Long, Lonely Nights

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.

We All Knew It Would Come to This

After a surprisingly satisfying and only slightly kinky cuddling and breastfeeding session, you drift off into a comfortably dreamless sleep. Your heartbeat is almost perfectly in sync with Twilight's throughout the night, the warmth of her body around yours making you feel safe, secure, and loved. Nothing could spoil such a lewd yet loving night with your surrogate pony mother.

At least…that's what you think. But after drinking so much before bed, your bladder quickly fills to its capacity, your unconscious body simply letting go of the light pressure inside. It's not until you hear the shifting of Twilight's body, and the sudden spike in her heart rate, that you awake; unfortunately as soon as you feel the soaked sheets beneath you, you immediately know what happened.

You look up at Twilight from your position resting on your side facing her. Your eyes well up with shame, and you feel your body violently shudder - whether mainly out of disgust at what's matting your fur, or out of a sudden and overwhelming urge to jump out of bed and find somewhere to die, you may never know. Her expression is not judgmental or angry, but concerned…it only compounds the guilt weighing down on your chest more, so you avert your eyes.

"I…I didn't mean to…I didn't even f-feel it com…" you stutter quietly, voice wavering as it slowly gets stuck further into your throat. Before you can finish, however, she places a hoof on your nose, shushing you as her familiar purple-pink magical aura surrounds you. You curl into a ball, sniffling as Twklight gets up from her slumber.

"Anon, you've already drank half a liter of milk from my tap. I understand that a filly's body isn't so easy to keep composed while sleeping."

"I know but…"

"But nothing. Who cares about you more than anypony in the whole wide world?"

"Y-you…"

"That's right. I understand transitioning is hard, especially into a filly with no muscle memory or mature brain. In fact, I'm happy to make accommodations to help you stay comfortable." Your eyes are full of trepidation, curiosity yet fear.

"Really? B-but, what will you do? Different bedding? Some kind of magic?"

"I can buy you a pack of Huggies until you feel you've fully regained your continence." Such a statement would have floored you, were you not hovering three feet high in a castle made of crystals in the body of a little filly.

"You - you're going to…to diaper me? Y-you said….you said I was only a couple years from fully growing up…" Your dejected whimper is paired with a desire to break eye contact and seek something to occupy your mind - and you see beneath you a tub that Twilight runs for your bath.

"Anon, sweetheart, there's nothing wrong with not having gained full control of a new body after a few months. Most foals don't graduate from pampers for a few years, and nopony pays them any mind." You feel lightheaded and even a little nauseous, only snapping out of your emotional state as you're gently placed in a tub of shampoo bubble bath solution.

"I…I'm a grown ass man. Twilight, I can't just…" She places a hoof on your head, just as she gently places a hooffull of shampoo in your mane.

"Anon, listen to me. There is nothing wrong with needing diapers. You have no prior experience with filly bits, and your body is physically young and not yet matured." You sniffle, eyes misty yet unblinking as you stare into into her own eyes. "I don't want to see you cry, okay? Who loves you more than anypony in the world? C'mon, say it."

"Y…you do, purplesmart…" The mare leans in, kissing you on the nose before dropping a mass of suds on your head, smiling delicately.

"That's right. And if you ever feel like you need somepony there for you, who do you call for?"

"You…" Your voice is feeble, like that of a trapped animal who finally gave up on fighting its predator. The aching of your heart lessens; your chest swelling with adoration for the dedicated caretaker's humility and kindness.

"I can't hear you, Nonny~"

"S-shut up, dildo, this is just rhetorical garbage anyway," you huff, crossing your front legs at your chest indignantly. But despite it, you smile just a little…

"Just say it, for me?" She flushes brightly, resting her chin on the rim of the tub as you relax in the steaming bath. You can't fight it for long; your face contorts, cheeks puffing out as you look away to try to conceal a girlish giggle; your own face turns an even brighter shade of red; and finally, you let out a long, tittering giggle, covering both your eyes with your hooves.

"F-fine, Twilight, it's you! You corny little nerd." Despite her indignance at being called a nerd, she soon follows suit, laughing as gently and level-headed as she can.

As she drains the bath, she wraps you in a towel like a dog, lifting your towel-burrito body up and carrying you into your bedroom. "I'm going to the store for you then. It's about sunup, so I'll be back in about half an hour with the parcel and some flour for pancakes. Can you be good while I head out?"

You would normally get to scheming, or simply hide away to do your own thing, you feel your heart race at the mere mention of sugary hotcakes. You have the best mom in Equestria.

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You dry off and brush yourself just in time to hear the castle open and your momfu come inside with bags of supplies and groceries. You set down your brush and trot out to the hall before the nerd finishes unpacking, and she smiles with a sincere glint in her eye as she tears open a bag and unfurls her gift: a plain white diaper, with two tapes on both sides to secure your hips and nice frilly cuffs to prevent leakage. A hole is also in rthe rear, to threat your tail through while also being as well sealed. The inside has a thick strip of some kind of synthetic fabric from rear to front, but on the outside are no obnoxious decorations or labels. Generally speaking, it looks like a fine fit for you…for a diaper. While you are glad she's got the piddle insurance, it still humiliates you that you have to wear it to begin with.

"Does this look good to you Anon? I thought I should get a high absorption brand. Most foals' brands come with decorations but I know it's embarrassing enough to be put in diapers as is, so I shelled out the bits for small adult ones. Do you have any qualms with wearing for the day today? Not that I expect further accidents but it may benefit you to…get used to wearing it." Now that she mentions it, this whole thing feels strangely intimate for a simple garment for the young and elderly…

"I…I guess that checks out. Mind if we stay in the castle today, no outings?" She pats your rump lightly, smiling.

"Of course. If you want jammies or other clothes to accompany it, I can order you a commission or two from Rarity. And I won't make you pad up except at night."

Minutes later, she powders your rump and seals the thing shut, leaving you on your back with legs in the air. Your privates feel strangely soft from the drying powder, the underwear only adding to that softness. While Twilight makes pancakes, you simply…sit there, on your back, white ball of plush and lightly crinkling plastic keeping your legs just a little further apart than normal. Your rump and fillyhood rub against the dry fabric, a hoof resting at your crotch as you feel almost overwhelmed. Where do you start? Do you even want to think about this thing any further? This big stuffy pamper, the strange widening of your legs by its thickness? As you slowly shift up onto your flanks, you hear crinkling and a gentle little 'pomf' of talcum powder escapes the waist of the diaper. Your heart races. Your eyes mist up. Your breathing seems to peeter out, only audible in gentle whispering inhales followed by ten seconds of holding it in.

"-colate chips or blueberries?" Your head jerks up, one hoof pressed into your crotch and your breathing erratic. You try to speak but nothing comes out. But…you have to say words! Say them!

"I…I don't know, whatever's easier for you!" Why did you shout that? Stop! Deep breaths! Those aren't deep! BREATHE! BREA-

"Oh Anon…all this is your fetish, isn't it? Is that the issue?" You shake your head, trying to speak again and only succeeding after an awfward silence.

"I…no! I mean…I don't- I feel like…I think I'm going to pass out, I've never felt so…" Suddenly your voice squeaks and you lose your ability to finish the statement.

"Anon? I think you need to try and relax. You know I wouldn't tell a soul anything that you're worried about letting out. Right? I'm here, and I am more than happy to lend my ear."

"I…I can't explain it. I'm dry as a desert down there…but I can't breathe…my heart feels like a drum…is this arousal? But I feel…small….like I'd be easy to make someone's plaything. I don't...is it bad? Am I horny? Am I afraid? Am I just nervous?" Twiggle's hoof on your head stops your ramble short.

"Anon. Everything is okay. It's just a diaper." This reassurance helps calm you, but then you feel more self conscious. How patronizing…no, don't cry, not now..

"Anon…nooo, noooo, don't feel pressured…I'll be here as long as you need. Give mama a hug?"

You suddenly jump up to hug her tight, lightly sobbing. Your emotions continue to get the best of you, and you merely stay there as the room falls silent. Just the two of you fill the room with its ambient sounds: your crying calms as twiggle whispers sweet nothings to you, hugging you back with resolute tightness.

"T-Twilight…?"

"Yeah?"

"Am I…beyond helping? Or am I just doomed to be a b-bedwetting retard forever?"

"Anon…of course not. Anypony can be made better. You may be a unique case, but you can still get better with your body. You can't be expected to be experienced without time though. Just let mistakes happen, and learn from them."

Your conversation melts away. It grows harder to remember it line by line, your humiliation and conflicting emotions distracting you. However, soon enough, you simply accept the embrace. Just like the night before, she envelops you in warmth, slowly silencing all your whimpering until you're simply resting against her.

Of course, Murphy's Law is in full effect, as you hear a gentle hiss followed by a surprisingly cozy warmth between your thighs. Instead of feeling compelled to shrivel up and cry, you simply relax, a small smile remaining on your face.

"You know…it's not so bad wearing this. Long as I don't have to walk in public like this…I could be wearing worse. Right?"

Well, I'm glad you feel that way." A peck is gingerly placed on your forehead, and despite attempting not to, you succumb to the instinct to giggle like the filly you are.

Parties

After two weeks of genuine improvement to your demeanor, you feel somewhat refreshed. While your...sleepwear still embarrasses you, it also provides some security at night - and hey, you've only used your protective garment twice! That's something to be proud of, right...? Now that you've revealed your power level around Twilight, she's actually acted as a surprisingly good bro; while of course you do butt heads occasionally, she seems much more comfortable fulfilling the role of your surrogate mother than you would have ever expected from the mare you've called 'top cunt' for months now. And when she's not mothering you, she offers snacks and books to pass the time. She doesn't offer any lewd works, but she doesn't outright prevent you from nabbing a book or two, or buying stuff with your allowance.

In the meantime, you've decided to try the tabula rasa approach to life in Ponyville. Yesterday Twilight offered to be Pinkie's ghostwriter to plan a belated birthday party after your initially failed "Welcome to Ponyville" party that ended in spaghetti flying in every which direction - literally! _{Yeah, you don't know how you're gonna apologize to that Twist girl after that.} But regardless of the past, this is a chance to turn over a new leaf, and actually get to know the ponies in town better.

Not one day after Twilight's party planning offer, you come home from a little walk through town, apple in hoof and a few handheld games hidden in your saddle pouch, to see that the library's almost completely dimmed out. The curtains are all drawn, the candles and lamps all snuffed out and the foyer of the library utterly silent. Normally this place wouldn't be closed before sunset, and Twilight would spend an hour or two longer checking inventory. Before you can even ask the doubtlessly full room what's up, a series of small poppers and flares light up, and all the curtains are drawn back so you can see the surroundings better: somehow Pinkie's managed to get a party of forty ponies, most being young adults and older fillies, to attend this impromptu celebration. Twilight, Pinkie and Applejack act as chaperones for the party, while the younger ones shout out the typical "happy birthday" cheer.

The library isn't that different from its normal look other than the initial boom of activity; bookshelves and tables were moved to allow room for a proper gathering, and the general decor is more subdued and relaxed, more like a super bowl or movie marathon party than a kid's-show equivalent to a birthday party. The cone-shaped party hats are done away with, in favor of a few ponies dressing up in what seem to be convention style casualwear. You never were a fan of conventions, but you can't diss someone for wearing their hearts on their sleeve like this. It takes guts.

Pinkie Pie and a few other ponies set up to play a wide assortment of songs ranging from cabaret to folk to swing jazz to some kind of satirical country style. While you're not by any means a musician, you are inclined toward all kinds of genres of music.

After nearly half an hour of indulging in pizza and cupcakes while chatting, you find that you're not so uncomfortable in this environment. Granted, a smaller party is preferred, but when you're not being choked by over-positive music and cliches, partying isn't so bad. A few fillies offer their address for sleepovers and give ideas for places to visit when you're free - you didn't have the heart to admit you're always somewhat free thanks to skipping out on school. Of course, as the time passes, your relaxation loosens your lips, and with that a few ponies grow uncomfortable with your sense of humor, but only five to ten ponies abandon the party.

Finally, Pinkie calls you up to the little makeshift stage to speak to the rest of the party. "Alright Anon, I think it's about time you get the spotlight tonight. You got anything to say to everypony here tonight?" Your heart races as you try to think of something to say. Your legs work on autopilot as you force a little smile onto your face, and as you reach that stage, you still don't quite know what to say.

"Ah, well...thanks for comin', would be point number one. After that little incident a couple months back, I didn't think anyone'd pay me a visit." You flash a shy grin, chuckling a bit to yourself as you look at the crowd to gauge their reaction. They seem generally happy for you, a few even giving a little chuckle. "Ah, otherwise...I mean, there's not that much to say. I survived another year of life. Can't say I'm too special there, especially with how young I am. Really I'm just glad there's other ponies that aren't afraid to get a little risque with their humor - by the way Pinkie, I...honestly never thought you had it in you to sing cabaret."

"I sing lotsa stuff, Nonny! Whatever makes my friends happy." The resulting d'awwwww from the other ponies puts a red tint on your face. These sentimental little twerps...

"Well, thanks for that then, Ponka. Now...I-I-I'm not too good on speeches, so I think I'll leave it at that if that's alright. Just a big mushy-gushy thanks to all you little bastards for sitting through my rambles."

After you give Pinkie her stage spot back, she rears up on her hind legs, hugging you tightly around the shoulders. Before you can react, she whispers something into your ear, smirking lowly. "Now, I got a little something for you, and you can sing along if you want. Twilight managed to put a few songs from your phone to sheet music, so I've got a special one for ya."

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"And tonight,
We're riding our black unicorns
Down the side
of an erupting volcano!
As we drink, drink, drink
From a chalice filled
With the laughter of small children!"

After finishing up your own little performance, you grin at nobody in particular. "Best timeline."