Mysty and: Obamacare's First Time

by MysticDriveFiM

Rating: mature
Tags: Comedy, Sex, My Little Pony: Friendship is Magic, Romance, Original Character, Porn
Length: 2224

When meeting up with Obamacare, Mysty learns that he just needs a little tender love.

Obamacare has grown very lonely and is in desperate need of some affection. When Mysty finds this out, she decides to take control and help him through this trying time.

[Influenced from an ERP in the RolePony Discord with the permission of all involved parties]

Published 2019-07-16 22:00:01 UTC
Last updated 2019-07-16 22:00:01 UTC

Character Overviews

Mysty is a pretty little blue mare. She has a short lighter blue mane with a bright yellow streak around her horn. Her gorgeous blue eyes out-shine the rest of her features. She's a caring individual with a heart for entertaining others. She can't stand anything out of place or messy, but loves to have some fun.

Obamacare is the edgiest pony you'll meet in the streets. Aside from listening to Linkin Park and playing Shadow The Hedgehog, this cyborg Alicorn loves to just chill hardcore. His lust for his first encounter is the only thing that overcomes his love for the color black.

Introduction

Mysty is happily trotting down the street when she sees somepony jamming out on the sidewalk.

"Ooh, whatcha listening to?"

"Hm? Oh, I'm listening to Skillet. Hardcore." He's hardcore.

"Whoa, I like Skillet!" Mysty chimes in.

"Whoa, dude... you do, dude? Whoa..." Obamacare's attention shifts to the mare.

"Yeah, I listen to an odd assortment of songs." Mysty approaches closer and sits next to him.

"We should, like, totally hang out, dude!" He says, excitement lighting his face.

"Sure, I'm down." She replies, as Obamacare's robotic eyes turn to hearts.

"Say, d-d-d-d-d-d-dooooooo, are you, like, in a relationship or anything?" He asks through a voicebox malfunction. This catches Mysty off guard.

"Oh, uh... Not really, no."

"Say, like, are you looking for, like, a relationship or anything? Because, like, my name is Obamacare and I like... care..." Obamacare is now fully enthralled in Mysty. She has clearly caught on and matches her vibe to his.

"Nah, dude. Relationships are gnarly. I just, like, go with the flow, y'know?" She leans back to look more relaxed.

"Dude I, like, never got in one because, like.... they just don't care enough and, like... I do.." His gaze droops down to the road as he seemingly drifts off into a daze.

"Caring is important, man. Nopony else gets it." Mysty chimes in, trying to return his attention.

"Well, I can care for you, if, like... you want..." He turns back towards her.

"Oh?"

"You can, like.. totally choose how. Like... friends... best friends... friends who like each other... ETC.. whatever ETC means.." Obamacare looks lost in thought.

"ETC is short for etcetera, which implies a continued list." She notices him returning a blank stare. She breaks the awkwardness with a wink "Sorry, uh, yeah. We can hang out."

"Oooh, and maybe, like, advance? If you'd like? I just want some mare to, like... like... like..." Obamacare adjusts himself "To just like me, man..."

"Aww. I'll like you, big guy." Mysty puts a hoof around him.

"Wait... in, like... what kind of way? Also I'm, like, shorter than you..."

"Just trying to boost your confidence, man. In any way you want that's not too sappy." She clarifies with a smile.

"I'd ask ya... but I can, like... you're not that lifestyle."

"Not really, no."

"Well.. I might never get a girlfriend... but I want to at least know what... sort of things it feels like..." Obamacare's cheeks emit a deep red as he boops Mysty on the snout.

"Oh!" She chuckles. "Don't worry, you will one day."

"M- maybe... you would be so kind as to show me... dude?" Mysty now too shows slight bashfulness.

"I--would love to."

"I don't want to go all of the way... there is stuff I'd want to save for a future love..."

"Of course. So, uh... you got a place?" Mysty looks around to make sure nopony is listening to them.

"Uh... I mean... my parents' basement. Do you got one?"

"I do, actually. Why don't you follow me?" Mysty stands up and begins trotting down the street.

"Alright miss... um... w- what's your name?" Obamacare falls in pursuit.

"Oh! You can just call me Ms. Mysty. Or Myst. Whatever suits you." She flicks his snout with her tail.

Obamacare's First Time

"Welp, here we are. Not too big, not too small." Mysty guides Obamacare into her home.

"That's totally what she said."

Mysty laughs as she guides the two into her living room. They sit down upon her squishy maroon couch and continue their conversation when Obamacare pipes up a question.

"Well, what sort of stuff do... people do in a relationship?" He gives her a questioning glance.

"Well..." Mysty slowly scoots closer to him as he begins heavily blushing. She sits him back further against the couch and bends down. Obamacare can't take his eyes off of her lips. Mysty shoots a kiss at him before moving her forehoof over to his leg.

"A- Ahh... w- wait... this is a b- bit soon... how about we start off... small?" Mysty freezes and sits back up.

"Uh, smaller? Like... what?" She notices him awkwardly leaning in as if wanting to kiss her. She slides over and sits on his lap, giving him a cool peck on the lips. Feeling her body press against his causes Obamacare to let out a soft moan as they begin kissing.

Mysty slowly guides him into making out, trying to teach him how to move his tongue. As he weakly follows she tries to get him into a rhythm of breathing and kissing. After a minute, Obamacare breaks the silence

"W- was I... a good kisser?" He swallows.

"You're a good learner." Mysty replies, giving him a nice smile.

"What comes... after this?" Mysty slides her head down and rests on his leg. "Many things can~."

"C- care to, uh, demonstrate these... things?" He mumbles out. Mysty slowly gives his tip a long lick before smiling back up at him. He moans soflty. "S- so... foreplay?"

"If you want."

"Y- yeah... only if you want to..."

"Lead the way~."

Obamacare shifts his position. He can't take his eyes off of her crotch. She notices and chimes in. "So what are you looking to do?"

He snaps back to reality "M- maybe... something together?" He reaches his forehoof over and gently brushes it against her, eyes wide.

"Oh~ Well, you just take your time and do what feels comfortable~."

"Maybe you... can rub me? After I... rub... you?"

Mysty lets out a small chuckle. She sits up and turns around, then falls onto her back. "Ready when you are~." She rests her hooves and parts her thighs. Obamacare leans in and leisurely massages her marehood with one hoof. "Is it good?"

"Of course~." She replies, closing her eyes. A soft moan rises out of her chest. Obamacare rubs harder.

"mmn~" She moans as he adjusts his pace. She starts letting out light pants after a second.

"Hehe..." He leans over her and kisses her cheek as he continues sliding his hoof on her. She lets out a blush and stares back up at him.

"Cum when you want... if you want to..." Mysty can't help but giggle. "That's n- not how t- that works, mmn~"

"Wait, what?"

"I c- can't just cum whennnn I want to. Though it m- might be sooonn~." She states through the growing pleasure. Obamacare picks up the pace.

"hnng-aah~!" Her body lets out small convulsions. "I-m-!" She gasps.

"A- are you okay?! I- i can stop!"

"No please continue!"

Obamacare speeds up again as he spreads her lips and fondles her clitoris. Mysty lets out a high-pitched squeak as she reaches her climax. Her head leans back and her body falls limp as she begins panting. "You did great, Obamacare, thank you~."

"Good, hehe!"

Myst takes a moment to get up, then returns them to their positions from earlier. She looks up at him. "I'll go real easy for you. Ready?" She bends over his lap and places her tongue on his tip.

"Y- yeah... just... be careful..."

Mysty slides her muzzle under his shaft and licks at the base. She moves her head back and places her lips around his tip. As he softly moans, she bobs her head down slightly, licking circularly around him. She begins rubbing his base with her forehooves to the rhythm of her head bobbing.

"That... feels amazing..." Mysty stops to get a breath and licks at his testicles before returning to her job.

"I- um... I'm not into ball stuff... just so you know..."

"Oh?" She pulls her head back up. "I'm sorry. I should have asked. What stuff are you into, then?"

"Well... stuff on my... shaft." He looks down at himself.

"Like, spit?"

"No, I mean, like... you doing stuff to it."

"Like this?" Mysty slowly eases into deep-throat.

"D- don't force yourself... I don't want you hurt..."

Mysty comes up for air. "If you don't like it, that's easier for me. But if you do, I'll be fine. Trust me." She licks her lips and awaits his response.

"I- I like it... just do whatever makes you comfortable and s-safe..." Obamacare closes his eyes and Mysty dives back in. She switches between slow deep-throats and licking while rubbing. "Aaaahhh~" She swallows his pre-cum as it comes up.

"Ah- ah! AH!" Seeing the mare on him and feeling her touch makes him suddenly finish. "Ah!"

Mysty shockingly tries to swallow as much as possible, but the surprise at how quickly he came left her unprepared. A bit leaks out and makes a small mess. Mysty gulps "Gah- uh... sorry!"

"Don't be sorry... t- thank you." Obamacare leans in and gives her a big hug.

"Oh!" She embraces his hug.

"Yo dude, like... shame that you don't do romance..." He mentions through red cheeks. Mysty giggles.

"Sorry, it's just not for me. I've tried it before. You're always welcome over, though~."

"O- okay-" His words are interrupted by her giving him another full kiss. "Mmm... You're a good friend."

"Aww, thanks sweetie~. I'm glad I could help you out." She sits back in the couch. After a moment of a break, Obamacare gets a question.

"Yo, like... what do girls... like? In general. I mean, man..."

"Sexually?"

"Yo... I mean, like... what they want in a man..."

Mysty takes a moment to ponder before replying. "Well, that always varies. Everypony likes something different. I'm into really intellectual, funny, studious guys as a basic overview of my own tastes." She sighs. "Never try to be what others like. Just be who you are and find that special somepony that likes the real you."

"R- really?"

"Of course, honey. Trust me. Now, that doesn't mean somepony like that is always readily available and searching for you, too, but if it's meant to be it'll happen

Obamacare blushes as he zones out and stares out of the window, then looks back into Mysty's eyes. "I- I hope so."

"Don't worry~." Mysty leans back in and gives him another kiss. Obamacare couldn't get more red if he tried. "So what do you want to do now?"

"Get to know you, maybe."

"Oh, uh, sure." Mysty gets comfortable on the cushion opposite from him and looks over.

"What do you do for a living?"

"I'm an entertainer. I like to make stuff for others. What about you?"

"I'm a DJ."

"Oh! That's super cool. I'd like to hear you sometime."

"Y- you think so?" Obamacare stares into her eyes.

"Of course."

"I never had anybody think I was cool before..."

“I’m sure you have. You just don’t know it.”

"Like you?"

“Of course, I think you’re cool.” She smiles at him.

"Yay!" He moves over and gives her a hardy hug, clearly overexcited.

"Whoa! Uh, yay!" She struggles to breathe.

"Oh! Sorry, sorry." He drops the hug and drops his head.

Mysty takes small gasps. "You're fine."

Obamacare begins shedding small tears. "I'm sorry..."

"O- oh...? What's wrong?" She leans over and puts a hoof around him.

"I thought I hurt you..."

"No! Not at all. That was just a tight and unexpected hug."

"I feel bad..."

"You have no reason to."

"O- oh..." He wipes his eyes.

"Here, I know something that might make you feel better." Mysty rests her hooves on his shoulders as she sits on his lap and presses up against him.

"H- huh?"

Mysty looks into his eyes and smiles, waiting to see if he's brave enough to make a move yet. He kisses her cheek. She moves in and starts making out with him again. "mmh~" She presses their crotches together as he resumes blushing.

Mysty halts the kiss and leans back, staring at the confused stallion. She moves over to another cushion and leans over the back of the couch, wiggling her butt at him. She patiently waits for him as he begins stammering through words.

"M- Mysty... um... uh..."

"St- still too much?"

"I... I can't do this... n-not to you of all people..."

“I’m--not sure what that’s supposed to mean?” Mysty sits back down and looks at him.

"B-because... it'd be too emotional for m-me..."

Mysty sighs. “Alright. I’m getting kinda hungry. I’m gonna go eat. Feel free to join me if you want.”

"Wait!" Obamacare grabs her hoof, heart pounding. "It's not you... it's just... I- I-"

“I understand, but I think we both have different goals, Obamacare.”

"Oh... okay. Can we at least be friends, then?"

"Of course!"

"And maybe... sometimes... can you help me settle my emotions?"

Mysty giggles in response. "Any time, dude. Good luck out there."

"Can I go eat with you?"

"Sure, come on."