Taming Rarity

You pay for your meals and give the customary tip.

You get up and step outside. Rarity follows you.

“I’m guessing not a lot stallions have gotten this far with you. You do know what usually happens when a stallion takes a mare to his home?”

She blushes. You guessed correctly. Her beauty was quite intimidating to most stallions. Luckily for you, you are not most stallions.

“Yes.”

“Good. What are you wearing under that dress?”

“Pardon?”

“Don’t play dumb. The way things are going I’ll find out soon enough.”

“Black panties.”

“Hand them over.”

She mumbles in confusion.

“You won’t be needing them anyway. Consider it a first installment on paying for my favor.”

Her horn glows. She pulls them down, steps out of them and hands them over. They feel damp on your hoof.

“It seems you’ve been enjoying my company.”

You pocket them.

A taxi passes. You hail it and it pulls over.

You approach the driver.

“Are you a good driver?”

“Yes, of course.” he grumbles.

One look at his face was enough to tell you that it had been a long work day for him and he wasn’t having any of your shenanigans.

You were going to give them anyway.

“So no distraction can get your attention off the road?”

“Yes!”

“And you drive slower during the night so you don’t have an accident?”

“YES!”

“Good, I tip drivers like that very well.”

You give Rarity a mischievous look.

“I do hope you’ll remain true to your word even if the lady shows me her appreciation of me with a blowjob.”

You get in the carriage. Rarity does the same.

“I did not agree to this!” she hisses in your ear.

“Yet. You’ll agree any second now. Am I wrong?”

She looks at you sheepishly.

You lean back in the seat. “Begin.”

After some hesitation she leans down and takes your cock in your mouth.

She starts sucking. You encourage her by running a hoof through her mane.

“Look me in the eyes.”

She obliges.

“Good girl”

She wasn’t great at this. She might throw out her feminine charms like confetti, but most gelded idiots that passed for stallions could barely get out a word in front of her, let alone get her to put out.

“Come on, you can go a bit deeper than that.” You put pressure on the back of her head to encourage her.

She puts up a valiant effort. Her eyes start to water and her makeup starts to run but it’s nothing close to a proper deepthroat.

You resume petting her head. Bless her little heart for trying.

“You do remember you have to move that pretty head of yours up and down?”

She starts bopping her head up again. Each time she goes down her eyes get a little wetter.

Trying to concentrate, she looks down.

You feign outrage: “Where are you manners, young lady? Ruining such a romantic moment by breaking eye contact.”

She looks back up at you. She had the expression of sad puppy. You reassuring stroke her hair. You weren’t planning on doing anything practical to help her plight though.

Although... She was having such a hard time on both suppressing her gag and moving her head. You could do the second one for her.

You grab her head and start moving it for her. Element of kindness, eat your heart out.

Of course now that she can focus on keeping her gagging in check, you can go a bit deeper each time.

You never fully plunge down her throat, but you always push your luck, just a bit.

"We're here."

Rarity gags in surprise.

You let go of her head. She bursts out coughing.

You step out and casually approach the driver.

You hand him his fare plus a "dealing with your bullshit fee".

"As promised."

You walk into your apartment complex. She follows.

"The elevator's broken again. We'll have to take the stairs."

You start climbing said stairs.

"Recovered from our little "misadventure" in the taxi?"

"Why, yes of course, darling."

Rarity wouldn't be Rarity if she didn't try and recover her class and composure.

"Good, because there's a lot of misadventures coming tonight."

You give her a mischievous look and she blushes again.

You wouldn't be you if you didn't sabotage her efforts to recover said class and composure.

"You have to admit, you don't need me to get that flank of yours into a misadventure."

"What do you mean?"

"Being unable to to pay for business supplies or a simple meal. Going crazy with power because of a book. Little things like that."

"Oh."

"I have something that might help with that."

"And what's that?"

"Don't be impatient, Rarity. You'll find out soon enough."

You arrive at your door. You pull out your keys and unlock it.

"Home sweet home."

"Well... this place could certainly use a feminine touch."

She wasn't wrong. Order was never your strong suit and you never really tried to self-improve on it like with other things.

"I agree. But that's a matter for another time. Take of that dress. I'll be right back with a little surprise."

You go to your closet and take your cane. Then you come back to her.

"What... what's that for?"

"It's your surprise. I kinda spoiled it a bit by telling you that'll be teaching you misadventurous flank a lesson."

"Well,... that's certainly unorthodox."

"Who could have guessed that the stallion that made you blow him in the taxi is unorthodox? Turn around and get your tail out of the way. You'll thank me after this."

"Are you sure?"

"Absolutely."

After a moment's hesitation, she does as you told her.

You start caning her. At the same time you start rubbing her slit with your hoof. You wanted her associate pain and pleasure.

She was already quite wet. After a few hits your conditioning started to work and she started to absolutely soak herself.

"You're enjoying this aren't you, Rarity?"

"Yes..." she pants.

"From now on you'll call me "Sir" each time you speak to me."

"Yes... Sir."

You resume whaling on her.

By the time her flank was a pleasing shade of red, you could here she was getting close to coming.

You stop rubbing her and drop your cane.

"No, you haven't even come close to earning that."

She squeaks in frustration.

You walk to your liquor cabinet and poor yourself a drink.

Rarity looks at you in confusion.

You sit down in the chair in front of her.

"Now, Rarity, you're going to give me a little show. You're going to play with yourself for my amusement. Whenever you get close to coming, you'll stop and wait until your slit calms down then start again. Understood?"

"...Yes."

"Yes, who?"

"Yes,... Sir."

"Good."

You sip your drink. It was a statement. You had no intention to get drunk. Luckily the same farmpony blood that kept you from pronouncing Prench words also gave you the ability to drink 5 Rarities under the table and still be sober enough to pull a carriage.

"Begin."

She awkwardly starts playing with herself as you stare at her.

The humiliating nature of the situation seems to get her even more exited.

"How long do I have to do this?"

"Until I'm satisfied with the show. By the puddle you're making, you seem to be enjoying "performing" for me."

Rarity blushed, but kept playing with herself.

By her moaning, you could tell she was getting close to coming again.

"Stop." you command her.

It took her all her willpower, but she does. She squeezes her hind legs together, desperate for further stimulation.

You sip your drink again.

You rub the edge of your glass with your hoof. Rarity looks at your hoof movement filled with jealousy and frustration.

The puddle under her was still growing.

"You can begin again."

Just as awkwardly as before, she starts masturbating once more.

You sip your drink again.

She swallows what little pride she still had and starts moving her hoof as fast as she possibly could.

All that meant was that when you ordered her to stop, it'd be even more frustrating.

And that said frustration would come sooner.

"Don't even dare to sneak an orgasm past me. Stop. Right. Now."

Clearly intimidated, she obliges. Out of frustration, she starts tapping her front hooves against the floor.

Again, she's squeezing her hind legs together.

"You've made quite a mess, young lady."

Yet again, she turns red.

You were barely older than her. You just liked to call her that.

"Lick it up."

"Lick... the dirty floor?"

"Yes. Consider it a part of your act."

After yet again hesitating , she slowly starts licking the puddle she made.

During the first lick, her eyes were filled with disgust.

During every lick after that, they were filled with shame instead.

"Make it shine."

It was an uphill battle for her. Her own body was betraying her. It was a race between her mouth and cunt to see if the former could clean faster than the latter could make a mess.

You sip your drink again.

"You're going to have to lick faster than that. You're dripping on one part of my floor as you're licking another part clean."

She took your advice to heart.

There's nothing left of the lady that walked into your office. Before you was an animal furiously licking up its own filth.

"Liking the taste of your own cunt, Rarity?" you say to her while stroking the edge of your glass again.

"Yes,... Sir."

She doesn't have the dignity to look up from the floor while answering.
"Good enough."

She looks up at you. Her face is covered with her juices.

"I'm guessing by this point you're begging for me to mount you and fuck one of your holes."

"Yes, Sir."

"Then beg."

"Please, Sir. Mount me and fuck one of my holes. Please!"

"Because you ask so nicely."

You finish your drink and get out of your chair.

You start circling around her.

"Hmm, which hole should I use?"

Rarity just stood there looking awkward. She was squeezing her legs again.

"Well, answer."

"My pussy, Sir?"

"Yeah, by the waterfall it has become I knew you'd answer that. But your ass sounds more fun."

"But I've never been fucked there... Sir"

"Good."

"It'll hurt."

"One good look at your red flank tells me that you won't mind that."

"It'll be dirty."

"Something tells me you don't mind doing dirty things for me. I'll be right back."

You walk to your closet again and take a ball gag.

You come back with it.

"What... what's that for, Sir?"

"We wouldn't want you waking the neighbors, would we?"

"No, Sir."

You hand it to her. She uses her magic magic to fasten it.

"Come with me."

She follows.

You point at a spot in front of a big mirror.

"Stand there so I can see your pretty face as I fuck you."

Who said you weren't romantic?

You mount her.

You started rubbing her slit and started pushing into her asshole.

Yet again, you wanted her to associate the things you were doing to her with sexual gratification.

Pavlov and his dogs in Stalliongrad had nothing on you.

Her eyes were watering again even though you only had the tip in.

She was so tight.

"Am I hurting you?" you say in a mocking tone.

She nods while giving you those same puppy eyes as in the taxi.

"Want me to stop?"

She shakes her head.

You start moving your cock like a battering ram.

Each time you rammed into her, you could get a little deeper.

Rarity was in heaven and hell simultaneously.

From the faces she was making, you'd swear that she was a cartoon character.

Poor girl will be walking funny for weeks the way things were going.

You weren't planning on relenting though.

With one final push you got yourself in all the way.

You could hear her moaning thought her gag.

She was about to come.

It had been a long night for her. You figured by now she earned an orgasm.

You stopped rubbing her slit though. If she was going to come, it was going to be from your cock only.

Not that that was a problem for her. 3 missed orgasms and your psychological tricks saw to that.

On the next stroke, she squirted, bit down on her gag and clenched her ass simultaneously.

While quite pleasant on your cock, there's now way that didn't hurt her like crazy.

Oh well, that's a win win if you ever heard one.

Most stallions would now have the common courtesy to just come in her and end her trials.

But you were only getting started.

You pick up the pace.

A few minutes later she was moaning again.

Her eyes were rolling back into their sockets.

Her last orgasm had left her extremely sensitive and paved the way for the next one to come in even easier.

When it did come you din't even slow down pounding her even as she clenched around you.

You were sure that a tiny part of her hated you for that and the extra pain it caused.

You were also sure that the rest of her will be grateful for that until her dying day.

You fell into a routine.

Time flew.

Once in a while, Rarity would come and clench up while you pounded her.

Neither of you bothered counting how many times she had done so after a while.

You just kept using her.

Eventually, you ran out of stamina.

You plunged your cock one last time into her and filled her with your seed.

Rarity showed her appreciation by coming one last time.

After your cock popped out and you unmounted her, she simply collapsed.

You undo her ballgag for her.

"Thanks,... Sir"