April 29, 2025

The Chastity Archives - 30 Days in the Hole. Locked, Limp & Leaking

 Originally posted July 27, 2017

 


 Tonight begins Day 30 for me in sissy chastity, for no other reason that to please the Dominant Women in my life, and to honour them by reaffirming my devotion to Femdomination. Every sissy should push their own limits, boundaries, and personal bests. My previous personal best in sissy chastity was 39 days and I hope to eclipse my personal best by a wide margin.

** Editor's note: Today is Day 2863 in Sissy Chastity. I think I exceeded my goals :) **

Each time I've given myself to locking my sissyclit, the goal has been to deepen my sissy experience, both physically and mentally, and each time I have, including this time. For the first time in my sissy life, I'm leaking and those experiences only reinforces the fact that I'm indeed a real and evolving sissy gurl. Sissy gurls strive to have their sissy clits shrink over time, and leak and dribble, and to learn to cum like a Woman, via penetration of their asspussy. For all the amazing Feminine experiences I have been bless to have in my life, this is indeed a milestone!


 

I can't always control when I'm about to leak but the sensation of trying to hold it, delay it and enjoy it has been most challenging. I hope that the longer I go, the more I can try and harness this Womanly power that has been blessed upon me. I so badly want to feel my Mistresses' cock fill me up as I leak for Her. I want to feel the sensation of real Shecock pounding my P-Spot as I leak all over my thighs as I shudder with delight. I'm at the precipice of my most Womanly experience to date and it is as exhilarating as the first time I put on my Sister-in-law, Anna's panties!

The best part of extended sissy chastity is the anticipation of my sissy clit atrophy that shrinks a sissy's clit over time due to lack of nasty erections, and the physiological conditioning of the mind and body to accept that you are no longer able to experience sexual gratification via your pathetic little penis. It would be truly wonderful to one day experience sissy sex with a fully limp and useless sissyclit with no chastity device, bouncing away as my asspussy gets filled with Strapons & Shecock. That is the goal, to deepen my experience fully into this sissy life. To make those Women who have embraced me, truly happy to see that their plaything has morphed into something beyond return.

 


The next steps are to combine the sissy leaking with manipulating my sissy p-spot to experience a full blown sissygasm. Sissy's always have new goals on the horizon, no matter how far they have come in their journey. That's what makes being a sissy so rewarding....the journey is never ending!

Devina

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