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Uploaded by northern haste
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!
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (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!
Cool Crow - "Caw!" An awesome tagger
A Really Hyper Artist - 500+ images under their artist tag
Elements of Harmony - Had an OC in the 2022 Community Collab
Non-Fungible Trixie -
Kinship Through Differences - Celebrated the 11th anniversary of MLP:FIM!
Verified Pegasus - Show us your gorgeous wings!
Preenhub - We all know what you were up to this evening~
Twinkling Balloon - Took part in the 2021 community collab.
Ten years of changes - Celebrated the 10th anniversary of MLP:FiM!
Fine Arts - Two hundred uploads with a score of over a hundred (Safe/Suggestive)
My Little Pony - 1992 Edition
Friendship, Art, and Magic (2020) - Took part in the 2020 Community Collab
Dream Come True! - Participated in the MLP 9th Anniversary Event
A Really Classy Artist - 250+ images under their artist tag
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
Equality - In our state, we do not stand out.
An Artist Who Rocks - 100+ images under their artist tag
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Magnificent Metadata Maniac - #1 Assistant
Birthday Cake - Celebrated MLP's 7th birthday
Artist -
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Edit History (5)
suggestive
191823 edit
174281 edited screencap
91363 screencap
297059 windy whistles
2947 pony
1620149 g4
2046044 parental glideance
1258 cute
268052 female
1820367 image macro
40301 meme
94344 milf
13477 solo
1439046 truth
1111 windybetes
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49 comments posted
Alexlayer
Perfect Pony Plot Provider - Uploader of 10+ images with 350 upvotes or more (Questionable/Explicit)
The End wasn't The End - Found a new home after the great exodus of 2012

Eternal Flame
I feel like she’s maybe the youngest MILF of the bunch, with the exception of perhaps Cadence (but who cares about Cadence) and possibly Ditzy depending on what headcanons you follow. I dunno, just a feeling I’m getting.
Posted Report
Background Pony #BA77
With her i think Milf ranking is:  
  1. Button’s mom  
  2. Twi Velvet  
  3. Flutter’s mom  
  4. Windy Whistles  
  5. Cloudy Quartz  
  6. Mrs. Cake  
  7. Cookie Crumbles
     
    Maybe i forgot others (Cadence for me is not Milf), and Milf OC maybe count too…
Posted Report
Edited
BigBuggyBastage
Pixel Perfection - I still call her Lightning Bolt
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Non-Fungible Trixie -
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!

Go fsck yourself
@EPPony  
Pretty much.
 
Except for AJ’s mom. I don’t think we can have dead or ‘historical’ Pones included, otherwise it would take the rest of our lives to figure out who to name Top MILF.
Posted Report
Background Pony #626A
I really think your kids need to be adult in order to be considered a MILF. So Windy qualifies but not Cadence.
Posted Report
Arcane Aegis
Wallet After Summer Sale -
Equality - In our state, we do not stand out.
Not a Llama - Happy April Fools Day!

IDK wth is going on
I’d rather not get into this kind of discussion since I’d rather someone in my age group but you’ve my vote, ma’am.
Posted Report
Background Pony #20A7
Guys, it’s pretty hard to argue that the mother of Rainbow “IWTCIRD” Dash is the best MILF. After all, RD is the best at EVERYTHING (just ask her) and thus her mom Windy Whistles must be the best too.
Posted Report