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.