> Pinkie and Crew
>  by theponycaptorproject
> --------------------------------------------------------------------------

> A Rough Night Ahead
> --------------------------------------------------------------------------

“Come on, please Pinkie?” Pound pleaded. His little wings beat anxiously as he waited for her to respond. The expression on his face nearly broke Pinkie, and it didn’t help that Pumpkin was giving her the same look.
“I’d love to, you two. You really need to get to bed though. Your parents were kinda mad at me the last time I let you stay up.” Pinkie tried to block out their disappointed groans. She gave them both a soft smile, and leaned over their bed nuzzled them both.  “I want to keep babysitting you, and to do that I need to prove that they can still trust me. Now go to sleep.” They were clearly disappointed, but both twins threw their blankets over their bodies and lay down. Pinkie waved her hoof goodnight, then flicked the light to their room off, and made her way to her own room. 

---

Locksport saw the last light in the bakery flick out, and with a slight smile, he walked towards the darkened building. The Cakes were gone, his treasure would be all alone. The darkened and empty streets of Ponyville made a single figure easy to notice, so he moved quickly. Getting up to the door to Sugarcube Corner, he pulled out his kit. Using his magic carefully, he slid the thin piece of metal into the lock, and began to work. A click, and the slow groan of the door opening quietly announced his success.
The bakery was dead silent, letting him know that Pinkie was probably asleep. The door lightly closed behind him, and he threw his bag back over his shoulder. As he began to climb the stairs, he heard what sounded like faint snoring coming from the door on his left. His ears tilted back with slight confusion. Whenever he saw Pinkie through her window in the mornings, it was from the other side of the building. Could it be the Cakes? No, he’d seen them leave. Gently, trying to avoid any creaking sound, he tilted the door open. 
Lying in a large bed at the other end of the room were a pair of young foals, the Cake twins. ‘The Cakes must have left them with Pinkie again.’ Locksport thought to himself. This was unexpected. He’d talked to the Cakes when he was last in their bakery, and had sneakily asked if they were bringing the kids with them to Canterlot. They had said yes, but obviously had changed their minds. Well, there was only one thing to do. 
Glancing back into the hall to make sure that there had been no movement, he slid into the foals’ room, gently closing the door behind him. A lightly thumping sound echoed through the still air, as he set his bag down. Reaching into the bag, he pulled out a roll of duct tape. It was a good thing that he’d decided to use this to tie up Pinkie. If he’d brought anything else, he wouldn’t have thought to bring enough.
Locksport slowly drew the covers back, to reveal the huddled foals full bodies. There were wearing pajamas. Pumpkin wore a simple, long shirt with a fluffy white trim. Lifting the bottom of it, Locksport could see that she had on a pair of frilly pink panties. Pound wore a dark blue, loose-fitting shirt with a pair of dark blue shorts. 
Moving quickly, but gently enough to avoid waking the foals, Locksport tied their back hooves together and their front hooves behind them. Then, once he was certain their hooves were secure, he taped their mouths shut. As he suspected it might, that woke them up. Pumpkin’s eyes fluttered open first. She groggily tried to lift her head, but quickly discovered her predicament. A muffled squeal of panic, and some furious struggling snapped her brother fully awake. He didn’t scream or thrash like his sister; just looked up at Locksport fearfully. For a moment Locksport was worried about the fact that he hadn't brought a horn ring, but the filly was probably too young to have solid control over her magic.
“Hush now, you two. I’ll be back with you in a minute, but I have a friend I need to visit first.” He whispered, then turned to leave the room. He’d need to move fast. Their gags helped dull the noise, but the twins would likely end up waking his true prize if he didn’t get to her first. The stallion’s shadow glided down the hall, and saddled up to the door that he suspected was Pinkie’s. The door creak slightly, making the stallion wince, but there she was. Pinkie was curled up in a little ball near the head of the bed, her body rising and falling with her breath. Locksport smiled, seeing that the twins hadn’t woken her up. Locksport was disappointed to notice that she wasn’t wearing pajamas like the twins. He crept forward, tape in hoof, towards the sleeping mare. Like the twins, he tied her hooves. Pinkie however, wasn’t as deep a sleeper. He had just secured her forehooves behind her, and was about to start on her back hooves, when she woke up.
“Hm, what...what’s going….” She mumbled out quietly. Locksport moved fast, reaching into his bag to grab the only proper gag he’d brought. Pinkie meanwhile tried to move, and quickly understood what was going on. Her eyes widened in fear, and she yanked violently at her restraints. “Hey, what is this? Let me go, let me mmphf!” Locksport shoved the ballgag into her mouth, and fought against the mare’s wild thrashing, to tighten the gag’s strap around her head. 
After finished what he had started with her back hooves, Locksport stepped back to admire his handy work. The mare was squirming pointlessly, her hair messy and hints of tears forming in her glistening eyes. Seeing his prized trussed up like this was beginning to make the stallion excited. Pinkie’s eyes went wide as she caught sight of his growing erection, and he could hear her squeak fearfully. He just flashed her a grin, and then lifted her up.
When he came bursting through the door to the twins’ room, carrying the struggling mare on his shoulders, he found Pumpkin on the floor. She must have fallen off the bed while struggling. Pound, for his part, seemed like he hadn’t moved a muscle. Locksport tossed Pinkie onto the bed, next to the colt. Pound did his best, with how little he could move, to squirm up next to Pinkie Pie. From the floor, Pumpkin looked up at him with a fierce glare. She was trying to look determined, but he could see how unsure she was of all this. He moved over to the filly, and plopped his bag down onto the floor next to her. Pumpkin's face went from determined to bright red in an instant, when she felt a hoof rubbing against her panities.
“It’s ok, calm down. I’m not here to hurt any of you. In fact, I’m going to do my best to make sure you feel really good.” Locksport said calmly. Pumpkin could hear Pinkie panicking as she heard him say this, but Locksport turned her head to look at him. Without breaking eye contact, he continued to lightly rub her through her panties. After a few moments, her breathing grew just a bit quicker. From the confused look on her face, he could tell that Pumpkin had no idea what he was doing, but he could also tell that it felt good. After a bit, he pulled his hoof away, and he could tell that she was disappointed. Reaching back into his bag, he pulled out a pair of scissors.
“I hate to ruin such a cute pair of panties, but these need to go.” He said, as he watched the red in her face grow brighter still. With a few swift motions, Locksport cut her panties apart, and then slid the remnants from her body. He licked his lips at the sight of her little entrance, slightly wet from his rubbing. Out of the bag, he pulled something else out. Leaning down to kiss the filly on the  head, he whispered to her. “It was naughty of you to try and crawl away like you did. Because of that, you’re going to have to wait your turn. For now, I’ll let this keep you company.” Her eyes went wide, and her back arched at the sensation as she felt him push a vibrator deep into her. With a flick of his hoof, the machine buzzed to life, and Pumpkin moaned into her gag. He left her there, wriggling on the floor from the new sensation. 
He jumped onto the bed next to Pound and Pinkie. They both looked up at him fearfully, and he chuckled. Using the same scissors he’d used on Pumpkin, he cut away Pound's shorts, ignoring Pinkie’s muffled protests as he did so. The tattered bits of cloth fell away to reveal a little cock pointed straight in the air. Locksport let out an amused laugh.
“All this has you a little excited, huh?” He asked, as the foal looked up at him, clearly not understanding what he meant. Another squeak from Pinkie Pie caught the stallion’s attention, and he grinned as an idea formed in his head. He wrapped a hoof around Pound’s shoulder in a friendly way. “Tell you what, how about we let Pinkie Pie show you what I mean.” Pinkie looked at him in abject horror. “And she’ll do it too. Right Pinkie.” There was a clear threat in those last two words, and Pinkie saw the stallion grip tighten slightly around the colt’s shoulder. The threat was obvious, ‘do it, or I hurt them.’ Pinkie whimpered, but nodded. 
“Good. Now Pinkie, I’m going to ungag you.” He leaned forward and whispered into her ear. “If you try and scream, I’ll make this much worse for all three of you. Now, why don’t you suck off our little friend?” There was a click as the strap came loose. The gag came away from Pinkie’s mouth with a small string of saliva connecting it to her lips. Locksport helped Pinkie get into a lying position above Pound’s little cock. The foal was clearly confused about what was going on, and he kept trying to get Pinkie’s attention with squeaks and mmphs through his gag. The pink mare refused to meet his eyes though.  She lay with his erection a few inches from her face, her heart hammering. “Pinkie….” She turned to look at the voice, and saw the impatient look on her captor’s face.
“Sorry.” She quietly replied, “I’ll…I’ll start.” Pound’s eyes were as wide as saucers when he felt Pinkie’s tongue lightly lick the tip of his erection. He quickly glanced between Pinkie’s miserable face and Locksport, who was stroking his own cock. Pound squirmed in his restraints slightly, not sure if he was comfortable with what Pinkie was doing or not. 
The colt’s penis was understandably small, so Pinkie was able to take it all into her mouth without any trouble. She reasoned that the faster she could bring Pound to an orgasm, the quicker this would be over with, so she set right to work. Her poofy mane bounced against her face as she began to bob her head, sliding her tongue along the underaged bulge in her mouth. Every few times, when she reached the top, she’s pause and swirl her tongue along the head. Pound’s confused squeaks grew louder, but the fear in his tone was quieter. There was a hint of enjoyment now. He looked back up at Locksport, hoping for answer from the one pony in the room whose mouth was free.
“I bet you’re curious about what’s going on, aren’t ya?” Locksport asked, when he noticed the look. Pound nodded. The stallion shifted on the bed so that he was closer to the colt. “I’m just helping your babysitter teach you how to feel good. Do you want her to keep going?” He asked playfully. Pound nodded quickly, a pleading look in his eyes. Locksport chuckled, “Ok, then I’m going to need you to do something for me.” He reached out, and tore the tape off of Pound’s mouth. The colt winced, but quickly responded.
“What do you want me to do?” He asked, curious. His eyes went wide again when Locksport shoved his cock in the foal’s face. 
“I’m going to need you to do what Pinkie’s doing to you. If you don’t, I’ll tell her to stop.” He replied. Pound’s face screwed up in disgust, and Locksport could hear Pinkie quietly start sobbing around Pound’s cock. Despite this, she kept doing her best to at least make sure Pound felt good. She moved her bound hooves so that she could cup and begin massaging his balls, and Pound let out a moan of pleasure. whatever Pinkie was doing, he didn’t want it to stop. 
“Ok, I’ll do it.” Pound answered, embarrassed. The stallion grinned, and pushed his cock up against the foal’s cheek. He suddenly realized, that for as much as he knew about Pinkie, he couldn’t remember much about the twins. It had never seemed important until now.
“Before you start, would you tell me your age? I’d like to know how old you and your sister are as I take your virginities.” He asked with a clear lustful tone. Pound wasn’t sure what virginity was, but he saw no harm in answering.
“We both turned nine a few months ago.” Pound answered, and was made even more confused when the stallion grinned after hearing that. ‘So deliciously young.’ Locksport thought to himself. Not wanting to wait anymore, the stallion shoved his cock into the foal’s mouth. Pound let out a squeak of surprise, and he clearly wasn’t comfortable with how full his mouth felt. Locksport didn’t really care, and he didn’t feel like waiting for the colt to get used to the sensation. He began to rock his hips, his cock going pretty deep into Pound’s throat. The colt coughed slightly, but did his best to take it. It was unpleasant, but the heavenly sensation of Pinkie’s lips around him convinced him it was worth it.
Punctuating all of this, was the sound of Pumpkin’s moaning. The vibrator was still deep inside of her, and the machine had been slowly bringing her closer and closer to bursting. Pinkie felt Pound begin to move his hips, humping up into her face, and realized that both of the twins were getting close. Sure enough, a long, muffled moan filled the room. Pumpkin had her eyes screwed shut. Her whole body was twisting, and writhing. Her hips pumped into the air in an instinctual movement. She wasn’t sure what to call what had hit her, but her whole body was shaking as she experienced her first orgasm. The sound seemed to set off Pound. His little cock flexed in Pinkie’s mouth, his balls trying to squeeze his nonexistent cum into her throat.
Locksport took that as his queue. He was still pretty far away from his own orgasm, but that was fine. He had more in mind for the night anyway. He pulled out of Pound’s mouth, much to the colt’s clear relief, and leaned back.
“Did you have fun?” 
“Yeah.” Came the breathless foal’s reply. He was panting as he tried to recover from his first time. Pinkie slowly pushed herself away, and looked at Locksport, hoping she was done.
“Well, that’s one down.” The stallion said, amused. He rolled off the bed and made his way over to Pumpkin. The young filly looked up at him with an amazed expression. As soon as he tore the tape off her mouth, so blurted out a question.
“What was that?” Pumpkin asked. Locksport clicked the vibrator off, and chuckled when he heard Pumpkin’s disappointed sigh.
“That was what it feels like to have sex. Would you like to have some more?” 
“Yes! Yes please, sir. Can you put it back in?” She asked, referring to the vibrator. Locksport shook his head. 
“No, not this time. This time, you’re going to have sex with me. Now I’m going to cut you loose for now. I’ll make this easier.” He grabbed his scissors and sliced away the tape that he’d tied her up with. Standing up, he moved to do the same to Pound. Pinkie, he left restrained. The foals seemed a little scared, but were curious enough that he doubted they’d try anything. Pinkie though, he couldn’t trust her as much. The two foal’s, now free from their bonds, were looking to Locksport. They were clearly wondering what happened next. The stallion climbed up to the head of the bed, and lay down. He patted the spot next to him while looking at Pumpkin, and she came over to him.
“Is she going to do that thing with her mouth to you?” Pound asked curiously, his little cock getting hard again.  
“No, she’s going to be doing something else.” Putting his hooves around her, Locksport lifted the filly up, and set her down so that she was lying on top of him. His cock was pushing up against her young ass, and Pumpkin quivered anxiously, not sure how this was going to feel. 
“No!” Pinkie whined. “You...you can’t! She’s just a filly, you’ll hurt her!” The mare squirmed to get free, but got nowhere. Pumpkin looked back at the stallion holding her, terror clear in her eyes. 
“It’s ok.” Locksport whispered. “It won’t be that bad, and you’ll get used to it fast. I’ll make sure it feels as good for you as it did last time.”
“You promise?” The filly asked, hesitantly. Locksport shot an angry glare over Pinkie’s way.
“Of course. In fact, Pinkie is going to help me make sure you enjoy it.” Without waiting for the mare to respond, Locksport began to push into the filly. Pumpkin’s breath caught in her throat, and she let out a loud yelp as she felt her small body being stretched out.
“When….” She winced, then continued, “You said I’d get used to it.” It clearly hurt, but obviously not too much. Locksport was impressed with the little filly.
“Yes, and it won’t take too long. I’m going to start moving, are you ready?” He asked, not really caring how she answered. Pumpkin nodded, though her eyes were screwed shut. Slowly, Locksport began to sway his hips. The sensation of this young filly’s tight ass clamped around him made him want to go faster, but he restrained himself. The little gasps and uncomfortable moans he received let him know it was time to get Pinkie involved. “
Ok, Pinkie Pie. Get over here, and help make sure that little Pumpkin here enjoys her first time. Give her a good lick.” The mare sniffled, but began squirming her way across the bed until she was right in front of where Locksport was pumping into her little Pumpkin. She could see his large cock burying itself inside of her, and could see the glistening of Pumpkin’s filly juice reflecting the moonlight as it ran down towards the bed. Gulping to prepare herself, Pinkie made the dive.
Locksport could feel the moment that Pinkie’s tongue began to work. Pumpkin’s back arched against him, and her whole body stiffened. Her hips began undulating, trying to push into the muzzle that was beginning to treat her. Now that the filly was receiving her treatment, Locksport began pushing into her even faster. He grabbed her legs and pulled them up into the air, giving Pinkie better access to Pumpkin’s young pussy. The filly’s ass wrapped around Locksport’s cock wonderfully. Still, something seemed like it was missing. A quick glance to his left let him know what it was. Pound was watching all of this unfold with amazement. His hoof was around his cock. He was mimicking what he’d seen Locksport do earlier, and was slowly stroking it.
“Hey Pound. Your sister still has one hole that she isn’t using.” When the colt gave him a confused look, Locksport clarified, “Her mouth, Pound. Don’t just stand there stroking yourself, show your sister how to use her mouth.” A huge grin flashed across Pound’s face as he realized what Locksport meant. The colt climbed over their bodies, positioning his legs on either side of Locksport’s body, and moved up to where Pumpkin’s face was. The filly’s eyes were glazing over from the fullness she felt in her ass and from Pinkie’s hard work, but she gave her brother a weak smile. 
“Can you open your mouth please, sis?” Pound knew that Pumpkin couldn’t have seen what Pinkie and him had done from where she’d been on the floor, so he’d need to do this himself. Pumpkin, at this point, was willing to try about anything, and readily opened her mouth for Pound. The colt slide his young cock into the mouth, and Pumpkin correctly assumed that she was supposed to close her mouth around it. Now that his penis was buried in her mouth, Pound began to rock his hips, pushing into her as far as he could. Pound was still very small, so Pumpkin had no issue taking it all in.
Locksport couldn’t believe how well all of this was going. He had only really planned on raping Pinkie Pie, instead he found himself in a foursome with two nine year old cuties. Pumpkin moaned around Pound’s cock, saliva running down her chin messily as the young colt facefucked his sister. Her hips quivered, feeling Pinkie lick deeper and deeper into her folds. With a muffled scream, Pumpkin came again. Her hips bucked towards the ceiling, and her juices squirted out, covering Pinkie’s face. The sound of this tender filly cumming almost set Locksport off, but didn’t want to be done just yet. He wanted Pinkie to be the one to finally receive his cum.
“Alright everypony that’s enough.” He shifted his weight, forcing Pound to climb down, and eliciting a disappointed groan from Pound.
“I was almost done.” He pouted. Locksport winked at him playfully, as he pulled himself out of Pumpkin’s ass. 
“You don’t have to stop completely, I just meant I wanted you guys to get off of me. You saw what Pinkie was doing to your sister right?” Locksport asked. Pound nodded. “So, why don’t you do that with Pumpkin, and she can keep using her mouth on you?” Pound thought for a moment.
“What about you?” He asked. 
“Pinkie has helped you two already, now she’s going to help me.” Locksport replied. Pound could hear Pinkie sob quietly upon hearing that. He felt bad, she clearly didn’t want to be doing any of this. Pound wasn’t sure why, it felt amazing, but he still didn’t want this stallion to hurt her. Seeing Locksport loom over him though, and remembering how the night had started with the stallion tying them up, he correctly assumed that he couldn’t do anything about it. If this was going to happen anyway, he might as well try and enjoy it with Pumpkin. He shot a sincerely apologetic look towards Pinkie, and then came over to his sister.
Pumpkin was still recovering from her second orgasm of the night, of her life, when she saw Pound lie down next to her. She’d heard what Locksport had said, and wasted no time. She leaned her head down, and put his cock back into her mouth. Pound meanwhile, repositioned himself so that his face was down around her pussy. He licked it experimentally, and after getting a long moan from Pumpkin in response, grinned and dove in for more.
Pinkie watched the whole thing in disbelief. It was surreal, seeing this foals that she’d helped to raise doing something like this right in front of her. In spite of everything, she was glad that they were having fun. Maybe they’d come out the other side of all of this without any real lasting problems. She hoped so. A hoof slapped her butt, causing her to yelp.
“It’s finally time, Pinkie. I want you to know that none of this went the way I’d originally planned. I was hoping to find you alone in here. Not that I’m complaining, this has been way more fun than I had dared to hope it would be. Now though, it’s finally time for the main event.”  Pinkie shook her head. She knew it wouldn’t matter, but she didn’t know what else to do.
“Please, you’ve had your fun. Can’t you just leave?” She pleaded. Locksport lifted her up, and lay her down at the head of the bed with her chin resting on the pillow. She could feel his cock lining itself up with her ass. There was some pressure as it pushed up against her. “Please,” she squeaked out, tears streaming down her cheeks, “Please don’t do thmmphf!” The ball gag was shoved back into her mouth, and Locksport clicked it’s strap shut behind her head.
“Shhh, we don’t want to upset the foals. Just do your best to enjoy this. Ok?” He leaned forward, and kissed her tear-stained cheek. Pinkie closed her eyes, and buried her head in the pillow, accepting that this was going to happen. Her shoulders shook as she cried silently, feeling him push into her. Locksport was gentle, at least. He took it slow, and watching Pinkie to make sure he wasn’t hurting her, physically at least. His hooves caressed her supple thighs, and he moaned blissfully. This was what he’d been waiting for. So much planning, and he was finally enjoying the results. The tight grip of her ass around his cock was even better than Pumpkin’s had been, and her quiet sobs just egged him on.
Neither Pound or Pumpkin had any real idea of what they were doing, but they both knew that they were loving it. Pumpkin had begun grinding into Pound’s face, her filly juices now covering most of the bottom of his face. Pound hammered into his sister’s mouth, enjoying the slapping sound his balls made as they hit her muzzle. Both of them felt the other’s body with their hooves in awkward but passionate movements. It didn’t take either of them long to finish. For the third time that night, Pumpkin felt herself cumming. She moaned loudly, sending wonderful vibrations through her throat to Pound’s cock. Pound gripped onto her butt and rolled them both so that he was on top of her. With his new leverage, he humped furiously into her face. The now thoroughly fucked filly did her best to take it. Finally, with a final shove into her mouth, it was Pound’s turn. His body twitched as he experienced the second orgasm of his life. When it was all over the two of them just lay there panting, stupid grins of pleasure slapped on both of their faces.
Locksport noticed the foals finish, and smiled. He’d enjoyed introducing them to sex. Hopefully, they’d continue practicing with each other when this was over. He leaned over Pinkie Pie, so that his body was enveloping hers, and whispered to her.
“Looks like our little friends are done for the night. I bet you want to be too.” Pinkie didn’t look up or open her eyes. She just nodded as she continued to cry into the pillow, little whimpers coming out from behind the gag. Locksport kissed her cheek and nibbled on her ear, as he picked up his pace. The slap of his hips against hers sped up, and Locksport began to feel a growing sensation. He stood back up, and rammed into Pinkie as fast as he could, ignoring the whimpering it brought out of her as he did. It finally paid off, and  Locksport yelled out as he shot ribbons of cum deep into Pinkie’s ass. Pulling out, he covered her back and butt with all the cum her had left. Realizing that he was done, Pinkie fully collapsed unto the bed, breathing hard. 
That was it. Locksport was done. He had finished what he’d come here to do, and it was time to leave. He climbed off the bed, and the Cake twins eyes followed him as he reached back into the bag he’d brought. He pulled the tape back out, and came towards the twins.
“Wait,” Pumpkin cried out, suddenly nervous, “What are you doing?”
“Relax,” Locksport replied, “I’m just making sure that you don’t do anything dumb before I leave. Now, lie down and put your forehooves behind you. Nervous, the foals did as they were asked, and Locksport retied their forehooves. He then tied their back hooves at the knees and ankles, and placed long strips over both of their mouths. Reaching into the bag for a final time, he spoke up, “I wanted to leave you three with some going away gifts. I hope you enjoy them.” 
They were vibrators. Pumpkin’s eyes lit up with delight, and Pound and Pinkie let out horrified little squeaks. Locksport had brought extra, just to be sure that he had a size that he’d want, so he had enough for each of them. He pushed a vibrator into Pinkie and Pumpkin’s pussies, and into all three of their asses, then he did his best to secure them in place with tape. That way, they wouldn’t be able to get them out without help. Once he was sure all five were in place, he flicked them on. Within moments, the room was full of the sounds of moaning and gasps of pleasure. Looking over his captives one last time, Locksport walked out of the room. He left them all writhing on the bed. Over the next several hours, they all came more times than they could remember. Their bodies twisted against the tape restraining them, and their hips humped unconsciously into the air as they came again and again. Until the next morning when, at last, the Cake’s found them.