I felt my day was going to take a turn for the worse when I finished skimming through the article. It didn’t matter that it was the perfect day off. It didn’t even matter that I had a rather substantial increase in clientele requests, or that through Eve’s scheduling skills, I had met them head on with a lot of time to spare.
The article I just read pissed me off enough to put me in a foul mood.
“I have no words,” I declared as I finished skimming through the article in Equine Weekly.
Eve, my handler, lowered the Earth-based newspaper (Something Bulletin, or Bulletin Something, I’m not too sure) she was levitating low enough to spy me through her spectacles. “You have no words? That’ll be the day,” she said. I rolled my eyes.
“Have you seen this?” I asked. Clearing my throat, I began to narrate, “’Humans in Equestria: A Mistake?’” I snorted.
“I think that surmises my feelings in regards to you,” Eve chuckled, neatly folding her newspaper. Her eyes turned serious for a moment as she gave me a nod, gesturing for me to continue. I just stuck my tongue out at her before I carried on.
“As the inter-dimensional race known as humans are becoming a common sight in Equestria, a lot of questions were raised regarding these new species. A few ponies have begun to deride the alliance, calling it a mistake for being formed too soon. The most outspoken of the group was Duchess Emerald Château, who had caused quite a stir among the public when she criticized Princess Celestia’s decision to extend her hoof in welcome to the humans.
“‘While I have utmost respect for our esteemed ruler, one cannot help but question her decision of allying ourselves with such a barbaric race. Humanity’s history seems to have evolved from nothing but increasingly brazen conflicts. They are a race that built weapons of mass destruction as means of a deterrent. They are one race, but of many nations, conflicted in cultures, religion, and even ideas. What have they to offer us? We do not need their technology – their so-called ‘magic’ that has been forged through countless conflicts and wars and that have polluted their world! Ponies have survived thousands of years through unity and harmony. We do not need them here.’”
“Ouch,” Eve replied, wincing slightly.
“Oh it gets worse,” I continued. “‘If some unicorn is able to create a spell or potion that would allow reproduction, then they may have some use. With the Gentlemen for Mares and other companies alike already in place, we could use their comparatively higher number of males to boost our population, as long as the resulting foals are one-hundred percent pure ponies.’” I took a breather and raised my eyebrow. “I don’t know what’s more insulting: that she dropped our company name, or the fact she thinks exploiting us as studs is our only use.”
“Ah, pony cultural revolution. Instead of having the stallions on the fields or beds, it’s now just the beds,” Eve shrugged. “Don’t pay any mind to that, Harry. Duchess Emerald sounds like a real twit.”
“Oh, but the article isn’t over. You’re gonna get a laugh at this,” I advised as I let my eyes roam the piece of writing once again, trying to find the specific sentence. “Where are you... ah, there you are. ‘Not all agreed with Duchess Emerald Château’s sentiments, with some publicly defending Princess Celestia’s decision. One surprising defense came from Prince Blueblood.
“‘Duchess Emerald is an old-fashioned, embittered relic. She would have happily had stallions rounded up and forced to plow her fields in more ways than one. I, for one, am glad of our alliance. The Human World is a rich collection of cultures and ideas, and that is why I believe that Princess Celestia made the right decision.’
“Huh,” I muttered, raising an eyebrow at Eve. “Didn’t you call this guy as a class-act jerk?”
The mare rolled her eyes. “That is because he is a class-act jerk. If you’ve been reading articles regarding his visits to the human world, then you’d know he only likes it there because he discovered alcohol, and loves your ‘films’ and ‘movies’. He couldn’t stop talking about that Iron Human movie. I think he’s in love.”
I laughed. “Of course he would be.”
“Please tell me that there’s more. If he’s the only pony defending ‘humanity’s presence’ in that article, it doesn’t bode well,” Eve said as she levitated a glass of water. She drank from it and let it gently down the table.
“Well, there’s this: Also, Princess Celestia’s personal student, Princess Twilight Sparkle, defended her teacher’s decision in regards to humanity.
“‘Well, while I think the Duchess has a point in regards to some of humanity’s history, one should also should take into account these facts: humanity’s world is not like ours. They do not have the ability to manipulate weather, magically find resources, or even grow food as fast as we do. They have lived thousands of years through toil and hard work, in a world not unlike the Everfree Forest, yet they carved a path of civilization, of progress. Their technology, their ‘magic’, is also evolving to the point that the polluting by-products are slowly being eliminated. I also have to point out that for every tale of human atrocity the Duchess can bring forth, I have ten stories that show how they shine.’
“Well, I think I may have fallen in love,” I muttered as I folded my magazine and placed it down beside me.
“With whom, the Prince or the Student?” Eve asked. “The Prince, I’m pretty sure, is high-maintenance and Miss Sparkle, from what I heard, is too nerdy for you. I don’t quite think they are your type.”
“What are you, my mom?” I chuckled as I poked the air with my fork, pointing it at her.
“I am paying for the meal, aren’t I?”
“Touché,” I replied as I lowered my utensil, waiting for the waiter to arrive with our order.
Eve and I were currently at one of the few human-run restaurants that specialized in making vegetarian meals. I had heard they were deft experts in using tofu as meat substitute, and that the way they cooked it was amazing. I couldn’t wait.
Unfortunately, waiting was the game I had to play. So when I saw Eve unfolding the newspaper and reading it once more, curiosity got the better of me. I rarely received any type of Earth-made newspaper, and with my job, it was far more important for me to know more about Equestria’s social scenes.
One of my friends, Sal, based his whole image on being up to date on Equestrian life and politics. He was now the only Gentleman that had a High Duchess—what was her name, again? Gilded Spiral?—as a customer. Lucky bastard. So, following his example, a whole lot of Gentlemen began reading and made sure we were up to date on the who’s who of Equestria—after all, a mare won’t call a Gentleman who can’t even tell the difference between a Wonderbolt and the Wondercolt.
So when I saw the headline ‘Human-Gryphon Trade Talks Begin’, I realized how far behind I was on Earth’s current events. I asked, “Anything interesting back at home?”
“Well, there are the Human-Gryphon trading proposals,” Eve replied without moving, her face hidden behind the newspaper. “From what I gathered, the Gryphons proposed trading precious metals abundant in their mountains for herds of cows and sheep.” She lowered the paper, letting her eyes peek out once more. “You know, I always find it weird your cows don’t talk at all.”
“Really? I found it weird that cows here talk at all,” I replied truthfully. “How do you milk them without it being awkward?”
“Practice,” Eve replied easily. I snorted at the implication, making her roll her eyes. “Here’s something you’ll find interesting, though.”
“What is it?”
Eve cleared her throat. “‘Senator Carl Rowan believes the Equestrian Ponies are demons sent to tempt mankind away from God’s light.’”
“Oh no, God, please don’t,” I shuddered. “Something else, please.”
“I probably should take that as a compliment,” Eve declared, as if ignoring my little outburst. She asked, in her throaty and sensual Audio Erotica voice, “Tell me, Harry, am I tempting you away from God’s light? Does my—” she scanned through the newspaper “—slovenly disregard to modesty, my natural nakedness, turn you to a—” she scanned again “—a sinner?”
Oh, I was ready for that. “I sell my body for money. I think I am way beyond saving at this point,” I replied, deadpan.
She pouted. In her normal voice, she mumbled, “You’re no fun. And oh, this is interesting.”
“What?”
“Did you know Princess Luna is actually studying ‘English’ back on Earth?”
Wait, what?
My expression must have shown pretty clearly because Eve just nodded. “Yeah. Apparently, she’s studying in something called a ‘university’ to improve her ‘English’. She’s quite a celebrity on Earth.”
Wow, I must have really been behind if I haven’t even heard about this. I imagined one of the immortal Princesses of Equestria studying back on an Earth university, along with her archaic Equestrian-slash-English. I could easily see the Shakespeare crowd worshipping her.
Then I imagined Princess Luna interacting with various social groups. An image of her in a cheerleader outfit (good lord where did that come from?) appeared in my head as she waved pom-poms around with her hooves, screaming cheers loud enough to overwhelm the opposition. Before I could even continue to contemplate how many more clichéd images of her I could think of (I stopped at seeing her playing with a video game controller), a unicorn server arrived with a floating tray in tow.
“Faux Tonkatsu Curry Rice,” the server said, floating a large covered bowl in front of me. Placed on the table, he telekinetically took hold of the cover, pulled it off, and my mouth watered at the scent of the piquant blend of curry and spices as it wafted past my nose.
“Here’s the shredded cabbage,” the server added as he placed the bowl of vegetables beside my curry bowl. “And our house-blend iced tea,” he finished as he levitated two glasses and set them down on our table. They were filled to the brim with dark golden brown liquid, complete with lemon slice sitting on the edge of the glass. I gave him a nod, and he in turn looked at Eve. “Have you decided on what you’ll have today, ma’am?”
“No, but thank you.”
I raised an eyebrow. Ever since I got back on my feet, Eve hasn’t exactly been the type to treat me out to lunches, especially expensive ones at that. And if she did, she’d have ordered something for herself.
Suspicious.
“What is going on, Eve?” I asked, putting roasted sesame dressing on the cabbage.
She gave me a smile. Oh, hell. I’m not going to like this, am I?
“There’s a job for you tomorrow,” Eve declared. She paused.
Oh-kay. “Go on,” I replied slowly.
“New client, hiring you out for two days,” Eve continued.
Wow, two days? “This new client must be rich.”
“She’s a school teacher in Ponyville,” the unicorn advised. “Platinum either knows this teacher, or knows of her. She gave her quite a hefty discount, and is willing to pay the rest of the fee.”
Ponyville... that was the town below Canterlot, almost the very base of the mountain, wasn’t it? Not a lot of Gentlemen hired in that location, as most ponies there lived simpler lives, though rumor has it it was more because the Elements of Harmony (who were more or less national heroes) resided there.
And the boss shelling out money for the customer? First time I’ve even heard of it.
“Platinum,” she continued, putting emphasis on the name, “out of the goodness of her heart, has felt that you are the best Gentleman to handle this.”
“Well, I won’t let her down then,” I said.
“By the way, the customer is in heat.”
Ah... wait, what?
“I think she is also a Skipper.”
Holy crap! I think my eyes bulged out of my skull on that declaration.
“No!” I immediately exclaimed. “Forget it! I don’t do customers in heat, Eve, you know that!”
“You were the only one available,” my handler advised.
“What, isn’t Thomas more willing to work with customers in heat?”
“Scheduling conflict.”
Oh come on, you’re kidding me! “How about Richard? He should be free!” I said desperately.
“Broken hip,” Eve shrugged.
What? She was screwing around with me, wasn’t she? “How the hell did that happen?”
“Well, funny story. It involved Fleetfoot and what he called the ‘Pegasus Mile High Club’.”
Oh hell, Richard, you stupid moron. I sighed, and thought of other Gentlemen who should be available for this, but no one came to mind. Maybe I should take that as a sign to have a more involved social life.
“Come on, Harry. Eat your food. Take your time to savor it, and calm down,” Eve declared slowly, urging me to eat with her hoof. “You’ll feel better.”
I sighed again, and used my fork to take a small stab at the faux tonkatsu slices, grabbing a morsel and dipping it in the curry sauce. I scooped some rice with it before I gingerly put it in my mouth.
Oh, God. This was amazing. The flavor of pork washed over my mouth with such tantalizing tingle that it actually really felt like I was eating meat. How were they able to make the usually silky tofu into veritable delectable sequences of textures and taste? I could squeal like a girl, and I would not care.
Eve smiled at my silence. “Now, when the time comes, remember Harry... Eve”—she pointed at herself with her hoof, and then pointed it to the dish—“food. Platinum... customer in heat.”
I raised an eyebrow. “You are one magnificent bastard.”
She just smiled. “Thank you.”
I took another bite.
A customer in heat, eh? A Skipper at that? Oh God, this was going to be ugly.
Anyone who knows horses knows about their estrus cycles, right? Well, it’s almost the same with Equestrian Ponies. Every month, there’s a week when a mare becomes fertile, and their body becomes a mix of hormones and pheromones that give them the ‘come hither’ aura for stallions.
I don’t think it affects humans that much. All I ever noticed is that they smell a bit muskier, but apparently it turns the heads of stallions (and even some mares) around.
And for some reason, their biological evolution made the urge to ‘go forth and multiply’ almost impossible to ignore. To ‘cool’ them off, the body needs to be fooled that they received a healthy dose of ejaculation (or at least, the near equivalent). Making a mare in heat orgasm would only give them pause. Worse yet, if they ignored the urge long enough, it’d addle them into thinking of nothing but sex.
We called mares who did that ‘Skippers’. Most of them were a bit like addicts, as they usually only would put themselves at this phase because, don’t quote me on this, the rutting becomes absolutely fantastic for them. And the more ‘offerings’ they would received, the more satisfying the feeling.
Before the humans were discovered, mares who didn’t want to get foals would use something akin to a dildo pump. It’s a phallic tool made of materials that supposedly felt like a real stallion’s, and would pump out a mixture with the consistency of male discharge. It’s also an essential tool for mare to mare relationships.
Don’t ask me what it’s called, though. Eve called hers Mr. Happy, and I’ve never bothered looking up its proper name.
When Lyra Heartstrings—the first pony to become famous by dating a human—gave her comments of her satisfaction being given human TLC, the boss created the Gentlemen for Mares. However, the company never really became influential until a mare, in heat, hired a Gentleman and realized that ‘it was the best rutting’ she ever experienced.
And as an added bonus, she wasn’t pregnant.
The word spread. The customers came in droves. And the boss, ever the opportunist, raised prices for customers in heat, and has reaped the rewards the ever since, with her best business coming from Skippers who would always hire out two or three Gentlemen simultaneously for the last days of their heat phase.
It was utterly ridiculous.
While I understand a whole lot of Gentlemen like customers in heat (they get a higher commission, and all they have to do is just... rut them), I’m not like that. I want to put a little romance for all my customers, whether it’s a nice date or maybe a slow intimate exploration of their bodies, always aiming to make it less of a business transaction and more of a personal touch.
I sighed. I took another bite. I’m not a big fan of customers in heat. I distinctly remember the first in-heat mare I had encountered. It left me with such a bad taste in my mouth that I never left my card and actively made it a point to avoid customers in heat.
Now, this would be my second encounter.
“Fine,” I finally declared. “What time am I meeting with the customer?”
“Tomorrow, late afternoon. Platinum said that classes end at around five,” Eve replied. “And Harry?”
I looked at her.
“Remember, me? Good and expensive food. Platinum? Skipper Customer.”
I rolled my eyes. “Yes, I’ll remember when it’s time to overthrow the pink-coated tyrant,” I said, taking another bite.
I arrived at the outskirts of Ponyville the next day, nearing five in the afternoon. Eve wished me luck as I clambered down the chariot, and before she signaled the pegasi team to take off, she levitated a small pouch with a shoulder strap to me.
I opened it up, revealing familiar vials of semi-clear golden liquid. I looked at Eve. “I don’t need boosters. Never did.”
“You never had a skipper earth pony either, Harry. Take it, just in case,” she replied, and the door of the chariot closed before it took off, leaving me in the dirt road looking at the entrance of the town.
Ponyville, from what I saw of it from the sky, had a central hub surrounding a town hall with a red roof. The town itself was a maze of houses and trees, of which the most abundant (judging by the sweet scent) were apples. It also had a river going around the hub and was surrounded by the Everfree Forest.
I entered the town, crossed a bridge over the river, and arrived at the town center. I could see the bustle and hustle of everyday life, its ponies of multiple hues walking and interacting; some were selling wares, while others were just greeting each other.
Surprisingly, I saw a few humans too. A whole lot were all dressed in smart-casual clothes—loose-white buttoned shirts, slacks and shoes. Some wore corporate attire, complete with dark jackets, ties and (some of them) vests. Most, though, wore casual—tees , denims (pants or shorts) and rubber shoes.
At least I’m not under-dressed, I thought as I looked down at my clothes: dark brown cardigan sweater, white shirt, grey slacks and brown loafers. Oh yes, no black tops this time.
Some of them formed groups of their own, but for the most part, they mingled with the rest of the Equestrian citizens as naturally as they would with other humans. There was a woman laughing along with five other mares. Another had a group of male humans and ponies doing hoof-and-fist bumps because one man in their group gave a passing mare a wolf-whistle, and amazingly, got a return wink. I couldn’t help but smile.
Oh, what I would give to show this picture to that clueless Senator and twat Duchess.
Spotting a stall filled with red, tasty-looking apples, I approached the mare behind the counter. She had a dark yellow coat, blonde mane and tail. She also wore a cowboy hat. Huh. And it accented her perfectly too. Did she have... yes, she had freckles too. Three white ones on each side of her face, just below the eyeline.
“Well, howdy, stranger,” she greeted me with a Southern accent. “May Ah interest you into getting some of the best darned tasting apples of all of Equestria?”
I smiled. “Well, why not? How many bits?”
I thought I would have to do some haggling, as most small towns loved to sell their products at a higher price in case a tourist from the big city came around. I was surprised, though, when the mare just gave me a somewhat low price on her apples.
I felt a little apprehensive. Would the best apples in the world be bought at such cost? She may have seen my hesitant look, because she suddenly offered one apple to me.
“This one’s for free. If you doubt mah words, you can always taste it yourself. If you ain’t satisfied, I won’t hold it against you none.”
I reluctantly took the offered apple, stared at it for a bit. I looked at the mare, and she just gave me an assuring grin and nodded. Shrugging, I took a bite.
The fact that it gave a loud crunchy sound as I bit down was already an indicator that she was not pulling my leg. I tasted the perfect balance of sweet and sour with no starchiness to it. I ate lot of apples in Equestria, and there was only one apple that tasted as good as this one, and that was at Trottingham, which I bought at almost double the price this mare offered.
“Give me six,” I muttered while munching.
“You got, mister. Six apples, coming up,” the blonde mare happily said as she grabbed a paper bag and deftly put in six apples. I paid her immediately.
“Well, thank ya kindly, mister. Though Ah must ask, are you new in town? Don’t recall seeing your face ‘round these parts.”
“Just arrived,” I replied, finishing off the free apple she had given me. “I’m actually looking for a—” I fumbled through my pocket with my free hand, and grabbed a folded paper out and read the name written “—Miss Cheerilee?”
“Miss Cheerilee? Why, she’s mah little sister’s teacher. Which reminds me,” and she stepped out of her booth. I spotted her Cutie Mark (three red apples) as she walked by, though I was hoping she was wearing cowboy boots. No luck. She looked towards a big red stallion nearby, and shouted, “Big Macintosh, Ah’m gonna pick up Apple Bloom, so mind the stall!”
“Eeyup,” was all the red stallion said before moving behind the counter. Once in place, a few mares began approaching. Huh.
“As it happens, Ah’m on my way there,” the mare advised, encouraging me to follow. “Name’s Applejack.”
“Wingman,” I replied, and we both shook hand and hoof.
We both walked side-by-side towards south-east of Ponyville. Applejack kept pointing out stores she thought I’d like to visit and was generally very pleasant to talk to. She seemed quite well-known around these parts, too, judging by how many ponies and even some humans greeted her.
“And that there is Sugah Cube Corner,” Applejack said, pointing out a building that literally looked like a cupcake. Architecture here was very odd. “Luckily, Pinkie’s outta town, so we can avoid her fer now.”
Pinkie? I mentally shrugged as we trudged on, passing by another building, this time designed as half a tent with a carousel on top.
“That’s mah friend Rarity’s shop over there. The Carousel Boutique. Business has been booming ever since yer kind started living here.”
I could have taken offense on the words she had used, but I got a feeling it was more of a slip of the tongue with her. “Why’s that? Because humans always wear clothing?”
“Eeyup, that’s right. Speaking of which... Hey, Rarity!”
I watched Applejack waved towards an approaching unicorn with one of the whitest coats I have ever seen; it made her Cutie Mark (three blue diamonds) stand out even from afar. Her purple mane and tail bounced with flourished as she trotted towards us, and as she approached, I noticed her lashes flowing daintily as she blinked.
“Good afternoon, Applejack,” Rarity greeted. “Oh, it’s always good to see you darling. And who’s that handsome young man with you?”
“This here’s Wingman,” Applejack replied, introducing me. “Wingman, mah friend, Rarity.”
She gracefully offered her hoof, and I accepted it with poise, bowing down slightly to bring my lips to kiss it gently.
“Charmed, I’m sure,” I said, looking up to her and giving a smile.
“Oh, verily,” she giggled. “I’m actually surprised to see a Gentleman here.” My surprise must have been evident because she tapped my leg gently with hers. “Oh, please. A pony name for a well-dressed man? Who’s the lucky mare?”
“Uh... gentleman?” Applejack muttered.
I paused for a moment. Telling Miss Applejack was fine, but this unicorn, Miss Rarity, was pretty well-informed regarding how the Gentlemen worked. I wondered if it was okay to drop Cheerilee’s name. I might have hated the assignment, but there was no way I was going to feed fuel to any kind of scandal the school teacher would face if the unicorn would chose to.
However, looking at her, I doubted she’d actually cause any. Maybe it was the honest curiosity she was displaying, or maybe the fact that she said ‘lucky mare’, but I felt I could trust her with the information.
“I’m actually here for a Miss Cheerilee,” I replied to Rarity.
“Oh, dear. Miss Cheerilee. Yes, I think I can see it now,” the unicorn nodded. “But I never figured she would be the type to spend bits to have a Gentleman take care of her. She is usually so independent regarding her needs.”
“Now, wait a minute sugahcube. Whatcha mean Wingman’s gonna take care of Miss Cheerilee? Take care of what, exactly?” Applejack interjected.
“Darling, hasn’t Apple Bloom told you how strange Cheerilee’s been acting for the week?” Rarity asked.
“Well, yeah, but that’s just her heat pass...ing,” Applejack blinked, and looked at me for a moment, her eyes widening before narrowing into slits. “Wait a tootin’ minute! What ya’ll trying to say is that this... Gentleman... ain’t nothing but a fancy shmancy talk for a comfort horse!?”
“Well, you don’t have to put it that rudely,” Rarity replied with a slight huff. “Honestly, Applejack, you’d think that with how B—” and she was cut off immediately when the yellow earth pony bumped strongly into her, almost causing her to lose balance.
“Yer mah friend, Rarity, but if yah talk one more word ‘bout that, Ah’ll buck you hard to the next town!”
The white unicorn gave the earth pony a glare. Without taking her eyes off Applejack, Rarity said, “Mister Wingman, I would appreciate if you walked ahead. It seems I’m about to have an argument with my friend, and I really would prefer you not witness this.”
I looked at the unicorn and then back at the yellow earth pony. On one hand, I wanted to stay and try to clear this out. They were friends, and I didn’t like it when friends got into disagreements, especially if I was the one at fault. On the other, I just met these mares. I was essentially a stranger to them, and it would be quite rude and stupid of me to get involved in a row between two friends.
“Um... I’m sorry,” I muttered before I continued walking.
I could hear a few shouts behind me as I trudged on, wincing as I heard really angry words fly through the air. I just forced myself to go forward, thanking my lucky stars that the argument was slowly receding in volume and that I could finally see my destination.
The red building in front of me was built like a schoolhouse, complete with a bell tower, a flagpole (with a small scooter and helmet leaning on it), and a playground to the side. I could see little colts and fillies laughing as they all exited the building, skipping and jumping as their day of school was finally over. They paid me no mind as they passed by.
As I entered the school grounds, I was greeted by three more fillies. One was an earth pony filly with yellow coat, red mane and tail, and quite a distinguishable pink bow, spoke in a Southern accent very reminiscent of Applejack.
“And Ah’m telling ya, Miss Cheerilee’s been acting all weird,” she declared to her two friends, a unicorn with white coat as well as a pink-purple mane and tail, and a pegasus with an orange coat to go along with her dark pink mane and tail.
“Oh, come on Apple Bloom. Miss Cheerilee is probably just tired,” the orange filly replied. “She’ll feel all better tomorrow.”
Oh, you have no idea, kid.
“Scootaloo, she almost couldn’t finish the last problem on the board,” the white unicorn replied. “What if she’s sick?”
“Sweetie Belle is right!” the yellow filly (Apple Bloom?) declared. ”Maybe we should bring her to the hospital!”
“Maybe we could get our cutie marks that way!” the orange filly (Scootaloo?) exclaimed.
Then, all three shouted, “Cutie Mark Crusaders Patient Delivery, Yay!”
I ought to check my blood sugar after this. I’m actually hoping to see if they could actually pull it off, but I couldn’t have them drag my customer around to the doctor, right? So, I walked up to them as normally as I could and gave them a wave as I greeted, “Good afternoon there!”
The three fillies looked up; the orange coated one raised an eyebrow while the rest looked at me with neutral curiosity.
“Hi, I was wondering, is Miss Cheerilee inside?” I asked.
“Um, yes?” the white filly (Sweetie Belle, right? Huh, I think I’m getting a good grasp on their names now) replied, unsure.
“Why?” Scootaloo demanded, moving in front, blocking my entrance to the school. “What do you want with Miss Cheerilee?”
“Nothing you guys should worry about,” I assured as I side-stepped the orange filly, only for her to quickly block my way again.
“Well?” the orange filly asked.
I looked at her, and gave her a small smile. “I’m just here to take care of her.”
“What do you mean?” Sweetie Belle asked.
“You’re not gonna hurt Miss Cheerilee, are yah, mister?” Apple Bloom inquired.
“No, no, of course not.” I paused for a second, trying to think up a good way to explain what I’m about to do that doesn’t involve the birds and the bees. “Miss Cheerilee is a little out of it, and I was called in to take her out and have some fun.”
“What kind of fun?”
Yeah, kid, ugh, damn, why did you ask that? As I stumbled around to find another G-Rated comment, I was saved by a familiar voice shouting sharply behind me. I looked behind me just in time to see Applejack and Rarity approach.
“Apple Bloom!” the yellow earth pony had shouted. She gave me one hard look before her features softened as the yellow filly ran past me.
“Applejack!” the younger earth pony declared as she ran into a welcoming hug.
“Had fun today?” Applejack asked.
“Yup, even if Miss Cheerilee’s acting weird again,” Apple Bloom replied. She motioned her head to my direction, and added, “But that mister says he’s going to help Miss Cheerilee. Ain’t that great?”
Applejack gave me one last look—a neutral one this time—and hugged her sister close, almost carrying her out of there. That left me alone with Scootaloo, Sweetie Belle, and the approaching Rarity.
“I’m sorry about that, darling,” the white unicorn declared as she drew near. “Sometimes, it’s hard to remember that Applejack is a bit of a prude and quite hard-headed when she wants to be.”
“It... it’s not going to be a problem between you two, is it?”
“You’re sweet, but fret none,” Rarity replied easily. “It’ll take more than that argument to actually cause some problems between us.”
“Are you fighting with Applejack?” Sweetie Belle asked.
Rarity looked at the white young unicorn, and shook her head. “Nothing to worry about, Sweetie. Applejack and I are just disagreeing on something. Now, come on. It’s time to go home.”
“Okay,” Sweetie Belle happily declared and trotted beside the older unicorn, who suddenly perked up as if she remembered something.
“Oh, and before I forget, Mister Wingman, would it be presumptuous of me to ask for your card?”
“Uh, company policy doesn’t allow me to give you my card until the first... uh”—I looked at Sweetie Belle and Scootaloo, then tried to find a good substitute for the word—“rendezvous. However, I can give you this.”
I grabbed my pouch with my free hand, and I fumbled a bit on trying to open it when I felt the bag of apples float out of my arm.
“Here, let me take care of this for the moment,” Rarity advised, her horn glowing in light blue light as she levitated my load. With two free hands, I finally extracted a platinum white card with gold ‘Gentlemen for Mares’ engraved into it. I grabbed my felt pen out, and wrote my work name.
“Address is here, so you can write us a letter, or call us if you have the new telephones. Our number is here as well,” I advised, handing a card to her. She gladly accepted it, gently feeling the card with her hooves. “You can ask for me, or take suggestions. We’ll happily mail you a list of Gentlemen at our disposal, and you can find who strikes your fancy. We guarantee satisfaction.”
“You are very kind, darling. Here you go,” she floated the bag of apples near me for easy grabbing, and gave me a wink. “If you are in need of some clothing, may I suggest you visit my boutique? You won’t be disappointed, that’s my guarantee.”
“Will do, Miss Rarity. Pleasure meeting such a lovely lady.”
She giggled daintily. “Oh-ho, quite the charmer, Mister Wingman. Ta-ta, dearie. I hope to see you soon.”
The white unicorns left me alone with the orange pegasus, who was still blocking my way. I looked at her for a moment, and I raised an eyebrow. She raised one back. Not to be outdone, I lifted mines even higher, and she responded the same way. We stared into each other, eye to eye for a good minute before she finally blinked.
I crossed my arms, smirking. Yeah, that’s right, little filly. I win.
She just took her tongue out at me before scampering towards the flagpole and grabbed the helmet that lay on top of the leaning scooter. She motioned her hooves, pointing at her eyes first then at me, before she jumped on top of her scooter and flapped her little wings. Amazingly, she propelled herself with impressive speeds that I felt the slight sucking wake of her passage as she roared past me like a bat out of hell.
Well, at least I avoided more awkward questioning. That just left me with...
Hoo-boy. Is it me, or did the building suddenly transform to a gaping mouth? I sighed, and checked my inventory. Apples? Check. Pouch full of magic Viagra? Check. Balls? Whoops, must have left them near the apple stand...
I almost, almost left. I really, really didn’t like this. I definitely, definitely should have just said no to Eve.
I still entered the building.
I came to the receiving area, and looked around. It was painted in upbeat and bright colors of light green and yellow hues with ponies and horseshoe accents. There were low couches, and on the walls, cork-boards filled with pinned drawings or writings by young fillies, most of them stamped with ribbons of various colors.
Other than that, it was empty. My steps squeaked slightly as I approached the door going into the classroom, half-hoping that it would be empty.
A sound of a hard object thrown behind the door dashed my hopes. Sighing at the inevitable, I gently knocked on the door before I entered.
I smelled it immediately. The slight musk scent clashed horribly with the fresh lemon scent of the whole area. First thing I saw was a rather moist pencil on the ground, and looking up I saw, at the end of the room, an earth pony behind a desk, her face down between her front legs on top of the polished wooden surface, shivering.
“Miss Cheerilee?” I called reluctantly. The pony’s head went up immediately, her eyes unfocused as she looked at me. I slowly approached her, taking careful steps as she slid off her place, slowly approaching me.
She was quite a pretty mare with a unique cherry-colored coat with two-toned pink mane and tail. I noticed her three smiling flower cutie mark readily as she sauntered towards me, her hips really moving in a bit of an exaggerated (but quite seductive) motions.
“My name’s Wingman, and I’ll be your Gentleman for the next two days. I was hoping that—” and I immediately stopped when her snout just went straight for my crotch, her breathing getting rather ragged.
I could hear her coo as she began to sniff, bobbing her head gently. My body reacted immediately, and I felt uncomfortable tightness in my pants. It didn’t help when she was suddenly licking mea over my trousers.
“Oh-kay!” I backed away, only for her to chase forward, her eyes sparkling as she just stared at that area.
“Please,” she said throatily. “Please... please?”
I immediately dropped the pouch and apples on a desk and went towards the door to lock it. After that, I made my way to the windows to make sure I closed all the curtains. Cheerilee followed me all the way, rubbing my legs with her tail. One time, I think she nudged me from behind with her head, as if telling me to hurry up.
I took off my sweater and top, easily slipping out of my loafers and slowly undoing my pants. Too slow for Cheerilee, apparently, as she bit down on one of the leg pants and forcefully tried to remove it. I gently flicked her ear, making her snap her attention at me long enough to remove the pants on my own power.
“Okay, behave or I’m leaving you like this!” I warned as I grabbed a tuft of her mane and pulled it gently, holding her in place. It was really an empty threat. If she wanted to, she could force herself on me and I couldn’t do anything about it. Earth Ponies didn’t have any real vulnerable spots to exploit, like wings of a pegasus or the horns of a unicorn. They were also physically stronger than any of the three types of ponies.
I could only pray that she’d listen.
As I removed my underwear, I could feel her shiver and almost take a step forward. I pulled her mane again and she stilled. Damn it, this was it. No dates, no talks, just straight to tucking.
I really hated this assignment.
I roughly kissed the mare, maybe letting a little anger and irritation take hold as I began to pushed Cheerilee back. Part of me wanted to not care about her. She hired me to scratch an itch, so scratch I would. I let my fingers roam around her neck, then roughly scraped them along her coat as she moaned in either pleasure or pain. I didn’t care. I just sloppily kissed her neck, shoulders, and ended spanking her flank with a little more force than necessary.
She gave out a satisfied neigh and immediately turned, showing me her rump as she elevated her hindquarters. I grabbed a hold of her hips, and without preamble, entered her soft, wet and readily inviting folds.
Oh, God. I forgot how it felt rutting a mare in heat. The closest thing I could describe it as was a marehood that seemed to have a mind of its own, readily accepting my entrance but clamping down hard every time I tried to pull out. It gave the oddly satisfactory feeling of being sucked inside her, and I grunted as I immediately felt the threat of ejaculating a bit too soon.
“Yes, yes, yes!” she moaned, volume of her voice slowly increasing with each thrust. I felt a little fire in me as I realized she was enjoying herself. And as bitter as I was on this assignment, I couldn’t help but feel a bit satisfied.
I screamed and went faster. She was in heat, and the best way to satisfy her was to come. So, I grabbed her mane, pulling it back a bit as I pumped at her even faster. I screamed her name as my rhythm became erratic as I crossed the threshold and came.
Her walls immediately began to move at unbelievable speed, milking me as I spurted as strongly as I could inside her. I felt a mixture of pain and pleasure building as her velvet walls churned around my manhood, as if begging for more, and then slowly, the pleasure faded as the pain began to build.
I immediately tried to pull myself out. She wouldn’t let me. I grunted as the walls still began to agitate around my oversensitive member, and with great force, I was finally able to separate myself from her. I landed clumsily on the hard floor, my breathing somewhat ragged as I saw the Earth Pony slowly lower her rump before she collapsed on her knees and lay down on her side.
I heard her crying.
I heard her whisper.
“Thank you... thank you...” she said softly.
I sighed, placing my hand over my forehead. I sat there for a few seconds before I finally dragged myself to the downed mare. I placed my hand on her side, and rubbed her coat gently. In the softest tone I could produce, I whispered assurances in her ear and gently combed her mane with my free hand.
We stayed like that for a few minutes. It was nice.
It was really nice.
“I am really sorry about that,” Cheerilee declared, her eyes avoiding me as we walked towards her home in Ponyville. “I don’t usually act like that, especially with strangers.”
“Don’t worry too much,” I replied easily, breathing in the crisp cold night air as we walked through the almost empty streets of Ponyville.
It’d been ten minutes since the act, and with her body finally satisfied with my ‘offerings’, Cheerilee’s wits finally returned and she proved to be quite an amicable companion. I felt a bit embarrassed about being angry with her and thinking she would be like my previous in-heat customer, who, after the act, ignored my existence until the next phase came over her.
I was basically her version of Mr. Happy. No surprise I never left her my card, that stupid mare.
Cheerilee, though, was turning out to be quite different. She seemed thoroughly embarrassed by the situation, always avoiding my eyes as she kept apologizing for the trouble. She apparently had wanted to take care of it sooner, but was unfortunately hit by a busy week and a series of bad luck (her Mr. Happy was, uh, worn down, and most of the local stores were out of stock for replacements. She was also skittish of borrowing someone else’s).
I was actually glad that she kept at a generous distance away. I didn’t have the heart to tell her I had thought of her as the usual Skipper, an addict for sex and the ultimate pleasure. My stomach took a deeper dive when she said it was her first time skipping.
Yeah, great move there Harry. Good thing you didn’t open your damn mouth about it too, right?
I was still stewing in my own guilty conscience by the time she led me to a modest house a little west of the school area.
It looked like any house you’d see in Ponyville—a pale-colored rectangular wooden structure with a yellow straw roof and a small chimney on top—and she easily opened her door with a push of her foreleg, making me wonder how safe the town was if these ponies didn’t even bother locking their doors.
“Um, yes, well, uh, welcome!” the school teacher declared as she let me in and good lord, the place was a mess.
No offense to Cheerilee, but how the hell could she be a teacher if she couldn’t even keep her house organized? The place felt like someone had set off a bomb made of parchment and books. Strews of paper was scattered all around the living area, as well as quills (some standing upright, having stabbed the poor couch). Hardbounds were left around haphazardly, some of them open in random pages. Hell, the only thing organized in this dump was a stack of what looked like vinyl records and a phonograph in one corner.
“Sorry about the mess,” she whispered, embarrassed. “I’ve been meaning to clean up, but I was so... busy.”
She quickly trotted around the house, picking up a few random things from the floor, and casually tossing them aside, out of the way.
“Um, are you hungry? I think I have a few sandwiches on the icebox,” she babbled, then immediately dashed towards the kitchen. I raised an eyebrow and followed the earth pony, noticing the lay of her kitchen was the same as mine—an icebox, where she was currently rummaging around, a small dining table, and a small stove.
I smiled slightly as I made my way to the dining table, placing my pouch and bag of apples on top. I sat down at one of the seating pads as I waited for Cheerilee to finally stop rearranging her icebox. She did after a minute. Her head finally peeked out the storage appliance as she placed a hoof on her face. “No, no, no! I thought I had food. I have to get some now—”
“Miss Cheerilee,” I interrupted her. She stopped her mumbling for a minute and looked at me blankly as I tossed an apple to her direction. She caught it easily with her hoof. She shifted the fruit around for a minute before she sighed.
“I’m such a mess,” she declared before taking a seat opposite of me. “I, um, thank you.”
She bit into the apple, letting the sound of perfect crunchiness echo in the small room. Smiling, I got my own apple, and before I joined her in eating, I replied, “It’s quite alright.”
Cheerilee nodded as she took another bite. We settled into a comfortable rhythm of hearing apples crunch delectably with every bite. I was a bit famished, and with only four apples left to divide between us, I was pretty sure I was going to have a pretty large breakfast tomorrow.
Once the earth pony finished hers, I offered her another. She blinked, confusion evident in her eyes, and she hesitantly took the fruit. She shivered when my finger touched her hoof but she quickly hid it by grabbing the apple and beginning to munch on it with deft speed as I finished off mine.
The two apple cores increased to four, and then later, six. My stomach felt filled enough that it won’t complain for a while, and I began to gather the cores and throw them in the garbage bin. For some reason, I could feel the mare’s eyes on me.
“So, um, how does this work?” the earth pony asked. “Do you sleep at a hotel? Is someone picking you up, and you’ll return here tomorrow?”
I turned and faced her. Her front hooves were ineffectively covering her blushing cheeks. “I was hired for two days, so I’ll stay with you for two days.”
“Oh, um,” she paused, eyes swerving around slightly. She began to tap her front hooves together. “Maybe we should, uh, call this off? I mean, thank you for earlier, I really, really, oh Celestia, really needed that, but I’m fine now.” She twitched. “I’m quite alright.”
I didn’t believe her. Not one bit.
“You’re feeling another one coming, aren’t you?” I asked.
Cheerilee just planted her whole face in the table and covered herself with her hooves before she mumbled, “Yes.”
I walked to her place, and let my hand on top of her mane. She shivered at the touch. I leaned down and whispered to her ear, “Let me take care of it.”
Her face rose, eyes sharp as she stared at me. There was still some hesitation as she shook her head. “You... you don’t have to. You’ve done quite enough... no, wait. Wait. Oh n—ugh, yes, you have done eno—” she groaned as I gently bit her ear.
“Let me ravage you, Cheerilee,” I whispered.
“Oh Celestia, yes,” she whimpered.
Her room was as much of a mess as the living room, which suited me fine. I told Cheerilee that the faster she was in clearing the way, the more she could watch me undress. She quickly removed her horseshoes, and trotted around the room, tossing any offending articles aside as I began to strip off my clothing slowly.
That did the trick. She finished cleaning up faster than I did undressing. Motivation was such a powerful thing. And as her eyes drank me hungrily while I slowly removed my shirt, I approached her and led her to her bed. Before gave her a light kiss on her lips. She tried to follow up with a deeper one, but I moved back.
She whined slightly, but stayed put as I began to remove my loafers and socks. Once again, I approached her and slowly grabbed her hips, letting my tongue gently glide over her mare lips, causing her to shiver as she raised her rump up. I just tantalizingly left ghostly kisses on her marehood and disengaged once more, earning a bigger groan from the earth pony.
“No more teasing,” Cheerilee growled.
“You had your fun, earlier. Let me have mine,” I replied, leaving my underwear on as I immediately placed myself on top of her, my lips and hands attacking her everywhere, from her open ready mouth and her messy mane to her flanks and quivering folds. I pinned her down and rubbed myself to her body, enjoying the slight prickly feeling of her coat on my naked skin and enjoying the ever-increasing potency of her musk.
She readily accepted my kisses, and groaned as I began to finger her marehood with my free hand. She was already sopping wet and her hind legs were already spreading as much as they could, waiting for ultimate deliverance. When it didn’t come, her frustrations began to build as she tried to to roll over and pin me down.
It took her a few tries before she finally succeeded on clambering on top of me. I groaned as I found myself sandwiched between her and her bed as she took the offense, kissing me intently while her front hooves touched and sucked on my chest and nipples. When she broke the kiss, she slowly lowered herself to my stomach, gradually, delectably descending lower and lower.
She stared at her target, her nuzzle gently moving through the cotton texture of my boxers. I felt myself getting more excited as her hot breath seemed to have bypassed the clothing and shot a few sparks of electricity to my spine. Using her hooves and teeth, she gently pulled my underwear down, freeing my hardening member from its confines as it stood proudly up in the air.
She looked at me for a moment, and I just nodded, spreading my legs slightly to give a less intrusive view. She gave me a happy nod and began to nuzzle it, contentedly smelling the length, up and down as I groaned, feeling her snorting exhalations and brush of short hair.
Hurriedly, she began to lick my manhood. I almost completely closed my legs in reflex, but I kept them open for her as she licked generously everywhere. One time she licked a bit too low, trapping the air in my throat for a few seconds before her tongue clambered up and wrapped around my tip. She then took me in her mouth.
I groaned slightly as I felt a ghostly brush of her teeth on my sensitive skin as she began to bob up and down my manhood gradually, savoring it as if it was fine wine, slowly, meticulously, and definitely so damn arousing I almost protested when she stopped.
“Inside me... please?” she begged.
“As you wish,” I replied.
I clambered up from the bed, and positioned her near the edge of the bed, hind legs dangling out. I told her to lie on her stomach. I stood outside the bed, grabbed ahold of her hips, and made sure she was safely supported from the front before I plowed into her marehood once more.
“Oh Celestia!” she screamed as I went to a rhythm, fully exploiting my grip on her hips to fully go in and out of her as she writhed, her front hooves creating creases on her bed. My pumping made the bed creak slightly as I kept moving my arms and hips in antagonistic tandem before I shifted her slightly to the side, lifting her right rear leg and having it rest parallel to my chest.
I kissed the length of her leg as I went faster. Her vaginal walls were now gripping me even tighter as I felt myself so close to release. I looked at her, the beautiful Cheerilee, as she bit down on her blanket to muffle her screams before I totally lost it and came inside her for the second time of the day.
I collapsed on the bed beside her, huffing as I watched her shiver with utter joy as she twitched now and then, smile wide on her lips. After a moment, her eyes sleepily opened and she sighed contentedly.
“That... was... amazing,” she whispered.
I kissed her gently. “Wait until you see what I’ve got planned for you tomorrow.”