Milo🐆 @bullyjaguarmilo.bsky.social · 26/09/2026I love stretching my wedgie bros undies hehe, he’s lucky I didn’t pull them over his head 😏 #wedgie 17411
Reposted by Milo🐆Kobold Artsy (commissions closed) @koboldarts.bsky.social · 17/09/2026El Sol Diablo giving his fans the best personal experience with a professional wedgie wrestler El Sol Diablo belongs to @rookthederg.bsky.social 1114849
Reposted by Milo🐆jake250.bsky.social @jake250.bsky.social · 15/09/2026Atomic wedgie squats this morning 4388
Reposted by Milo🐆Ash"NERD"Wulfy @ashtomicwedgie.bsky.social · 15/09/2026Day 7: Prank War War's over. Time for a victory lap to admire the new campus decorations 😌 The losers @otterdownunder.bsky.social @cjtheott.bsky.social @cjfox.bsky.social @guitargoyle.bsky.social @kaithewah.bsky.social @paulmuttbishop.bsky.social #septENMber 1229063
Reposted by Milo🐆jake250.bsky.social @jake250.bsky.social · 11/09/2026Some fun with a jockstrap and briefs 12810
Reposted by Milo🐆HarryHarold40 @harryh4.bsky.social · 08/09/2026BREIFLY DETAINED Ransacking some rich hyena's mansion for valuables backfires on this Cat Burglar. This will be one hell of a police report... #wedgie #wedgieart #furry 735498
Reposted by Milo🐆COMMISSIONS OPEN - Argo @hidegreenfox.bsky.social · 23/08/2026mythical creature Com for @lolflip.bsky.social 420857
Reposted by Milo🐆Rated R Rabbit @bunbriefs.bsky.social · 12/08/2026Didn't get to post about it last week but HAPPY BELATED UNDERWEAR DAY!!! Who knew a piece of clothing could lead to so much mischievous yet arousing fun~ Art (and bully 🫣) is @toastyarchons.bsky.social! 614932
Milo🐆 @bullyjaguarmilo.bsky.social · 06/08/2026Happy Underwear Day! Had to pull out the boxer briefs my bestie gifted me for this😜 0143
Reposted by Milo🐆COMMISSIONS OPEN - Argo @hidegreenfox.bsky.social · 04/08/2026Crow's nest Com for @pangolinhiran.bsky.social 117345
Reposted by Milo🐆COMMISSIONS OPEN - Argo @hidegreenfox.bsky.social · 31/07/2026deep DEEP wedgie com for @thegreatmsteak.bsky.social 321866
Reposted by Milo🐆Warren @warrie.bsky.social · 25/07/2026Designated gym nerd.. 🎨 @harryh4.bsky.social 122758
Reposted by Milo🐆Ziggy the Wedgie Boy @otterdownunder.bsky.social · 20/07/2026Com for @reggieigulas.bsky.social! Oh jeeze that's precarious, better not slip or those undies are going in REAL deep! 1034285
Reposted by Milo🐆Rated R Rabbit @bunbriefs.bsky.social · 07/07/2026mfw when i am "reminded" last minute that it's national wedgie day via surprise turbo bouncing wedgie (🎨: @maverickdraws.bsky.social) 319451
Reposted by Milo🐆Kobold Artsy (commissions closed) @koboldarts.bsky.social · 02/07/2026Finally decided to get some payback on Iris. It didn’t turn out well. 1215243
Reposted by Milo🐆Rated R Rabbit @bunbriefs.bsky.social · 25/06/2026Blight too op pls nerf 🪝🩲 #wedgie Sweaty killer main: @possyeen.bsky.social Amazing art by @canecoum.bsky.social! 413929
Milo🐆 @bullyjaguarmilo.bsky.social · 17/06/2026I used to always prefer giving atomic wedgies, waistband over the chin, but now I kinda like it when the waistband is just over the eyes or forehead cuz then everyone can see the nerds flustered face and underwear brand better to add a bit more humiliation hehe😏 1211
Reposted by Milo🐆Kobold Artsy (commissions closed) @koboldarts.bsky.social · 07/06/2026Why are you asking this kind of question Iris!!! 816137
Reposted by Milo🐆Kobold Artsy (commissions closed) @koboldarts.bsky.social · 10/06/2026Time to raise them undies up high Wedgie Wednesday 514740
Reposted by Milo🐆Milo🐆 @bullyjaguarmilo.bsky.social · 08/05/2026The gym was offering a deal I couldn’t say no to… 🎨 by @canecoum.bsky.social 917647
Reposted by Milo🐆Kobold Artsy (commissions closed) @koboldarts.bsky.social · 06/06/2026I guess me getting a new card game set requires Iris to give me an atomic wedgie 1018144
Reposted by Milo🐆🏰Gutter Boy🦇 @ CFF @guitargoyle.bsky.social · 27/05/2026Since @donkdork.bsky.social was getting hungry up on that flagpole, Gutter decided to bring him a lil snack. 🎨: @koboldarts.bsky.social #art #furryart #furry #digitalart #gargoyle #wedgie 718742
Reposted by Milo🐆Smelly Bear🔞 @smellybear.bsky.social · 22/05/2026Marky let Andy pass with just a warning the first time, but he didn’t listen, so the kitty got some treatment that he’ll never forget to not cross paths with the burr again~ Comm for @andycougar.bsky.social ! Tysm :D🤎 #furryart 316540
Reposted by Milo🐆Kobold Artsy (commissions closed) @koboldarts.bsky.social · 18/05/2026Wedgied through the night Commission for @arkaidenva.bsky.social 119351
Reposted by Milo🐆COMMISSIONS OPEN - Argo @hidegreenfox.bsky.social · 17/05/2026Hazing Com for anonymous 018047
Reposted by Milo🐆🏰Gutter Boy🦇 @ CFF @guitargoyle.bsky.social · 14/05/2026Some cute cougar boy wanted to know what it’s like being an art installation all day. I don’t think this was what he had in mind. 😆 Gargoyle: Killian (me) Cougar: @andycougar.bsky.social Artist: @koboldarts.bsky.social #furry #art #furryart #digitalart #gargoyle #wedgie #tightywhities 719854
Milo🐆 @bullyjaguarmilo.bsky.social · 08/05/2026The gym was offering a deal I couldn’t say no to… 🎨 by @canecoum.bsky.social 917647
Reposted by Milo🐆Jojo @jojocorgi.bsky.social · 29/04/2026“Enjoy your time together, dorks! We’ll be back later this afternoon… maybe 😂” *SLAM* Welp, if I’m stuck in a locker at least I’ve got another cute nerd to keep me company 😵💫 🎨 by the masterful @brieflyy33n.bsky.social, thank you again 🥰❤️ 1340989
Reposted by Milo🐆Star F. @starfart.bsky.social · 29/04/2026Commission featuring www.deviantart.com/thorne07 and www.deviantart.com/wedgielover669 69622
Reposted by Milo🐆🏰Gutter Boy🦇 @ CFF @guitargoyle.bsky.social · 29/06/2025I love making men whimper~ 😈🥰 🎨 by @nukeyfox.bsky.social #bullyplay #wedgie #furry #furryart #art #digitalart 1232284
Reposted by Milo🐆Friday the 67th: The Final Fapter @actualcatguy.bsky.social · 17/04/2026And for our next trick, my assistant will make my undies disappear up my-huh wait a minute- Comm by @hidegreenfox.bsky.social featuring me and my (mostly) lovely @bunbriefs.bsky.social 🩷 422656
Reposted by Milo🐆Milo🐆 @bullyjaguarmilo.bsky.social · 21/04/2025Me and Riku dressed up as our favorite Rivals characters and I couldn’t resist giving him a legendary wedgie😏 Riku belongs to @stellarriku.bsky.social Amazing art by the one and only @brieflyy33n.bsky.social 619232
Reposted by Milo🐆Hatio @hatio.bsky.social · 07/04/2026Com for @lolflip.bsky.social I was trying to take the gym a bit more seriously, so I tried to ask one of the regular for pointers! He looks like he knows what he's doing. 😤 Unfortunately Ray smelled a nerd... 😭 1113137
Reposted by Milo🐆Silas! @brieflyy33n.bsky.social · 20/03/2026Not sure if said trophy is my underwear, or what's beneath,, 😳 1727962
Reposted by Milo🐆The Great Milksteak @thegreatmsteak.bsky.social · 18/03/2026Blood runs deep, but @goodquestion-awoo.bsky.social 's and I's wedgies go deeper. A wonderful comm from @brieflyy33n.bsky.social ! Thank you so much! 413744
Reposted by Milo🐆COMMISSIONS OPEN - Argo @hidegreenfox.bsky.social · 16/03/2026LIFT OFF!!! Com for anonymous 217348
Reposted by Milo🐆Kobold Artsy (commissions closed) @koboldarts.bsky.social · 17/03/2026Hector being the absolute menace that he is. Demolishing my undies, I think I’m be stuck like this for a while. Credits to @otterdownunder.bsky.social for the original animation and thanks for allowing me to make my own version. Your so awesome Ziggy 6492113
Reposted by Milo🐆Marty @glitch-dog.bsky.social · 15/03/2026Is this what they call a nuclear wedgie? Ft. @badluckmurphy.bsky.social 512631
Reposted by Milo🐆COMMISSIONS OPEN - Argo @hidegreenfox.bsky.social · 13/03/2026SWIRLIE TIME!!! Com for @wolfangcerberus.bsky.social and @asssherwulfy.bsky.social 436873
Reposted by Milo🐆COMMISSIONS OPEN - Argo @hidegreenfox.bsky.social · 12/03/2026Cat- I mean Deer crossing! Com for @sinfuldesire.bsky.social 628275
Reposted by Milo🐆Pakrat @pakratmaniac.bsky.social · 03/02/2026I can't believe I forgot to post this! Isaac wanted a pic with his favorite rat buddy but something was missing to really capture the moment. He did not miss it for sure 🎨: Hizunamasu_ (X/Twitter) 311927
Reposted by Milo🐆Ziggy the Wedgie Boy @otterdownunder.bsky.social · 17/02/2026Don't go hiking in the woods at night... The creatures of the forest have taken Eric (@stretchydeer.bsky.social) and I, and put us into a VERY compromising and EXTREMELY GAY position!! 20509125
Reposted by Milo🐆Ash"NERD"Wulfy @ashtomicwedgie.bsky.social · 31/01/2026Don't know if y'all have played the game "Back to the Dawn" but if you see Crunchy you better give him your lunch money or hope your undies break before you do 😣 Amazing art from @haxsmacks.bsky.social 735281
Reposted by Milo🐆Rated R Rabbit @bunbriefs.bsky.social · 14/02/2026Get yourself a wedgie wingman this Valentine's day to help ask your crush out! 😈💕 ft @jojocorgi.bsky.social Comm from the great @hidegreenfox.bsky.social <3 1325571
Reposted by Milo🐆Kobold Artsy (commissions closed) @koboldarts.bsky.social · 21/01/2026Mornings can be rough Featuring @warrie.bsky.social 520354
Reposted by Milo🐆Kobold Artsy (commissions closed) @koboldarts.bsky.social · 16/12/2025A wedgie selfie with my bully shark, Hector 623757
Reposted by Milo🐆Kobold Artsy (commissions closed) @koboldarts.bsky.social · 16/12/2025Tighty Whities Alt 010729