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Old 09-16-2018, 02:27 AM   #1
Hollipop
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Pencil Ultimate Roleplay School day dice dare. Spanking, wedgies and more!

Welcome! This was inspired by Serrated and the dude's original dare. Shout out and props!

Ultimate School Themed
~ Challenge ~
Est. 3 hours.
This was written for girls but you can easily change things to accommodate dudes.

●So, You only need one dice��, which you can find at https://www.random.org/dice/
Also keep track of your tally score. The dare will take a while but it is packed with naughty fun.

�� Teacher:Top/Punisher/Dom/Spanker
��Student: bottom/punishee/sub/spankee

●You’ll need:
ruler ��
paddle��
dildo��
buttplug��
toothpaste/icy hot/vics❄��
clean sock or dirty undearwear�� nipple clamps��
Your Top/Dom��
Cuffs or ropes��
Lube (optional but recommended for safe play)��
Vibrator

This is a role play dice dare.
★Rules. (Break or don't break. Have fun)
➡️No ass rubbing, rub =��1 tally
➡️No open defiance or disobedience, defiance =�� 2 tally
➡️No pouting or sulking, ��2 tally
➡️No backtalk ��2 tally
➡️No swearing, potty mouths get mouthsoapings and ��1 tally
➡️3 late rolls= ��1 tally
➡️ No disrespect, disrespect =��3 tally

●Start off by cuddling your top and watching one spanking school girl porn video together. Exciting, yes?

●Now, for fun, decide your persona.
✔️*Obedient and sorry. Any 4 steps done complete will be considered passable and without a hitch.
Challenge intensity: lenient

❌*Bratty and defiant. Get automatic ��2 tally at the start of game plus! any 4 steps done must show uptmost remorse or a do-over may be done after attitude junction.
This is under the discretion of your Top/Dom.

Challenge intensity: Strict

((Attitude junction is a spanking that reaches sniffles.
Do over means to do 4 steps all over again after finishing it the 1st time.))

Do four steps.
Step 1. Say you are a naughty girl
Step 2. State why you are naughty and why what you did was naughty.
Step 3. Ask to be punished to remember to behave next time. Raise skirt or bare your bottom. Be helpful to the punisher.
Step 4. Receive punishment and thank punisher with the right attitude.

●Warm up time! Have that ass spanked for 5 mins straight starting with light pats and building intensity. Not too hard. Save that ass for serious punishment later.

●Ready? LET'S PLAY!!!

�� A.
Good morning!
You wake up to a sound of your alarm clock, you look over to shut the dang thing off when suddenly, realize you’re running late for school! Shit! You jump up and get dressed quickly and you...

1⃣. Wear only underwear and socks
2⃣. Wear skirt and shirt no underwear
3⃣. Wear whole school outfit
4⃣. Wear whatever your Top pleases
5⃣. Wear school clothes without bra
6⃣. Wear nothing!


��B.
You hurry up and get out of the house to go to school. When you finally arrive..

1⃣. You're late! Uh oh.
‼️5 slaps on each hand with the ruler
[��1 tally]
2⃣. Just on time. Lucky! Move along.
[If showed up naked�� 1 tally]
3⃣. You're late but only your classmates noticed. They think you're cool so you feel like being reckless. Let's see how cocky you are after you suffer.
‼️Draw the alphabet on your clit. Do not cum.
If you cum, reroll for this round.
4⃣. A little late. Time to teach you a quick lesson.
‼️3 spanks on your Pussy and 3 on your asshole
[��1 Tally]
5⃣. Somehow, you arrived early!
✋ Wait 1 minute before continuing.
6⃣. You’re very late! No excuses! ‼️ spank ass with a ruler 15 times (Over underwear unless you’re naked)
[��1 tally]


��C.
You go to your first and favorite class, Surf Education. What will you do in class today?

1⃣. Be reckless and unlucky. Get caught for watching porn.
You liking that huh? Not for long.
‼️ Watch porn for 5 minutes.
As for your punishment, you have to present yourself with your underwear off to the class. They can tease you for 5 mins. Roll the die for position.
1-3 lying on the bed, legs spread (hands spreading pussy lips wide if girl)
4-6 Bending over, hands spreading ass cheeks aparts
[��2 tally]
2⃣. ✋ Just chillax for 1 minute.
3⃣. The teacher gets mad at you for talking. Hopefully some corner time shuts you up.
‼️ Go stand in the corner with a sock in your mouth for 5 minutes. [��1 tally]
4⃣. Frustrated Artist. You try to slack in class and a bully picks on you. Bummer.
‼️ Draw a naughty picture.
Be given a wedgie and handed to the teacher who twists your nipples. No picking out wedgie.
If no underwear in the beginning wear a pair.
[��1 tally]
5⃣. Be productive and remind yourself the importance of doing your work.
‼️3 hard spanks with a ruler per palm and then write "I will not procrastinate." 20 times.
6⃣. You'll regret loving kink, you idiot. You're caught with porn by the teacher! You are punished and displayed. Show everyone what a naughty girl looks like.
‼️ Edge 3 times to kinky porn.
Over the knee spanking with paddle 30 times (Bare bottom) then stand in the corner with your underwear down for 5 minutes to display your ass.
[��3 tally]


��D.
Next class! Math, eww. You trudge reluctantly along and in this class you will...

1⃣. Studious!
‼️ Sit down and do 1 math related problem for 3 minutes. Personally, this is the worst outcome in this round. Just saying...
[If you have tallies, remove one��]
2⃣. Goof around and get caught. Facepalm. Pray for mercy.
‼️ Diaper position 10 spanks alternating sit spots.
�� Tops choice of implement. ��
[��1 tally]
3⃣. You think math is boring and you skip class and get away with it! You're lucky for now but your luck will end soon. Trust me.
4⃣. You think math is boring, try to skip and get caught doing it. I think you like getting caught!
‼️You are dragged by the ear to the corner.
Bend over, hands on the wall. spank 20 times with paddle
[��2 tally]
5⃣. You mess around in class and end up in the corner. You're gonna wish you just sat down and behave. Try not to enjoy being punished too much.
‼️ 5 minutes, your hands above your head.
If you move even a little, you get 10 spanks to your pussy after the time is up.
[��1 tally, if very wet ��+1 more]
6⃣. The teacher gives you a test and you fail it miserably, Naughty naughty. Should have studied!
‼️Do a 4 step ♦️

Do four steps.
Step 1. Say you are a naughty girl
Step 2. State why you are naughty and why what you did was naughty.
Step 3. Ask to be punished to remember to behave next time. Raise skirt or bare your bottom. Be helpful to the punisher.
Step 4. Receive punishment and thank punisher with the right attitude.

Bend over furniture, spank ass 30 times with paddle.
�� Spankers choice for position�� boobs 5 times each with the ruler [��2 tally]

➡️Pick any wedgie out after this round.


��E.
History time! This class is interesting, what pray tell, happens now?

1⃣. You’re in class and the teacher discusses the history of schooling and you volunteer to show how students used to get punished. A glutton, are you?
‼️ spank 25 times with a paddle over furniture saying "thank you, please spank me harder" after each spank.
then kneel in the corner for 5 minutes with your hands behind your head. No moving!
[If you move, add ��2 tally, if not, remove 1 tally��]
2⃣. Pretend to learn. No effect. Move along before I get nasty.
3⃣. You learn about torture methods used and you volunteer to be an example. Do you want to be punished this badly?!
‼️ Spank feet soles 30 times very hard fully naked.
[If you can’t complete it, add ��5 tally]
4⃣. You skip this class and get caught doing it. You seem to never learn.
‼️Get dragged by the ear and forced into diaper position
spank 25 times with a paddle
[��2 tally]
5⃣. You’re late to class! A tardy student is a student who needs to learn respect!
‼️ Stand in the corner for 5 minutes with your hands behind your back.
If you shift or move, have your Top lead your by your cock or fingers in your pussy around the room. 3 laps. [��2 tally]
6⃣. You learn about torture methods and you’re teacher decides to use you as example. Lucky you.
‼️ Do 4 steps ♦️ then get a Gag with a sock or underwear
��Top choice for gag��
Get fully naked and lie down with your legs spread, spread vagina lips wide and spank your pussy and clit 30 times with a paddle or ruler.
Forcefully be turned onto your stomach to endure 5 mins continuous spanking on ass, Thighs and sit spots.
[��2 tally]


��F.
Health class! Today is all about Sex Ed. You feel weirdly horny and your Teacher makes you feel all hot and bothered.

1⃣. The teacher uses you as a human model. Poking and teasing encouraged.
‼️ Do not move.
Top strips you fully naked and have you stand completely still in the center of a room, keep your legs wide apart and arms behind your head while your Top inspects every part of you for 3 mins.
2⃣. Your class talks about anal sex and you are the model. Huzzah!
‼️ Shove a plug your ass and leave it in there for 5 minutes.
Do 10 jumping jacks while you're at it.
3⃣. You skip this class and get caught doing it. Your days are numbered.
‼️ Get dragged by your nipples and pushed into diaper position
spank ass 20 times with a paddle and pussy 10 times with a ruler
[��1 tally]
4⃣. Your class talks about ejaculation.
‼️ Have a ruined orgasm.
If you make one noise, any noise, use a vibe to your clit until next round is over. No cumming.
[If you cum add ��7 tallies]
5⃣. The class discusses kinks! Your favorite!
‼️ Spank 50 times with a paddle in diaper position
Coat hand or fingers in toothpaste/ice hot and pet clit 30x no cumming.
Wear nipple clamps and kneel in the corner for 5 minutes with heavy books or objects in each hand.
If you move out of position, 5 sharp spanks to your pussy.
If you cum, edge 2x.
If you cum again. Roll again for this round
[��2 tally]
6⃣. Your late so the teacher makes an example of you!
‼️ Shove a dildo in your pussy and plug up your ass,
Doggie position spank ass 55 times with a paddle and remove dildo then spank pussy 10x with ruler,
Stand in the corner for 5 minutes, hands behind head.
Remove plug after
[��1 tally. If the dildo slides out, either add ��5 tally or have �� Top choose a number to do this round.��]


��G.
You head to science class but you see a group of people coming at you in the halls. BULLIES!

1⃣ - 2⃣: You’re able to avoid them and head to class. Lucky break.
[Remove 1 tally]
3⃣ - 6⃣: You're their little target, loser!
‼️ They strip you naked and you get spanked 70 with a hand.
You're made to wear panties and are pushed down to hang by your underwear. Dangle a moment.
You must then go to the next class with the big wedgie
[��1 tally]



��H.
Science time! I hope you aren’t sore..

1⃣. You skip this class and get caught doing it.
‼️ over the knee spank 20 times with a ruler and 20 with a paddle
[��1 tally and reroll this round]
2⃣. You’re late to class.. in fact very late. The teacher is very mad!
‼️ Diaper position spank 70 times with a paddle,
put nipple clamps and then
write “I will never be late to class again” 20 times hand written. Remove clamps after
[��4 tally]
3⃣. Do an experiment on humiliation.
‼️ lie down and spread your legs wide, clip your clit and let your Top tease, punish, spank, torture you for 3 mins.
[��1 tally]
4⃣. If you’re in a wedgie...
‼️ spank your inner thighs 20 times with a ruler, if you’re not, roll this round again.
5⃣. You skip this class, and manage to get away with it. Barely.
[��1 tally]
6⃣. How about an experiment ? ‼️ Rub icy hot or tooth paste on your pussy and tease yourself for 1 full minute.
Then Choose special A or B
�� Special A��
Roll the dice. If you get 3, you can skip Round I and proceed to J.

If you get 1,2,4,5,or 6, instead of Round J your Top can choose any Round and you will receive all punishments in that round.

��Special B��
Roll the dice, if it lands on 1,2,4,5, or 6 you will be given reprieve.
You have to cum 5 times in 5 mins. If you fail, you reroll Round B to J keeping all tallys you already have. You can still skip Round I.

If it lands on 3 you have to double tallys.

��I.
The teacher calls you after class. You've been trouble today. So you must repeat classes. After re rolls go ahead to Round J.

1⃣ repeat rounds D, F and H
2⃣ repeat rounds C,E and G
3⃣ repeat B,C D,E,F,G and H
4⃣ repeat 3 rounds Tops choice
5⃣ Try to seduce Teacher by giving oral, you do well but Top
decides to be evil. You are deemed to fail school and to suffer for it.
‼️Let Top play scold you for 2 mins, play with your nipples for 3 mins, spank you for 4 mins and
tease your aching pussy for 5 mins. [��4 tally]
6⃣ �� Tops choice if you reroll or skip but get ��5 tally.��

��J.
Well, the school day is over... Except, you've earned yourself detention!

Count all your tallies and then roll the dice
1⃣ - 3⃣: Double your tallies
4⃣ - 5⃣: Half your tallies (If it’s an odd number, round up)
6⃣: Keep the tallies the same
-----------------------------------------------------------------------
��If your�� tallies are:
0⃣: Congratulations, you have finished the dice dare!
‼️Play with yourself and you may cum if wanted.
Have more orgasms but only cum with permission after the first one.

1⃣- 2⃣: Not too bad, you get a warning,
‼️ 3 mins continuous spanks before you can cum.
��Position spanker's choice.��

3⃣-5⃣ Fair but still, you get detention tsk tsk:
‼️Do four steps.
1. Say you are a naughty girl/boy
2. State why you are naughty and why what you did was naughty.
3. Ask to be punished to remember to behave next time. Raise skirt or bare bottom. Be helpful to the punisher.
4. Receive punishment and thank punished.
Spanking on underwear. If not wearing, wear.
50 spanks to the ass, 40 spanks thighs, 30 pussy/balls, 20 to your foot soles.
Spend 10 minutes in just a wedgie in the corner with your hands behind your back.
You may cum after if wanted.

6⃣ - 8⃣: Mediocre but guess what? You're in big trouble regardless! Dentention:
‼️Do four steps.
Bare bottom spanking.
60 spanks to the ass, 50 thighs, 30 pussy/balls, 10 to the inner thighs, 30 to your foot soles.
Spend 15 minutes naked in the corner,
�� position decided your Top��. You may cum if wanted, but you must edge once first.

9⃣-1⃣0⃣ Oh my. Not that good of luck for you today. Detention:
‼️Do 4 steps. Bare bottom.
70 spanks to the ass, 50 thighs and sit spots, 30 pussy/balls, 30 to the inner thighs, 35 to your foot soles. Spend 15 minutes in corner, hands in air.
After corner time you may not cum unless you allow your Top to give you a thorough spanking of ass and thighs over the knee until s/he's satisfied.

1⃣1⃣+ Really? You should be ashamed yourself! I can see how horny you've become. You really must be taught a lesson. This is not acceptable!
Detention:
‼️Drag by the ear around the room once before endure a wedgie bounce and then
do 4 steps, spanking over wedgied ass and then �� fully bare when punisher wishes.��
100 spanks to the ass, 80 thighs and sit spots, 50 pussy/balls, 50 to inner thighs, 50 to foot soles.
Spend 15 minutes in the corner, hands in the air, nose touching the wall.
If you put down your arms, reset the time and add 1 minute each time.
In the second round, each movement is a minute of denial after the 1 hour.
You may not cum and you will not be cumming for 1 hour.
Every 20 minutes you will be doing a task.
☑️1st 20 mins watch 10 mins worth of porn with nipple clamps that will get you turned on.
☑️2nd 20 mins tease yourself and edge or ruin any orgasms within 10 mins. Rest for 10mins.
☑️Last 20 mins be tied up and teased by your Top until the 20 mins are done, only then can you ask permission to cum.
Cumming will be delayed more according to the 2nd round of corner times outcome.

��Lastly,
Aftercare. Cuddles, reassurances and first aid must be followed.

Report on how you did in the dare. I'm curious! I hope you enjoyed. Comment down below or send me a private message. Bump the thread if you want more people to try it out.

I hope you feel sore and punished. If it wasn't good enough, simply do another round from the start and send another report.

Stay safe, sane and consensual!
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Last edited by Hollipop; 09-16-2018 at 10:06 PM. Reason: Made it even better.
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Old 07-30-2019, 07:45 PM   #2
Lauren1199
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This sounds time consuming but really fun. I definitely want to try it.
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Likes: nipple torture, spankings (although can’t do them all the time bc of noise), wedgies, pain, teasing, bdsm, light anal

Limits: blood, urine, family, public, pics

Toys: nipple clamps, dildo, small butt plug, flogger

I don’t have a kik
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Old 08-23-2019, 01:54 PM   #3
somekinkyintrovert
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great couples or solo game
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Old 01-19-2020, 03:57 PM   #4
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This looks fun, I’d love to try it out.
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This bitch is owned, property of franklydogo

Punishment suggestions will be forwarded to my daddy and reported on if selected.
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Old 03-20-2020, 12:15 AM   #5
Patrickpmopen 1
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If anyone wants to see me do this or roll for me message me on kik it's in my signature
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Old 03-20-2020, 01:23 PM   #6
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I'll be doing this later tonight with this set
Strict rules set
A 6
B 3
C 4
D 3
E 6
F 3
G 1
H 3
I 1
D 1
F 3
G 5
J 1
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I am trapped in diapers almost 24/7 for an unspecified amount of time. Release of 3/1/23 at the earliest.

M/23/Straight

kik- Anonymos404

Sissy Name: Anna Naomi

Loves, Likes, Limits https://www.getdare.com/bbs/blog.php?b=93084

PM dare- https://www.getdare.com/bbs/blog.php?b=90880

Spoiler:
HMU on Kik and keep my sissy ass stretched or wedgie me till I'm begging you to let me go
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Old 09-25-2020, 03:40 AM   #7
Lesbian69
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This is really nice would love to do with my master
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I am bisexual please don't go on my username

Likes - Spanking, Wedgies, Humiliation, Writing on body, Degredation, Fingering

Dislikes - Fisting, Edging, Spanking the pussy, Corner Time, Writing lines
Limit - Pictures, Family, Pee or poop stuff, Blood, Illegal, Anal, Wax, Burning


I really want only those who are good at role-playing
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Old 10-01-2020, 12:47 AM   #8
YourEnemaLover6969
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I need to try this
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I❤️Enemas,anal play&suppositories&Forced laxatives.Will stick anything up my ass that’s my asshole can handle.

😍:enema,anal play.extreme pain&suppositories,forced laxatives&punishment enemas.

Want 2B given enema,wedgies,&anal dares. I❤️️experimenting with new things.ifu Like this stuff. Just shoot me a message and tell what I should try next.Message and let’s have a good time. I’m also a huge brat&No limits.
KIK/TeleGram-Yourdorkbabe.
SKYPE:Bubble.babe17
https://linktr.ee/Yourdorkbabe
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Old 10-14-2020, 11:54 PM   #9
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Thumbs up

i like!!!!!!!!!!!!!!!!!!!!!!!
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Old 11-12-2020, 10:32 PM   #10
YourEnemaLover6969
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I definitely need to try this but with a modified version. No toys
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I❤️Enemas,anal play&suppositories&Forced laxatives.Will stick anything up my ass that’s my asshole can handle.

😍:enema,anal play.extreme pain&suppositories,forced laxatives&punishment enemas.

Want 2B given enema,wedgies,&anal dares. I❤️️experimenting with new things.ifu Like this stuff. Just shoot me a message and tell what I should try next.Message and let’s have a good time. I’m also a huge brat&No limits.
KIK/TeleGram-Yourdorkbabe.
SKYPE:Bubble.babe17
https://linktr.ee/Yourdorkbabe
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