The Life and Times of a Winning Pony

by Chengar Qordath


The Pony With Irresistable Charm

“C’mon Blossom, we’ve got celebrating to do!”

It’s not every day that a pony makes team leader on the weather squad. Technically Rainbow Dash had promised the two of us promotions last week, but it takes time to make these things official and I’d held off on the celebrating until the paperwork got through. Everypony knows that firing up the festivities before it’s all been made official is just asking for trouble. Then again, after what we’d done for Rainbow Dash and Pinkie Pie, the odds were high the paperwork was as good as done anyways.

Playing matchmaker for the boss and Ponyville’s top party pony had really worked out for us. Keeping the weather working on the rest of Hearts and Hooves Day had probably counted for a lot, but it’s a safe bet that helping the boss finally get some action was the main reason Blossom and I would be earning bigger paychecks from now on.

“Celebrating?” Blossomforth sounded a touch uncertain about the plans I was already hatching. “What kind of celebrating?”

“Oh you know.” I gave a casual wave of my hoof. “Go out for a night on the town, have some fun, do something a little crazy, the usual.”

Blossom narrowed her eyes in suspicion. “You’re not trying to seduce me, are you?”

I rolled my eyes at that. “Sheesh Blossom, keep asking me that and I might start thinking you actually want me to.” Predictably, that made a blush appear on her freckled face. She’s always been a bit of a prude when it comes to sex. I decided to have a bit of fun with her. “Is that what it is Blossom? You want a bit of the old Cloud Kicker charm? ‘Cause if that’s all it is, you just had to ask; moving things up to friends with benefits sounds great to me.”

Needless to say, Blossomforth was now blushing like crazy and nervously pawing at the ground. Having a white coat didn’t do her any favors there. “No! I wasn’t – I don’t want to –”

I put a hoof to her mouth before she could dig herself too deep. “Relax Blossom, I’m just messing with you.” I really needed to help her loosen up a bit sometime. I’d kind of hoped that when she got a date for Hearts and Hooves Day she might get a bit less tense about anything related to love, romance, and banging, but the date ended pretty disastrously. I still hadn’t gotten the details from Blossom; she hadn’t even told me what guy she’d gone out with.

“Anyway, Pinkie Pie’s planning to throw us a surprise party,” I informed her. “So I don’t think you need to worry about things getting too crazy for you to handle.”

“Not much of a surprise party if you already know about it,” Blossom pointed out.

“Well technically speaking I don’t know. I’m just ninety-nine percent sure it’s going to happen. Ever since she hooked up with the boss, Pinkie Pie has been throwing parties at the drop of a hat.”

“Guess you’re right about that,” Blossom agreed. “A Pinkie Party should be fun; we had a pretty good time at the ‘Applejack’s hat fell off her head but didn’t get damaged or end up all muddy and icky, so let’s have a party’ party.”

“You know Pinkie’s heard about us getting promoted now that she and the boss are banging on a regular basis.” Even if she wasn’t in the mood to party at the smallest excuse, we’d earned points with Pinkie for helping her out on H&H Day. Pinkie was the kind of pony who gave a lot of credit for good intentions, even if the execution was a bit sloppy. Besides, sloppy or not, it had worked. Pinkie and Dash were a thing now. If a plan works, it’s a good plan.

“So where do you think Pinkie’s planning to hit us with the surprise party?” Blossom asked.

“Well since it’s supposed to be a surprise, it’s probably going to be at one of our homes instead of Sugarcube Corner.” I reasoned. “Probably my place; it’s a lot easier for an Earth Pony to set up a surprise party on the ground than in a cloud-house.”

“I don’t know how you can put up with living on the ground.” Blossomforth gave a slight frown at me. “Ground-houses are so much trouble compared to clouds. You have to get wood and stone, hire ponies to build it, and it’s all so…fixed.”

“It would be nice to be able to move my place whenever I get bored of the view out the window,” I admitted. “Kind of makes it hard to bring anypony other than pegasi home though. Not everypony wants to go back to their place, and trust me – doing it out in a grassy field isn’t nearly as fun and romantic as you’d think.”

Blossom sighed and gave another annoyed roll of her eyes at that. “Of course. It would be all about that.” The two of us trotted along for a bit, but I couldn’t help noticing the way my friend was frowning at me. “I don’t get you, Cloud Kicker. Half the time you talk as if the only thing you care about is, well…”

“Banging?” I suggested. “Mating? Fornicating? Intercourse? Coitus? Coupling? Copulating? Having congress? Making love? Screwing around? Gaining carnal knowledge of other ponies? Sex? F–”

“You can stop now!” Poor Blossom looked like she was about two second away from dying of embarrassment.

“Sheesh, they’re just words Blossom.” I don’t know how she could be my friend for so long and still be so uptight. “It’s nothing to be ashamed of. It’s completely natural, and trust me, it’s one of the most fun things two ponies can do to waste a bit of time. Hay, I’ll bet you that there’s at least one couple that’s banging right now somewhere in Ponyville.”

“That’s what confuses me about you,” Blossom grumbled. “You spend so much time going on about…” The prudish pegasus took a moment to gather her courage and very quietly whispered, “Mating.”

“Nice work Blossom!” I gave her a pat on the head that was only mildly condescending. She brushed the hoof away and shot me an annoyed look.

“Anyway, you spend so much time talking about that and you don’t mind making fun of the fact that I’m not quite comfortable talking about it, but then you keep insisting that there’s more to you than just your obsession with mating.”

Wow. She’d gotten to the M-word without even a stumble that time. At this rate, I might actually be able to get her to the point of being able to discuss the topic like a pair of grown mares. Possibly by the time we’ve both turned old and grey. Still, it’s a relief to know we won’t be dancing around the subject like a pair of flight camp fillies forever.

I have to admit, it felt nice to actually have anything even resembling a proper conversation on the subject with Blossom. She was fun to hang out with, but my personal life had kind of been the hydra in the room that neither of us was willing to talk about. It was kind of ironic, considering one of the things that made me decide to become friends with her in the first place was the fact that our relationship was the most platonic one I’d ever had in my life. We probably wouldn’t be able to have such a good friendship if I hadn’t decided a while ago that she was absolutely off-limits for banging. Teasing was still fine, though.

“There’s a real simple answer to the whole ‘do I only care about banging’ thing, Blossom,” I told my friend. “Think about it this way: Derpy likes muffins, right?”

“I guess?” Blossom answered uncertainly. “I don’t really know her all that well.”

“Well she does.” I’d forgotten that Blossom wasn’t a Cloudsdaler, which meant she had missed out on the dubious honor of going to summer flight camp and having known most of the pegasi on the weather team since we were all foals. Then again, even if she’d been a Cloudsdaler, she would’ve been two years behind me – and I was a year behind Derpy, so they wouldn’t have been all that acquainted anyway. Even if I didn’t have very fond memories of my time there, summer flight camp had been one of those formative experiences. After all, Cloudsdale was the weather capital of Equestria, so a lot of the pegasi that went into weather work were Cloudsdale natives. When most of the ponies you go to school with wind up working in the same industry as you, those old schoolyard rivalries and friendships can be all kinds of important. Hay, flight camp history had nearly killed my chances of getting a job in Ponyville at all.

“Anyway.” I got back on topic. “Derpy likes muffins. A lot. But as much as she likes muffins, there’s a lot more to her than the fact that she likes muffins. She’s got a kid, she’s one of the most well-intentioned ponies I’ve ever met, and she’s a huge klutz.”

“I think I see what you’re trying to say,” Blossomforth said contemplatively.

“Yeah. I like banging, but it’s not all there is to me.” I flashed a grin at her. “I’ve got depth. A hint of mystery, if you will. It’s part of that irresistible charm that makes everypony like me.”

Blossom rolled her eyes. “So even in the parts of your life that have nothing to do with mating, in the end it still somehow ties back into your obsession with mating.”

“What can I say, I’m consistent.” I do have a reputation to maintain, after all. That’s the one downside of living in a small town like Ponyville. Up in Cloudsdale or over in Canterlot, a pony could generally fade into the background, just one of the thousands of ponies going about their ordinary daily lives. In Ponyville on the other hoof, odds were you’d be running into that cute stallion or mare from a couple nights back all the time. Then again, having a rep meant not having to deal with ponies that had the wrong idea about what I wanted, so it’s not as if being a bit of a known quantity was a bad thing.

Any further discussion on my personality and sex life ended because the two of us were at the door to my home. I smirked at Blossom. “Act surprised when everyone jumps out at us. It’s supposed to be a surprise party, after all.” I nudged open the door and turned on the lights.

And found my home exactly the way I’d left it – completely empty, save the dirty dishes in the sink from this morning’s breakfast.

Huh. Well that wasn’t what I’d been expecting.

“Oh wow.” Blossom broke out the sarcasm. “This is such a surprise. Thank you so much for coming, everypony.”

I couldn’t believe I’d been wrong. “I was sure Pinkie was gonna…”

“Ninety-nine percent sure, as I recall,” Blossom snarked at me.

I gave a philosophical shrug. “Well, that’s what I get for thinking that I could actually predict what Pinkie Pie would do.” I have to admit, I kind of envied Rainbow Dash; something told me Pinkie was likely to be one interesting pony to get in the sack with. Then again, a pony as athletic as Rainbow Dash probably wouldn’t be any slouch in that department either. The two of them probably got all kinds of wild when they banged.

Note to self: If I ever end up in a situation where Rainbow Dash is no longer my boss/co-worker, make careful inquiries into the possibility of a threesome.

While my mind was on that particular subject… “Anyway Blossom, since the party’s a bust, I’m gonna hit the town. Want to come with? I’ll even wingmare for you, if you want.” My motives weren’t entirely altruistic. Given her general lack of confidence when it came to all things romance-related, playing wingmare for my poor naive and inexperienced friend was a very safe move; most of the ponies that made a good match for me would be terrible for her anyway.

“Yeah, no thanks Cloud Kicker.” Blossom took to her wings. “I’ll see you tomorrow, OK?”

“Okay then. See you tomorrow.” Darn, hanging out with her would’ve been fun.

Oh well, her loss. Time to hit the town.



I woke up the next morning feeling sticky and satisfied. That feeling lasted for all of five seconds before I figured out what had woken me up: The sound of somepony knocking on my door. “Alright, just a minute,” I grumbled sleepily. My partner from last night had already cleared out, which saved me the trouble of having to clear him out myself. It’s always nice when you get a pony who knows a one-night-stand for what it is. Trust me, nothing is more awkward and uncomfortable than having a pony decide they’ve fallen in love with you after a brief and completely meaningless little fling. There’s no graceful way to tell somepony that what they saw as a deep and meaningful romantic encounter was just a little bit of fun for you.

You’d be surprised how many ponies will mistake ‘Hey. You’re cute. Want to go back to my place? We’ll bang, OK?’ for ‘I am interested in a serious, committed, long-term relationship.’

I opened up my door and found myself face-to-face with my boss. Always a great position to be in when you’ve just woken up and haven’t even washed your face or brushed your mane yet.

“Hey – uh – Cloud Kicker?” Rainbow Dash looked a bit too confused to start laughing. “You’ve kinda got some jelly in your … everywhere.”

“Yeah. I noticed.” I cast a glance around my place and spotted several patches of jelly splattered over the wall, floor, and ceiling – not to mention all the jelly left on me. “Last night got weird.”

“Okay…” Rainbow Dash cleared her throat, and by unspoken mutual agreement we just set that matter aside completely. Discussing my sex life with my boss would get into awkward territory fast. “Anyway, I just wanted to let you know that I want to talk to you and Blossomforth a bit about some of the stuff that comes with your new jobs. You know, what kinda stuff you need to do, how to handle things when I’m not around, who to talk to in Cloudsdale if we need anything from them – that sort of thing.”

Ah yes, all the boring necessities of work. “Sounds like a plan.” I let out a massive yawn, and idly scratched one of the dried-out patches of jelly on my back. “Uh, were we gonna talk about all that right now or…”

“Nah, meet me in Sugarcube Corner in half an hour.” Great, that should give me plenty of time for a quick bath and a bit of waking up. Showing up to work half-awake and covered in dried jelly wasn’t the best way to demonstrate that Rainbow Dash made the right choice when she decided to toss some more responsibility into my hooves.

At least I wouldn’t need to worry about breakfast if we were meeting up at Sugarcube. A second later, the other facts about just where we were going to be having this meeting clicked in my brain. It didn’t take a genius to figure out that Rainbow’s reasons for having our morning meeting at Sugarcube Corner had very little to do with the easy accessibility of breakfast food. “Sure you won’t be too distracted if we’re meeting at your fillyfriend’s place, boss?”

“Don’t worry about it, we’ll be fine.” Rainbow tried to play it cool, but she wasn’t doing a very good job. The big goofy grin that popped up on face as soon as Pinkie Pie’s name came up kind of gave her away. The two of them were still in that early phase where they were ridiculously happy about being in a relationship. It was cute. It also meant that despite her assurances to the contrary, Rainbow Dash would almost certainly be distracted whenever Pinkie Pie was around. I wasn’t going to complain though; those two ponies deserved every bit of happiness they could grab.

“Alright, see you then.” As Rainbow idly turned around and prepared to take off, I got to work on figuring out the best way to clean up dried-out jelly.

Half an hour later, I was walking over to Sugarcube Corner. I’d successfully de-jellyfied myself and managed to clean up most of the jelly splattered around my home, but the place was still going to smell like fruit for a couple days. I’d need to finish cleaning up soon though: I didn’t want to get bugs. Trust me, it is a serious turn-off to a pony when the first thing they see in your home is a bunch of creepy-crawlies.

I ran into Blossom about halfway to the bakery. We waved and exchanged greetings as we fell into place alongside each other. After a few seconds of flying along the streets of Ponyville at a slow, leisurely pace, the white pegasus let out several loud sniffs and frowned over me. “I’m a little scared to ask, but why do you smell like grapes?”

I grinned over at her. ”Do you really want to know?”

Blossom grimaced. “Probably not.”

“Then I won’t traumatize your innocent virgin ears with the tales of my wild debauchery.”

“Thanks,” Blossom answered flatly, looking just a touch annoyed with me. Maybe I shouldn’t have brought up the V word; from how skittish she was about the subject, it was probably a safe bet that she didn’t have a lot of experience. Hay, for all I knew she might actually be a virgin. It’s not like I had ever just flat-out asked her or anything.

“Hey Blossom, are you a virgin?”

It was a good thing we were only a couple feet off of the ground, because as soon as her brain processed the question, Blossom’s wings locked up and she plowed face-first into the dirt. Maybe I shouldn’t have asked her that while we were flying. I helped her back up and gave her a quick once-over to see if anything other than her pride had been injured. “You okay Blossom?”

I guess I shouldn’t have been surprised that Blossom was too busy blushing and sputtering incoherently to answer either of my questions. Hay, just yesterday she’d barely even been able to bring herself to say the word ‘mate,’ so asking her about her sex life completely out of the blue might have been taking things a little too far. Her reaction was pretty darn hilarious, though.

Eventually, Blossom managed to recover her composure enough to indignantly declare, “That’s none of your business!”

“Which part?” I shot back with a smirk. “Being a virgin, or whether you’re alright after getting a faceful of dirt?” I thought about just leaving it there, but that wouldn’t be nearly as much fun as pushing her buttons a bit more. “Oh, by the by Blossom,” I faux-whispered to her. “Getting all huffy when somepony asks you if you’re a virgin is pretty much admitting that you are.”

“Why am I still friends with you?” Blossom whined.

“I’m just brimming with irresistible charm, remember?”

“Irresistible charm my hoof,” the girl grumbled. “I swear, I never should’ve talked to you. Everypony else on the weather team warned me about you, but I strike up one conversation with you on one shift, and now I’m stuck with you. Worst mistake of my life.”

“Blossom, you say the meanest things sometimes.” I tossed a foreleg across her shoulders and pulled her into an entirely one-sided hug. “It’s okay though, I know you don’t really mean it.”

“I totally and completely mean it.” Blossom insisted, though she couldn’t quite hide the tiny little smile on her face. “I hate you.”

“That’s silly, nopony can hate me. I’m far too lovable.”

Blossom half-heartedly tried to worm her way out of my hug. “You are not lovable.”

“Well now you’re just being ridiculous, Blossom. Everypony knows that I’m the most lovable pony in the history of Equestria. Seriously, I love everypony, and they all love me right back; in fact, I challenge you to name a single pony that doesn’t love me.”

“I don’t,” Blossom immediately chimed in.

“Well we both know that’s not true,” I promptly countered. “Hay, you spend way too much time hanging out with me not to love me.” I freed her from the involuntary hug and contemplatively tapped a hoof under my chin. “Well, unless this is all some kind of elaborate scheme to get into my pants, but that would be really pointless. By now you ought to know that if you wanted to bang, all you’d need to do is ask.”

“That’s not – I’m not–” Blossom really was too much fun to rile up sometimes. Eventually, her poor frazzled mind settled on the one thing it could handle. “You don’t ever wear pants!”

“I could if you want me to,” I shot right back, dropping my voice into a low, husky tone. I tossed in a suggestive little grin for good measure.

Judging by the frustrated scream Blossom let out, I’d pushed her to the breaking point. “You are, without a doubt in my mind, the single most impossibly aggravating pony I have even known in my entire life!”

“And yet, I’m still your best friend.” I took a few quick flaps into the air and struck a pose. “Do you know why? Irresistible. Charm.”

The two of us lapsed into a friendly silence for the rest of the walk to Sugarcube Corner, probably because Blossom couldn’t find any way out of admitting that she’d been taken in by my overflowing animal charisma. It’s a problem she seems to suffer from a lot.

Fortunately for the innocent children walking the streets of Ponyville on this fine day, we got to Sugarcube Corner before Blossom lost control completely and tried to make wild passionate love to me right then and there. It’s a common effect of overexposure to my charm. One time I forgot to turn off my charm before I went to bed and woke up the next morning with half a dozen mares I’d never seen before in my life, all under the covers with me.

No wait, that was just what happened on my last trip to Las Pegasus. Ah, good times.

I opened up the door to Sugarcube Corner, only to find that the shop was pitch-black. That was weird. The shop should’ve been open for a while now, and we were actually a minute or two late for our meeting with the boss. Maybe Rainbow Dash had gotten here before us, and she and Pinkie had gotten a bit “distracted” and closed the shop for bit?

The lights clicked on and revealed a room practically packed with ponies. “SURPRISE!”

Oh. That surprise party I’d been expecting. Apparently, Pinkie had figured that I expected the party to happen it last night and went and planned it for a time when I wasn’t expecting it. In hindsight, I should’ve expected that too.

I grinned over at Blossom. “See? I told you there was going to be a surprise party.” Sure, I’d gotten the timing wrong, but that was a minor detail.

She didn’t even respond this time, just facehoofed and walked the rest of the way into Sugarcube Corner. Well, Blossom’s already speechless? Sign of a good party!