#Wedgietober2026
October 3, 2026 at 1:53 PM
October 4, 2026 at 5:51 PM
#wedgietober2026 Day 1: Atomic

The man has always been the quiet and composed type. He rarely seeks attention and usually prefers to stay out of trouble.

Unfortunately, trouble seems to have a habit of finding him first.

And today is no different.

#wedgietober2026 #wedgie #man #bully #Oc
October 2, 2026 at 3:37 PM
Halloween is coming soon, so it's time to grab your pens and stretch your tighty whities! >:3

#wedgietober2026
September 15, 2026 at 3:20 PM
Day 5: Hahahaha now everyone can see how dorky they are.

#wedgie #wedgietober2026 #calzonchino
October 5, 2026 at 10:59 PM
Day 4: Frontal atomic

It wasn't uncommon for Laval to end up in embarrassing situations. As soon as Worriz and Cragger saw the lion's waistband peeking out, they seized the opportunity, revealing the embarrassing pair he was wearing

#wedgietober2026 #wedgie #chima #legendsofchima
October 5, 2026 at 2:30 AM
Day 3: Squeaky Clean

You should never brag about how popular and cool you are, especially in front of your friends, otherwise, they'll make you even more popular, but for the most embarrassing reasons.

#wedgietober2026 #wedgie #pokemon
October 4, 2026 at 6:23 PM
Day 1: Atomic

Sometimes Leoner can't draw in peace. Apparently, drawing has to include an atomic wedgie from his attractive boyfriends... especially if he enjoy it~

#wedgietober2026 #wedgie
October 2, 2026 at 4:11 AM
#wedgietober2026
Day 2 - Hanging

Did Argit actually think stealing from a big bulky guy with four muscular arms would go well for him?
October 2, 2026 at 7:39 PM
Something feels wrong... why do I feel so horny.... whats that?!? FUCKKKKK 🤤🤤🤤
happy fat cock friday 😈

DAY 2 OF #WEDGIETOBER2026 EXPOSED
October 2, 2026 at 4:02 PM
#wedgietober2026
Day 1 - Atomic

Brooklyn should learn to never play 'truth or dare' with his clanmates if he's wearing underwear. Specially tighty whities.
October 1, 2026 at 5:48 PM
I love waking up on a Sunday morning, grabbing a cup of hot choclate in the morning, ripping my tighty whities right over my head, and spending time enjoying the view on the balcony 🥰

Day 4 of #WEDGIETOBER2026 ATOMIC
October 4, 2026 at 4:30 PM
#wedgietober2026
Day 4 - Frontal Atomic

Guess it doesn't matter how many lightsabers you have; you gotta prep better when going up against a specially creative jedi...
October 4, 2026 at 6:41 PM
Day 2: Hanging

Vitaly thought it would be easy to perform with Alex at his show, but he never imagined that a small mistake would leave him hanging from his speedo, Luckily (or embarrassingly) the audience thinks it's part of the show

#wedgietober2026 #wedgie
October 3, 2026 at 3:56 AM
Day 1 - Atomic

With the start of October, @ghostybaby.bsky.social had already begun some preparations for their costume. However, it seems it didn't stop him from giving a particular piece a good "stretch test" beforehand. Safe to say they had passed.

#wedgietober2026 #wedgie
October 2, 2026 at 4:57 AM
Day 5: Public

As he was getting ready for his show, Foxy heard a laugh before feeling someone grab his waistband, realizing what was about to happen. Before he could react, he was pulled up off the floor, revealing his shameful humiliation to the audience

#wedgietober2026 #wedgie #fnaf
October 6, 2026 at 7:28 AM
#wedgietober2026
Day 3 - Squeaky Clean

Must be nice to have your favorite husbandos (no homo) flossing your undies with all their might. Maybe after they'll make out and make you watch.

(Sí, dibujé al Zowl xD me daba demasiada risa esta idea como para no hacerla)
October 3, 2026 at 6:20 PM
Wedgietober2026 Day 4 - Frontal Atomic

A little late with this upload! 😅

I’ve been taking some extra time to finish the artwork, so I’m slowly catching up with the challenge.

#Oc #Digitalart #Draw #Man #Bull #Wolf #Bully #Wedgie #SuperWedgie
October 6, 2026 at 12:21 PM
#wedgietober2026
Day 5 - Public

Crime doesn't pay, but it seems Duke Weaselton will never learn that lesson. Clawhauser's already lost count of how many times Nick has left the weasel wedgied at the foot of his desk to be laughed at by the whole police station.
October 5, 2026 at 6:50 PM
I wish, I wish, with all my heart
For my undies to fly and be ripped apart 🌠

Day 5 of #WEDGIETOBER2026 WISH
October 5, 2026 at 4:02 PM
Chill music to relax and wedgie to 🎧🎶

1st day of #WEDGIETOBER2026 JAMMING

So excited for another month of y'all seeing my underwear crammed up my butt! Im traveling most of the month so alot of it I did in September but excited to finally show them off
October 1, 2026 at 4:04 PM
Day 2 - Hanging

Usually when getting bullied, the victim would try to fight back whether they can win or not. For Biker Seegs however, he found it was more easier to simply accept it.

So, he simply sighs as he watches his biker buddy work on their bike while he swings.

#wedgietober2026 #wedgie
October 2, 2026 at 8:46 PM
Wedgietober Day 4: Frontal Atomic - Pete Kowalski
Jimmy has a bad day and Petey's undies are the closest stress toy around. #Wedgietober #Wedgietober2026
www.deviantart.com/lunarlaser/a...
Wedgietober Day 4: Frontal Atomic - Pete Kowalski
www.deviantart.com
October 4, 2026 at 4:10 PM
It is almost time for WEDGIETOBER2026!!!!

I love my yearly tradition and im excited to play around with my undies up my butt. As always, would love to see someone join me on this month of wedgies!

Anything in () is what inspired the day
September 1, 2026 at 5:12 PM
Halloween is almost here, so hehehe I had an idea! Leave your OCs and costumes and I'll choose 10 people.

Clarification: When I choose those 10, I'll also choose where they'll be placed and what their respective humiliations will be, hehehe.

#wedgietober2026
September 15, 2026 at 6:27 PM