Sorry for delay, I had an injured eye. Yes there is a key holder event that starts when you start sex with the slave that is the key holder. I found that the only way to assign a key holder was to do so during the game setup for the starting slave. If that did not work, then you likely have an installation problem.
The CB mod is an older mod and does not use the newer mod system features. This means that although the mod system can successfully apply the mod regardless of its path, the mod cannot run correctly unless it has a very specific path. The mod must have a path that matches ".../STRIVE_MOD_FOLDER/Es-02-ChastityBelt/info.txt", by default this would be ".../Strive/mods/Es-02-ChastityBelt/info.txt". If the mod is extracted into an additional folder, then it will not work. When the folders are fixed the game should work as intended; however, it may have corrupted some data in your save file, so you may need to start a new progress.
Also note that the CB mod conflicts with mods like the Bugfix mod, which re-arranges the code for starting sex.
Viewing post in Chastity Belt Mod v1.2.2 (for Strive v0.5.25)
Your mod folders may look something like this:
- Strive
- Mods
- ExpandedSex+ChastityBelt-v1.3e
- Es-01-ExpandedSex
- Es-02-ChastityBelt
- ExpandedSex+ChastityBelt-v1.3e
- Mods
The folders need to look like this:
- Strive
- Mods
- Es-01-ExpandedSex
- Es-02-ChastityBelt
- Mods
Select and apply only those two mods, and restart the game.
Start a new progress, select Customized Start, and select Keyholder as your relation with your starting slave.