Nightmare's Pipsqueak

by LegionofPony

Rating: mature
Tags: Sex, Pipsqueak, Slice of Life, Death, Alternate Universe, Nightmare Moon, Porn, My Little Pony: Friendship is Magic, Fetish
Length: 9154

Nightmare Moon and Pipsqueak have been together since she took him away from his parents and raised him as her own. Now, as he's reached puberty, Nightmare Moon thinks it's time he learns what's happening to his body. Using very hooves-on methods

TAG NOTE: the 'sad' and 'death' tags are ONLY FOR THE BEGINNING. THIS IS OVERALL NOT A SAD, NOR GRAPHICALLY VIOLENT, STORY, AND NO DEATHS ARE ACTUALLY DEPICTED, ONLY MENTIONED.

In an alternate universe, Nightmare Moon has been the sole ruler of Equestia for many years now, having defeated her sister and banished her to the moon, and captured the Elements of Harmony before their wielders could use them against her.

Now, after having taken all Ponyville's young to teach them to properly serve her after her victory, she takes a particular Earth-pony colt to be her personal assistant and confidant at a young age. She can't help but notice how he's grown in the years since...as well as how much he's been looking at her backside as he's walked behind her as of late.

One day Nightmare decided it was time for her, his surrogate caretaker, to give him 'the talk' - and an unexpected hooves-on demonstration.

~

Contains: Monarch/Queen Nightmare Moon x Pipsqueak, brief, once-off instance of foal abuse (smacking across the head), anatomically correct (including teats and penile flaring), scents/pheromones, full-package herm (mare with all stallion parts) on pubescent colt foalcon sex, size and age difference, sex education, physical exploration of a pubescent colt on a herm, including a partial hoofjob (both on male and female parts), mild femdom, face-sitting, magic stimulation, male loss of virginity (penile and anal), brief vaginal sex, anal sex (male on herm, herm penetrated), autofellatio (self-blowjob) while having sex, male anal penetration, prostate stimulation (male and herm), internal cumshot (self-mouth and anal), oral cum swapping, and mild cum inflation. All acts are consensual.

~

Credits:

Written and edited by me, LegionofPony

Coverart is by 'doctorraz', and can be found on derpibooru at the source (SFW).

Commissioned by Lanxide. Thanks so much for your commission!

Published 2018-04-25 05:10:06 UTC
Last updated 2018-04-25 05:10:06 UTC

Nightmare's Pipsqueak

Several tall candelabra with five candles each were throughout Queen Nightmare Moon's personal chamber's, as well as a large brazier with a minor light spell enchantment also hanging over the bed, all adding a soft, comfortable glow like moonlight to the room. Pipsqueak was sitting on the bed, playing on a Joyboy™ hoofheld game console that she’d gifted him on the previous Hearth’s Warming Eve. As he heard the door open, however, he paused the game and looked up at her expectantly, ears pricked in attention.

Nightmare kept things subtle at first, her tail swishing rapidly as she walked over to the bed, spreading her scent around as her hips gently swayed a bit more than usual. Nightmare Moon then faced away from the colt on the bed, who she had the full attention of now it seemed, and began to strip off her armor, sliding out of her shoes, then removing her crown and other regalia slowly in front of the colt. Her hips were moving more than strictly necessary meanwhile, letting her hair and tail flow naturally now. Her tail flagged high as she slid her chestplate off, leaving nothing to the imagination of the older colt on the bed, who was now feeling much warmer all over as his eyes were naturally drawn to the dark-grey-lipped marehood and anus revealed in full to him, the prior lightly glistening in the dim candlelight, as well as a not-so-little something extra only Alicorns and the rare other mare had.

After teasing Pip some with a further shake of the hips, Nightmare then moved over to her bathroom, making sure to leave the door open as she removed her makeup as well. As she knew Pip could see directly into the bathroom from the bed, she kept her tail still flagged high all the while, taking small glances to the colt on the bed through the mirror and seeing him fidgeting in place, making her grin at seeing her teasing was having an effect.

“I feel very tense after today Pip, my wings especially. May I trouble you for a massage?” Nightmare asked as she walked out and faced Pip, seeing the colt putting the game console down and nodding to her, a mild blush tinting his white cheeks. She wasn’t lying, as she was indeed fairly tense. Besides, a massage always felt nice before the main act.

“A'course, my Queen.” Pip replied loyally in his Trottingham accent, Nightmare positioning herself so she was laying on her stomach on the bed, her forehooves folded under her chest and her chin resting on a pillow she’d summoned with her magic. Pip meanwhile, as always, positioned himself so his chest and crotch were pressed to her back as he laid on her, letting him reach her upper back and wings easily, just like she'd taught him to. The simple routine of serving his Queen once more.

It started off normally enough for Pip, him giving her a gentle, cursory rubbing over her whole back to seek tense points, then moving on to rub the base of her wings for the same reason. After sensing the tension in that area between her wings, Pip focused pressure there, hearing a gentle series of pops and also getting a relieved grunt from Nightmare, followed by a quiet moan and squirm as he started rubbing.

Nightmare's wings were partially erect moments later as Pip rubbed the curve of her wing, prompting more moans from her into the pillow as he rubbed the highly sensitive and erogenous zone, her croup meanwhile grinding up into his crotch on reflex as it always did. This time, Nightmare added more emphasis to her moans and upward grinds, wanting to elicit a certain reaction from her servant.

He did not disappoint.

For some reason, as he rubbed her right wing now, Pip realized just how weird it was to him to enjoy making his Queen moan. He wasn’t sure why he loved to hear it, but it made something very deep in his animal mind satisfied to pleasure a mare like this, to hear the affirmation through her moans, and feeling her rump grinding up into his sheath, that he was pleasing her. Once more, not really realizing as he was so focused on massaging Nightmare and making her moan more, Pip’s penis had unsheathed, lying limp on her back but quickly stiffening in reaction to the soft fur and warmth of Nightmare’s grinding croup.

As she felt that ever-so-specific sensation of an unsheathing cock against her back, something she’d quite expected to happen given the fairly erotic moans she was intentionally adding extra-sexy emphasis to, as well as the view of under her tail that she’d given him earlier, Nightmare decided the time had come. “Mind rubbing a bit lower on my back, please? Right below where my wings are.” Nightmare instructed, feeling Pip squirming to maneuver himself to the point she’d asked him to tend to, before freezing up. Nightmare grinned, knowing exactly what he’d just realized as she felt his hard cock grinding into her back.

Nightmare looked back at him with lidded eyes and a soft smile. “Well? Is there a reason you’re not doing as your Queen asked?” she asked, her tail swishing now as her arousal grew. She could smell Pip's pheromones now wafting around, that alongside his rubbing on her wings triggering her pussy to start moistening itself for him, her breathing slowly increasing as her other alicorn parts started stirring to life.

Nightmare knew that since she’d ripped Pipsqueak away from his family and school, and refused to let him leave the castle grounds, that there was nopony to actually teach the colt about his hormones and the new urges he was undoubtedly feeling at his age. She’d also felt him grinding his hard-on against her back the last several times he’d massaged her, and she found she’d rather liked that kind of attention from a male after so long without it. She knew she’d need to teach the older colt about sex, and decided now was as good of a time as any, with the summer breeding season coming up soon.

Gasping at the sensations of soft fur and warm flesh grinding against his colthood, Pip felt himself blushing hotly as Nightmare looked back at him. He had no idea why his willy always decided to do this when he was massaging Nightmare, nor why it was doing it at all. He also had no idea why Nightmare had never acknowledged it before now, as it had happened nearly every time he’d gotten on her back since he’d gotten his growth spurt. “A-am sorry...?” Pip squeaked out, not sure exactly how to react. Nightmare wasn’t acting like she was mad or anything about his pee-pee being on her, but at the same time Pip had been taught back in Ponyville that his penis was ‘his private place’, and he was supposed to keep it in his sheath unless he was peeing.

“Whatever are you sorry for?” Nightmare asked, her tone deeper as it always was whenever he rubbed her wings, “I don’t sense anything wrong. Pip, could you please come off my back? We need to discuss something important.”

Sensing his doom coming, Pip was hesitant to do so, but eventually was forced to slide off as Nightmare got into a sitting position, the colt giving a quiet whinny as his cock ground along her back as he did. Immediately upon landing on his back on the bed, Pip’s hooves reflexively covered his erection as well as they could, which admittedly wasn’t very well at all. Nightmare noticed as well. “P-Please don’t be mad at my pee-pee being on you! I’m sorry!” Pip whimpered, fearing what might happen now despite Nightmare’s calm demeanor.

“There is nothing to fear, Pipsqueak, I’m not mad. You have done nothing wrong.” Nightmare said as her pitch-black hooves gently rested on Pip’s own of white, only inches from his cock. As she pulled his hooves away from his boner to no resistance from him, Pip looked away embarrassed and used his hooves to cover his face instead as Nightmare gazed upon his turgid member.

Pip's member was certainly not what she’d been expecting though; instead of a cute little colt penis, his was instead nearly the girth of an average full-grown stallion’s if not quite the same in length, his balls matching at a healthy plumpness. If she didn't know it was attached to Pipsqueak, she could easily have thought there was a fully-grown stallion laying before her. His eight-inch, light-pink penis was lightly mottled with dark blue splotches, a trait many stallions had that made each penis unique. His scent, also, was not one of a colt, but instead the musk of a potent, virile stallion; a scent which lit up her breeding instincts and further increased her nethers’ arousal.

“It is completely natural for a young stallion to react to being atop a mare in such a way, and nothing to be ashamed of. In fact, you should be proud of having a penis of such girth at your age! I know I like it.” Nightmare virtually purred. It had been what felt like forever since she’d last had such a young stallion at her disposal like this, most ponies fearing her too much to even approach her let alone become intimate with her.

Of course, Nightmare hadn’t cared at first, her lust for power and rage burning any other emotion to cinders before. Now that her emotions had calmed, her vengeful rage slaked upon killing that other ruler, she’d been feeling one all too familiar from her banishment on the moon and before when other ponies ignored her and her night in favor of her sister and her day.

Loneliness.

Nightmare wanted to be loved, wanted to be cherished as she always had even before her banishment. She wanted a stallion to tell her how beautiful she was to him, how she meant everything to him; to tell her how much he wanted to ravage her body and claim it for his foal. She’d been startled at such thoughts at first, of her desire of having a foal one day, but she also knew she’d need an heir eventually should anything happen to her, as well as having a deeply-rooted motherly instinct. Still, she knew she still had time to consider that later. Right now, her focus was entirely on the colt in front of her.

Put at ease by her words, as well as the soothing touch of Nightmare’s hooves on his, Pip let out a sigh of relief. “But...what is...why is it all...hard and stuff? It’s been gettin’ like that since I got my growth spurt...” Pip said, only receiving a small chuckle from Nightmare.

“Well, little one, it means you’re growing from a colt into a stallion.” Nightmare replied, watching as Pip’s penis throbbed once, a small bead of pre forming on its flare.

“But...what is all this stuff? Why do I have those weird...egg-things behind my willy?” Pips asked, voicing the question he’d had for so long.

“Well, stallions have their protective sheath, and inside that is the ‘penis’. The main components of the penis are the ‘glans’, then beneath the ‘glans’ is the ‘shaft’ of the penis. Finally, in the center of the shaft is the ‘medial ring’, a hard, highly sensitive ring of cartilage. Beneath the penis are two ‘testicles’, your ‘balls’, which produce ‘sperm’, contained within the ‘scrotal sack’, and inside the stallion’s pelvis are a number of accessory glands used to produce ‘semen’.” Nightmare explained, sounding like she was reading from a textbook. She’d indeed read over a modern health book to refresh her memory for this, and it clearly showed.

“...with mares, the outermost part of a mare’s anatomy is called the ‘vulva’, or ‘pussy’. Past that is the ‘labia minora’ and ‘clitoris’, and deeper still is the entrance to the ‘vaginal canal’...” Nightmare continued to explain clinically, as though teaching a class, oblivious to the confused look on Pip’s face, “...then above that is the ‘cervix’ and ‘uterus’, ‘Fallopian tubes’, and ‘ovaries’ which produce ‘ova’. When engaged in breeding while the mare is ovulating—”

Pip, meanwhile, looked at Nightmare like she’d grown a second head, with Nightmare stopping her lesson there when she noticed it. Of course he wouldn’t know any of this terminology, she realized, as he’d never been taught it. At this point she was completely aroused, with her now being inches away from a fully-hard cock after so long abstinent. Giving Pip a sultry smile, she decided that maybe a little ‘hooves-on’ education would be more stimulating. In more ways than one.

“Well, this is called your stallionhood, though it’s usually called a penis or cock.” Nightmare explained, giving the colt’s penis a gentle rub, earning a gasp and squirm from Pip, as well as an upward hump of the hips. As her hoof moved down his shaft to his medial ring, she got a wanting whimper from him as his hips instinctively ground his cock against her hoof. “This part especially feels really nice when touched, huh?” She asked, grinning at the pleasured expression on Pip’s face, “You can just call it your medial ring.” Finally, Nightmare used her other hoof to lift his sack and balls, getting a quiet ‘mmm’ at the sensation of the warm hooves on his sensitive orbs as she gave them a gentle rub, “Finally, these you can just call your balls, though they’re also called testes or testicles. They’re really important in making foals.”

Pip felt a twinge of fear as he felt Nightmare handling his very sensitive ‘balls’, with him having squished them a few times and knowing how much that hurt. When she didn’t do anything more than rub gently, Pip felt a warm sensation throughout his whole groin, his penis giving a gentle pulse of pre in reaction. “H-hokay...’ow do they help make foals?” he asked breathily, his head feeling light.

“Hm...well, since you've been through cellular biology already, this should make sense. They make a special kind of tiny cell called ‘sperm’, which can make a mare pregnant if she has its female counterpart of the 'egg' cell ready in her during her fertile time called 'estrus'. Each sperm contains half of a stallion’s DNA and each egg half of a mare's DNA. When they combine, the DNA's chromosomes match together and mix randomly, and that makes a new unique sequence of DNA for the foal. A single cell is formed, called a zygote, which then multiplies rapidly to eventually form a foal.”

“Is it like...a chicken egg? How does it make a foal?”

“No, not quite my dear Pip...just like a stallion’s sperm, a mare’s egg is really tiny. You can’t see it with your eyes, but it’s there. You know when I start acting all weird during Spring, Summer, and some of Autumn, and have my tail up all the time; when I smell a bit more...musky and leak that clear fluid all over?”

Pip only nodded. He had noticed that about her, more so as he grew older, and it oddly made him want to rear up on stuff. “That smell makes my...willy get all hard,” he admitted, his cheeks now in a permanent blush.

“Well, that means I’m in my estrus, my ‘heat’, and it means my ovaries, which are like your balls but are inside of a mare instead, probably released an egg ready to be fertilized by a stallion's sperm and later implant in my womb,” Nightmare explained, moving so she could place Pip’s hoof onto her lower belly with her own, “which is right about there. When a mare is in heat, and the stallion’s sperm and her egg meet and combine their DNA, she conceives a foal and gets pregnant, then carries and nourishes the foal in her womb while it slowly develops and her belly grows slowly bigger to accommodate it. Then, eleven to twelve months later, she gives birth to the fully-developed foal.”

Pip was speechless as he held his hoof on her lower belly, knowing her 'womb', where she could make and keep a foal for a year, was probably within an inch from his hoof. “Wow...but...how does the ‘sperm’ get into her belly to meet the 'egg' if it's made in a stallion's 'testicles'?”

Nightmare grinned. She’d been waiting for him to ask that. “Well,” Nightmare started, before rolling over on her back, spreading her legs and exposing her everything to the colt, “why don’t you take a look and feel around my underbarrel, then I’ll answer any of your questions?”

Pip, once more, was stunned as he finally realized what his hoof was now only inches from. “W-wow, you have a pee-nus too?! But I thought you were a mare!” Pip exclaimed. Sure enough, Nightmare had a completely black-skinned penis between her legs, a proud fourteen inches of mare-cock standing fully erect and proud with a retracted black-furred sheath at the base. A pair of massive, virile balls joined it, hanging down in a black-coated ballsack, and above her shaft were a couple of smaller teats, enabling her to feed any foals she may have in the future.

“Well, as an alicorn, I have both male and female reproductive organs. I can both give mares a foal, which I did many times thousands of years ago, as well as carry a foal myself if I choose to one day; I can have sex as both genders. We’re a rare breed of mares called hermaphrodites, also known as futanari, or ‘herm’ and ‘futa’ for short.” Nightmare explained, “While I could be considered either sex, I prefer to be called a mare.”

Pip’s hoof slowly trailed from her lower belly to her balls, slowly making his way down them and earning a twitch and quiet gasp from Nightmare at the first touch from another pony there in well over a millennia. After getting a permitting nod from her, his hoof trailed lower, gently lifting her heavy ballsack and revealing her wet, glistening pussy beneath it. The scent of her feminine arousal was intoxicating as was her masculine musk, her duel pheromones making Pip’s head feel light. Soon, his hoof touched her swollen lower lips, landing right on the cleft of it where it curved outwards; the curve that hid her clit, which she barely avoided winking.

“Ohhhh, that’s nice...that is my ‘vulva’, also called a ‘marehood’ or ‘pussy’,” Nightmare explained, before feeling Pip’s hoof moving up to the small cleft after exploring her swollen labia some, his hooves perusing the soft, arousal-swollen flesh; “a-ah...and in there, there’s a pink nub, called a ’clitoris’ or ‘clit’, that feels really good to have rubbed, kinda like a stallion’s flare or medial ring. Why don’t you give it a little rub and see what happens?”

He did as asked, spreading open her slit with both hooves and looking around her pink entrance, and spotted and started softly rubbing the mid-sized pink button. Pip was surprised to feel it pushing out against his hoof as he touched it, as well as earning a moan and upwards shift of the hips from Nightmare. He removed his hoof, seeing it wink again this time, exposing a flash of her pink entrance to him again and making a flush of heat go through his body. “What’s it doing? Are you OK?” Pip asked, not sure about her actions, but deep down, seeing her ‘pussy’ doing that for him felt...like he was doing this right.

“Ah, that’s called a mare ‘winking’. It was used by feral ponies to attract and arouse a mate during her heat before we could speak, as well as how traditional pony mating rituals went. Now, mares mostly do it for the same reason, as stallions really like it, but also to show how good her stallion is making her feel or while orgasming. Now, though, we can voice our desires as well.” Nightmare explained, softly stroking Pip’s penis with her magic meanwhile. While this was all fascinating to Pip, the big black mast of Nightmare’s cock was calling to him to explore it now, its light musky smell quite nice to him.

When Pip suddenly wrapped his hooves around her shaft, it took Nightmare somewhat by surprise, not having touched her male self in quite a while. She was sure he’d want to rub her pussy more given he was a stallion, but instead his hooves slowly stroked up and down her marecock, sending tingles of pleasure up her spine as it pulsed precum, showing her the colt had likely played with himself at least a few times as he hit all her good spots. “Mmmmm, that’s nice...” Nightmare cooed out, watching as Pip’s reticence was slowly replaced by determination. Determination to please his Queen.

Secretly, this was something Pip had dreamed about doing for since his puberty started, his nocturnal emissions indeed fueled by such dreams; of pleasuring his Queen’s privates, if not quite in this way. After a few moments of Pip rubbing her black, pulsing stallionhood, his other hoof rubbing her twitching asshole in exploration, Nightmare decided it was time to move on. “Mmm, as nice as that feels, I think I’d like something more now. Just do what feels natural.” Nightmare said as she stood, laying Pip on his back, before slowly lowering her pussy and ass onto his face as she partially sat on him.

As surprised as he was at his Queen’s sudden actions, Pip didn’t need to be told what to do now. Pip worked on instinct as her pheromones drove him on, his tongue licking on and into her fragrant pussy and clit, feeling the warm, soft flesh yielding to his tongue, and also feeling her ‘winking’ against his muzzle as well.

Nightmare, meanwhile, felt for the first time in what felt like forever as a tongue lapped in and around her pussy, the warm, fleshy muscle feeling quite nice to the lusty queen. She squeezed her muscles down, which in turn made her cock throb, more and more pre drooling down its underside.

Deciding to try something else, and hearing her moan as his tongue also reached up to lick over her clenching scrotum, Pip felt the weight of her heavy balls generally resting on his forehead, before licking within her marehood again. Nightmare felt as Pip’s tongue traced along her scrotum, following the trail of precum up it, before trailing back down her pussy again. Her penis was jerking and jerking more globs of precum all over the bed as he licked her winking clit, her magic gently rubbing her needing cock as she was being eaten out at the same time.

Pip thought her ‘clitoris’ coming out like that was strange but it made his hard little colthood throb in reaction, plus it made him feel good. It was making his lower belly sticky with his pre as he ate his queen’s pussy out, even sneaking a lick on the base of her shaft a few times, enjoying the musky, masculine fluids he found there.

Finally, Nightmare could take no more teasing. She needed this colt inside her now. “Come, climb atop me. Your Queen needs you inside her.” Nightmare commanded as she moved so she was laying on her back on the bed with her croup on the edge, spreading her legs - then her pussy-lips with her mid-blue magic and a clit-wink - wide for the colt in invitation. She could wait no longer; the foreplay nice and all, but she was needing to be filled.

Pip, seeing this, hesitated a bit, not really sure what to do. “Um...so I jus’ climb up on ya?” Pip asked, getting a squirm and nod from Nightmare. He got off the bed and simply followed his instincts, rearing up and placing a smaller hoof on either side of her on the bed, mounting her. His chest met hers as he started jabbing his hips forward unsteadily, so lost in his lust as he’d mounted his mare and felt her beneath him that he was just humping blindly now, for whatever hole his cock could find.

Nightmare grinned at Pip’s urgency; she always loved it when her bedmates got this desperate to mate her, so desirous of her body. So desperate to breed that they simply gave full reign to their instincts, like Pip was now. “I think it’s time to pop a cherry.” Nightmare said, all the while gently rubbing Pip’s cock with her magic, stimulating him that much more.

Feeling warmth after a minute of fruitless thrusts, Pipsqueak began to push inside that tight hole he’d found but was stopped by Nightmare’s magic holding his hips back. Pip whimpered at being denied, humping fruitlessly against her arcane hold on him, but Nightmare’s voice brought him back from his breeding haze. “Well,” she started, looking up at him, muzzle to muzzle with him in this position, “it been quite a long time since I’ve allowed anypony into my...anus.” Nightmare admitted, “How about we just do normal sex for now?”

Pip nodded, before gasping as he felt her tingly magic encase his cock, magically cleansing it, before guiding it upwards until he found a different warm, and wet, spot pressed against his flare. “Mmmk, just push your hips forwards niiiiice and slow.” Nightmare instructed, and Pip obeyed without question. This was what his body was telling him to do too, after all. As instructed, Pip tried to take his virgin journey into the warm, gently squeezing pussy of a mare nice and slow, giving shuddering breaths as his maleness was slowly consumed by warm, velveteen flesh...but failed as he reached his medial ring, his urge to get deeper overwhelming him as he thrust hard suddenly, bottoming out in the warm, gently-clenching tunnel.

Nightmare, on the other hoof, watched his face as she felt Pip slide inside, the face of pure bliss on her favorite little colt’s face making her feel warm inside in a way she’d not felt in a very long time. As he hilted within her warm, welcoming folds sharply, taking her somewhat by surprise, she could feel him trembling against her as she saw the face of a colt who just had his cherry popped; the expression of pure ecstasy, complete with his maw opened wide and tongue hanging out while panting.

“M-My Queen...I...I feel...” Pip said, feeling himself approaching the precipice he’d only plunged off a few times before, when he’d rubbed himself in his room at night, now approaching rapidly. The tightness in his pelvis was growing alongside the throbs, and he knew would soon deliver his sticky white stuff and mind-blowing pleasure as his hips weakly humped into her; he was so overwhelmed he didn’t even know what he was doing, just knowing he had to keep doing this humping motion, that it felt too good to even think of stopping.

Already Nightmare could feel Pip's flare hard as a rock and pushing out quite pleasantly against her inner walls as he pulsed rapidly inside of her, borderline orgasmic already at just the insertion, but Nightmare didn’t want it to end so soon. “Hold still, Pip. Let your body calm down. Wouldn’t want you cumming so soon.” Nightmare said as she placed a forehoof on Pip’s croup, stopping his humps and leaving him hilted inside of her instead. Though the idea of her pussy being creamed by the colt made her clit wink and her cock throb between them, but there was plenty of time for that later, she knew.

“’C-Cumming’?” Pip asked, only just coming off his near-orgasm enough to speak.

“It’s also called your orgasm, where your penis pulses a lot of white, sticky semen that contains your sperm, then gets soft? Surely you’ve rubbed yourself off before.”

“O-Oh...when I s-squirted when I rubbed myself...that feels r-really good. W-Why can’t I do that now?”

“Mmhm, it does feel good, but once you squirt you’re all done for a while, and I want to feel good like that too. It just takes mares a little longer to get there than stallions, and I do not like not getting my own orgasm.” Nightmare responded, “You may proceed when the pressure in your pelvis calms.”

As he got the go-ahead from Nightmare, Pip started humping when he’d calmed some, now able to savor the tight, ribbed passage of his queen as she squeezed down on him, giving quiet moans as he felt as her cock pulsed between them as well. The scents of both two males' and a mare’s pheromones were almost too much for Pip to handle, his hips seemingly acting beyond his control, though he didn’t mind. It simply felt way too good to stop.

Nightmare found that this felt as nice as she remembered her last time with a stallion being, despite the smaller body atop her instead of the hunk of a stud her last mate was, her vaginal walls being spread quite nicely by the colt’s sizable member as pleasure tingled along her spine.

As Pip kept mating her naturally, Nightmare thought of earlier as she was being fucked in such a vanilla fashion, of his flare pressing against her ponut. The naughty, taboo sensation she’d only felt a few times before in her thousands-years life. Once instilled, the thought of having a virgin colt busting a nut up her tailhole made Nightmare that much wetter and harder, the thought of taking his precious, virgin creampie up her ass something Nightmare now had to feel.

As Pip’s hips started slowly slipping his well-lubed phallus in and out of her canal at a steady pace, she let him hump a few times as he started to flare again, before stopping him hilted in her with her hoof again, earning a very displeased whimper from him as he was denied pleasure once more. “Pip...” Nightmare started, before pausing. Was she really going to let this stallion mate her, a queen, under the tail, she thought, before deciding ‘what the hay’. “I usually don’t let anypony put it in my tailhole, but I think I’ll make an exception for you, my special little colt. But, you need to be gentle at first, OK? No ramming it in when you get to your cock’s ring like you did with my pussy.” Nightmare said, getting a blush from Pip, “Pull out of my ‘pussy’ for me now, would you?”

“O-Ok...sorry ‘bout earlier,” Pip replied as he pulled his hips back and very reluctantly slid out of that welcoming, squeezing warmth, before feeling as his slick dick was once more grasped in magic and moved upwards now. He then felt his slightly-swollen flare pressing to that thicker, fleshy ring it was on before; what he now knew was her tailhole. Doing a quick cleansing spell on her bowels, Nightmare then used her magic to gently press on Pip’s croup, her heart pounding in anticipation, with him getting the idea and starting to press forwards himself against the tight pucker.

Even as well-lubed as Pip was from Nightmare's pussy, getting into this hole was nowhere near as easy as into her marehood Pip soon learned, him having to put much more force against that tight little donut of flesh than the lips and passage of Nightmare’s marehood, which had welcomed him in so eagerly. Soon, his efforts paid off as he slid in an edge of his flare, then his whole flare popped inside to a grunt from Nightmare, feeling an incredibly tight passage compared to her ‘vagina’, almost painfully so. Even still, he very much liked its tightness.

“Hoo-wow...that feels strange after so long without having something up there...” Nightmare grunted, feeling some slightly painful stretching from having her back door breached after so long, “...take it slow until I’m more relaxed. Don’t want you damaging anything in there from over-eagerness.”

Pipsqueak nodded and began thrusting into her ultra-tight ass slowly at first at her demand, but the lube from her pussy was enough to let him slide balls-deep before long, his smaller balls meeting her ass. He felt her own balls bounce each time he hilted, her erect cock leaking precum on their chests. Bringing a hoof up, Pip began to play with her cock, Nightmare moaning as she felt him humping her under the tail meanwhile.

Feeling her flare within an inch of her muzzle, and once again thinking ‘what the hay’, she, in turn, took her own flare into her mouth, her reactant moan stimulating her pre-squirting cock that much more. Moaning deeply as she gave herself a blowjob as Pip fucked her asshole, Nightmare’s eyes were sealed at the stimulation as he rubbed her lower dick off, her asshole squeeezing down on his spelunking member. Pip, meanwhile, watched in awe as Nightmare muzzle-fucked herself, giving her nose little affectionate licks as she did, before helping her in licking her cock with his own tongue.

All too soon, Pip started to hump faster into the tightness surrounding his member, feeling the pressure building again in his pelvis, the inexperienced colt lacking stamina. “M-my Q-Queen...I...I’m cumming!” Pip yelped as he slammed in hard and planted himself deep into her asshole within a couple minutes of starting; that deeply-rooted instinct to squirt as deep as possible into his mate taking over, his flare swelling as big as it could.

“M-Mmhm~...” Nightmare moaned from her cock-filled mouth, giving her permission for Pip to cum. After all, she was nearly there herself, and knew the warm squirts and pulsing sensation of a colt cumming in her would likely set her over. On a whim, Nightmare sent a tendril of magic up Pip’s ass, seeking out a special little spot in there and, finding it, started rubbing rapidly into his prostate.

Letting out a quiet squeal at feeling his pert ponut penetrated for his first time, Pip was overwhelmed by his most powerful, messiest orgasm ever as he released his colt-seed deep into Nightmare's bowels in rapid spurts in reaction to the overwhelming pleasure. He nearly passed out as he felt her magic rubbing in his ass,while he coated her insides with warm foal-cream, trembling as her back hooves locked against his croup in reaction, holding him deep as his tail rhythmically flagged with each squirt and he filled her ass up with his first orgasm to another.

Nightmare was meanwhile sucking her own flare as well as using her magic to thrust a magic-formed dildo into her pussy, all while being pegged in her ponut and feeling Pip's flare’s bottom tip pressing into her own prostate. Soon, with all of the stimulation, and not having had a pony inside of her for a thousand years, Nightmare soon followed Pip into orgasmic bliss from the sheer taboo nature of this all - taking the anal and penile virginity of the colt as her rectum and magic milked his spurting cock and his prostate of everything he had, all while blowing her own dick.

As she felt the orgasmic, rhythmic squeezing of her pussy and ass, feeling as Pipsqueak’s cock throbbed its profuse first load into her rectum, her pussy meanwhile gushed a couple squirts of her marecum as her cock flared and exploded her own huge cumshot into her waiting mouth, Nightmare trembling as her twin orgasms ravaged her mind and body.

Both ponies twitched and writhed as Nightmare’s tightness constricted Pip’s cock, the youth’s back legs trembling as he was kneaded of his load. Nightmare meanwhile sucked hard as her jaw ached slightly from the sheer size of her flare, gulping down her own semen and thinking it’d never end; that she hadn’t cum this much or this hard in many hundreds of years, indeed since she'd sired her last foal.

After both ponies had reached their shared orgasms and spewed their respective fluids to the other, with both twinging slightly in the aftershocks, Nightmare Moon pulled the exhausted Pipsqueak's chest up to her own chest, cuddling with the exhausted little colt who had worked so hard to please her and had done so well in accomplishing that. She then pulled him into a kiss, surprising him as she gave the colt the mouthful of her own sperm as he opened his mouth to her. He initially wanted to pull back from the slimy sensation, but quickly found it tasted even better than her pre had, the two then sharing her creampie as they made out, ending with Pip happily swallowing his Queen’s gift to him.

“T-thank you for this, my Queen. I...I really liked that. It felt...really good.” Pip said after his cock slipped from her ass as it grew too soft, quickly retreating into his sheath as he watched her loosened sphincter leak his off-white jizz, her belly lightly swollen with more of the same, "are...are you going to have my, um, foal now since I put all my sperms in you?"

"No Pip. You put them in the wrong hole, plus I'm not in heat right now even if you had squirted in my pussy."

"Oh. Aw..."

“Mmm, but I am totally keeping you. After tonight, you’re mine alone. You are my royal consort and stud now, my little Pipsqueak. I will decree it so tomorrow.” Nightmare said possessively, snuggling the just-stallion, “We’re definitely going try vaginal again in the morning, and I'll let you finish inside there next time. Who knows, maybe one day I will even let you be the sire to my heir, and possibly even be my king.”

“I...I would like that a lot. For you my Queen, I’d do anything. I love you.” Pip replied wearily, totally drained after his first time mating, already dreaming of what their foal could look like as he fell asleep in Nightmare’s arms.

“I love you too, Pip.” Nightmare whispered as she placed a soft kiss on his cheek, before cuddling up beside him and falling asleep herself while nuzzling her nose into his mane.

Author's Note

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Pipsqueak's Nightmare

NOTE: this chapter contains a single instance of foal abuse for character and scene building purposes. If this disturbs you, stop reading after the first paragraph and search the page for the words 'Pip quickly left' to skip the brunt of the portion with that content. Keep in mind you will be missing some character building as a result.

~

“’ere’s your tea, Luna.” Pipsqueak said with no small amount of disdain, the very small Trottingham Earth Pony colt balancing a tray, containing the meal he was sent up with, and almost as large as he was, on his back. His accent was that of his homeland of Trottingham, and he himself was a very small pinto-colored pony colt, white-coated with large brown splotches covering his body, especially large ones over his left eye and back. His straight mane was light and mid-brown, and was cut short, as was his tail.

“That is Queen Nightmare to thee, pony-whelp! We did not conquer all of Equestria to not be called by Our rightful title and name!” Nightmare Moon hissed as she struck Pipsqueak across the head viciously with a pure-black-coated hoof, the force knocking his small form to the floor. She was glaring daggers at him, making him crawl away in terror. The silver tray that was on his rump had hit the floor hard along with him, the fine Japonies tea set on it shattering on the floor, “WE ARE NOT THAT WEAK FOAL ‘LUNA’ THAT WE ONCE WERE!”

“Y-yes Yer Highness Queen Nightmare Moon!” Pipsqueak whimpered out as his hoof grasped the swelling lump where her hoof had left a red mark, tears welling in his eyes as his head throbbed in pain.

“’T'is better! Leave now, begone with thee thou ungrateful whelp, before we have thou lashed and then turn thee to a pile of ash! Thou shalt not receive dinner tonight, and be grateful for Us letting thou off easy this time. T’will not happen again, lest thou wish for worse!”

Pip quickly left without another word as fast as he could, wanting to get away from the horrifying, large mare. Was Nightmare Moon still a mare, he wondered. Was she even a pony anymore? Once out of the room he sighed, remembering for the umpteenth time how this all had transpired.

A few months prior, as the old tales of The Mare in the Moon had foretold, Nightmare Moon – who used to be Princess Luna, previously ex-co-ruler of Equestria, and sister of the then-ruling Princess Celestia - had returned from her thousand-year banishment on the moon to bring about eternal night. After banishing her sister to the moon in vengeance, then foiling the Wielders of the Elements of Harmony, by capturing the stones of the Elements themselves before they could be used on her when the purple unicorn known as Twilight Sparkle was still alone, Nightmare Moon was now the sole ruler of the land.

The first attempts at usurpation were dealt with with extreme prejudice to make an example of her power, leading to no further public attempts.

Pipsqueak looked out of a window in the hallway outside of Nightmare’s throne room, seeing the same darkness of night as he had for the past five days. Sighing, he remembered Celestia’s bright Sun rising each day, the warmth of it on his face. Pip felt tears coming to his eyes as he thought about how he’d never get to see it again, how he’d never feel its rays upon him again.

Nightmare had sworn the Sun would never rise again, and Pip had no reason not to believe the vengeful mare. ‘If ponies will not love Our night willingly, then they shall love it by force! The Sun shall never rise again! THE NIGHT WILL LAST FOREVER!’ he remembered her saying in her take-over speech after sending Celestia away and capturing the Elements, seeing the fury in her eyes as she did, then the pealing, manic laughter that followed it.

Now, as he looked out on the nocturnal landscape, he sighed again, looking towards Ponyville. He, and all other foals, had been taken from their parents there under the demand of Nightmare Moon, and brought to Canterlot, to be trained to be her servants in the way she chose. Taught to be her slaves for all intents, Pip thought bitterly.

“Evil coldhearted whorse, I wish I could...” Pip said in a hiss under his breath, rubbing his struck cheek. Letting that sentence trail as he noticed Nightmare’s chamber door’s thestral Royal Night Guard glaring at him, Pipsqueak quickly made himself scarce and left the area, heading back to his chamber to sulk. His broken heart was longing for home; longing for his parents, friends, and everything he knew that was torn away from him.

Longing for what it could never have again.

~ ~ ~

Five years had passed since Nightmare Moon had taken over as the dictator of Equestria. Her hot-burning vengefulness for her past subjects’ ignorance of her and her night had seemingly cooled some, with her overall becoming a more lenient ruler than the absolute tyrant she was before.

Nightmare had also, very reluctantly at first, taken over the duties of raising the Sun and Moon both, starting when it was brought to her attention by an orange-coated earth pony named Applejack that all the crops, trees, and other plants around Equestria were dying because of the lack of sunlight, within just the first week of her proposed eternal night, and that all of Equestria would starve if that happened. Not to mention the cost the being in constant darkness for so long took on ponies' physical and mental health too. Many were getting sick, or going mad.

So, not wanting her subjects, or more importantly herself, to starve, she’d very begrudgingly allowed for eight hours of sun per twenty-four hours for merely that purpose, leaving sixteen hours of night. The ponies relished in those eight hours, but also showed their due respect to the night as well now, not wanting to offend their new dictator.

When another nation had made threats against Equestria unless they were given an offering of Bits, military supplies, and royal guards in submission, Nightmare Moon had demanded a preemptive, overwhelming invasion of their land. Her ruthless surprise attack left its rulers dead by her own hooves, a warning to others about any future incursions against her or her land. This led many ponies to see her as evil incarnate to do such a thing, to take lives, while other said she was a very effective leader, keeping other countries and enemies at bay, by force if needed.

When criminal matters came up in her own land, including any kinds of uprising, Nightmare responded swiftly and brutally, keeping peace within her own country while still keeping her crown. Many ponies hated her for this, but others respected her. After all, she ruled with an iron hoof, but was also not treating her subjects like slaves anymore. Now she was harsh only to those who opposed her.

“Yer dinner, Queen Nightmare Moon.” Pipsqueak said as he brought in the tray and left it on her bedside table with a bow, his voice a deep baritone now and still holding his Trottingham accent; the one thing he still had from his old life in Ponyville.

In the five years since he was taken by Nightmare, Pipsqueak had grown from a colt who was small for his age into a young stallion now, adolescence hitting him hard with quite a growth spurt, as he stood nearly as tall as an adult mare now. He was still smaller for his age group, but he knew that surely he would grow more soon enough...and significantly more, if this spurt was an indication. The same silver tray that had nearly dwarfed him as a colt now was easily handled by him as he presented it to his Queen, a plate of various sauteed veggies, toast, and a side salad, upon it.

“Thank you, Pipsqueak. Always on time with my meal, aren’t you?” Nightmare asked in an even tone, giving a small smile. Despite her harshness as a ruler, Nightmare had become a much calmer pony to those around her in comparison to five years prior, her anger fizzling out some as it took its course and was vented. The event of starting a war and killing the foreign rulers herself likely helped with that. She’s also had learned Modern Eqquish* despite her initial refusal to, and indeed her demand that everypony else learn Ancient Eqquish instead, with her now being able to speak like modern ponies did instead of the ancient language she had before...though some still did slip in on occasion; “We are most grateful for thine punctuality.”

It had taken years, but Pip had actually started to respect Nightmare Moon despite what she’d done, seeing her growing as a pony as her hatred and emotional pain of before slowly burned away. The first time she’d smiled left Pip in awe, with him seeing normal, squared pony teeth instead of the fangs of before, him realizing that those must have simply been an illusion to instill fear in others.

“Thank ya, Your Highness.” Pip replied with a well-trained bow, before turning to leave.

“Halt.” Nightmare said curtly, leading Pip to do just that, looking back at her with some amount of fear in his eyes.

“My Queen?” Pip asked, hoping he hadn’t done anything wrong. Since she’d struck him that first time as a colt, he’d done his best not to upset Nightmare, lest it possibly happen again. Since then though, he’d never been hit again, with Nightmare indeed seeming to take a liking to him. He’d occasionally receive small treats or presents from her out of the blue, and not one Hearth’s Warming Day passed without a substantial amount of gifts from her.

At first Pip had rejected them all, destroying many of the gifts in rage, pining to go home to his family. As he realized that would never be, he’d accepted his new role and the gifts begrudgingly, then happily. After all, not every colt was treated as well as he had been.

Pip had always been cast aside by most foals in his past life in Ponyville given his smaller stature or Trottingham roots or accent, but Nightmare didn’t seem to care about his size or accent; only his loyalty. She made him feel useful. Wanted. Not just a tiny, worthless colt as he sometimes felt he was before.

At times he did wonder why he was chosen in this way, to serve her dinner every night; maybe it was because she saw a little bit of her past self, Princess Luna, in his personality, or maybe that she had some sort of thing for small colts like himself. What that was he could never guess, despite trying.

“Thou hath done nothing wrong Pipsqueak, no. You have been a perfect servant to me for all of these years. I was just wondering if we could...talk?” She paused for many seconds, “I’ve been having some problems lately in court, and would love to discuss them with somepony. They’re...really weighing heavily on me.” Nightmare asked, placing a hoof on Pip’s own.

Pipsqueak was stunned, both by Nightmare's hoof on his own and her words. This was the first sign of weakness he’d ever seen from the seemingly infallible mare, likely the first time Nightmare had asked another pony such a thing if her hesitancy to was to be considered. If her own expression was to be believed, she was confiding in him alone with this, making Pip feel...special, in a way. Like he was the only one who could help her, even among her many official advisors. “Uh, sure. What’s th’ problem?” Pip asked, seeing a flicker of a smile on Nightmare’s muzzle, her hoof gently squeezing his now.

“Well, you see...”

~

So it was now that when Nightmare Moon has something she needed to get off her chest, she’d go to Pipsqueak. She used him to wind down from a hectic day by talking everything out, with him even being asked to give her a back or wing massage on occasion.

While he was hesitant of the idea of touching the queen in such a way at first, fearing what would happen if he somehow hurt her, it soon became another thing between them alone. For some reason, Pipsqueak really loved to hear Nightmare moaning into the pillow like that as he kneaded her tired muscles, seeing her in a supine position before him, it triggering something within him each time he felt her tail flick against his rump. The moans always got much louder when he reached her wings, leading to him focusing on those more often. After, they’d always cuddle, with her holding him in her hooves and bringing bittersweet memories of his mother holding him like this in what felt like another life.

These past few months, Pip had been having some...problems with his willy coming out during the massage sessions, though Nightmare never seemed to notice it against her back, or at least never called attention to it. Instead her moans would grow more pronounced, leading to him sometimes even getting a full-on erection against her, but still he massaged her, not wanting to disappoint his Queen.

“Well, th’ last thing on yer schedule for tomorrow is goin' to Griffinstone for a non-aggression treaty re-signing with t’ griffins. Guess they don’t want a helping of wot ya gave that other country, huh?” Pip asked. Instead of getting a gentle chuckle and grin from Nightmare as he always did when that was mentioned, or even maniacal laughter at earlier times, she instead gave a sigh and nodded, indeed looking kind of...sad.

“Yes, yes, we wouldn’t want that to happen again, now would we?” Nightmare asked, before glancing in a side mirror...and noticing that Pipsqueak was looking at her behind! Instead of reacting with violence like she would have years past, she instead had a better idea; that perhaps it was time to put into play what she’d been building up to for nearly a year now.

Of course, Nightmare had caught Pip in the act of staring at her ass before, or even under her tail when it was flagged high during her estruses, multiple times before. She found enjoyment in teasing the colt, flagging her tail a little higher or swaying her hips just a bit more as she’d noticed he was looking, delighting in seeing his flare peeking out in reaction. She did both now, to a quiet gasp from the colt behind her, making her feel quite attractive as she felt his eyes roaming over her rump and marehood once more.

“So, what were your plans for the future before I came along and brought you here with me? What job did you plan to get? Did you want to have a family one day? Foals?” Nightmare asked as they walked, leading to Pipsqueak stopping in his tracks.

Pip thought carefully about the questions, with her never asking him such before. He didn’t want to make Nightmare mad, lest she possibly do something against him, so he simply smiled. “I only want to be by your side as long as possible, my Queen. Nothing comes before ya.” Pip said, and was surprised at how naturally those words had parted from his lips.

Nightmare felt her heart melt some at Pip’s innocent, undoubtedly loyal answer, such dedication to her displayed in those simple words. “Come Pip, I require your services in my room again.” Nightmare said as they reached her chamber door, sending him inside before looking to her two door-guards. “You two are dismissed for the night, and tell the next posting that they’re also off-duty.”

Getting a strange look from the guards, but with them saluting and nodding, Nightmare smiled as she then followed Pip into her candlelit bedchamber.

Nightmare had decided such loyalty from Pip deserved to be rewarded, and she had a perfect idea how.

Author's Note

* - the (non-canon) name of the language of Equestrians.

~

Well, so begins another story of foals and adults being naughty together!