I just gave this a go and loved it.I got 25 mins and about halfway through my nipples went numb and the pain easied off but once I pulled free they really hurt. Great fun, good dare.

This one sounds pretty good, I may well try it later.

Needs some dares for speedos
 

I got these speedo some how and i thought that i might as well have some fun in them give me some ideas to do with or wearing them

Make them embarrassing

Take in mind nothing illegal

I've come up with a modification to this one, hope the OP doesn't mind me putting it here.

The problem I found last night is once you've pulled one hand free you can remove the rest of the pegs more easily, rather than having to pull them. So, the modification is as follows:

Tie the keys to a padlock (or handcuffs) to the head of the bed, and also attach a rope to the head. Then scoot down so you can't reach the keys. The rope should be long enough that youcan still reach the end of it. Then attach the clothes pegs and tie them to the foot of the bed. The number can be decided by a dice roll (or two or three if you're feeling brave). Then padlock your wrists to the rope. Now you shouldn't be able to reach either the pegs or the keys with your hands. You have to move up the bed to get the keys, which will pull the pegs off. How long you have to wait can also be decided by a dice roll. For some added drama, wait till you're desperate for the loo.

Excellent self bondage dare RachelJones thanks for the idea. I did modify it a lil bit though, instead of using cloth pegs i used those chineese nipple clamps so it was alot more difficult to handle. my nipples are raw right now and my gooch is killing me.

Thanks again!

I tried this and since there were 6 dots i had it for half an hour i loved the pain it had
really amazing dare

Ooh
 

This seems fun, i am not sure if i understand all of it but i get the idea and might try this out sometime ^^ Thank you for posting

I am definately going to try this out, it seems like so much fun!

Wow I did this last nigth when i had an empty house! Its amazing! Thanks hun. I wore stockings and did as you did and used a vibe too.Really intensifies it.

I wanna try it again but gagged this time. Great dare!

I just finished and it didnt hurt so bad:)

I got a 4 so 20 minutes it seemed like ages waiting for the alarm to go off. Gave me a big turn on and when the time finished i made sure I pulled of the pegs from my ball sac first so I could not cheat and so got maximum pain. Great dare

This sounds great! I'm gonna have to try this sometime. Might try it with a couple full zippers of clotheslines.

Thats an amazing dare. My master made me do it a little while ago. I had to do it for 25 minutes. My master knows I can't keep still so the pegs kept on pulling! Ouchies. I would definitly do this dare again....hopefully my master will let me.
I love pain dares.

Decided I'd try something new and give a pain dare ago. Waiting for parents to go to bed and will then make a start!

This sounds really awesome - will definately do this in the near future. Hopefully the roommate will get out of here sometime... :p