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Uploaded by Mildgyth
Best Pink Pony - For being the first person to reach 50k uploads, managing the site's featured images, and countless other contributions to the site.
Cutest Little Devil - Celebrated the 14th anniversary of MLP:FIM!
Rainbow Rocks 10th Anniversary: Sonata Dusk - Celebrated the 10th anniversary of EQG Rainbow Rocks!
Nightmare in the Moon - Had their OC in the 2024 Derpibooru Collab.
Pixel Perfection - I still call her Lightning Bolt
Silly Pony - Celebrated the 13th anniversary of MLP:FIM, and 40 years of MLP!
Shimmering Smile - Celebrated the 10th anniversary of Equestria Girls!
Lunar Guardian - Earned a place among the ranks of the most loyal New Lunar Republic soldiers (April Fools 2023).
Roseluck - Had their OC in the 2023 Derpibooru Collab.
King Sombra - Celebrated the 10th anniversary of The Crystal Empire!
A Lovely Nightmare Night - Celebrated the 12th anniversary of MLP:FIM!
Princess of Love - Extra special version for those who participated in the Canterlot Wedding 10th anniversary event by contributing art.
Elements of Harmony - Had an OC in the 2022 Community Collab
Non-Fungible Trixie -
Artistic Detective -
Kinship Through Differences - Celebrated the 11th anniversary of MLP:FIM!
An Artist Who Rocks - 100+ images under their artist tag
Twinkling Balloon - Took part in the 2021 community collab.
Ten years of changes - Celebrated the 10th anniversary of MLP:FiM!
Friendship, Art, and Magic (2020) - Took part in the 2020 Community Collab
Dream Come True! - Participated in the MLP 9th Anniversary Event
Wallet After Summer Sale -
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends
A Tale For The Ages - Celebrated MLP's 35th Anniversary and FiM's 8th Anniversary
Notoriously Divine Tagger - Consistently uploads images above and beyond the minimum tag requirements. And/or additionally, bringing over the original description from the source if the image has one. Does NOT apply to the uploader adding several to a dozen tags after originally uploading with minimum to bare tagging.
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Cool Crow - "Caw!" An awesome tagger
Not a Llama - Happy April Fools Day!
Speaking Fancy - Badge given to members that help with translations
Magnificent Metadata Maniac - #1 Assistant
Artist -
The 1% -
Perfect Pony Plot Provider - 10+ uploads with over 350 upvotes or more (Questionable/Explicit)
Fine Arts - Two hundred uploads with a score of over a hundred (Safe/Suggestive)
Derpibooru Premium - Learn about the benefits of subscribing to Derpibooru Premium membership at https://derpibo
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Description

Princess Celestia occasionally sends members of the royal court on an ‘important mission’ to investigate something, which is usually an elaborate practical joke on the one being sent. Still, it keeps life interesting, and since she has been around for over a thousand years I can see why it’s important to have fun like that.
 
Apparently kelpies (sea ponies) are more open about certain aspects between the mares and the stallions, or apparently between mares or stallions… but anyway you can see more of her adventures at Ask Windswept (NSFW)!

Tags
Edit History (4)
suggestive
196188 artist:jitterbugjive
862 oc
1012197 oc:pun
1597 oc:windswept
25 earth pony
552389 kelpie
914 pony
1713603 ask pun
1812 ask
28123 blushing
294174 comic
142404 female
1914674 implied fingering
172 mare
815882
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4 comments posted
d1ckbitch
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Non-Fungible Trixie -
Hard Work - Merited Perfect Pony Plot Provider badge with only their own art
Perfect Pony Plot Provider - Uploader of 10+ images with 350 upvotes or more (Questionable/Explicit)
Birthday Cake - Celebrated MLP's 7th birthday
Artist -

Doughnuts Worshipper
Now that’s a blast to the past. Things were great when the guy who created Windswept actually had the opportunity to freely create content for the fans to enjoy…
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