Well, it appears that i am at a cross roads that reminds me of a similar state of affairs back in 2008. It was in May of that year that i had my first phone session with Mistress Cassie.
i had been silently following Her website since 2003. Not coincidentally, it was in 2003 that i purchased my first plastic cock cage, The Curve. Prior to that purchase i had dallied with several leather devices and one metal/ leather contraption, called the Gates of Hell pictured below.
While The Curve proved to be the most effective and secure chastity device, they all had one thing in common. i found them very compelling before masturbation. i used to subject myself to rather short periods of abstinence, locked up, prior to masturbating. The ultimate goal was to masturbate while fantasizing about a Dominant Female (like Mistress Cassie), then put the device on after cumming.
As was the case with all of my devices, the Curve was not something i could ever lock on after masturbating. It was simple really, it all added up to this:
Prior to May, 2008 i had ALWAYS masturbated with panties and usually a slip. And after masturbating, i had ALWAYS quickly taken off the panties (and slip or girdle) - ashamed and determined not to do it again.
It was a never ending game of denial about my cross dressing compulsion.
But the allure of lingerie, of Female Domination and of toys of imprisonment just kept eating away at me. i finally submitted to Mistress Cassie in May of 2008 on the phone. That first session was basically about the cage. i told Her that i couldn't adorn it after masturbation. i essentially challenged Her to masturbate & cage me.
Mistress took control quickly and completely that night. Not only did She get me to cum and cage me, She kept me in my slip and panties. Those many years of shame and embarrassment of my long time addiction to cross dressing suddenly ended - forever. That night was the start of a the ongoing feminization of sissy diane by Mistress Cassie. Back then, i would adorn a pair of panties and a slip for a few minutes, and then, after masturbation return the delicates to their hidden location.
It all started with that very fateful phone session nearly 4 years ago. Now, the cage plays a central role in my femming. Yes, it is on ice - literally, but it still pulls at me. It has gone on too many times these past 4 years to stay on ice for long. It more than symbolizes the beginning of my femming, my submission to Mistress. Not only did the cage come front & center that night, but my lingerie came out of the closet for good.
So, what's happening today? Well, there's another type of sex 'toy' that has long had my interest. The artificial Pussy. Sex toy provider's world wide have long sold numerous versions of plastic Pussy's as masturbator's. And i have purchased a few. Here is one that i have owned for a while and have fruitlessly hammered away at numerous times:
They all have one thing in common for me. i am fascinated by them , but have NEVER actually cum in one. The idea is compelling, but for some reason i just can't cum. i need to feel the silkiness of panties, and still usually a slip.
Now comes the fleshilght. i posted about this toy some time ago when i became quite enamored of a Model, Brandi. Brandi was teasing some guy (along with a cute Girlfriend) using a Fleshlight. So, i ordered one and expected delivery a couple of weeks ago. Well, it was on back order and it finally arrived last Friday.
And wow, was i excited. Friday night i dressed up, got in front of my computer and watched the tease & denial video of Brandi and Friend. i lubed up my new Fleshlight and went to town. It felt great, absolutely wonderful. It instantly took on the status as best plastic Pussy ever for me. i feverishly set about pumping my clit in and out of that slippery delight. It had been several days since i masturbated and i fully expected to cum, FINALLY, into a plastic Pussy. After all these years..........
Then, a funny thing happened on the way to orgasm. i couldn't do it. Like the poor guy in the video, i was on the edge, but no go. i guess it came down to this - it was too important a moment to give to Brandi. She is part of Mistress Cassie's hierarchy. Like any other of the many Models in my porn collection, Brandi plays a role in my day to day femming. Mistress Cassie's time is too important and She has too many sissies in Her barn to worry about the details of day to day sissification.
So, for better or worse, here's the conclusion i've come to, with my Fleshlight in hand. This looks like a May 2008 situation. The implications of finally cumming into a 'plastic Pussy' are significant. This is not a moment for one of Mistress Cassie's minions.
This calls for a session with Mistress. Only She can get me to cum into that artificial Pussy. i know that this looks like another 'Be careful what you ask for' moment. Mistress has repeatedly demonstrated in the past
what that can lead to.
But i am compelled to throw caution to the wind, and leave it to Mistress to decide what comes next with the Fleshlight. Until i hear from Her, the cage is on ice and the Fleshlight is on hold.
But make no mistake about it, i want that Pussy and i want it bad. i need it!
If She beckons me to the phone, so be it. If She chooses to brush Brandi aside and have me cum into the plastic i'm guessing we're entering into another phase of my femming.
If that's the case, i think i've finally encountered the perfect orifice to demonstrate the depth of my pussification by Mistress Cassie.
sissy maid diane
I am also going to remind you what I tell ALL of my callers, ' I will take you deeper and deeper, and there is no way out '
you are a very good sissy, and I am pleased that you love Me and always do your best to be a good girl.
you are the pussy now diane. you are pussified. a plastic toy will remind you that. this plastic pussy is the closest thing to a real pussy you will get now. you are My girly girl sissy slut. you may call Me tonight, for a session with your new toy, however, there is no guarantee that you will be allowed to cum. you must earn it.
talk to you soon,
Mistress Cassie