Chapter 3: Finding an Identity

You have a lot of trouble trying to get to sleep, Azalea seemed really upset but there wasn’t much more you could do with her. You wanted to talk to Rosy about this but she was still passed out in her own frame. Your drunken mind tries to recount all the details of what you know about your two new roommates. They used to belong to Celestia, their environment can be altered by paint or liquid, they can hear each other and you but you can’t hear them… The rules were very specific, and there were probably more limits and abilities beyond what you know. And your hands… It was as though the portraits give you the ability to create whatever you desire.

True, it wouldn’t do much good on your side of the world, but there was so much potential there. Were you a bit more sober you would think of how you could design elaborate portraits and landscapes for the mares, make a nice house, create pets and unique brands of dresses and clothings that would make the local seamstress jealous. The amount of good you could potentially do for the two is quite staggering.

However, you are too drunk to dwell on that aspect of it, Azalea’s depression took too much mental toll to dwell on now as you stare at your ceiling, and so your mind wanders to the other mare, Rosy. Namely some of the escapades she’d accomplished in Canterlot, as Azalea had regaled you.

… It’s not difficult to imagine it, the creamy orange mare spreading her legs, yanking her tail aside, her inscriptions edging on a group of stallions to fall completely under her spell. You recall how you couldn’t raise your eyes from her increasingly lewd commands earlier. … She didn’t go too far outside the norm but it was like the air itself was heavy under her command. You wonder just what all you would’ve done at the request of the sultry girl.

Only now you had the paints, and if your first impression was anything to go on, you could make any reality happen. A simple sex toy you could create through paint and your bare hands, or a vibrator, or anything. Chains, handcuffs… Hell. Your mind dances back to your life before Equestria. It’d been a curious thing transferring in that your memory only partially remained. You could recall instant moments but the specifics had all been wiped away and any attempt to reclaim them had left you with nothing more than a strong headache and the feeling you get from spinning in a circle while looking up for too long.

But one thing you do remember was the porn. Namely the questionable Japanese drawn sort. You wonder how she’d respond to a personal writhing mass of tentacles. It’s a painting, so it’d all be possible, wouldn’t it? Her hooves lifted high by one coil wrapped around her, her hind legs pried and tied apart by two others and a particularly thick, slimy prod sliding in and out of her, a smaller but equally slick one working her from behind. Her mouth gagging as two worked their way in and out of her throat, drool leaking from the corners of her mouth as her eyes sulk under her heavy lids. And as she is taken from every possible angle you’d be hovering over her, using her as your own sex fodder before drenching her in your own cum.

...Azalea might be right about you. You lurch up from your pillow, hanging your head forward, it was late and you were tipsy as all hell and from Azalea’s storytelling mishap to the stories you keep formulating in your own head, your cock is aching for attention. You check the small wooden clock beside your bed. You’d been musing about your room for a good while now, and it reads 2:07. You were already up late with Azalia and while the drinks exhaust you, your dick is too goddamn needy to let you sleep.

… You shouldn’t wake Rosy up, especially not after that event with Azalia. There’s already conflict between the girls. You were alone here for half a decade, you can handle a night of fapping alone and moving on. … Okay, so maybe you weren’t entirely alone. There was a time until recently that Pinks and Dash both made routine visits with you to the local bars in town and made your own share of fun.

… Not that sort of fun, mind. You’d never really made any moves on anyone in town. Not because of the species gap, on the contrary, you’d adapted relatively quickly from the usual attraction to female humans to the pony-ish aliens of this world. Both stallions and mares came to age at around the same gap humans did, and in turn a lot of traits that indicated sexual desirability were very similar here than they were at home. Thick hips indicated a healthy and sexy mare. Bright eyes, a well-kept mane, long legs, a slender neck. The only real difference in sexual characteristics that took a while to adjust to was the ‘breasts’. They varied in size but generally leaned smaller than most human girls by a fair bit. The location right above the marehood was also a bit strange.

That made the initial year a bit awkward, as most of the inhabitants seemed to not give much regard to clothes. Your initial issue was a sense of surreal ickiness at all the genitals around town every day for both genders, of all shapes and sizes. As you’d adjusted and assimilated the same sense of perversity you had in your original life, then it became a game of trying to hide the erection whenever a group of them innocent bent forward to draw in the sand or set shelves at the local shops. Admittedly it was an awkward erection that initially got you acquainted with Pinkie and Dash. No. Not really in the sexy way, more of the teasing, awkward way that eventually developed into comradery. There was more to that story but it was irrelevant. For now.

What isn’t irrelevant is that you can’t sleep, and tiptoeing as quietly as you can while trying not to fall down, you make your way to the hallway across from Rosy’s portrait. It was dark, the candle from your room and the starlight peering through the window from the front of the house just barely illuminating the mare. With a sigh you lean against the wall across for her and take a seat. She’s rolled over since, now snoozing on her tummy, her mouth slightly agape as she snores. Her mane is a ruffled red mess as per usual. You admit you had a vague hope you’d walk into the hallway to find her awake and playing with herself or doing anything to give you the excuse to get off. But seeing her at ease like this, maybe it was just the desire to not be alone at the time. You exhale with a dry smile, leaning your head against the wall and shutting your eyes. Despite the awkward position, sleep hits you hard.

You clearly remember the alcohol assisted fantasies about Rosy earlier as you find traces of them in the dream you have. Only this time, it was a little different. You keep fading to different intense visions, images of you in the painting with her. You see yourself grabbing her behind her back, lifting her up as the two of you dance tongues. You imagine her leaning forward, grinning back at you between her legs as she parts her tail aside, you sinking your shaft slowly inside of her wet passage. You see her riding you, her on top, slamming her rump up and down as her hoof massages her tummy. Then you begin to see Azalea… You feel her chastising begin to start and prepare yourself. It doesn’t, instead you find your positions swapped again. You see Rosy laying between your legs, your balls in her mouth as she rubs her hooves up and down your legs. And Azalea… she had a mouthful of you inside of her, bobbing her head gracefully and efficiently up and down your shaft. Her cheeks are pink and she avoids eye contact, only to give a startled moan through your cock when Rosy lifts her tail, pressing against the refined mare’s sex. Image after image of the three of you fucking in every which angle dance through your mind until…

Thunk!

You find yourself ripped away from your extremely pleasant dreams. No, goddammit it you were so close, back to sleep. Gotta finish-

THUNK!!

“W-what? It can’t be morning yet...” you grumble as your eyes part open. The first thing you see are those green eyes, lidded smugly and the grin of the mare. Her hoof was leaning against the glass where she was knocking.

‘Sorry, the sun’s not up yet.’

‘But someone certainly is...’

You feel a strong sense of warmth in your hand, then the realization that comes with fully waking up strikes you. You were in a pair of sweatpants, and in your sleep your hand had made its way down them, firmly wrapped around your burning cock. Through the sweatpants you can make out the tiniest stain of liquid where your pre had collected at the tip through your dreams.

“Wait, goddamn it, I didn’t mean-” She brings a hoof to her lips, giggling.

‘A pleasant dream I take it?’

‘Did I play a part? Maybe you sleepwalked to me?’

“Ugh…” Why did you decide to conk out here? You remember feeling very drunk and horny earlier but then… Instinct took over? You still feel a bit dazed but the alcohol had mostly reset itself to a dull headache at this point. Mostly, your vision still blurs. There was no point fighting your case, she had you already, judging by the slightly frightening grin she is poorly hiding behind her hoof.

‘But since you came to me of your own accord...’

‘Maybe I’ll let you take charge this time.’

She scoots closer to the edge of the painting, looking down on you where you sat, giving the illusion of everything but submission.

“What are you talking about Rosy?”

‘Well… I heard you and Azzy earlier.’

‘You know how the paints work don’t you?’

Oh boy.

‘Well, it looks like you have the power now.’

‘So why not let me be your toy for a while. You clearly want it.’

Her eyes dip down to your shaft as she finishes, her smugness almost palpable in the air. … With the way she was reclining her hips were very present, her ears drooping ever so slightly, every detail of her posture suggestive. You find yourself flashing back to your dream earlier. Consent couldn’t be implied any further than that, and she rolls sideways, sliding her hoof down her creamy orange body, past one of the pink nubs situated beneath her belly to her very well-rounded ass. She smacks her hoof against it, watching with a grin as the flesh radiated from the impact, a tiny pink hoofprint visible.

‘Go on… Go grab the paints and...’

‘I’ll be a good girl and do absolutely anything you say.’

Your head still brim with perversities, you stand up. You can tell from the heat of her stare you were still very much aroused. It must be around four in the morning right now… But you wanted some intense relief something fierce. You quietly tiptoe into the kitchen where Azalea should be sleeping… Ugh, it would be bad if she were to be awake. You hold your breath as you step in front of the portrait to grab the supplies. A few bottles of cider and the opened paintsets, and one sleeping Azalea… The coast is clear. You grab the collection in your hands before sneaking away. You don’t stop walking as you re-enter the hallway. Rosy is waiting, her hoof playfully grabbing lumps of ass before smacking herself, moaning quietly to herself as you approach.

‘Oh yes… I was ho-

‘Ah!’

You yank the portrait off the wall roughly, she tumbles back a bit, leaning her head up, her mane a mess. She brings her hoof from her thick set hips to her thigh, raising her limb to her sex to tease herself. You shake the painting again, keeping her from her self-ministered rutting. You don’t know if it was the alcohol, the headache, the hour of the night, or what, but if she’s claiming she’ll be yours alone for the evening...

“Hands to yourself missy, you touch what I say you can touch.” you grumble, hoping your exhaustion added to the charm. Her cheeks flush at the intensity of the order.

‘Yes, I’m sorry.’

‘Master.’

She keeps a completely submissive, straight face at you for the longest time as you stare her down after that, carrying her to your room. You can tell by her cheeks she’s fighting the urge of showcasing that knowing, sultry grin even now. Only now your little talk with Azalea has let on just how lewd this rosy mare actually is… Your cock is a constant aching reminder of your desire for release. You silence it as best you can, for now this was Rosy’s night. Azalea’s night was a bust, the least you could do was make Rosy’s first night something to remember.

You set the portrait on your desk, leaning against the wall. The mare had moved, sitting flat on her rump, hooves set just before her thighs, hindlegs spread so far apart for you it looked uncomfortable. Every detail of her sex was present for you, the way the creamy orange of her coat slowly shifted to the passionate pink of her marehood, her clit visible like a tiny little button, her walls as passionate a pinkish-red as the sunset painted in her background. The two buddish pink nipples above her pussy stood alert and sensitive. She didn’t have much mound there, but the spunky look suited her. She watched you intently, her eyes wanting. You lean back against the chair in your room, and take your time as you slam each container of paint on the desk.

Red. Yellow. Green. Blue. Black. Thinner. Brushes. Water. And one more bottle of cider. You glaze your eyes down at her. She flushes as you do so, your silence setting her on edge. You wonder if she was reconsidering her offer of letting you establish dominance. She actually breaks eye contact with you as you look over her face, her mane, the curve where her neck became her chest, then the way her tummy inflated to her feminine hips. Her tits both barely extending from her chest, nearly flat to contrast with how flared and always ready for passion her pussy is. But something was missing. Without a word, you take the paint brush you used earlier and clear your mind. It’s very easy to concentrate on what you wanted right now. You push the black, red, and yellow paints towards her, and dip the brush first in black and set it over her neck level.

‘Um..’

‘Master, what-’

“No moving now.”

It takes a few moments at best, but your hand knew this game by now. The outline came first, then the red color of fabric, and the golden yellow tag. the shades mixed themselves for you,and in no time at all your goal was finished. A slightly tight red collar fixed around Rosy’s neck, a golden little tag set beneath it, engraved.

“Now you can call me master.”

She holds the tag in her hoof, reading aloud what was inscribed.

‘Anon’s...’

‘bitch...’

She let it rest in her hoof for a while, you begin to wonder if the heat of the moment was a bit too heavy and you should’ve gone a bit softer on her. Before you can worry too much she looks you in the eye.

‘Ha, my first gift.’

‘I’ll never, ever take it off… Master...’

There was no ignoring the mischief in her eye, she almost certainly meant every word of that one. So much for inviting company over any time soon. But for now, she was going along with it. Which meant it was time for some real fun. You’d had a lot of little fantasies before coming over here, admittedly a slight fetish for domination and submission. Who doesn’t like some healthy spanking? Since you’d gotten here you’d had a few choice encounters with a few mares but not enough to get one into bed with you. Well, aside from one who very bluntly offered herself up to you one night two years ago on Hearts and Hooves Day. It was a… unique evening. She was clearly a fetishist from the second she saw you, so the sex felt very empty to you. Then we find ourselves now, with a mare that only wants to please you and you can’t even touch her in real life.

Ugh, your pessimism can go fuck itself, and you have just the cure. You get your voice as growly as you can without coming off as comical.

“It suits you, my Little Pet, now stand up and turn around for me.”

She gets to her hooves, looking a little nervous. Part of the act or genuine? You doubt you’ll ever tell but she swivels around for you, ever so slowly, raising her ass up, keeping her hindlegs parted, her tail covering her naughty bits.

‘L-like this...’

‘Master?’

“Not quite, raise the tail and don’t let it move an inch.”

A shiver seems to go down Rosy’s spine, but she lifts her tail high in the air. From this view you could make out her ass perfectly, and beyond that her marehood. A long trail of feminine nectar had made its way from her flared opening. Appears she wasn’t completely playing up the submissive streak as an act. Hard to believe with the events this morning. You don’t dwell, you had pussy to deal with. The next item wasn’t very complex but you still had to focus to create it. Luckily it turns out all sorts of focus assists with the creating process of painting. Sexual tension is focus in itself, and your hand again moves on its own, getting a thicker brush and soaking it in black before settling at the dock of her tail and working. Working… Working.

“And there we go. Don’t turn around. Yet.” She stays put, when her head starts to turn to face you, you interrupt her, “No peeking, Pet.”

Tight leather bands were wrapped around her tail, for about eight inches starting from the dock. They were tight enough to keep the fur taught until the bands ended. It forced the tail up and out of the way, removing her only means of ever hiding her sex. Not that you doubted she would anyways, but goddamn this was a mare that looked good tied up. You grab your bottle of cider and smack it against the table top, breaking off the lid before taking a long chug.

“Here I thought you were playing around, but look how wet you are, Pet.”

Her hindlegs tense at your words, thighs coming together, a single drop of feminine ooze descending betwixt her thighs and collecting on the canvas below. She stays true to your commands and doesn’t look back as she speaks.

‘I’m here only to please you, Master...’

‘But… Can I please touch myself? It’s-”

“Not yet.”, you’re grinning to yourself now, happy she can’t see you to break the illusion you have going. “I have a lot more work in store for you, Little Pet. Spread those legs wider.”

‘Yes Master...’

‘Nn...’

She forces her thighs apart, the fur mottled with her own dampness as she does so. Her hindlegs are spread awkwardly.

“Wider.” She tenses up before forcing even more distance between her hindlegs. Her fur stretches to match her stance, pressure pulling her rump apart, revealing her puckered anus. Her legs are starting to tremble. Now was the chance. You really have to focus on this next one, you’d seen this tool in a very, very filthy Canterlot magazine once and that’s all you have to go on. Your hand doesn’t automatically start on this one, instead it freezes a bit to process the order, but then jumps to work, mostly with blacks.

Two leather loops tightly constricting about six inches above her hooves. Between the two hooves a long, solid bar giving no leeway for free movement. It doesn’t take long after drawing it for the image to become a reality, her legs now forced that wide apart.

‘Oh...’

‘Oh Goddess!’

Rosy slides forward against the pressure forcing her open, sliding onto her chest. She could protest if she wants, the state of her sex screamed quite clearly she was enjoying being display in more ways than one now. Your head scans for all the different sort of toys you could create to really play with her, or more potential ways to tie and wrap her up. But goddamn, looking at that ass of hers, what you wouldn’t give to bring a firm swat to it to see her jiggle.

“It’s a damn shame I can’t reach you. I’d love to take a few smacks at that orange ass of yours personally…” You lean forward, whispering to the painting in a way that out of context would look really, really stupid. “-And make you really whimper for me, My Pet…”

You exhale roughly, her ass was backed almost to the pane, and you can see her front half shudder as your hot, alcohol scented breath misted over her rump. She can’t resist anymore, jerking her head back at you, her face mottled in sweat and face more red than orange. Her eyes were watery and she was drooling with need.

‘Oh if I could put my hooves on you through the glass...’

‘I swear to the Princess I would-’

She gulps loudly, panting.

‘Oh my, I broke the rule, Master.’

‘But you can punish me...’

The first bit catches you off guard. That look in her eye was more than just arousal. A part of you really wanted to know just what she wanted to do with you. The leaky ache between your legs even more curious. Until now you thought of this as a game she played, but there was a strange tension coming off her very painting that has come to hang in your room, making even breathing difficult. You have her in eye contact now though, and seeing the need in her eyes, you respond by taking your left hand off the bottle of cider and sliding a finger down your chest and gripping the bulge in your sweatpants. Her eyes follow, but the bottom of the portrait and how you sat at the desk hid the image of what you were actually doing. The same game she played with you earlier. You can talk to her in depth later, for now you had a mare to fuck senseless no matter how it had to be done.

“You will be punished, Pet, but you may go on.”

‘... Oh, you can… Hold the brush to the glass.’

‘-And if you don’t let go of it you’ll-’

“I understand.” you interrupt her, “Now head forward, or I’ll have to restrain your neck.”

She turns her head back, facing forward and away from you, slowly though. Was she wanting you to restrain her more? Maybe, but now you have a new trick to try. The next addition was a simple one compared to the rod separating her hooves. Wooden and smooth… You consider putting a few holes in it but you decide to not be that rough with her just yet. A nice handle, wrapped in tape. Your hand creates as you decide what the tool should look like. You notice that now your hand is actually working faster than you can think, finalized in that the final flourish on the paddle was created without you even needing to think of it. Written in fine, black cursive is the engraving: For Rosy’s Ass

You don’t raise your brush, instead focusing the tip on the glass. The painted paddle sinks into Rosy’s world, but as your brush connects to it, it doesn’t fall. It swings slightly left and right before bumping into Rosy’s rump from the right.

‘Ai!’

‘I see you know how it works now, Master...’

It’s… actually difficult. You can only see her in a 2-D plane. So you take care to learn the ropes first. You could move the paddle forward and backwards, but it took a lot of precision. If you press the brush firmly against the glass the object would move forward along the plane, if you eased your hold the paddle would ‘float’ backwards, levitating at the same level as Rosy’s rear. Ooh, it would feel so good to take a pop on her now, you can tell she knows its coming. She’s shivering a bit and her sexual aura was practically fogging the glass on her end. But not quite yet. You bring the paddle forward on her right side, near her face.

“You have permission to look to your right. I want you to read your paddle for me.”

You look past the mare’s ass as her head turns. Her eyes widen as she sees it. You can see her lips curl into an anticipatory grin, at least until her eyes dart back to see you glaring at her display of pleasure. She quickly reverts back to her anxious look.

‘It… says it’s for my ‘ass’.’

‘For Rosy’s Ass’.’

“You bet it is. Are you the sort of pervert who gets off on being bound up and spanked?” you lower your growl a bit, lechery shining through your words. She knows exactly what you want to hear but responds in her own method. She brings her lips to the paddle before distending her tongue, longer than most mares, to begin lapping up and down the smoothed wood.

‘Smk… Sm...’

‘...Smch… Smk...’

Your face heats up at the display, this mare… You have her bound up and at your mercy and she still has your sex in a vice, knowing just what to do and say to drive your loins mad. You pull the paddle away, trying to regain your breath. She watches the paddle leave, watching it rest against the right cheek of her ass, sinking against the felt-like fuzzy flesh. Her teeth sink into her lip in nervous excitement.

You consider making her look away, to keep it a surprise, but there was something addictive about watching her anticipating face as you raise the paddle up, just above her ass and get a few practice swings in. With every unheard ‘whoosh!’ you can see her lips curl, fighting that perverse grin she adores to display. Then you lower yourself down and wind up. A tiny bit of red is visible as she bites into her lip tight enough to break the skin, her body tensing as you flick your hand to the left. The paddle, slow at first, picks up speed in a wicked arc aiming at the rotund creamy orange flesh of her right ass cheek and-

‘AGH!!’

‘Mm...’

There’s a disappointment that you don’t get to hear that satisfying ‘THWACK’ for yourself, but the view more than accommodates. Like jello her ass radiates from the paddle, more of her mare juice dripping to the canvas, no longer able to collect at her thighs. The creamy orange flesh of her ass quickly converts to a bright red. You rest the paddle against the flesh for a while while you see her eyes water from the sting. Her jaw drops as she pants from the sensation, shuddering.

“Hey Pet.” you smile wickedly. She looks back at you, sweating and a mess.

‘Mm...’

‘Masterrr...’

“It’s so hot spanking you like this, pet. Look what you’ve made me do,” You don’t stand up, but you do siddle the chair back a foot, her eyes slide down, where the top half of your legs are now visible. You tug the sweatpants forward, letting your shaft stand tall and proud for her. Her eyes widen as you slide your hand up and down the length. She bites into her tongue now that her lip was bleeding and less of an option before moaning a response.

‘Then please abuse my ass till you’re fully’

‘... Satisfied Master… But...’ The text rewrites itself, slowly this time, as though it was taking her full capacity just to formulate speech.

‘When you are ready to cum...’

‘Please bathe your poor Little Pet...’

Those eyes again, those hungry, desperate, sinful eyes. There was no doubt you’d surrender to that request. It took all your energy to not forgo the whole roleplay and drench her now in your seed. You swallow a lump in your throat, trying to hide any anxiety in your voice.

“I’ll consider it, but this is punishment for looking back when I said no. No more looking back now until I say. Understood, Pet?”

‘Yes’

‘Anything at all for Master.’

She faces forward again, you casually thumb your fingers about your cock, applying just enough pressure to get more pre to leak out and dribble about your hand. You take the brush and with care, lift the paddle over the mare, resting on her left cheek this time. Her ass was two-toned now, her unswat cheek that delicious creamy orange, the other that fierce, flaming, pleasingly painful red. She tenses every time the wood presses against her ass. You bring the paddle closer still, smushing her cheeks together till they hide her genitals for a bit. Oh God the potential those hips had… And now you could come just that tiny bit closer to really affecting her directly. You slide the paddle up, and without giving her a chance to prepare swing the paddle down, colliding with her ass while both cheeks were still pressed together!

The ripple erupted from her cheek, before radiating to the other cheek, jiggling her whole ass mightily. Her hind legs jerk from the pain, but lock up in their bindings. Her marehood tensed, leaking not drops but a full line of her nectar to the canvas floor. Both her cheeks were now cherry red, and you’d only gone two swats in. The mare is panting, and an idea strikes you.

You pull the paddle away from her reddened rump for a bit, instead collecting a bit of your pre between your fingers. Rosy freezes in apprehension as you take the tip of your finger and rub it against the protective glass, right across her ass. Your essence phases through the glass, following your finger as you smear your cum across her cheeks. The volume difference still applies, giving more the impression that you just drizzled a full cup of your seed across her ass, coating the reddened thinly furred flesh with a milky white.

‘Ah...’

‘I’d know that scent anywhere Master...’

Rosy sighs, bucking her ass high as you smear her, making sure the pre smeared not just about her cheeks but sink into her marehood. She was balancing on one forehoof, the other resting at her belly, begging to please herself. Not quite yet. You take the paddle against her ass again, fine trails of your pre sticking between her fur and the wood of the paddle. Then, with care, you slide the paddle up and around her ass, the ooze coating her rump as her flesh shifts to accommodate the pressure of the wood. She shivers as you slide the paddle around her ass, to right under her tail. You slide the paddle under the mare and apply pressure upwards, forcing the wood to sink against her sopping pussy. The first time so far that you’ve allowed any relief to alleviate the burning of her marehood. A trail of drool falls from her mouth in front of you, her face still hidden.

The quivering of her legs and the heaving of her chest made it clear enough the reaction it was having on her. You hold the paddle tight for a while, letting the pressure build before pulling it away. As you do so, trails of her honey and your own mingle from the paddle, the wood dripping. Now a fine mess of a toy, you bring it up and bring another smack to her ass, rougher than before. A goopy blast of sexual juices erupt from the paddle as it strikes her sensitive rump, her forehooves cave and she falls to her chest on the canvas floor, her hindlegs still bound and refusing to let her fall.

‘Ngah!!’

‘Oh… Oh Goddess…’

You bring the paddle to her other cheek, she doesn’t even tense up anymore, in fact she sidles against the wood. A natural glutton for punishment. You can’t take the titillating view much longer yourself, you don’t wait before driving the paddle against her ass again. And again. By the time you’ve made six swings, alternating cheeks, the poor mare was a trembling mess of painful tingles of thoroughly smacked, satisfied flesh. Satisfied on the outside at least, you’d never seen a mare so thoroughly soaked, her juices contrasting the bright red state of her abused ass.

“You took your punishment well, my Little Pet. I guess I should reward you. … You can look at me.”

She slowly sidles to the side awkwardly, her ass still stinging, struggling to move in the binds on her hind legs. She faces you from the side, her eyes damp where tears had fallen, her face redder than before, stains below her mouth where she was drooling. At the word reward, her ears perked up, and the illusion was shattered yet again as that almost deranged smile pulled back her lips.

‘... Reward?’

‘Oh Master, I’d be… extremely grateful.’

Her tongue catches itself in the corner of her mouth, it takes an effort for her to bring her expression back to that of the slave. Admittedly you were breaking your character as well, you’re too tantalized at her bound and soaked body to dare let go of your manhood, finding yourself at the edge then painfully forcing yourself to hold off, not daring to release just yet.

“Hm, I was going to give you permission to touch yourself… But I think I have something better in mind. Stay standing just like that, sideways. I have a question for you, Pet.”

‘Hm?’

‘What is it Master?’

“What’s the largest thing you’ve ever fit inside of you?” Her face flushes, as though afraid to answer. “Don’t lie to your Master.”

‘... I… The Princess once drew me a dildo, horse in nature.’

‘It was… (there was a pause in the inscription as though she was afraid to say the rest
)bigger than my hoof.’

The inscription rewrites itself as she drops eye contact.

‘I used it for one night, it was special, it even filled me with fake cum...’

‘But it was too big… I walked funny for a long time after that. Why?’

You smile at the mare, she jumps when she realises you were already drawing again, This one was a bit more interesting to attempt, but if the canvas was where you saw her world from… The rope you are drawing around her chest is knotted off tightly, and your hand brings the rope to the top of the canvas. You draw a pulley around it, which materializes quickly, levitating. You had to focus on the mechanics of this as you draw it, forcing you to release your cock to bring your thumb to your temple in thought. Then you took the tip of the brush and cranked the pulley.

Success. The mare gives a shocked cryas you begin to lift her by the rope. Up… Up… Until she was a solid five feet above the ground. Her legs still caught. She hung awkwardly from the single rope, which you quickly rectified, drawing another rope around where her tail was already bound. You’d been told at a few bars in Ponyville that mares loved having their tails pulled, so you imagine having her whole ass suspended high and proud above the rest of her by her tail alone would amplify that feeling. The dazed look she gets as she is hoisted followed by a long, silent moan is more than enough indication your hypothesis was correct. You speak.

“The reason why is because you are going to take all of that size inside of you tonight. I’m going to pack you so full you’ll never feel satisfied without my help again.” You were pretty proud of that one, especially for the look Rosy gives you as you say this. At first it was a look of anxiety, her breathing slowing. Then her eyes lid heavily at you, if a pupil could become pure hearts it would be now. She gives you a tight-lipped smile before whispering to you.

‘... I knew you were a good one.’

‘Fuck me up and make me yours, Master...’

She doesn’t drop the smile this time, her suspension and situation too intense to bother with the mask of submission, instead she was watching you intently, reveling in her own bondage and excited for however you were going to use her next. It feels wrong on some level, but too powerful to dare stop. What you draw next is simple. Thick and dark green, phallic in shape. You draw in long, to the degree that even the most lucky of stallions would feel envy, and make it thicker than a can of soda. Your mind supplies hands with more details, bumps and ridges from the shaft of it, layers of thick rings around each nub. It wasn’t a simple pole of a dildo either, you make certain to give it a wicked curve, and you draw all of this right in front of her face. As you make her soon-to-be pussy wrecker more and more elaborate, her grin matches the excited tension wracking her body.

‘Oh Sweet Celly, Anon...’

‘You’re going to ruin me!’

She giggles as you put your finishing touches and hold the pen steady. The sex toy, stallion shaped with flare, was now under your own control. The practice with the paddle was worthwhile, as you had perfect control over the toy, that’s why you start by pressing the ridged shaft against Rosy’s cheeks.

“It’s going in by the count of ten. You have ten seconds to lubricate it.”

Words were needless, the second it met her cheek she reacted almost reflexively, riding her tongue up and down the toy before using the top of her lip to pull it horizontally.

“Ten… Nine… Eight…”

She fits a quarter of it in her mouth, gargling slightly to bulge both sides of her cheeks wide, drool leaking from the corners of her mouth, giving the tool a glisten. She lurches forward, gagging but getting half the toy into her throat. She draws back before lurching forward again, trying desperately to coat the toy with spit.

‘Ulp… Erp… Ulp…

‘Ell… Ulp…’

“Seven… Six… Five… Four…”

Her eyes close tight as she brings her lip to the tip, kissing and swirling her tongue around the flare, then takes a deep breath.

“Three… Two…”

She jerks her head forward, eyes widening with shock as she brings the toy to the ‘balls’ into her throat, choking herself. She stifles a cough and a gag, instead jerking her head back and forth, determined to coat every inch of that toy with her drool… You’re so impressed you forget to count. You pull the toy out of her mouth. She gasps for air as you do so, and you drag the toy behind her, reading the tip of the artificial shaft just inches from her hot, soaking nether lips. You notice your other hand had gone back to your own cock, you weren’t used to holding out so long… As you hold the dildo steady, you slide the portrait onto your legs, facing your lap. Rosy rocks wildly, shocked but still locked into place. She opens her eyes and sees her new view, your throbbing shaft situated right outside her painting, ready to drown her in your seed.

‘Oh Master...’

‘Are you close just watching little ole’ me?’ Her inscription changes.

‘Let me be your toy then...’

‘And feed your Little Pet every drop of your cu-AHN!’

You interrupt her as you slide the flare forward, parting her lips. Her inscriptions were hypnotic, if you let her get your guard down like that you’d blow way too quickly. That wasn’t your goal tonight. You see her whole body tense as you slide the brush forward, the dildo slowly passing inside of her. It’s thick, extremely thick. You see Rosy wince as she’s gaped open on it, only two inches in but the thickness alone gave her no ease in handling the monster of a sex toy. You rest the toy in at three inches, not even close to the full length which exceeded well over a foot and a half. Rosy’s eyes begin to glaze before you growl to her.

“You want more, my Pet?”

She nods weakly, her breath too heavy to properly formulate an inscription. All you see engraved beneath her is a mismatch of letters and moans.

“Then let’s see how much your pretty little pussy can take.”

You never really realized up until this point that having power had its appeal. Being under Rosy’s influence yesterday was intoxicating in its own way, but getting to see your personal little Pet shiver as you slide that goliath shaft further inside of her walls, parting her open, as her eyes slide back into her skull, unable to contain the sheer extremity of all the sensations binding and penetrating her… No feeling could ever match that.

You get the toy halfway inside of her, then let it rest inside of her. Her nectar dribbled from her lips, mixing with her saliva on the toy. Then you take your hand off of your cock to grab another paintbrush. You were no master in physics, but you couldn’t resist trying… You use your left hand to grab a lighter paintbrush, and situate it over the rope tied around her tail, suspending her. It takes a second but the tip of the brush grabs hold of the rope. Rosy feels this, she jerks her head back and sees the rope tighten as you begin to pull her forward bit by bit. She looks at you in shock at what you are about to do. You don’t give her time to dwell, you swing her forward until the flare was just barely parting her lips and let go.

‘Wait! I don’t know if I-’

‘OH SWEET HEAVENS!’

She slides back at a perfect angle, the arc you sent her in perfectly penetrating her. You don’t have to so much as move the dildo, she was aligned to penetrate while falling backwards. What you didn’t expect was for her to fit the entire length inside of her. Her eyes roll to whites as more drool escapes her, you see her body is shivering now and for a second you worry if the heat of the moment may have lead you to injure her.

‘OH GODDESS! THAT’S JUST...’

‘I’M SO...’

She struggles to speak but falls flat, whether that’s a face of pain or pleasure is impossible to distinguish, just that the massive, massive slab pressing her open had completely overwhelmed her rationale. But her body was still very much functioning, you see her yank forward, slowly and roughly rocking side to side against the rope, letting the toy fuck her fully at as many angles as she could. Oh hell, she’s into it. She’s breathing fast now, too lost in the sensation to slowly imbibe the musk permeating the situation. Her engraving matches as she yells at you.

‘Ohgoddessforgettheroleplaying-’

‘-Justdothatagainpleasepleasepleaseplease’

You grab the brush and respond to her aid, grabbing her rope, and pulling her forward again before slamming her backwards, repeating the same penetration earlier. She screams silently in ecstasy, you bring your other hand to your cock, furiously rubbing yourself raw at the mare’s responses. You’d give her a second to fully feel the pillar expanding her only to pull her forward again, and slam her back. She never adjusts, just quivers and moans. Tears make her way down her eyes to mingle with the drool, her face too red to even tell what her coat color initially was.

‘Yes! Yesyesyesyes-’

‘Oh Goddess it keeps coming!’

Juices were leaking in gratuitous amounts every time the pillar leaves her when she was rocked forward. How many times she’d came is impossible to tell, all you know for certain is your time was approaching. You lift her up, further than before, struggling to keep the arc perfect. You lean forward, feeling your head go light as climax approached. You had to make this perfect, wait for her eyes to open, to meet yours.

She does, and she closes her mouth, and grins. Her teeth were those of a normal ponies, but she gave off the intensity of a shark, ready to devour every sensation given to her and there was nothing you were more ready to deliver. You aim your cock at her body as you release the rope entirely. She swings backwards quickly this time, her marehood violently swallowing the ribbed pillar. She opens her mouth to cry out, and the second she does you cum.

Blasts of milky white erupt from your cock in waves, collecting at the glass and expanding, creating a creamy storm of your musky essence that rains on the mare. She lets her tongue hang, craning her neck up to moan and shout, getting a throatful of your spunk. Her hips shudder and quake, unable to tense herself up she’s forced to ride out her climax. Every gasp for breath is inhibited by the downpour of cum drizzling all over every exposed bit of her body. You still keep squeezing and tugging at your burning member, desperate to coat her thoroughly. Like last time she takes in large amounts of your cum showering her down, gulping visibly, only this time out of necessity for air to cope with the intense sexual sensation plaguing her. If you had one wish allowed at the moment, it would be to lock this moment in a loop forever. The two of you locked in climax, you blasting her into a pile of goo with your own cum as she spasms erratically at the pillar filling her up so brutally. You’d never understood what the term ‘sexual depravity’ really meant to this point, you always assumed sex was something mostly natural and sinless by nature.

But what happened tonight was a sin, the most exquisite, wonderful sin there was, and you’ll happily accompany Rosy into Hell for it. Azalea was absolutely right about you. You never free the mare from her bindings after you cum, you leave the pillar plugging her up. If she protests you don’t hear it, instead you grab her portrait and pull it close to your body before standing up from your chair and falling back-first onto the bed. Her portrait is atop you, and you tip it up. She’s rattled but still locked into place by ropes. She looks dazed and is a complete mess.

Her mouth stained with drool, her cheeks streaked with tears, her face and ass beet red for completely different reasons, her ass sticky with the cum smeared about it and her whole undercarriage a thick oozing mess of sex. She gasps, trying to adjust to the pillar still filling her before looking up at you, her grin returning but clearly exhausted.

“You look disgusting right now.” She laughs weakly, you continue, “And I’d give anything to be there with you right now to hold you tight in my arms to finish the night… Guess this’ll have to do.”

‘Ha… After all that in the end you are all for the sentiments, huh?’

‘Well I’m glad to have given you a good show, Master.’

“C’mon Rosy, this is the afterglow, you can call me Anon.”

It’s hard to tell if it was the pillar still inside of her that prompted the look she gave you, it was brief, but it was a look of irritation.

‘I like being your Pet though...’

‘I don’t really need a name, do I?’

Something about the way she was speaking was unsettling, especially the smile she wore. That thin, mischievous smile that emanated a perverse aura yet let no aspect of her true feelings escape.

‘In fact, I like Anon’s Bitch too.’

‘I was born to be your tool now, Master...’ The inscription shifts.

‘Use me whenever you want, and do whatever you want to me.’

‘That’s all the reason I need to keep living… I’ll be yours...’

She goes silent, resting her eyes. Did she pass out or fall asleep? You set the painting down beside you, staring at the ceiling.

You feel like you might have made a serious, serious mistake tonight. Rosy stays silent throughout the evening despite her bonds. You don’t get any sleep.

The sun raises shortly after you and Rosy’s escapades are done. Rosy’s silent, you peer over and find that the leather binds and the toy had served their time in her portrait and had faded away. Rosy was laying on her belly now, still soaked in your seed and still a bit of a messy wreck. Her collar however, remained. You figure it’s probably due to how much focus you put into it. Azalea mentioned something about how focus determined how ‘real’ a painted object was. … Great, now Rosy was going to have “Anon’s bitch” wrapped around her neck for who knows how long.

Your body feels satisfied, but you feel mentally exhausted. You’d heard people talk like Rosy before she fell silent before. You hope in the back of your head that maybe she was just caught in the moment. You admit you were rough with her, but she was so accepting of every advance. Hell, the way her stare fixated on you gave you the impression that if you didn’t push every button to the limit she’d just be disappointed. You lean forward, sitting at your desk and put your hand to your head.

It’s been 24 hours since you’ve acquired two roommates. In that time you made one cry and fucked the other one twice; the latter is calling you ‘Master’ now. This is out of hand. You figure a shower would clear your head and take a look at Rosy’s portrait. She’s all tuckered out, and you imagine she’ll be conked out a while. Still, you take your paintset again, and to the side, focus on some basic tools. A small washing tub, a scrub brush, and a towel. You don’t know enough about mare shampoos to really know how to make spa worthy products but its a start. Luckily the mare doesn’t wake up.

You pull off your clothes and enter the shower, turning the water on hot. Painfully hot. Lack of sleep or not, you needed a game plan. While the idea of fucking about with Rosy for a long, long time and taking the chastising from Azalea wasn’t a bad idea, you could see this going out of control quickly. Azalea would be asleep a while after all that alcohol and Rosy from sheer exhaustion. You’d spend the next few hours preparing a meeting between the two in your living room when eleven in the morning hits. You prepare a pot of coffee in advance, Azalea wakes up first. Rosy is still in your room crashed, you figure she’d wake up and clean herself when she’s good and ready.

‘You’re up early?’

‘Have a nice night?’

It’s not hard to guess that she knew you’d been up to dirty business after you left her. She still looked too exhausted to put up a fight, her eyes were a bit bloodshot from the alcohol and the crying. She kept her blanket wrapped around her, it was starting to fade a bit, soon it would be gone from her canvas too.

“Sort of… I’m going to have a bit of a get together during this late breakfast. Would you like some coffee?”

‘Can you draw tea, sir?’

‘Herbal would be ideal but...’

She’s not being as aggressive as she was when she’d first arrived. Maybe she can see the apprehension in your eyes of how everything seemed to be… off. You’re familiar enough with tea to bring the taste to mind, creating a mug for her. The steam rising from it meant you even had the temperature down correctly. While it wasn’t entirely your talent so much as the enchanted nature of the paper, you feel a little proud of your abilities. She sips from the ceramic cup you drew, and smiles softly.

‘Not bad’

‘At all.’

“... I wanted to ask you a quick question.”

‘Is it’

‘About her?’

“Yeah... “

She removes her lips from the tea, removing her blanket, and fixing her hair. She puts a hoof to her temple before responding.

‘I’ll answer what I’m willing.’

‘But I would rather avoid any controversial conversing this early.’

“I get it, I’m not asking about any of her private affairs. Just… Back before me, with the Princess or even before, has she been… okay?’

Azalea pauses, giving you a curious gaze, before sighing.

‘Give me’

‘A marker.’

You do so, and she quickly takes it by horn and begins to write.

‘Rosy, as you call her, it’s hard to say where she stands. I only reveal this to you because while it intrudes on privacy, if we are to live together this sort of open communication is vital. Her personality is… unusual. This may be largely while we clash so violently, well aside from her promiscuity. Back in Canterlot, she’d had a history of flirting with everyone, even the Princess. I recall one evening she was turned down by a stallion visiting from Saddle Arabia who was staying in the royal hall beneath us.’

Azalea sighs.

‘Even though it was the first time her charm failed, she… didn’t respond well. She was angry initially, told him to commit a few anatomically impossible acts upon himself. But then she left her portrait, refused to look at anyone or say anything. She did this for three full days and nights. Even the Princess she refused to respond to. When she came back on the fourth day she was still somber. I don’t understand how the mare thinks. To be honest I don’t want to.’

‘But she lives entirely on pride in her own body, as nauseating a concept as I may find it. I’ve known her as far back as I can remember, and not once has she ever truly opened up to me or anyone for that matter. Every time I would try to talk to her about… anything that wasn’t scandalous, crude, or dangerous she would switch the conversation to trying to flirt with me or leave the painting with a brief apology. That’s why I said I could never really leave her. I find her distasteful but… sometimes when she’s alone and thinks I’m asleep, I look at her and I see...’

A loud thumping noise interrupts your conversation, sounding off from the back of your room.

“Speak of the devil, that must be Rosy.” Azalea rolls her eyes at you.

‘As expected.’

‘You did bed her again.’

“... We’ll all talk about this over breakfast.” You say, leaving Azalea to her tea to go get Rosy.

Author's Note

Whew, sorry for the wait but I did meet my once a week update deadline. We have a long one here that I extended even longer because I didn't want it to completely end on sex again. To be honest this chapter wrote itself more than I did, it was intended to be another Azalea chapter with some very brief Rosy play but... Well, somehow twenty pages of pony BDSM happened.

You guys know how it is. As usual I greatly appreciate the comments, likes, bookshelf-ers, and all you groovy cats who take the time you read my stuff. More Azalea next chapter.