Never Fail

by Shrinky Frod

First published

Trixie has paperwork. Trixie does not want to do paperwork, as Trixie's tricks never fail. Starlight has a plan to make paperwork more rewarding.

The Great and Powerful Trixie does not need event insurance.

She especially doesn't need to fill out more than twenty pages of contracts, disclosures, and guarantees that if anything goes wrong, the company can come seeking internal organs to recover their losses.

And yet, without event insurance, Twilight will not let her put on her show for the School.

Realizing that her marefriend is on the verge of cancelling the show rather than filling out the forms, Starlight comes up with a plan to make the chore more rewarding.

And hopes that Trixie's right when she says she never fails.

Technically a CTS fic, but you don't need to know a damned thing about the Clocktower Society to enjoy the fic, promise!

CW/TW: F/F sex and relationships, BDSM, breathplay, hornplay, snuggling, and the demonic force that is insurance paperwork!

Story written for the CTS Writing Prompt: "Writing becomes a sexy chore," 24-hour format. If you like this, and would like to support my literary efforts, please check out my ko-fi or Patreon links!

Chapter 1

View Online

“The Great and Powerful Trixie does not require ‘event insurance,’ because the Great and Powerful Trixie does not perform tricks that fail!” Trixie turned her nose up, crossing her hooves over her chest. “Princess Twilight is merely attempting to meddle with my show - again!”

“Trixie,” Starlight groaned, “Twilight isn’t doing this because it’s you. She’s doing this because she got the bill for repairs from the Onesversary play!”

“Trixie never should have sold the pink one those fireworks,” the showmare muttered.

“No, no you shouldn’t have,” Starlight agreed. “But in this case, most of the damage was actually done by Pinkie’s giant marshmallow plan. She wants any company doing an event at the school to have insurance now. It’s just a little paperwork, and they’ll send you a bill.”

“‘A little paperwork’?” Trixie asked incredulously, gesturing towards the quarter-inch of parchment stacked in front of her. “They want everything back to Trixie’s father’s qualifications with pyrotechnics!”

Starlight sighed, rolling off of her bed and walking up behind Trixie to give her a nuzzle.

“Come on, Trixie. Do you really want to disappoint all the little fillies and colts just because of some forms? The chance to perform on a full stage with curtains and everything, showing up Twilight Sparkle at the one thing you know you’re better than her at? Even a lot of paperwork never really hurt anypony.”

“Starlight,” Trixie deadpanned, “ there is a deed to one of Trixie’s kidneys in here for collateral purposes.”.

“But they’ll take it out with knives, not with the paperwork!” Starlight pointed out helpfully. “If you can finish your Great and Powerful paperwork, your lovely assistant can make it worth your while,” she crooned

“...Trixie’s listening.”

“Well, first, she’ll go and get her spare collar out and put it on,” Starlight explained. “Then, she’ll cuddle up behind you, and keep you company while you’re finishing the paperwork. The faster you get it done,” she said in her most sultry voice, “the better company she’ll be.”

“An - and if the Great and Powerful Trixie gets distracted by her assistant?” Trixie asked, swallowing to moisten her throat when the first word came out as a strangled squeak. Undoubtedly the consequence of her show earlier, merely a touch of laryngitis. Certainly nothing to do with the mare nuzzling and nibbling at her neck, up along her silvery mane, towards her sensitive ears.

“Then the lovely and skillful assistant puts her collar away and goes back to reading her psychology textbooks.” Starlight pouted next to one of Trixie’s ears. “And the Great and Powerful Trixie has to take care of herself tonight. But if she doesn’t get distracted, and finishes all of the forms?” Starlight stuck out the tip of her tongue, licking up the edge of that ear from bottom to tip. “She’ll get to show her naughty little assistant just how Great and Powerful she really is.”

“Get your collar, Assistant,” Trixie ordered, trying to keep her voice steady and failing miserably.

”Stupid, sexy Starlight Glimmer! Bad girl, taking advantage of her mistress like this! The Great and Powerful Trixie will not allow this impertinence to go unpunished!” Trixie promised herself.

Starlight opened up the second drawer in her nightstand, and magically worked the hidden mechanism that kept it from being pulled all the way out. Behind a false back, she had a bottle of lube, a couple of small toys, some condoms, and in a small wooden box, the collar she was retrieving.

She took it out of the box and held it up in her magic, smiling as she remembered when Trixie had stammered through asking her to wear her tags. They hung from the soft band of padded cloth, black lace with a red band down the middle. The first tag read ‘Property of’ and had Trixie’s cutie mark engraved on it. The second, rather more verbose, read ‘If found, please return to Trixie Lulamoon, gentle use permitted.’

She remembered the night she earned that tag. She couldn’t walk straight for a week afterwards, and had a silly grin every time she sat down for just as long, but it had been so worth it.

Fastening her collar around her throat, Starlight turned to cuddle up behind her Mistress, resting her muzzle on Trixie’s withers and nuzzling in comfortably. Just as she’d expected, Trixie was already filling out the forms, the first page already drying while she filled in the second.

“See mistress? You just needed the appropriate motivation,” Starlight murmured, wrapping her hooves around Trixie’s barrel, letting them rest gently just above the showmare’s teats. She started grooming Trixie’s withers, scratching at her neck and mane with her lips and teeth. Teasing nips and warm, affectionate licks saw the first five pages finished in fairly rapid order, Starlight using her magic to flash-dry the ink so that nothing would be smudged.

Starlight added her hooves to the mix now, gently kneading her Mistress’ teats and smiling at the suppressed moans she could feel in her lover’s throat.

“Will you make me be your little filly tonight, Mistress?” Starlight asked her. “Spank me for getting you all worked up, and then make me suckle at you like a foal, until you’re ready to make me suckle… lower?” She teased the tip of a hoof lower, just above Trixie’s heated, swollen mound.

“The Great and Powerful Trixie could do with a less aggressive distraction,” Trixie muttered back to her.

“All right,” Starlight pouted as more pages joined the pile of finished work. “Maybe Mistress would prefer to take her puppy out for a walk around the castle? Maybe even down to the throne room, show everypony around who’s really the Great and Powerful pony in charge?

“Maybe I’ll get loose again,” she whispered seductively. “Make you turn on the tracking charm on my collar, and find me before somepony down at the Society takes you up on my second tag? Or would you rather find me in the middle of it, and show what a wonderful Mistress you are by ordering me to stop right in the middle and come to you for my punishment?”

Ten pages done now, about half-way through. Fortunately for Trixie’s composure, she was reaching the point where most of the page was finely printed text laying out precisely what was (pyrotechnics displays) and wasn’t (accidentally pulling an Ursa Minor out of a hat) covered by the policy. She could simply skim through most of the page, searching for the spots to sign and brand her cutie mark, and just how much doing so would end up eating out of her profits from the show.

Not that there was much choice; if she didn’t, there wouldn’t be a show, so she could mostly just write and listen to her Assistant’s suggestions.

And come up with her own plan in the meantime, something special for her little minx.

Pages thirteen and fourteen were simply the detailed descriptions of exactly how badly Trixie would be ruined if anything did go wrong and the insurance company had to recover excess damages. The phrase ‘first born child’ caught her eye, but she quickly disregarded that concern. It was so much simpler to sign those away when childbirth would take a literal miracle!

Signature on fifteen, and on to the next - the stack of finished pages now dwarfed those yet to be completed, and Trixie could smell their mingled arousal heavy in the air around them. Just a little further….

“Or maybe you’ll just keep me here tonight, tied up as you practice your adults-only act?” Starlight continued. “Saw me in half and make me horn-fuck myself while you watch? Make me float above the bed suspended in a magical pleasure-field?

“Maybe just tie me to the bed and sit on my muzzle until I’ve made you scream yourself hoarse.” Starlight rubbed herself against Trixie’s dock, her own sex aching for attention.

This was the problem with teasing as an incentive. It meant they both had to wait until Trixie was done for any release. Not that Starlight couldn’t take care of herself… but her collar was a promise not to, to give her pleasure, cares, and safety to her Mistress. To let the Great and Powerful Trixie put on the show she wanted to.

It didn’t make ignoring her own aching loins any easier, of course, just gave her a reason to do so.

Eighteen, nineteen… there were only three pages left, and these all had so much blank space that it almost seemed a crime to have produced them. But, then, it would take space to provide the information of ponies who could tell them where to track down the showmare if it was necessary - or it would, if “Princess Twilight Sparkle” hadn’t (reluctantly) agreed to have her name added as a reference.

“I can’t wait for you to finish, o Great and Powerful Mistress,” Starlight crooned. “Your Assistant has missed your crop so badly, and been such a naughty filly….”

“And if she doesn’t wait for Trixie to finish the last page, she’s going to be on caravan-pulling duty until Trixie gets back from her next tour!” Trixie teased back. That shut Starlight up, and put a beautiful red blush on her cheeks.

A blush that Trixie couldn’t want to see matched by the one her flanks were about to acquire.

“Apply your brand as a witness, Assistant, and Trixie is done!”

Starlight’s cutie mark was burned into the parchment in a flash, and the last page turned over onto the finished pile. Starlight started to pull away to move to the bed, but Trixie whirled around to grab her and pull her nose-to-nose.

“Naughty Assistant, running away before your Mistress can kiss you,” Trixie said low in her throat. She leaned forward, pressing their lips together, the two mares sharing each other’s hot breath as they breathed deeply in and out. Trixie deepened the kiss, forcing her tongue into Starlight’s mouth despite a token resistance. Blue hooves wrapped around lavender body, and pulled the two mares together, just relishing in being in control of the contact after all the time being teased by her Assistant.

“On the bed, with your bell, and fasten your cuffs. The Great and Powerful Trixie has a very special trick in mind for tonight!”

“Ohh, I c-ow!” Starlight yelped as Trixie zapped her flank with a small lightning bolt.

“The Great and Powerful Trixie does not recall ‘talking’ amongst the commands she gave her Assistant!”

Starlight quickly fetched her cuffs from another concealed compartment, fastening one pair to her forelegs, and another to her hindlegs. She hopped up onto the bed, clipping the two sets of cuffs together with her chest against the bed, her ass up in the air, and her legs completing an obscene triangle while she fanned her scent towards Trixie with her tail.

Finally, a small crystal bell floated over in her magic, was tied around the end of her tail, and gave a single crystal-clear ring as she tested it.

“Very good, Assistant,” Trixie nearly purred as she picked out her tools for the evening from Starlight’s collection. She had her own in the caravan, but they weren’t quite what she wanted right now.

“What is the Great and Powerful Trixie’s Assistant’s record in the Perilous Pit Plunge?” Trixie asked smugly as she climbed onto the bed behind Starlight.

“Four minutes and thirty-seven seconds, Mistress,” Starlight answered obediently.

“Mmm… deep breaths, Assistant, panting is hardly befitting your position.”

Starlight closed her eyes, slowing her breathing. She had an idea what was coming, and so she focused on her breaths out, as well as in. The Plunge was Trixie’s version of her father’s signature trick, and Starlight had gotten remarkably good at holding her breath through it with her Mistress’ help.

Bad air out, good in… bad out, good in… bad out….

Starlight took a deep breath, filling her lungs with all the air that she could as she heard the faint ‘crack’ of a condom wrapping being torn open.. For an instant, Starlight smelled the pungent chemical aroma of latex and lubricant, and then felt the condom being pressed against her nose, stretching out around her muzzle at the insistence of Trixie’s magic. It rolled back along her face, the bottom rolling behind her chin and pulling up taut behind her jaw, the top stopping at the base of her horn as Trixie tucked Starlight’s mane up to keep it from rolling back down.

Starlight opened her eyes, looking at the world through a translucent layer of latex, and did her best to relax.

“Let’s see if we can make five minutes tonight, shall we?” Trixie grinned, climbing around her lover to stand over Starlight’s head. Trixie looked down, back between her legs, at her slowly suffocating sub’s face with a wicked grin.

“You have that long to make Trixie cum, Assistant. If you fail… well, Trixie may forget to remove your little learning tool!”

An empty threat, and they both knew it, but a possibility that still sent a shiver of dread and delight through Starlight’s body. The powerful wizard lifted her head, prodding Trixie's dripping sex with her horn, and carefully guided it in as Trixie sat down on top of her head.

The secret to pleasuring a mare with your horn, Starlight had long ago learned, was deciding if you wanted to use it like a cock, or a vibrator. In this position, of course, she couldn’t exactly thrust with it, leaving her with little choice but to resort to the second approach.

The problem with that, of course, was that her Mistress was damnably hard to pleasure like that from the inside.

And so, Starlight had learned a third technique, one that she was still refining.

Fortunately, she and Trixie both enjoyed their little practice sessions!

As the thin latex puffed in and out of Starlight’s nostrils, the unicorn began pulsing magic through her horn in a thick ring of telekinetic force. Trixie hummed pleasantly as the ring slid up into her sex, bounced lightly against her cervix, and began flowing back. Starlight’s horn was a buzzing spire of pleasure buried inside her Mistress’ wet warmth, sending pulses of pleasure deep into the showmare’s body.

Starlight’s lungs were starting to ache as she burned through her supply of oxygen. She fought to regulate her breathing, hoping that Trixie wasn’t losing track of the clock as she began writing shamelessly on top of Starlight’s head.

Trixie’s juices stained and matted Starlight’s mane as she felt the powerful pulses reflecting inside of her, passing through each other, a sense of having one cock sliding into her as another slid out. Her tongue lolled out, but she retained the focus to pick up Starlight’s crop, and struck one of her Assistant’s cutie marks firmly.

Starlight jolted at the sting of the crop, driving the base of her horn up against Trixie’s winking clit, but then she raised her flanks higher, a crude offering to the goddess of pain and pleasure that was tormenting her. Her lungs burned now, and she’d long ago stopped trying to hold her breath, but all that was there for her was her own increasingly stale breath trapped in the latex barrier around her head. Her chest heaved for air, stealing the dwindling oxygen inside with her, as her vision began to blur around the edges and darken. She could end this now. Just five shakes of the tail while she willed her bell to ring… even three, and Trixie would let her out. But even as her tail waved behind her, the bell remained silent, waiting for its wearer’s mental command to sound out. And Starlight wasn’t giving it.

It would be so much simpler, after all, if she just gave in. Stopped trying to control her magic, focused on the stinging pain in her loins, and just let the blackness take her. It felt so good right now; a peaceful, yawning abyss where she would only have to listen to the pounding of blood in her ears and her Mistress’ moans. It wasn’t even entirely dark in the waiting void; there were sparkles of light deep inside of it, tempting her even more to continue forward.

As Trixie’s stopwatch hit four minutes and forty-five seconds, and she felt Starlight’s magic beginning to flicker inside of her, she shifted the crop. She struck Starlight squarely on the winking pearl between her folds, as hard as she could. That got Starlight’s attention, and she screamed soundlessly as she came.

Starlight’s orgasm passed through her from tail to the tip of her horn, and her pleasure came out inside of Trixie as a flood of magical power, like having one of her fireworks explode inside of her. Trixie’s back arched as she let out her own cry of pleasure, this one anything but soundless. She dropped the crop, and ripped the latex barrier over Starlight’s face as she soaked the mare’s mane with her nectar.

Starlight, sensing air, took deep, heaving breaths as she fought to restore her senses. The dizzying, euphoric rush of nearly passing the point of no return left her entire body reeling drunkenly, a quivering puddle of pleasured pony.

Trixie pulled herself off of Starlight carefully, and slipped down to lay next to her Great and Powerful Assistant. A little telekinesis, and Starlight was free to lay down herself. It was like releasing the wizardess transformed her into a drunken cuddle-fiend, and she wrapped herself around Trixie without even caring about the band of the condom still around her face.

“You almost let me go that time,” she slurred happily.

“Never,” Trixie murmured, raining kisses on her lover’s face. “The Great and Powerful Trixie does not perform tricks that fail.”