Author's Note

This story jumps around between perspectives a lot, and since it's second person, that means it's hard to indicate who the story is following right away. To deal with that, it was suggested that I put a little military operation code at the top. Should be simpler than trying to think of ways to indicate it otherwise.

Pickup Lines and Mixed Drinks

Umbral Dream Captain of 2nd Soma Company 2100 hours Status report: Slight buzz. Low morale.

The bar’s murmur had already become a muffled hum as you nursed your third drink. A comfortable buzz settled over you, making you feel pleasantly content despite what you were here for.

Your small table erupted in laughter, probably Night Sky telling another story of how to pick up stallions. Colts love a mare in uniform so she’d use that pretty often to pick up secretaries or a cute butler colt at the castle. The rest of her advice was pretty much the same old thing. Just be confident… go for it and be persistent… colts love the chase… and on and on and on. She said one time she even got a stallion to stick it in her butt. It’d take a lot more than a few drinks to believe that one though.

A new set of drinks clacked on the table, and you looked over to see a cute blue stallion in serving uniform. He gave your table a good natured smile as they complimented his figure, your friends leering at the poor guy like hungry diamond dogs. His eyes met yours and you blinked, your heart skipping. You should say something, Umbra, come on. Your head swam and you leaned forward then grabbed a drink, trying not to stare at him.

Uh… maybe say he has nice eyes? No, that’s a colty compliment. Say you want him inside you. You blushed. No way you could say that outright-It was going too far.

You opened your mouth and met his pretty blue eyes. Shoot, you can’t do this! You sat back suddenly, putting the drink to your mouth and taking a big gulp. When you finally put it down, fighting back a cough from the intense burn of the alcohol, he had left, off to serve other tables. You slumped down into your seat, a new pain in your chest as you watched the cute colt walk back. Might as well be a mile away…

Another round of laughter rolled through your friends, hooves pounding on the table while you just sat there, staring into the reflection in your drink. You didn’t think you were a bad looking mare. Kept your fangs neat, wings cleaned and lightly oiled to not get leathery and dry, your eyes were a brilliant shade of light orange, and you even had your mane cut just yesterday. Just… something never clicked when you saw colts titter and blush. And their mind games… it was like navigating a maze. They say they aren’t interested but sometimes that’s just a test, except when it’s not, and then you’re a misandrist.

They say they want to talk about feelings but if you do, their dick shrivels right up because they want a real mare. You let your chin sink down to the table with a light thud. Why couldn’t stallions just be simpler? Why couldn’t they just make the first move instead? You just...

”Oh and then he came, right there in the backdoor.”

”No way!”

”Luna, the feeling of that is kinky as all hell. I’d hit buttsluts any night of the year.”

... weren’t like your friends.

You felt Moon Dusk elbow you in the side. “Hey, Umbra, are you even paying attention? Tonight is to help you out, ya know. We’ll wingpony you up any colt you want, you just gotta’ tell us who.”

Your mouth twisted into a grimace and you set your drink down with a sigh.

“Look, girls, I don’t know. It feels like you’re tricking a colt into being interested. Besides, I don’t really even know if I want… you know.”

Your guard mates shifted forward, waiting on you as you gestured with a hoof. You sighed. “I’m just not super into the idea of like a one night type thing.”

Blue Shade quirked an eyebrow and made a face. ”What? You want to like screw again the next morning too?”

You ran a hoof down your face. “No, I just—”

”Nah, Bluey,” Night Sky said. “Umbra is the type to collect numbers and call up the stallions when she’s in the mood for ‘em. Keep a little fuckbook, you know? Hit it anytime, rather than once and done, right?”

You scrunch your muzzle.“N-No, Night Sky, listen to me. I meant that it just doesn't feel ri—”

”Oho, I get it, Umbra,” Moon Dusk said. “Are you one of those kinky bitches who wants to tie them up then? We can take you to a place for that in the lower quarter of Canterlot if you want. The colts down there love to be whipped till they’re screaming your name, and you can even have them lick your—”

“I don’t want to just fuck a stallion!” you yell.

Your friends go silent, looking at you wide-eyed as you sat up on the table. You looked around, panting and noticed the rest of the bar had gone quiet and were staring over at your table. Your ears snapped back, you cleared your throat and sat back down. The dull murmur resumed after a few chuckles.

“Damn stupid ponies. M-Mind your own business,” you mumble to yourself.

”You a fillyfooler or somethin?” Night Sky said.

You snapped your gaze over to her. “What? No, idiot, I just… I just don’t want to, okay?” you say, slumping back in the booth. “Can’t we leave it at that?”

Night Sky frowned, leaning closer to your face from across the table. “You okay, Umbra? I mean, you’re usually pretty grounded until we get you around colts. You spar like a boss and even the day guard colts respect you… Like, uh, what is it that her old platoon used to call her before she became a Captain?”

”Umbra, the midnight star,” Blue said.

”Right! Midnight Star,” Sky said, giving the name a kind of grand flourish.

You grumbled and kept your eyes to the table. “That’s such a lame nickna—”

Sky slapped a hoof to your mouth. “Captain Midnight Star, of the nightguard. You’re one of the toughest guard mares I know. You should be drowning in dick.”

“I don’t know if I want to drown in dicks…”

Night Sky scoffed. “You’re talking like a day-guard, softie colt. We’re gonna show you a good time, even if you’re too mopey to accept it, right girls?”

”Damn straight.”

”Hells yeah.”

Sky reared up, puffing her chest out and pointing toward you. “We’re gonna get our friend the best damn night of her life. Next colt walks through that door,” she said, gesturing toward the bar entrance with a flourish. “You move in, buy him a damn drink, and we do whatever it takes to make sure you get some hot, thick co—”

The door swung open, the bell at the top giving a chime, and a small gasp ran through your table. In walked a creature the likes of which you’ve never seen before. It was tall, with only a bit of fur on top of its head, and instead of hooves, the creature had two lithe hands.

It wore clothes all over, even socks, as if to tease at the form underneath to everyone here. You couldn’t help but drop your jaw at the grace of the creature as it walked confidently toward the front stools, like it owned the place, like there was no place they’d rather be.

Your gaze drifted down, searching for the teats this thing had to have to act so confident and your eyes came to rest on a bit of a bulge in the crotch area. Your cheeks bloomed red and you fought to keep your wings down.

H-Holy… A stallion?

“Right, uh, next one then,” Night Sky said.

You spun in your seat and gaped at Night. “What? What’s wrong with him? I, uh,” you looked to the side, clearing your throat. “I kinda think he’s hot.”

Blue Shade gave a nervous cough and muttered, “We’re not blind.”

”That’s Anonymous, and yeah, he’s definitely a looker, Umbra,” Sky said. “You don’t think an exotic thing like him isn’t being pined after by every other mare on a nightly basis?”

You moved your gaze over to the colt, who had already made himself at home on one of the barstools and was chatting and laughing with the bar stallion. Mares all through the room had hushed their conversations and cast glances over at the strange newcomer intermittently.

You deflated. You feel a bit dumb now. Of course a colt like him had the pick of anypony he wanted. Why would he choose a shy little mare like you? You weren’t confident, cool, or forward.

“Right,” you said slumping down, “I wouldn’t be his type. Figures. All colts want nowadays are the bad-flank mares.”

Blue gave you a smack on your snout from below. You reeled back up and glared at her.

“Ow. Blue, what was that for?”

”I’ll buy you a damn sunhat if you keep that up, Umbra. This mopey sourpuss thing doesn’t suit you.” Blue said. “Besides, he doesn’t like those types of mares anyhow.”

You quirk an eyebrow at her. “And how would you know what he does or doesn’t like?”

The table went quiet, the girls avoiding your gaze and clearing their throats or hiding their face in their drinks. You narrowed your eyes, scanning across their faces and landing on Moon Dusk. She always had the worst poker face, and was trying to hide her face behind her mug. Her eyes flicked to you, then to Anon, then to her drink. She gave a nervous gurgle into her drink as your eyes seared into her.

“You all tried to get him in bed, didn’t you?”

Moon Dusk sputtered, coughing up cider. ”M-Maybe! I mean no!” she said glancing at the others for backup.

Night Sky rolled her eyes. “Yeah, Umbra, we tried. But can you blame a mare?” she said, gesturing toward the stallion. “I can only imagine what those hand things feel like on your tuft… What it would feel like to bounce on his lap while he combs them through your mane and pulls your tail...”

She bit her lip, looking off at the colt before shaking her head clear. “Anyhow, the point is that he’s a regular around the Canterlot nightlife, but nobody can ever get him to go home with them. And let me tell you, mares have tried every angle to figure out what makes him spring.”

“So… the bad-flank thing you guys usually do didn’t work?”

”Tried twice already. Mooney even wore some leather biker gear too, and he just laughed at her and pet her head.”

Moon Dusk groaned and put her head in her hooves. “Don’t remind me.”

”The rich gal schtick?” you asked.

”Practically robbed a mare on expensive drinks and drank her under the table before leaving. That one happens maybe once every two weeks.”

“The uh… funny girl thing?”

Your friends stayed quiet, seeming to think about it.

Blue snickered. ”You’re welcome to try.”

“You’re kidding, that doesn't work either?”

”Oh he’ll be laughing. Just not at your jokes.”

Dang, you had some sick knock-knock jokes in your back pocket.

You let out a sigh and gave the colt one last forlorn look. Your eyes suddenly met and you realized he had been looking at your table. He smiled and waved and you turned rigid. By the mare in the moon, he was looking at you.

Quick, do something cool! You let out a tiny, nervous scree and blushed. W-What?! That was supposed to be ‘sup’! He smiled and gave the most beautiful deep chuckle you ever heard. You shot your gaze to the floor, not able to look into those emerald eyes any longer. Oh lords of shadow, he was laughing at you… Wasn’t he?

You chanced a glance up and saw that he was talking with the bartender again. A pit forms in your stomach, and you realize you secretly wanted him to look at you again. As you think about it for a moment, he didn’t really seem to be laughing AT you. He just seemed to be amused.

Honestly… even though you kind of felt like an idiot, part of you wonders what he was thinking. It was just a look, but there was something deep in it, like he could take you in with just a glance and see the best in you. If you could only be a fraction of what a glance like that seemed to see…

The door dinged and Night Sky banged the table, jostling you from your thoughts.

”Hey, Umbra, fresh meat just walked in. One with the tan coat and green vest. He’s packing, if you know what I mean. Go ahead and get him a drink before any other mares make a move. We’ll give you hints over his shoulder.”

You glanced over to the stallion. His coffee colored coat shone slightly under the bar lights as he looked around for a seat. He was cute, and he seemed to know it, taking survey around the room and noting glances. His eyes came to rest on you and… The look was different. He wore a smirk and flicked his tail, as if to show off and tease, and he lowered his eyelids just a fraction as he looked over at your table before looking away, as if to say he’s not interested just yet.

You frowned and your ears sunk back. It didn’t feel right. He looked at you more like sizing up a bounty, seeing which mare might come and approach him first to offer free drinks before he sat down.

You glanced back over at Anon, his smiling face making your heart flutter, even as he talked to the ponies beside him.

”Time’s ticking, Umbra. Mooney looks thirsty and ready to pounce. I’m calling him open to takers if you keep waiting.”

“I… I want to try.”

”That’s what we’ve been saying. Go for it. Toffee Spice is as easy as it gets.”

You shook your head, gaze not leaving Anon. “No… not Toffee. Him.”

Night furrowed her brow and tracked your gaze back to Anon. ”Oh for Luna’s sake. Have you not been listening to us at all tonight? You go after him and you’ll waste your bits, time, and he’ll just humiliate you like every other mare.”

You shrug. “Maybe he will. But I don’t know that yet.”

Your friend slapped a hoof to her face and muttered an oath under her breath. ”Fine. No routine ever seems to work, so just be confident I guess. That’s the most I can offer, sis.”

“I just want to go talk to him. Be myself and just say hi and see where that goes.”

She cringed. ”Oh you poor, sweet sun child. But to Tartarus with it. Give it a shot anyways. We’ll be rooting for you right here,” she said as you hopped out of the booth.

”Next round’s on me to cushion the blow when you get back,” Moon Dusk called out after you, earning herself a slap on the back of the head from Sky.

You took a deep breath and headed across the room, keeping your eyes on the open stool next to him. It was hard not to stare at him. His broad back had a bit of muscle moving beneath his shirt as he shifted around. The room seemed to feel hotter to you and your head felt light as you walked. Maybe you were in over your head… You closed your eyes and shook off the feeling. No, you had to just go. You skipped the last few feet and leapt up on the stool next to him.

Or at least that’s what you intended to do.

Instead, your half-stiff wings and nervous energy betrayed you, and you had just tuft checked the stool, letting out a grunt and sliding back off and to the floor. You could feel the eyes of the room turn to you, but you sat frozen in place as Anonymous turned and looked at you with a worried expression.

Oh Luna… You really just did that. D-Don’t cry, filly. Whatever you do, don’t cry!

You felt your cheeks heat up and your eyes started to water.

I SAID DON’T CRY!

In the corner of your eye you could see Night Sky gesturing like mad and mouthing ‘get up!’

“Hey, are you alright?” Anon said.

His voice came as a rich baritone that made your skin tingle and sent butterflies through your stomach. Your own voice got caught in your throat and you nodded, putting your ears back. You got to your feet, and he smiled down at you while resting a hand on his cheek. Not maliciously though—more like he was watching a little puppy who had gotten caught in a bramble and couldn’t get out.

“Here, let me help you. The stools can be a bit high.”

He grabbed you by the scruff of the neck like a foal, and you let out a little squeak as he placed you atop the stool, even taking a moment to put his hand through your mane to straighten it out.

You could see your friends giving mortified looks at their table. It looked like Blue said “He’s just toying with her,” and Moon Dusk “I can’t watch.”

You just looked up at Anon, still feeling spell struck. Should you be humiliated? Maybe… but… in a way it felt good. He was so gentle with you, and it didn’t feel like he was making fun of you or trying to emaresculate you. There was no malice playing out on his face when he picked you up.

He just did it...

“Um, thank you,” you said, surprised to hear your own voice.

He just smiled, gave a curt nod, and turned his stool around to lay his back against the bar, one elbow resting on the high table. Being this close made it hard for his scent not to envelope you and pull you in. His musk reminded you of a long day at training—a bit of sweat, but not body odor. The powerful sweetness of a colt… Not exactly fruity but tantalizing all the same.

You clenched your legs together and took a deep breath. Come on, keep it together. Stop thinking weird stuff.

“Hey, are you going to order something?” he said. You gave a start and looked over to Anon. ”You’ve just been staring out over the back glasses and breathing kinda strange…” He leaned down, lowering his voice. “Sorry, I’m just wondering—not trying to be rude. Name’s Anonymous, but most ponies usually just call me Anon. I haven’t seen your face here before, so I was wondering if you’re new, maybe you’d like a recommendation?"

Your face felt like an inferno with him this close. His size, and the muscle you could barely make out under his shirt made you wonder if he could overpower you. How easy would it be for a stallion like him to just… take any mare he wanted, when he wanted. He could do it even now, leaning over you like he is… he could pick you up like he owned you and take you out back. Anon could make you his mare—have you call out his name while he teased you.

A hand waved in front of your face.

“Hey uh… you okay? You look like you may have had a lot of cider already. Your face is all flushed.”

Nngh! Snap out of it Umbra, the colt is actually paying attention to you.

“O-Oh, I’m Umbral Dream. Um, s-sorry, you didn’t ask. I mean, well I’m not supposed to be sorry, but, I didn’t know if you cared so it’s just... ugh nevermind.”

You sighed and he gave that musical chuckle again, making the back of your neck tingle. He turned, laid a hand on your back and looked at you seriously.

”If you can’t focus, maybe you’ve had enough and should head home? I can call a carriage to make sure you get to the right place if you want.”

You sat up straight. ”No!” you said with more force than intended, and he raised an eyebrow at you. “Uh, I mean... I’ve only had a few ciders. If you think you know something good, I’d like to try it.”

He gave a smirk. “Alright, an adventurous type—just my kind of person. How about we try something easy that I think you’ll like, on me?”

You saw Night Sky give a throat cutting motion with her forearm. She mouthed “Don’t let HIM buy the drinks!”

Your eyes widened and you snapped to Anon. “Uh, a-actually I could—”

”Jaeger, mix us up two Applewoods. Put it on my tab like usual.”

“B-But…!”

The young stallion behind the counter gave a nod and started picking out containers.

“Um, I really should be the one to…”

Anon just turned and smiled at you. ”Hm? What’s up? Something on your mind?”

All your thoughts went out the window as you locked eyes. You felt your knees go weak and your head spun from more than just the alcohol. Luna, why is his smile so cute?!

You wanted to cry. Why was this always so hard for you? Come on, Umbra, the girls are counting on you. You clenched your eyes shut and took a deep breath.

”Anon, let me buy—”

The bartender turned and clanked the drinks on the counter. ”I charged 20 bits to your account.”

”Thanks, Jaeger Bomb. You were saying, Umbra?”

Your ears went back and you heard Night Sky’s head hit the table from across the room.

“Nevermind…”

The drinks sloshed inside clear glass, a pretty yellow and red mix that didn’t seem to blend, but rather slurred together. Might as well try it since it’s here now… You gave it a careful sip and your eyes widened.

“Wow this is… really good.”

Anon beamed at you. “Glad you like it. Super simple too. Just raspberry liqueur and pineapple juice with a few other things to make it look nice and give it a sour zing.”

“Yeah… Thanks. I can’t believe I’ve been sticking to cider when there’s stuff like this out there.”

Anon shrugged. ”A lot of mares don’t seem to like the fruity or sugary stuff for some reason. Always stick to hard cider.”

You pursed your lips. Oh… That suddenly made you feel a lot more self-conscious. You took another sip, almost, heat working into your cheeks as you imagined what a filly this made you look like in front of him. Oh well. You’ll get the next round. Just suck this one down, sister, and you can treat him to whatever he wants.