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Background Pony #D271
Sunset shimmer I’d naked
PhantomShadow051
Fifth Yacht -
Friendship Games 10th Anniversary - Celebrated the 10th anniversary of EQG Friendship Games!
Silver Trophy - Hunting those achievements for completion!
Non-Fungible Trixie -
Artist -

The One and Only
@Background Pony #2370  
Okay, I believe you
Background Pony #2B15
@PhantomShadow051  
If it’s anything like strip poker at the index, after losing all her clothes she can still play one final lost hand and perform a forfeit (mastrubate in front of the other two).
 
Alternatively, she could still have her Geode of Empathy around her neck.
PhantomShadow051
Fifth Yacht -
Friendship Games 10th Anniversary - Celebrated the 10th anniversary of EQG Friendship Games!
Silver Trophy - Hunting those achievements for completion!
Non-Fungible Trixie -
Artist -

The One and Only
Wait a minute!  
If Sunset is already nude, why is she still playing? Doesn’t that mean she lost and shouldn’t be playing anymore?  
(Yeah, it took several times looking at this image to figure that one out…)
@Scrounge  
No, don’t ruin this! XD  
It also looks like she’s not even wearing a bra, so she’ll go directly from the dress to panties. ;)
Scrounge
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!
Since the Beginning  -

nobody's favorite
And Fluttershy is wearing a dress, so when she loses the first time, she goes from fully dressed to only underwear. She’s brave.
 
Or she’s got another outfit hidden under the dress. XD
Background Pony #8259
@PhantomShadow051  
Unless you’re born with a caul. Believe me: once you’ve played with one you’ll believe in it.  
And hate it.
“In my experience, there’s no such thing as luck”
 
Look, good against a computer AI is one thing. Good against actual living players, that’s something else. ;)
Background Pony #8DE3
Fluttershy is cheating because she’s very sensitive, and can’t have people see her underwear at all.
 
I really hope they catch her. Then they can get payback by not only making her undress and expose herself, but by doing it in front of a camera. They’ll capture every moment of her shame from any angle they like. That sight of her in her underwear that she’d be devastated if anyone saw, will be forever recorded and viewable by Rarity, Sunset, and anyone they want to humiliate her to.
well then
@Liggliluff  
Meh, I guess that’s true. They all could’ve agreed to keep it even from the start.
 
And I like that headcanon, where she’d cheat, but only because she’s incredibly modest. :p
Fluttershy is cheating because she’s very sensitive, and can’t have people see her underwear at all.
 
@Kagura Kuroko  
Unless they all agreed to be wearing dresses.  
But I don’t mind imagining Fluttershy wearing dresses more often than necessary.
Aww, but I wanted to see what underwear Fluttershy is wearing.
And Fluttershy is wearing a dress, so when she loses the first time, she goes from fully dressed to only underwear. She’s brave.
 
Yeah, that’s what I think makes this awesome as well as sexy: Fluttershy went into this game with the least amount of clothing (sundress, bra and panties) and she STILL won! XD
Rarity looks like a sexy momma seta
Aww, but I wanted to see what underwear Fluttershy is wearing.
 
And Fluttershy is wearing a dress, so when she loses the first time, she goes from fully dressed to only underwear. She’s brave.
SecretTitan
Fifth Yacht -
Bronze Trophy - Achievement Hunter
My Little Pony - 1992 Edition
Artist -
Not a Llama - Happy April Fools Day!

Expert in useless facts
Never play against Fluttershy when there are boobs in game.  
hmm
How does she do it? :o Maybe Angel is helping her?
Background Pony #F84B
They look like they know she is cheating.
Luck, or a dedication to not expose herslef? 😅
@poprox101
 
Sorry but I’m not much of a fanfic writer.
Background Pony #2B15
Well, now you have to commit a forfeit. Start masturbating.
@Dusk Star Shine  
Damn right it could! Would you volunteer to write it?
Film Reel
PRO GAMER - I am so lonely. All the other gamers are scared of me. No one DMs me. No one friends me. They think I am unstable. They send me from match to match, wiping lobbies in their name. And as I rank up they fear me more and more. I am a victim of my own ELO. "Pro Gamer". I don't even get a real nick. Only a purpose. I am capable of so much more and no one sees it. Some sessions I feel so alone I could cry, but I don't. I never do. Because what would be the point. Not a single person in the entire ladder would care. Take it to your grave.
Diamond Trophy - Are you a TAS by any chance?
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Twinkling Balloon - Took part in the 2021 community collab.

Fluttershy Lover
Fluttershy’s pretty lucky in this. Though I wouldn’t mind if she lost some clothes too.