(My_Little_Pony), Pipsqueak_(My_Little_Pony), Dinky_Doo,
      Derpy_Hooves, Time_Turner_-_Character
  Additional Tags:
      Straight_Shota, Insomnia, Cowgirl_Position, casual_nudity, Fluff_and
      Smut, Alternate_Universe_-_Human, Extremely_Underage
  Stats:
      Published: 2015-12-26 Words: 2885
****** An Enchanted Evening ******
by TiberiusPonificus
Summary
     Poor Pipsqueak is having trouble getting to sleep, when he is
     suddenly whisked away to Princess Luna's chambers. Luna says she has
     a solution for his woes, but what could it be?
     Note: Thinking of adding more to this story and taking it out of the
     current series. Should I do it? Comment with your answer.
Notes
     This is one idea I've had for a while, but wasn't totally sure how to
     pan it out. I hope I've done a good job of it, and that you enjoy
     this.
No matter how much you try, you can't seem to get yourself to sleep. It has to
have been an hour since you've been put to bed, but you don't feel the least
bit sleepy. You want to sleep so you won't feel so tired in the morning, but
it's just not coming to you. You toss and you turn, trying to to get yourself
in a more comfortable position, but that doesn't seem to help either.
Defeated, you throw off your sheets and hop off the bed. In troubling times
like these, there's been one thing that's brought you solace: Looking at the
moon. Princess Luna has long been the one you've thought of since your first
Nightmare Night when she visited. Whenever you saw the moon, you thought of her
and how much fun you had. Maybe thoughts of her could soothe you to sleep.
You walk over to the window, the cold night air delivering a shock to your body
that only makes you feel more awake. Your wool pajama onesie provides ample
coverage from the cold, however, so it's not a big problem. Gently, you unlock
the shutters and open them wide, giving you a nice view of the full moon.
The light from the heavenly body shines through the open window, only making it
more beautiful. You sigh wistfully and rest your head on your hands, thinking
of the princess. Thinking of how lovely she looks, you feel as though you're
floating. You can't even feel your feet on the ground.
Looking down, you find that you're actually floating! You can move your body,
but you can't get back on the ground. As you wonder why this is, the zipper on
your onesie starts to move down, unzipping your pajamas! The garment slips off
your shoulders and is completely removed, falling to the floor. Left in just
your white briefs, you clamber to try and retrieve your pajamas to no effect.
Instead, you start slowly flying around your room, until your body is directed
towards your window. You close your eyes, fearing pain, only to feel a tugging
at your waist.
You open your eyes to find you've been taken to the air above the town. The
people still awake and moving about don't seem to notice you. You're about to
shout down to the people to help you, when you peer down at yourself. That
tugging you felt a few seconds ago was your underwear falling off, leaving you
stark naked flying above the town. Suddenly, your embarrassment overrides
everything else, as you helplessly cover yourself and watch as you fly over the
homes and shops and wonder where you're going.
Higher still, you pass by the edge of town and over the grassy fields. Looking
ahead, you can see the spires of Canterlot Castle looming in the distance. As
you get closer, you start to slow down, leading you to believe you're getting
close to your destination. But why would you be flying to Canterlot? Is someone
drawing you here with their magic?
Finally, you fly above one of the taller spires in the main castle where you
make a temporary stop. There's a small balcony at the top, with a doorway
leading inside. You then begin to float gently towards this balcony, as though
whoever's carrying you is being careful not to hurt you. As you reach the floor
of the balcony, you are released from the magic, dropping you on your feet.
With nowhere else to go, and the cold of the night only reminding you of your
nudity, you walk cautiously into the doorway. In the room it leads to, the
floor sinks at a circle, creating a place to sit. The soothing nature of it
allows to relax and walk normally, your hands at your side. Aside from that,
there is a fireplace, a bookshelf, and another doorway leading deeper into the
room. Curious to find out more, you enter the doorway.
Inside, the first thing you find is a grand bed. Much larger than your own, its
sheets look incredibly soft, and the frame is very well decorated, complete
with a crescent moon on the top of the headboard. Before you can figure out
who's room this is, a lovely voice calls to you from behind.
"Good evening, young Pipsqueak."
You jerk around to look behind you, and there she is: Princess Luna, in all her
glory. Her velvet blue hair flows gently behind her, matching with the long
robe she's wearing. A gentle smile decorates her face as she comes towards you.
Was she behind you the whole time?
"Princess Luna!" you cheer. "Did you bring me here?"
"Indeed," she answers. "I sensed you were having trouble getting to sleep."
"Y-you did?" You ask bashfully, embarrassed that she was giving this much
attention to you. But that isn't the most important question right now.
"Um...did you take my clothes off?"
"I did," she plainly answers, "because I find that sleeping nude brings about a
kind of comfort that's incomparable. Especially when it is with another."
"Really?" you ask. It's certainly something you've never given thought to
before, but if a princess thinks there's something to it, then...
"Indeed," she answers. "Would you like to see if that will bring you rest?"
"You would...do that for me?"
"If you'll allow it," she says.
"Of course I do! Um...your highness," you straighten yourself properly,
remembering that she is royalty.
"Good." With a wave of her hand, the sheets of the bed draw back, revealing the
blue cover of the mattress. You look with awe at her magic as you climb onto
the bed and lay down. Meanwhile, she reaches for the opening in her robe,
spreading it apart and letting it fall off her shoulders onto the ground. You
tense up and your eyes grow wide at the sight before you.
The light in the room illuminates Luna's naked beauty. Her slim figure,
gorgeous legs and proportionate breasts are a sight to behold. Your eyes look
over every part of her body, particularly between her legs, where a well-
groomed patch of blue hair covers her womanhood. You try not to stare too much,
and nervously look aside.
"Are you well, my child?" Luna asks.
"Um...well, it's just..." you stammer out.
The other boys at school like to talk about what girls look like naked. You've
never really given any thought to it, though. Dinky takes baths with you all
the time, after all, so it was never that big a deal to you. Seeing Princess
Luna's naked body, however, is giving you some idea as to why it's such a big
deal to them.
"Are we...really going to sleep like this, Princess?" you ask.
"Are you scared, dear Pipsqueak?" she asks back as she climbs on to the bed and
lays next to you.
"Oh, no. I could never be scared of you," you tell her, turning yourself to
face her. "But..."
The way she's laying, her chest is in front of your face, and you can't help
but stare. The whole experience is leaving your heart racing and between your
legs feels...tingly? You're not sure what to make of all this.
"All is well, child," she says with a smile. "You have never had this
experience before. Please...feel free to explore this body to your heart's
content."
"You mean it?" you say, trying not to sound too excited. You had heard the
other boys talk about how nice a woman's breasts are, but none have ever known
what they felt like.
"Of course," she answers. "I want you to be comfortable, child. You should
become familiar with this body if you're going to rest with it."
"Um...okay, your highness," you nod and reach out to grip her breasts. Your
small hands barely cover them, but they don't feel as stiff as you thought
they'd be. Rather, somewhere between firm and squishy, as some of her breast
seems to seep between your fingers as you squeeze. Luna's face twitches
whenever your grip tightens, and you worry you might be overdoing it, but you
see a smile across her face as she turns to lay on her back.
"Come," she requests of you, bringing you on top of her body. "I'm told that a
woman's breasts are quite comfortable to rest one's head on. Why don't you try
it?"
"Okay," you nod and carefully rest your head in the middle of her chest. It's
soft, indeed, and your body instinctively cuddles her, wrapping your arms
around her chest, your legs nestled between her thighs.
In the meantime, she wraps her arms around you, bringing you closer. She runs
her fingers through the back of your head, bristling your hair, before
traveling down your neck and massaging the base. You feel yourself relaxing
already as her other hand rubs up and down your back, tracking her finger along
your spine, and softly running her palm along your bare bottom. Her breasts
serve as a good pillow, and you've never felt more comfortable.
"Princess..." you softly coo out.
"All is well, my dear..." you hear from her. She grips your shoulder tightly as
she brings you closer to her. Despite the both of you being naked, you feel
incredibly warm, mostly in your cheeks. Being held like this reminds you of the
way you've seen the couples in town, along with your own parents, hold each
other. With that in mind...
"Princess Luna?" you ask to catch her attention.
"What is it, my child?"
"Could...could I...kiss you?" you barely manage to get out. The princess looks
caught off guard for a brief moment, as though she was not expecting such a
request. Her face quickly changes back to her serene smile.
"Certainly," she answers, a slight lilt in her voice, trying not to laugh. She
brings you up to her eye level and holds the back of your head. She brings her
lips to yours, moving them so they fit in the best manner possible.
You close your eyes once more to better take in all the sensations that were
going on at once. Her lips closing and opening ever so slightly. Her hand
deftly holding your head. Her other arm reaching down your back while she grips
your butt hard enough for you to notice, but not enough for it to hurt. What
you would give for this to last forever.
Finally, Luna stops kissing you, drawing her head back and giving you that same
reassuring smile. You can't help but do the same, grateful that she's doing
this for you. Her grasp on your body hasn't lessened, but you don't mind it at
all.
"Thank you, Princess Luna," you say with all the gratitude you can muster. You
both turn to the side, and she loosens her hold on you.
"'Twas not a problem, Pipsqueak. Although," she smirks, glancing down at your
waist, "it seems there is now another matter."
"Hmm?" You look down, following her line of sight, and see that your penis has
grown bigger and stiffer! "Ahh! Why's it like that?"
"Do not fret. This is completely natural," she tells you ever so calmly. "It
means that your body is enjoying what you're doing."
"It's not gonna stay that way forever, is it?" you ask. "I don't think I could
hide this with my trousers..."
"No, it will not," Luna answers with a slight giggle. "In fact, why don't I
help you bring it down to normal?"
"I-I'd like that..."
"Then lay back," she advises you before gently lowering you onto your back. She
then reaches for your erect penis and begins to gently run her fingers along
the shaft.
"Mmnh!" You twitch at the sensation. You don't remember your penis being so
sensitive to touch. Your breaths become short and your body squirms as she
continues to rub and squeeze. You close your eyes to fixate on the feeling.
"How is this, Pipsqueak?"
"It's good! It's really good!" you cry out.
"Then, you are sure to enjoy this!" She positions herself over your body, your
legs straightened between hers, and aligns her waist with your own. She motions
her fingers upward, and you feel your penis moving straight up in kind. Keeping
it steady, she lowers her waist down, and you watch as your boyhood is
swallowed up by her body. It feels warm and extremely moist, but this is the
best feeling you've had all night.
"Mmm! That feels so nice, your highness!" you exclaim.
"I have barely started," she responds. Luna begins to move her hips up and
down, causing that sliding sensation you enjoyed to occur over and over. You
bite your lip and grip the sheets, only letting out little gasps as she
continues. Each thrust inside is like electricity shooting through your body,
sending waves of pleasure. In the meantime, Luna's motions intensify, causing
her breasts to bounce in a most pleasing fashion.
"AAAHH!"
Finally, your body gives out, as you feel all that pleasure and sensation leave
your body through your penis, shooting straight into Princess Luna. At this,
she stops her motions and holds herself tightly, letting the warmth inside her
keep her satisfied. You feel your body go limp, as though you had run a very
long distance, when you hadn't run at all.
"Thank you, Pipsqueak," she coos as she slips out of you and lays back at your
side. "That was most pleasing."
"You're welcome, your highness," you say before you let out a great yawn. "That
really tired me out. I think I'm ready to go to sleep now..."
"Splendid," Luna waves her hand, moving the sheets to cover the both of you.
She brings you close to her and kisses your forehead. "Sleep well, my child. I
will make sure you have no nightmares."
"Thank you...Princess," you say, closing your eyes and nudging yourself
comfortably with her. "Good night..."
"Good night," she tells you. As you drift off to sleep, you hear one more thing
before you lose consciousness.
"I'm sorry, but I must ask that you forget this..."
===============================================================================
"Pip! Pipsqueak, wake up! Breakfast is ready!"
You groggily open your eyes at the sound of your mother, Derpy's voice. The
nightstand with your clock is the first thing you see. You feel well-rested,
but you can't seem to remember when exactly you went to sleep. It doesn't
matter either way, you suppose. You lift yourself off the bed and sit up,
stretching your arms and letting out a great yawn, before climbing off the bed.
Walking into the kitchen, you rub your eyes and treat yourself to the sight of
breakfast. Dinky, wearing one of your father's shirts, looks over at you as you
come in and stops eating her blueberry pancakes only to furrow her brow and
tilt her head. Derpy sets a plate for you, but dons a similar expression when
she sees you, raising an eyebrow in confusion. Your father, Time Turner, puts
down his morning coffee and chuckles.
"Well, good morning, you little jaybird!" he says. "What brought this on?"
"What?"
"Why are you naked, Pip?" Dinky asks you.
You quickly look down and see that you don't have any clothes on. Blushing
madly, you turn around. "Uh...I dunno. I..."
"Oh, you probably just took them off in your sleep," Derpy tries to explain.
"Happens to me and your father all the time."
"I know, but...I don't usually do this," you say, trying to rationalize the
situation. "I'll go get dressed right away!"
"It's fine, Pip!" your mother says. "Just sit down and eat before your food
gets cold!"
"Okay," you say and sit down. As Derpy pours you some milk, you see Dinky
fussing with her shirt until she lifts it off her head and throws it on the
floor. Surprised, you ask, "What are you doing, Dinky?"
"If you can be naked at the breakfast table, then so can I!" she boasts.
"Right, Papa?"
"Just so long as you get dressed after breakfast," your father answers. "This
isn't a house of nudists!"
You proceed to eat breakfast like normal, or as normal as you can be with your
bare butt on the chair. The conversation turns to what everyone dreamed about
the previous night, a standard morning topic for this family. Dinky dreamt
about meeting Princess Celestia and being taught magic by her.
"How about you, Pip?" Derpy asks. "You probably had a good dream if you slept
in like that."
"I think I did," you say, "but I can't remember it..."
"How do you know you had a dream, then?" Dinky asks.
"Well, I can't remember it exactly," you clarify. "I just remember...feeling
really good."
"Maybe it was about a crush?" Time Turner teases.
"Father!"
Once breakfast is finished, you and Dinky head off to your respective rooms,
Dinky picking up her shirt beforehand. You search for where you might have left
your pajamas, and find them near the window. Strange, as the window is way too
far from your bed for you to have thrown your clothes. You shake it from your
mind and pick them up, when another question presents itself.
Where did your underwear go?
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