Octavian Coltcapades

by Shadowflash

Rating: mature
Tags: Sex, My Little Pony: Friendship is Magic, Dark, Original Character, Octavia
Length: 8512

Octavia is invited to the Fancypants estate in which she is offered to purchase her very own colt sex slave. Side fic to another story I'll release later.

Octavia is an... Adventurous mare, to say the least. Sure, she's a talented musician and plays in Equestria's best orchestra, but she's different compared to other ponies.
Having received a letter from Fancypants, Octavia travels to his private estate while blindfolded to examine, to test, and to purchase her very own colt sex slave. Most ponies would say this is wrong. But, what they don't know won't hurt them. Besides, these kids ain't cheap.

Trigger Warning: F/M Foalcon, Toys, Abuse, Etc (Whatever else gets tossed in, I guess)

A fiction for my dear sexy friend: TittySparkles.

This is a side-story (which pertains to mostly sex) that is going to be linked to another story I'll release later. Just a simple one-shot.

Published 2013-09-26 19:50:01 UTC
Last updated 2013-09-26 19:50:01 UTC

Product Purchase and Testing

Octavian Coltcapades
Product Purchase and Testing

Edited by:
ArmedBrony
the parasprite
Narlepoax III

Pre-read by:
TittySparkles
Skeeter The Lurker

Dear Octavia Philharmonica,

We have heard about your request to visit the Fancypants estate to discuss business. As you are probably well aware, this isn't an easy process. Many scans on your profile have been made to ensure you are not of higher authority, and you were watched by our agents for many months to confirm the information.

But, since your check has cleared, Fancypants would like to formally welcome you to the Fancypants estate. All business which includes any and all activities that is conducted at the estate will be kept one-hundred percent confidential and off-record. Further information will be given to you by Fancypants himself once you arrive.

Our drivers will pick you up tomorrow at 7AM sharp. If you happen to miss it, they will come back an hour later. There is no other opportunity once you miss the second pick-up. You will also be blindfolded on your way to the estate to ensure the location is kept one-hundred percent private (this is standard procedure, as given in the guidelines sent with this letter).

It's just business,

~F.D.L

Octavia set the letter down, and looked over at the clock. "6:53AM..." Deciding not to waste any more time, Octavia trotted out of her househaving been in the foyer, waiting for a knockto greet the "drivers", when they arrived. The air was as cool as a spring breeze, the dew still settling on the grass, and the sun slowly pushing past the horizon. Not a cloud filled the air, marking this a beautiful day for Octavia.

Clipclop-clipclop-clipclop

She took in a large breath of the outside air, looking over in the direction of the fast clopping of hooves. A large cart with two even larger stallions was coming down the empty cobblestone street, slowing down as it neared her.

"Well, this is it," Octavia told herself, "I am going to be able to indulge my guilty pleasures. Finally."

The cart came to a slow halt in front of Octavia's home. She trotted forward as the stallions huffed violently, catching their breath. The cart was a white "stretch cart" that was meant for the Nobles or for very wealthy ponies. Octavia took a few steps towards the cart, only to be stopped as the door opened and a gray stallion stepped out.

He was decently large for a stallion, despite being a pegasus. He wore large aviators, a tuxedo, and a black beretthe common attire for hired security. He smiled as he held a hoof out to Octaviawhich she shook.

"Hello, Miss Philharmonica. I am Armoured Vestyour security escort for today." His voice was rough, but it was filled with a cheery tone. As if he woke up on the "good side of the pillow."

"It is a pleasure to meet you, Mister Vest," Octavia greeted in return.

"I am sure you read over the guidelines and understand that you are required to wear a blindfold, correct?" Vest asked, raising his brow.

"Of course. I am also to assume that you would like to see my invitation?" Octavia handed over the letter to the stallion.

"You are correct," Vest took the letter and skimmed it quickly before smiling, "Alright, everything is in order. Let me just put this blindfold on and we should arrive safely in about three hours."

"Three hours? Wher" Octavia stopped herself, shaking her head, "I understand. I could use some more sleep, anyways."

"That's what most customers do. I'm also going to be making a stop for another customer. He's not too far away, which is why we're picking him up. I hope you're okay with that."

"Of course. It is your job, after all."

Vest lead Octavia into the cart, which was much roomier than it looked from the outside. Most of the inside was comprised of small beds and very few seats. Octavia smiled as she sat down on a bed.

"If you get uncomfortable, let me know. I know it's procedure to have it tight as possible, but, we don't need our customers in pain," Vest chuckled as he pulled out a blindfold and wrapped it around her head. He tied it tightly, to ensure that it wouldn't fall off.

"Anyways, enjoy the nap. If you fall asleep early, you might be able to sleep through the bumpy roads," Vest closed the cart door before he whistled to the drivers in front.

Octavia heard the loud sound of huffing before the cart began to speed up and gently vibrate. She quickly felt around the bed and found herself a pillow, collapsing on her side and sighing contently.

I'll have my own little colt soon... A colt that will call me 'Mistress'... To please me in every way... Octavia thought, smiling softly.

Maybe on the ride back, I can have my way with him; whoever it may be. Octavia felt a small shiver run up her spine before she let herself fall asleep.

Octavia awoke to the feeling of something shaking her. She opened her eyes slowly to see the blindfold was off, and Vest was looking at her with a small smile. She slowly sat up, rubbing her eyes and yawning.

"We're here, Miss Philharmonica," Vest spoke softly, as he opened the door to the cart for her.

Octavia slowly stood on her hooves and moved out of the cart. As she did, she was greeted by a massive house, four or five stories high, that was composed of a mostly mossy brick structure. Although it looked old and crumbling, it seemed to be supported by massive pillars surrounding it.

Vest gently nudged Octavia, causing her to look over, "Right this way, Miss Philharmonica."

Vest began walking towards the large doors of the building, and she followed suit. As they neared, the doors opened to reveal a luxurious interiormarble floors, velvet carpets, crystal chandeliers, the works. It was beyond "fancy" for Fancypants, but it clearly showed money wasn't an issue to him.

"Head on inside. Fancypants will greet you soon." Vest gestured for Octavia to go inside.

Octavia nodded and trotted in. The doors closed behind her, leaving the echoing sound of the door's creak filling her ears.

It is dreadfully quiet in here... Octavia thought, looking at the spiral staircase leading up to the next floor. I thought this place hosted more people, but... I guess not.

Octavia's eyes scanned around the large foyer, looking over minute details such as the oak cabinets that line the walls, or the large pictures of Equestrian landscape. Anything to keep her occupied while she waits.

Is he even here...? Octavia sighed impatiently, as a few minutes passed by, I mean, if he invited me, you would think he would at least show up early.

"Ah, Octavia!"

Octavia's ears perked up to a delightful Englishpony's voice, which echoed in the foyer. She turned to her left to see Fancypants in his iconic suit and sporting his blue tinted monocle.

"It is such a pleasure to see you, Octavia. I'm glad you didn't chicken out," Fancypants chuckled as he trotted towards Octavia, quickly shaking her hoof.

"Well, it took a few hours of thought, but... I believe it is time to give into what I have wanted to enjoy for a long time." Octavia smiled faintly.

"Ah, yes. A newbie to this whole thing. Well, do not worry, my dear mare, I'll make sure you feel comfortable," Fancypants said quickly, "I am sure you are wondering where everypony is, though."

Octavia shook her head. "Yes. It is rather... Quiet."

Fancypants smiled, "Come, my dear."

Fancypants trotted towards the spiral staircase, quickly climbing up it. Octavia followed shortly after, trotting up the stairs with Fancypants. As they ascended, the sound of music and talking ponies began to fill Octavia's ears. Each step, the sound increased, until they reached the top, where an iron door sat. Fancypants withdrew a key, unlocking it and opening it for Octavia.

Octavia trotted inside to see a mass assortment of ponies, griffons, zebras and even diamond dogs. All together on the second floor of the house. The room was a bit smaller than the foyer below, however it comprised of mostly an open floor. Many buffet tables edged around the sides, boasting exquisite food on their surfaces. A large stage sat at the far end of the room, from which the music echoed. The music was classical and loud, but was soothing to Octavia's ears.

"Welcome, Octavia!" Fancypants trotted next to her, making her jump a little, "This is our wonderful little society, which I keep secret. Many different species come here just to get a taste at their inner demons."

"It is... Unexpected. I thought it would be just a few ponies... But this?" Octavia smiled, "It makes me feel more comfortable, knowing that I am not the only one."

"Ha! That is the spirit, my dear friend. Now, come. Let me show you my 'wares' and then we can discuss business," Fancypants, once again, trotted off without warning, leaving Octavia to slowly catch up.

Thankfully, he didn't walk into the dense crowd in the center of the room. Instead, Fancypants went off towards a large oak door labelled "Customers Only." He pushed it open for Octavia once more and Octavia entered. It was a long dusty and dark hallway, but Fancypants took the lead, using his horn to illuminate the hallway.

"Now, I know this looks shady, Octavia, but it is for a reason," Fancypants said as he trotted down the hallway.

"And what is that reason?" Octavia asked.

"Do you know what 'breaking' means?" Fancypants retorted.

"As in what? Psychological or physical?" Octavia asked.

"Psychological," Fancypants answered.

"Well, it would be something related to stress, I would have to say," Octavia tried her best to respond.

Fancypants chuckled. "Not quite. You see, fillies and colts are very weak minded. Scared easily. Cry a lot. A lot of them tend to be scared of the dark. So, we introduce them to the most psychologically breaking factors.

"Things like fears, mostly. We do this to ensure they are constantly under psychological stress, wanting to get out but completely helpless. Their cries mean nothing," Fancypants held a smile on his face now, "And once they finally give into their fears, they become easy to hypnotize. We hypnotize them, to perform sexual acts and then we sell them. But, as a precaution, we keep them in the dark."

"Do any of them ever see light?" Octavia asked, taking in every word he said.

"Of course!" Fancypants grinned, "We promise them that, if they listen and do a good job, they may move on to the next level. Which is basically being able to be chained outside in the main hall. None of them are out of display right now, though."

"I see. What about the ones that cannot be hypnotized?"

"Well, we've never had a problem with it. But, if that did occur, then we would take them to the torture block. Physical pain will break them faster, but I find the process leaves the product too marred. So, it is a last resort only."

Fancypants and Octavia had finally reached the end of the long hallway, in which another large iron door sat. Fancypants opened it and trotted in before Octavia this time, Octavia then joining him. His horn flared brightly and illuminated the room to reveal two cages with fillies sitting in one and colts in the other.

"Wake up children!" Fancypants clopped his hooves together, smiling.

A lot of quiet yawns were heard as the army of foals woke up from their slumber. Fancypants turned to Octavia, directing a hoof towards her.

"This is a new customer. She wishes to purchase one of you, and that means you will be able to leave here, if she picks you," Fancypants looked over foals, all of them staring at Octavia. "So, whoever she picks, it will be your lucky day!"

"Yes, Master," All of the foals responded, in robotic unison.

"So, Octavia!" Fancypants clopped his hooves together excitedly. "Which gender do you prefer? Male or female?"

"I would like a colt, please," Octavia responded, excitement building up inside her.

The group of fillies in the cages separated and moved to the back of the cage, while the groups of colts moved to the front. Octavia looked over the line of colts, all of them wearing collars that had names imprinted on them. Octavia smirked gently as her body quivered with excitement.

"I-I... I am so unsure on which one I should choose..." Octavia sighed, "I would take them all if I could..."

"Well, how about you pick the best three, hm? Makes it plenty easier for the customers," Fancypants suggested.

Octavia nodded, looking back at the colts. Many of them stood emotionless and nervous, some shaking and others standing tall and composed. She let her eyes fall on one of them who was standing tall. His coat was white, decorated with brown spots, along with his mane, tail, and eyes being a deep shade of brown. His name tag read "Pipsqueak."

Letting her eyes move to another colt, they landed on a shaking one. His coat was an off-white colour and his body was thin in physique, as if he was starved. His mane and tail was a lighter shade of brown, like Pipsqueaks, and his eyes were a matching brown, as well. His name tag read "Featherweight."

Finally, Octavia's eyes fell on another skinny colt, only he held a nervous expressionas if he was worried about something or he wouldn't be picked. His coat was brown and his mane and tail were a mix between light brown and orange; orange being streaked throughout it. His amber eyes followed Octavia's, his pupils like saucers staring at her. His name tag read "Button Mash."

"I wish to only look at Pipsqueak... Featherweight and... Button Mash, please," Octavia asked politely, watching as the colts backed away.

Button Mash began backing away too, which caused Octavia to raise a brow.

"Button Mash, are you defying an order?" Fancypants chided in quickly, causing Button to stop in his tracks.

"N-no, Fancymaster I-I mean Masterpants I mean Master!" Button struggled to spew the words out of his mouth as he trotted quickly back in line with Pipsqueak and Featherweight.

"You seem to be out of practice, Button. I think that deserves some... Reassessment, would you not agree?" Fancypants smirked as his eyes looked over Button.

"Y-yes, Master," Button stuttered, agreeing with him.

"Good. Now then, dear Octavia, make your choice," Fancypants said, silently watching the three colts.

Octavia looked them over once more. Thoughts raced through her head on which one she should pick. I am so unsure... They are all good, but I can only afford one.

Perhaps I should get the pros and cons of each... Octavia sat on her rump, thinking intently on listing. Pipsqueak seems to know what he is doing. He holds a strong posture but he is a bit plump in shape compared to Featherweight and Button Mash.

Featherweight seems to shake too much, probably because he doesn't hold the same muscle or fat like Button and Pipsqueak has. He also has ugly overbite... But he seems easy to abuse.

Button seems really nervous... Clearly has trouble accepting orders and he does not want to be taken away by me, that is for sure... Hmm.

"How are their... Abilities?" Octavia inquired.

"Ah, good, I thought you would never ask," Fancypants smiled. "Pipsqueak is very experienced. He has pleased many mares during his time here and they have all told me that he brings them great satisfaction. The only reason he is still here is because he acts... Bratty.

"Featherweight is also very experienced. He listens better, compared to Pipsqueak, but he takes a long time to actually... Make you climax. The climax is good, but some mares wish to have a quickie with a colt. They do not wish to spend two hours with them.

"As for Button... He is new. We just brought him here two weeks ago. He has yet to please anypony and, as you saw, he has trouble listening to us. But, I am sure he will learn in time."

Octavia looked at the three colts, her eyes falling upon Button Mash. Octavia started to open her mouth, but Fancypants interrupted.

"I would suggest going with Pipsqueak. He is fine product, and it would make many mares jealous that you purchased him. Or Featherweight, if you enjoy a long session. But"

"I wish to have Button Mash," Octavia interrupted.

Fancypants raised a brow and quickly adjusted his monocle. "Are you sure? He is very fresh. He is practically useless right now, and would have trouble ple"

"I wish to have him. He is fresh. A virgin. Yet to please anypony. I want him to please me first, and only me. I want to teach him how to listen and how to be a proper slave to me," Octavia interrupted again. "I want him. I do not care what the cost may be."

Fancypants stared at her for a moment before smiling and giving a small nod. "Of course. I understand now. Fresh fruit from the plantation, hm? Well, let us pull him out then, eh?"

As Fancypants finished his sentence, a small door in the cage opened and Fancypants’ magic lifted Button out of the cage, setting him in front of Octavia. The yellow aura surrounded his collar as a small leash levitated to the colt and attached to it.

"Come, Octavia, we have business to discuss," Fancypants said as he trotted in front of her, the leash tugging Button behind him.

Octavia followed as her eyes fell onto Button, staring at his blank flank. Does not even know his talent yet... Even better.

Not much talking went on as the three made their way to a small office. It was mostly Octavia silently watching the new colt she was about to purchase. As they entered the office, Fancypants placed Button on top of a large oak table that sat in the center of the room. As he did, he took a seat in a padded chair, gesturing for Octavia to join him.

"So, as I said, Button Mash is a new colt here, and since he is fresh and untrained, I can give you a bit of a deal to take him off our hooves." Fancypants smiled, looking quickly at Button and then back to Octavia.

"So, what is the average price of a colt for customers?" Octavia asked.

"For a regular customer, it is usually one-hundred thousand bits. For a new customer, they get fifty percent off to, perhaps, ensure future deals," Fancypants explained. "This is also assuming the colt is trained."

"So, fifty thousand bits for Button Mash?" Octavia raised a brow, a tad nervous at the cost. That will put a massive dent in my account...

"No. Untrained colts are worth less. So, for you, Button is roughly twenty-thousand bits."

Phew... "Roughly?" Octavia inquired.

"I have to do the math to ensure the exact price. I do have ponies to pay before I pay myself," Fancypants explained.

"Ah, I understand. What are the payment methods? I don't really carry around twenty-thousand bits..." Octavia giggled softly.

Fancypants returned a chuckle of his own, "Of course. We take the money directly from your bank account, via signed bank forms." A small smile crept onto his face, "If the form is denied, we will have to... escort you to the bank, and make you withdraw the amount yourself."

"Well, I definitely know I have a lot of money saved up. The forms should go through," Octavia said coolly.

"Perfect. Let me just get the forms then, you’ll read them over, and then we can let you take Button Mash to the testing room," Fancypants stood up from his chair and went to an assortment of cabinets, opening them and rummaging through them.

"Testing room?" Octavia asked.

"It is where customers get to test their newly purchased product, or if members of this place wish to rent them," Fancypants' voice was muffled as he searched for the forms, "Oh dear, I need to organize this place, I am deeply sorry."

"I am in no rush... Well, not yet at least," Octavia giggled.

Silence fell on the roombesides the sound of boxes sliding or papers being rummaged throughand Octavia's eyes landed on Button Mash. Button was looking at her with a hopeful expression on his face: as if he was hoping for Octavia to let him go. Octavia couldn't help but laugh internally at this.

I hope you know you are mine, Button. You will do as I ask until the day I die... Octavia smiled as she stared longingly at the colt, making a frown creep onto his face.

Octavia stretched out a hoof and gently grabbed his leash, pulling him closer. He obliged and stared at her, not saying a word. She looked down at his little hooves, staring at the dirt that had begun to accumulate from his time in the cell. She looked back at him.

"It appears you may need a bath, Button." Octavia smiled.

Button didn't say a word, but only nodded. Octavia kept his hoof within hers, stroking it gently with her opposite hoof. She felt him shiver with nervousness and watched as he cringed, wanting to pull away and just run away from the room. But, she could tell that he knew the worst would happen to him if he tried.

"Ah-ha! Here they are!" Fancypants pulled out a small booklet of papers and a pen from the cabinet, turning back to the two, "After this, I am going to get my wife to organize this all. Maybe little labelsoh, I see you're getting friendly!"

"S-sorry. I am just... Excited," Octavia let go of his hoof, turning her attention back to Fancypants.

"It is quite alright, my dear. Feeling the product a little is natural," Fancypants assured her. "Now then, I'll let you read this over, at your own pace of course. You’ll sign, and then the deal will be finished. I'll send my men to your house when the transaction has been confirmed with the bank, or if any problems occur."

"How will this go over with the bank? In terms of them not suspecting an unusual purchase?" Octavia questioned.

"Simple. The form says you're spending the money on some of my farmland. I may be in the clothes industry, but, I've invested into a few farms for business. You won't actually own it, but it makes it look like you're investing in my business." Fancypants smiled as he pulled out a calculator, tapping in a few numbers before writing it down on the forms.

"Will they not check if you are giving me money for that land?" Octavia asked, curious in this endeavor.

"No, they will not. I have a personal relationship with the owner of the Equestrian Banks and I have ensured this issue is not looked into," Fancypants frowned for a moment before returning his smile. "The price is twenty-one thousand bits. So, just sign where the form indicates and then I will show you to the testing room."

Fancypants turned the forms to Octavia, levitating a pen and inkwell to her. Octavia slowly read over the text, spending about ten minutes to make sure she wasn't getting swindled. When she reached the end where Fancypants' signature and the twenty-one thousand ‘transfer amount’ was, along with the reason, Octavia contentedly went through and signed the areas that required her initials or signature.

After she finished, she slid it back to Fancypants, who quickly went through it and gave a quick nod to her. "Perfect! Now, take Button and I'll show you to the testing room!"

"Right this way, my dea"

"Oof! Hey, watch it bud"

"Thunderlane?" Octavia raised a brow as she stared at Thunderlane, the pony Fancypants just collided into.

"Octavia?" Thunderlane shook his head in disbelief, staring at the mare.

"Thunderl Oh, Thunderlane! I am terribly sorry, chap! Didn’t mean to bump into you. How goes it? Columbine doing well?" Fancypants asked, apologizing to Thunderlane.

"She's great, Fancypants. She's right here, actually," Thunderlane stepped out of the way to reveal a small, olive green, filly with a purple and white mane and tail. Her mane looked like a bedraggled flower.

"Ah, good to see she is doing well. Are you enjoying Master Thunderlane, Columbine?" Fancypants leaned down, smiling at Columbine.

Columbine looked up to Thunderlane, who nodded to her. "I love Master and how he treats me... I feel safe around him and I don’t want to leave him."

"Good to hear! Now then, Octavia, you know Thunderlane?" Fancypants turned his attention back to Octavia, who nodded.

"Yes. We were... Dating for a while. Had to stop, because of job complications. I still contact him every now and then to wish him happy birthday and such," Octavia explained. "I did not expect you to be a..."

"Pedophile?" Thunderlane asked.

"Yes..." Octavia blushed slightly.

"Well, I’d have to say the same thing to you. Is that the little colt you're buying right now?" Thunderlane pointed his hoof at Button Mash, who was busy staring at Columbine.

"Yes, it is. I just bought him, actually," Octavia answered excitedly.

"Ah, so you're going to"

"M-Master..." Columbine interrupted. "I know that colt."

Fancypants raised a brow, expecting a punishment to happen to Columbine for breaking one of the basic rules. However, Thunderlane smiled and looked to Button Mash.

"Do you, now?" Thunderlane smirked. "Well, Octavia, since I haven't seen you in a while, perhaps we could get together and have a little... Fun with our kids, hm?"

"Are you suggesting a date?" Octavia asked, giggling.

"For old times' sake," Thunderlane chuckled.

"Sure. I'll contact you tomorrow," She agreed.

"Oh, speaking of which," Fancypants intruded. "Thunderlane, what is it you are here for? No problems, I hope?"

"I have a few questions concerning Columbine. Mind if we talk in private?" Thunderlane asked.

"Of course! Meet me by my office. I am just going to direct Octavia to the testing room, and then I will meet you there." Fancypants smiled.

"Sure thing," Thunderlane began walking off, Columbine in tow, "Good seeing you, Octavia. Enjoy your time in the testing room!"

"A delightful young stallion. Perfect choice on your part, Octavia," Fancypants complimented, "Now then, right this way, dear!"

Octavia shook her head in slight embarrassment but continued to follow Fancypants. They reached a door, by which two large stallions stood guard. Fancypants smiled at the two, before turning back to Octavia.

"This is the testing room. Outfitted for your pleasure! Well, outfitted for everypony's pleasure, but you get the idea," he laughed, gently smacking one of the stallions' chests. "These two here will ensure your purchase will not escape. They are trained to keep their mouths shut, and to protect customers and their product. Last thing we need is someone stealing your purchase, hmm?"

Octavia nodded, "I am glad you have thought of everything, Fancypants."

"Ah, the joys of being smart come in handy sometimes," Fancypants chuckled, "But, I digress. I need to tend to Thunderlane. I will let you enjoy yourself in there."

Fancypants quickly trotted off and one of the large stallions opened the door for her. She directed for Button to trot in first, which he did, and she followed. Octavia closed the door behind her as she entered the room. She slowly looked around to see a mass assortment of different sex toys and machines; they ranged from a simple dildo all the way up to studded chains which hung from the ceiling. Octavia's heart raced as she began to imagine the many different things she could do to Button.

I need to keep it simple, though, she told herself, looking down at Button who was staring in shock, at the different objects around the room.

Octavia grinned, and picked the colt up. She brought him over to the large bed that sat at her left, and set him down. He stared at her with worried eyeshis body shivered slightly. In either fear or hopes of getting out of this place. Octavia smiled at him, gently bring a hoof under his chin.

"Now, since we are alone, my dear Button Mash, let us make a few things clear..." Octavia began, Button's ears perking up. "You are my property. I have purchased you for my use and you will never leave my ownership until I die. Any thoughts of escape will be met with... Consequences."

Button gulped, making Octavia smirk, and she continued. "You will always refer to me as 'Mistress.' I am not your mother, I am not your sister, I am not your friend. I am your 'Mistress'. Your job is to do whatever I please. You will never speak, unless spoken to. If I hear even a sound exit your throat, I will punish you severely. Understand?"

Button nodded. "Y-yes, Mistress... I-I understand."

Octavia leaned forward, letting her hot breath hit his little muzzle. Button tried to rear back, but she held him in place. A smile crossed her face, as Button cringed, awaiting a blow. Octavia then pulled back, removing her hoof, and smiling proudly.

"Good. Lastly, you will do as I say and whenever I say. Any time you disobey my orders, I will punish you severely." Octavia finished her small list of rules before looking away and gazing over the massive assortment of toys the room hosted.

"Now, what shall I use on you...?" She asked herself, walking away from Button to pick out toys.

For the next few minutes, Octavia gathered a small assortment of toys: a ten inch strap-on with a jar of lubricant, a vibrating butt-plug with a wireless remote control, and some leg braces to keep Button's legs spread. One-by-one, she placed them on the bed before Button, watching as he stared in shock at the devicesmainly the strap-on and vibrator.

This excited Octavia further, but she knew she needed to take this slow. I need to enjoy this. The first time needs to be good. Afterwards, I can rut him silly whenever I wish. She told herself, standing in front of Button again.

Octavia didn't say a word as she turned Button around and began to spread his legs. She felt the resistance from him, but it was weak and insignificant to her adult strength. She grabbed the leg braces and attached them to Button's hindlegs, preventing him from closing them.

Slowly, she placed her large hooves on his flanks, gently rubbing them in attempts to excite the colt. She heard Button hold back a scared gasp, but she shrugged it off, not wanting to punish him this early. Instead, she continued to rub his little flanks, watching as his testicles gently bounced with the movements.

I wonder what he smells like...? Octavia smiled as she stared at his flaccid member and his small testicles.

Since she was getting no response from his member, she leaned forward and pressed her muzzle into his testicles, taking a long and exaggerated sniff. She heard a much more audible gasp escape Button's lips, but she shrugged it off yet again, and began to tease the colt by giving his testicles a lick.

A salty taste entered her mouth as she did, which caused Octavia to shiver with more excitement. He definitely has not bathed. I can taste and smell the sweat from his crotch... Mrmm...

Pulling away, she removed the braces from Button's legs and set them off to the side. She climbed onto the bed, laying on her back, and presented herself to Button. She watched as Button's face went red and he attempted not to stare. His eyes quickly darting down and then back up at her.

"It is quite alright to stare, my dear... You will be seeing me like this quite a lot, and being nervous will not help any," Octavia smiled, staring at him as he let his eyes drop to her marehood.

Button looked intently at her vagina, studying every little detail, and trying to deduce what its purpose was. He vaguely assumed it was for bathroom duties and that looking at it was a bad thing, but it wasn't like his penis in any way. His childish mind filled with odd thoughts, as Octavia gently spread it before him, causing him to see an opening of some sort. He looked away, too unsure to even continue.

Good colt... She smiled, grabbing the strap-on and sliding it to him.

"I wish for you to lick this. Put on a show for me..." Octavia asked as Button's eyes removed themselves from her pussy and to the ten inch fake cock.

"I... I-I don't know what you mean, Mistress..." Button said as he poked the fake penis.

Octavia giggled, "Oh, so naive... I love it... Have you ever had a popsicle?"

Button nodded, "Yes, Mistress."

"Do to that," Octavia pointed to the cock. "As you would do to a popsicle."

Button reluctantly nodded as he took the cock within his hooves. It was big for him, larger than his own penis, and it held the same texture as his ownhaving veins surround it with impeccable detail. Button slowly stuck his tongue out as he began to lick the cock. A taste of something sour immediately filled his mouth and he wanted to pull off of it, but Button forced himself to continue.

Slowly, he began to lick the fake cock's shaft in long strides, leaving small trails of saliva on its rubber-like surface. His eyes looked over to Octavia, who had a hoof placed on her marehood, rubbing gently as she watched. Button averted his gaze and continued to lick the cock, every now and then taking the head of it in his mouthall in attempts to please her.

Octavia let out a soft moan as she watched the little teaser show before her. Her hoof gently tickled her clitoris, while she watched Button suck a cock in front of her, causing her mind to run wild with excitement. A few more moans escaped her mouth, as she watched him put the cock deep in his mouth and causing him to gag.

Button tried his hardest to do more with the cock then he'd do with a popsicle. He attempted to shove just the head of the cock into his mouth and accidentally slipped, making it hit the back of his throat. But this received a response from Octavia that, he assumed, was good. He began to make the cock go deeper into his mouth, purposefully trying to choke himself with it to appease her.

However, she stopped him, pulling the strap-on from his mouth, leaving only a string of saliva dripping from it. Button stared at she with the same worried expression, but she simply smiled. Grabbing the jar of lubricant, she opened it and stuck the majority of the cock in it, giving it plenty of lubrication. Afterwards, she put it on and stared at Buttonthe fat erect cock hanging from under her as she stood on the bed.

"Turn around, my dear Button," she asked, and Button obliged, turning around for her.

Octavia grabbed the braces and put them on the colt once more. She brought the cock just at his rear entrance, leaning over him, taking a long sniff from his mane. She gently kissed the top of his head and brought her mouth to his ear.

"This is where the fun begins. Try to relax and enjoy it. It will be easier if you do. Take it from experience," Octavia whispered.

"I-I don't know what you mea"

Before Button could finish his sentence, his words were replaced by screams of pain as Octavia thrusted the fake dick into his asshole. The force was impeccable and exciting, and she laughed softly as she watched Button cry in pain.

"I told you not to speak, did I not? No screaming during this, either," Octavia continued thrusting, slowing her pace but keeping the same force behind it.

Button placed his hooves over his mouth, trying to muffle his own screams the best he could. It was to no avail, as each time he did scream, Octavia would thrust harder and harder, making the pain increase. He couldn't take it. He wanted it to stop.

"P-please! M-M-Mistress! It... It hurts!" Button cried, begging for her to stop.

She slowed down, and spoke with malicious intent. "Oh, my dear Button, you should be happy. You should enjoy this and appreciate that I even bothered to put lube on this thing."

Button was crying, doing his best not to let his groans of pain escape his lips. Octavia's body shivered with the excitement that this small amount of torture was bringing. He was getting what every stallion should face when being overzealous with a mare's hindquarters.

"Now, since it hurts too much, I suggest you relax. Let your body enjoy it and it will hurt less," Octavia kissed his head again before thrusting once more.

Button did his best to relax and take it in. The pain was still great, but it had subsided from the start. As Octavia continued to thrust and Button's mind wandered, he began to feel a new sensation fill his groin. He lifted himself up slightly to look underneath him. What he saw was his penis: much larger than usual.

N-no! D-don't do that! He cursed himself as he collapsed back down, his face going red with embarrassment. W-why is it doing this? It only does this in the morning!

Octavia slowed her thrusts as she stared down at Button and saw his blushing. Quickly peering under him, she saw he was fully erect. This egged her to go further, wanting to make him cum long before she could. She pushed into him deeper and faster, making him cover his mouth once more; attempting to muffle more screams.

Cum for me, my little colt... Octavia thought as she lightly grunted with each thrust.

As Octavia thrusted, Button felt his groin tingle intensely, making him want to squirm, but was stopped by Octavia holding him in place. He felt something within him burst with excitement, a new feeling filling his mind. A wave of energy coursed through his body as something shot out from his penis. He let off a quiet moan of his own as a wave of relaxation hit him. Octavia had stopped, now.

"Mrmm... You lasted longer than I thought you would, Button," Octavia pulled the dick from Button's ass, taking the strap-on off and setting it to the side. “But, I am sure you enjoy cock in your ass, don’t you?”

Button said nothing and was relieved when the object left his anus. An ‘open’ feelingalong with this exciting onewas left behind for him, as his rump stayed in the air. He felt Octavia's hoof gently caress his testicles before his anus was filled again. Button let out a small yelp as Octavia pushed the vibrating butt-plug inside of him, turning it on to "low." She turned Button around and presented herself to him againthe same smile on her face.

"Now, it is my turn for pleasure... Do not worry, I gave you something to keep you motivated, but I wish to be pleased." Octavia smiled as his upper body squirmed from yet another sensation hitting his bodythat of a vibrating dick.

Octavia laid there, awaiting Button to dive on forth, and ravage her marehood. Button was unsure on what to do, and was having trouble moving while his legs were braced and his anus filled with a vibrating dick. However, he managed to slide forward, bringing his face to her cunt.

His nose accidentally touched her pussy as he moved forward and it was covered in a thin layer of liquid, filling his nostrils with the smell of something alluringa strong musky scent mixed in with a rosey tang. It made Button feel queasy, but he pressed forward a little more, sticking his tongue out as he began to lick.

Octavia felt his tongue gently press against her folds. She giggled at his naive efforts to pleasure her. His licks were fast, hitting the wrong spots and quite predictableeven if he was only licking for a few seconds. Octavia lifted his head a little, looking at him with a malicious smile.

"We won’t get anywhere at this rate. You are seriously a joke of a colt, you know," Octavia insulted the colt, making him frown. “In fact, I am starting to think you prefer colts. You did better with the fake dick than you are doing right now.”

"B-but, Mistress, I'm trying really hard! Honest!" Button said, trying to move back to her cunt.

"Oh, I can barely feel it. I think you are lying. Maybe you deserve to be punished with the strap-on agai"

"No!" Button yelled in retaliation. He quickly slapped his hooves over his mouth after he yelled, shaking his head.

Octavia raised a brow, leaning over to grab the strap-on.

"I-I'm sorry, Mistress..." He apologized quickly. "Please... I-I'll try harder."

Octavia looked back at him and smiled. "Then do so, my dear."

Button moved back to her cunt, slowing his rapid licks and making the lick the entirety of her vagina, in attempts to get a response from her. Octavia let out little sighs of contentedness as he did, making him feel slightly accomplished. I really need to make her feel good, so she doesn't punish me... But I don't know what to do! Button berated himself as he continued; his licks had slowed to the point where it took him a few seconds to lick the entirety of Octavia's pussy.

Octavia, unbeknownst to Button, was receiving far more pleasure than she led on. Her body was nearly shivering with ecstasy and excitement, that she was about ready to burst. She attempted to quell her pleasures by focusing on other things, like keeping her composure, but it only made it harder. Wanting him to panic, she decided to turn the vibrator up to "high" to really spice things up.

Button yelped loudly as it was, and Octavia pushed Button's face into her pussy, giving him no room to breathe. He had no other choice but to lick his little heart out while the vibrator pleased him immensely. Button's groin was flaring up again and, with his oxygen lacking, it caused his licks to become sporadic and failed to pleasure Octavia, giving her some relief.

Octavia watchedand feltButton's struggle. Her eyes were staring at his small erection, watching it twitch violently, as the vibrator massaged his prostate. It amused her to no end how easy it was to pleasure this colt and it also excited her for the future days, for when she can punish him for getting off before she did. Just as she was about to pull away, she felt Button pull away and gasp for air. After he did, he let off a long moan, his cock shooting another few spouts of semen onto the bed.

“Oh... It seems you have made a mess, Button.” Octavia smiled. “May you be so kind as to clean it up? Preferably with your cute little mouth”

“W-what?!” Button shouted, only to have Octavia shove his head into the small puddle of drying semen.

“Clean it up, or I will make you eat something far worse. Something yellow comes to mind...” Octavia tapped her chin maliciously while the colt’s face was covered in his own semen.

Slowly, Button’s tongue glided along the bedsheets, taking in the salty taste of his own semen. It made him want to gag, but he did what he was told and took in the cum. Octavia gently brushed his mane as she watched.

“Will you apologize, my dear Button? You were awfully rude to your Mistress,” Octavia said.

“I-I’m sorry, Mistress...” Button apologized as he licked the rest of his mess up. “I-I’ll listen from now on...”

Octavia giggled, turning down the vibrator to "low" again. Slowly, she repositioned herself to be facing Button. She removed his leg braces and allowed him to sit on his rumpwhich caused him more discomfort, as the vibrator pushed deeper inside of himso she could admire his little penis.

She gently brought a hoof to it, staring at cum that had escaped and landed on it, and gently stroked it. It was wet, as expected, and it was ready for her. She wanted to suck Button off and give him pleasure once more, as this would be his only gift. Octavia looked at Buttonhe was cringing and blushing in pleasure. He was finally enjoying this.

"I'm happy you are enjoying this, and I am sad at the same time..." Octavia smiled, bringing her muzzle to his cock, gently sniffing it and allowing his cum to slide onto her nose.

She gently raised her head and kissed the colt on the lips, letting her tongue dominate his mouth. Button's face held a massive blush, and he was unsure how to retaliate. He'd never kissed a girl before, so he just did nothing but blush, his eyes wide open while Octavia's were closed. Octavia's tongue attacked his before she pulled out, a long string of saliva drooping from their mouths.

Button watched as Octavia brought her head down on his dick, feeling her wet tongue surround it and slowly caress it. He struggled to contain a moan as the same feeling from before returned to his groin. However, it was heightened by the fact he had a vibrator gently massaging his prostate. Button couldn’t help but enjoy the new feelings this brought on; the multitude of sensation racking his virgin body was extraordinaryto say the least. He felt relaxed, composed, constantly being dumbfounded, and pleasure.

I never knew what pleasure was until now... Button thought I always thought 'pleasure,' meant something like enjoying good food, or playing a great game. But this... Feeling all of these wonderful sensations flowing through me... That's true pleasure.

As Button finished his thought, he felt the massive rush to his groin once more and felt his releaseright into Octavia's mouth. Octavia took it all, the small amount that was there, and pulled off, moving back to his lips and kissing him, spewing his own load back into his mouth. The salty taste returned to Button's mouth quickly, making him gag. He tried to pull back, but Octavia held him firmly in place. So he swallowed the awful-tasting liquid, gagging after Octavia pulled off.

Octavia giggled and turned off the vibrator, finally pulling it out of Button Mash and giving him some relief. "You do not taste too bad, Button. I was hoping you would agree. No matter."

Octavia laid on her back once more, presenting herself. Her pussy was glistening brightly, from all the excitement and ecstasy that flowed through her veins. She was close to finishing, and she wanted Button to finish her off so she could fall asleep with him in her hooves.

"Put your dick in here," Octavia commanded bluntly, pointing to her pussy.

Button raised a brow, confused beyond belief, "H-how...? How does it even go in it, Mistress...?"

"You are so naive and I love it!" Octavia giggled loudly, "Just do as I say. Much like I was doing earlier to you."

Button was still unsure, but he moved forward and placed his upper body on Octavia's stomach, gently aiming his cock for her marehood. He slowly pushed his dick against her cunt, penetrating it lightly before pushing it deep inside her. Well, as deep as his dick would allow. He felt a wetness surround his cock, and then he felt her pussy squeeze it gently.

A soft moan escaped Octavia's lips as Button began thrusting. Well, his bad attempts at it. They were quick and pleasureless, but his dick was brushing against her clitoris, still making it enjoyable for her. Button eventually slowed down after a few more thrusts, clearly tired. He just pushed into her repeatedly and Octavia began to moan louder, encouraging him to do better.

Button was close again. He felt his groin area go numb as he pushed in and out of the wet orifice. He did his best to tense himself up and hold it off, wanting to please Octavia first. He pushed deeply into her, slowing his thrusts and allowing her to feel the most pleasure. At least that's what he could tell from her moans. Button watched as Octavia brought a hoof to where his dick was entering and he watched as it furiously rubbed against a nub that protruded out of the orifice. He was unsure what it was, but Octavia was going wild now, her body shaking as he thrust into her.

Octavia was close. She could feel her entire body going wild as she furiously pleasured herselfwith the aid of Buttonand the constant rush of abusive thoughts entered her mind. Her heart was racing faster than it ever was before, adrenaline coursing through her veins, her body filling with ecstasy and her mind turning into euphoric mush. After a few more flicks of her clit and thrusts from Button, she felt her snatch fill up with some of his warm seed, and her body orgasmed intensely.

Button collapsed onto her stomach as Octavia let out a loud moan, and stretched her head to the headboard of the bed. For the next minute or two, she felt nothing but bliss and relaxation, having finally reached the most pleasing climax in her entire life. Another minute or two passed by and Octavia sighed, opening her eyes and staring at Button Mash. He was dead tired and breathing heavily on her stomach. She gently brought Button Mash to her chest and rolled onto her side, hugging the colt tightly.

"Mmmm... We are going to get along well, Button Mash..." Octavia whispered, kissing the colt's ears.

Author's Note

This story will belong to my version of the "Columbineverse" that the parasprite is designing. As I also said in the description, it's a side story to another story I'll write later on.

I might add a few other chapters if people enjoy this fic enough. But, I'm generally just going for a one shot of quick sex between an unusual pairing.

I use the word "prostate" somewhere in here. Just informing everyone: I don't really care if it's not correct. I just didn't feel like checking if a horse had one or not. Even if they didn't, most of these ponies are given human qualities anyways. So, y'know.

Anyways, hope you enjoy. Some of my editors are expecting more from this and, as I said, if people really enjoy this, I might write a few more of the Coltcapades. Maybe a bonus chapter.