Cupcake Half Full

by Uh-hmmm

Rating: teen
Tags: Human, Anon, My Little Pony: Friendship is Magic, Second Person, Sad, Caramel, Slice of Life, Sex
Length: 4000

Caramel decides to take Anon out drinking. It doesn't quite work out. (RGRE) {This story has two versions, the last chapter is the first person version.}

Caramel decides to take Anon out drinking. It doesn't quite work out. A bittersweet look at a more grounded RGRE.
(RGRE)
{This story has two versions, the last chapter is the first person version.}

Published 2020-12-01 04:20:01 UTC
Last updated 2020-12-01 04:20:01 UTC

Second Person POV

You are Anon, Pinkie Pie's underling. You happened to show up as the Cakes were thinking about retiring, and none of the free locals had a baking cutie mark. Of course, you don't either, but Pinkie took one look at your gut and (correctly) assumed you could bake. For some reason, Pinkie was a little worried the first few days you were at the register, but you do mental math well enough to handle the calculations. It helps that there is only one coin in the Equestrian currency system, so making change is not really an issue. The ponies themselves are perfectly friendly, some more than others. Caramel comes by at the end of your shift.

"Hey Anon, want to get some drinks?"

You shrug and hang up your apron.

"Sure, why not?"

You've been trying to lose some weight, but it's the weekend, and you will only get a drink or two. Caramel claps his hooves together excitedly and practically drags you to The Swan Dive. You look around and notice an awful lot of pegasi milling around with drinks in their wings. Caramel doesn't seem bothered and leads you straight to the bar. The two of you sit on the stools, Caramel only half-sitting, extending his other hind leg to his side. The bartender has a dark grey coat and a light-yellow mane draped over her shoulder, tied in a knot and wedged in a shot glass. She smiles at Caramel and glances at you.

"What would you like? It's Lord's night, so it's on the house."

Caramel rubs his chin.

"I'll have a blueberry bop. What about you, Anon?"

You skim the chalkboard, but there are simply too many unfamiliar choices. You shrug helplessly.

"Do you have a root beer? Uh, sassafras?"

The bartender nods with a smile.

"One bop and 'fras, got it."

It's kind of interesting, watching her mix Caramel's drink with her wings and forehooves juggling bottles and lids around. She finishes with a flourish, sliding a oblong glass of blue liquid to Caramel. She then grabs a mug and fills it from a soda fountain. When you get your drink, there's a decent amount of foam, and you take a sip. It's an odd flavor, a little richer than the store-bought root beer from back home. Caramel is barely paying attention to his drink, scanning the room with half-lidded eyes. You say,

"So what is lord's night? Some sort of holiday?"

Caramel glances at you with a smile.

"You could say that. Once a week, stallions drink for free at bars. That brings in the mares, it's a win-win."

You blink.

"Oh, like ladies' night. Actually, why isn't it ladies' night? I would expect there to be more guys champing at the bit, er, no pun intended, to try to pick up a girl."

Caramel fully turns to look at you with a bemused expression.

"What are you talking about? Even if the ratio was equal, no stallion worth his salt should need to pick up a mare, that's their job!"

You think back. Are there more mares than stallions? You think your customers were pretty evenly split, but then again, out in the marketplace...

"Huh. I never really noticed."

Caramel frowns.

"Surely, you've had mares hitting on you before?"

You scratch your chin.

"Uh, maybe? Pretty much everyone says I'm a sweet guy, so I don't think it counts as getting hit on."
Caramel takes a gulp of his drink.

"Well, uh, it's not important. Just...if I bang the bar twice while a mare is talking to me, bail me out, okay?"

You raise your eyebrows, but nod anyways.

As the night goes on, the occasional mare will drop by and chat with Caramel for a few minutes, maybe even offer to buy him a drink. You're kind of amazed you never noticed it before, the way mares act around him. Flirtatious, smiling, eyes wandering. After a few approaches, though, you get an inkling as to why you never picked up on it. Most mares barely glance at you unless Caramel mentions you by name.

You...

Aren't particularly surprised, to be honest. You still have that gut, after all, and you never really thought of yourself as handsome. You nurse your drink some more, keeping Caramel in your peripheral out of a sense of duty.

"Hey, uh, you new in town?"

You turn to find a blue-violet pegasus mare with a long teal mane, wearing a pink bow. You smile politely.

"I've been here a few months, working down at Sugar Cube Corner. My name's Anon."

She smiles back.

"I'm Flitter, nice to meet you. How do you like Ponyville so far?"

You shrug.

"It's pretty nice, everybody's pretty friendly, the pay is good, can't complain."

Flitter nods.

"Things have really settled down recently. Used to be a monster attack or something every six months to a year."

You raise your eyebrows.

"Sounds exciting."

She wiggles her wings.

"After the first few times, it's just tedious to wait while the Elements take care of it."

You nod, having heard of them in passing. It's hard not to, when a substantial amount of Ponyville is a tourist trap for fans of the Elements. You glance at Flitter's cutie mark, three dragonflies. Entomologist, perhaps?

"So, what do you do for a living?"

Flitter preens a little.

"Ponyville Weather team, along with my sister. She's the one talking to your friend over there."

You look, and sure enough, Caramel is laughing with a mare with the same coat color, though her mane is light blue and spiky. The mare waggles her wings at Flitter, who frowns faintly. Flitter turns back to you and scoots a little closer. She smiles at you in a way that doesn't reach her eyes.

"You know, you're a sweet guy, maybe we can talk more in private?"

It takes you a moment to realize what is going on. You feel your face grow warm and your heart quicken. You try to play it cool.

"Sure, uh, your place or mine?"

Flitter raises an eyebrow.

"Can you walk on clouds?"

You blush.

"Oh, no, right. Um. My place it is."

She giggles. You stand up and glance at Caramel. It seems he was waiting for this, because he immediately hops of his stool and Flitter's sister puts a wing around him as the four of you make for the door. The night air is cool, and you relax, no longer hearing the murmur of the bar. Caramel leans against his date and winks at you as they head towards his house. You swallow and glance down at Flitter.

"I'm this way."

As you walk towards your apartment, Flitter walks about two or three feet to your side. And she's not looking at you at all. Your heart sinks.

"Playing wingmare?"

Flitter stops and looks at you, a blank expression on her face. You stop too, your shoulders slumping.

"It's...it's okay, I get it. I think Caramel was holding out for something like that, for me."

The pegasus mare frowns.

"Anon, I..."

You wait, but she doesn't know what to say. You rub your neck.

"Let's just end it here. It was nice meeting you, Flitter."

She relaxes a little, and gives you a small, sincere smile.

"You too, Anon. You're a sweet guy, I'm sure there's a mare for you out there."

With that, she takes off into the night sky, and you amble on home.

The next morning, you open up Sugar Cube Corner. Pinkie Pie takes one look at you and zips in and out the kitchen. You end up with a chocolate cupcake in your hands, a smiley face drawn in icing on top. You give her a wry smile.

"I'm trying to lose weight, you know."

She tuts.

"That's a special cupcake, it goes to your heart instead of your stomach. No calories."

You laugh at the nonsense.

"We should make all our sweets like that."

Pinkie shakes her head vigorously.

"Nuh-uh, it's only for friends and family when they need it. Otherwise it wouldn't be special!"
You nod seriously.

“Can't argue with that."

You take a bite, and you have to give the mare her due, she makes a good cupcake. Caramel comes waltzing during the slow time, grinning from ear to ear. You keep wiping the tables as he approaches.

"That was some night, eh, Anon?"

You shrug.

"Had fun with Flitter's sister?"

Caramel licks his lips.

"You don't know the half of it. Pegasi have the best tufts for burying your face in and just letting your instincts take over. And Cloudchaser? She knew what she was doing, edged me good until I came so hard I couldn't see for an entire hour afterwards. She's definitely going in my little black book. How about you? Did Flitter take care of you alright?"

You shrug.

“Didn't work out."

Caramel blinks.

"She couldn't get it wet, or got called on an emergency, what?"

You decide to play a little trick on him.

"Well, when I got undressed, she was looking rather pale."

Caramel leans forward, a worried expression on his face.

"And when I got hard, she took one look and threw up all over the floor."

Caramel gasps. Pinkie Pie drops from the ceiling. You frown sadly.

"Then she said that she only went along with me so that Cloudchaser could have a chance with you."

Caramel drops his head onto the table and moans.

"I'm so sorry Anon, I never thought it would end like that."

Pinkie is chanting to the elder gods, a dread gleam in her eye. You laugh.

"I'm just joking, you two. After we left the bar, we talked a little more and decided to part ways. No harm, no foul."

Pinkie gives you a flat look.

"That special cupcake? Straight to your hips."

You roll your eyes.

"As if it was going anywhere else."

Pinkie giggles and bounces away. Caramel doesn't raise his head, his ears pinned back in shame.

"I really am sorry, Anon. Flitter's a good mare, I thought she'd treat you right."

You sigh.

"She's alright. I'm not romantic enough to save myself for the perfect mare, but I would like my first time to occur because of mutual attraction."

Caramel pales.

"You're a virgin?"

You raise an eyebrow.

"Yeah?"

He mumbles, "I thought, a janefilly with his own kind would... you know..."

You snort.

"Turns out I'm just as attractive back home as I am here."

Caramel groans.

"I'm a terrible friend, trying to make you lose your virginity in a bar!"

You pat him on the withers.

"Yeah, that wasn't great. At least you were trying to be a good friend, I can appreciate that much."

He wraps you in a tight hug. You can't help but smile at the genuine warmth. You hug him back for a few minutes, then pat him on the back. He lets go and looks up at you.

"Will you be alright?"

You nod.

"I'll be fine, thanks. Now, if you'll excuse me, I should get back to work."

Pinkie Pie calls out, "You can have an hour paid break if you kiss!"

Caramel scrunches. You roll your eyes.

"Not happening."

"The day off, if you tenderly hold hooves in the window booth?"

Caramel isn't any happier with the second offer. He frowns at you.

"She may be an Element, but you don't have to take that kind of harassment."

You wave your hand dismissively.

"It's all in good fun."

Pinkie Pie grins, then disappears into the kitchen. Caramel shakes his head.

"Suit yourself. Let me make it up to you, I'll take you to the spa on Sunday."

You nod in acceptance.

“That does sound nice, I'll see you tomorrow."

"Until then! Good luck, and slap Pinkie for me."

You laugh and see him to the door. You get back to work, a smile on your face and in your heart.

First Person POV

I am Anon, Pinkie Pie's underling. I happened to show up as the Cakes were thinking about retiring, and none of the free locals had a baking cutie mark. Of course, I don't either, but Pinkie took one look at my gut and (correctly) assumed I could bake. For some reason, Pinkie was a little worried the first few days I was at the register, but I do mental math well enough to handle the calculations. It helps that there is only one coin in the Equestrian currency system, so making change is not really an issue. The ponies themselves are perfectly friendly, some more than others. Caramel comes by at the end of my shift.

"Hey Anon, want to get some drinks?"

I shrug and hang up my apron.

"Sure, why not?"

I've been trying to lose some weight, but it's the weekend, and I will only get a drink or two. Caramel claps his hooves together excitedly and practically drags me to The Swan Dive. I look around and notice an awful lot of pegasi milling around with drinks in their wings. Caramel doesn't seem bothered and leads me straight to the bar. The two of us sit on the stools, Caramel only half-sitting, extending his other hind leg to his side. The bartender has a dark grey coat and a light-yellow mane draped over her shoulder, tied in a knot and wedged in a shot glass. She smiles at Caramel and glances at me.

"What would you like? It's Lord's night, so it's on the house."

Caramel rubs his chin.

"I'll have a blueberry bop. What about you, Anon?"

I skim the chalkboard, but there are simply too many unfamiliar choices. I shrug helplessly.

"Do you have a root beer? Uh, sassafras?"

The bartender nods with a smile.

"One bop and 'fras, got it."

It's kind of interesting, watching her mix Caramel's drink with her wings and forehooves juggling bottles and lids around. She finishes with a flourish, sliding a oblong glass of blue liquid to Caramel. She then grabs a mug and fills it from a soda fountain. When I get my drink, there's a decent amount of foam, and I take a sip. It's an odd flavor, a little richer than the store-bought root beer from back home. Caramel is barely paying attention to his drink, scanning the room with half-lidded eyes. I say,

"So what is lord's night? Some sort of holiday?"

Caramel glances at me with a smile.

"You could say that. Once a week, stallions drink for free at bars. That brings in the mares, it's a win-win."

I blink.

"Oh, like ladies' night. Actually, why isn't it ladies' night? I would expect there to be more guys champing at the bit, er, no pun intended, to try to pick up a girl."

Caramel fully turns to look at me with a bemused expression.

"What are you talking about? Even if the ratio was equal, no stallion worth his salt should need to pick up a mare, that's their job!"

I think back. Are there more mares than stallions? I think my customers were pretty evenly split, but then again, out in the marketplace...

"Huh. I never really noticed."

Caramel frowns.

"Surely, you've had mares hitting on you before?"

I scratch my chin.

"Uh, maybe? Pretty much everyone says I'm a sweet guy, so I don't think it counts as getting hit on."
Caramel takes a gulp of his drink.

"Well, uh, it's not important. Just...if I bang the bar twice while a mare is talking to me, bail me out, okay?"

I raise my eyebrows, but nod anyways.

As the night goes on, the occasional mare will drop by and chat with Caramel for a few minutes, maybe even offer to buy him a drink. I’m kind of amazed I never noticed it before, the way mares act around him. Flirtatious, smiling, eyes wandering. After a few approaches, though, I get an inkling as to why I never picked up on it. Most mares barely glance at me unless Caramel mentions me by name.

I...

Aren't particularly surprised, to be honest. I still have that gut, after all, and I never really thought of myself as handsome. I nurse my drink some more, keeping Caramel in my peripheral out of a sense of duty.

"Hey, uh, you new in town?"

I turn to find a blue-violet pegasus mare with a long teal mane, wearing a pink bow. I smile politely.

"I've been here a few months, working down at Sugar Cube Corner. My name's Anon."

She smiles back.

"I'm Flitter, nice to meet you. How do you like Ponyville so far?"

I shrug.

"It's pretty nice, everybody's pretty friendly, the pay is good, can't complain."

Flitter nods.

"Things have really settled down recently. Used to be a monster attack or something every six months to a year."

I raise my eyebrows.

"Sounds exciting."

She wiggles her wings.

"After the first few times, it's just tedious to wait while the Elements take care of it."

I nod, having heard of them in passing. It's hard not to, when a substantial amount of Ponyville is a tourist trap for fans of the Elements. I glance at Flitter's cutie mark, three dragonflies. Entomologist, perhaps?

"So, what do you do for a living?"

Flitter preens a little.

"Ponyville Weather team, along with my sister. She's the one talking to your friend over there."

I look, and sure enough, Caramel is laughing with a mare with the same coat color, though her mane is light blue and spiky. The mare waggles her wings at Flitter, who frowns faintly. Flitter turns back to me and scoots a little closer. She smiles at me in a way that doesn't reach her eyes.

"You know, you're a sweet guy, maybe we can talk more in private?"

It takes me a moment to realize what is going on. I feel my face grow warm and my heart quickens. I try to play it cool.

"Sure, uh, your place or mine?"

Flitter raises an eyebrow.

"Can you walk on clouds?"

I blush.

"Oh, no, right. Um. My place it is."

She giggles. I stand up and glance at Caramel. It seems he was waiting for this, because he immediately hops of his stool and Flitter's sister puts a wing around him as the four of us make for the door. The night air is cool, and I relax, no longer hearing the murmur of the bar. Caramel leans against his date and winks at me as they head towards his house. I swallow and glance down at Flitter.

"I'm this way."

As I walk towards my apartment, Flitter walks about two or three feet to my side. And she's not looking at me at all. My heart sinks.

"Playing wingmare?"

Flitter stops and looks at me, a blank expression on her face. I stop too, my shoulders slumping.

"It's...it's okay, I get it. I think Caramel was holding out for something like that, for me."

The pegasus mare frowns.

"Anon, I..."

I wait, but she doesn't know what to say. I rub my neck.

"Let's just end it here. It was nice meeting you, Flitter."

She relaxes a little, and gives me a small, sincere smile.

"You too, Anon. You're a sweet guy, I'm sure there's a mare for you out there."

With that, she takes off into the night sky, and I amble on home.

The next morning, I open up Sugar Cube Corner. Pinkie Pie takes one look at me and zips in and out the kitchen. I end up with a chocolate cupcake in my hands, a smiley face drawn in icing on top. I give her a wry smile.

"I'm trying to lose weight, you know."

She tuts.

"That's a special cupcake, it goes to your heart instead of your stomach. No calories."

I laugh at the nonsense.

"We should make all our sweets like that."

Pinkie shakes her head vigorously.

"Nuh-uh, it's only for friends and family when they need it. Otherwise it wouldn't be special!"
I nod seriously.

“Can't argue with that."

I take a bite, and I have to give the mare her due, she makes a good cupcake. Caramel comes waltzing during the slow time, grinning from ear to ear. I keep wiping the tables as he approaches.

"That was some night, eh, Anon?"

I shrug.

"Had fun with Flitter's sister?"

Caramel licks his lips.

"You don't know the half of it. Pegasi have the best tufts for burying your face in and just letting your instincts take over. And Cloudchaser? She knew what she was doing, edged me good until I came so hard I couldn't see for an entire hour afterwards. She's definitely going in my little black book. How about you? Did Flitter take care of you alright?"

I shrug.

“Didn't work out."

Caramel blinks.

"She couldn't get it wet, or got called on an emergency, what?"

I decide to play a little trick on him.

"Well, when I got undressed, she was looking rather pale."

Caramel leans forward, a worried expression on his face.

"And when I got hard, she took one look and threw up all over the floor."

Caramel gasps. Pinkie Pie drops from the ceiling. I frown sadly.

"Then she said that she only went along with me so that Cloudchaser could have a chance with you."

Caramel drops his head onto the table and moans.

"I'm so sorry Anon, I never thought it would end like that."

Pinkie is chanting to the elder gods, a dread gleam in her eye. I laugh.

"I'm just joking, you two. After we left the bar, we talked a little more and decided to part ways. No harm, no foul."

Pinkie gives me a flat look.

"That special cupcake? Straight to your hips."

I roll my eyes.

"As if it was going anywhere else."

Pinkie giggles and bounces away. Caramel doesn't raise his head, his ears pinned back in shame.

"I really am sorry, Anon. Flitter's a good mare, I thought she'd treat you right."

I sigh.

"She's alright. I'm not romantic enough to save myself for the perfect mare, but I would like my first time to occur because of mutual attraction."

Caramel pales.

"You're a virgin?"

I raise an eyebrow.

"Yeah?"

He mumbles, "I thought, a janefilly with his own kind would... you know..."

I snort.

"Turns out I'm just as attractive back home as I am here."

Caramel groans.

"I'm a terrible friend, trying to make you lose your virginity in a bar!"

I pat him on the withers.

"Yeah, that wasn't great. At least you were trying to be a good friend, I can appreciate that much."

He wraps me in a tight hug. I can't help but smile at the genuine warmth. I hug him back for a few minutes, then pat him on the back. He lets go and looks up at me.

"Will you be alright?"

I nod.

"I'll be fine, thanks. Now, if you'll excuse me, I should get back to work."

Pinkie Pie calls out, "You can have an hour paid break if you kiss!"

Caramel scrunches. I roll my eyes.

"Not happening."

"The day off, if you tenderly hold hooves in the window booth?"

Caramel isn't any happier with the second offer. He frowns at me.

"She may be an Element, but you don't have to take that kind of harassment."

I wave my hand dismissively.

"It's all in good fun."

Pinkie Pie grins, then disappears into the kitchen. Caramel shakes his head.

"Suit yourself. Let me make it up to you, I'll take you to the spa on Sunday."

I nod in acceptance.

“That does sound nice, I'll see you tomorrow."

"Until then! Good luck, and slap Pinkie for me."

I laugh and see him to the door. I get back to work, a smile on my face and in my heart.