Sleeping Dare/Task

[naked_lego]

If you absolutely can't accomplish one of the requirements then reroll. If it is against your limits then reroll. If it isn't one of those then you might as well try it. Even if it isn't one of your likes. You can always try the dare the next night.
Dare potentially Involves:
Clothing Control/Nudity, anal insertion/stimulation, vaginal insertion/stimulation, sex toys (a variety for full dare), humping, bondage, edging, and an erotic playlist**.

Will you be sleeping on a bed with covers?
This roll is optional!!
(I never liked the part about sleeping on the floor or without covers. I know it is supposed to make it more difficult/daring/controlling but it is just uncomfortable. It's also the middle of winter right now and I want both a bed, pillow and my electric blanket.)
Heads/Evens - Yes
Tails/Odds - No

If 'No' then roll:
1: On your bed with only one other item
2: Not on your bed with all of your items
3: On your bed with as many pillows as possible
4: Not on your bed and only use blankets
5: On you bed and only blankets
6: Not on your bed with only pillows

What will you wear to bed? (Crossdressing or Clothing Control/Nudity)
This roll is optional!!
(I normally like being naked when doing a sleeping dare which is why is it optional but you may decide if you want to roll or not.)
1: Regular sleepwear
2: Opposite sexs' underwear
3: Nothing
4: Regular sleepwear
5: Nothing
6: Someone else's underwear

What will will be your difficulty?
Roll a 6 sided die to decide what will be your difficulty or you can roll once for every section.
1-2: Accessory
3-4: The Restriction
5-6: To Do List

Accessory (Sex Toy, Anal insertion & optional vaginal insertion)
(Attention ladies!! If you want to make it a little bit harder then you can roll again for a vaginal insertion.)
1: Insert your smallest sex toy anally
2: Insert your largest sex toy anally (within reason)
3: Insert your longest sex toy anally (within reason)
4: Insert your favorite sex toy anally.
5: Set your vibrator on low so that is it stimulating your crotch, then roll for another
6: Set your vibrator on low so it is stimulating you anally

The Restrictions (bondage)
(I would be willing draw up a diagram at your request. Since I realized I might not have been able to explain it very well. You can use anything you want/have. I personally use shoe string. Other things could be: hand cuffs, rope, string, maybe tape)
1: Bind your wrists together. Probably easier with handcuffs but I have done it with a shoelace
2: Bind your hand to your genitals*
3: Bind your writs together between your legs. Up to 1 foot of slack between them. Probably easier with handcuffs but I have done it with a shoelace
4: Bind your wrists and feet together. With up to 2 feet of slack between them
5: Bind your legs so they are spread apart
6: So both #5 and #2

To Do List (Pre-Sleeping Task)
(This section could get a little tricky and may involve setting something up before sleeping.)
1: Edge 2 times
2: For 5 minutes be on your knees, legs spread and blindfolded on the floor
3: Put on a playlist that will play for a hour or of something erotic for you to listen to while you fall asleep**
4: Run your hands all over your body for 2 minutes. Explore every crevasse.
5: Do #1 and #3
6: Do #1 thru #4

Now, gather everything you need to get started. Clothe yourself how you are required. Insert what needs to be inserted. Get into your bed for the night and turn on what should be on. Enjoy!
Feedback, requests, and advice posted as a comment will help to make a version 2.0. Requests can be taken under consideration to rewrite this dare. I hope to see stories posted somewhere. If you give me the link I would love to read them!

*I managed to tie my hand around my penis with shoe string. what I did was tie it around my penis and balls to have one end tied down. Then grabbed my hard penis and wrapped the string around both. It was tight enough that I was able loop the end around one of the wrap around. I'm not really sure what to do for you girls but maybe make a crotch rope, or use tape instead. Maybe bind your hands together between your legs

**I used my smartphone and made a playlist on Sound Cloud of erotic material. You can use headphones, I don't like them so I just put my phone under my pillow and turned it to a decent volume. You can also change the volume a bit depending on the direction your speaker is facing. With my on the charger and under my pillow, it did get extra hot so proceed with caution.

Here is the original dice dare that inspired me.

[Pett.I.Grew]

I am going to have to sleep naked with my hands bound to my genitals.

[Pett.I.Grew]

Originally Posted by Pett.I.Grew

I am going to have to sleep naked with my hands bound to my genitals.

The hardest part (other than my penis) was that I move a lot in my sleep, so I kept waking up in pain to my hands yanking my genitals. As a result, I got very little sleep and my balls are sore.

[naked_lego]

Originally Posted by Pett.I.Grew

The hardest part (other than my penis) was that I move a lot in my sleep, so I kept waking up in pain to my hands yanking my genitals. As a result, I got very little sleep and my balls are sore.

Thanks for doing the dare ^^