r/PeggingChastity

Look at how pathetic your cock is. It's squeezing out of your chastity cage. Begging to be punished. You're so desperate when you're locked in your cage. You're willing to do anything to please your Goddess. Are you willing to become a cock slut for me? Are you ready to become a good little cock slut for Mommy?

Subby has been such a good boy lately that Mommy releases him from his chastity cage and let's him cum. The only catch, however, is that he can only cum while I'm fucking his ass with my strap-on. This idea turns him on so much. When I release his cock from his cage, you can see how hard he is. He's desperate to please Mommy and eagerly wants to cum on my cock. The idea is to reprogram him to only be able to cum while he's getting fucked. The association of being able to orgasm being tied to another person's cock is being strengthened in every practice and training session.
In this video, I fuck him with a strapless dildo that is perfectly shaped to hit his prostate in this position. He absolutely loves it.

Subby is doing very well.