Luna gets a T-shirt with OPPAI on it, and tight shorts-Which do nothing for teenaged Shepherd's hormones. Celestia remains in naked apron mode, though she put on some racy panties. Clearly, both princesses-er, principals-are still massive trolls no matter what universe.

Celestia: "How is your omelet, Shepherd?"

Shepherd: "It's fine..."

Luna: glare "I got the mushrooms especially for you."

Shepherd: "Uh... Thank you?"

Luna: "Hmph."

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The repairs to Canterlot after the Changeling invasion were still taking time, and Shepherd was technically part of the decision makers. So he'd spent the entire day helping with the repairs, directing guard rotations, and filling out reports to hopefully ensure something like this never happened again.

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Shepherd: "So... What are we doing on our date, Rainbow Dash?"

Dash: "Ah... Well, ya know, dates are stupid and romantic and junk. So you just make the decisions there. You want to do mushy stuff and all."

Shepherd: "Okay. How does a trip up to Cloudsdale to the Wonderbolts museum, then dinner at the Skyview Cloud?"

Dash: "Yeah, sure, that sounds pretty okay. I'll need some girly clothes. What do you like?"

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Shepherd: "Hey Twilight? I got your mail for you. Huh, what's this magazine? Predator Fetish Monthly?"

Twilight: bright red, snatches it away with her telekinesis "Th-That's about scientific inquiries into the religious practices of certain predator groups and tribes and definitely not pornographic in any way whatsoever ahahahaha!"

Shepherd: "... Okay?"

Fluttershy: "Hello Twilight! I just got the latest issue!"

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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?"

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Shepherd tries to Help Twilight Sparkle

After Twilight Sparkle ascended to Alicorn, and became a Princess, her relationship with Shepherd didn't change too much. He was already a knight assigned as the guard for the Elements of Harmony after all. He did have a lot more duties involving her though. Unfortunately they usually involved paperwork.

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Shepherd took the revelation that Doctor Whooves and Ditzy had a time travelling, dimension-hopping muffin-shaped TARDIS quite well.

Shepherd: "HOLY FUCKING SHIT WHAT THE PUS SPEWING FUCK-!"

But after he was able to compose himself, breathing into a paper bag in the main control room of the Muffin...

Doctor: "Now now, everything is all right!"

Shepherd: "So... You think you can get me home?"

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Tea Time at Twilight's Palace...

Fluttershy: "You know Twilight, you've been spending a lot of time on reforming villains."

Twilight: "Well, what can I say? You inspired me! With the work you did with Discord! Now he's... Completely... Devoted to you..."

Fluttershy: deadpan "Twilight. No."

Twilight: "I-I didn't do-I'm not doing anything!"

Fluttershy: "I know you! You're going to concoct some kind of... Crazy scheme!"

Twilight: "Am not!"

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Twilight saw her other friends. All of them twisted and changed by the harsh war. It was heartbreaking to see them all like this. Fighting for their lives to save Equestria. And there was Shepherd...

He walked to a shack, and Twilight followed him. He looked over his shoulder at her.

Shepherd: "Something I can help you with?"

Twilight: "I... You're human."

Shepherd: "And you're an alicorn."

Twilight: "What?! How did you-?!"

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Shepherd is studying in the library. This isn't surprising. But what is surprising to Twilight is who he's studying with-Pinkie Pie!

Shepherd: "So, there is a similar mass extinction cycle in this planet's natural history?"

Pinkie: "Looks like! Maud's been doing research into it! And it's nice to meet another person who can understand what she's talking about!"

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Andrew somewhat reluctantly stepped into the library, having received a letter from Twilight asking for his presence.

The fact it was a letter, and she hadn’t just come over to talk to him, or asked somepony to speak to him next time they saw him, was slightly ominous. Either something official, or ‘hijinks’ were looming on the horizon.

Either way, he felt his trepidation was justified.

However, no one seemed present.

“Twilight? Spike? It’s Andrew. I came? About your letter?”

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Consider this a rough draft...
- - -
So, our lovely mares and Shepherd had to go and try and get a dragon to leave the area around Ponyville. His 'nap' might last for a century, and the smoke he emitted would make it unlivable. However... Fluttershy was terrified of the prospect of confronting a dragon.

Frankly, so was Shepherd.

Fluttershy: "Um... I mean... Maybe we could just... Just move the town?"

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Nightmare Night, and Shepherd is chilling out and enjoying the festivities.

Dash: "Hey Shepherd! Eh? Who are you dressed as?"

Shepherd: "I'm the Doctor!"

Dash: "Doctor Who?"

Shepherd: "Actually the Eleventh but..." At Dash's blank look, he sighs "Nevermind."

Dash: "Anyway, you look like... A dork! Especially with that bow tie!"

Shepherd: "Bow ties are cool, thank you. I was just going to go see Fluttershy."

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Shepherd has finished his morning training with Chewie. He walks up to his house, where the Elements of Harmony are relaxing in his backyard.

Shepherd: sigh "Why do you always hang out in my backyard?"

Pinkie: "You don't change your locks often enough!"

Dash: "Wow Pinkie. Just going out with that?"

Pinkie: "It's a joke, silly! Shepherd knows this!"

Applejack: rolls her eyes "We also brought food and booze."

Shepherd: "You're immediately forgiven."

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After the Changeling Invasion and the wedding, Shepherd was trying to relax in the armor and weapons from the Ancient Human Archives he'd pilfered for the fight in a small, unoccupied room in the palace. After some time, Princess Celestia entered, sat down next to him, and began eating cakes too.

Shepherd: "... You okay?"

Celestia: "... Shepherd. Do you think I'm weak?"

Shepherd: "Huh?"

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At Canterlot Palace, Shepherd is pacing back and forth and trying not to trip over his own cape.

Blueblood: "The entire Crystal Empire fleet is heading this way, Your Dreadfulness."

Shepherd: *groans* "Oh good! More pressure! I don't suppose we could just tell Shining this is all a wacky sitcom plot?"

Raven: "Alas my Dark Lord, he is unlikely to believe you."

Applejack: "To be fair, he does kinda hate yer guts anyway."

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Among the other artifacts of humanity in the Everfree Dump was, of all things, the fully armed and operational turret of an Iowa-class battleship, all three 16 inch guns intact.

And Pinkie Pie got to it first.

Pony: "Oh thank Celestia you're here Miss Pie! The children are getting restless! They tried to eat Shepherd!"

Shepherd: "Back! Back!"

Pinkie: "Time for the big guns!"

Pinkie Pie pulls out a field radio.

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Shepherd: "To celebrate our lil' alicorn's birth, I suggest we name the mixture of soft serve vanilla ice cream blended with cookies and/or candies as a Flurry!"

Shining: "Why do I feel like that's a joke or reference to something?"

Shepherd: "Well Flurry is my second suggestion. My first is what she wants to be called."

Candence: "What she wants to be called?"

Shepherd: "Oh yes. All humans can speak Baby."

Twilight: "Really?! You never told me that! What is she saying?"

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Shepherd was summoned to Princess Celestia's private office. He sat down across from her on a couch. She sat across from him with a smile.

Celestia: "Thank you for coming, Ser Shepherd."

Shepherd: "Not at all, Your Highness. What can I do for you?"

Celestia: "It's more something I'd like to do for you, Ser Shepherd."

Shepherd: "For me, Your Highness? What would that be?"

Celestia: smiles "There are concerns about you in Parliament."

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Shepherd was doing some financial stuff at his kitchen table, when the doorbell rang. He got up and walked up to it, and opened it. There was Pinkie Pie, with... Several gray ponies.

Pinkie: "Hi Shepherd! My family is in town, and they wanted to meet you! This is my dad Igneous Rock Pie, my mom Cloudy Quartz Pie, and my sisters Limestone and Marble Pie!"

She grins happily, while her family remains very stoic.

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