dee3239 The Path of Dee: From D... to Her Sissy Wife

member_b50ddfe27c · 2026-08-25T11:45:44.000Z · 0 replies

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2026-08-25T11:45:44.000Z #1

My Wife/Mistress and I had discussed putting me into chastity before my recent business trip, spending a day or two testing it out. During that last trip, all I could focus on was being locked up with her holding the key. Being the good submissive who prefers to top from the bottom, I purchased a Holy Trainer v2 and sent it to her while I was away, expecting to be secured upon my return.

I have been locked since Sunday and feel like an emotional whirlwind. My manhood is about to fall under Mistress’s complete control, bringing me deep peace with myself. I have a strong desire for Mistress to feminize me, transforming me into her wife, sissy servant, and perhaps even her cuckold.

Initially, the HTv2 was too tight because I bought the smallest ring, so I had to remove it temporarily and switch to the CB 3000 that Mistress had bought earlier. I plan to go back in the HTv2 within a month or two; the smaller tube will highlight my shrinking manhood as I transition into a sissy cuckold husband.

Mistress is somewhat ambivalent about becoming a KEY HOLDER. During this transition, she lets me access the keys so I can remove the device if it becomes unbearably painful. My hope is that she will soon deny key access without permission, requiring begging or some other tribute.

I didn’t realize how much I enjoyed touching and caressing my cock/clit until I could no longer feel the sensation of my fingers stroking, massaging, and caressing it. It’s not the orgasm I miss; it is the tactile feeling of being caressed. Sigh.

As I start this journey, one final thought: My desire to please men sexually has grown exponentially lately, especially since going locked up. Is this common for chaste men, or does it apply only to sissies?

Thanks for reading. Feel free to comment or write me directly. D… soon to be Dee

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