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Uploaded by RainbowDash69
Eden Shallowleaf - For supporting the site
Lunar Supporter - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
Perfect Pony Plot Provider - Uploader of 10+ images with 350 upvotes or more (Questionable/Explicit)
Non-Fungible Trixie -
Preenhub - We all know what you were up to this evening~
Twinkling Balloon - Took part in the 2021 community collab.
Emerald - For users who have donated to the site
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
Toola Roola - For helping others attend the 2019 Community Collab
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
Happy Derpy! - For Patreon supporters
Bronze Supporter - Bronze Patron
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Birthday Cake - Celebrated MLP's 7th birthday
Thread Starter - Automotive enthusiasts?
Not a Llama - Happy April Fools Day!
Artist -
The End wasn't The End - Found a new home after the great exodus of 2012
 2838x4000 PNG 5.83 MB
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Pony Driland fic!

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2260198 artist:witchtaunter
980 izzy moonbow
23665 pony
1691674 unicorn
577766 g5
85135 ball
5759 clothes
674571 commission
127150 cuffed
344 cuffs
6808 horn
237505 hornball
864 izzy's tennis ball
1239 never doubt rainbowdash69's involvement
425 prison outfit
1805 prisoner
1282 prisoner im
67 shackles
2659 solo
1499854 tennis ball
1595
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14 comments posted
Background Pony #EB72
Izzy: Why… why imprison us Sprout?
Sprout: SHUT UP AND GET IN THE CELL!!
Posted Report
RainbowDash69
Eden Shallowleaf - For supporting the site
Lunar Supporter - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
Perfect Pony Plot Provider - Uploader of 10+ images with 350 upvotes or more (Questionable/Explicit)
Non-Fungible Trixie -
Preenhub - We all know what you were up to this evening~
Twinkling Balloon - Took part in the 2021 community collab.
Emerald - For users who have donated to the site
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
Toola Roola - For helping others attend the 2019 Community Collab
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
Happy Derpy! - For Patreon supporters
Bronze Supporter - Bronze Patron
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Birthday Cake - Celebrated MLP's 7th birthday
Thread Starter - Automotive enthusiasts?
Not a Llama - Happy April Fools Day!
Artist -
The End wasn't The End - Found a new home after the great exodus of 2012

Visit Friendship Daily!
@Gooeygaster
Hehe that was probably me or my friend Land24! In fact I even have a group on deviantart called IncarcerationIsMagic
We’ve been doing this for years now. I don’t even know why either at this point. But it all started from watching too many episodes of Lockup and Cops when I was younger 😆
Posted Report
Gooeygaster
Artist -

Benjamin
is there some kind of kink with ponies in prison outfits? when i was a kid on deviantart someone requested i draw twilight sparkle in an orange jumpsuit and i still dont understand why
Posted Report