Harsh
The train's horn roared deeply and started moving with a jerk. You pat your filled stomach with a contented sigh, lunch was amazing. It's the summer of junior year and you're working, completely lame right? Not at all, being the assistant of the Equestria Games Inspector is the easiest and best job ever! Well, it's an internship, but that doesn't matter. At first, you were aggravated that your parents made the choice for you. But that thought soon perished when you arrived at Manehatten for your first day. You were walked in by your parents, to your annoyance. You're an adult, you don't need them to hold your hand! Legally, you are an adult. But, you are required to stay at home for two more years to practice your special talent so you know what you're doing when you do leave. Equestrian age laws are odd- instead of having to be a certain age to be a legal adult, you're an adult as soon as you get your cutie mark.
The office, much to your liking, was filled to the brim with attractive young mares. Not too surprisingly on account of the male-to-female ratio being 1:3. Another noticeable fact, there was a shocking lack of unicorns. You felt like a superstar when they asked what you could do. Since the job would mostly be writing down notes and anything else you showed them your multitasking. Your magic writes down one thing while you do anything else they ask you to, the demonstration turned into a game when people around the office asked you to write down things while running, jumping, juggling, doing five-finger-filet with a letter opener (didn't work so well), or anything odd and distracting. Long story short, you got the job. All these pretty mares you had the chance to work with and you got... her. Ms. Harshwhinny. You felt like your hopes were stabbed by a rusty fork. The oldest, most experienced mare in that profession. She wasn't ugly, just... anyways.
The first few days were not great, you were still a bit bitter about getting stuck with her. Rude comments, defiance, and general being-an-assholeness were the only things that you would say and do. That was when the season was slow, now it's picked up and business owners are lining up to have you and Ms. Harshwhinny judge their products so they could be picked to sell at the Equestrian Games. Most of the jagoffs from school are sitting at home, playing video games and being lazy, while you're halfway across the world enjoying the best of the best, all for a little paperwork! There were some things you missed about home though, privacy mainly. The ability to walk around the house in nothing but a pair of boxers was a big one. All in all, this is the best summer vacation you've ever had and it's barely only halfway done!
You are torn from your thoughts when something hits your head; a wadded piece of paper. You look at the only other person in the train-car and smile sheepishly, how long has she been glaring at you?
"Did you hear any of that?" Ms. Harshwhinny asks redundantly.
"No, sorry, I was kinda daydreaming. Could you repeat it?" You ask, pulling some paper and a pencil out of your bag with magic.
"Forget it." She turns away from you with a huff. She's been so irritable lately. She wasn't too happy about her co-worker the first few days either, arguing about how she didn't need to babysit and would work better alone. Along with yours, her attitude improved as well. You could consider her a good friend, even if she is strictly business and addicted to work. One of your proudest achievements would have to be almost making her genuinely laugh. Your jokes are great, if a bit off-color. Unfortunately you were unsuccessful and merely made her get one of those weird faces you get when you try to suppress a big grin. After some moments of silence, you spoke up.
"What's wrong?" You look at your friend.
"Nothing."
"C'moooooooooon." You whine, making your famous puppy-dog eyes. She turns, sees your face, and frowns.
"I said, nothing."
"I'm not going to stop bothering you until you tell me, you know that right?" You cross your arms.
She sighs and looks away. "All right, maybe later." You yawn, risking a stretch. Your stomach was packed, lunch was given to the two of you by Stalliongrad's finest restaurant for a chance at selling at the Games. You could feel a rising food-coma creeping it's way all around your body. "I'm going to go take a nap, wake me up if you need anything." You stand and march over to one of the built-in-beds and crawl into the lower one, pulling the privacy curtain closed behind you.
~~Two hours later~~
You rub the sleep from your eyes and pop your knuckles. What time was it? You pull the phone from your pocket and press the home button.
4:23 PM.
The sound of scribbling fills the train-car, Ms. Harshwhinny is writing something. You roll out of the bunk as gracefully as a pig on rollerskates, and fall flat on your face. "Good to see Ms. Sleeping Beauty has finally awoken, come help me work on this." Ms. Harshwhinny orders. You stand and dust yourself off, wincing at the quickly forming bruise on your cheek. She hands you some papers and you finish them within minutes. Another stack, and another after that. An hour flies by and you've completely used up two pencils. "When we get to Trottingham we will be meeting the owner of the milk farm. Supposedly the owner is an earth pony who makes milk herself, and runs a rather large farm by herself. I want you to take notes on the quality of the cows, conditions of areas in which they live, and anything else peculiar." You nod.
"Yes ma'am."
"And another thing, the owner seems to have very large... breasts, try not to stare or comment on them. I know how young men are with breasts." She stares at your blank face.
"To be honest, I prefer small breasts." You stare back. "What, you think I'm some kind of sex-crazed psycho? Not once have I tried anything on anyone, but I've seen you take second glances at the guys back in Stalliongrad, Manehatten, Hayston, and others. So don't ask me to control myself." You smile slyly, she puts on the face of a businesswoman, but who knows what's beneath it. You can see the gears turning in her head, she opens her mouth for a rebuttal, but closes it when nothing comes out. "So... you wanna tell me what's bothering you yet?"
"Nope."
"Damn." You snap your fingers. "If you tell me I can probably he-" You're cut off.
"You wouldn't understand." She simply states.
"C'mon, you know I'm smarter than I look." You chuckle, so stubborn she is.
"Okay then mister genius, it's estrus season, okay? I'm just a little worried that with the smell of hormones floating around me and any other mare we pass that I'll get assaulted because some stallion has no self control."
… well then.
"That is completely ridiculous. No stallion would ever do that, you know, 'cause gelding. And plus, why would they assault you?" Dammit, that sounded better in your head.
"Oh, am I not pretty enough to be assaulted?" She sneers.
"No, that's not what I meant, you're pretty, just... nevermind." You sigh. You would scold yourself later. Admittedly, she was pretty. In that older women sort of way. Now that she mentions it, it does smell odd.
"I need to use the restroom." She suddenly blurts out and rushes off. There was little talk of estrus in health class, but your teacher did say frequent urination was a symptom. You run your fingers through your hair idly in the silence, reveling in the fact that you're an idiot. This is going to be a long hour. You decide to pass the time drawing, you weren't very good but you weren't bad either. You rifle through your nearby briefcase, and fish out some paper and a couple pencils. You decide the Princesses could be a good thing to sketch.
Ms. Harshwhinny returns to her seat, still looking agitated. You say nothing, and neither does she. It's probably better you just forget about it for now. Aside from the occasional bump of the train on the tracks, the room was silent of all noise aside from your pencil scratching the outline of Luna's wings. Ten minutes pass, then twenty, thirty, forty, and finally, an announcement comes through.
"Attention all passengers, we will be arriving at Trottingham station in twenty minutes." The speakers blare. You look over at your co-worker again, she appears to have dozed off. You put your now-completed sketch away, and go into the restroom to fix your frizzy hair. When you return, Ms. Harshwhinny is cleaning up the train-car. You join her. Within minutes, the car is clean and pristine. Magic rules.
"So..." You start, trying to find a topic. "What did you say the Milk-mare's name was?"
"Right, I suppose I didn't tell you. Her name is Milky Way." Ms. Harshwhinny answers in her ever-present business voice. You wish, that for once, she would show a little emotion. "It is a little unprofessional, but please do try to speed everything up. I am already starting to cramp."
"I'll try. Do you want me to look for anything to try and help you? Painkillers, muscle relaxers, etcetera etcetera?"
"No, I'm sure I'll be fine." Ms. Harshwhinny winces. Is estrus really that bad? Who knows? You're a guy. You have a penis.
The wheels on the train screech sharply as the train slides into station. Here you are, in Trottingham. You grab Ms. Harshwhinny's bags and follow her out of the train. The town's main street was busy, as if someone told them 'hey, there are people coming today on a schedule so let's be in their way'. After navigating the streets and stopping for directions twice, you both arrive at the gate to the dairy farm. A quick stroll leads up to the main door and into the office building. Ms. Harshwhinny asks the receptionist to call her boss and tell her that you both had arrived.
Ho-ly SHIT.
ARE THOSE BREASTS!?
You have to stop yourself from gasping. The Milk-Mare's rack was gargantuan. Both bigger than your head. Gotta be natural H-cups. The business flies by in the office, when the subject turns to more sensitive matters you are sent with Ms. Way's PA to tour the barn and milking areas.
"My name is Berry Garden, what's yours?" The PA was a bouncy girl, full of energy. Red hair, freckles, tall as holy-hell. You guesstimated her height to be around 6'8-6'9. You tell her your name. She walks the both of you over to a very classic looking, large barn. The insides were spotless, as far as barns go. The cows were clean, happy, and healthy too. Nothing much to take note of. You both continued to tour until hours had passed. When it was time to go both you and Miss Harshwhinny started back towards the train. This was going to be a long month.
~A week later~
The situation's only gotten worse on the train. Miss Harshwhinny is too stubborn to take any pain-relievers and is pretty much bed-ridden at this point. After another non-productive day, you decide just to go to bed. But not before doing some reading on your phone. You jump slightly when your privacy curtain is ripped open. It's Miss Harshwhinny.
"Get out." She says, dragging you out of the little room.
"What’s wrong?" You ask. She says nothing. "Am I in trouble?"
"You're not in trouble... I need your... help." She says, blank-faced.
"With what? Surely whatever it is can wait until the mor-" You stop dead in your tracks when you feel her grab you below the belt.
"Are you really that dense?" She laughs briefly. "I've been patient. I've tried luring you. You must be blind! It's time I take what I need!" She pushes you onto a nearby couch.
"Miss Harshwhinny..." You're taken aback. If she would have said something sooner.
"Is that a yes?" Her tone suddenly turns to pleading.
"Um, just... let me think about this." She backs off a little bit before going into the restroom. You decide to go for it. You would be doing her a huge favor. She comes back out of the bathroom looking completely different. Hair down, only bra and panties on, and giving you the bedroom eyes. You stand, taking a breath. "I've decided." You close the distance between you and her and place your lips on hers. She recoils.
"Oh don't treat me like your first girlfriend! I need you to fuck me!" She pushes you onto the ground roughly. By the time you know what's going on, you're half naked.
She rips, rips, your boxers off and grabs firmly onto your member. A chill runs up your spine as you realize that this is fucking happening, it's real. She strokes you steadily in silence, and not even in moments you're hard as rock. She then crawls up your chest, and places the opening of herself on your tip. You both shudder in anticipation. Without wasting another moment, she slides down and takes the entire length inside. Your eyes widen at the feeling, warm, tight, and wet. She moves up and down at an agonizing pace, savoring the experience to its fullest. Simultaneously torturing you. Her sliding quickly turns into a sloppy, rhythmic bouncing after the train hits a particularly hard bump. Already, you could feel yourself reaching your peak, due to your lack of experience.
"M-iss Harshwhi-... I'm close." You manage to get out with a moan.
Instantly, she locks eyes with you. "You do not DARE cum without my permission!" She shouts, picking up speed. The walls of her womanhood clenched tight, trying to persuade you to give in. You are walking on nothing but a thin thread. To keep yourself from blowing a hole through your boss, you think of nothing else but the most vile and disgusting things your mind could possibly come up with.
Dead babies, vomit porn, scat, Rarity, my 3rd grade math teacher... You repeat in your head. Suddenly, you realize the best part about this situation. How much she is loving this. It's all about her. To her, you're just an object. Nothing more than a living fuck toy, to be battered and beaten at her very beck and call.
And damn if it wasn't hot.
Miss Harshwhinny calls your name. "You can cum! You can cum!" She is practically screaming, moaning and panting like a whore. Her inner walls clench immensely hard against your manhood one last time, the ripples and contractions immediately causing you to buck your hips up. Hilting inside of her and releasing a pent-up wave of hot, potent and copious baby batter into your employer. Letting out a silent scream, you feel as though you’re pumping your balls dry. It feels too damn good, too damn good to be true! Your shaft is throbbing violently with each spurt, balls clenching, hips bucking, knees shaking, back arching! Hot mother-FUCKING DAMN it was amazing!
Once you were done, you realize that you came an ample amount, which painted your crotch white, and her upper legs too. She then flops onto you and passes out. "I love this job..." You put your arms around Miss Harshwhinny, and drift off to sleep.
~The Next Day~
You both wake up at around the same time, and somehow managed to pry both of yourselves apart. Since she was still on top of you, and since your engorged (but somehow limp), sore manhood still lodged inside of her.
The train would be stopping in Ponyville to check the Apple Family’s orchard, and the bakery. To save time, you both decided to shower together. As much as you wanted round two, you both were on a tight schedule today and didn't have the time to spare. A million thoughts were racing through your head, were you a couple now? Was this just a one-time thing? How will effect your future as her PA.
You laugh briefly, seeing how you work as her 'personal' assistant.
The shower wraps up quickly, seeing how neither of you wanted to stay in the tiny train shower for longer than you had to. After getting dressed, combing your hair, brushing your teeth, and completing every hygienic task known to man you still had ten minutes to spare. Taking a swat, you lay your head back and rest your eyes. For a moment, all you feel is the train rumbling and bumping on the tracks.
Then the seat depresses. You hear Miss Harshwhinny getting your attention.
"I would just like to thank you for helping me last night. I realize that it was a weird situation to be in but I-" You cut her off.
"You don't need to explain yourself, I had fun and you were great. And, you know, maybe this could become a regular thing." You say, trying not to sound creepy. She smiles and places her hand on yours.
"I would like that."
~Ponyville~
The day went by incredibly fast, leaving an extra four hours of time to goof of and relax before having to board the train once more. Questions still bogged your thoughts. In all honesty, you kinda wanted this to be a real relationship, not just a 'friends-with-benefits' sort of deal. In an episode of quick thinking, you know how to test how she feels. Twilight Sparkle, the town's librarian, was walking by in a short skirt. Without drawing unwanted attention you rubberneck for a view of her rear. When you look forward again you see Miss Harshwhinny glaring at you.
Success.
You both continue walking into the center of town and decide to grab a seat at the local cafe. In the middle of some dull smalltalk, Mayor Mare joins your table to chat about the possible location for this year's Equestrian Games.
Why not have some fun? You smile devilishly. Years of feeding the dog food under the dinner table has let you master the art of under-the-table-arm-stealth. Using Mayor Mare's joining as an excuse, you scoot closer to Miss Harshwhinny. You weren't even listening to the Mayor, who was pretty much talking in her own little world. Moving your hand discretely, you manage to undo Miss Harshwhinny's pants button and slip your hand inside. She is hissing at you ever so slightly without trying to seem suspicious in front of the Mayor. You begin rubbing her lower lips ever so gently while trying not to crack up at her facial expressions. Ever so gently you drag against the delicate, swelling mound.
"What do you think of my proposal, Miss Harshwhinny?" The Mayor asks. Miss Harshwhinny takes a breath as to answer.
And then you go knuckle-deep. Her face contorts into a variety of expressions before she tries to give an answer. "I tHINk this c-oooul-d be a nice SPOT to h-ost the games, but I need to TH-ink about it." She manages to get out, clamping around your fingers like a vice.
"Oh, well, okay. I won't press the matter then." Mayor Mare says, like she was wounded. She leaves and you take your fingers out of Miss Harshwhinny.
"What the hell was that about?" She asks angrily. You just laugh and shrug.
"Just felt like it would be funny. While we're here, I'm going to go visit my parents." You grab your carrier bag from the table.
"Before you go, a parting gift." Miss Harshwhinny practically leaps onto you and sucks hungrily on your neck, leaving a very noticeable mark.
"Miss Harshwhinny-" You're cut off.
"Oh please, just call me Nancy."
"You're evil."
"I'll be waiting for you on the train." Nancy turns and leaves. This is going to be a fun visit.
~Two hours later~
After a stern lecture about not sleeping with anything with a pulse, the visit with your parents wasn't so bad. You step into the train-car and notice how empty it is. Nancy is nowhere to be seen. Oh well, she probably just stepped out to go run an errand or visit someone. The bathroom door behind you opens, much to your surprise. In walks Nancy Harshwhinny, stark naked.
Time for Round Two.