The Twilight Sparkle Scholarship Program
Chapter Five: The BBBFF Bachelor Party
-by Drace Domino

A few weeks after their partnership began, Twilight Sparkle and Sugarcoat were at the top of their game. With Twilight Sparkle’s attention to detail, Sugarcoat’s upfront business practices, and both girls firmly focused on making as much money as possible their profits had soared to a point that neither one could have achieved on their own. With every last dollar sent to a shared account that would require both of their signatures to withdraw from, the two had begun a lewd little enterprise that was sure to pay for the college of their choice when the time finally came.

And business was only getting better.

“All right, the payment just went through. We can go inside now.” Sugarcoat spoke from the driver’s seat of her parked car, sitting just outside an apartment complex. She tapped on her phone to finalize the transfer, and as she tucked it into her pocket she gazed over to Twilight with her typical sharp gaze. “Just remember, they only paid for us to show up and fuck them. If they want us to be nice about it, then the tips have to come flying.”

“You don’t think I’d forget that, do you?” Twilight responded with a slight chuckle, and together the two girls started to slip out of the car. They were both dressed in their Crystal Prep uniforms - a favored choice among their clients - complete with pleated skirts, kneehigh socks, vests, and glasses perched upon both of their faces. They looked intensely innocent as they padded their way to the apartment complex, so much so that it’d be hard to imagine that in reality they were a pair of prostitutes heading towards a big score. As they walked Twilight gazed over to Sugarcoat once more and scrunched her nose up, murmuring as they made their way in the front door.

“This place looks familiar.” She murmured to herself. “I could’ve sworn I’ve been here before. What’s the event, again?”

“A bachelor party.” Sugarcoat offered simply, before rolling her eyes. “Well, an early bachelor party. The wedding isn’t for a while, but they wanted to get the jump on it because they’re horny perverts.” She shrugged. “Whatever. If we do a good job, that just means they’ll hire us again when the wedding’s closer...and that time, we can jack up our prices!” It was that business acumen that solidified Sugarcoat’s contribution to the team - the keen eyes always looking to help them make the most. Twilight Sparkle smiled and gave a little nod as the two continued to make their way up, standing silently in the elevator with no small talk. As they made their way to the front door where the job was waiting Twilight’s hands moved up her body to do one last check - business cards were in her pocket, a change of panties were tucked away so it wasn’t a sticky ride home, and most important of all her wallet was nowhere to be seen. Her purse was tucked safely away in the trunk of Sugarcoat’s car, because after all...anonymity was important in their line of work.

When she gave Sugarcoat a little nod to knock, the two girls weren’t left waiting for long. Past the blaring music and the sound of a few dudes just hanging out waiting for their whores to arrive, the door finally started to open and they faced a small crew of young men not much older than them. One of them - a white-skinned, blue-haired young man with a stunned look on his face, was the first to speak.

“Twily?!”

To say that things were awkward upon realizing it was Shining Armor’s bachelor party would have been an understatement. Twilight Sparkle would’ve just turned and left right then and there, but as Sugarcoat was quick to point out the payment had already been processed and there was never any refunds. Still, as the two girls stepped inside Twilight Sparkle couldn’t help but avert her eyes away from her brother and drift towards his five friends that were all there to celebrate with him.

“So, whose apartment is it?” Sugarcoat was the only one to speak with any boldness in that moment, with the two siblings understandable awkward and the other guys a bit unsure how this would unfold. When one of Shining Armor’s friends raised a hand the girl with silver hair and glasses gave a short nod and pointed towards the living room. “You’re going to pull that chair away from the couch. I’ll take care of Twilight’s brother and she can handle all of you guys. Does that sound fair to everyone?”

“Uh...I mean…”

“Look.” Sugarcoat gave a tiny snort, and folded her arms across her chest. She stepped up to where Shining Armor was still trying to keep his eyes on the floor, and looped an arm through his. Her words came fast and focused, since clearly she was the only one qualified to take the lead at such a tender moment. “We could stand around marvelling at how strange a coincidence this is, or we can fuck. The five of you will have plenty of fun with Twilight, and I’ll make sure the star bachelor goes home happy. The only thing I want to make perfectly clear is this-” She raised a pointed finger, and twitched her nose a bit. “You boys are on the clock and we’re both leaving exactly at six. So what’s it going to be?”

With a stern, solid argument like that it was hard for anyone involved to complain. The guys had already paid for the services of the pair of whores, and though they might be disappointed that none of them would get the blowjob sandwich treatment with the two spread out, one purple teenage pussy was better than none. Finally they all nodded and Twilight Sparkle gave her own noise of agreement - fucking five guys was definitely more than her fair share of the workload, but it was worth it for having Sugarcoat take care of Shining Armor. As the crowd moved to the living room, Twilight Sparkle stretched out a hand to take Sugarcoat’s elbow, pulling her in to whisper something short and soft.

“Sugarcoat?” She asked. “Take one hundred dollars off of my share, treat it as a tip from him. Make sure my brother has fun, okay?” Sugarcoat merely smiled and nodded. And just to make sure things continued to be awkward, her voice rang out as she kept pushing Shining Armor forward.

“C’mon, stud, your sister just bought you a deepthroat.”

It was going to be a strange evening.

With the unexpected brother and sister reunion, they had already dipped a little far into the minutes the boys had purchased. As such, the girls skipped over the usual striptease to get right down to business - inviting their respective clients to come at them through their clothes. Sugarcoat pushed Shining Armor into the chair and slid right atop him, grinding her hips back and forth to slide her panties over his lap, all while brushing her palms across his solid, broad chest. Twilight Sparkle, on the other hand, was soon surrounded by boys on all sides. Sitting in the center of the couch, the girl could feel hands groping at her from every angle and it wasn’t long until she caught sight of cocks falling forward and offered up to her face.

“You’re the cuter one, anyway!” One of the guys rationalized it - he might not get to fuck Sugarcoat, but Twilight was a totally fine catch. As the tip of his prick smeared back and forth over Twilight’s cheek, he drew a glistening line of precum across her soft, warm flesh. “Guess we lucked out!”

“Nice seeing you again, Twilight.” One of the boys spoke with a grin, just as he slipped a hand underneath Twilight’s skirt and pressed his fingers against her panties. As he rolled them in a slow and teasing touch her thighs spread a little further, and she gazed up at him with blushing, cute features. It was one of Shining Armor’s friends - the owner of the apartment - and the reason it looked familiar to her as they made their way up. “I’ve wanted to fuck you for years. Can’t believe all I ever had to do was pay you!”

“We...We brought...business cards if you’d like to see us again.” Twilight bit down on her bottom lip, and pushed her hips forward to grind her nethers to that touch. Soon she was reaching up to cradle two cocks in her hands, and alternating her head from side to side to give each one a few tiny, sweet kisses. “We’re always happy to work with hot young guys like you…”

A bit of flattery never hurt. Soon Twilight Sparkle felt her panties pull free, and her pussy and mouth were wrapped around similar thick, eager lengths that weren’t in the mood to wait around. If the boys only had the girls for a few hours, then it was important to make every moment count! As she sat back on the couch Twilight hitched her legs around the waist of Shining Armor’s friend, and as he pounded her with slow and steady thrusts she continued to service every dick offered to her mouth. When she could see across the room in between the sea of horny young men her eyes darted over to Sugarcoat and Shining Armor - and though she wouldn’t openly admit it, the sight of it made the evening just a bit more exciting and fun.

The girls had only ever been in the business for the money. The orgasms were usually rare, and never what they were after. Still, as Twilight watched with widening eyes, she could already tell...this would be a job that made her cum, if for no other reason than watching her business partner ride her brother made her skin crawl with delight.

“How’s that teenage pussy?” Sugarcoat cooed, at this point with her vest undone, her bra unhooked, and her breasts left exposed before Shining Armor’s face. Similarly, her panties were dangling from an ankle and her skirt was pulled to her waist, leaving her slit exposed atop Shining Armor’s lap. For the moment she was just teasing him, keeping his cock pressed flat to his lap as she rocked back and forth across the shaft, leaving it glistening from her nectar as he pooled precum at the tip. With her hands moving into his hair she just kept rocking back and forth, her smile widening as her eyes narrowed behind her glasses. “Nice and warm? Think it’s warmer than your sister’s?”

“C...Can we...not talk about Twily?” Shining Armor murmured, his voice half-muffled and gasping. His hands were locked fiercely against the sides of the chair as his knees spread wide, and every breath he took was heavy and deep and quivering with excitement. His cock was rock hard and trapped underneath a sweetly warm embrace, though it seemed like Sugarcoat was just intent on teasing him before finally delivering true pleasure. “It’s...it’s really weird to find out that she’s...she’s…”

“She’s a whore.” Sugarcoat purred in her no-nonsense fashion, and grinded her hips against him all the harder. Soon she was leaning in, whispering against his throat, giving him a few tiny licks, and even clawing her nails down his chest. Anything to make him squirm all the harder. “Your little sister...is a whore. And right now, all your friends are running a train on her. And I’ll tell you one more thing-” She let her mouth drift up so she could whisper against the edge of his ear. “-she’s probably thinking about fucking you while they do it.”

Shining Armor’s gasp came at the same moment that his hips bucked back, and his cock finally slipped into position. By the time his muscles untensed his prick eased itself into Sugarcoat’s slit - pushing deep within those tight, warm, inviting walls and plunging down to the hilt. The schoolgirl gave a slightly mocking giggle as she felt her nethers spread around him, and she teased at his hair in playful fashion before offering him one last whisper.

“That sure got you going.” She murmured, and began to roll her hips. “You can watch her get gangbanged while you fuck me. I won’t be offended. We’re both here to get used...in whatever way makes you happy.”

Sugarcoat deeply cared about client satisfaction. Without waiting for Shining Armor to respond she began to rock her hips quicker and quicker, letting his length slip to very nearly the exit of her nethers before plunging right back down again. Twilight’s brother was particularly well-endowed and the trip up and down was a bit of a strain on Sugarcoat’s relatively slender frame - something she could no doubt tease her coworker about later on in the evening. Like Twilight, her climaxes during working hours weren’t particularly common, but she was already expecting that the blue-haired stud would be able to squeeze one out of her. If nothing else, she enjoyed seeing Twilight squirm in his presence.

As Sugarcoat continued to ride, Twilight Sparkle had finally been pushed into a position where she could watch relatively unfettered. By now, the guys had found the joy of filling both of her lower holes with cock and one of them laid flat on the couch as she straddled him. Another slipped behind her to ease his prick deep into her purple ass, and together they were pistoning in and out as the other three took turns with Twilight’s hands and mouth. The studious young woman was working diligently, rocking into the thrusts that she received and tending well to the cocks offered to her face - but it was obvious to anyone that she was a bit distracted. Her eyes kept dashing to where Sugarcoat was riding her brother with increasing intensity, clawing at his shoulders, pulling his hair, and making more of a show of it than usual.

To the group of guys that they were surrounded by, it seemed just like a whore enjoying herself. Twilight Sparkle knew better. After so many weeks working with Sugarcoat, she knew the girl’s reactions - and she knew that it wasn’t in Sugarcoat’s nature to put on a show unless she had a good reason. It could’ve possibly been the extra tip that Twilight offered her to make sure Shining Armor had a good time...or much more likely, it was all for her benefit. A professional courtesy, as it was.

“Yes, yes! Jam that big, hard cock into my pussy!” Sugarcoat’s voice was rising harder and higher into the air, something that wasn’t common practice for her under any circumstances. Most of the time, she had a tendency to merely glare at the guy fucking her and patiently wait for him to finish. But tonight...tonight, she seemed a damn sight more enthusiastic. “Mmmmn, that big cock is stretching me so good! Fuck, fuck, fuck! Pull my pigtails! Choke me! Do whatever you want to your little cocksleeve...big brother!”

The words came just as two of the guys Twilight was servicing did - and she was left gasping and staggered as one boy pumped her ass with cum as another was left squirting on her cheek. She was so stunned by Sugarcoat’s words that she almost forgot she was holding a squirting dick, and it took her a few seconds before slipping her mouth around it and starting her usual process of cleaning and swallowing every last drop. The words that Sugarcoat was unleashing seemed to go over the heads of most of the other guys, but certainly didn’t meet that fate with Twilight...or with the big brother Sugarcoat was calling out to.

She was making it easy for Shining Armor to envision that it was her. She was encouraging this madness for no other reason than her own enjoyment. Not that it was particularly strange for the Crystal Prep girl to do something teasingly mean just to entertain herself, but Twilight was already deciding that the two of them had to have a discussion about her professionalism once the night was over!

The evening went on like that well past five-thirty. With only a half hour left on the clock the guys continued to use their respective sluts, and the entire time Twilight Sparkle found herself unable to peel her eyes away from the sight of Sugarcoat fucking her brother. It was a testament to the skills she had learned in her past few slutty months that she was able to satisfy five guys even while distracted - she had become a consummate professional that could multitask like no other. As the boys lined up to stake their claim in her pussy, ass, or mouth Twilight Sparkle took swift care of them. Her motions were skilled and deft but not particularly passionate - there was no affection in any of her touches, and every motion came from a desire to get them off and complete their transaction.

No one was complaining. The nice thing about the grip of a wet teenage purple pussy was that it didn’t particularly matter if it was wrapped around a stiff cock for pleasure or for profit - and the guys didn’t mind as they pumped her with load after load after load. From time to time Twilight could feel one of them stuff a few dollars into one of the pockets of her schoolgirl outfit or against the band of her knee-socks, giving her a little extra for the hard work she was doing. When her head was dipped over the edge of the couch and she received reverse facefuck after reverse facefuck, they simply tossed their money onto her body where she scooped it up and embraced it, all while letting them use her throat with reckless abandon.

And the whole time - through spit-smeared glasses and with blushing cheeks, she watched Sugarcoat fuck her brother. Shining Armor’s naked figure was impressive and fit, and by that point even Sugarcoat had been stripped out of her schoolgirl skirt in a way that Twilight hadn’t been. Twilight watched the girl ride her brother before getting bent over the back of the chair, and then deliver to him the thrilling, wet deepthroat that she promised. Shining Armor wasn’t sparing her any breaks, either, making sure that he got his friend’s money worth by pounding her again and again. The only breathers he took were the brief moments after flooding Sugarcoat’s pussy or ass where he would scoop the girl into his lap, finger her cum-filled folds, and take a few seconds to get hard enough to plow her again.

And on more than one occasion, while Twilight’s head was dangling upside down and her throat was filled to the point of gagging on cock, she caught her her brother’s eyes. The two gazed at each other even as they fucked other people, and their excitement only burned hotter for it. When Shining Armor finally came with his cock lodged deep into Sugarcoat’s pussy, his eyes were utterly transfixed on Twilight’s - and as he squirted round after round into one girl’s purple pussy, there was no doubt on anyone’s mind that he was pretending it was another’s. When Sugarcoat lifted up off his lap she even made sure to lean forward, pressing her chest to Shining Armor’s face, holding her rump in the air, and spreading her pussy so Twilight could take a long look at the dollop of cum that was slowly, steadily oozing out. Twilight Sparkle, with a pathetic and aroused look on her face, could only gaze ahead and continue allowing her throat to be rammed.

It was a mere five minutes before six that the guys finally finished - or at least, recognized that they wouldn’t be able to get it up in time for another round. As four of the extras stood up and staggered around for their clothing, Shining Armor’s friend that rented the apartment looked to the bachelor and offered him a little chuckle.

“Hey, Shining, I’m gonna...uh…” He gestured to his bedroom. “Gonna hang out in there for a while when the guys leave. If you need to, y’know…” A quick glance to where Twilight Sparkle was sitting half-naked on the couch, dripping with cum from every hole. “...have a talk?”

“Thanks.” Came the young man’s response, and Shining slumped back into the chair with a soft grunt. In the filthy aftermath of the whores’ visit, Shining Armor and Twilight Sparkle sat across the room from one another - the only two that weren’t getting dressed or tidying up. One by one Shining’s friends excused themselves and slinked out of the room until only the bachelor and the two sluts were left, and between the three of them only Sugarcoat saw fit to speak.

“Heh, that was a pretty profitable run.” She beamed, reaching a hand over to Twilight and plucking one of the twenties that was stuffed against the hem of her kneesocks. She was slipping every lightly cum-covered bill into a plastic bag to be cleaned and cashed in later, and was humming lightly to herself as she worked. “Your brother’s friends must’ve given you almost four hundred in tips. Good job...Twily.”

A staggered and gasping Twilight Sparkle looked up to her coworker, tried to form a response, but utterly failed. So many months ago, Twilight had taken up the task of sucking dick for profit...and it was this particular day that she met her first true hurdle. She and her brother had seen more of each other than they ever would’ve guessed, and now Twilight Sparkle was at a crossroads: was the money worth the slut she was becoming?

The answer, as her eyes tracked the baggy filled with bills held by Sugarcoat, was a resounding yes. College wasn’t cheap, after all!

“Did...did you…” She blinked, and gazed up at her coworker. “...give them our business cards?”

“What? I totally forgot!” The look of irritation that crossed Sugarcoat’s face was immediate, and she threw the bag of bills towards the other whore. As she scrambled to the door she snatched up her school vest and threw it over her otherwise bare chest, hoping to chase them down in the hall before they got too far. “Guys! Hey boys, wait up!”

The door opened, slammed, and left Twilight and Shining Armor all alone in a room with an intense, heavy fuckstench in the air. Twilight Sparkle, cum-soaked, sweat-licked, and with dishevelled hair and askew glasses. And Shining Armor, sitting with his cock standing upright, stiff, and still hard as ever. The two gazed at each other once more, until finally Twilight Sparkle offered a tiny grunt as she started to stand up from the couch.

“Shining, listen…” She began, half-wobbling on shaky knees. She did just finish letting five guys gangbang her, after all. “Please, don’t tell Mom and Dad about this, I’m trying to make money for college, an--”

“Twily, if you think I’m going to tell anybody about the past two hours, you’re out of your mind.” Came her big brother’s honest and flat response. “I’m getting married in a few months. Don’t you think my fiance would have some...thoughts about my friends hiring hookers to celebrate?”

“Oh. That...makes sense.” Twilight Sparkle murmured, nibbled once more on her bottom lip, and rocked back and forth on her heels. It was undeniable that the two siblings had been watching each other - and Twilight was still left shivering from a few idle orgasms, climaxes that she likely never would have had if it wasn’t for her brother’s presence. The job had been finished, the profit was made, and there was one last chance for Twilight Sparkle to go even further than she ever had before. A chance she was happy to take. “So...uh...since we’re agreed we’re not telling anybody…how about one last blowjob?”

And there it was - the offer that both siblings knew would come up sooner or later. Shining Armor stretched his hand out to his discarded jeans, rummaged through one of the pockets, and pulled out a small bundle of bills. As he held them up Twilight started to advance, her eyes tracing the offering.

“I’ve only got forty-five bucks left.” He offered, and gave his little sister a smile. “Good enough…?”

“Well...we’ll call it the family discount.” Came Twilight’s response, and she plucked the money from her brother’s fingers. After tucking it against her sock the nearly naked young woman slithered down to her knees, moving to do something she had never imagined performing in the past. Shining Armor’s cock was standing upright and bold, glistening not just with his own cum but with Sugarcoat’s leftover nectar. Indeed, Twilight could smell her coworker still lingering on her brother, and it was with a deep, savoring breath that the girl leaned forward to begin tending to it. Her hands pressed to the sides, her lips teased the tip before gliding down the first inch, and her tongue slithered out to glide under his cockhead and start drawing in long, lewd tastes of his flavor.

“Hnn...Twily…” Shining Armor’s hips rose from the seat, and he allowed a hand to stretch forward into his sister’s hair. With how far things had already gone there seemed to be no harm in letting another few inches of his member slide inside, rubbing back and forth across an eager little tongue that was earning the money spent on it. With a heavy blush running across his cheeks Shining Armor unleashed a low and throaty groan, with his fingers passing through his little sister’s locks. “T...This...this all between us…”

Thankfully, discretion was part of the package when someone hired Twilight and Sugarcoat. The girl braced herself against the chair and gave her brother the deep throated blowjob that he deserved, taking the time to please and service him in a fashion that she hoped, truly, that Cadance would one day do. After all, nothing but the best for her brother! Wasn’t it every little sister’s wish that her big brother would find someone that sucked dick as good as she did?

The sounds filling the room were wet and messy, brought forth from Twilight’s hungrily slurping mouth and the squeeze of soaked fingers around his shaft. When she popped her mouth from his prick it was only so she could lower her head to service his sack, licking back and forth across his balls as she gazed up across his fit, firm figure. All the while her hand continued to pound him off within her grasp, and from time to time she even threw in a few “big brother” or “BBBFF” comments to remind him of the depths they had gone to.

From Twilight’s perspective, the excitement of sucking her brother off was immense...and her cum-filled pussy was trembling in delight. But what she hadn’t expected was how much she enjoyed the flavor that coated him, the nectar left by her coworker in generous, slathering glee. Sugarcoat’s pussy had left Shining Armor’s well-used cock absolutely covered from tip to base, and Twilight Sparkle was hungrily licking away every last inch of flavor. A taste that was familiar to her over the course of the past few weeks to be sure - but a taste she was similarly building a very strong fondness for.

“T...Twily...I’m going to…” Shining Armor tensed up all the harder when the door finally opened and Sugarcoat returned, walking in counting a small bundle of bills and still wearing only her cumstained panties and her school vest. Apparently, the boys had given her a tip in return for her business card - or judging by the fresh cream in her hair, for letting them quickly jerk off on her. Shining Armor’s eyes dashed to the other student before back to his little sister, and his cock started to unload with one last, furious grunt. “Hnnn…!”

Sugarcoat’s smile was enormous while she watched, studying Twilight Sparkle as her coworker locked lips around her brother’s cock and drank straight from the tip. Her throat bulged and rolled as she swallowed load after load of his cream, her eyes wide behind her glasses and her hands firmly nestled between her thighs. She was playing with herself in a way that Sugarcoat hadn’t seen her do before - at least not while on the job. When Shining’s cock was finished it popped from Twilight’s lips with a smack, and already the boy was standing to his feet and stammering as he looked at the two.

“I...I...thanks, Twily, I should...uh…” He glanced between the two girls before practically stumbling towards the restroom, his cheeks blushing vibrantly. “I should...get dressed! I’ll be right back! Or...if you have to go, feel free!”

Shining Armor’s escape after cumming in his little sister’s mouth was hardly graceful, but in all fairness it was likely a tricky thing for the boy to cope with. He was probably a virgin until Sugarcoat, after all. Twilight Sparkle watched him go with a lingering taste of her brother’s cum on her tongue, not looking up until Sugarcoat stood beside her and lightly draped her fingers atop her head.

“Hey, Twilight.” Sugarcoat smirked, and quirked a brow. “Ready to go?”

“...ready.” Twilight responded simply, and slowly pushed herself up to her feet. Just like that, the two girls put the events of the past two hours behind them - it was just business, after all. Soon they were dressed in their schoolgirl outfits in their entirety once more, complete with the fresh and dry panties and a ziplock baggy filled with cash. As they made their way back down the hall Twilight couldn’t help but gaze at her coworker, and with a soft grunt finally found herself asking a subject that had been nagging at her mind.

“Hey.” She offered, curiously. “How was my brother? Did you have a good time fucking him?”

“He’s all right.” Sugarcoat shrugged, and pressed the elevator call button. While they waited she leaned against the wall, and straightened out the sticky pleats of her skirt. “Probably my second favorite fuck in the family.”

Twilight Sparkle merely smiled and even blushed, and patiently waited as the door opened and Sugarcoat slipped inside. Another thought struck her a split second later, and she called out while giving chase to her coworker and friend.

“Wait, we’re the only ones you’ve fucked, right!?”

End of Chapter 5.

Author's Notes:

Y'know we were gonna get some Shining Armor/Twily into this sooner or later!

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