THE FIRST WEEK OF FORMAL TRAINING!

DAY 1 – Sat 2/1/20

As I awoke at the ungodly hour or 3:00 AM to get ready for work, the thought hit me again; Today is the FIRST DAY of my year long journey into sissyhood!  Excitement and fear coursed through me, yet Mistresses words filled my head “You Deserve This, My Sweet Sissy” and that’s all it took to calm me down enough to dress for my day.

Sitting on the edge of the bed, I dressed in the outfit Mistress had prescribed for me. As I rolled the nude colored thigh highs up my shaved legs tiny sparks of excitement shot thru them, it was such a delicious girlie feeling. Pink panties and a cami-tee quickly followed. I took a moment to look at myself in the mirror, and what I saw shocked me. I saw the REAL true me, the one who had laid dormant all these many years.

Quickly slipping my jean and a fleece pullover, I was off to meet the world. Work was long, an 11 hour shift on Sat, but I hardly noticed, as small waves of pleasure raced up & down my legs as my jeans rubbed against my thigh highs, such a wonderful feeling.

Arriving home after work, I had a quick dinner and was off to play a bit of Xbox before crawling in bed and drifting off to a blissful sleep listening to my sissy hypnosis files, I didn’t even fuck my sissy-pussy with my vibrator, which is quickly becoming one of my favorite things!

DAY 2 – Sun 2/2/20

Waking up early, 4am SUCKS!  The only thing that kept me going once again were Mistress’ word echoing in my head. . . “You Deserve This, my Sweet Sissy”, and knowing that I’ve taken the first steps on my way to total sissyhood!

I quickly slipped on black thigh highs, panties and a cami-tee and my YUCKY boy clothes and was off to work. Yep I work weekends so I’m free all week to concentrate fully on my sissificiation! Pretty good gig in my opinion!

Sometime in the late morning, not exactly sure of the time, this really cute, fit guy came in the shop. OMG he smelled so good, and was dressed all in black, and my only thought was to walk around the counter, drop to my nylon clad knees and take his cock as far as I could in my mouth!  A feeling I’d never had before, so I guess being locked in chastity does have its advantages!

That evening, after watching the Super Bowl, I decided to have some sissy fun. Gathering up my toys, I lay back on the bed and proceed to fuck my sissy pussy for close to 45 minutes.  OMG! As my toy eased in, and the vibrations hit my p-spot, my little clitty felt like it was going to explode, but it was not to be that night, the damn battery died!  Note to self, charge the damn thing daily!

DAY 3 – Mon 2/3/20

Today was filled with self-doubt. Doubt that I could ever attain my goals. Doubt that I was good enough for Mistress, Doubt that I’d ever be able to achieve a sissygasm.  All in all, a crappy day!

It begin when my new pink nightie arrived, I quickly opened the package and slipped in on, wanting to feel the satin on my freshly shaven body. Well I ordered an XXL, yes I’m a plus sized sissy, and much to my dismay it was too tight!  Well that’s all it took to trigger my thought of not being good enough.  Mistress ordered me to come up with 5 positive things about myself, and I’ll admit it was a struggle.

The day however did end on a positive note, I got to talk to Mistress for awhile, and hearing her intoxicating voice always helps.

DAY 4 – Tue 2/4/20

Today was a day of self-contemplation and my commitment to a NEW MINDSET!

It carried over from yesterday, which was a really bad day for my mental outlook on my journey.  At one point yesterday I actually considered just giving up, but Mistress Delia, with her infinitely superior female wisdom set me back on course. 

I spent some time looking for images to use as a screen saver, images that promote my positive self-worth as Mistress’ sissy, and I found the best Tumblr page (https://gymbunnycandiehart.tumblr.com/) Around Thanksgiving of 2019 she featured a bunch of images that she titled “I’m thankful for…”  They are really amazing and hit home for me.  Instead of being so down on myself for things about myself I don’t like I need to be thankful. So in that vein, here are 5 things that I am thankful for.

1)      I am Thankful for my Mistress Delia, her wisdom, and her ability to see the true sissy in me.

2)      I am Thankful for Mistress Delia collaring me as her sweet sissy as we take this journey! I would be lost without her guidance.

3)      I am Thankful for the opportunity to embark on this wonderful journey into sissyhood!

4)      I am Thankful for knowing that I have within my sissy soul, the ability to change things about myself I dislike.

5)      I am Thankful that each day as I awake; I have the opportunity to take at least one small step in my journey to be the REAL ME!

Day 5 – Wed 2/5/20

 Today was a good day! 

My New Mindset is working out wonderfully, and I even went so far as to make myself a new screensaver with the 5 items I am Thankful for! 

Keeping with my new POSITIVE outlook, I’m not sure if it’s possible or not, but the anti-aging skin care routine that Mistress put me on seems to be working.  I keep finding myself caressing my cheek and am amazed at how soft it is.  I can’t wait to see the results in a month!

UGH!  My chastity cage is driving me crazy!  Not from pain or discomfort, my left sissy-nugget keeps pulling out of the ring and I have to remove it to put it back in. A total pain in my sissy-ass and a waste of time!  So if anyone has a suggestion, please leave it in the comments section!

Day 6 – Thur 2/6/20

I had an amazing adventure with Mistress tonight. My new toy, a Lovense Edge finally got broken in. . . And let me tell you, this freaking thing is amazing.  First, I’ve never used anything like it and it took a bit to get it in my sissy-pussy (learning curve), but once I figured that out, I think it will be fairly easy to insert. Second, it’s the most powerful thing I’ve ever had in me, more on that in a bit. Third, it’s remote controlled, so YES, Mistress had total control of it.

Once I got it inserted, Mistress & I ran thru a quick setup of the connection, very simple and easy.  Moments later my sissy-pussy and nuggets began to vibrate, with Mistress in my headphones saying something to the effect of “Mmmmmm, can you feel that?”  HOLY CRAP! Did I ever! After Mistress finished laughing, she began to explore the different options available and to quite literally make me squirm around in my chair! After about 30 minutes of driving me wild, Mistress decided it was enough for our first night.  I was so horny, I asked Mistress’ permission to make a cummies, and thank God Mistress allowed it. 

Stripping off my panties, I lubed my sissy-clit and began to rub just the head of it, the only way I’m allowed to diddle, NO STROKING is allowed. Well let me say, it didn’t take me very long to make a cummies.  It was very different that cummies I’ve made in the past, it was way more intense, and my sissy-clit didn’t seem to get as hard, YAY! I hope the lack of hardness means the Limp Clitty Hypno I listen to nightly is working.

DAY 7 – Fri 2/7/20

YES! My new cage arrived today, and I couldn’t wait to get it on!  It’s an early Valentine’s Day present for Mistress; it has a heart on the top that has 2020 in it, and a heart mesh along the bottom. It has special significance for Mistress & me.  2020 is the year of my journey into sissyhood with Mistress Delia, so the date commemorates that fact.  And the Hearts show my undying love and submission to Mistress!

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