Tippy Radsworthe by Anon

(Anon / Pinkie)

M/F, paddle, stocks, juridical, bruises, sex, unfinished, non-consensual

 

(22/04/2013)

 

 

---

 

"Well this isn't what I expected at all! Where's the canoe, what good is a paddle with no canoe. And why are we going canoeing at the Town Square anyways, I know a great river just a few hops down-"

 

The judge groaned, pressing his face into his hoof before giving the pink pony another tired glare. I kept quiet, I tried explaining what the situation was the night before, but it seems to have went in one ear and out the other. For a pony awaiting fairly severe punishment Pinkie seemed not phazed in the slightest.

 

"I'll repeat this once more. We aren't going canoeing. For the destruction of town property-"

 

"-I said I was sorry for mixing the cake batter and cement mix up."

 

"-And for harassing official authority, we are forced to take action. Now, being a current weilder of an Element we can not subject you to prison or banishment, however this has become a recurring issue, so we're going to have to use a more dated means of punishment. Fifty licks."

 

"Fifty whats? That's just unsanitary." Pinkie pouted, whether she was being sincere or not was impossible to tell. The judge pony promptly stepped away from the podium, pointing a hoof to the town hall shackles, dated and obviously having not seen use in a long, long time.

 

"I can't do this. We went over this last night anyways. You, being not from around these parts but under employ by the Princess are legally allowed to provide Pinkamina Pie her options, the town guard will observe the sentence is carried out. I'm going home and will try to get rid of this awful headache."

 

The sounds of doors slamming. The hall was emptied out for the occasion, all that stood here was a mischeivous pink pony, two town guards (one with a suitcase), and one very awkward human wondering just how to explain what was going on to an oblivious pink filly.

 

(Fuck, I don't care for anon in equestria, so our protaganist is now a burly young man teleported to Equestria by the Princess to determine whether human integration would ever be beneficial. His name is Tippy Radsworthe.)

 

"Um, Pinkie Pie..."

 

"Yes, Tippy?", a cheerful grin despite the heavy atmosphere of the hall. Of course.

 

"Look, sometimes people make mistakes. And well, some ponies go further than others, and well, something had to be done to make things right, right?"

 

"Right!"

 

"And you know we can't let crime go unpunished, no matter who the perpetrator, right?"

 

"Well, duh."

 

"You're the perpetrator."

 

Apparently that's what got through, as that instant her ears drooped. You can only assume her heart fell just as much as her eyes began to water.

 

"But I'm a nice pony! I wouldn't hurt anyone, really!"

 

God, this was going to take a while.

 

"I know, I know you're not a bad pony, but you made some mistakes, and you have to make up for them. That's why you have a set punishment."

 

Pinkie hoofed at the dirt, not wanting to lift her eyes. We hadn't even hit the first lash and already this was heartbreaking.

 

"Okay Tippy... Anything to be good."

 

"That's the spirit," a town guard gave me an annoyed sigh, best speed this along.

 

"Pinkie, for repeated offenses you are to be subject to fifty lashes."

 

"Lashes? Fifty!? I don't know if I have that many to give!" In an instant the pony began desperately attempting to pluck the lashes from her eye, failing miserably with hooves.

 

"No, not those lashes, swats. Fifty swats with a paddle. Please Pinkie, pay attention because you have a choice."

 

"Choice?"

 

"You have to get hit fifty times with a paddle. You can have the town guard arrange to do it in town as a public punishment."

 

Pinkie's pupils dilated a bit, clearly nervous now.

 

"Or... Because of good deeds done for Equestria and because of my current position under the Princess, I can... I could deal the punishment here and now, no one but me, you, and the two guards ponies. But I can't go easy on you because we're friends or the guards will take over and do it themselves."

 

Her ears drooped, her hoof was now a few inches in the sand from nervously swiveling it about. She sighed a very un-Pinkie like sigh and mumbled.

 

"I'm scared. I don't wanna be hit, but if I have to in order to be good again, then I'd rather a friend do it for me."

 

A selfish part of me wished that she had gone with public punishment delivered by a guardspony. I don't want to hurt Pinkie, the parties, cider parties, I'd only been here a month but already I'd grown attached to the colorful characters around town.

 

I was jarred from my thoughts by the guardpony tossing the suitcase in my lap, with a flare of his horn it opened. I pulled out the paddle. Wooden, with six holes drilled through. Sanded down but definitely aged. The words 'Ol Reliable' were inscribed on the side. Pinkie looked at the paddle nervously. I gave the most apologetic look I could muster, a sad shrug was what I got in return.

 

Seeing that I wasn't rushing her to action the two guard ponies lifted the sullen Pinkie. It felt like the color left her as she was hauled to the podium, and her front hooves and neck shackled down, followed by her hind legs, shackled slightly ajar. I was surprised to see the front shackles were cruelly lowered well beneath the hind shackles, forcing the victim to be stuck facefirst in the dirt, hind-quarters up.

 

A mix of misery and apprehensison could be read in Pinkie's eyes, her muzzle in the dirt and her hair having lost its sheen, parts of it falling down and spilling across the dirt. I stand, paddle in hand, dumbly.

 

"Look, we have work to do so get on with it."

 

A hoof beckoned me forward, I almost tripped but was standing behind Pinkie Pie. Her tail hung weakly to the side, her bright pink buttocks suspended in front of me.

 

In a shameful recess of my mind I couldn't help but notice how nice of a figure she had, thick rear and wide hips-no, this is wrong. I sigh, counting to ten in my head. I hear a weak whimper from the dirt.

 

"Tippy... Please get it over with, I can't take waiting like this.", her voice was a forced calm, speaking slow and deliberate. It dawned on me she was trying to hide how scared she was just to make me feel more at ease with the situation. Even now she was putting others before herself. A flare of anger hit me, I suppressed it as best I could and raised the paddle high in the air. I whispered a 'sorry' that the patrol ponies couldn't hear, brought the paddle down and-

 

Whack!!

 

I had to resteady my arm, not at all expecting the paddle to fly that fast. A gasp followed by a meek whimper left Pinkie's lips, smearing dirt into her coat. Already her flank was growing more red than pink, staying it's normal color just in six spots where the holes in the paddle were notched.

 

"One!", the Patrol pony barked. Forty-nine to go...

 

I felt a knot twist in my gut knowing what still had to be done. Any sense of arousal that may have seeped into my subconscious over spanking the filly passed as soon as I heard that whimper. But I had to keep going, the patrol ponies explained yesterday that there is a pace required in a paddling. No more than fifteen seconds max between paddles no less than five.

 

"Snf, just... Keep going.", despite her attempts at monotone little cracks of the normal Pinkie were audible.

 

Smack!

 

Another hit, the left cheek gave a strong shake on impact, instantly turning bright red where this impact merged with the last. Pinkie's body gave an involuntary shake as she grit her teeth to not cry out. Another sniffle.

 

There was no way to make this easy for her.

 

Smack!!

 

"Three!"

 

Smack!!

 

"Four!"

 

Smack!!

 

"Five!"

 

It was only five in and Pinkie's backside was already glowing red, her tail giving off an occasional involuntary twitch in response to the pain. Her inner thighs were quivering, forced to support themselves because of the shackles. A cold sweat had formed on the poor pony's forehead. The first tear hit the sand with an audible 'drip'.

 

I held my breath, drew my hand back...

 

Smack!!

 

"Six!"

 

Smack!!

 

"Thirty-six!"

 

By now Pinkie's ass was brighter than her hair, a few welts and bruises already noticable. Her sweat was now pouring down her face, mingling with tears. I'd always assumed Pinkie was unphasable, but she was weeping now, only stopping to let out another weak howl as the paddle fell. My arm felt like jelly, but at least it was almost over. I raised the paddle again, Pinkie's body stopped trembling to tighten up, doing all it could to brace for the impact, anything to lessen the pain.

 

SMACK!!

 

... "And that's fifty! Unshackle her."

 

The second patrol pony galloped to the shackles, and undid the legs first. Numb and weak Pinkie's back half just fell sideways, collapsing against the dirt. When her front legs and neck were unbound she didn't even bother moving, just kept weeping softly.

 

A bit of bile grew in my throat. She was a wreck, her flank and thighs full of bruises and welts to the point of near bleeding. Her face was flushed and eyes damp with tears, you could make out the matted fur of her cheeks where tears had been falling. With disgust I handed the paddle to the patrol pony.

 

"Don't take it personally, someone had to do it. Your payment."

 

A beat up leather sack fell into my hands, jingling with coins. Fifty bits. Pinkie looked up at me miserably, I felt sick just having it in my hand.

 

"Send the proceeds to Sugar Cube Corner. I've no use for this." I handed him the bag, the pony shrugged and left. His partner followed, leaving me and Pinkie alone.

 

It was quiet aside from the sniffles, just me standing over Pinkie, who was shaking. A long, awkward pause permeated. Do I apologize? Does it even matter? Maybe I should just leave, Pinkie was the nicest pony, no, creature I'd ever met, and I hurt her.

 

Damn it, I can't just leave her alone. With all my energy I stepped towards her, she recoiled.

 

"I don't blame you if you hate me. I kinda do too. I need to take you to Nurse Redheart's to make sure there's no infection.

 

Another pause before Pinkie choked out, "I just... Want to go home."

 

There was no life to the voice, just sadness, it just dawned on me this may very well be the first time she's ever been truly hit before period. And it was by a 'friend'.

 

"I... Don't think I can get up."

 

I sighed, being careful as I could I took the pony into my arms. I initially held her by the stomach to avoid putting pressure on her bruises but she stopped me.

 

"Please carry me on my back, I don't want ponies to... See." Humility.

 

I obliged, carefully wrapping one arm around her upper back and the other around her thighs, doing the best I could not to further irritate her rump. She flicked her tail around the mass of bruises as best she could, and we began the long, awkward walk to Sugar Cube Corner.

 

It was chilly out, early evening. Pinkie and I both recieved a share of dirty looks as I took her home. Whether her wounds still shown or simply because of the rather intimate look we had at the moment I wasn't sure. Pinkie's face was red and she looked miserable. I should have grabbed a blanket to wrap her in first.

 

I opened the door to Sugar Cube Corner to see a very concerned looking Mr and Mrs Cake. Mr Cake quickly snatched the pony from my hands, examining the damage.

 

"Sweet Celestia... This'll take days to heal, Mrs Cake, go get something for the swelling."

 

They were ignoring me, I don't know if they were aware I was the one to carry out the punishment, but seeing the two doting over the grown mare like she was a filly again filled me with guilt.

 

"... Hey, thanks for worrying, but I think I'd like to just lay down for a while. I... Need to talk to Tippy."

 

I can feel the hard gaze piercing my back from Mr and Mrs Cake as I lifted the pony up again and began my walk of shame up the stairs to her bedroom. The familiar bright array of colors blinded me as usual on entry. 'Subtle' wasn't exactly in Pinkie's dictionary.

 

Taking care to set her down on her stomach, I set her down on top of her pastel sheets, as well as set the ointment down on her nightstand. I couldn't help but look at her, the sick red stains padding her flank, another wave of guilt.

 

-Which was interrupted as she turned her head to look up at me. She was a wreck, sure she always kept her hair in a mess and never bothered much with hygiene beyond a rinse now and then (how she maintained her coat was a mystery) but this was the first time she truly looked miserable.

 

The shame was too much, I couldn't keep eye contact, trying to find something interesting on the wall to stare at. I couldn't even say anything.

 

"Tippy... I don't hate you."

 

I wasn't expecting to hear this of all things, especially not as the first thing she said directly to me personally after what happened.

 

"Why not? I hurt you, very badly. I'd hate me. It's not fair, you didn't even know what was going on till the last-"

 

A poor attempt at a laugh left the poor mare, "Nya ha... I knew what was going to happen Tippy, I know all about the Equestrian Legal System."

 

What.

 

"Well, Twilight taught me most of it on a rainy day. I was guilty of causing elevent-thousand bits worth of property damage, and the bit of cement that kinda hit Officer Trots knocked him enough for an assault warrant. The usual punishment is five to ten years in Canterlot Dungeons, but being exempt from being jailed it only made sense to fall back to the old methods."

 

"What."

 

"I'm not as dumb as you think I am silly. That's why I had you do it. I was angry, but mostly just at me. ... Ok a little at you during the whipping but now mostly just at me."

 

I had to sit down beside her, fingers on temple. She gave an aching 'oof!' as the bed shifted to support my weight. You think you know some pony then they go and surprise you.

 

"... Even if it was the better option, I still feel like shit."

 

"Sh-"

 

"-Bad. I feel bad about it. I'd never want to hurt you, Pinkie, regardless of the situation."

 

"Well if you're still upset, then why don't you help me?", her voice was getting some life back into it, she was still a wreck, but some of that brilliant glow was coming back to her eyes.

 

"Of course, anything."

 

"Anything, anything?"

 

I tried to read her, but it was pointless, she had that oblivious half-grin on, wide-eyed despite how dishevelled her mane is. Whether it was a facade of hers or genuine innocence I'll never know.

 

"Of course Pinkie."

 

"Well in that case... I'm smarting like you wouldn't believe! Or maybe you would, that blue bottle there should help." With a bit of effort to slide her arm from under her chest she pointed to the array of ointments on the nightstand. The big blue bottle was instantly distiguishable, it was called 'Timberaid'.

 

"You mean this?"

 

"Yeah! We also keep the house stocked, I tend to hit my head every now and again."

 

I popped the lid (it snaps right off, I assume a screwable lid would be difficult for hooves) and pour the ointment into my open hand. It felt cool and refreshing to the touch. Then it dawned on me.

 

"Wait, you want me to run this on..."

 

"My rump! Duh."

 

I had no grounds to argue, considering I was the cause, but all of a sudden seeing Pinkie's bright red rump and sweaty form made my own head fuzz up.

 

"Hello, Equestria to Tippy! Oh don't tell me you're shy, you just got done whipping me an hour ago!"

 

Another giggle, but it made me sick to my stomach at how quickly she was already making jokes about the affair, being easily forgiven is one thing but-

 

I snap out of my self pity party and begin to lather the ointment a bit. It reminded me a bit of biofreeze, though not as intense. Approaching the pony I sighed, and thinking chaste thoughts brought my hands down to her rump as gently as possible.

 

She still gave a shudder under my touch, and even through the gel I could feel how raw the flesh felt, heat radiating from the final licks where the pink was bright red.

 

I tried to rub the ointment on as gently as I could, terrified at the thought of hurting her again as my hands loosely smoothed around her flank.

 

"Tippy."

 

I looked up to see Pinkie turned around looking back to me, clearly trying not to laugh.

 

"It's not gonna help if you don't rub it in, something distracting you?"

 

Yet another statement that would definitely be teasing if it were any other pony, but again with Pinkie it was impossible to tell. Trying to hide the blood rushing to my cheeks I shook my head no, and put more pressure.

 

Pinkie gave a jerk followed by a sigh of contentment as my hands runned up and down her backside, from around her tail to circling her haunches. Despite the welts her ... distractingly wide hips and form made focusing on the ointment hard. Had to distract myself, say anything...

 

"So... Is this helping at all?"

 

"Yesss..." Pinkie sighed, clearly content, under my hands I could already feel all the tention in her body slowly loosen up. A part of me felt glad that she was already doing better, another part wishing she wasn't enjoying it quite so much as for some reason it felt like her room had heated up ten degrees despite having the window down. I could only hope that with her exhaustion and the 'massage' she wouldn't notice the effect she was having.

 

Giving one shameless caress of her cheeks I slid my hands away, wiping them off on a towel nearby. A sad sigh came from the pony, but it wasn't one of my pain anymore, for that much I was grateful. Now if I could just clear my head...

 

"I'm still kinda achy. That rubby, feely massage you did felt preeetty good." Pinkie chimed, with all the subtlety of a beached whale.

 

Giving it felt good too, but for the wrong reasons. I was about to tell her to try and rest until I actually got a look at her. The look in her eyes was not the look of an ailing pony, more sly than anything else, and the tint in her cheek was prevelant enough to match her other cheeks.

 

(Fuck it, we're going a bit cloppy. Gotta finish this bitch.)

 

"Wait, are you-"

 

"Hold it, you said you'd do anything, anything. That's not one, but two anythings! And the second anything I want is for you to keep going."

 

An answer without an answer, typically Pinkie. I knew there was no use with protesting, trying to keep my breathing smooth I brought my hands to her backside again, both swollen cheeks resting in my palms. There was no use keeping a clear head now, the moans she's given and her sensitive rump in my hands already had my extremities aching, all I could do is hope she doesn't notice.

 

Passion got the best of me, I couldn't help but give her cheeks a slight squeeze, she gave a moan followed by a deep exhale. A shudder worked its way down her spine before wiggling its way through her tail, which brushed about my face.

 

"That doesn't feel like a massage Tippy!"

 

"Ah, sorry! I just-" I jerked my hands back, feeling very stupid. She was injured for-

 

"Hey, I didn't say stop.", she said with the most mischevious grin, her eyes shining blue, "but maybe... Start somewhere a little less smarty."

 

Okay... That's a bit out there, but it was still innocent Pinkie Pie just-

 

"Make me feel good and I may just take care of what's been pressing against my hip the past fifteen minutes."

 

Oh sweet Celestia.

 

"Wait, are you pulling my-"

 

A flick of that pink tail against my face silenced me, as well as a 'shh' from Pinkie.

 

"Not yet, now as agreed agreed, as agreed?"

 

Despite her puns, her face was bright pink, nervous? Hard for me to tell, but the sense of euphoria of this pink pony was overwhelming me. I leaned over her, and brought my hands over her shoulders. As I clenched down, gently at first, she gave another cute little sigh as her joints melted like butter.

 

I put more pressure into her back, leaning forward, practically laying on top of her as I rubbed deep from her neck to her shoulders, to her upper back. As I straddled her, I couldn't help letting my clothed but fully standing manhood graze her back as I worked. Even the slightest friction felt amazing after the rollercoasted that was today. Her response was a giggle between deep panting breaths.

 

Taking a fine nibble of her ear (the scent of her naturally sweet mane mixed with the more musky scent of sweat from today was intoxicating) I worked my way down. Every inch of her back I worked my fingers, down her spinal column, then down her sides. A part of me felt tempted to roll her slightly to rub her stomach and a few more delicate areas too, but my judgement still wasn't entirely gone.

 

I continued my way down, sliding my hands across her hind legs, sliding my fingers across her cutie mark to where the red began on her flank. She was tense in anticipation, and judging from the new scent in the room was just as in the heat of the moment as I was.

 

"You are one incredible pony..."

 

"If you keep this up you'll be an incredible human! ... Well, I guess you're already kinda incredible since you're the only one I know, but still, when-ah!"

 

Using silence as an excuse, I grabbed her tail and held it back to give a kiss, right on her cutie mark. I worked my way through the tail, down to her ass, giving it a very gentle squeeze. Being sensitive from the abuse, she tensed up and moaned.

 

Not a giggle, coo, or sigh; a moan. The first I'd ever heard her moan. It wasn't the filly-like outburst common from Pinkie, but the audible ecstasy of a true mare. A mare hidden past many barriers of childlike wonders but a mare all the same. And one with needs.

 

Giving the cutie mark a lasting lick (motting the fur) I drew back, taking each of her cheeks in hand, both were still warm and smooth from the work earlier, and fell right into my hands, tender. I gave them a gentle squeeze, rubbing one down and one up, each gyration receiving another luscious moan from the mare, both from pain and satisfaction. A stain was already making its way onto the sheet between her haunches, which were pressed deep against the mattress, each tense moment punctuated by out mutual heavy breathing.

 

"Tippy, I need you to-"

 

I had a good idea where she was going, or at least I hope it was since I couldn't hold myself back anymore. Gentle spreading her legs I could get a good look where the red ended and her real pink began. Her marehood lay wet and flared, begging for attention. Were I a lesser man I'd have stripped and had my way then and there, but there's a time and place for everything.

 

I leaned my head forward, I could hear Pinkie's deep breathing break into short gasps, I couldn't see her face but it was clear she was nervous. Was this her first time? There was a lot of firsts today.

 

I leaned forward and took a strong wiff, her marehood had a musk to it that drew me closer, not the sweet scent of her hair, but something deeper, the mature side of Pinkie always hidden behind that poofy tail.

 

Starting at her lower belly I kissed her, then high, I peppered the area around her marehood with teasing kisses, each one spawning a twitch of her hind legs and a deeper gasp. For the moment, she was mine and mine alone, and it was high time to strike.

 

With as much care as I could muster in my state, I moved my hands from her legs and gently opened her marehood, the bright pink glossed with her own juices blossomed for me, and without hesitation I licked her. Tasting Pinkie from the inside, something I never would have even thought possible before today, was now happening.

 

The taste was powerful, and matched the musk of the mare. Not the sweet candy scent her coat would give away, but the taste of an actual mare. I let my tongue rest inside her, gentle lapping up and down her walls. Each movement of tongue brought out moans and even small shrieks from the pony, doing all she could to keep still.

 

I really hope the Cakes already went to bed.

 

"Mm, T-tip, I...", what followed was a series of moaned syllables that might have been words in her head but were all lost coming out. I finished my way up her sex, taking care to give her knub a gentle suck followed by a kiss to force another long, drawn moan from the pastel mare.

 

Before I could pull back for air, she'd drawn her hips back, grinding her sex against my face, her reddened ass and back visible to me above her marehood. Happy to oblige, I licked her again, this time rest at the top to slide two fingers down her walls. A fine trail of her natural juices hugged my fingers as I did so as her pussy twitched in anticipation for more.

 

I eagerly complied, running circles around her marehood with my index finger then slowly sinking it in, just to the knuckle. Her back arched reflexively against the new feeling, shuddering.

 

"Ah! Tippy..."

 

The response I wanted, I slid the rest of the finger inside on her, her own muscles twitched and the digit, pulsing around it as if trying to suck it deeper in. I gave her another lick, the pulled the finger back, slowly. The sigh of disappointment was quickly replaced by another moan as I sunk it back in, pumping the digit into her, her whole body shuddering with each movement.

 

Pinkie kept trying to coax me on, but every attempt to formulate anything beyond simple moans and 'yes's was mixed too deeply with her own panting to be distinguishable. Every moan and twitch of her body ripped through my own body like lightning, driving me to want to go deeper and deeper, to make her entirely my own.