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Pony Driland fic!

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“I do believe,” Celestia said with a smile ghosting across her face. “That when one is in checkmate, one is supposed to surrender rather than move another piece to put their oppressor into check.”
 
She couldnt be angry, even at the blatant disregard for chess etiquette, however. When was the last time a pony had given her such a game, a clever mind doing its best to outsmart the ruler of Equestria itself? Only an occasional chess game with one of the members of the Shaman Council of the Savannah tribes had come close.
 
Celestia forced herself to think away from thoughts of how her sister might have played were she still here to look at her conquest across the board. She liked this stallion. Ever since the previous treasurer had run off to Mexicolt with half a million bits in his saddlebag, his junior had stepped up to the role admirably.
 
Polite visits to her apartments to keep her up to date with the workings of the castles funds had become welcome rather than the dreariness of the previous stallions lectures, and Fancy Pants was more than impartial to a game, to have lunch, or even to go out to the races with.
 
She couldnt remember whose idea it had been to try strip chess. The idea had excited her somewhat though, and she played even more carefully as a result. Fancy was good, and forced her a few times into a few embarrassing moments. He was at least a gentlecolt enough to avert his eyes when she wriggled out of something tight.
 
“I had to have one last act of defiance, ma’am,” Fancy said with a smile, running his hand through his mane. “I do intend to beat you some day,” he added with a laugh. Celestia responded with a giggle of her own, feeling like quite the schoolfilly.
 
“I’m terribly afraid that wont happen today, Fancy,” she said affectionately. “In fact, if you ever do beat me, I may have to curse you with a moustache for life. Every great military leader needs one,” she teased, a wink closing over one magenta eye. “However a gentlecolt should always accept defeat. Now why don’t you take off your own Fancy Pants for a change?”

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Liggliluff
Best Artist - Providing quality, Derpibooru-exclusive artwork
Helpful Owl - Drew someone's OC for the 2018 Community Collab
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Artist -

Playing a strip game against a girl in a dress is the best way to do it ;)  
Although, even if the girl was wearing a top and bottom separately, taking either off would still reveal underwear ;)
Etherchanter
My Little Pony - 1992 Edition
Not a Llama - Happy April Fools Day!
The End wasn't The End - Found a new home after the great exodus of 2012

Perpetual lurker
“So, Mr. Pants. How does a gentlecolt such as you acquire such an elegant mustache?”
 
“Ah yes, the mustache. Say, Isn’t that the Princess over there?”