My First Attempt at a Wedgie Dice Dare

[undyguy79]

It is an interactive wedgie story in which at certain points indicated by *(Roll dice):* you will roll 1-2 6-sided die to determine what happens. You only get a free reroll if you actually do not have the object in the corresponding number dare. If you reroll for any other reason or have to reroll 2x because you do not have the object required, you have to go to “punishment” at the end.


You have had a busy day at school/university and are just getting ready to change in the change room to go home. Just as you are lowering your pants, your bully struts in! Oh no! Today you were wearing (roll dice):

Spoiler:

(1) White briefs
(2) Man thong
(3) Colourful bikini-style briefs
(4) White briefs that are at least 2 sizes too large
(5) Women’s panties
(6) Boxerbriefs
(7) Cartoon briefs
(8) Colourful basic briefs
(9) A visibly dirty pair of underwear (sweat stains, pee stains, jizz marks, etc.…)
(10) Speedo or another swim bottom (spandex)
(11) White briefs hidden under boxers/boxerbriefs
(12) Briefs you accidentally put on backwards

Your bully instantly spots you vulnerable in your underpants, blocks the door with a chair so you cannot be interrupted and heads straight at you. Unfortunately, your pants were still around your ankles, so you are unable to flee from them! They tackle you down to the ground and mockingly say “looks like it is time for a… (roll dice and give yourself the wedgie indicated):

Spoiler:

(1) Regular wedgie
(2) Frontal wedgie
(3) Jocklock wedgie
(4) Squeaky clean wedgie (ouchie!)
(5) Front and back wedgie (all-around)
(6) Chair wedgie

It feels like forever as the underwear is yanked mercilessly by your bully – but actually it was only (roll dice):

Spoiler:

(1) 5min
(2) 30sec
(3) 1min
(4) 2min
(5) 6min
(6) 4min

You hope that this is all for now, but he pulls your pants off, takes out your belt and tightens it around your legs so you are unable to run away (tighten belt or use other object to tie your legs together). He then strolls over to his locker and pulls out a menacing looking bag. You are squirming with your underpants still left the way it was after he was yanking on it. He says: time for a more creative wedgie, pulling your underpants back to their normal position (you can pick previous wedgie now) (roll dice):

Spoiler:

(1) He slips a jockstrap over the underpants that you are wearing, then jocklocks you twisting the legstraps at least 2x around each ankle. Then he grabs the back of the briefs under the jockstrap and gives a wedgie as high as those underpants can go!
(2) He takes a hockey stick (or other long pole-like object) that can support your weight, loops the back of your underpants through them then places 2 chairs on either side. The stick rests on the seats of the chair and you are in the middle. He then forces you to sit down until your butt can reach the ground as your underpants hang over the stick.
(3) He pulls out a rope (or similar object) and loops it through the back legholes, over your shoulders and then each end through the front legholes. He pulls up on the loose ends on the front until your underpants are as high as they go and then ties off the front 2 ends. He then takes a sweaty pair of his undies.
(4) He uses the hockey stick on you (as in (2)) but puts it through the front of your underpants! Still forcing you to sit so your butt touches the ground
(5) He wedgies up the side of your underwear and then pulls one arm through each leghole so that your underpants sides rest in your elbow bend.
(6) He sticks a white pair of briefs on backwards over the pair you are wearing. He wedgies your undies up the back as high as they will go and then the white pair over top up the front as high as they will go.

This is torcher! Again, feels like I’ve been enduring this forever, but apparently it only lasted (roll dice):

Spoiler:

(1) 5min
(2) 20min
(3) 15min
(4) 10min
(5) 8min
(6) 22min!

He then tells me he’s gotten special objects to enhance my wedgie!!! I look very worried as this is torment! I beg, but he does not listen. First, he offers to change up the wedgie for me (roll dice):

Spoiler:

(1-3) Stay in the same wedgie
(4-6) Roll again from second list of wedgies and perform that wedgie

“Now that you’re comfortable” he mocks “time for some additional fun!” (Roll dice):

Spoiler:

(1) He takes a sweaty or pissy pair of his undies and sticks it over my face so the smelliest part is next to my nose
(2) He takes a butt plug, picks out my wedgie, inserts the butt plug with lube and then puts me back in the wedgie
(3) He takes out a sweaty pair of undies or socks, sticks it in my mouth and then gags me with a ball gag (or similar object)
(4) He sticks a cock-ring or ball stretcher around the base of my balls (reroll if you don’t have an object)
(5) He gives me a swirly while I am in the wedgie
(6) He spanks my exposed butt 20x per cheek while I am in the wedgie

He finally releases me from my wedgie torment and even pulls off my stretched out pair of undies, leaving me naked and removes all objects from above. “Oh we’re not done yet,” he sneers, dashing the hopeful look on your face, “I have one more special wedgie planned for you! Things are about to get messy!” (Roll dice, make sure to have selections from both lists before doing wedgie):

Spoiler:

(1) Puts you in clean white briefs and plans to give you a squeaky-clean wedgie
(2) Puts you in briefs at least 2 sizes too large for you and plans to atomic wedgie you
(3) Puts you in dirty white briefs and plans to give you a normal wedgie
(4) Puts you in colourful/cartoon briefs and plans to give you an all-around wedgie in them
(5) Puts you in white briefs backwards and plans to give you a frontal wedgie in them (the back of the briefs go over your crotch and you will Melvin them)
(6) Puts you in bikini-sytle briefs or speedo and plans to squeaky clean you in them

But first, we must know what I am going to add to your underwear! (roll dice):

Spoiler:

(1) Phew – he pulls out a can of shaving cream and sprays it down both the front and back of your underwear
(2) He has a mixture that looks like diarrhoea! He spoons it into the back of your underwear (options include peanut butter/chocolate or banana/chocolate that you can warm in microwave for 10-20s – do not burn yourself but should be warm like poo)
(3) He takes toothpaste/icy hot/warming lube and squirts it down the front of your underwear and then inserts a butt plug into you!
(4) He forces you to piss the underpants that you are wearing!
(5) He takes 2 small cups of ice and dumps one down the back and the other down the front of your underpants!
(6) He takes some mayonnaise (or some other semen-like material) and dumps a good load down the front of your underpants!

“OK – now that you’re ready – it’s wedgie time!” and he gives you the wedgie he was planning for a good 5min straight. You can feel the goopy/wet stuff in your underpants and uh oh! For some reason it is getting you hard! Of course your bully notices! (roll dice):

Spoiler:

(1) He makes you grind your crotch against the ground in the wedgie until you jizz your undies
(2) He grabs the front of your underwear and jerks up and down on the waistband so the crotch panel rubs against your hard-on causing you to jizz
(3) He makes you reach down and rub yourself off while he continues to wedgie you
(4) He does not let you jerk-off, but instead spanks each butt cheek 50x for getting a boner
(5) He makes you edge 3 times (must go soft between) before finally allowing you to jizz in your wedgied undies.
(6) He strips you naked, takes your messy undies and places them over your head and then lets you stand in the middle of the room and jerk yourself off while he watches

If everything went as the bully planned, then you are lucky and he finally leaves you in peace! However, if something did not go right (you needed to reroll or could not complete the wedgie) he is annoyed and has a little something extra planned for you!! (Roll dice):

Spoiler:

(1) He takes a big piss in the toilet, puts you in the most embarrassing pair of underwear you own (in this order – you can only go to the next on the list if you do not own the preceding underwear type – panties --> white briefs at least 2x larger than your normal size --> dirty pair of briefs --> man thong --> cartoon briefs --> normal pair of white briefs --> normal pair of briefs). He then swirlies you in the pissy toilet water while he wedgies you!
(2) He sticks you in 2 pairs of briefs, makes you drink a beverage with caffeine & 2 glasses of water & makes you piss yourself. He then takes the top pair of briefs, sticks it over your head making sure that you suck on the material and wedgies the pair you are still wearing all-around (front and back simultaneously)
(3) He sticks a buttplug in you, gives you another hockey stick wedgie, dumps lube down the front of your briefs and makes you jerk off again. This time he also makes you taste your jizz before he lets you out of the wedgie.
(4) He gives you a permanent wedgie in (panties --> man thong --> dirty briefs --> too large briefs --> cartoon briefs --> white briefs --> any briefs) and makes you wear it the rest of the day without picking. You can take it out before bed, but have to jerk off in the undies and sleep in them
(5) He puts an old pair of undies on you and wedgies you until they rip off. Then he takes a pair of briefs, sticks icy hot/toothpaste in the bottom of the briefs (the part that covers the taint) and gives you 50 squeaky clean pulls (front-then back = 1 pull)
(6) He makes you drink liquids as in (2) and then dresses you up over an embarrassing pair of undies and wedgies you until you piss the clothes you are wearing. After you have peed, he leaves you in a wedgie in the corner for another 10min

[ToiletBoi]

This is great good job do you wanna roll for me before I do it undyguy since you know best about it

[undyguy79]

Undies type - 11
First wedgie - 5
Duration - 4
Second wedgie - 1
Duration - 2
New wedgie - 6
Additional action - 5
Final wedgie type - 2
Messy material - 1
Grand finale - 5

If you're bad for any reason - 4

[Angelica.156]

Would someone roll this for me?

[aelae]

wow that sounds intense

[Brattylola]

Commenting so i can see this later


Bur sounds fun and harsh