The Sheriff and the Princess
When Pipp decided to become Hitch's deputy for a limited time, she imagined lots of things.
She choose to help the Sheriff out because, well, his last deputy was about to literally starts a war against two tribes that were minding their business and couldn't care less for the Earth Ponies.
So, becoming Hitch's deputy was a decision she took out of generosity, because she genuinely wanted to help him out with everything she could. After all, Hitch has been alone for months, not to mention Sparky makes his duty as a Sheriff a complete challenge everyday as well.
However, the job turned out quite complicated as the weeks went by. The first few days were normal, and Hitch was definitely looking better thanks to her... But he eventually started to seem too distracted.
The paperwork wasn't a problem, since she could read entire articles of anything without falling asleep. Patrolling around wasn't a problem, either, thanks to the security cameras that her sister installed and connected to her phone so she could guard over the bay without having to get out of the station so often.
She thought at first she could have done something wrong that made Hitch get quite distracted and thinking on how to tell her without hurting her feelings... But one day, she finally discovered the actual reason.
The real problem about Hitch and why he's so distracted lately is that he simply stares at her rear day and night, sometimes trying to act like he wasn't doing anything, and sometimes without even pulling his sight away. When one of the latter situations happened is when she finally realized what he's doing.
At first, she only felt flattered, because she thought that he was having the same reaction everypony in the bay has whenever she look at her in general... But then it turned annoyed.
Every single time she's showing her backside to do whatever, Hitch gets hypnotized by it or something, because his sight never separates from her rear until she finally moves the sight away. It's even worse when she uses some leggings that made her feel comfortable at work.
She's been wondering if she should give Hitch what he wants (a peak of her ass, that is), but she has turned down that idea to herself. Why? Well, there's three prime reasons behind this.
The first one, and the one she considers the very reason she could never see Hitch ever again if she does it with him: She has a crush on him, ever since the very day they met. Well, maybe a bit later on, like a month or two, but still, she likes him a lot. Probably also one of the reasons why she wanted to be her deputy.
She likes Hitch by who he is: A helpful pony, a very kind one that despite having a charm that made him a chick magnet, he never ever stopped being himself with anyone. No matter how little the task seems to be, Hitch will be there to help you out, to make sure you feel happy and safe while he's around... That's what Pipp loved from him.
Of fucking-course that he's handsome and sexy, but that's just a plus. His personality, his dorky attitude, his sometimes lame sense of humor... It actually made her laugh and fall for him even more. Hitch was everything Pipp could ever want and even more. However, all of this sums up to the reason why she can't give Hitch what he's craving for, at least not yet.
The second reason is that she knows she'll avoid Hitch as much as she can if anything spicy ever happens between them, and he'll probably do the same. She can't let that happen, she can't loose her crush.
The third and final reason? Their friends in the Crystal Brighthouse would eventually find out, and of course, some tension could grow and make things really bad for her, but hr sister would probably take ti the worse since she suspects she also has feeling for Hitch. Not that she hates her or blames her, though.
As for Hitch? Well, he's a man, is in his nature to stare at said zone even when he doesn't want to stare. As much as he tries to ignore it, Pipp has a very nice plot, one he simply can't ignore.
If this isn't enough, Hitch also has some feelings for the young princess. This goes beyond her rear, though, but it is a very nice one he'll slap if he didn't respected her. He also loves her cheery and energetic personality. When you take the time to meet Pipp out of the phone? She's wonderful.
He has tried to approach her in more than one occasion to ask her out on a date, but he always feel like a coward at the last second and simply turns around without saying a thing, much to his own disappointment.
Hitch has never really feared anything. No matter who he was with, he always stayed true to himself: Handsome, helpful, sometimes with a big ego, but he always remains the same kind stallion that will help you no matter what. He also flirts a lot with every mare, although that's just because he likes to be charming.
When it comes to Pipp, however, he becomes a completely different guy: He sweats, stutters, his mind goes blank, his cheeks burn red, and his heart beats so damn fast that he can barely stay calm.
Hitch's been crushing over Pipp for the past year, and ever since, he tried to be close with her from time to time... The most she's been able to interact with her, though, is when they have reunions with their friends. Out of that? He always talks with Zipp and Sunny, but the other three of his friends... He barely talks to them lately.
The one that hurts him the most he has talked the less with is, obviously, Pipp, mainly because her agenda is always busy with Mane Melody, livestreams, concerts, and planning out her stuff for her fans.
Hitch thought he'll never be able to spend some more time with his crush... Until a few weeks ago, that is.
Since taking care of a baby dragon like Sparky that has way more energy than he can deal with (for his eternal annoyance), he gets exhausted constantly, and he always delays more and more paperwork and patrols because of the baby dragon, who's legally his son at this point.
While Hitch wouldn't trade Sparky for anything in the world, he did wished to get more help out in the station... And just like the angel she is, Pipp came to his rescue with an offer.
She'll be his deputy for a while until his schedule gets back to normal again. She'll help out with the paperwork and the patrols, while Hitch simply deals with Sparky and takes care of him. She'll even help him if she finishes part of the job in time.
Hitch didn't even thought about it and accepted the deal. Now, thanks to Pipp, the job around the Station has been easier, and he always enjoys entering and see her there, on the deputy desk.
Yet that enjoyment may have gone too far, because sometimes, when Pipp's backside is exposed, he can't help but stare down at her rear. Her ass is pretty big, and he has dreamed on touch it at least once in his life before dying. He has also imagined how could she look without her pants nor underwear over.
And let's not even talk about her tits. Gosh, her tits looked like giant balloons, and the few times he has seen her with more provocative clothes, he has seen those big balloons better than ever.
But Pipp's body is not the only reason he likes her. True, she's sexy and hot as fuck, but the fact that Pipp seemed to want to be as helpful as him, to cheer your mood when you feel down, to make you smile even when you have no reasons to... He has lost count of how many times something silly comes out from Pipp's mouth when he's feeling grumpy during the job, and her comments always make him smile.
She was the light of hope he always needed when he was down at work... An angel that wasn't going to let him be in a bad mood, and that didn't rested until he was at least smiling. Her will to not give up so easily is another details from her he really likes, and he even admires it a lot. Now, if only he could tell her how he feels about her without sweating so much...
None of them dare to make a move because none of them want to ruin their friendship, and they also know that the whole deal of Pipp helping Hitch wouldn't work anymore. However, none of them can imagine that things are gonna get spicy for the two of them, more sooner than later...
One day as usual, Hitch entered to the Sheriff Station, feeling completely exhausted.
Pipp was inside already, and she just finished doing the stack of papers she purposed herself to finish today, closing the cabinet and then smiling as she saw Hitch entering the station.
"Hey, Hitch!" She greeted happily. "Or should I say 'boss'?" She asked playfully.
"Ha ha, so funny," Hitch rolled his eyes with a little smile. "I see you just finished with your job?"
"Yeah, the last stack of papers for today has been recently done." Pipp replied with a proud smile, then she lay on her desk. "So, Sheriff. How was your patrolling around the town? Any adventures as of late?”
Hitch smirked at the mare. "Doing Sheriff duties, as I always do." He brushed back his aquamarine hair back in a prideful manner.
Pipp giggled at his attitude. "Oh yeah? Like what, Mr. Trailblazer? What sort of Sheriff duties did you do?"
The tone of her voice, the nickname... it caused an awakening in him, and he definitely felt butterflies in his stomach. Was this flirting? It couldn't be anything else. He has done it before, true, but it has never been like this. When somepony flirts back, is like if his brain shut down and he didn't know what to do anymore.
Hitch laughed a bit nervous while scratching his neck. "Ah well... Posey requested my help. Something about a creature infestation in her garden."
"Hmm?" Pipp raised an eyebrow. "I thought you were a Sheriff, Hitch. Not animal control."
"Can animal control have a pony that speaks to animals? I don't think so!" Hitch replied, sticking his tongue out at her.
The tension between them was suddenly growing, but Pipp still snickered at his attitude. "Did you get the critters out?"
"Of course. Have I told you I'm good at my job?" He smiled proudly and huffed his badge.
"Hah." She scoffed, rolling her eyes. "You don't even need to tell me, I can see right through that big ego of yours!" She managed to get closer to the Sheriff and look at him seductively.
Of course, Hitch stepped back by instinct and tried to sneak out, but ended up cornered against the wall, and so, he looked down nervously at Pipp while blushing, as she just smirked mischievously.
And then, she made her fingers walk over his chest before stopping on his badge and snatch it away.
"This thingy boosts your ego a lot, you know that?" Pipp asked with a mocking tone.
"Hey! Give it back!" Hitch replied with a slight chuckle, as he tried to snatch the badge back from her.
Yet Pipp only giggled and stepped back while keeping the badge away from Hitch, and the Sheriff only slightly chased her around the station while she flew around in a playful manner. Yet the game quickly came to an end when Hitch tripped and pulled Pipp down to the ground, making them both yelp startled.
Pipp ended laying on the ground, while Hitch almost fell on top of her if he didn't stopped himself from the fall by placing his hands in the ground to keep his balance the best he could.
When he recovered his senses, though, he stared at Pipp's eyes, and Pipp stared back. They both stared at each other for a good while they blushed hardly. Pipp's beauty seemed to reflect even more now that Hitch was so close to the young princess, and Hitch looked so handsome to her she swallowed hard.
Their hearts were bumping like crazy, almost as if they would get out of their chests at any second now. Being in love, romance, resisting the impulse to kiss each other... It was all difficult stuff, won't you agree?
Eventually, though, Hitch snorted and grinned. "You took property of an upper authority's important item, ma'am. Anything you've got to say on your defense?"
The tone he used, the way he was looking at her, it made Pipp's blush increase and her heart melt. How could This guy be so sweet and dork, yet so fucking sexy and handsome at the same time? It's something only those ponies like Hitch Trailblazer could accomplish.
"...Guess you caught me, Sheriff..." Pipp replied with a playful smirk. "What are you gonna do now?"
Hitch suspected which direction this was taking... And he didn't disliked it, so he simply went for it already and locked lips with the princess', making her eyes shot open in surprise and confusion.
Out of all the things she thought that Hitch would do, kissing her was definitely not in her mind. Not that she complained, though, because she eventually returned the kiss and wrapped her arms around his neck, while Hitch himself wrapped his arms around Pipp and lift her up, with Pipp herself flapping her wings.
After that, Hitch sat her down on the desk and stared at her eyes for a while, before eventually brake the kiss and smile, while they both panted for breath, but Pipp smiled back at the Sheriff.
"...You didn't... planed that... did you, Hitchy?" Pipp asked with a mischievous grin.
"No..." Hitch replied honestly. "I just wanted to do what seemed the best at the time."
"Well... You're putting me in a mood here~" Pipp said while bitting her lower lip and grinning even more at the Sheriff.
Hitch arched a brow. "You want me to... you know... Make love with you? Because if that's the case, there won't be a turn back for us. Neither as friends, nor as Sheriff and Deputy."
"Hitch... I've been wanting this for way too long." Pipp decided to confess, also caressing Hitch's cheek with a hand. "Sure, I fear the outcome of what will happen after we're done... But I've been afraid for a whole year now. I don't want to be afraid anymore!" She place her other hand on his other cheek and hold him tight while looking at his eyes with love. "I just want to be taken by the stallion I'm in love with... And that's you, Hitch Trailblazer."
The Sheriff's eyes widened in surprise, and his heart jumped in excitement. "...I've been wanting this for the past year, too." He confessed as well, grabbing one of her hands with his and gently kissing it. "I've also been afraid. To tell the truth, I still am. How our friends may take this sudden change on our relationship if we get to something concerns me a bit, for example... But you're right. I don't want to be afraid anymore, either... I just want you, Pipp." He placed a hand on her cheek and the other one around her waist. "I want a night with the beautiful mare that captivated my heart and made me fall in love."
"Aw, Hitchy..." Pipp said with a smile, feeling touched by the Sheriff's words. "I wouldn't like anything else, but––"
"If you worry for Sparky, he's with Izzy, being dragon-sited until I go for him." Hitch replied with a smile. "As for the Station, well..." He went over and pulled down the Station's windows' blinds, then locked the door with key, and then looked back at Pipp with a mischievous smirk. "Nopony's gotta bother~"
Blushing by the tone he used, Pipp shook her head and then smirked as well. "My my, Sheriff Hitch! Sounds like you want to punish somepony for stealing your badge~"
Hitch approached her and pulled her closer by wrapping his arms around her, but also holding her chin with his fingers. "Eh, I don't really care for that right now. I just want to take this princess here for me, and me alone."
"You're a very bad Sheriff~" Pipp teased, locking her lips with Hitch's again, and this time around, they went all out on each other.
Their kiss was romantic at first, but it turned aggressive as both of them began to push their tongues together in a battle. Hitch even went ahead and grabbed Pipp's breasts with his hands, squeezing them and making her moan while she placed a hand on his chest and lowered the other one to his crotch.
Down his pants, she could feel the bulk already, and she was impressed just by feeling it from there. She wasn't sure how big Earth Ponies truly were, but she was about to find out.
"Who's the one excited now, hmm?" Hitch teased her with a smirk.
"Don't blame me!" Pipp rolled her eyes with a playful snort.
After saying that, she got down of the desk and pulled Hitch's pants down, and then his underwear... Which made her gasp with wide eyes and go wet on her lower zone as she stared at a semi-erected Earth Pony cock. To say it was bigger than a Pegasus dick was being humble... This was bigger than she expected.
"Oh. My. Gosh..." Pipp said with a nervous smile, as she grabbed Hitch's cock with her hands, which did made Hitch grunt a bit startled, probably because it's been a good minute since the last time he had sex. "...Um... Hitchy? Are Earth Ponies this... gifted, or is it just you?"
"I'm just average size... At least among my fellow Earth Ponies." Hitch replied.
This made Pipp gulp nervously while her eyes went even wider. "A-Average... I-I see..." She was really nervous now, but she's been dreaming about this for a year. It was not time to back down. "Well, I didn't thought I'll need these so soon."
Pipp removed her pink blouse, followed by her white bra, throwing both of them aside and then placing Hitch's member in her generous cleavage. As she began to pump the Sheriff with her breasts, the tip would pop out of the top affording her a chance to lick his crown with her tongue.
The double stimulation of her soft tits along his shaft and the licking of his tip was definitely getting to him as he grunted, and let forth a lust fueled moan.
"Are you enjoying this, Hitchy?" Pipp teased him with a smirk while biting her lower lip. The response she got was Hitch's cock getting fully erected, which meant that only half of it was covered with her tits now. "I guess you do!" She giggled.
After this, Pipp pulled her breasts away and dove directly on his dick, instantly swallowing half of it with her mouth. Making loud slurping noises, she bobbed her head up and down while she sucked. She moaned, finally tasting and feeling Hitch's cock in her maw after dreaming about it for a whole year.
"Holy shit!" Hitch thought, as he placed a hand on the back his deputy's head, giving her some encouragement to keep on sucking and fellating. "How could I never imagined that she'll be this good of a cocksucker?!"
Meanwhile, Pipp was feeling completely satisfied by tasting her crush's shaft. If Zipp ever finds out that she's sucking Hitch Trailblazer's massive cock, she'll be death. But right now? She couldn't care less. All that ran through her mind right now was making him cum down her throat.
Suddenly, Pipp moved a hand to Hitch's balls, rubbing and rolling them around to coax her 'boss' to climax faster.
"Oh, fuck, Pipp!" Hitch moaned. He firmly grabbed Pipp's head then started face fuck his deputy, deepthroating her in the process.
Startled by the sudden throating, she gagged on his hefty phallus. Pipp still kept stimulating his member, trying not to cough. He kept going as she gagged again.
Hitch pulled her head down around his cock hard, and with a final and mighty thrust, he soared past his limit. A torrent of hot seed gushed down to Pipp's stomach whether she was ready for it or not. She was definitely not. Pipp gagged and started to choke at the large deposit being delivered. She tried to push away to get some air, but Hitch's grip was stronger. She had no choice but to try and relax her throat muscles until the flood ceased.
After he Hitch's member finally stopped shooting ropes of cum, he let go of her head. Pipp immediately pulled back, gasping loudly taking lung-fulls of air. There was so much cum that she coughed some of it up
"A-A warning would've been nice, Sheriff..." Pipp complained a bit with a slight frown.
"S-Sorry, Pipp..." Hitch apologized with a sheepish smile. However, he was still hard, to no one's surprise.
"Hmm... I think we need to take this all the way." Pipp said with a smirk.
"Yeah... I agree," came Hitch's response. Then he lifted her from the ground.
Her look of surprise changed as she saw that the Sheriff lifted her up high. She caught on to what he was doing and flapped her wings to stay in the air and wrapped her legs around Hitch's neck. He immediately got to work on his friend's lower lips. He worked his tongue fast and furiously, then slipped it to her insides.
Pipp started to moan loudly in response to the pleasure of her crush's tongue on her pussy. With the sudden and intense stimulation, her wings were starting to go stiff. She buried her fingers in his mane and held on for dear life. Her wings were starting to betray her more and more as Hitch kept going with gusto.
His movements were careless, and wild. His tongue moved around Pipp's flower like a starving feral animal desperately looking everywhere in search of sustenance. And, of course, each movement only made Pipp moan louder and louder.
As Hitch kept licking, not thinking about it, he also gripped his tool and started working it at fast paste.
Somehow, her wings were still flapping enough to keep her on Hitch's mouth. And then, he licked a certain spot that made Pipp cry out in utter bliss. Her legs trembled and a gush of mare juice splashed across the Sheriff's face.
Her climax was cut short, because she began to fall back towards the ground. Hitch's reflexes made sure to catch her bridal style. Realizing that she was safe, Pipp rested her head on Hitch's muscular chest while panting heavily recovering from her orgasm.
This was her first time realizing that Hitch has removed all his clothes as well as her. He had nice muscles. She has seen them before, and has masturbated with some pictures of them, but seeing the actual thing was making her go wet again.
"Hope you'll recover, princess, because we're far from being over~" Hitch teased her with a smile.
"Oh, I'm very aware of it, handsome~" Pipp replied back with the same smile and a loving gaze, then locked her lips with the Sheriff's.
He reciprocated the gesture, caressing her cheek with a hand, and then gently placing her to lay on her belly over his desk.
"Ooh, going for it already, hun?" Pipp teased once more, although her pussy was dripping wet, pretty much begging to be filled with a male's seed. "We both know what's next, Hitchy. So don't hesitate and fuck this princess!" She exclaimed, using a hand to open her pussy and present it in all his glory to her crush.
The sight gave a twitch to Hitch's manhood. It grew harder, and he was drooling for her. Lubricating his dick with a bit of saliva, he entered easily inside of Pipp, making them both sing out loudly in pleasure.
"Shit... I've been dreaming about this for months!" Hitch exclaimed in-between moans.
"M-Me too, hun... Now go on, rut me!" Pipp begged, tired of Hitch playing around with her.
"That's the plan." Hitch replied, grabbing her boobs and squeezing them.
Not wanting to wait a bit longer than he already has, Hitch fucked Pipp's pussy hard and fast, smashing his hips against his deputy's cushiony ass. She was not holding back her cries of pleasure each time his member surged in to her. He continued to slam in to her and Pipp's unfiltered moans let both of them know she was enjoying this a lot.
Hitch was enjoying it, too, and as he kept up the frantic almost needy pace of his thrusts, he squeezed Pipp's breasts again, as best he could, even though their large size spilled over both sides of his hands. Then he found her stiff nipples and tweaked each of them. Pipp reached another level of pleasure and moaned like a whore. Soon the pistoning pleasure had her tongue hanging out. It flopped around crazily which each thrust.
To spice things up, Hitch grabbed one of Havens legs and put it behind him. The new angle allowed his throbbing cock to reach just a bit deeper in her drooling pussy. The new position allowed him grab hold of one of her breasts. He latched on to the nipple with his mouth, sucking and licking with force, while the princess wrapped and arm around his neck.
"Oh... shit... Hitch!" Pipp moaned each word louder as every thrust forced a bit of air from her lungs. "You better fill my womb or you'll be making the next two months of paperwork alone again!"
Hitch knew she was joking, but you can never be to sure, so he took her words to heart and began to pound harder and deeper. His deputy began to roll her eyes back and moan blissfully as she was being fucked hard by the Sheriff. They both could tell each of them were getting close. As he kept up the fast pace, it wouldn't be long now.
Finally, with one definitive thrust, he came again, shooting a massive load inside the princess. She came again when she felt his white and hot seed flooding her womb. Her climaxing scream continued, and continued, as she felt each rope of searing heat explode in to her depths.
Hitch felt bliss by finally filling his crush's womb after dreaming about it for such a long time. After the last dregs of cum were milked from his cock by Pipp's clenching pussy, he pulled out. A deluge of baby batter spilled from her used and puffy lips, dripping to the floor.
Once their shared exercise was over, they both panted heavily, then putted their foreheads together and smiled after being done. They truly didn't regret any of what just happened between them, and they even weaved fingers.
"...Well... I guess this makes you my marefriend, doesn't it?" Hitch asked after some seconds of silence.
"Only if it makes you my coltfriend." Pipp replied with a nervous smile, also blushing a bit embarrassed because of being naked. The impact of what just happened is just kicking, but that only made Hitch find her more adorable than she already is.
"Pipp, I meant what I said before we even did what we did." Hitch said, caressing her cheeks with his hands again. "I'm in love with you. Genuinely in love with you. I wanted to do it with you, true, but even if we didn't made that? I would've shown my feelings any other way to prove you I'm not kidding."
"Oh, Hitchy..." Pipp replied, once again feeling touched by her new coltfriend's words, even kissing his lips for a sec. "I can't believe this is really happening..."
"Me neither, but here we are!" Hitch joked, making them both laugh a bit. "My only concern is how's everypony else going to react. You know: Our friends, your Mom, your sister, your fans, my grandma, Sparky..."
"We can worry about them later, Hitchy." Pipp assured him with a smile, pressing her breasts against Hitch. "Now, how about we make some more time together inside here, huh?" She passed a hand over his still erected dick. "I can tell you're in the mood to keep going~"
Hitch snorted and kissed her again. "As long as I can be with you? I don't really mind, Princess~"
THE END
Author's Note
(Almost) Three stories in a row? New record! And it's gonna be beaten soon, too!
