Short Hand: Dates with Shepherd - Fluttershy · 4:02am Aug 3rd, 2020
Shepherd: I've known her the longest, and she's been fairly obvious... Okay blindingly obvious with her affections. So let's just man up and ask her. Clearly, she's too shy to just say it.
He knocks on Fluttershy's door
Fluttershy: Opens it "Oh... H-Hello Shepherd. It's so nice to see you, how are you?"
Shepherd: "I'm good. So. You want to go on a date with me this Venuday?"
Fluttershy: "..."
Shepherd: "... Fluttershy?"
Fluttershy: "..." Faints with a happy smile
Later, after the smelling salts are applied
Fluttershy: "Y-Yes... Yes, I will go out! Um... But... I've never been on a date before."
Shepherd: "It's okay. We'll take it slow. This Venuday at 6?"
Fluttershy: "That... That sounds wonderful."
Shepherd: "Great! I'll see you then."
Shepherd heads off. Fluttershy hums.
Fluttershy: "Oh... A r-real date. I... I'm just going to mess it up... Wh-Why can't he just ask me back to his home? Then we can... blush "N-No! No, Fluttershy. You can do this. But I could use... Some help." She looks at the brochure for Iron Will's assertiveness seminar "Hmmm..."
Later... Shepherd arrives with flowers dipped in chocolate. He's in a nice suit, made by Rarity. He knocks on the door with a smile.
The door slowly opens... And Fluttershy stands there in a sexy dress.
Fluttershy: "Hello Shepherd~..."
Shepherd: "Hello Fluttershy. You're looking very beautiful tonight. Flowers?"
Fluttershy: "Fluttershy isn't hungry for flowers right now..."
Shepherd: "Um... Okay? I got us a table at a nice, secluded restaurant-" Fluttershy grabs him and yanks him into her cottage "BWAH!"
THREE DAYS LATER...
At Ponyville General Hospital...
Doctor Stable: "Well Mister Shepherd, I'm sorry to say your pelvis is broken."
Shepherd: "... I really can't say I regret it... Though that just might be the painkillers talking..."
Fluttershy: sobbing "I'm so sorryyyyyy!"
Twilight: "How could you just jump him like that?!"
Rarity: "That's not fair, Fluttershy!"
Fluttershy: "You're right. I'm so sorry, everypony. I promise, everypony else can have s-s-sex with Shepherd too! It-It's only fair!"
https://derpicdn.net/img/2013/9/29/437397/medium.png
derpicdn.net/img/2013/9/29/437397/medium.png
To be fair, I felt the joke was much better the first way around when I read it at Spacebattles--with Shepherd ending the snip with "... I really can't say I regret it... Though that just might be the painkillers talking..."
This said, damn but that lady was thirsty!
Pity you couldn't keep it at the other site, but it was still funny--it is now personal headcanon for your fic. :)
I hope to see something like this happening in the overall story albeit less explicitly, as it would really be in-character for Flutters dear.
Fluttershy want snu-snu!
The spirit is willing, but the flesh is spongy and bruised.
BAD Fluttershy! First date, then hanky-panky
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When someone as repressed as Fluttershy is given assertiveness seminars it's very easy to go overboard. It's like she'd been hiding emotions in a closet and locking the door tight until one day she opens it and all the clutter spills out everywhere and then before you know it you've snatched him up thrown him on the bed and there is no getting off this ride anymore.