With all due respect I think you're a bit crazy to attempt any sort of lengthy ride while sporting a device. Especially one with a rigid base ring. The opportunity to come down hard on the seat or another part of the bike and seriously injure your perineum is just too great. And if that happens you'll likely not even need a CB to remain chaste.
So, then the choice is to give up one practice or the other.
This is a issue I struggle with quite a bit. I ride around 100 miles a week and typically my rides are long enough that I wouldn't even attempt to wear a CB, so I don't. And often when I come home my KH is gone which means I'm unsupervised in the shower. This happens 3 or 4 times a week. Less than a perfect scenario for a denial junkie.
Here's how I play it mentally. The bike is sacred ground and my KH can't deny me access. However, I can't use the bike to to cheat her out of her hard work keeping me chaste. So, just before I walk out the door I use the spare key which hangs on a hook underneath my helmet by the door. I put the helmet on my head, unlock my junk and then ride. Once back home I collect my CB on the way to the shower where I clean up and then lock back up immediately.
There are side benefits to this practice. Even during the quiet weeks where I only ride a couple of times I'm out enough that my KH is spared the hassle of freeing me for maintenance issues. I have incentive to stack up my rides on consecutive days so I can spend the first part of the week locked up 3 or 4 days straight. And being freed and then put back in without so much as a tease often ramps up the feeling of denial. Just what I'm looking for.
Certainly it's less than perfect, but no arrangement is. And like many things in life it's a compromise. But I don't want to go without either one.