Taking Care of the Crusaders

Scootaloo and Sweetie Belle heard the soft patter of Apple Blooms footsteps as she reached the top of the stairs and made her way to the room in which they stood. The two fillies approached the door, eagerly awaiting the story that Apple Bloom would tell.

“So, what happened, what happened?” Sweetie Belle said excitedly, jumping up and down as the door opened.

“A lot,” Apple Bloom replied with a smile, wiping her brow.

“Yeah, sure,” Scootaloo teased, giving her a smug wink. “You gave him a blowjob didn’t you?”

“Uh huh,” Apple Bloom said with a proud smile. “But something else happened before that.”

Sweetie Belle took a step even closer to the filly in the spotlight. “Something? Something like what?”

“Well, ah told him ah was gonna give him a blowjob and he said he wanted to do somethin for me first.”

“Oh?” Scootaloo asked, raising her eyebrow.

“Well, he played with mah marehood like he did with Sweetie Belle… but he used his tongue instead.” She blushed deeply and giggled. “He, uh, he made me cum.”

“Wait… what?” Sweetie Belle squeeled. “Fillies can do that too?”

“It’s different but yeah,” Scootaloo said with a nod, proud of her own knowledge. “And then what?” she asked, turning to Apple Bloom once more.

“Well, then ah gave him a blowjob. Ah sorta gagged a bit at first,” she said shamefully. “But he told me to relax and ah did. His stallionhood slid right down into my throat no problem. I sucked on it and used mah tongue and stuff too.”

“Did you swallow his cum?” Scootaloo asked curiously to which Apple Bloom nodded her head. “Good, cause spitters are quitters.”

“Huh?” Sweetie Belle asked.

“Ponies that don’t swallow stallion cum aren’t good at blowjobs,” Scootaloo explained, figuring she needed to dumb down the question for the innocent filly.

“ Ah didn’t get mah cutie mark though…” Apple Boom muttered, her lips quivering slightly.”

Sweetie Belle beamed. “Still worth it though, right?”

Apple Bloom smiled softly, her stomach fluttering. “ Yup… so now what’re you gonna do, Scootaloo?” Apple Bloom teased as she turned her attention to the pegasus. “Ah already gave him a blowjob.”

Scootaloo laughed. “It’s pretty simple. I’m gonna bang him.” The two fillies looked at her curiously and she sighed. “I’m gonna have sex with him. Real sex. He’s gonna put his stallionhood in my marehood and its gonna feel awesome.”

“Ouch,” Sweetie Belle replied with a grimace. “How is that going to fit inside you?”

“It stretches,” Scootaloo said smugly. “Besides, a little pain isn’t a bad thing.”

“It’s not?” Apple Bloom asked, chuckling to herself.

“Ugh,” Scootaloo sighed, smacking a hoof against her forehead. “You two just don’t get it. It’s not like it hurts that bad. It hurts just right.”

“Whatever you say,” Apple Bloom said in disbelief, giving the filly a halfhearted shrug. Scootaloo rolled her eyes before walking out of the room, her thoughts turning to the task before her.

***

Butterscotch was surprised at how eager he was to continue, how passionate he was for the next filly. He had always liked Scootaloo. She was a lot like his friend Blitz except much smaller and, of course, the opposite gender. He was sure such a cocky filly had something very fun in store for him, and she was a show off at that.

He noticed the rather cheesy and stupid grin growing upon his face as he heard her hooves against the stairs. He quickly wiped it away before she turned the corner and made her way towards him. All that was left of his grin was a half-hidden smirk.

“Um, hey there Scootaloo,” he said, struggling to hold back his grin as he smiled at the filly sweetly. “What-”

“Shut up,” the filly said with a rather amused smirk, even more amused than his own. “You know what I’m here for. I wanna give you even more than the girls. I actually know what I’m doing. Fuck my pussy, Butterscotch. I’m sure you want it, huh? Small, tight, juicy, just perfect for your big cock,” the filly cooed lovingly, turning and lifting her tail to show off her already dripping marehood. Although soft and tender like the other fillies, it seemed less tight, less innocent as if she had had another inside her before.

“H-how do you know so much about this? Will I even be able to fit my stallionhood inside you?” Butterscotch mumbled, growing nervous.

“Blitz and yeah, you’re pretty close to the same size as Blitz… well, maybe a bit bigger,” she said plainly, looking over her shoulder at him, still shaking her small plot.

“Y-y-you and Blitz…” he paused, letting out a gasp.

“Yeah, that’s how sibling who aren’t really siblings bond. What do you say, wanna be my new brother?”

“Uh… um… I don’t think that’s how it works but yes, I want you,” he muttered out, his face growing red.

“Oh don’t be so shy, ya baby,” she said, rolling her eyes teasingly as her smirk grew even wider. She easily hopped onto the couch, her wings flittering against her sides in excitement. “You wanna do the fucking or me?”

“I, um… well,”

“Me it is,” she said with a sigh, once again teasingly. “Lay down.” She looked at him with a mixture of determination, confidence, and excitement in her stormy purple eyes. She flicked her messy mane to one side of her face and gave him a seductive wink. Butterscotch trembled slightly and laid down, his back once again resting against the sofa’s arm. He shuddered excitedly at the thought of such a small filly having reign over a full grown stallion like himself. His cock, once again having never returned into the protection of its sheath, was growing hard.

With her wings still buzzing, the filly crawled on top of him. Butterscotch gasped as her marehood pushed down against his shaft, her lips cupping around its surface. She let out a soft moan as she began to thrust her hips, causing her small marehood to move up and down his shaft. Her insides glided easily across his skin, leaving a moist trail behind them. The fact that she was already wet meant that she was conditioned; her accounts of doing such things with Blitz had to be true. He knew Blitz enjoyed all things relating to the fun of sex but had never expected him to do so with a filly. Yet, he was doing it himself. In a way, it made him feel better about his actions, since his friend had done them already, but he knew that was no excuse. There was no stopping now. He had already gone so far and did not want to leave Scootaloo out. She would feel bad. He had created an even better excuse to continue.

“Hey, aren’t you enjoying this?” she asked with a huff, noticing the hazy, distant look in his eyes. This snapped him back into reality.

“Oh, yes of course,” he said sheepishly, shaking the thoughts from his mind. The feeling of her warm, wet pussy returned in full force causing him to moan. His cock flinched back into life, growing hard once more. Scootaloo smirked and pushed herself down harder onto his member, making herself moan as she ground her clitoris upon its hard surface.

“Mmm, yeah, you want to be inside me, huh?” Scootaloo cooed, drool dripping down her chin as her small, fit flanks slapped against his crotch. “You’re so big. It’s gonna be awesome.” Scootaloo seemed to be much more into the idea of what the two were about to do than Butterscotch. This made him feel anxious, nervous, yet even more turned on than he was before. The idea of a filly wanting him so badly for the plain enjoyment of sex was both daunting and exciting at the same time.

“Mhm,” he muttered, his face growing red. Even after what he had done with Sweetie Belle and Apple Bloom, he still had never had true sex. He would be losing his virginity to a filly who had already, oddly enough, lost hers before he had. He was glad to do so, knowing that the prideful pegasus would perform everything that she had learned and perhaps even more to show her prowess.

She raised up slightly upon her hind legs and tucked a hoof beneath her, grabbing his cock and holding it up into position. He moaned excitedly as she prodded her dripping marehood against it, barely letting any of his tip push inside her. “Blitz hates it when I do this,” she said with a chuckle. “I bet you do too, huh?” She did not need an answer, not that Butterscotch could give her one anyways. He was too busy groaning at the sensation upon his sensitive tip which eagerly awaited more. His face grew redder by the second, only inciting Scootaloo to tease him even further. “You have to tell me when that you want me,” she stated as plainly as she could without laughing. “Or else its not gonna happen. You want me, don’t you, Butterscotch? I’ve seen the way you look at me. Do you have fantasies about me? I bet you do.”

Butterscotch trembled with embarrassment. He had always thought Scootaloo was attractive with her tomboyish attitude and looks, even if he hated to admit it to himself, but on that night everything was different, everything had changed. “Y-yes…” he muttered out in a gasp. “I… I want you so bad, Scootaloo.”

“Heh, thought so,” Scootaloo teased, licking her lips. Biting her lip and buzzing her wings once more, she thrust downward and moaned painfully as she forced her tip in with a pop. With her whole body trembling, she pushed inch after inch inside her. Butterscotch moaned in bliss, his eyes rolling into the back of his head before falling shut. Her insides were so incredibly tight, squeezing each inch that made its way inside. They were dripping wet though, providing some ease for passage.

“Agh, feels so good,” the filly groaned loudly, saliva bubbling at her lips. “Hurts, but the good kind.”

Feeling something off, Butterscotch blinked his eyes open to see a small amount of Scootaloo’s blood dripping down his cock. “Oh… oh no, are you okay?” he asked fearfully, his eyes growing wide and his body freezing. Scootaloo looked down and then back to him, giving him a shrug.

“Just a bit of blood,” she said without concern. “Happens every time I do it with Blitz too. “Besides, I kinda like a bit of pain. Makes it feel that much more awesome.” Butterscotch shuddered, realizing how much Blitz had corrupted the filly’s mind. It was not like he could change that though. Telling her that it was not the smartest idea would only make her angry. Along with that, they had already gone too far too far to stop. At least he knew he did not want it to end. Though it seemed like Scootaloo did not either.

“…Okay,” he said somewhat hesitantly, letting out a sigh to help himself relax and enjoy himself once more. He watched almost fearfully as she pushed his member deeper and deeper inside of her, her insides seeming to grow tighter the further in he traveled. Saliva dripped from the sides of her mouth as she dug her hooves into his chest. He was sure he could see his cock pushing her stomach out from the inside, but it all seemed much too surreal. Perhaps, he thought, he was simply imagining things. She came to a sudden halt, letting out a short gasp. Butterscotch was unsure of whether it consisted of pain or pleasure. She had experience, and he could tell. Although she did not have all of his length inside her, she had still stopped, knowing when not to push it in too far.

“You ready for this?” she asked proudly, giving him a confident wink. He nodded his head softly and then moaned as pleasure pulsated through his lower half. Her incredibly snug tunnel moved up and down his shaft, wet enough to glide across it, but tight enough to tug and pull. Scootaloo moaned loudly, her eyes clamped shut as the smooth motions of her hips moved her back end up and down.

“Ah!” Butterscotch gasped in ecstasy, strands of saliva connecting the roof of his mouth to his tongue as it opened wide. Scootaloo’s confidence grew as she felt the stallion beneath her trembling at her actions, his hips thrusting and his legs gently kicking on occasion. Her eyes lazily opened and observed the nervous actions of Butterscotch’s shaking hooves. They were raised slightly away from the cushioning beneath them, hovering beside her flanks.

“You can touch all you want. You’re way too polite sometimes, ya know that?” she huffed, almost in anger.

“Oh… okay,” he muttered beneath his breath and gently clasped the small flanks in his hooves. He knew Scootaloo was an active filly, but was surprised to find how much it did for her young body. Her flanks were much tighter than the previous fillies’, well rounded with developing muscle. Although not as pillow-esque as the previous flanks he had so lovingly massaged, he did find their perfect curves and strong muscles more than pleasing.

“Squeeze harder, you wimp,” Scootaloo teased, grinding her hips more lovingly against his cock. He did as she asked, pushing her tight flanks together with his hooves and deeply massaging their surface. “Uh huh, that’s better,” she groaned in pleasure. Butterscotch noticed her movements growing faster and more fluid. He could tell she was getting even wetter and that her passage was loosening ever so slightly. It had loosened enough that she could move her way over his sensitive tip, causing it to flinch and pleasure to rush down his shaft before easily sliding her way back over its wider surface, allowing smooth re-entrance.

His eyes moved their way from her flanks to her inner crotch, watching the stretched lips of her marehood glide up and down his cock. Upon his cock was a pinkish mixture of her leftover blood and ever increasing juices, bubbled slightly from her quick movements. Too entranced by the sight before him, Butterscotch barely noticed the movement of his hooves upon Scootaloo’s flanks, slowly moving inward. It was not until he felt the soft but wrinkled skin of her tight anus that he froze, his face growing red.

“Like plotholes, huh?” the filly asked with a smirk. “Ya know…” she said with a teasingly sheepish look upon her face. “I’ve never been fucked there before, and I really want to try it.”

“You, you do?” Butterscotch mumbled, his lips trembling at the thought.

“Uh huh? Wanna be my first?” Butterscotch could tell that such a thought excited her, her motions growing even faster and harsher. He groaned at the pleasurable sensation, his hooves massaging her hole more vigorously.

“Y…ye….yes,” he managed to let out between heavy pants.

“Agh,” Scootaloo grunted blissfully, her body trembling violently before it tensed. She let out a long moan as her juices splattered out over his cock and onto his crotch. “Mmm…mmm,” she muttered weakly as she finished, biting down hard upon her lower lip. “I…I came before you did…” she said, blushing lightly in embarrassment. “Blitz always finishes before me,” she huffed. “You’re good, better than I thought you would be at least.” Butterscotch nodded his head and smiled softly at the compliment. He could have explained that after already having orgasms with Sweetie Belle and Apple Bloom, it would take longer for him to do so again, but figured there would be no harm in not telling. “Bet you can’t last until I cum again though, huh?” she teased, her confidence returning. “Unless anal makes it quicker or something. I don’t know, never tried it like I said… let’s do it,” she said in a burst of excitement.

Butterscotch gasped slightly as she pulled her dripping marehood away from his cock, her juices trickling down his shaft. She weakly rolled over onto her stomach and raised her backside into the air. Lifting her tail, she revealed the mess upon and around her marehood, her fur glistening wet in the light of the room. Above it was the tight entrance of her anus, completely untouched and innocent besides the few moments of massage Butterscotch had provided for it. “Take over,” the young filly commanded, gently shaking her perfect flanks. “I want you to rut me good.”

“I, um, well,” Butterscotch muttered, not expecting to be forced into taking the lead with such a brash pony like Scootaloo.

“C’mon… do it,” she said with impatient sigh. Even if he was taking the reins, Scootaloo was certainly still in charge.

“Y-yes, okay,” he mumbled nervously as he shakily crawled over top of her. He quickly realized how awkward the position would be considering he could not use her body for any form of support since his easily engulfed hers. He would not admit it though. She was stubborn and would not be willing to change her position anyways. He curved his head downward, awkwardly looking over Scootaloo’s messy mane to determine the position of his cock and where it needed to go.

“Why are you taking so long?” she grumbled, her eyes darting up to his own.

“J-just… hold on,” he muttered in embarrassment, sweat beading up upon his forehead. He moved a hoof down between the two of them and shakily grabbed his cock, positioning it where he hoped her entrance was. He leaned in slightly and prodded, feeling only fur.

“Uh… what are you doing?” the filly asked impatiently.

“I...I can’t see where I’m going,” he muttered.

“To the left…” she said with a sigh. He did as she asked, slightly positioning his cock more to the left. This time his cock pressed into her marehood, causing her to moan slightly.

“W-wrong hole,” she grunted. He sighed shakily and pulled away, moving his cock upward. Finally, after what to him seemed like minutes of awkward confusion, his tip prodded against her wrinkled entrance. He pushed slightly harder but nothing happened. This hole was much tighter compared to her marehood, pressing back against his cock with equal force, not easing for any sort of entrance.

“Harder,” Scootaloo grunted, her face growing red at the strange sensation. He did as she asked but still nothing came of it. “Come on, you can do better than that.” With another nervous sigh, his eyes fell shut and he thrust his cock forward at lightning speed, pressing it harshly against the tight hole. The two gasped in unison as his tip suddenly popped inside, the force of his thrust causing another inch or so to make its way inside of her. “Nnngh, it hurts,” Scootaloo groaned, spit sputtering from her mouth.

“Do you want me to stop?” he asked in fright, his body freezing.

“Of course not, stupid. Just… just start slow.”

Butterscotch could not stop himself from grunting as the tunnel before him squeezed tightly around his shaft, even tighter as he attempted to push in further. He was amazed by how much force he still had to put into his hips to make any kind of progress. She felt amazing, it was as if he was already going to orgasm at any second, the tightness of her hole attempting to milk him dry. With his stomach resting upon her back, his grunts vibrated through her body and she watched as his front hooves shook before her. She too grunted at the unnatural sensation. It felt as if nothing was supposed to be inside her in such a way, so much so that her body seemed to be fighting against it. At the same time, it felt good, like the good kind of pain she felt in her marehood except much more extreme. She both craved more and wanted it to end. The deeper he went, it seemed, the larger the pleasure grew. She wondered how deep he could go but worried of its consequences.

Butterscotch was once again surprised, this time by how deep he could go, inch after inch of his cock pushed its way inside her with fairly good amount of ease if the tightness was not taken into account. He moaned at the sensation of his length being squeezed tighter and tighter the more he pushed in. Scootaloo let out a soft sigh, growing somewhat more comfortable with the feeling and immediately noticed the sudden ease of tension in her backside. Butterscotch noticed as well, his cock slipping inside her more easily. It was not long before all of his length had made its way inside the filly’s tiny hole. “Wow…” he muttered.

“Huh?” she asked turning her eyes up at him once more.

“You did it… you fit all of me in you.”

“I did? I… I mean, yeah of course. I totally could have done that with my marehood too. I just didn’t want to.” She blushed lightly and smiled proudly, more to herself than him.

“Still want me to go slow?” he asked as he began sliding his cock back out. Scootaloo’s face contorted at the sudden, seemingly much quicker redaction.

“Y-yeah,” she muttered, trembling slightly. Not wanting to slip out and repeat the same awkward process he had when he started, he began pushing back in long before his tip returned to her entrance. Scootaloo grunted, this time with pure pleasure. “It… it feels good,” she said excitedly, surprised by the sudden change. Her legs trembled and she could feel her marehood growing wet once more. “Really good. Go faster now… just a little.” Butterscotch nodded his head and smiled down at her as he repeated his motions, this time only slightly faster. He could tell that his motions were still not fluid and hoped that it did not bother the filly; it was his first time after all. Maybe once he grew used to the motions, it would become easier, he thought.

After a few of his slow, pumping motions, Scootaloo once again encouraged him to go faster. Due to the eagerness in her tone, he did not hesitate to increase his speed. With the quickened pace, his motions did indeed seem to grow more normal. Her insides seemed to be growing used to his cock as well, giving way much more easily to its girth and length than it had previously. This allowed him to thrust even more quickly and smoothly.

Scootaloo moaned and groaned in passion, drool once again dribbling from her chin. Perhaps the sensation of his stallionhood rubbing, pulling, and stretching at the insides of her rectum felt even more pleasurable than when it was inside of her marehood. The sensation of his weight pushing down against her small body with each of his thrusts added to the pleasure. She felt as if she was a toy being used for his enjoyment, and for some odd reason, it turned her on, even if she did not understand it. “Harder,” she grunted beneath her breath. “I want more!”

Butterscotch nodded his head in agreement, even though her eyes were clamped tightly shut. Her legs collapsed beneath her with the force of his thrusts, compelling him to fall forward as well, nearly crushing the filly beneath his weight. He knew it was exactly what she wanted and that he could not stop until he was finished. Scootaloo groaned loudly as his cock slammed deep into her canal, his balls slapping against her marehood. She could feel her body growing numb, the only feeling, growing more extreme, was in her backside and one of her hooves. It forced its way beneath her, instinctually cupping around her marehood. Her groans turned into loving moans as she rubbed it in a circular motion, her juices gushing out from between her lips.

Butterscotch’s cock tickled with pleasure and the muscles in his legs and flanks began to tighten with each of his thrusts. His moans grew as loud as Scootaloo’s as the tickle turned into a fierce rush of pleasure. His motions grew even harsher, pushing the weak filly’s body into the cushions as he continued to rut her tiny hole. “I’m going to… mmmpf,” Butterscotch groaned, clenching his teeth together as his legs trembled once the pleasure grew even more intense.

“Me too!” Scootaloo gasped beneath her breath, her hoof creating a sloshing noise as it glided effortlessly up and down her slit. Butterscotch’s eyes grew wide as her insides suddenly clenched even more tightly around his cock as her hot juices splattered out onto his crotch. Scootaloo gasped as she felt his cock pulsate violently inside her tightened rectum and his warm seed expelled into its depth. She could feel her hole quickly filling up and grunted as his cum began to spurt out from between her anus and his shaft. Butterscotch pulled out with a heavy pant and the filly sighed lovingly as his thick goo emptied out of her and onto the couch.

“Oh….oh, wow,” Butterscotch sighed, struggling to stand in an attempt to free her. She sighed once more as she rolled over onto her back, a large, content grin upon her face.

“That was… awesome!” she gasped, looking up at him with sparkling eyes. He looked down at her wet, engorged marehood and the wide gaping hole beneath it and smiled, turning his eyes back up to her.

“Oh, yes. You felt absolutely amazing.”

“Yeah, I knew I would,” she said with a wink, her cheeks growing pink.

“Now… I have to ask you something very important,” Butterscotch muttered shyly, his face growing red.

“Huh… what?” she asked, raising an eyebrow.

“Please don’t tell anypony about this besides Apple Bloom and Sweetie Belle, okay?”

“Yeah, no problem. I did the same for Blitz so, ya know, I have experience.”

“Good…actually,” Butterscotch said with a smirk. “I guess maybe you could tell Blitz too. I’m sure he’d be jealous.

“Heh, yeah a bet,” the filly said with a giggle. “He’s never made me cum twice in one go before.”

Butterscotch chuckled. “Exactly. Anyways, I think we’re all going to need a bath tonight. How about you and the girls get ready, and I’ll be up in a minute to see if you need any help with the water, okay?”

“Okay,” she said with a smile before rolling over onto her stomach and then hopping down onto the floor. He watched in embarrassment as the filly waddled away, her legs wide and weak from what he had done to her. Her tight flanks were still as blank as they had been before.

“It looks like you didn’t get your cutie mark,” he said in an empathetic tone.

“Yeah,” she said, turning to him with a smirk, “didn’t think I would. I just wanted to have some fun.” He smiled in response and continued to watch her perfect flanks flex with her movement as she made her way to the stairs.

Butterscotch sat up and rested his head against the back of the sofa while letting out a sigh, one of both exhaustion and joy. The thoughts of each of the adorable fillies and what they had done together that night rushed through his mind. It would be a night he would remember for the rest of his life, whether that be because of regret for preforming such immoral actions with fillies so young, or because it had to be the best experience he had ever had. He also knew that such an experience, no matter how much it excited him, could never be spoken of around any pony besides the three fillies, of course, and perhaps Blitz who seemed to have the same interests. For the time being, he was grateful to have been able to experience the wonders of sex with such cute ponies and that he was brave enough not to back away.

***

Elusive planted three gentle knocks upon the door of Butterscotch’s cottage, its wooden surface glowing in the morning sun and birds chirping in the surrounding trees. To his surprise, the door opened immediately, the three smiling fillies standing in neat row, Butterscotch behind them, his eyes covered by his mane.

“So, how was your night?” Elusive asked, the fillies acting eerily polite and overjoyed.

“It was good,” Apple Bloom replied.

“Alright,” Scootaloo corrected with a rather fake shrug.

“What did you end up doing? You didn’t worry or bother Butterscotch too much with your ‘crusading,’ did you? Were you trying for anything specific this time?” Elusive questioned, giving Butterscotch a smile.

“Um… well,” he muttered nervously.

“We…. were… wrestling?” Sweetie Belle said with a sheepish smile.

“Yup, we were trying to get our cutie marks in wrestlin’,” Apple Bloom confirmed with a nod. The fillies all nodded their head in unison with Butterscotch smiling nervously in the background.

“Ugh,” Elusive revolted with a grimace. “How uncivilized. I’m certainly glad you didn’t get them. Anyhow, I have to get back to a new order, so let’s hurry you girls home, shall we?” Butterscotch chuckled beneath his breath while his heart pounded. He was sure his friend would be much more disgusted if he knew what the “wrestling” consisted of.