Chasity Sentence Challenge List Needed

[JPEGking]

Hi all,
I've come to you all for some help. I recently gave the keys for my chastity cage to a local college student who was interested in keyholding for me after much discussion. We settled on an agreement of terms for release, part of that release agreement is that I will have to earn points to get released. I will earn points by completing challenges from lists. The lists will be separated by Easy, Moderate, and Hard difficulties. Each challenge will be given a number according to each list. Each week, she will put the number of challenges for each list into a random number generator and then those will be the challenges available for me to complete for points each week.

Anyhow, here's what I need help with. I've got a few challenges already, fairly standard ones that you might expect, but I need more. I've seen what the good folks here at GetDare can come up with and how creatively simple or simply challenging the dares, challenges, etc can get. Any challenge is acceptable to suggest. I will nix or modify if needed. I look forward to seeing what all you masterminds of dares and challenges come up with. Thank you!

[JPEGking]

This thread will remain open for the duration of my being in this chastity sentence, so there is no time limit other than that for it.

[esmond]

Some challanges:

1) Go outdoors, strip, take photo proof (no face) put on 6h with 5 minutes extensions. Post link

2) Go outdoors, to the place of your choice. Bring blindfold (a cap drawn below your eyes is fine), nipple clamps, phone and earphones. Undress completely naked. Put the earphones in your ears. Put the volume high. Attach nipple clamps. Start this song https://www.youtube.com/watch?v=1TzYnfcxNNE , put on your blindfold and wait for the song to finish

3) Put in your medium plug. Put a pair of clothepins on your nipples. Go to a supermarket and find a cucumber you think will be a challenge, but fitting in your ass . By it together with a packet of condoms. With other items if you want to look less like a pervert. Go home remove your clothepins and your plug and start fucking yourself with the cucumber

[JPEGking]

Originally Posted by esmond

Some challanges:

1) Go outdoors, strip, take photo proof (no face) put on 6h with 5 minutes extensions. Post link

2) Go outdoors, to the place of your choice. Bring blindfold (a cap drawn below your eyes is fine), nipple clamps, phone and earphones. Undress completely naked. Put the earphones in your ears. Put the volume high. Attach nipple clamps. Start this song https://www.youtube.com/watch?v=1TzYnfcxNNE , put on your blindfold and wait for the song to finish

3) Put in your medium plug. Put a pair of clothepins on your nipples. Go to a supermarket and find a cucumber you think will be a challenge, but fitting in your ass . By it together with a packet of condoms. With other items if you want to look less like a pervert. Go home remove your clothepins and your plug and start fucking yourself with the cucumber

I love all of these, screenshot them and have sent them off to my keyholder. Thank you again!