Ropes and Chains and other Delightful Things

by Caladis

Rating: mature
Tags: Sex, Zebra, Sweetie Belle, Anthro, Apple Bloom, My Little Pony: Friendship is Magic, Alternate Universe, Porn, Fetish, Rarity, Profanity, Scootaloo, Random, Slice of Life
Length: 9282

The CMC explore becoming dominatrix's with the help of a Zebra Merchant

Written for Pepsi Addict for Summer Sin 23.

Set in an alternate Universe where the CMC did not get their Cutie Marks in 'Crusaders of the Lost Mark.'

A ponies' first heat is hard. It's worse when you don't have a cutie mark to allow you to indulge in summer fun like the rest of society. When Scootaloo is told that her retort to a proposition makes her sound like she's a dominatrix, she naturally has to investigate what that means in case that she and her friends can earn a cutie mark as one. A reliable source points them towards a Zebra that can help them...

All characters are 18 or older in this Fic.

Published 2023-08-04 10:50:00 UTC
Last updated 2023-08-04 10:50:00 UTC

Chapter 1 - The Plan

Summer.

Long days and beautiful nights.

Swimming in the local pond. Play dates. Sleepovers…

That almost magical time of year when the colt next door just seemed to be a little cuter, even if they were still annoying.

Fun for the foals, headaches for the parents.

There was nothing quite like the combination of school being out for the summer, with nothing better to do, and then going into heat, with nothing to distract you. Nopony could say if school being out for the summer was meant to keep colts and filly’s apart, so they weren’t cooped up in the classroom together or so that they had time to ‘play’ without it being the teacher’s fault.

Either way, it was more time for the Cutie Mark Crusaders to figure out how to get their cutie marks… at long last. They were ‘late bloomers’ by every definition, with several younger ponies being gotten cutie marks before them. It was getting old quick.

Having a cutie mark would give them more access to adult type activities that fillies and young adults without a cutie mark weren’t allowed to do. Of course, nature in general didn’t care about whether a pony had or didn’t have something, and it didn’t take them long to realize that they were going into heat. Again.

This wasn’t their first heat, but it might as well have been. Not having a cutie mark greatly restricted what they were allowed to do despite being eighteen now.

The looks the younger colts had been giving them was unnerving. The looks the older stallions were giving them was worse. The three of them agreed amongst themselves that Sweetie Belle was the cutest of the three of them but now all three of them were getting extra attention and they weren’t sure that they liked it.

Being eighteen had its advantages, mostly in feminine development. Sweetie Belle had an almost classic beauty, complete with the largest rack of the three of them, with a commendable Size C cup size. Apple Bloom was muscular and well-built from working on the farm, and while her chest was smaller than Sweetie Belle’s, as only a Size B cup size, it was clear that she’d at least give her older sister a run for her money once her tits finished filling out completely. Scootaloo, had the smallest rack, but she liked that since she preferred to be cool… not cute. From her time on the scooter and other athletic activities, she was lithe with a fit, trim and small chested body. She could still pass as a younger teenager and not as the adult that she was. They were legally considered adults at eighteen years old, although without a cutie mark, they were still treated like children when it came to certain things, which made everything else harder.

Diamond Tiara and Silver Spoon were good friends with the Crusaders following that disastrous Student Pony President incident years ago, but they couldn’t help them with their recent crusading while having their own heat to deal with. The girls weren’t interested in dating until they got their cutie marks, and they weren’t looking for a one-night stand… at least not one with a pony they would see around town every week. All of them had been warned of the trouble that ex-coltfriends could cause… especially in a town as small as Ponyville. Still… being in heat, again, without a coltfriend was borderline unbearable.

Apple Bloom and Sweetie Belle were already waiting in the old clubhouse when Scootaloo came through the door with a huff.

Apple Bloom turned to her friend and raised an eyebrow. “Somethin’ wrong, Scoots?”

She sighed. “Just the usual. I’m still in heat and the colts and stallions can smell it. It’s so hot that I’m sweating in places that I didn’t know could sweat.”

The two girls exchanged a look and Apple Bloom responded. “Scoots… ya’re wearing a white cotton t-shirt and no bra. Yah would almost be less obvious if yah went naked. We can see yare tits and nipples as clearly as if yah wanted everypony ta look at them.”

Scootaloo looked down at her sweaty wet t-shirt with disdain and pulled it off, exposing herself. “Are these stupid things really that cute? I don’t see what the big deal is.”

The two girls looked at Scootaloo’s A-cup sized chest with a slight blush. Apple Bloom was almost envious of Scootaloo’s smaller chest, given that her larger chest was starting to interfere with her ability to do certain tasks on the farm. She didn’t know how Applejack managed as well as she did with her rack.

Sweetie Belle smiled and answered the question. “There’s a cup size for every colt. Some like ‘em big and some like them small. If you ask me… that is part of the reason why Diamond and Silver aren’t willing to help us right now. Me and Bloom have bigger tits than both of them and while that might not normally bother them, during heat, it’s impossible not to notice.”

Apple Bloom nodded. “Here. We have a few clean, dry shirts on stand-by. Put this on and let’s talk about how we’re goin’ ta get our cutie marks today.”

Scootaloo finished putting the shirt on and smiled. “I have the coolest idea… if I can figure out what it means and how to do it.”

Sweetie Belle beamed while Apple Bloom seemed to hop in place, bouncing her modest tits up and down in a mesmerizing motion. Scootaloo wasn’t interested in girls, other than Rainbow Dash, but her heat was making even normal interactions more sexual. They had been going into heat since they were twelve, but they still didn’t seem to have a good way to deal with it. Yet.

Scootaloo had to shake it off and focus. “While I was in town, one of the bolder colts asked me if I wanted to hit the hay with him in an alley to blow off some heat. I told him off but said, and I quote, ‘How about I tie you to a tree and beat the crap out of you?’ A nearby mare overheard me say that and she commented that, ‘With that attitude… you’d make a good dominatrix.’ Now… I’ve never heard that term before and the mare got flustered and wouldn’t tell me what it was when I asked her what it meant. So, I’ve spent the better part of the last two hours asking mares around town what a dominatrix is and nopony will tell me! I know it’s something we’ve never tried before so how cool is that?”

Sweetie Belle clapped her hands together in excitement. “I bet Rarity knows! Let’s go ask her!”

The cutie mark crusaders entered Carousel Boutique and waited for Rarity to finish what she was working on. Time and experience had taught them to be patient when it came to getting anything from Rarity and fortunately, they didn’t have to wait long today.

Rarity looked up from the completed dress with a frown. Sweetie Belle hedged a comment. “Is something wrong, Rarity?”

Rarity shook her head and tutted. “It’s not wrong, per se, but it’s definitely not my style. However, this is exactly what the customer wanted so I’ll just have to wash my hands of it and hope they don’t brag too much about where they got it from. This was also the last commission I had waiting for completion so now I have nothing to do! The next Counsel of Friendship meeting is over two weeks away. You girls wouldn’t happen to be free, would you darlings?”

Sweetie eyed her sister with suspicion. “You want to update our measurements again and then make us some extra frilly dresses to wear around town to advertise the store since your bored.”

Rarity wanted to deny it, but she couldn’t. “Normally I’d just start making the dresses and then talk you into it later once they were almost done since I put in such a lot of work, but I can’t do that anymore. I can barely keep up with your consistently updating bust sizes. It won’t take long, I promise.”

Sweetie nodded. “Alright. We’ll help you with the store if you help us.”

Rarity smiled warmly at her sister as she got up on the podium for new measurements. “Of course, darling. Anything you want.”

Rarity had started taping Sweetie Belle when Scootaloo asked the question on their minds bluntly. “Do you know what a dominatrix is?”

Rarity’s eyes tightened in a way that showed her displeasure, but she kept her voice under control. “I trust that you have a good reason for asking that?”

Scootaloo relayed the same story to Rarity that she had told to her friends earlier while Rarity got the new measurements for all three girls.

Rarity mumbled to herself. ‘I don’t care what Cream Heart does with Button Mash behind closed doors in the privacy of their own home, but she needs to stop corrupting the town’s fillies and younger mares.’

Rarity cleared her throat. “I don’t suppose there is any point in trying to talk you out of this, so I won’t try. That being said… there is more than one way to be a dominatrix. As a matter of fact… there are at least 19 different styles… though I doubt that girls as young as you could pull off all of them. In general, a dominatrix, as the name implies, is normally the dominant one. The most common time is during sex or during some other sexual foreplay. However, outside of the bedroom, it can also involve manipulation… or emotional control… like offering to take a partner out to eat but then changing your mind halfway there and claiming that they didn’t really want to eat there in the first place.”

Apple Bloom muttered. “That kinda sounds like what Diamond Tiara does ta Silver Spoon. Ah would have never thought that what she was doing was a form of domination, but it fits. Ah know ah wouldn’t like ta be a long-term relationship like that.”

Rarity continued. “Very few ponies keep up a dominatrix role or attitude permanently although we could all probably name a few ponies where that attitude comes more naturally. I’ve personally found that being too assertive all the time can hurt relationships as the deeper relationships do require a degree of give and take. Acting as a dominatrix is usually just for certain prearranged encounters, sexual or otherwise. The other side of the coin is the submissive. They take the punishment from their dom, but they can also take the lead in meeting the physical, mental or emotional needs of their partner. Like… throwing a tea party perfectly suited to their dom’s taste. Some ponies play a dom or sub role professionally for money. They tailor their attitudes to exactly what the client wants. It can be simple or complex and of course, requires patience and practice.”

Scootaloo had been following along closely. “So… you can get a cutie mark in being a dominatrix?”

Rarity winced. “I can’t say for sure that I’ve ever seen one… and if such ponies exist, they probably live and work in Las Pegasus where the commercial practice of such a trade is most common. If you’re going to give this a real try, you’re going to need the right supplies. Dominatrix leathers, lingerie, whips, chains, ball gags…”

Sweetie Belle frowned. “And where do we get all that?”

Rarity fanned herself, clearly overheating from the hot under collar conversation. “Darling… there are no sex shops in Ponyville… and the regular general goods stores only can provide such things from special order, as they don’t carry them in stock normally. And even if they did carry them in stock, you would be considered too young to buy any of it, despite being eighteen.”

Apple Bloom sighed dejectedly. “This is about our lack of cutie marks again, ain’t it… Then how are we supposed ta get any of it?”

All three sets of eyes turned to Rarity, and she sighed. She seemed to consider the question honestly but still didn’t know what or how much to say. Her thoughts were brooding.

Buck it… they are eighteen. If a line is going to be crossed, then it needs to be crossed cleanly. And fashionably.

“There is a traveling Zebra merchant that sells these types of adult toys that just so happens to pass through Ponyville regularly. I believe he may be related to Zecora, but I can’t say for certain. Zebra culture is… different than pony culture. He would be willing to sell you anything and everything that he sells without question. He might even be persuaded to offer a discount for the right exchange of services. Full dominatrix gear is expensive, but you only need the toys… I’ll make you girls a full set of dominatrix leathers and submissive lingerie to wear during your… sessions. You may have to be patient with him coming and going on a whim… just check the town marketplace everyday and you’ll find him eventually. I should have the outfits done for you before you get the toys you need.”

Scootaloo nodded. “I guess that means that we’re going to be doing something normal today while we wait… but… how are we supposed to pay for the toys? Aren’t they expensive?”

Rarity tilted her head in agreement. “Yes… the cost can really add up. I’ll tell you what… I’ll sweeten the deal. If you three will model both a frilly dress and another ‘upscale everyday outfit’ made by me to an official promotion of my store… I’ll pay you the same as I would normally pay to a professional model, and you can use that money to buy your new toys.”

Sweetie Belle licked her lips. “That sounds too good to be true… why ‘hire’ us?”

Rarity bit her lip. “The new line of clothing I’m creating is for older teens and young adults. It’s an untapped market in the town given that most of the clothes I make are for older adults. For better or worse… there are very few Teen and young adult models… so I’d more than likely be forced to hire you or a few of the other teens or mares in the town to model the outfits anyways. Given a choice, darling, I’d rather pay you and your friends than some random pony from the town. Kills two birds with one stone.”

Apple Bloom eyed Rarity uncertainly. “Ah may not be the element of honesty, but ah can tell when somepony is holding back.”

Rarity hated being called out, but she knew it was true. “Plausible deniability, darling. I don’t want to be accused of buying this stuff for you… and I’ll deny even having told you where you can buy it for yourselves. But I won’t stop you from buying it or using it… as long as your careful. You all may well be adults, but you are still accountable to your families. Sweetie Belle has my permission as her guardian to be a little risqué, but the rest of you are on your own. Whatever happens… I’m washing my hands of it.”

Chapter 2 - The Rules

The next week passed by criminally slowly as the Cutie Mark Crusaders looked for the mysterious zebra merchant in the Ponyville Marketplace every day before leaving to do other things. One of those things ended up modeling summer dresses and the new sets of ‘upscale everyday outfits’ for older teens and young adults at an event hosted by Rarity at the Carousel Boutique.

To the girls’ satisfaction, the event was a success and Rarity confirmed several new orders for her efforts. And of course, as promised, Rarity paid them 100 bits each for their modeling work. While Scootaloo scoffed at the wage received, Sweetie Belle was able to confirm that most amateur clothing models that were just starting out could earn as low as 20 bits per hour, so while the wage wasn’t ‘generous’, it was reasonable. Apple Bloom hadn’t cared one way or the other so long as it was enough to get what they needed. Rarity had already secretly given all three of them their lingerie and leathers.

While Rarity wasn’t hurting for money, she had been concerned about being bored. Having no work stifled her creativity and worse… her more recent work for lingerie and dominatrix leathers wasn’t something she was willing to openly sell or advertise (She had a reputation to uphold after all) although she knew a few ponies that she could discreetly work with for ‘secret orders.’ Rarity would never admit it, but the cutie mark crusaders had given her a great deal of inspiration, but that’s another story for another time.

Once again finding themselves in the Marketplace, Scootaloo sighed loudly. “Do you think he’ll be here today?”

Apple Bloom shrugged while scratching the back of her head. “Ah don’t know but, in all honesty, today is the first day that we’ve had the bits ta buy the stuff. It would have been worse ta have found him and not been able ta buy anything or make a deal.”

Scootaloo nodded in agreement but hedged a question. “So, who should do the talking when we finally meet him?”

Sweetie Belle considered the question thoughtfully. “Hmm. Bloom has the most experience buying and selling things from her work on the farm. If anypony can get us a discount, it’ll be her. Of course, she’ll need our permission to make deals that involve us. I trust her so I have no problem giving her permission. It won’t look good if we start arguing in front of him.”

Scootaloo nodded. “Yeah… I agree. There’s just one problem…”

Bloom frowned. “An’ what’s that?”

Scootaloo looked at both her friends with a slight amount of worry. “I’m not sure it matters if we can afford to buy everything or not. The final problem is that we don’t know what everything is for or how to use it. Bloom will have to convince this guy not only to sell us this stuff, but also to teach us how to use it.”

Sweetie winced at the truth of that statement. “A lot of the adult stallions in town have been looking at us with a hunger in their eyes since we started our latest heat, but we also know that none of them would dare touch us without a cutie mark, despite our age. We’re going to have to hope that zebras have fewer taboos or that we’re old enough to consent within zebra culture. Rarity did say that their culture is different. I don’t see how he could teach us to use this stuff without using it on us himself.”

Bloom’s eyes widened and she spoke in a hushed tone. “Ah think we’re about ta find out. Look alive girls… we got us a zebra.”

They all looked towards what had to be the most isolated spot in the marketplace. If the zebra wasn’t so easy to spot, he might have been easy to miss. They all causally walked over to him, to disguise how eager they were to finally meet him.

The zebra smiled down at all three of them. “Welcome to my humble market stall. What catches your eye today?”

As they looked down at the wares, they froze in place. The stall had whips, chains, necklaces, bracelets, spikes and several things that they couldn’t even identify.

Apple Bloom picked up a hollow cylinder in one hand and another large plug with the other hand. “Would ya mind explaining what these are and how to use them?”

The zebra smiled. “Of course! The cylinder is an Anal Dilator which is used to open your tailhole so a stallion can put his cock in your tailhole. Just be sure that the dilator is large enough to accommodate your stallion’s cock. Between you and me, the hospitals hate having to remove a dilator from a stallion’s cock that was too small him. And the plug device is a butt plug. The butt plug serves two purposes as well. The first purpose is also to prepare you for anal sex, but the second purpose is to give you more pleasure during regular sex. Leaving the butt plug in during sex puts more pressure on your clitoris and will in turn make you orgasm faster and harder. If the stallion knows what he’s doing, it can be very pleasurable for both ponies.”

The girls were… shocked… by the explanation but were also grateful at how blunt he was in explaining what those items did. He wasn’t treating them like children, unlike how most of the rest of the town still did.

Sweetie Belle smiled with a timid expression. “That’s… very, uhm, informative. We were told that you might be related to Ponyville’s resident zebra but nopony knows for sure. What’s your name, mister?”

He bowed with a smile. “Ah. I visit my sister Zecora from time to time, but I don’t like to leave my name where Royal Guards, lawyers, or angry fathers can find it… so, you may call me Mr. Zebra.”

Sweetie Belle tilted her head in confusion. “We know Zecora… why don’t you rhyme like her?”

Mr. Zebra laughed heartily. “She rhymes like that because it’s traditional for zebra potion masters to do so. I prefer regular pony speak to better connect with my customers.”

That made sense so Sweetie Belle pushed forward. “Well, Mr. Zebra. Are you sure that you don’t mind three mares our age, without cutie marks, looking at your wares?”

He shook his head at looked at them appraisingly. “Mares your age? You are at least eighteen, are you not? In zebra culture, a filly can be mated once she has her first heat. Zebras don’t get cutie marks like ponies do, but some of us chose to get tattoos where a pony cutie mark is supposed to show up after the first heat happens. Without a cutie mark to guide us, we choose to use nature’s way of telling us when it’s time. The first heat can be very young, but nature wouldn’t let you go through heat if you weren’t ready for foals. Physical age aside, I can smell that all three of you are in heat, so therefore in zebra culture, you are old enough to buy what I’m selling, if you have the bits to pay for it.”

With that tidbit of information out of the way, Sweetie Belle backed off and let Apple Bloom take over the negotiations.

Apple Bloom nodded. “We want ta try ta earn cutie marks as a dominatrix so we need everything ya would recommend in pulling that off. We already have dominatrix leathers and lingerie.”

Mr. Zebra nodded as he gathered a large amount of his wares. “If all three of you plan to do this together, you will need at the very least: three butt plugs, one anal dilator, one cat of nine tails whip, three blindfolds, one set of chains, a sex swing, a ball gag… maybe two sets of handcuffs.”

Apple Bloom blanched at the cost. “We only have 300 bits… we can’t afford all that unless ya’re willing ta make a deal.”

Mr. Zebra closed his eyes and appeared to be lost in thought for a moment. “I suppose you need somepony to show you how to use everything also, correct?”

Apple Bloom winced. “We can’t afford ta pay ya for your time. Can we make an arrangement?”

Mr. Zebra opened his eyes and smiled. “As it happens, I often pay mares for their time. The road is lonely. Despite my sister’s presence, Ponyville is still ignorant towards zebras, so I don’t find much companionship here despite my willingness to pay a generous amount. I suppose I could afford to sell you all these wares for 300 bits and install it for you while also agreeing to teach you how to safely use it… since sex will be involved. Do you consent to sex and agree to these terms?”

Apple Bloom looked at her friends, who both simply nodded. “Ya have a deal.”

Mr. Zebra packed up his stall and closed early, opting to follow the Cutie Mark Crusaders back to their clubhouse. He sat the wares down and started to install everything, but he also took the time to hold a conversation with the girls as well.

“Now. I’m going to explain the rules while I’m installing everything.”

Scootaloo scoffed. “There are rules?”

Mr. Zebra nodded, a serious expression on his face. “Yes.”

Sweetie Belle didn’t want him to leave so she responded before Scootaloo could say anything else. “So, what are the rules?”

Mr. Zebra hung the sex swing in the middle of the clubhouse and was adding supports.

“Generally, the rules are simple. Rule number one: Only Dom and Sub with people that you trust. They may have rules of their own, but they need to respect your rules and your limits. Rule number two: You need to know yourself well enough to set limits given that without limits things may happen that you don’t like, and you want to enjoy these experiences instead of regretting them. Rule number three: Always have a ‘safe word’ that you can utter to stop the encounter if it starts to get out of hand. The safe word can’t be ‘stop’ or ‘no’ because it’s common to accidentally say those things in moments of passion. With the three of you, each of you should have your own unique safe word. Rule number four: Always agree before the encounter starts on what exactly the plan is. It doesn’t have to ruin spontaneousness, but you do need to be in agreement on the general nature of what is going to happen before you start. And finally, rule number five: Use protection for all encounters that include actual sex so that there aren’t any accidental foals. Do you have any questions?”

He moved on to install the chains on one of the walls when Apple Bloom spoke up. “Ya seem very experienced in this. It seems obvious that ya can’t say a safe word if ya’er using a ball gag but ah’d like ta understand why the rules are so important?”

A moment of silence passed with only the sounds of him working on installing the chains. “I had a mare friend who liked to be choked during sex and another stallion friend who loved to choke during sex. They hooked up and there was no safe word and as the evening continued, they both got deeper and deeper into their own fetishes. Before any zebra knew what happened, he had accidently choked her to death. It was consensual sex, but you can’t excuse murder, even if it could be explained as an accident. He should have stopped but he was convinced that she wanted more. That’s why I insist on establishing rules for the encounters. If you go on to do Dom or Sub work for a living for clients, you will want rules for every client.”

The explanation made sense but also took the girls by surprise. Scootaloo cleared her throat. “We’re going to go change into something more comfortable and talk about the rules we want for ourselves while you finish up installing this stuff. We’ll be back.”

An hour passed and the girls returned to the clubhouse wearing their lingerie, not completely surprised that without distractions everything had been installed and reenforced so nothing would break. His eyes widened when he saw the girls.

Scootaloo was wearing a green set of lingerie that complemented her orange coat perfectly. It had the crotch cut out for easy access to her pussy and flaps that could expose her breasts. The flaps were undone, and her A cup breasts were exposed for him.

Apple Bloom wore a red lingerie that matched the color of her mane, with the same crotch cut out and breast flaps. Bloom seemed satisfied with how the lingerie made her B cup breasts look, also already exposed.

Sweetie Belle was wearing purple lingerie that also matched the purple in her mane. While also crotchless for easy access to her pussy, her lingerie was designed to accent her breasts, keeping them fully exposed, given that her C cup breasts were already too big for a securable flap to hide them. While technically wearing clothes, they were also technically naked with both pussy and chest exposed for their zebra guest.

He cleared his throat, seeming to be nervous for the first time. “You mares certainly came prepared. It makes me less unsure about doing this, but won’t your parents’ mind?”

Sweetie Belle pressed her fingers into her breasts to draw attention to them, drawing circles around her nipples causing them to go erect. “We all are eighteen, so I don’t think that matters much, but, if you want an explanation, here it goes. My parents left me in the care of my older sister. Not only does my sister not care that we’re doing this, but she also made us this lingerie and told us to seek you out specifically to buy what we needed. She also gave us the bits to buy what we got. I don’t care if my parents care what about happens in here. For that matter, I don’t care if my sister cares what happens in here.”

Apple Bloom went next, drawing the zebra’s eyes to her with a slow caress of her wet pussy. “My parents are dead, and my older sister and older brother don’t pay much attention to me. Ah know they care about me, but a girl my age needs more… attention… affection.”

Scootaloo, not wanting to be outdone by her friends drew the zebra’s attention with a quick flap of her wings only to turn around and bend all the way over, exposing her pussy completely with the prime angle to be mounted. She spread her ass cheeks with her hands to give him an even better view of her ass and pussy, and then turned her head to give the zebra a sultry look.

“My parents are exploring the jungles of Equestria. They left me in the care of my aunts who only pay token attention to me. My mentor seems to care more about being cool than being nurturing. These friends mean the world to me, and we all want either the same or similar cutie marks. So do you want these pussies or not?”

Not at all shocked by the vulgarness of the mares’ statements, their needs clearly displayed, the zebra started to get undressed and asked. “Do you have your rules ready?”

Scootaloo stood back up, not wanting to hold that pose for long if he didn’t start with her and Sweetie Belle answered his question.

“Yes. The rules. Given that you are older than us, we want a teacher/student dom/sub roleplay. Calling you Mr. Zebra already plays well into that. No choking. We want you to insert the butt plugs into all three of us, so no anal sex but we want you to not only fuck our pussies, but we expect you to finish inside of us to quell our heat. Teach us the proper way to use the equipment. If it goes too far for any of us, my safe word is ‘music’, Bloom’s safe word is ‘Apple Pie’ and Scoots’ safe word is ‘rainboom’. What are your rules?”

Now fully naked, Mr. Zebra smiled. “My rule is that I will follow your rules. Do you have a preference on who gets the swing, the chains or the handcuffs?”

Scootaloo shook her head. “Nope. Put us where you want us, Mr. Zebra.”

He nodded with finality. “Very well… let’s begin today’s lesson. Bondage 101.”

Chapter 3 - The Lesson

Given free reign over how to run his ‘classroom’, Mr. Zebra decided where to place his students.

Apple Bloom got chained to the wall, arms chained above her head with her legs spread as far as they could be comfortably, allowing free access to her breasts and pussy from the front. Despite how awkward it looked; she was comfortable. The current height placement of the chains gave the tall male zebra ample access to her wet baby making hole.

Sweetie Belle was placed in the sex swing, on her stomach, legs spread to give him access to her pussy from behind. Her breasts dangled towards the floor, feeling heavier than normal without a bra to support their weight.

Scootaloo was laying on her back on the floor, legs spread and pulled up to allow her ankles to be handcuffed to her hands. It was admittingly a little uncomfortable, but it spread her virgin pussy wide for what promised to be an unforgettable sexual experience.

Mr. Zebra took his time inserting the butt plugs into each mare, doing a good job in not hurting them but making sure that the plugs were fully inserted. It was a tight fit despite being the smallest adult size. Finished with the task at hand, he nodded.

“Now that all three of you have your butt plugs inserted, I will start the lesson by saying that the butt plug insertion was very important for this experience. I doubt that I would have had any trouble making a virgin cum, however, the butt plugs will make it that much easier. You don’t have to always use them, but when you do, it’s important to remember the following. When inserting the butt plugs into yourselves or into each other, remember that they need to be ‘tight’ to get the maximum benefit of placing pressure on your clit to help you cum, but not too far in. When these get too loose, you will need to upgrade to a larger size and remember… nothing ends up in your ass by accident. Hospital trips are embarrassing, and nurses hate it when patients lie about how something ‘accidently’ went into their ass.”

The three of them nodded and he continued, this time pointing towards Apple Bloom.

“The wall chains can be adjusted to accommodate nearly anyponies size, big or small, however they really aren’t meant for children. I would recommend not trying to use them on ponies younger than yourselves, cutie mark or no cutie mark. Moving on… As you can see, Ms. Bloom is secured to the wall, facing outwards, with her legs spread. This will give the stallion easy access to her cunt. Her hands and arms are secured above her head to make her breasts that much firmer and rounder to be played with. You could also secure a colt or stallion with the chains in the same fashion to play with his cock, either by rubbing it or mounting him from the front. While you could chain up somepony facing the wall… I wouldn’t recommend it. For a mare… being unable to bend forward would put a lot of pressure on her cunt, which more than likely would make the sexual experience painful… unless she is just that loose to begin with. It might work for anal, but not everypony likes anal. Furthermore, it serves no purpose for a stallion at all unless the plan is to play with his ass.”

He continued without asking if there were questions and without any interruptions.

“Moving along, we have Ms. Belle in the Sex Swing. Now, currently she is on her stomach with her legs spread giving easy access to her cunt via ‘doggie-style.’ You can also lie on your back holding your legs open or simply sit in the swing with your legs spread. However, being on your stomach in the swing is the best position for a stallion to get a blowjob separately from doggie-style sex. Alternatively, a stallion could also sit in the swing with you sitting on top of his cock in a cowgirl or reverse cowgirl style. The ropes are designed to hold the weight of two fully grown adults and I reenforced all the beams, so you won’t need to worry about anything breaking.”

He pointed towards Scootaloo. “And finally, the handcuffs. They can be used in a variety of ways but the more complicated you want them, the more sets of them you will need. Handcuffing a mare’s ankles to her hands on both sides is the most exotic placement you can manage with only two sets. It can be a little uncomfortable to lay on the ground like that, but I can assure you that the spreading of the cunt lips will make actual sex less painful, especially for a virgin. As far as stallions are concerned, simply handcuffing their hands together creates an exotic sexual situation that will turn them on. Are there any questions so far?”

The girls replied in unison, “No, Mr. Zebra.”

He walked over to a table and picked up the whip. “This is a ‘Cat o’ Nine Tails’, so named for the fact that the whip has nine short, knotted thongs of cotton cord. It has been used over the years as a means of punishment but, if used lightly, has bedroom applications for creatures who like a little pain with their pleasure.”

He walked over to Sweetie Belle and gave one light stroke of the cat to her ass, causing her to shriek in unexpected pain. He looked her over and found no marks had been left.

“Was it too much, Ms. Belle?”

She shook her head but couldn’t stop a tear from running down her cheek. “My parents never spanked me. I can’t say that my sister ever has either. I think it hurt more than it normally would because I’m inexperienced in being spanked. Maybe… just use your hands if you want to spank me?”

He nodded and brought his right hand down on her right ass cheek and then another on her left. Sweetie let out a yipe with each spank highlighting her point about being inexperienced, given that the light smacks didn’t even leave handprints.

Mr. Zebra hummed. “I see. A lot of stallions like to spank the mares they are intimate with as a normal part of foreplay and during the act itself to release tensions. You’re going to have to work on that. Maybe your friends can take turns spanking you to toughen you up.”

Sweetie Belle nodded and sighed. “I guess it’s only fair for the teacher to assign homework.”

He moved onto Scootaloo and brought the whip across her ass cheeks, this time leaving a faint mark. She jumped a little at the stinging sensation but didn’t yelp. If anything, she grinned.

“Can you spank me a little harder, sir?”

He nodded and hit her with the whip again. Her eyes fluttered and she moaned… “HARDER!”

He came down on her again, this time leaving clear marks on her ass and at least one mark across her pussy. “GRFRF.”

A small pool of liquid drained from her pussy and Sweetie Belle looked on in shock. “Scoots? Did you just cum from being spanked?”

Scootaloo moaned. “Sure did… would the teacher like a taste?”

Mr. Zebra kneeled before her and placed his mouth on her cunt, drinking deeply of the offered cum, lapping it up with his greedy tongue.

“Very nice. Sweet favor accented from innocence. There is nothing quite like eating out a virgin though I wonder how you can handle the pain so much better?”

Scootaloo was barely able to speak, euphoric from being eaten out, even if only briefly. She finally recovered enough to answer truthfully.

“I’ve crashed my scooter a few times in very painful ways. I once hit a tree so hard that the long pole that goes to the handles nearly went into my pussy, I was wrapped around it so tight. The thing with pain is that the more you experience the more it takes to hurt you. I’ll admit that I didn’t expect to cum from it but at least I know that I can now. It’ll make being a dominatrix professionally a little easier, maybe.”

Mr. Zebra walked towards Apple Bloom and brushed the whip against her ass and pussy in an upward swing. Apple Bloom found herself moaning also in pleasure from the impact.

Sweetie Belle fumed. “You too! Am I the only one that didn’t like being spanked?”

Bloom gasped. “The whip hit the butt plug and ah’ll say that it sent a shock through all of me… a pleasant one though. Maybe he just hit the wrong part of ya?”

Sweetie glared. “Alright… let’s try it again… aim that thing for my butt plug and pussy!”

Mr. Zebra walked back to Sweetie Belle from the front and placed his cock against her mouth. She opened to him, almost as if from instinct and he slide his cock into her mouth. Sweetie wrapped her lips around his pulsing member and bobbed her head up and down, taking it in as deep as she could without practice.

While he was enjoying the amateur blow job, he placed the whip just so and let it fall at the desired angle at a speed dictated by natural gravity, perfectly cupping her ass and cunt. The whip hit the butt plug and at least one strand seemingly wrapped around thighs and hit her pussy, nearly going in on its own. The experience was more pleasurable than the first two spankings but there was still more pain than she would have liked. It was hard to accept, but Scootaloo did do lots of painful stunts on her scooter and Apple Bloom probably got hurt working on the farm a lot and just never complained about it. By comparison, Sweetie Belle spent nearly all her free time, that she wasn’t with her friends, indoors. As such, it appeared that she wasn’t as suited to rough foreplay.

Sweetie’s eyes bulged from the sensation and her scream was muffled by the cock in her mouth. Her vocal cords hummed and caressed the cock in her mouth and without warning, one small rope fired down her throat.

Mr. Zebra pulled out of her mouth, and she wiped her mouth off with a hand. “At least I got that right.”

He shook his head. “That was only pre-cum, not a full orgasm, but yes, it was a very good blow job for your first time. What should I do next…”

Apple Bloom spoke up. “Ah think we got a good idea on how all this works now. We should move on ta the main event.”

Mr. Zebra smiled. “Ahh. But how should I go about that? I don’t often find myself with more than one mare and I’d hate to think that you all didn’t get equal attention.”

Apple Bloom smiled back. “Ah think one-on-one personal tutoring is in order. Ya’ve gone back and forth to each of us teaching the basics… but now we need ta finish up. Ah think you could probably focus on just one of us at a time until we’re done and then move on ta the next student.”

He clapped his hands in approval. “An excellent suggestion… but who should go first?”

Sweetie Belle cleared her throat. “It was Scootaloo’s idea so maybe she should get first dibs.”

Mr. Zebra closed in on the orange mare, who was now very aware of his presence.

Scootaloo gulped but tried to sound confident. “I’m ready.”

To her surprise, he kissed her. It was a sweet but sultry kiss that stirred her senses and made her even more aware of his, and her own, arousal. He kissed her lips and trailed down her neck and planted soft nibbles on her nipples, bringing both to rock hard pinpoints. He continued further down, kissing her stomach. He played with the ticklish points along her sides, eliciting a giggle that sounded innocently sweet against the backdrop of passion, and then continued lower… kissing, licking, and then sucking on the soft nub of her virgin clit.

Scootaloo moaned with sensation building, the butt plug giving her pussy and clit very little room for even his tongue. Lapping his tongue against her pussy, she found herself releasing directly into his mouth, filling his throat with sweet, fresh young filly cum.

She panted from the ecstasy of her release but found herself full beyond anything she could have imagined as he settled over her and slowly pushed his rock-hard zebra cock into her very small but very wet filly hole. She could feel a crunch and a tickle of blood ran down her thigh, marking her loss of virginity. She didn’t scream, which she was proud of, but she had a hard time not hyperventilating as the zebra rocked in and out of her pussy, slowing diving deeper and deeper until he bottomed out. As she looked down, she was shocked that his cock was barely halfway in her, but they both knew that it could go no further. He held the position, allowing her pussy to stretch just a little before he resumed rocking back and forth, bottoming out with every thrust.

She moaned, and panted, and moaned and then screamed as a joyous burst of pleasure overtook her as he came inside of her while her pussy clamped down on his cock in her third and best yet climax.

He pulled out slowly and all three girls watched the pale white cum drip out of Scoots well fucked pussy. In an act of mercy, he undid the handcuffs and allowed her to relax.

“Your lesson is finished. You may watch the others while you rest up.”

Scootaloo moved herself into a lounging position, too proud to admit that she was already sore
(and would probably be walking funny for a couple of days) as she settled in to watch her friends in the same way that they had watched her.

Mr. Zebra approached Apple Bloom next. One of the good things about being chained to a wall is that you had nowhere to go. However, on the other hand, one of the bad things about being chained to a wall was that you had nowhere to go. Apple Bloom squirmed a little in anticipation of what was going to happen. Having watched Scootaloo getting the full attention of Mr. Zebra gave her a moment to consider just how hot this situation was.

And Mr. Zebra didn’t leave her wanting.

He closed the distance and rested his hands on her firm tits. She had to admit that being groped was a little awkward, but she figured that was mostly because she wasn’t used to it. The soft kisses on her lips and cheeks were a nice display of affection, completely at odds with being chained to the wall in the first place. She moaned into the kiss only to groan as he seemed to settle under her and thrust upwards into her wet and wide-open pussy. Having her legs spread to the degree that they were allowed Mr. Zebra to spear her without much pain… though she was able to feel a tickle of blood run down her leg, confirming her loss of virginity as well.

He pushed his cock into her and bottomed out a little deeper than he had with Scootaloo. Either Earth Ponies had a deeper pussy or the angle that he was fucking her simply allowed him to go in further. Either way, it was pain and pressure mixed into a feast of emotions.

Scootaloo found herself rubbing her pussy to the sight of her friend being fucked. She knew that she couldn’t cum again but damn if it didn’t feel good to rub herself while watching. Sweetie Belle could only look on and groan, patiently waiting for her turn. She couldn’t rub her own pussy at the angle she had been secured into the sex swing.

The clubhouse was always a little warm in the summer, despite being in the shade, but the fury of fucking gave off a heat of its own. Beads of sweat formed on Bloom’s brow and dipped down her face only to land on her tits. Mr. Zebra was sure to lick the beads of sweat off her tits in an erotic display, his own sweat mixing into the fluids of sex, accented by the pulsing sound of his cock slamming into her pussy.

Clop, Clop. Clop. Groan. And sigh.

Apple Bloom’s pussy milked Mr. Zebra for all he was worth as they seemed to finish together. He pulled out slowly, as if worried about hurting her after the fact, and the girls watched in fascination as a huge dallop of cum dripped from Bloom’s pussy onto the clubhouse floor below her. He leaned back in and kissed her as he undid the chains. She wrapped her arms around him after her hands were free and continued to kiss him until her legs were freed as well.

With a chuckle, he put her on the floor beside Scootaloo.

“You girls are probably sore from the sex so rubbing your cunt’s will only make it worse, however… you could probably sooth each other by licking each other.”

Scootaloo looked at Bloom and she looked back at Scootaloo. “How are we supposed ta do it?”

Mr. Zebra motioned for Apple Bloom to lay down and she did so. He then motioned for Scootaloo to get on top of Bloom with Scoot’s pussy hovering over Bloom’s face while she was staring directly at Bloom’s pussy.

Mr. Zebra continued. “This position is known as a Sixty-Nine. This will let you to lick each other’s cunts at the same time. It works the same for doing a colt if you want him to lick your cunt while you’re sucking his cock. You may pleasure each other while I finish up with Ms. Belle.”

He walked back to Sweetie Belle and took up position behind her. His cock was well oiled from the mare cum of the first two girls he had fucked but he was still a gentle-zebra. He kneeled down to her perfectly displayed cunt and licked the entire length of it, finishing with a short kiss on her butt plug. Part of him regretted suggesting that they use butt plugs as he did enjoy both giving and receiving a good rim job, but today was about more than his own pleasure.

He gave her a few more good licks and then stood up to place the head of his cock at the entrance to paradise. Sweetie seemed to hold her breath as he slowly pushed inside her, worried that she was once again doing something wrong. He slid in with a minimum of effort or pain, causing him to frown.

“You… you do not appear to be a virgin. This is not your first time?”

That caught Apple Bloom and Scootaloo’s attention and all eyes were on Sweetie. Sweetie gulped. “I actually had sex for the first-time last week. He didn’t spank me at all and was very gentle… so I guess you don’t have to be any gentler with me than you were with the other girls… at least, not with the main event.”

Scootaloo was shocked but managed to blurt out a question. “Who was your first? And why didn’t it quell your heat?”

Sweetie Belle blushed and looked away. “Spike…”

Apple Bloom’s jaw hit the floor. “Spike? Ya fucked Spike an’ didn’t tell us?”

Sweetie couldn’t understand how this was so embarrassing for her. They had said that they didn’t want one-night stands and they meant it… but there were exceptions.

“I’m not proud of it. I dyed my tail purple and pretended to be Rarity. The way I was covered up except for my butt and pussy… he didn’t know it was me until after he finished. I hate to admit that my ass is as big as hers. As far as not quelling the heat… Dragons can’t get ponies pregnant, so it didn’t do anything for me other than having a good first time. Except… well… he’s still not speaking to me. I guess he’s upset at both me and himself for doing that to a close friend… even though he’s still unashamedly infatuated with my older sister even though he now knows full well that he can have me.”

Scootaloo nodded. “We’re going to have to talk about that later. For now, finish up.”

Sweetie looked back at the teacher. “I’m ready if you are, Mr. Zebra.”

He nodded. “Since you’re not a virgin, I’m not going to hold back. Brace yourself.”

Sweetie Belle grabbed onto the sides of the swing to brace herself and Mr. Zebra grabbed onto both her hips to brace himself. He had never slid out of her cunt while the girls had been talking about her previous sexual exploit and by now, her cunt was fully adjusted for his massive size.

One of the side effects of having fucked a dragon first was that Mr. Zebra was able to hilt his cock inside of Sweetie… giving a very satisfying clop, clop, clop sound as his balls slapped against her pussy. The girls were memorized by the sound and image of Sweetie being completely slammed with zebra cock.

Mr. Zebra leaned down and reached around, cupping Sweetie’s tits in his hands, giving them a squeeze and holding on for dear life as if he was going to be bucked off a horse. He arched his hips and pulled out as far as he could go only to slam back in, causing a muffled gasp to echo around the clubhouse.

Slam, Gasp. Slam, Gasp. Slam, Gasp.

Sweetie threw her head back with a silent scream of ecstasy as her pussy coated Mr. Zebra’s cock with a fresh batch of cum and he grunted, unable to hold back with the tight mare cunt milking him for all he was worth. Despite not being a virgin, it was still a very good experience for both of them.

He pulled out and cum dipped from her pussy. He undid the bindings that had secured her into the swing and she tried to stand, only to fall to the floor.

“Ow. I can’t feel my legs. I’m going to be walking funny for the rest of the week.”

Apple Bloom smirked. “Ah think all three of us will be. So… did we get our cutie marks?”

They all looked at their flanks only to be disappointed when nothing happened. Mr. Zebra shook his head.

“I won’t say that this isn’t your special talent because you did the submissive end of this during our first time. Maybe when you actually dominate somepony… it’ll appear. And as always, you can find me in the markets every now and then if you need to add more tools for your trade. I’d be more than happy to buy your time again.”

Sweetie Belle finally found her legs and stood up. “You were great. Thank you for helping us.”

Mr. Zebra’s warm smile seemed to radiate through the room. “Not at all. I thoroughly enjoyed myself. It’s not often that I don’t have to wear a condom, but your ponies have so many magical means of contraceptives that I guess it wasn’t necessary this time.”

Sweetie Belle’s face paled as her mouth dropped open in a big ‘O’.

“OH FUCK! I KNEW I FORGOT SOMETHING!”

Author's Note

I hope you enjoyed the story. If enough people want it, I might add an Epilogue later.