"Alright, so here's the deal," Diamond Tiara told the confused would-be robbers and did-be rapists. "You can have all the bits in my bag, and just leave, until a guard finds me. He'll sent me back to the convent, and you straight to jail once I tell him how you were being evil, not nice robbers. Or, you could help me escape the guards, and I could help you escape the guards, and you’ll have a lot more money than in my bags.”
“What’s th’ catch?” one of them pointed out.
“Dis got catch written all over it,” the boss agreed.
“No catch,” Diamond said, “You just get me on the train, and I’ll tell you where the bits are hidden, and you never have to see me again.”
“Wouldn’t mind seeing that again,” one of them mumbled, earning a kick from their leader.
“How do we know you gots the bits at all?” the leader said. “You get on the train, you just laugh at us, and we’s broke as fillies outta summer.”
Now that she wasn’t so sex deprived, as to be horny up to the eyeballs, Diamond remembered she actually had a foal on the way. She worriedly tested the tightness in her belly, but there didn’t seem to be anything wrong. She sure wasn’t enjoying sex any less than she did before getting pregnant. She was still pleasantly buzzing from the activity, and she was sure having an easy time talking to these ponies. Really, Diamond Tiara felt over the moon.
“How about,” she said craftily, “Because they’re hidden in two places? If you don’t think I have the bits, then why don’t you try looking behind those trash bags over there?”
The boss squinted at her, but tilted a head at one of his lackeys, who went over to check. “There’s like three times the bits than in her bags!” he shouted out having hefted up the sack of bits she stashed back there.
“Just think of it like a gift~” Diamond said sweetly, trotting right over to her saddlebags and shoving her head under them, feeling the satisfying clink of bits as she slid them onto her back. “I’ll tell you about the rest, when you get me on that train.”
“I think we gotta deal, filly,” the boss said agreeably. “But uh, what’s you gonna do until the mornin’?”
Diamond scrunched uncertainly, “We have to wait until morning?” she asked in worry.
“Ain’t no trains until an hour past dawn,” lackey 2 said. He seemed like the smart one. “The schedule’s crazy I know.”
“I guess just like... stay around here,” Diamond said uncertainly, looking around and shivering. It was the middle of the night, but it was summer so it wasn’t too cold. She had slept most of the day before, but... she was used to sleeping at night.
“Why don’t we take her to the hideout?” lackey 1 said helpfully. “She can stay the night!”
“I dunno,” the boss said. “Still don’t know as we can trust her.”
“Hey, maybe she can go anudda round,” lackey 2 suggested, tilting his head towards the leader in the shadowy alley.
“Welcome aboard, filly!” the boss whinnied out, with a broad, gap toothed smile. “What’s your name, anyways?”
“Oh, like...” darn it Diamond couldn’t use Lollipop. That was the name that would be on her wanted posters, which she was pretty sure existed. “Strawberry,” she said in absence of any ideas. “Strawberry... Cream.”
“She’s fulla cream alright,” lackey 2 remarked. Diamond blushed. She honestly hadn’t expected anypony to get that joke. Would they figure out it’s a fake name?
Turns out it didn’t matter. “Well Creamy,” the boss said, “I’m Mo, and this is Edge and Larceny. It ain’t much, but we can get you outta sight, and then we can cash out on your little train trip in the morning.”
“With this much dough, we can even order out,” the pony who was named Larceny said hefting the sack in his hoof.
“I dunno if this filly wants her belly filled,” Edge said, with a leering smirk.
“Um, yes?” Diamond answered unsurely. “You took care of my filly place just now, so my belly’s the only thing that still needs like, filling.. Don’t you remember?”
“Well—” Edge turned away quickly, “Well I’m just—sayin’” but couldn’t finish his sentence as Larceny was too busy interrupting him with laughter.
“I don’t see what’s so funny,” Diamond said stomping a hoof, still feeling all sore raw and melty squishy back there. “Fillies want their filly place and their bellies filled, and I haven’t like, eaten anything but grass for the past two days!”
“Ass a story I gotta hear,” boss Mo said, turning on his heels to lead the way. “C’mon, the hideout’s down this way.”
Their hideout, as it turned out, was a crummy apartment, right next to a hayburger. Even the prospect of hay that hadn’t been fried in extra virgin olive oil, and served over a bed of fresh spinach was making Diamond drool in anticipation, but the boys expressed nothing but disgust at having to smell that all day. It was pretty messy in that apartment, with boxes and wrappers tossed haphazardly around the floor.
In the better light, Diamond got the first good look at her attackers. Mo was a dark brown, almost coal colored. It made his dark blue mane and tail look light by comparison. His eyes matched his hair, and his cutie mark looked like a clock of some sort. Edge had blue hair too, a brighter shade, magenta eyes, and a pastel red furred hide. His cutie mark was a couple of horseshoes. Larceny was a dangerous looking lavender pony, his lime green mane reminding Diamond of something... she couldn’t quite put her hoof on. His cutie mark was the closest either of the three had to a robber cutie mark, some kind of a knife digging into a groove. None of the three were pegasi, but Larceny was a unicorn.
Now that the buzz from her earlier activity was wearing off, Diamond’s vagina was feeling really sore. It was the sort of pain that was bad because it bothered you how you couldn’t get away from it. She really hoped she didn’t pull something in there. Diamond hadn’t been entertaining stallions in like, a really long time. No doubt her insides were as out of shape as her body was in shape. Because months of plain food and more exercise than she’d ever gotten in her life took a toll on her. When Diamond paused at a dirty mirror discarded on the wall, she was immediately captivated by what she saw.
There hadn’t been mirrors at the convent... or anywhere, for the past... months or so really. Diamond had tons of mirrors at home, but that was something only well-to-do ponies could enjoy. Heck, this mirror was probably stolen, from the looks of it. But what was inside it, Diamond hardly recognized.
It wasn’t that she looked bad. The weird thing is, she looked good. Her coat was so filthy you could hardly recognize her as pink anymore, and her hair was a wild mess of tangles, but her flank was tight, and her hindquarters were more pronounced... from all the trotting around she told herself. Her muzzle looked thinner, her soft round chin having slimmed out from all the... not eating stuff.
She looked good, but she wanted to be not hungry!
“Toldja this mirra would get us all the chicks,” Diamond heard Larceny saying jokingly behind her.
“Hey if I’s was a filly like that I’d be lookin’ in the mirra all the time too,” Edge told him wryly, as Diamond turned away from her own reflection.
“You wanna be a filly?” Larceny retorted smoothly. Edge spluttered and couldn’t quite answer in a definitive fashion, because it looked like he wasn’t willing to say anything insulting about fillies around... well... Diamond.
“Don’t worry about how I look,” Diamond said self consciously, “How about what we’re gonna eat tonight?”
“Boss left already,” Larceny said, leaning back in a torn up old chair and waving a hoof at the door. “With a purse like you got, we can afford somethin’ special.”
“Like...?” Diamond prompted eagerly, trying not to drool in anticipation.
“Pizza!” Edge exclaimed, with a delight that didn’t befit a stallion with a scar over his eye.
Diamond failed to not drool in anticipation. She didn’t even get pizza back at home! It was like, really bad for you or something, and not fine quality food expertly prepared by blah blah blah, but Diamond loved the stuff. Even though she usually could only get pizza cold, since when she stole it from some other foal it took too long to make her escape. This time, Diamond hoped it would be like, really fresh out of the oven!
While waiting for Mo to return, Diamond got to explore their little space. She found thrown over the back of a couch, a bunch of thick aprons, with dark, blackened burns all over them. “What are these?” she asked curiously, lifting the fabric.
Edge who was closest, answered her with an eye roll, and a disparaging, “Oh, dat’s our udda job.”
“Edge!” Larceny shouted out, trotting across the room, “You ain’t supposedta tell ponies about that!”
Edge just shrugged, saying, “She seems cool.” Diamond was about to defend herself, but then he said that, and she... wasn’t sure what to do when somepony else was actually vouching for you. Stand there and blush? Sounds like a plan.
Larceny sighed exasperatedly, and said, “Yeah we work at the steel mill, when they got woik. Thankfully,” he gave a tight grin, “We got anodda occupation with which to supplement our income.”
“Why are they so burnt?” Diamond inquired, touching a hoof to the thick garments again.
“When you’re shovelin’ metal inta the furnace, you get burned,” Larceny said noncomittally.
“It sucks,” Edge spat out a little less noncomittally. “They aprons don’t even protects your flank, and shovelin’ all that metal all day. Why they got so much ta scrap?”
“So... why don’t you get another job?” Diamond prompted uncertainly.
Larceny snorted a laugh at that. “Ain’t no other work out there for a stallion,” he explained grumpily, “Outsides joinin’ the guard.”
“You think we’s stealin’ for fun?” Edge said with a frustrated anger. “It’s all a buncha meadow muffins, but I’s dyin’ before I go join the—”
“Boss is back,” Larceny said, looking at the sound of a heavy trotting approaching the door to the hallway.
“Alright, eat it quick,” Mo uttered, pushing his way into the apartment. On his rump were three pizza boxes stacked up. “They gay’me it right outta the oven!”
Diamond never in her life thought she would appreciate a simple cheese and beet pizza so much as she did this evening.
With the pizza finished, and everypony’s bellies fat and happy, Diamond was about ready to just drift off to sleep like this. The stallions looked pretty relaxed too, sprawled on the couch, or the bed. But little did she know, they had an opportunity here that they wanted to take full advantage of.
“So we gots a lovely little filly for the night,” the boss said earning everypony’s attention. “Who wants to top her off before the evenin’?”
“Top me off?” Diamond thought puzzled. “Wait does mean...?”
Before Edge and Larceny both raised their hooves, Diamond exclaimed excitedly, “You guys can go again?”
Larceny immediately blushed and said nothing, but Edge smirked and said, “You ain’t been with a grown stallion, have you lil’ filly?”
“Well I just... I mean, I thought...” Diamond shifted to a standing position, already remembering their penises inside her, with such a bittersweet intensity. She only got to do stallions once, but she never knew what happened to the stallions after they left her room. Perhaps there were some who could do it twice! During her time with that lonely colt, Diamond found Strawberry had had... some erections in the morning, even after doing it at night, but he was reluctant to use them. But Edge wasn’t?
But... she was so sore...
“I’d like, really like to see what you can do,” Diamond said in a disappointed tone to the three stallions, “But I like, haven’t done this for a... while. It still like... hurts in there.”
“Well yeah, sex don’t feel good for mares,” Mo said authoritatively. “You just gotta put up with it, take it like a mare.”
“Well—it usually feels good though!” Diamond said stomping in frustration. “I want it even now just... I dunno if I can take it!”
Mo blinked at her, saying, “Really? How’s it that it could feel good for you? Jammin’ some big thing up your cooch?”
“It feels like... stretching,” Diamond said with a blush, “And the inside of my... cooch feels good when you slide in it. And how is it like, possible not to feel good, when somepony’s rubbing your clit? I mean, like, my clit. You all have penises, not... that stuff.”
“I ain’t buying it,” Larceny said shaking his head. “You ain’t got a nothin’ just a hole back there. You’re just makin’ up words like clit so’s you can impress us.”
Wow, it’s no wonder these stallions had never pleasured a mare before. Diamond turned and presented for them, spreading her ...admittedly sore, but excited petals with a hoof, saying, “There’s a special button back there, just a tiny little spot. All you have to do is touch it after your mare is really wet, and it’ll feel really good for her! If she doesn’t feel good, it’s probably because you’re missing it.”
“Where’s it?” Larceny said as the three of them elbowed at each other to see closer.
“Well it’s like...” Diamond blushed and turned to look at her own hindquarters, but she couldn’t really see, and, “Like, my hoof is too big and um... hold on.”
She lay down and rolled belly up, a thrill of excitement going through her as she spread her legs before these stallions, reaching down with her forehooves to spread her petals again. “My entrance,” she explained, “Is down lower. That’s where your penis goes in. And above that is my pee hole, and above that is my clitoris!”
“It just looks like a buncha pink,” Mo grumbled in frustration.
“And really hot,” Edge declared alongside him. “A mare... filly spreadin’ like that really makes me just wanna jam it in and go.”
“Oh, can’t hold back?” Diamond said wiggling her short legs coyly. What was she doing? This was gonna hurt, so why did she want it so bad? “Guess my filly parts are so pretty, you just wanna give me all your foals,” she teased him.
“Yeah I—” Edge said, pushing forward to straddle her, just rubbing his dick alongside her pussy. “Yeah I—” he repeated, staring down at her intensely. Diamond shivered with fear and arousal, succumbing to the tingling temptation down there just as he succumbed the urge to... jam it in and go. She couldn’t believe he got erect again, so soon!
“Woah, Edge!” Larceny danced back as the red and blue stallion surged over her.
“He’s really into this filly,” Mo said in a note of amusement. “Sorry Creamy, I guess you’s gonna have to take it anyways,” he teased her. “Better hope he gets your clit-or-whatever.”
“I...I... his penis is on it,” Diamond moaned needily, her hips arching up against that sliding dick. “He’s gonna... just shove it in and... and then I’ll use my... my hoof—!” she gasped out, as his eager humping became more purposeful, dragging the tip of his shaft to prod at her rather than slide against her. Prod at the entrance to her deepest parts. A whine grew in Diamond’s throat as she tried to stretch around him, his dick sliding into her sore passage, pushing it wide and deep, and she gurgled a scream in her throat as he pushed all the way in, and jammed his hips right up against hers.
A pillow hit Diamond in the face.
“Bite on that, Creamy,” Larceny said helpfully. “You’s can’t wake up the neighbors if you’re gonna scream.”
Diamond whimpered, but did bite on the pillow, and clutched it between her forehooves. She was twinging with soreness, but it was like, fading before the pleasure. She was so freaking wet in there! His slippery sausage started plumbing in and out of her and Diamond couldn’t help but squeak into the pillow at the incredible sensations. Every heave of his hips was another penetration, her deepest places filling with stallion. It wasn’t long before she lost the pillow, her head rolling back and panting at the air, while he thrust Diamond into utter bliss.
“I—!” she exclaimed at a surge of pleasure. “I think I’m gonna like—!”
Edge jammed his hips against hers, and inside her, Diamond felt his penis thrashing in there. “Nooo...” she whimpered, and “Yess....” as he finished in her. Diamond hadn’t climaxed, but she felt hot spunk pump into her birth canal, and that was incredible. She took everything he could give. Diamond just stared at her dick stuffed hips, more secret seed being delivered deep within their depths.
“Oh mare that felt good,” Edge husked out in relief. He stopped looking forward with intent after his climax wound down, and looked down at her again. “Havin’ a mare to do this to, you don’t even knows...”
“I... I know,” Diamond said as gently as she ever said anything. “I f-felt good too, after... you started. It stopped being sore, and now I’m just full.”
“You didn’t even do that clit thing though,” Larceny pointed out critically. Diamond looked over at him from under a softening Edge.
“Yeah, that’s why I like, didn’t climax,” she said snippishly, “If I touched it I totally would.”
“Oh come on how’s fillies gonna climax?” Mo said shaking his head. “You ain’t even got no spunk to squirt out!”
“I did climax in the alley,” she said in an unimpressed tone, “When a filly climaxes, she squeezes on your penis again and again. Just like you pump her full of ‘spunk,’ again and again. She can’t help it! A-and I didn’t because—ugh!” her words were cut off as Edge finally heaved out of her, and walked over her, his slick dick trailing along her belly and chest before he passed beyond her. “Because I didn’t touch this,” she said, eagerly bringing a hoof down to her folds. It was mere child’s play to find her clitoris at this level of arousal. Diamond’s breathing grew heavier almost immediately as the pleasure surged in her, and her insides squirmed around Edge’s semen. “I—I’ll totally do it,” she told them with half lidded eyes. “You think I can’t? S-show you gonna... nngh...climax...”
Diamond focused on herself from then, and they let her do it, until she was convulsing inside and arching upward, giving a sweet cry of pleasure at the amazing ripples inside her, the stars filling her body with electric glee. She did it right there in front of them, and didn’t have to wait until she was alone. Because she didn’t care about them. They weren’t gonna tell her daddy, or pay her money, so she could do whatever she wanted. So she just made herself orgasm, and ignored the words they spoke to her pleasure clouded mind, as she floated along in the bliss of orgasm.
Suffice to say they were quite well convinced, but Diamond felt even more wiped out after that second orgasm. She tried to pretend to be enthusiastic, since she’d gotten them all worked up and stuff, but she was just too tired, and in the end, even though he was rocking his penis in her, Mo was cradling her against his chest, and he felt so warm and comforting, it was hard not to... just...
“Oh sure, laugh it up,” Diamond grumbled the next morning, chin laying resolutely on the breakfast table. Which also served as the coffee table, the laundry table, the work bench, and the kitchen counter. The thick, rich pizza had helped fill her up... a lot. They were surprised how much of one Diamond managed to get down, but she was still hungry when she woke up. So even though breakfast was the usual for them, which is to say packaged hay and coffee, Diamond still ate it. She didn’t taste it, but she ate it. “It was past my bedtime!” she grumped, but that only led to more chortles.
“So me an’ the boys been thinkin,” Mo said while Diamond munched on her hay. “You’re that filly from the convent, aren’t ya?”
Diamond tried not to choke on her hay.
“Some filly stola lotta bits when she hopped the fence,” Larceny commented, “They been out huntin’ for her and everything.”
“Well like yeah, that’s why I gotta get outta town,” Diamond said conservatively, eyeing the distance between her, the others, and the door out of here, “But if you turn me into the convent, you won’t get to keep any of all those bits I supposedly stole.”
“Yeah but filly, y’know it’s a convent,” Mo continued unhappily, “Ain’t we not supposed to steal from ‘em?”
“Why not?” Diamond asked incredulously.
“Well sometimes they does food drives for the poor?” Mo said unhappily, “Though since we’re all technically workin’ stallions, we cain’t get any.”
“Well think of it like a b-bits drive,” Diamond worked out carefully, “They’re just donating to some needy stallions, without knowing it!”
“But still,” Edge said uneasily, “All dose fillies dat need it...”
“They ain’t gonna be a problem come winter,” Larceny said with a roll of his eyes. “You wanna give a bunch of bits to somepony who’s just goin’ six feet under in half a year?”
Mo looked like he was pondering deeply, before he firmed his lip and gave Diamond a steely eyed gaze. “I ain’t gonna go hungry for a buncha bleedin’ hearts,” he said coldly, “Tell us where your stash is, and we’ll get you outta this town fo’ good.”
“We’ll make way betta use of the funds anyways,” Edge said with a thick laugh.
“I’ll tell you,” Diamond said, trying to puzzle out all this weird slang they were using. “But only after I’m ready to get on the train. That was the deal, remember?”
“Sure was,” Mo said agreeably. “We’ll getcha right over there. Say, you wanna go just one more round all quickie before ya leave? Somethin’ ta remember us by.”
“Round...” Diamond puzzled uncomprehendingly, “A round... quickie? I guess so? What’s a quickie?”
“He means hot an’ heavy on toppa you and buried hip deep in dat ass,” Larceny clarified helpfully.
Diamond was going to be walking funny for days, but that didn’t stop a grim smile from spreading across her face.
The third time with the three of them was pretty difficult. Diamond was still all sore in there from the day before, and felt really raw. It was alright after she got wet, and by the time Larceny mounted her, she was cooing out his name like he was the greatest thing that ever happened to her. But... she definitely had a limp in her gait, as Diamond clumped wearily to the bathroom to clean herself off. The three stallions satisfied, she just wanted to soothe her inflamed vulva with the cool water that came out of gurgly indoor plumbing.
And then orgasm.
She didn’t tell the stallions, but Diamond was hurting too much to really orgasm while they were doing her. But by herself, she could painlessly stroke her way to bliss, the memories of their rough penetration only helping fuel the fire inside her that took over her body and left her huffing needily, just standing there in the bathroom biting her lower lip, rocking lightly together with the powerful rhythmic pulsing inside her rear end.
True to their word, the robbers got Diamond on that train. This was perhaps unusually reliable for these three, but Diamond had a pretty good idea that they were going to follow through with their promise. Stallions just got so much more agreeable and... malleable after they were buzzed from cumming inside her. That was why you always stated the extra charges after the services had been performed, since her customers were more likely to just smile goofily and pay them without a second thought.
A scary thought occurred to Diamond, that maybe they’d feel like having her around to stick their cocks in would be preferable to any amount of bits she could get for them. But she played it up really well, and their eyes glittered with greed, or was it hope? Diamond had a hard time telling the difference between greed and hope. Same thing, right? So they agreed to help her, and there they were walking in the (late morning) sun, with Mo by her side, and Edge and Larceny doing what they do best and staying in the background keeping an eye out for any guard trouble.
As she stopped to look at the schedule, a chill went through her as Diamond saw a poster on the board with the name Lollipop Secret, and a scarily good drawing of Diamond Tiara and her cutie mark. She looked at her rump worriedly, and tried to ruffle the fur to obscure it. With the hairs sticking up, it looked at least... fuzzier than it usually did. But it was hard to cover up a cutie mark, without a dress. Diamond wished she’d thought of that before she left.
Nothing came of it though. Whoever had put up those posters weren’t around, and nobody else seemed really impressed with them. It helped that Diamond’s face was next to another three posters of the same “Have you seen me?” so hers really didn’t stand out. She had no clue how other three fillies could have all stolen a bunch of money, but that was the only reason Diamond could think why anypony was even looking for them at all. So she just stuck close to Mo, and didn’t make eye contact with anypony, watching them out of the corner of her eye, and nopony accosted them, or came after them, and neither Edge nor Larceny gave the signal to bail out.
Soon Diamond stood before the train to Baltimare, the one passing by Canterlot, a nervous flutter in her chest making it hard to breathe. This was it. Everything she’d been working for these past months and now she had to get on that train and figure some way to sneak into Canterlot. After that, her success was ensured, but this was really the bottleneck of her adventure here. One more plan she couldn’t make until she was on that train, and one more time of being utterly, totally alone... not that she was thinking of staying with them, no way, nope. She... she wanted to do this.
“Alright, gimme the ticket,” Diamond said eagerly. Wordlessly, Mo hoofed it off to her, and Diamond carefully stashed it in her saddlebags. “All aboard!” the conductor called out. This was it. She... she could just run. Leave them flat hooved and penniless. But... how would she benefit at all, from that? It’s not like Diamond was planning on coming back here for a while, so those bits she stole weren’t gonna do any good just sitting there. Plus she looked into Mo’s somber eyes and he said,
“You sure you know what you’re doin’?”
And Diamond really wanted him to find those bits.
“When you leave the city on west 11th street,” Diamond whispered to him, “Go find the first road marker past the trees, and then go six trees to the north. One of the trees has an old burrow under it. Your bits are under there.”
Half the bits, at any rate. Couldn’t hurt to be careful about that.
She backed away from him then, a bit fearfully. He could—ruin everything now. He looked at her and... and he smiled. “Thanks, Creamy,” he said casually, then turned on his hooves, walking in the other direction away from her.
“All aboard!” the conductor called out again. A shaken, but eager Diamond Tiara went and ran aboard the train then. She didn’t really understand what just happened, but there was one thing Diamond knew. It made her feel good. Really really good about this whole thing. She was gonna take Canterlot by storm when she found the father of her foal, and maybe some time later she’d even stop back here to help those three out, just for old times.
When the train shuddered underneath her hooves, Diamond found a seat in a train car without many ponies in it. She felt nothing but relief as the convent, the hunger she fought, the city she hated, Peachy, and all that just receded away from her with every chug of the train’s powerful engine. It hadn’t been all bad. She felt wistful for having to leave behind the three stallions who robbed and raped her. But overall, it was incredibly relieving to be out of that strange place.
She had 2 days before they reached Canterlot, travelling across the great valley, and up the tall, lonely mountain on which the city was erected. 2 days to rest, and think of what to do. And the biggest question in her mind was, how was she gonna get past the guards and into Canterlot? Her ticket said Baltimare on it, but Diamond didn’t want to go to Baltimare. She just picked it as one of the trains that stopped at Canterlot. Her ticket was checked, punched, and got her safely on the train, but it sure wouldn’t get her safely off.
Now—a ticket that said Canterlot on it, that might work...
Diamond just wanted to sleep the whole time, but she had a lot of work to prepare. First she had to stop looking so... dissheveled and dirty, like she did. She spent a lot of time in the rail car’s bathroom, abusing the water tank to clean herself off as best as possible. It was cold and unpleasant, but Diamond was desperate at this point. She had to look perfect if she was going to pull this off. She scrubbed her flank until every streak of mud and grime was off of it, and she laborously combed her mane and tail, looking in the little mirror they had bolted on the wall in order to do so.
There was so much loose hair. Diamond was kind of worried, actually. But her head didn’t look any more sparse after she got the horrible itchy stuff all out of her. She guessed it was just accumulated. Diamond had never gone so long without grooming herself before, and now she only had what nature had given her, to do so. It was crude, painful, immensely relieving, and effective. Soon, Diamond’s hair fell naturally into separate stripes of brilliant color and lack thereof. She couldn’t have it permed of course, but she could make it dangle over her neck in a quite agreeable looking fashion. Diamond looked the picture of the adorable little filly, as much as she could tell from that little mirror anyway. And for the part of her that she left behind, well... it flushed into the cistern without too much trouble.
She checked outside from the bathroom’s cheap, sliding door, seeing nopony looking her way, and zipped out of the room. She felt a lot more pony when she was cleaned up like this, and didn’t have to feel apprehensive about approaching the food cart anymore, or at ponies giving her strange looks for being such a ragged looking common street urchin. The conductor hadn’t triple checked anypony else’s ticket, at least. It was pretty obvious Diamond stood out.
Well, now she looked great, and more importantly they wouldn’t recognize her. Diamond’s plan really hinged on the other ponies not being familiar enough with her to know she should be captured and taken away, but she wasn’t very worried about that. None of the train operators were the same ponies as the ones who foalnapped her at the train station last time. She had probably been nabbed by workers at the platform, not on the train itself. There was the wanted poster, but...
Diamond got some sweets at first, but then she found she really didn’t have the stomach for sweets. She wanted something salty. So she got some chips, and a wrapped sandwich, and... well, Diamond hadn’t exactly had any instruction in meal planning. She knew what she ate, but obviously it was servant cooked food that wouldn’t be sold, and beyond that... she just wasn’t sure. So she got whatever she thought would be good, and maybe some things that looked really tasty. She brought ...enough money with her, and she probably shouldn’t have spent so much on food, but it all looked so good! Anyway, she had less room in her saddlebags now.
While she was eating, she looked around to see who was going to Canterlot. It was pretty obvious when you looked at it. Canterlot was a high class city, full of rich ponies and princes and princesses. Diamond had heard so much about it, though neither she nor her daddy had ever been. Its towers were supposed to be sculpted from solid granite, and covered in ivory white limestone, with golden towers that gleamed in the sunset from all the way down in Ponyville. So, she just looked for possible marks who looked way too rich to be going to Baltimare. There weren’t many, but there were some. She spent most of the second day cautiously stalking them, observing their actions, trying to find some way to get at them.
It was towards the afternoon that Diamond had a stroke of incredible luck. She saw the stallion of a family of three: an adorable colt even a bit younger than Diamond, dressed in a smart suit with a floofy neck ruff, a green mare in an elegant gown with dolled up purple hair, and a caramel colored stallion with a striking blue mop of hair on his head and butt. They were pretty clearly going to Canterlot. The foal was chattering as such, at any rate.
Diamond’s stroke of luck came when saw the stallion look around furtively and sneak into the bathroom. He wasn’t just going to the bathroom. Diamond could tell when a pony was being sneaky. He was hiding something. So she went and peeked in the tiniest crack of the door, and sure enough, he was hiding something. His dick.
No, seriously. He was masturbating in the bathroom. Splayed out on the floor just stroking his massive throbbing erection. Diamond just had the best of luck sometimes. She practically had this script memorized. She slid the door open, and sauntered in saying before he could even so much as squeak, “Oh, looks like somepony is being naughty! And here I’ve caught you at it. I wonder, what ever shall I do with you?”
“Please miss I–I my family cannot know of this, please you must understand!” he said in that foppish accent of her more lucrative clients. “I–I’m not doing anything untoward I’m just... I’m sorry,” his ears went down guiltily, “You must think terribly of me, b-but stallions will sometimes—”
“Oh, I don’t think terribly of you,” Diamond said with a sweet smile, sliding the door to the little bathroom closed behind her with her tail. “In fact I... kinda like it.”
“W-what?” he said in shock.
“Don’t worry, I won’t judge you,” Diamond said softly, “I’ve always wanted to see a... stallion.”
He almost shot right out of the bathroom when Diamond’s tentative hoof touched his member. But she knew stallions, and the right touch there would leave him helpless to want anything but more.
Reaching with a hoof to stroke that tantalizing manhood gently, Diamond murmured only half insincerely, “It’s so warm...”
“Oh-m-miss you can’t—this is most—oh...” he stammered, giving into her minstrations with a sigh that was almost full of wonder. It was almost like he never did this sorta thing before. In fact, he probably didn’t, otherwise he would’ve known better than to let Diamond do this. She treated him as well as she could in the cramped quarters, stroking her soft velvety hoof up and down his stiffly turgid length. Her underside was starting to leak already, just the physical response from being there sliding her body against stallion cock. He couldn’t even speak when she looked at him with that look, just staring at what she was doing disbelievingly.
This was where Diamond was to lose control and present herself for him, sitting on his dick, as if he had a thing for resisting a mare’s advances. She... didn’t want to though. Her bottom was slick, but... it had really started hurting back there, just yesterday. Diamond shouldn’t have jumped back into her game so enthusiastically. Like it or not, she really did have to give her vagina a break. That didn’t mean breaking script though. If Diamond was lucky, and she had to bet on it at this point, she had encountered one of those stallions. The ones who don’t have to be giving you a foal, and just like their penis wet, squeezed and worshipped. So, looking up at him questioningly with big eyes, Diamond let a teeny little tongue out to probe experimentally at the head of his penis.
It tasted like a penis, go figure. Not that she was complaining at this point. Diamond was in her element when a customer was involved, even if he didn’t know he was being one. Her hesitant licks grew more confident as his breathing deepened, his whole body shuddering as Diamond tongued at his urethra, with both hooves sliding along the thick length that protruded from him. Diamond might have had a hard time with stallions on account of her size... and age... but there was one thing she was sure of. Diamond Tiara had a really big mouth.
He couldn’t hold back a strangled gasp as Diamond lowered herself onto his penis, mouth first. She hunched over his groin so that she could take more and more of him into her other hot depths. It was so exciting when she did it this way. She could still breathe through her nose, and her bottom felt quiveringly, thrillingly unfulfilled, but just the feel of him bucking against her needily was wonderful, and that strange hot thickness. Diamond had gotten really good at not choking on it, and slid it all the way to the back of her throat then further. She huffed hotly, and her nostrils blew out air just a hair’s length from his groin.
Then Diamond started bobbing up and down. Oh he loved that. It was pretty common for stallions to love that. Making them feel like they’re mounted up on a little filly just going to town. Diamond had to be wary that he didn’t try to jam her mouth down on it, but otherwise she had a nice big satisfying face full of dick. That’s not why she was here of course, but it was a nice side benefit.
Diamond might have been a little young, but she was totally experienced and world wise. Her daddy had helped her with these little schemes, where Diamond learned just why you only do things like this privately, in secret, and how you use that to hurt other ponies. “This is a very special opportunity,” he told Diamond that first time. “You’ve been paid in bits so far, and now you’ll be paid in blackmail.”
“What’s blackmail, daddy?” she had asked him. “It sounds icky.”
He laughed at that, a kind, hearty laugh. “It’s when you know a pony’s secrets,” he told her, “And they have to help you, or find themselves in trouble.”
He instructed Diamond just how to do it. He would handle the ‘payment’ as usual, but Diamond had a very important part in this. The stallion came in, who had been really mean to her daddy, and had to pay the price. Like Diamond was supposed to, she pretended to say no, and teased him even as he approached her hungrily, not caring about her, or anything other than what’s under her tail. “What are you doing? You can’t touch me there!” she said fearfully, raising her tail to curl over his nose as he moved his muzzle down between her hind legs.
“Mmm... the youngest ones have the sweetest scent,” he said indulgently, and Diamond tried not to blush at the compliment.
“That’s a no-no place!” she said, “You can’t touch me there, it would be wrong!” It was sort of like opposite day at school, where you said the opposite of everything you really meant. Diamond had to pretend that this stuff was wrong, so that she could get the stallion in trouble. So she turned her squeal of pleasure into a “Stop!” when he started licking her tingly little petals. Daddy wasn’t sure if he would do it, but he did, and Diamond was so glad for that. She tried to keep admonishing him, but that only seemed to egg him on, and soon she was reduced to nothing but bowed legs, hoarse panting, and an inside place that was taking her breath away.
He mounted on top of her then, and snorting, brought his thick penis to bear. Diamond felt it slapping against her, and jamming its fat flat tip against her entrance, and tried not to bite her lip. When she did that, sometimes she really did bite it. But everything went fine, as fine as it could, and Diamond for once had the freedom to cry out in pain as she was unable to stretch enough for him to do anything but hurt her. At least she had the wet thing in there, so it wasn’t too bad sliding against her strained passage.
Daddy’s instructions were very specific. He told her that lovemaking between a little filly and a stallion is illegal, but especially if there was penetration. That’s the bottom thing that Diamond did a lot. He told her that it was good for ponies to do that in private, but it was illegal, so if the guards ever found her, then the pony she was with would be in big trouble. And this time, that was entirely the point.
Diamond was told to wait until penetration had occurred, but she waited a little longer than that. It hurt so bad, so she didn’t know why she did it. Just to prove she could do it? There was a peculiar sense of satisfaction that welled up inside Diamond, as he stretched out every inch of her in there, as deep as she could go, and tears streaming down her face, she took as much as she could, as deep as possible. She thought about his penis being so deep in her hips, bottoming out there, moving in there, and just huffed needily, instead of calling out in pain.
She paused at that, puzzled with herself, and that gave her the reminder she needed. “My teddy bear is full of stuffing!” she shrieked, and the response was swift, and immediate. Diamond couldn’t turn around very easily. She could hardly bring herself to lift her hooves when she was so impaled like this. But behind her she heard a commotion, and through her tear blurred eyes she saw the shining golden armor of the royal guard come charging up to flank her, and the stallion who was doing this to her.
“I—I can explain!” his rough baritone called out in panic. He stepped back trying to pull out, but between her tightness and Diamond’s eagerness to hold on, all he accomplished was to drag her a short distance along the floor.
“You’re going away for a long time,” one of the guard stallions told him coldly. One of the others took Diamond’s front hooves in his own, and a third held the stallion steady, both pulling firmly until that awful, wonderful penis was out of her.
“He hurt me so bad!” Diamond cried bitterly. “I didn’t want him to, and he made me do it, against my consent!”
“You little twat, you set me up!” the stallion shouted in sudden realization, lunging for her, but the guards had a good hold on him. They dragged him, still shouting, out of the room, while Diamond stood there amazed at what she had just caused. She didn’t like him being so angry, and her bottom was sore again, but... she’d never have to see him again, right? So that was a good thing, right? They left Diamond all alone without another word, so she just went to the mirror and took a look at the damage. Winced at a little trickle of blood mixed with her juices. One day she was going to be a big pony, and would never have cuts in there.
But until then, she’d done a very good thing for Daddy, and Diamond had also learned how what she was doing was wrong and forbidden, but only if you get caught. Or pregnant, the sour thought occurred to her, as in the present moment, the stallion Diamond was sucking off peaked in desire. She used her tongue to tease his penis, trying to coax the semen inside to flow up its length and spurt out the end. It was so much fun to do this, but... well, Diamond wished she could just always use her mouth, and never had to worry about season.
But her underside just got so hungry for it! Diamond figured it was inevitable really, being a mother. Ordinary fillies didn’t feel that way, so they had more choice whether to have babies than she did. Even Diamond’s memories, about when she used her cunt’s incredible power to make royal guards enraged at her lover, they sort of made her wish she could fill it now, even as sore as it was. Diamond was ...bigger than she was back then, but still kind of way too small to be taking stallion penises. Diamond really hoped she’d get a growth spurt soon. Nowadays, even the other fillies in class were a little taller than— he ejaculated all over her face.
No, no it’s fine. Diamond Tiara meant to do that.