A Complicated Relationship

“Now that you’ve gotten some practice, I want to try this game out.”

Mistress Starfruit gestured to a row of dildos on the floor. She had them standing up in a line from smallest to largest. It didn’t take genius to figure out what she had planned, but that didn’t stop Final from feeling anxious, gazing at the frigthening Minotaur dildo at the end of the line. She knew her daughter would add some twisted complication to this torture. Even so, she had no choice but to play along, still restricted by a hobble and her waist harness keeping her hands at her sides. Thankfully, good behavior had gotten Final out of the chastity belt and upgraded back to the harness, which seemed to be her default apparel in the dungeon.

A frustrating addition to her outfit was the legbinders. Not a singular sleeve this time, but two separate sleeves on each leg, each keeping her calves pressed against her thighs in a pseudo frog-tie. Her only means of keeping balance was to either kneel down on her knees or stand on her hooves in an uncomfortable squatting position. She kept herself in the kneeling position prostrated before Mistress Starfruit.

The pegasus apparently wasn’t in the mood for any interruptions either; she had gone through the trouble of strapping a muzzle onto Final. The muzzle employed a specialized ring gag that certain attachments could be inserted into for kinky scenarios. Final was familiar with it, she recalled using a feather duster attachment on clients for maid fetish play. The current attachment lodged in her mouth was a double-ended dildo gag. Six inches in, nine out. It wasn’t too much of a burden for Final at this point; her gag reflex had mostly disappeared. Mostly. The biggest annoyance was the leverage of the rubber phallus sticking out of her face putting a mild weight on her neck.

“You’re gonna have a dildo race!” Starfruit exclaimed. “You have to go down to the base of every dildo within twenty minutes!”

Final felt her heart leap when she heard “twenty.” There were thirteen dildos lined up, which meant only slightly more than a minute for each. The smaller ones would be easy, the medium ones manageable, but the larger sized ones would take time. Her beating the time limit was wishful thinking. The unicorn sighed and resigned herself to her fate. She had already lost, but in a way it was somewhat relieving. At least now she could properly pace herself and not worry about failure. It was a forgone conclusion, so there was no uncertainty. She would play the game and just endure whatever torture her daughter concocted this time. Punishment had become so common for her that it ceased being a threat. Much to her dismay, she enjoyed it at times. Her mind was acclimating to her new stature, and pain had become less of a burden than when she started.

It was withholding pleasure that frightened her. She had spent enough time in the chastity belt and had only just gotten out. Mistress might put her back in again. Then it would be nothing but tease sessions while she was hooked up to the milker. Mistress wouldn’t fuck her, at least not the way she wanted. Mistress knew the proper ways to make her cum and delighted in denying them to her. Final dreaded the pain of going through this race, but if pain wasn’t a big issue anymore, wouldn’t it be worth it? Mistress was going to delight in her suffering no matter if she rebelled or not. At least if she submitted, she would get something out of it. Final weighed her options.

“Obviously, I’ll need to provide incentive.” Mistress gave a mischievous smile. “I was just gonna punish you for not making it in time, and I will, but I don’t think that’s good enough. A whipping is a little too… passé. I want this to be special.”

Final felt a sudden rush of panic. Was Mistress reading her mind? What could she possibly do worse than she already had?

“I was thinking about adding Mistress Aqua to our little entourage…”

“ullph?!” Final choked on her gag.

“…but it seems a little unfair to drag her into this without giving her a chance. The bordello can’t survive on slaves alone, it needs proper Mistresses like me or Ruby.”

Final squirmed a bit in her bindings and nearly fell over. She managed to correct herself and looked up to her daughter’s amused smile.

“Got your attention? Good. Because I graciously decided that you should be the one to make the call.” She gestured towards the line of dildos. “All you have to do is beat the time limit, and Mistress Aqua will get the chance to maintain her position. Fail, and…”

CRACK!

The whip struck the ground in front of Final. While there was no pain, the sound didn’t stop her from flinching. This time she did lose her balance and fell on her side.

“…you get a new playmate.”

Starfruit chuckled as Final tried to pick herself up. She took out what looked like a pink shampoo bottle and tossed it to the ground next to the unicorn.

“You’ll need that.”

Final looked at the bottle. It was labeled “ETS High-Grade Passion Fruit Lubricant.” She wasn’t sure what “ETS” was, but she was sure what would happen if she used it.

“I hoped this would make the game more fun for both of us.”

The sad part was she was right. Final had no chance of beating this game without lube, but she knew the passion fruit would drive her further into lust. She would be pushing herself willingly into the spiral that had already consumed Toy. She had already experienced the compelling arousal of passion fruit in the past, but something about the “High-Grade” on the label made her uneasy. And, unlike previous applications, she had a choice to not to participate this time. The image of Toy thrusting inside her flashed in her mind. She imagined Aqua in that position. Strapped down, fucked, and tormented in every way imaginable. There was a growing fear of Aqua being enslaved like that, as well as a growing arousal. Obviously, the passion fruit was responsible for that twinge of lust crossing her mind. It had to be. She couldn’t let another innocent pony be roped into this.

It took some maneuvering to properly pick up the bottle with her hands stuck to her sides, but she eventually held it in her right hand. Flipping open the cap, the sweet familiar smell wafted into her nose. She shivered. Even the smell had become enough to make her frisky.

Starfruit held up a stopwatch. “Clock starts as soon as you touch the first dildo.”

Final took a deep breath and waddled over to the first dildo as best as she could in the frog tie. She paused for a moment to ready herself before quickly grabbing the dildo and squirting an excessive amount of lube on it. The dildo itself was only four inches long; nothing she couldn’t handle. But the sizes would only get bigger from here. Her strategy was to use a liberal amount of lube for the starters as a way of getting a nice spread in her insides to help deal with the larger ones. If she was already gushing with lube by the time she reached the larger dildos, it would make the process a lot smoother. After being properly lubed up, she squatted herself down onto the rubber phallus. With no effort, it slipped inside of her until she hit the flared base, applying the first coat of lube to her anus. She then heard clapping.

“Very good, Pet! You didn’t even need a warning!”

Final was confused. She had apparently done something right, but what? She put the thought out of her mind and removed the dildo. The fake shaft slid out of her ass easily, and only then did she realize what had pleased Mistress so much. She wasn’t in the chastity belt anymore; her pussy was completely exposed. Instead of pleasuring her cunt she had instinctually went for her ass without any prompting from Mistress, who made a habit of tormenting her rear in nearly every session. Final had gotten so used to it that it had become her default form of seeking release. Worry creeped into her mind. She became aware of just how much Mistr—Starfruit had warped her psyche. She discarded the thoughts quickly; this wasn’t the time to get distracted.

She redoubled her efforts on the next dildo. Five inches long this time. With another application of lube, she shoved this one up her asshole with no issues. She was pot-committed to anal at this point. She had already spent a good amount of lube prepping her hole for this race. Swapping to pussy would be a bad idea for the late game.

The third was six inches long. In and out it went with no trouble. She had gotten into the rhythm of lubing up and squatting down. She was sure she was under two minutes, which was good. Speeding through the easy ones would give her more time for the largest set. She moved to the fourth without breaking stride. This one was also six inches long, but noticeably thicker this time. It still wasn’t a problem for her, but she could feel her ring stretch wider than previously. She gave a foreboding glance at the larger dildos before moving on.

The fifth dildo was eight inches and equally as thick as the previous. She noticed the increasing girth of the lineup from first sight, but now she felt it. The fifth was nine inches with the same thickness. This one went in smoothly as well, but it did elicit a small grunt through her cock gag. She had mistakenly thought her biggest issue was going to be girth. To her, the length wouldn’t be an issue once she got past the initial insertion. She only now realized that while her own anal ring had gotten quite a bit of stretching over the days, her insides hadn’t been pushed as far.

This was made more clear by the sixth dildo. Ten inches long and thicker. She had taken ten inches in previous sessions, but the diameter was more than expected: three inches. She had worn butt plugs of that size and bigger, but they never went that deep. Pulling out was becoming harder as well. With her legs bound as they were, she had to push herself off the dildo from her squatting position. But now, the length was too much to fully get it out. She laid her back on the floor, the phallus still stuck inside but poking out of her hole, and tried lifting her thighs up. Because the legbinders kept her hooves against the back of her thighs, her hooves were positioned on her ass, with just enough movement available to clamp her hooves around the dildo and pull. The legbinds didn’t allow her to push her hooves out far, so Final had to gradually work the dildo out fractions of an inch at a time. Eventually, her tactic was successful and the dildo plopped to the floor along with a trail of lube. Final was getting worried. She had only concerned herself with entry and only now realized how much time simply removing a dildo was taking.

Number seven was the same size, but thicker at three-and-a-half inches. She slid in decidedly slower, though still making good time. She noticed herself breathing a bit heavier. She repeated the arduous process of removing it and moved to the next. At the eighth, things slowed down further. Eleven inches long, three and a half wide. The phallus was too long to squat down on with her legs bound. She now had to start angling the dildos at forty-five degree angles and push her ass against the floor to slide it inside. This only further increased the time spent. She no longer had ideal positioning or gravity to assist her.

The ninth had increased the length by another inch. She was having a harder time angling this shaft even with her new forty-five degree strategy. The dildos weren’t completely rigid and still had a bit of floppiness to them. This did have a benefit of making them slightly easier slide in, it made pushing against them difficult from her position. This time, the dildo bent a little when she pushed against it, sliding across her ass cheek and flat onto the floor. Final, who had been pushing her weight against the dildo, lost her balance and fell backward onto the floor. She huffed in frustration while Mistress Starfruit laughed at her struggles. That screw-up cost her a lot of time. She got back up and shuffled her knees over to the dildo once more, applying a fresh coat of lube again. Angling it yet again, this time taking it slower to properly line it up, she managed to push the length steadily inside her.

Noticing that this new strategy wasn’t working, she went for something different. Number ten was another inch longer, putting it at thirteen. She grasped it in her hand, and then waddled over to one of the dungeon’s walls. She put the base of the dildo flush to the wall to provide something sturdier to push up against. She hoped that Mistress wouldn’t count this as cheating and punish her for it. Giving a glance over to Mistress, she seemed too amused at the unicorn’s agonizing to care. For all Final knew, the game was already over and Mistress was just toying with her again. She had no idea how much time had passed, but she was already too far to give up now. Sticking her ass up into the air with her face on the cold dungeon floor, she shimmied herself backwards onto the rubber shaft. There was no slippage, but it still took a good length of time to actually reach the base. What’s worse was that the shimmying movements made the travel less smooth. Instead of going in a straight line down her anus, it kept constantly poking up against her insides with each small push. Final was becoming thankful for the passion fruit distracting her from the discomfort.

Eleven set things back even further. Fourteen inches long with a three-and-three-quarter diameter. She kept to her same strategy, but her movements became even more sluggish. The size was already a problem, but endurance had now become a factor. Having to maneuver herself as she did throughout this ordeal combined with blitzing the ten previous dildos had taken a toll. The girth was becoming too much to handle, her O-ring gripping the rubber tight. The lube could only do so much. She reached the base and slowly removed herself. Each inch removed caused her insides to mildly collapse from the lost pressure, and she felt it. There was a small delay, that half-second sense of dread, before the pain hit that only added to the torment. There was no avoiding it. Moving faster only made it hurt worse.

There were tears in her eyes when she looked at number twelve. She wasn’t sure if the tears were already there or if they were in response to the size. Fifteen inches with a base of four inches. She could feel her heart pumping in her chest. Her brain was firing off warnings as she aligned the dildo against her O-ring. Her exhaustion worked to her advantage, as it dulled the fear. She was practically on autopilot at this point. However, she was roused from her stupor about one-fourth of the way down. The stretching had become too much and no amount of passion fruit was enough to override the pain. She found herself stuck, unable to move further. The rubber cock felt like it was pushing against her intestines, like it was somehow growing inside her. She imagined it expanding until it burst her entire body apart. It wasn’t possible, but the pressure made it feel that way.

The fear gave way to frustration. Not the frustration of losing the game, thoughts of Aqua’s freedom had slipped into the back of her mind, a frustration of the pain itself. A primal urge of spite to not let the pain defeat her. Her rage gave her the adrenaline rush she needed to push herself onto the cock with all her strength. She rapidly began moving back, thinking nothing of the burning pressure expanding her guts.

“HMMPH! HMMPH!”

Each shimmy down the length was accompanied by a large shout of indignation, as if she were taunting the inanimate phallus for challenging her. She hit the base quickly and departed it with a long growl of rage as she shuffled herself off. The frenzy wore off as the dildo popped out. Final quickly realized what a mistake she had made as the fury died down. She had successfully beaten number twelve, but the soreness in her rear became apparent. Her rushing that dildo didn’t give her body time to adjust to the size of the cock as it was being spread out. The sudden expansion had hurt her far more than if she had gone down gradually, and her anger had caused her body to tighten around the phallus instead of loosening. She collapsed to the floor in agony as her brain finally registered the pain.

One left. The Minotaur. Fifteen inches long with a four-and-a-half inch diameter. Final could barely see it. Her vision had become hazy, not just from tears. Her face lay sideways on the floor with her now gaping ass in the air. Drool slipped past her gag and pooled on the floor. She breathed erratically as her body failed to soothe the soreness that had spread deep inside her. She couldn’t focus on anything. Her neurons were on fire and she had to shut her eyes hoping that cutting off her vision would ease the overstimulation. All it did was make the aching more conspicuous. She opened her eyes. She had long since forgotten why she was even doing this. She knew she had to reach the base of The Minotaur, but why? She heard giggling. She looked towards the source and saw Mistress. Mistress seemed entertained. That must be why. She was keeping Mistress happy. If she gave up, Mistress wouldn’t be happy. A twinge of some unknown feeling cut through the throbbing ache in her mind. She couldn’t let that happen.

The unicorn slave instinctually reached for the dildo and placed it against the wall. It slipped past her cheeks and pressed up against her O-ring. The gape was stretched wider as she pressed herself onto the cock. It was barely an inch in before Final had to stop. It hurt. It hurt a lot. The pain burrowed into her head and her body convulsed. The convulsions reminded her of something. Her body had done this before.

Mistress had caused her pain before. Her body had been in this unbearable situation more times than she could remember. Like when Mistress would strike her with the whip. That was good pain. If she imagined it was Mistress causing the pain, she felt she could tolerate it, maybe even enjoy it. And, after all, wasn’t Mistress causing the pain? This pain throughout her body belonged to Mistress. The phallus was Mistress. Mistress wanted to be inside of her. To be close to her. Mistress wanted her body. She needed to get closer to Mistress. Her guts widened as the phallus pushed its way through. She could feel the friction of the rubber grating against her bowels. It hurt, but each sting of pain reminded her of Mistress. This was Mistress’ touch. Each inch brought her closer to Mistress. She gave a guttural moan as she slid further down. The moan wasn’t of pleasure or pain, but longing. A desire to get closer.

“Fantastic! Absolutely fantastic!”

Final heard clapping. Mistress was complimenting her. The unicorn wasn’t sure why. Her mind was taking a long time to process anything that was happening. She suddenly became aware of a smooth surface pressing against her butt cheeks. She had reached the base.

“Twenty seconds to spare!” Mistress Starfruit gleamed. “What an absolute champion!”

Final pondered over what was meant by “twenty seconds” before remembering that she was being timed. This was a contest for something. She tried to remember for what but her body crumpled to the floor before she could recall what the reward was supposed to be. She lay on her side before tipping over onto her back, The Minotaur still lodged up to the hilt.

Mistress walked towards her slave and stood over the unicorn. Final’s eyes were glazed over. Mistress’ glistening exposed pussy was directly above her face. She caught Mistress saying something in her peripheral vision, but didn’t hear it. Her owner’s wetness became her focus. It came closer to her as Mistress crouched down and aligned herself with the cock gag on her slave’s face. Final wasted no time thrusting her head in and out while Mistress bounced on her face. The pain in her rear was gone. There was no thought left, only an instinctual drive to service her owner. She moved with her Mistress, a perverted dance guided by the pegasus. Final savored the moans, the scent, and the arousal that dripped onto her face. This was her reward.