March 31, 2026
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March 27, 2026
The Chastity Chronicles: 1000 Days Locked & a Sissy's Open Letter to her Mistress
Originally posted March 23, 2020
Once upon a time there was a rather pathetic male subbie who had given into the dark desires that consumed his young mind, and who had given into the fear of the complete unknown and placed himself into the hands of a true Breaker of men, in the form of Mistress Morganna. It was through Her systematic no-nonsense re-programming of a large number of disgusting male traits I had held since adolescence, that I began to see through a dimly lit haze, what might be the real me that spent a lifetime since early childhood hidden in shadows, and in the deepest recesses of my mind and my soul. Mistress Morganna began to rebuild my foundation as a lump of clay before Her, and began putting the building blocks together that would ultimately be the foundation I stand upon today.
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Mistress Morganna's gracious act of introducing me to You might have been the single most life altering moment in terms of my life path and where it suddenly began to draw me towards. All the deep secrets I held, and any guilt or shame, and confusion that came with them, slowly began to feel less frightening as I felt a connection to You as a submissive. My desire to explore BDSM (and later the Feminine side of my personality) did not grow from a desire to be punished, or to be taken down a few pegs for a short period of time by a strict Woman. Nor was it to be ridiculed and humiliated from a sense of vulnerability. I think from the very first time I touched a Woman's pantyhose clad legs as a youth and heard laughter from all the Women in our house who thought it was cute, the reaction I had, was to find a place where I could connect with that initial moment and allow that seed to grow in a place that could nurture it and protect it until it was strong enough to grow on it's own.
That's what You gave me, even before I really knew it myself.
With each step I took under your wing, You became the Big Sister who always was in control, and who I began to trust would never lead me astray. You made a space within Your world, among all the various kinks, fetishes, sadisims, and perversions of the mind and flesh, for a very nervous closet sissy who yearned so badly to share her true self with someone who could understand me. Your chats over the years with me about many things, built a bond that was always built on Your Dominance, Your Guidance, and Your Wisdom, yet it allowed me the freedom to grow and to learn about who and what I was, and the ability to seek my truth where it led me.
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In turn I took the lessons that Mistress Morganna and Yourself forged into me and always remembered that my relations with anyone in the kink/alt lifestyle world, would always be a reflection on You. Manners, politeness, patience, and a lack of ego, with the openness to always learn was what I carry with me always. With any compliments I have received along the way, I always made sure that You received the credit for shaping me who I was at any given time; then and now.
Domme / sub relationships come in all shapes, styles, sizes, and patterns. There is no one size fits all, and You know this as well as anyone. In the years where the male sub you began to re-shape needed the time and space to reconcile a growing and undeniable love of Transgendered Women, with the very real and emotional sissy that was breaking free from within, You not only allowed me the space to bring those worlds slowly together, You always encouraged me. You never shamed me, or ridiculed me, but instead You empowered me. You encouraged me, and congratulated me on my sense of taste and unyielding personal code of what I wished to be based on who I new I was.
So many times after one of our many Girl/gurl (sister chats as we called them) talks, I would beam with a sense of confidence and warmth in knowing that someone out there truly understood me, and cared about my well-being. You have always shared in my personal picky high standards in people, and as a result, I grew in confidence as the sissy I was slowly becoming for real. I began to feel at ease with sharing any twisted secret of desire I had with You because I always knew I would find acceptance and never face judgment for the things I truly loved. You were the first to completely understand me when I expressed that I was a sissy lesbian, and that my love for Women only deepened when expressed as Devina.
Thanks to You I began to make Your dominace the centrepiece of my sissylife, as I slowly branched out to have Devina's own circle of Female friends. In that time, Your graciousness has brought me the gifts of friendship from as many as 8 other Dominant Women along with several other Trans Women. What this has given me is a circle of Female influence on my life that touches me on a daily basis in some way shape or form, and You have never felt threatened by it, which deepens my bond to our relationship even more.
When I began my sissy chastity journey, it was not with any fanfare, or boasting of what I wished to do. It was instead a quiet devotion to You, and later Maitresse Cathie LaDivine (who became another beloved Dominant Sister who brought nothing but love and encouragement to my sissylife) as a form of sacrifice and a way to honour daily what You have made in me. As the days became weeks, and the weeks into months, I began to experience a metamorphosis, on a deeper physical and spiritual manner. With the physiological changes of extended chastity, a deeper emotional connection was made to my submission to You and to the Feminine circle around me. It was that connection and spiritual bond that changed the entire way I first saw chastity training. Chastity was not something to be endured, with a finish line, but a method of discovery, and a path forward to personal growth.
Your empowerment has now allowed me to create a world where the very fabric of who I am and what I need for personal fulfillment has morphed into something I could have once never, ever thought possible. You have allowed me a way forward where what is physical satisfaction, emotional satisfaction, and spiritual satisfaction now center around the needs of Devina the sissy, not the carrying case she came into this world with. You have made it possible to express my love of Trans Women and Shecock in all it's forms without prejudice or shame. You make it possible for me to feel the warmth and love that a Dominant Woman can express in Their own unique ways, even in times when I don't always love myself. For that alone, I cannot express how much that means to me.
Day 1000 is not a destination, it is merely a sign post on route to somewhere beyond. As I always try and seek balance with the needs of Devina with the world around us (which has seemingly gone mad; more than normal), I always know that You are a constant. You are one of the rare few that know me in ways that less than a handful on this earth do, and that makes You a rare gem to me
Thank You, Lady Diva for allowing me the opportunity to give my Chastenial gift to You. I'm more proud of You having my gift, than in anything I sacrificed to earn it for You.
Your Sissy Always
Miss Devina Cox
March 26, 2026
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March 21, 2026
Spring Comes and Devina Gets Horny
I'm still buzzing on cloud 8 or 7 as I share this with you all, but the ebony goddess above just finished pounding my little asspussy and treating me like the proper slut I really am.
My day was spent preparing myself by being fully shaven, clean (inside and out gurls) and the favourite part, picking out the proper outfit. It had been a few years since I have seen Sunshine and a lot has changed in my life, although my last encounter with Her had her fucking the living hell out of me too, and perhaps signalled the inevitable change that was to become in Devina. But I was just a bottom boi bitch back then, not what I presented to Her this evening.
I came out of Her bathroom in a black, white, and pink mini dress, knee stockings with pink bows at the back, pink Mary Janes and my sissy clit locked in it's chastity and graced in a pair of pink lace panties, along with Devina's trademark red locks. Needless to say Sunshine was surprised but pleasantly, much to my relief. She embraced me like a sister and we both sat on the bed chatting and catching up on my new persona.
She was blown away and loved the new person She saw before Her and couldn't wait to see more of me. I showed off a little as She took me all in and then refused to wait any longer as She had me assume the position, on my knees with Her black growing cock in front of my face as I immediately did what a gurl slut does and gorged myself on Her cock.
I was soon bent over, knees on the bed, Mary Janes pointed toes horizontal like a good slut does, as She began rubbing Her lubed cock all over my asspussy. My mind raced back to the last time, years earlier when I was in the same position, just a hairy male bitch. Now this was different. This was an entire evolution of the real me! I was shaven fully, sissified, cocksucker lipstick smudged and asspussy exposed and eagerly needing to be filled. Sunshine slowly entered me and with steady force began to open me up. "Oh my!"
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"Oh Devina, you like that?" She cooed
"Fuck, I love Your cock in my asspussy! Fuck me!" I moaned, loving each thrust.
By now I was not being some lethargic bottom boi, like long ago. I was being impaled by this black She-cock of my dreams and I didn't want it to end. I was driving myself on it, losing myself on it, rotating my hips and clenching on it. I was a slut and I wanted to fuck this She-cock like a dirty whore would. No quit, no stopping, just being used like a slut. For the first time, Devina was outside Lady Diva's Dungeon and being exactly what she's always wanted to be. Each thrust of black She-cock confirmed my place, my purpose, and my reward for devotion to the Feminine Spirit. The Universe at that moment was rewarding me for my love given to all Dommes, all Women, and all TGirls. My reward was being fucked like a sissy gurl, my sissy clit locked away and useless, pleasing the cock inside me with my asspussy, my enthusiasm, and my wanton desire.
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"I LOVE Your cock in my asspussy...pleeeeeeeaaase fuuuuuuuuck meeeeeeeee!!!!" I hoarsely moaned as She grabbed my hips harder and with one hand pushed my face onto the bed, giving Her full entrance deep inside my asspussy.
Sunshine pounded away a little while longer until She gave me one last deep thrust feeling Her balls slap my ass as She ordered me to turn around because it was time for a slut's reward: A face full of cum! A cumshot from Sunshine is more akin to taking a cumshower, and she painted my face, lips, chin, hair, dress, boobies, and I lapped it up willingly. A final kiss on the head of Her cock was the icing on the cake, taking a last glorious taste of She-cum.
I stayed between Her legs long after Her eruption as we talked about Lady Diva's progress with me and how She would like to take part in my ongoing training. This sissy was indeed heaven! A face full of She-cum and knowing that coming out to Her as Devina was now going to pay off in my ultimate dream to be with lady Diva and Shemales at the same time.
It was a beautiful night as I took another step on my own as Devina, and was embraced by a beautiful TGirl who not only rewarded my courage, but after She encouraged me to keep transforming, and not to turn away from it. Those words of acceptance and encouragement were so welcomed by my inner Femme spirit. Tonight I got to be who I really wanted to be the first time I surrendered my asspussy to Sunshine years earlier, and I couldn't be happier...
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