Anonfilly's Usual Shenanigans

by UndeadAsylum

Chapter 1: Long, Lonely Nights

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You awake from a fitful sleep as you often have for this past few months: dry-mouthed, suffering from aching eyes and a malnourished body. It's not the fault of your temporary nanny - she knows you used to be an adult and lets you choose how to live your life, even if it's unhealthy. Nay, it's all on you. You chose to skip dinner, to neglect drinking water to the point you often only piss once or twice a day, to keep out of the affairs of Ponyville's fillies and colts and stay indoors, to read pony comic books and light novels instead of fostering any potential talents or seeking your super duper tramp stamp talent. You only have yourself to blame for your piss poor diet and habits - this fact has led to many a night silently wallowing in self pity.

And now it's culminated to your current state: tired, lonely, restless, hungry, thirsty, and most embarrassingly, a little pent up.

You slowly drag your pudgy little filly body out of bed, lazily lumbering your way through the crystal castle's corridors. The halls to a stranger may be too perplexing to navigate, but in your time staying with the princess of sparkles and sodomy, you've memorized routes to and from your room to places of interest. A couple easy left turns later, you're outside the caregiver's master bedroom. You slowly open the door, careful so as to not rouse the softly breathing mare from her sleep too annoyingly. A lump juts from your throat, but in swallowing you push it back down. This is going to be a really awkward request.

"H…hey Twilight?" Using her name in a soft murmur coaxes a confused countenance to wash over her face, the formality almost unheard of in all the time she's known you. You've been a brat, admittedly.

"Mmmn….'non?" She slurs out, eyes crusted with the sandman's namesake as they weakly pry open. Those big curious eyes meet yours - a visage you still can't get used to. Such emotion is so easily conveyed in the eyes for ponies… "Need somethin'?" Her tone, even when sleep addled, seems concerned after hearing her name uttered instead of one of your crude nicknames. That's probably a first.

"Yeah, I….I can't really sleep." As Twilight sits up her expression goes from sleepy curiosity to mirth. "Before you-" you start again, feeling indignation well up in your chest. "…before you laugh, I didn't have any nightmares or get scared of anything. I just…I want to let you take the wheel."

"Let you….take the wheel? Anon, what's wrong?" Despite her worry, your own mind is racing with a different set of emotions. Inferiority, self loathing, embarrassment - even a little fear.

"You were right, okay?" Despite trying to keep your voice level, you feel your youthful vocal chords warble in your moment of emotional instability. "I'm just a stupid filly, even with experience as a man. I…can you just, do what mares do best? Please? I need the company tonight."

Now she's definitely awake. Her covers slide off, and you feel weightless as you're gingerly placed beside her in bed. A wing unfurls, resting atop you as she delicately hushes you. Even her shushing just oozes with affection and care. Your dense but light filly body feels overly sensitive, her warmth sending tingles up your spine that you feel ashamed for having felt.

"Anon…it's okay. Like it or not, I adopted you to make sure you would live a good foalhood, even if it's an unorthodox one. Anything you want, I'm right here." You can't muster up the courage to continue speaking. Your legs feel weak, crumpling up and folding in toward your torso. Your throat suddenly feels too dry and empty to let out even a mutter. You open your mouth, eyes starting to get damp with excess moisture as you try and fail to speak. Thankfully, your filly tummy growls, saving you the embarrassment of having to say out loud what you want.

"Oh Anon…" Just hearing the worried tone she uses to say your name makes your chest hurt, and you finally let out a little whimper of suppressed guilt as the waterworks start up. "I should have pressed you on dinner, huh…do you want me to make you something? I can do that."

You gulp down the lump in your throat before sniffling gently, shaking your head. "Well, I don't want you going back to sleep hungry. But, um…can I…make a quick confession?"

"A c…a confession? What do you mean?" Your light hiccup is met with a purple wing softly wiping your snout of dribble and your eyes of tears. You lean in, trying with mild success to calm your breathing back down.

"Ever since you first arrived here, I've…been milking myself. In case you ever…wanted to, give breastfeeding a try. I, erm…I was sort of hoping I could be able to do that for you."

Some may see this as creepy, or at least a little queer, but you only find your eyes gravitated to hers, her blush rising alongside yours. "You've been…milking yourself? For me? But…I've been so hostile toward you…"

"I always had an inkling that you would come around, sweetie."

Your hooves tightly wrap around her, and you put your head over a shoulder, embracing the mother figure. "Fuck, Purplesmart…never thought we'd end up sharing a fetish like that."

Her chuckle as she gently returns the embrace is laced with her meek arousal. "Well…if it's your fetish…and you're legitimately hungry…guess that's a win-win, right?"

You feel your own little teats hardening as you return to resting against Twilight's chest. "You're such a pervert, soliciting a filly like me in my moment of insecurity…" She retreats slightly, looking indignant as she prepares to rebut that teasing accusation. Before she can however, you close the distance, giving her a gentle peck on the nose. "Maybe instead of dinner we can do this each night?"

Her lewd shiver is all the verbal response she can offer before you maneuver under the covers.

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Anonfilly's Usual Shenanigans

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