May 4, 2025

Chastity Chronicles: Breaking Boundaries- Day 37

 Originally Posted Aug 3 2017

 


 My entire sissy existence has been about pushing past internal and external limits, finding exhilaration in realizing a new level of being, and then finding ways to break down more boundaries when it feels right. From my first pairs of panties jerked to as a teen boi mesmerized by my sister in law Anna, to my first cock in my mouth, then first cock in my asspussy and all points in between, there is always that next new step.

Chastity never was on the radar in my sissy life until I reached a point where it all began to make sense. One reaches a point where they have emasculated their own male ego to the point where it's worthless and crushed, and it becomes an act of love and devotion to the Women in your life who have welcomed you as a feminized sissy. Up until today, my longest period in full chastity lockup was 36 days, and tonight begins day 37. A new frontier!

 


Over a month into sissy chastity brings so many physical and psychological changes. It makes you more docile, more in touch with the sensations of your seemingly ever sensitive p-spot, and each day as you devote yourself to Femdomination, you deepen the bonds to the Womanly powers over you, be it near or from afar. This time, my extended lockup has brought me the unbelievable joy of experiencing my sissyclit leaking; dribbling into my panties, and the feeling is incredibly naughty! You feel like such a dirty gurl and you know you have to wear those panties for the rest of the day to remind you what and who you are. It is a mind fuck all it's own..

 


This past week I began taking longer showers fucking my asspussy with my own suction dildo, hoping to find that magic sissygasm from cock in my asspussy and it's closer than I've ever gotten before. Differentiating between a pee sensation and a sissy leak sensation is what I'm trying to learn and control, and I know I'm close. I want to so badly feel my thighs wet with sissy cum dripping out of me as real Shecock pounds my asspussy. I know what a powerful drug that will be, and perhaps my psyche is holding back, because it knows that when I reach that experience, I'll never want to cum any other way ever again.

I know all too well how taking real shecock in my asspussy took me to a whole other level as a sissy slut, and I just know that being made to cum by shecock fucking me, will be an amazing high. Like with all the other sissy milestones in my life, patience is always rewarded....

 

Editor's Note: It's so bemusing for me to look back from today which is day 2868 in sissy chastity to see me then. 37 seemed like such a huge number, and now the months go by without fanfare. The journey is the thing.

Devina

 

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