Insomnia (Anon x Luna, NSFW)

>Be awake at the stroke of midnight
>The moonlight bears down on Canterlot Castle, granting the balcony outside your room proper lighting for book-reading
>Shame it doesn't help you sleep
>You pace and pace and pace in your boxers as you try to work out all of this energy you seem to have built up
>Fuckin' insomnia bullshit
>Every night for the past week it's been like this
>Get into bed, close eyes, open them thinking it's morning
>NOPE
>It's been 10 minutes
>Hell, 3 days ago you begged Luna to magic you to sleep
>She's been doing it since, but tonight she wanted you to try and sleep on your own, just in case you might suffer from some "adverse effects of magic-induced unconciousness."
>You don't give a rat's ass if you never wake up, you just want to get some fucking sleep!
>You've been standing out here trying to think of a way to get to sleep
>And at this point, you're pretty sure all this thinking is doing more harm than good
>Fuck it, you're not gonna do yourself any good standing out here letting your mind race
>Best to go back to bed and try again
>As you open the doors out of the balcony, you get an idea
>You should go to Luna's room
>You're not sure if she'll be willing to help you (or if she's even awake) but it's better than wasting your time trying something you know won't work

>As you walk up to her bedroom door, you hold out your hand to knock
>However, when you go to knock, the door creaks open to your touch
>Guess she forgot to lock it
>As her door swings open, her sleeping form shows itself, lying on her side above her strewn-about covers and mane disheveled
>You hesitantly step forth and tap on her shoulder, hoping she'll awaken and put an end to this waking nightmare
>No dice
>Well shit, looks like you'll be suffering alone
>You sigh and flop down on to her bed defeated
>When you land, you find the princess's flanks facing you, her tail covering her most private bits
>You sit there, simply boring a hole into her butt with your eyes before a thought arises
>You might as well take a look at the goods
>It's not as if the ponies here wear clothes, so you're not new to the whole puss-peekin' deal
>And besides, she's asleep
>You'll just move it back into place, like it never even happened
>You lift her tail away, moving yourself lower to get a good look
>Into your view pops her leaking labial flaps and her anus, tight as can be
>You get a good look before Lil' Nonny pops out of his hideyhole
>The rational part of you is reprimanding such disgusting violations of privacy and demanding you leave her royal presence post-haste
>Lil' Nonny says you should touch it
>Well, you heard the man, touch it!
>You slowly bring your fingers up towards her no-no square before finally tracing one around her labia
>As your hand-sausage finishes a lap of the lips, her clitoris winks into existence, pulsing and begging for stimulation before leaving disappointed
>With that, you decide to see how she looks on the inside
>Bringing one of your hands to rest upon her flank, you bring down your thumb and utilize its kungfu grip to open her up
>Her inner folds are sopping wet, pulsing and quivering in hunger
>That might just be your sleep-deprived mind talking, but fuck it, you're in this deep as it is
>With bated breath your thumb slowly withdraws itself, and your middle finger slides into her waiting crevice
>As it does, you can feel Luna's folds attempting to pull it in
>The pink button at her pussy's edge reappears
>However, before it can abscond, you brush it, leading Luna's whole body to shudder
>Sensitive little creature, are you?
>You begin to move your middle finger back and forth with a steady rhythm, making sure to not go too fast so as to not wake her royal highness
>Her breaths become a bit haggard, and you brush her clit whenever it has the audacity to show itself
>After a few minutes of fingering her slit, you slip your finger out and decide to slip it into uncharted territory
>Her ass
>The backdoor had been puckering in desperation after that beating at her front
>You tease it a little, tracing her anus with one thumb before utilizing your up-to-now-unused hand and stretching her wide open
>Much like her other hole, the walls of her rectum pulse and quiver
>Finger, meet mouth
>Giving your big man some much needed lubrication (and tasting Luna's succulent nectar), your finger is given the green light and pries its way into the moon princess's anal cavity
>You swear you hear a sharp breath as it reaches the knuckle
>Like before with the cooch, your finger makes precise, practised movements, pumping her anus at a slow and constant tempo
>It's even tougher back here, with her ass muscles doing everything in their power to reel your finger back in
>A couple more pumps, and you look down at her vagina for a status report
>Her juices are flowing out quickly, and her clit' popping in and out like it's unsure where it wants to be
>And then you had another idea
>Another no-good vile lecherous genius idea
>Keeping your finger inside her butt, you ready your mouth in anticipation for what's about to come
>The pink button pops out again and you rush into action, covering it with your mouth and suckling at it with all your might, while at the same time pumping her anus to a faster beat
>"Hahhh..."
>You nearly jump as she audibly moans, but you know you're not done
>You keep at it, speeding up a bit as she moans again
>"Aaaahh..."
>Allllllllmooooooost
>Therrrrree-
>"AH!"
>A cute high-pitched squeak erupts from her throat as her anus nearly crushes your finger in orgasmic bliss
>The crushing is followed up by a warm liquid flowing out of her cunt
>You open her folds with your unused hand, and the leak turns into a river of cum
>That squeak from before seems to continue in start-and-stop fashion whilst the hot fluids erupting from her cervix coat your face and stain her bedding
>After a bit, the squeaks stop, as does the stream
>On that cue, your mouth leaves her clit, and your finger slides out her bottom
>With a lick of your lips and hers and a gulp, you turn your attention to your little soldier, standing at attention himself
>Well shit, now you've gone and gotten yourself all aroused at engaging in foreplay with a sleeping mare
>You could probably leave now though
>You've had your fun
>And Luna's fun, for that matter
>All you'd have to do now is put her tail back, slip out quietly, and BAM! You're in the clear
>But Lil' Nonny looks so sad
>He's all raring to go, but you're gonna leave?
>...
>...
>No
>You started this
>You're gonna finish it
>Determined to get the job done, you slink on up into big spoon position and position your cock right at her entrance
>You tease it a little, making sure she's all good to go, before sliding in
>Her folds seems to notice, clenching at the sensation of penetration
>You're not letting her settle, however
>You bring your hips back, pulling out just before the tip, before slamming in hard
>In for a penny, out for a pounding, am I right?
>You find a nice consistent tempo, and wrap your arms around the princess's neck, digging one of them under her
>God, she feels so nice
>A moan forms in the back of your throat, and you attempt to staunch it by muffling it with her mane
>You can't help yourself
>Her pussy makes you feel so comfy, even with your sleep problems
>You wanna stay here forever, in this moment
>It's getting harder and harder to hold back
>Luna's starting to moan again
>"Aaaaanhhh..."
>Anoooohhh..."
>You can almost hear her moaning your name
>You can't hold back!
>This is it!
>With a hard buck, you slam yourself balls deep into her, releasing all your built-up gunk
>And like a switch, you feel an exhaustion you thought you'd never feel
>With one last breath, you utter a phrase known only to be spoken by the most daring of devils
"Worth it...."
>You finally embrace slumber, not even bothering to pull out

>Your dreams are wetter than you thought possible
>It's like some omnipresent hedonistic hoopla, and everyone was invited
>But the most important character there was Luna
>As if wanting to continue your unexpected fraternizing the night before, she simply waved her tail in a come-hither fashion, and you went about with your carnal galavanting
>However, this sexual expedition went somewhere a little different
>From that place where babies come from to where the sun dare not shine
>However, as you finish up in a heated climax, you jump up, now awake and concious
>Inspecting your surroundings, you are surprised to find not a dank dungeon deep within Tartarus, but Princess Luna's bed, now shimmering with daylight streaming in from her windows
>And surprisingly, Anon Jr's out of his hole and... fast asleep?
>And your boxers are wet?
>You trace your finger along the large wet spot and sniff
>That's not piss
>Or cum
>Not yours, anyhow
>You rise from Moonhorse's bedding and proceed to one of the somewhat-open doors on the other side of the room
>You gently slide your head into the crack to find a bathroom, currently occupied a key on the counter and by Luna herself, brushing her teeth
>As her tail sways back and forth, you note something odd coming from her back end
>A mysterious white liqu-
"OH!"
>Great read Velma
>Luna turns her head towards your soon-to-be corpse, her expression unreadable
>Welp, goodbye cruel Equestria
>Before you can make a mad dash to the window however, Luna's magic stops you
>"Anon."
>She turns you around and puts you down
"W-"
>A wing from her majesty to your mouth stops you before lowering itself
>"Before you ask, the door to our bed chambers was unlocked because we had forgotten to lock it out of exhaustion. Court was hell yesterday and we were simply waiting to escape to somewhere away from that mess."
"Bu-"
>Her wing comes up again, and you stop yourself
>"As for your actions this previous night..."
>The key from before seems to float in front your face
>"If you are ever in need of nightly companionship, or simply release.."
>That key now floats into your hand, her magic closing it
>"Within our bed chambers, thou shalt find thine sleeping beauty."
>...what?
>"And we-"
>A blush to outshine the sun forms on her cheeks
>"-I was hoping, maybe, you might extend me the same offer."
>Hold the fuck up
>"You need not answer now, but if you do, bring me the keys to your bedroom. I'll know what to do."
>She gives a wink before turning back to the mirror and continuing her brushing