The Chastity Chronicles - Looking Back at My First 10 Day Journey

 Originally posted July 10 2015

(say hello to my little friend locked away for safe keeping)

There was a time in my sissy life when I didn't understand at all how chastity could benefit me. I never associated chastity in my life as most examples I saw were to control filthy male subs and to make them more docile. Being very in touch with my Feminine sissy side, I saw myself as naturally docile, and obedient, plus combined with the years of training received from Mistress Morganna, Lady Diva Cane, Suzanna Stern, Lady Bernadett, Mistress Patricia and others, this made me so.

It wasn't until my sissy training developed into more advanced stage, where it began to dominate my 'other' vanilla world in terms of sexuality and desires, did the benefits and advantages of chastity began to come into focus. Since the only Women in my life were Dommes, there was no chance on me ever cheating sexually, so I never got 'it' in terms of chastity. But once Lady Diva and others began to condition the real me into pure Female devotion and away from anything resembling Female desires, the only thing left to crave, and lust after was my other true love: Trans Women

Before when my EME (emasculated male ego) still had an influential role in my daily life, my experiences with the third gender was more as a cock sucking top, so to speak. Now as Devina, with my EME thoroughly pulverized into subservience to my emerging Feminine side, I no longer craved to fuck Shemales, no no... I found myself longing to be fucked BY them! Even more, as I've now shared with you, I wanted to be fucked by them as the REAL me, Devina!

This wasn't something that happened overnight. No a seismic shift like this takes a tremendous amount of gentle pressure, relentlessly applied. Many long Girl/gurl chats with Lady Diva and every other positive encouragement from every other Domme who has graciously accepted me as Devina has led to this:

I know I'm a sissy.

I love being a sissy.

I know that I can never please a Woman in any traditional sense, unless I serve Her via submission.

Every TGirl/Transgender/Shemale is above me.

My only source of sexual fulfillment from here on as Devina is through serving Shecock.

Serving Shecock means never using my sissy-clit for gratification.

Serving Shecock means giving up my asspussy to be fucked like a Girl.

Being fucked like a Girl means never achieving orgasm like my old male discarded self.

My EME no longer serves any purpose for sexual fulfillment. Zero.

Sexual fulfillment now means learning to orgasm like a Woman...

Now sissy chastity had a purpose in my life!!!!

 

As with so many discoveries along my sissy journey, my milestones tend never to be reached by a linear or usual manner, and the decision to secure my own chastity device was much the same way. Lady Diva didn't have to threaten me with chastity, instead She encouraged me, encouraged my growth as a sissy, nurtured me to want to lock away my sissy-clit in order to grow as a gurl. I was so proud the first time I arrived to Lady Diva's dungeon with my sissy clit secured under lock and key! There was no option for me any longer to even provide my EME any gratification in the slightest sense. My purpose was clear; to serve. My rewards would solely be at the discretion of Lady Diva, or any Domme for that matter, and since She encouraged Devina to get as much Shemale cock as Her little slut's asspussy could, so what reason would I ever have to revert back to my old ways?

 

This was how sex would be for Devina now! Devina was fully empowered to not only control her own Feminine desires, but now encouraged by her Mistress to act out and live those desires as often as possible!

As I've shared in my blog elsewhere, my initial interactions with Shecock were as a locked up male, but the stage was now fully set to have Devina assume the starring bottom slut role. Each locked up encounter further cemented my raging desire to be seen as and fucked as a sissy gurl, and by as many Shecocks as possible. My encounter with Sunshine, was the opening of the long awaited gateway to the world I've dreamed of. But with all that wondrous joy and positive growth, remains perhaps my greatest challenge as a Feminized sissy: The Sissygasm

 

My all encompassing goal in my sissy life is to experience what She is above. I crave to have a searing hot Shecock fill me up, pound my asspussy to nirvana and bring my mind and body to a shuddering Female orgasm. I want at that moment to clamp my asspussy down on that Shecock as I cum out of my sissy-clit, leaking all through my chastity cage, all knowing that the instrument of my Womanly pleasure was delivered by a Shecock. My devotion to Femdomination by cumming as a Girl, firmly cemented, and in turn making Lady Diva proud Her sissy slut.

 

Of course practice makes perfect and my sissy adventures both in public, in Lady Diva's dungeon and at home have been in trying to master the art of discovering my path to sissygasm. I've been fucked and facialized by Shemales while in chastity, and each time a wanton and willing cumslut to each of them, and each time I've rode that wave as their Shecocks fucked my asspussy, but the wave never broke.

Lady Diva has plowed my asspussy with a variety of strapon cocks, and almost split my asspussy in two with a huge 12" monster, but the wave never broke. I've ridden Her monkey rocker, controlling the stroke, depth and speed and rode that wave, but the wave never broke. I've used my own assorted dildos and cocks until I was a spend sweaty mess, getting oh so close...But the wave never broke. Which brings me to today. Day 10

 

Like with all things I've learned in my sissy journey is whenever I've tried to force things, they don't work, and certainly my sissygasm quest has suffered from trying too hard. No, what's always worked since my very first pair of sniffed panties that belonged to my sister-in-law, Anna, as a teen, was gentle pressure and encouragement.

10 days ago I locked my sissy-clit, not for a session with Lady Diva, or an encounter as the real me, Devina with a beautiful Shemale to be a cumslut for Her Shecock. Instead I did it for me. To gently build the pressure in my p-spot, to make my sissy balls ache each time I would enjoy Shemale/Femdom/Sissy porn, (which is daily and often), and to condition my sissy-clit to shrink a little each day, denying it the ability to even stretch out during the night when biological functions allow sissy hardons. No, this will be gentle pressure applied and soon enough I hope to be experiencing encounters again as Devina before Shecock, in hopes to find sissy nirvana.

So with each day that passes, my conscious and subconscious mind will continue with my sissy programming of Femdomination and Shecock, all while my sissyclit is locked away until finding release through Womanly orgasm. When that day cums, it will be in honour of every Woman who held my hand to get me this far. My sissygasm will be because of all of You

Wish me luck!

oxoxox

Devina

 

Author's note, 9 years later:  

Today I've been locked in Sissy Chastity for close to 2700 days now, and it's almost emotional to look back on my first steps on my sissy chastity journey. Locktober is a great time to reflect on how the sissy chastity journey can truly change your life, all for the better!