PROMPT:
>be anon in equestrian prison
>everyone is very easy to manipulate 
>use your superiour linguistics and rampaging lust to sleep with nearly every mare in the place
>afterwards they would always insist they were in your herd
>you now apparently have a herd of 30+ mares, some guards included

***

>One mare in particular held a special place in your ravenous heart
>She was the guard who'd been posted outside your cell 
>You'd taken her the very first night of your sentence
>Cookies 'n' Cream was her name, now she'd made herself dominant mare of your herd, only answering to you
>To be honest the entire, er... "Incident" with her had been an accident, if anything she'd been the one to claimed you
>She was the best guard in all Equestria after all
>Ahh, you remember it like it was yesterday
>It had been a thunderously stormy night, the wind outside near deafening
>While it had you irked you'd found nearly every other inmate had been sent to a state of stress and panic
>That had been your first taste of this world’s absurdity [spoiler] aside from the whole being arrested by techni coloured sexually repressed dream ponies [/spoiler]
>What followed was your second

[that one blurry screen transition they have in shows when someone remembers things]

>So here you are, in a spacious, well-furnished room your captors had claimed was a cell
>It did a reasonable job at keeping out the raging storm because good fucking god was it coming down out there
>For whatever reason it had everyone on edge, actually no they'd already willing leapt over the cliff side, most of the inmates were endlessly crying from the thunder
>God it was so stupid, but not the dumbest thing you've encountered thus far
>Being arrested for self-endangerment, now that was the stupidest thing you'd ever heard or seen
>All you'd done was slip in a patch of ice
>Feeling none too happy about how pants on head retarded that was you were already thinking of ways to break out
>You were searching your room for valuable escape tools when you discovered that your door wasn't actually locked
"Fuck me swinging! Are these guys serious?"
>Looks like getting out of here would be as simple as walking right out the door
>Except they'd posted a guard outside your room, having deemed you a danger to yourself, requiring constant surveillance
"Shit."
>You have an idea, a pretty damn flawless one
>You were very big, she was very small. You just have to pick her up, steal her keys and lock her in your room as you saunter on out
>You might have a search for an umbrella before you leave but
>Creeping your door open you half expected to find your guard ready to pounce
>Instead you find her huddled up in a corner, shaking in her adorable guard uniform, a simple blue shirt and shorts, as thunder boomed in the distance
>You look up and down the hallway
>Empty, nopony, nothing but the rain pounding against the windows
>You sneak up to the mare, unable to hear your approach over the storm, nor able to see you with her head hidden under her hooves
"Sorry little pony."
>She looks up in shock at the sound and attempts to react as your arms lash out and grasp around her waist
>"W-what!? Let me go prisoner! NOW!"
"No."
>You begin to cart her back to your room
>"P-PRISON BREAK! SOMEPONY HELP!"
>Her shouts are lost in the deafening rumble of nearby thunder
>The sound of it makes the windows vibrate and causes her to lose all defiance in a snivel
>It certainly made it easier to haul her inside your room
>You slam the door shut to prevent her escape and toss her onto your bed
>"Guah! You don't scare me prisoner! You can't do th-
"Shut UP!" You bellow
"Your keys, give me your keys. Also are there any umbrellas here? Or a huge plastic bag?"
>"Like I'd tell you! And you're never getting my keys, I'm the best guard in all equestria!"
>You pick up one of the apples from the complimentary fruit basket they’d had in the room and move over to the ill-tempered guard mare
>"I'll have you know that I'd rather- grmrmmff!"
>Her words are cut off as your shove the apple directly into her open maw
"Didn't I tell you to shut up? Listen, ah..."
>You grab her shirt and find her name tag
"Listen Cookie 'n' Cream, christ what a name, I don't think you understand, best guard or not right now here's the pecking order. It goes me, then you. Now give me the damn keys."
>She spits the apple back in your face
>"Bite me!"
"That's it!"
>With just a single hand over her chest your lift her up and force her onto her back
>She whimpers and covers her exposed stomach with her hooves
>That was weird
>You look her over and find the keys around her belt
>Once you'd torn them off you let Cookies go and stroll to the door
>Stage one of your escape plan had gone off without a hitch
>Until you decide to take one last look at the pony you'd so thoroughly trounced
>Such a wonderful mistake on your part
>She'd gotten up but hadn't left the bed
>Rather she just sat, hunched over and looking like the saddest adorable horse in the multiverse
>Thunder roars from right above the facility and the mare breaks
>She start to sob and wail, a veritable flood of tears suddenly running down her face
"Fuuuuuuuck. What are you doing man?" You ask yourself
>You couldn't leave now
>Moving back to the bed you sit down beside Cookies
>Damn, how do people deal with situations like this?
>You do the one thing that feels natural, you cross your legs, grab the mare, put her between them, and hold her in a comforting embrace
"Are you alright? It's only thunder."
>"I know that! ~sniffle~ I-I've failed my job! How can I ever claim to be the best guard now! I'm a failure!"
>She continues to cry in your arms
"Hey, hey it'll be alright. Look I'm not going anymore, see? Staying right here."
>"Thank you prisoner." She mumbles out between ragged breaths
>Her sniffling doesn't stop so your start to rock her back and forth, stroking her from mane to tail
>You keep petting the mare as she cries herself out, having started she now found it difficult to stop
"You're a fantastic guard Cookies, you stopped me from leaving right?"
>"Heheh, yeah I did." She giggles before descending back into tears
>Jesuz these little things could cry something fierce
"And please, call me Anon, all my friends do."
>You feel her muzzle move up and down your chest as she nods
>Voluntarily or not her body relaxes as you continue petting her
>You are petting your guard... Why are you petting your guard!?
>Shit just don't make sense here
>Her crying stops and the intervals between each sob grows longer
"Someone must be feeling better." you say happily, taking your hand from her back and vigorously rubbing her belly
>You could physically feel the mood change
>"Ah~ A-Anon! What are? Mmm~hah! Oh! What are you doing!?"
>Unsure of what she was going on about you just look confused as you continue onwards
>She had such a fluffy little stomach
"I'm just trying to make you feel better Cookies."
>"Myah~ But we've only just met! And you're a prisoner! It could never work."
"That's the stupidest thing I've heard. Friends need to support their friends."
>You comply with her previous request and stop rubbing, instead moving your hand behind her ears and scritching away
>"We're friends?"
"Yeah we are Cookies. After this I don't think we can't be."
>You'd been referring to the situation as a whole up until now
>She may have taken a different interpretation
>"A-after this? But, but."
>She leans back and looks you up and down, a strange appreciation flowing through her features turning into a lustful desire
>"After this we're more than friends Anon."
"Hmm?"
>She leans back and hugs herself against you
>"Thank you for supporting me. So many ponies are scared of me for being so tough, I don't get to be close too many ponies."
>Things were getting a little strange
>More than friends? What was she going on about?
>Before you know it she rolls out of your legs and onto her back, this time her hooves remained splayed, further exposing that belly under her little guard’s shirt
>You look on in bemusement as she stares at you expectantly
>You remain unmoving, not comprehending a thing
>As you watch a vibrant blush forms on her cheeks [spoiler] how that worked with fur you didn't know [/spoiler] 
>"What are you waiting for?"
>She looks away
>"S-stop staring! Aren't you going to do anything?"
"Uhhh, okay."
>She stays splayed out, awaiting you
>Your hand moves out pushes onto her stomach causing her to moan
>That was... the wrong reaction
>Feeling unsure about your actions you choose to push onwards and slip your hand up her shirt brushing against belly that remained hidden
>Her eyes close as quiet, now sensual, whimpers escape her lips
>When her hooves descend to slowly unbutton her uniform do you finally understand what was happening
>Moment of realisation passed you're left grinning
>Fuck leaving prison now
"Oh, I know what you want you naughty pony."
>You help her with the remaining buttons and yank the shirt away, tossing it onto the floor
>"Ah~ Careful inmate, we wouldn't want to extend your sentence for aggression now would we."
"Don't threaten me Cookies. I've already told you, in here it goes me, then you."
>Now that you knew what was going down you were taking control again
>She gulps
"O-okay Anon."
>Damn you'd broken this pone already
>You place both hands on her underside and run your fingers through her short coat hair, making her squirm and cry out
>Pleasingly you locate a small belly button among the fluff and slowly run your fingers around it
>That has the poor mare near thrashing around the bed
>You'd figured by her posture and previous reaction that for whatever reason the stomach was a huge erogenous zone and judging by her response it certainly was
"Getting off to belly rubs, now that's something new."
>Her eyes open to look at you
>"It's LEWD Anon!"
"You're certainly making it that."
>You lean down and kiss her belly button
>"Ah~ You're the lewd one! C-can you do that again?"
>You smooch her belly over and over, getting tremendous satisfaction from the way it wade her body wriggle
>You can only envision her reaction to the main event
>Seeing the heavily panting, sweaty mare writhing beneath you already had you beyond rock hard
>You'd never been fussed with what you fucked, if it was conscious and consenting, you went for it
>Moving back up you rest one hand back on her soft gut and slide the other down to her rump, squeezing it through her tight guard shorts, they were basically spats
>"Ah~ W-what are you doing with my butt?"
"What you want me to." 
>Your hand moves under her rump and grabs on, pulling her crotch towards yours
>Feeling beyond horn by this stupidly adorable thing you push your groins together and grind back and forth, bodies naturally falling into a gentle thrusting rhythm as you rampantly dry humped
>Cookies can only scream out in ecstasy, her words falling away in a babble of whinnies and neighs and you grind against her sex
>If it weren't for the storm you'd have awoken everyone in the prison
>You slow your grinding, eventually stopping from concern
>She was too loud, were you hurting her?
"Are you alright?"
>She whimpers and wraps her hind legs around you, taking up your grinding motion
>"Ah~Anon. I-I feel weird. I’m on fire, it's too intense! You have to help me."
>She looks you deep in the eyes
>"Please don't stop."
>That's all the encouragement you needed
>Hands once again around her hips you push her against yourself and pound away
>You were likely being too rough with this little creature but you heard no complains
>Just endless groans and moans
>You'd been going at it for just a few minutes when she cries out again and tries to push you away
>"Ah! What's happening!?"
"Sorry did I hurt you?"
>"No! I... Anon I. It's so intense, I'm going to pee myself if you don't stop, or it feels like I am."
>You grin wickedly and start grinding again, this time much slower and harder
>You could feel her swollen lips spreading and parting around your cock as you pushed and thrusted up, despite both organs being hidden under clothing
>"Anon, no!"
"Shh, it's alright, let yourself go, follow the feeling. You want relief don't you?"
>"But, but hah~ AH~! ANON!"
>It would seem she didn't have a choice, as your continued stimulation pushes her over the edge
>Her small body jerked and bucked, her muscles clenching and spasming as she orgasmed
>You refused to stop grinding, grunting quietly as she scream, the sensation of her soft folds rubbing around your twitching shaft proving too delightful to stop
>Her cries, well, whinnies, easily outmatched the storm as she called out for more, little hips wriggling herself against you
>With a final cry and buck she relaxes and collapses in a sweaty tangle of limbs
>You feel a wetness rapidly running its way down your legs and look down to see the large wet patch on just about everything in a one foot radius from the action
>The room suddenly smelt of cookies and cream, leaving you both perplexed and hungry
>She was a squirter to be sure
>You flop down beside the panting mare and pull her against you
>"I'm sorry. I didn't mean it! Please don't hate me."
"It's only natural Cookies. I don't think I could ever hate you."
>You lay together a while before she starts to squirm once more
"Are you alright there?"
>"I'm sorry, it's still burning. C-can we keep going?"
"I was just getting started. But none of this high school dry humping shit."
>She blushes and hides her face away
>Not waiting for her to recover you get up and roll her onto her back, hurriedly searching for whatever kept her now wet pants on
"God damn it how do I get these off!?"
>"Oh, ah, there's a button under the tail."
"Right."
>You easily flip her over and lift her tail away, causing her to yelp
>The button was right there, just under the tail it wrapped around
>With her rear shoved in your face you could truly appreciate it
>Round, soft, well-toned. Most people would kill for an arse like that
>"Stop staring!"
>Right, you had a job to do
>You undo the button and painfully slowly pull them down, loving the anticipation and receiving a glorious sight
>She had a pair of pearl white panties on underneath, rather translucent after her recent gushing release, exposing her tender and swollen pussy
>You could make out slight movement under there, coming to realise she was winking at you
"You certainly are eager aren't you?"
>"S-shut up! Stop staring at me prisoner!"
"Hmm, no, you just look so... tasty and..."
>You push your nose against her mare parts and inhale deeply as she squeals in shock
"And you smell so good, just like cookies and cream."
>"Eh? You're weird Anon."
>A downright creep, but you didn't care
>You had to taste her
>Slipping off her panties you expose her tight ponut and dripping sex, eliciting a gasp that quickly turns to a squeak as you seal your lips around her small winking clit, softly suckling against her
>"Ah~ F-fuck! Sweat Celestia. Anon what are you do- Ah~! Oh by the goddesses."
>You greedily begin lapping at her, feeling her fat lips contort and move around your tongue as it moved up and down, loving her struggles to speak as you swiftly bring her to an ecstasy she'd never experienced before
"You taste so good." 
>Like cookies and cream, who would have thunk it?
>She blushes and puts her hooves over her eyes
>"I'm not tasty! You're just a pervert!"
"Are you telling me to stop?"
>In response her rump is pushed into you face
>Guess not
>Her clit no longer winked at you, remaining out and desperate for your mouth, she looked near throbbing
>Diving right back in you lick and taste her most sensitive parts
>Overcome by the phenomenal flavour you can't help yourself, even as her body stiffens and she cries out, spraying you right in the face with the sweetest liquid you'd ever tasted
>Fuck! What was this mare’s diet to leave her so sweet?
>She must actually be made of sugar, spice and everything nice
>Hungrily you lap away at the mare's rear
"Anon please! It's too much! I'm too sensitive." 
>But you can't stop, it was a trap! There was no escape for you
>Unable to pull yourself away her body continues to shake and twitch as she pleaded with you to stop
>You wouldn't, you couldn't
>Things only come to an end when you force another orgasm upon her, revelling in the spray of fluid, leaving her too weak to stand
>It took all your effort not to follow her decent and keep going. You could lose yourself in there
>She lays limply beneath you, struggling for breath
>Yeah, she needs a rest
>So for the second time you lay down beside her and she snuggles up against you
>"Take off your shirt."
>Off it flies
>She bites her lower lip at your rippling body
>"I'm so happy we arrested you."
>Lifting your head you plant a surprise kiss on her muzzle leaving an embarrassed blush on her face
>You'd think she'd be beyond embarrassment at this point
>She struggles to flop herself onto you, splaying her limbs over your body as she stretches out
>You find yourself already squeezing and massaging her arse
>"You can't help yourself can you? I've bedded a pervert."
"And you love it."
>"S-Shut up!"
>Your fingers drift down and slide over her labia
>Her eyes squeeze shut and she pushes her face into your chest, muffling her cries
>You slip a finger in her
>She was warm, slick and moist. You could feel her tugging against your finger
>But it soon proved too much for her as she pleads with you to stop again, still too sensitive to continue
>An evil idea comes over your horny mind
>You move your now slick finger up to the ring of muscle of her anus
>As they brush over her tail hole she stiffens, the tight ring clenching shut
>But as you swirl and massage your wet fingers around the edge you feel the muscles naturally relaxing
>"W-What are you doing anon? Why are you so obsessed with my butt? This feels weird."
"Do you want me to stop?"
>She shakes her head and hides it away yet again
>"I'm a dirty pony aren't I?" She mumbles
"You're a sexy pony."
>You prod your finger against her hole and push until you overcome the resistance, sliding into her velvety insides
>You wiggle your finger around feeling her insides and the sensation of her occasional involuntary squeeze
"Do you like it?" 
>"Mmhmm." Comes an answer from beneath her hooves
>This prison was fantastic, this mare, amazing. Your life couldn't be better
"Good."
>Reaching out to your limits you grasp a bushel of grapes
>She still refused to look out from under her hooves so she'd no idea what you had in store
>You pull your finger from her insides and grab several grapes
>Each one promptly found itself safely nestled in her colon with a few moans and grunts as you push them slowly inside her, feeling her sphincter stretching open and squeezing shut as they popped in 
>"Hah~ Heheh, you're lewd Anon." She giggles as the last small fruit disappears
"I'm not the one with grapes up my arse. Now give them back."
>"Wha-what?"
"You heard me, we can't leave those inside you, push them out."
>"But, I, it. Why did you do this to me!?"
>She hides her head away for the umpteenth time and whimpers as you feel the wet plop of the first grape landing on your stomach and rolling onto the bed
>She grunts and pushes out a stream of the ovaloid fruit
>"Is that all of them?"
>You gather them up and count them as they're tossed to the floor, except the last one, you were feeling a little hungry and horny as fuck, yet to have actually relieve yourself
>She'd watched you lustfully as you did it, drawing a perverse pleasure from watching
>"That was inside me Anon. Inside me..." 
>”In my butt.” she whispers
>Her hoof descends between her legs, rubbing furiously at her mound, focussing on her lewd thoughts
"I'd say you're ready to go again. Good it's about time I got my rocks off."
>"Your rocks?"
>You don't bother answering, lifting the mare up and putting her down, hoof rubbing all the while
>Rolling over you loom above her
"You know what comes next right?"
>She glances down at the bulge of your pants, gulps and nods
"Good."
>Of all the clothes removed that night your pants fell away the fastest, leaving your fully engorged member throbbing above her
>Her cheeks were red as roses while she stared at your cock, too embarrassed to speak and too enraptured to look away
>"Meep."
>You lower yourself down and shuffle closer to her
>Removing her hoof you rest your member between her legs, lifting them up to rub yourself against her thighs
>As your cock slides forward she pokes at it with a hoof, a brief moment of curiosity overcoming her desires
>You pull back and she looks at you with disappointment so push forward and rest there, letting the curious pony play around
>"It's so hard, it looks a lot smoother than a normal stallion."
>She prods it again as you leak pre-cum
>She leans forward and licks the tip, sampling your own sexual fluids
>"Mmm, salty." she says before accepting the first few inches of your cock into her mouth, reciprocating your earlier favour
"Fuck I love you."
>She releases you with a *pweh* and a trail of spit
>Her cheeks were red as ever, but she wasn't letting her embarrassment get in the way of what she wanted
>You let her legs down and pull back, lining yourself up with her marehood
>You could roast a marshmallow with the warmth coming from her, god she could be in heat for all you know
>"I don't think that's going to fit."
"You'd be surprised. I bet you have more control down there than you think" You say, rubbing your cock against her pussy, running it up and down her lips
>The way they moulded around your glands left both you and Cookies groaning in mutual bliss
>It was time
>You push your fearsome manhood into her cunt only letting the tip dip in and out
>Each time you pull out it makes a moist popping sound, causing her to shy away
>So fucking adorable
>You would have to be slow, she was right, as wet and ready to go as she was the size difference between you would make it a tight fit, despite her excellent muscle control
>So you continue to push just your head in and out feeling her walls stretching out to accommodate your size
>Already she was tugging and pulling at you in an attempt to draw you in further
>But you pull out completely and push yourself against her now puffy red folds
>"Nyah~! How are you still going?"
"Because it's only been like a minute."
>"Exactly!"
>Was she making fun of you or something?
"I'm going to ignore that. Are you ready?"
>A curt nod later you've lined back up
>You slide in with barely any resistance
>First your head pushes through, garnering a wonderful gasp from Cookies
>Your shaft followed, much slower, making her writhe in pleasure as you stretched out her insides
>She was so warm
>At last you find your pelvis pushed against her own, erection buried to the balls, which gently sat against her buttocks
>Her walls contract and squeeze your member, desperately trying to milk you of your seed 
"F-uck. Cookies you're good, and so soft."
>She smiles and blushes but it's broken by a series of moans as you slowly withdraw yourself, her snatch tightening painfully to prevent your escape
>"Ah. Celestia! Anon you feel wonderful. It's such an intense pressure."
>She press down on her lower torso, crying out in pleasure
>You could feel her insides squelching around you as her hoof moves back and forth
>Unable to pull yourself free you push forward, her marehood immediately loosening for your entry
"Fuck, you can do some magic shit down there."
>In response she produces the apple you'd previous stuffed in her mouth and fits it in your own
>"Shut up and fuck me prisoner."
>You've no choice but to follow an order like that
>You move your hands to her rump and lightly slap at them while slowly pulling out, being stopped and thrusting deeper inside her soft cunt
>Each time you slap her cheeks she lets out a pained whimper but when you ask if she wants you to stop she answers by putting your hand back on her rear
>So you go back to slapping her soft behind until it had gained a soft pink hue
>No longer willing to continue less you actually hurt her you begin brushing against her thighs, moving your hands down to her crotch, squishing and rubbing her pink labia, pushing in and out all the while
>Her spongy clit begins rapidly winking as she's overcome by pleasurable wails
>"Ah~ I'm c-cumming!"
>As she cries you push yourself in a far as she could handle, enjoying the tight squeezing of her pussy, and lean down to kiss her forehead, her crying dying down to whimpers
>"I love you Anon."
"Can you keep going? I'm almost finished over here."
>"Mmhmm." She answers dutifully
>"Just please hurry up I'm starting to feel sore."
>She hugs your cock tightly with her insides, smooth soft walls gently massaging you in a peristaltic motion
>You throbbed inside her as your pleasure rapidly intensifies 
"Oh my sweet god, keep that up and I'll be done in no time."
>She grins
>"Good."
>As you thrust she matches your movement with her own hips, keeping you inside her as much as possible
>Her marehood winks joyfully at you and she triples her internal efforts, her sex ravenously tugging and rippling around you
>It had suddenly become all too much, your pleasure had spiked to pure ecstasy
>Your natural reflex was to pull out as tremendous release flowed through your body, leaving you beyond relaxed
>But Cookies refused your exit
"Gah! What are you doing?"
>"What I want prisoner."
>You hold yourself off as long as possible but you'd already lost control
>Slow rhythmic thrusts became quick jerky twitches
>Your cock throbs, glands expanding at the end of each sporadic thrust as you shoot load after load of cum into the mare
>Each spurt sent waves of orgasmic pleasure through you
>"Yes! Breed me, breed your mare Anon."
>Yes you fucking would!
>With a final and powerful thrust you empty the last of your balls as deep into her as possible
>Finally she releases you, letting you out with a wet squelch, a veritable river of semen running from her slit down her rounded butt cheeks and puffy anus, to drip and pool upon the bed
>So much cum... You can only imagine the flood you'd left in her womb
>She was obviously thinking the same thing as she rubs her stomach in tremendous satisfaction, looking over you lovingly
>Her hoof descends and wipes some of your leaking seed from her fur, happily licking it up and going back for more
>You nestle up to the mare who sleepily rolls onto you, resting a semen-saliva covered hoof on your pec
>Gross
>"We're more than friends Anon, we're a herd now, and forever."
>You had no idea what that meant but you were happy enough about it, so long as you could keep that ass your own
"Definitely."
>The two of you fall asleep in each other’s arms, the storm outside long since ended