Are you sadistic enough?
 

First strip naked and get your cock nice and hard. You will then wrap 5 rubber bands around your cock and balls. You will then snap each rubber band one at a time until you cannot take any more. (you must do at least 2 rounds) You will then remove the rubber bands.

Then lets do some foot torture. Give yourself a very hard bastinado. Get a cane or thick stick and give each sole a very hard 50 strokes. Then you will fill a pair of your socks with popcorn kernals or pebbles. you will then do some exercises. You will do 50 jumping jacks and run in place for 10 minutes. Finally you will squat over your largest dildo and ride it for 10 minutes. No stopping. If you stop, the time stops and you earn another 20 cane strokes to your bare soles for each time. You will do the punishment cane strokes when your time is up.

When done, send me a very detailed report. If this was not enough to make you cry, then I will send you some more.

Ill get you a report as soon as I can finish it <3~ and I might ask for more even if crying XD

I lost count of the number of rubber band snaps, so they were bound for a while and were aching pretty bad by the time I finished em. Got a few bruise to <3

I used my favorite cane for the bastinado, it's not often people take me up on this kink. 50 swats each had me howling though, I was hitting particularly hard. Kinda got carried away since it had been a while.

Needless to say they already hurt like fuck when I started exercising, every jump almost made me fall to my knees. But I was able to finish em and get onto my treadmill. I wasn't able to run nearly at the speed I'm used to, was more like a hobble/limp. And yes you got my eyes watering before I finished my jumping Jack's <3

I was able to ride "Stan" with out stopping though it was tempting, my gluttony for punishment was hard to resist ~

Thank you so much got the task, I really hope I hear from you again.

Bumping for more tears ~

I see you are looking for more torture. So lets have you do this.
First you will coat your largest butt plug with icy hot and insert it into your ass and leave it there for 1 hour. During that time, you will spend that time beating your balls and your ass. You will start by giving your ass a very hard caning. I am thinking 150 strokes is good for you. Then you will go to a table and you will tie your cock and balls so that they are secure and you cannot move them. You will then take your rubber mallet and hit your cock and balls 150 times. Repeat the ass spanking and the ball beating until the hour is up. If you are screaming to much from the beating, take a piss soaked sock and gag yourself to keep yourself quiet.

This is simple but will have me howling. Thanks again for the task

And im always looking for more :D

The bruising and swelling in my nuts is finally fadded, but fuck it felt amazing while it lasted. Would happily do this one again ~

Tie a rope from your balls to your big toe. (it should be kinda tight at full extension, so it kinda pulls of your balls with each step) then go for a walk (minimum 100 yards) when you get back, edge 5 times, and repeat. no cumming aloud.

the second time you get back, edge only 4 times, then repeat the walk.
the third time returning, edge 3 times, repeat, 4th time, edge twice, repeat, and finally on the 5th time returning, edge once, do the walk one more time, and then come home and now you may cum, but only if you do it onto your face, with your mouth open.

(oh damn this dare was fire! im gonna make a thread out of it!)

Sounds like a good morning walk, hopefully there is something for me to do when I get home <3

Also im gonna choose not to cum since I have cumming in my limits

Here is one challenge I like to give to my slaves sometimes. First, tightly tie up your balls and sit on a plug that is not really comfortable for you. Second, prepare some piss in a bottle or glass.

Take a wooden spoon or similar object and slap your balls with it. You will do the following procedure first only with the right one, and always hit the same spot, and afterwards again with the left one:
You have to hit each ball 20 times. The first hit should give you some pain, but not too much. But then each hit has to be considerably harder than the previous one. Since I am not there to control you, reconsider after each hit if you really made it harder than the previous one. If not, start again.

When you did this with both balls, repeat it with both balls at once while your mouth is filled with your piss. You may not swallow or spit out any of the piss during the procedure, or you have to redo it. Tell me how it went!

40 hours to each made them sting but was a but mild in comparison to my other tasks, still, thanks for the abuse

Day of fun:

Start by making an enema with warm milk - hold it for 30 minutes. Meanwhile hit each sole of your feet with a metal coathanger - give me the count.

When time is up empty yourself into a bowl. Use it to make oatmeal - this is to be eaten now.

When finished eating treat your feet with some more bastinado - same count as reached before.

Get a well sized dildo - preferably a double dong and deepthroat yourself and use it to empty your stomache into the bowl.

When stomache is empty go get a q-tip and make that almost disappear into your urethra. Edge once like this.

Remove q-tip and get a sliver of ghostpepper or like; make that disappear fully into your uretha. Edge again.

Eat contents of bowl. When finished you can get the sliver out and rinse with milk.

Tie up your balls, not too firm though. Go to a door and place your balls between the door and the door frame near the hinges. Slam the door on your nuts until you pass out. Give me the count.

Report back - and answer me, if you want more? ;-)

Milk always makes me cramp when I use it for this long, and I know how Vile you like things so I made sure to wait till first thing in the morning to do this.
I ended up hitting each sole 1376 times each with the coat hanger and they ached like hell by the end of the 30 minutes
Needless to say after the second set of Bastinado I will be crawling around for a while.

Always dread it when you make me eat something cause I know it wont stay in my stomach long. Not only is it hard to keep down the first time, but after all that work I have to puke it back up. Throat is going to be sore for a while but shouldn't be to bad.

The qtip edge, just dried up and roughened up the inside of my cock for the Ghost pepper (hate that you know I keep these in the house some days). Edging with the pepper in made me howl in cry to say the least. even after rinsing with the milk it burnt like fuck. Some of the juices leaked in farther then I expected :/

Its so hard to get puked up shit past your nose let alone my gag reflex. . . took a while to empty it but I managed to. Was sobbing the whole while till I was able to try and rinse my cock out.

And do to safety reasons, since I don't have anyone here I don't let myself pass out from tasks if I can avoid it anymore. Still it only took 2431 for me to get super light headed in dizzy.

Thanks again for the dreadful and horrid task Sir.

I ALWAYS WANT MORE >:3

It's so hot reading these punishments, and the reports. These are slightly harsher than I can take, but I would so like to be given challenge after challenge like this. Good job, everyone, and thanks for sharing!