Long Anal Punishment for Skipping Work
 

This dare lasts for a while, but if you have a job, you should have the mental stamina required to complete it.

If you have a chastity device put it on. This isn't about your dick's pleasure and I'm not going to risk a regular orgasm ruining your work ethic.
If you have a prostate orgasm, you should be able to continue without any loss of drive, so you can have as many as you like.
You know what they say: Do something you love and you won't work a day in your life

Prep:

Get out all your anal toys and arrange them from smallest to largest.
Count the number of hours you're usually at work, and keep out that many of the largest toys you have (for example, with a 7 hour work day, you would use the largest 7 and put the rest away). Play porn involving anal throughout this task (straight or gay, it doesn't matter. Preferably long compilations though so you're not distracted by constantly changing the video). Now, you're going to work your ass the same amount you would be working your job.

Work Begins:

Start with the smallest toy and loosen yourself up with lube for 10 minutes. Now, add toothpaste as lube and continue. At the half hour mark, reapply the lube, then the toothpaste. Switch to a different postion (if you've been pumping, switch to riding to give your wrist a rest or vice versa) and continue. After an hour, switch to the next, slightly larger toy and repeat the same process. Keep doing this until your 'work day' is over.
(if you don't have enough toys, keep reusing the largest one once you reach it)

As a recap, each hour is:

• 10 mins of warming up with a new toy and regular lube

• 20 minutes of anal with toothpaste added

• More lube and toothpaste before 30 minutes more anal

You may take breaks at the same times you would while doing your job, and I'd recommend taking an enema during them.
If you want to be sure you won't miss a cue, set alarms in advance.
You don't have to constantly fuck your ass, as long as the toy stays inside and you're playing with it somehow