WEEK TWO

DAY 8 – Sat 2/8/20

Today was a weird day, my first time not in chastity in a week, as I have been having issues with the base ring chaffing.  When I took it off for cleaning I noticed there is a slight texture to it, and that texture seems to be bothering me. I contacted the designer, and she suggested wet-sanding it. Guess what I’m doing next week?

The effects of not wearing my chastity cage are twofold, the physical and the psychological.

On the physical side, it is really a strange feeling, I grown accustom to the tightness of the cage, but the constant pinching & chaffing of the ring were making it unbearable. After talking with Mistress Delia, we both decided that it was in my best interest to remove it, giving my skin time to heal properly, and for me to sand the ring as smooth as possible.  Details on that adventure will follow I’m sure.

On the psychological side, things are more complex. First I have an overwhelming feeling of breaking Mistress’ rule, even though I have Her permission to do so. I guess it’s just my submissive nature wanting to please Her.

Second, I actually feel lost without it!  The tightness of it has always reminded me of Mistress’s hand firmly grasping my little clit and sissy-nuggets, as she leads me on this wonderful journey. And I miss that feeling, and the sense of reassurance that it gives me throughout the day.  Not that I wouldn’t take this journey without being in chastity, I would! It’s just so much better being locked away so I can focus on other parts of my body, and exploring sexual release through them.

I’ll keep you posted on the sanding adventures once they begin in earnest.

DAY 9 – Sat 2/9/20

Wow, a really long and boring day at work! I couldn’t wait to get home and get into some comfy yoga pants and just kick back and relax!

I did stop and get some Nicorette Lozenges on the way home. I WILL quit smoking in the next 4 months!  Mistress wants her sissy to be healthy, and I will do anything in my power to obey her commands.

I’m beginning to see a change in my mindset too. For example this woman came into today, and as short as 3 months ago, I would have thought to myself “I’d like to get her in bed” now I find myself thinking “God I want to be her when she’s having sex”.  I know part it stems from recently discovering how much I love anal sex! OMG I can spend hours bouncing up and down on my dildo!  That is definitely the first of many such discoveries I hope to make on the Fem-Fabulous journey I’m on.

DAY 10 – Mon 2/10/20

It was a rough day today, although it did start on a high note, as I lost 2.5 pounds last week. Yay ME!

A bit later in the day I begin to question everything about myself once again.  First let me say that I’ve had serious self-esteem issues for a long time, the result of things I won’t go into here, I don’t want to bore you to death.

It all began as I took pictures for Mistress, showing her the thong of the day. As I looked at the pictures I quickly began to slip into a crappy mood. What I saw I simply hated.  I’m over-weight, and out of shape, so instead of the sexy sissy I want to be, I saw the real me. . .  muffin top and a flabby ass, the first step down the stairway to being depressed! 

Next I started thinking about my journey, and if I could ever have the body I wanted. It wasn’t looking good in my mind, so I took another step down the staircase.

As my thought turned to my future, I wondered if I would ever meet that special person. The one I could spend the rest of my days with. . . Step 3 was taken!

Quickly my thought turned to Mistress Delia. She is, simply put, a natural Beauty unlike that I’ve ever met before. An angelic face, with blue eyes that seem to stare into my soul; honey colored hair that frames Her face beautifully; an incredibly toned body. . .  you get the idea, a definite 9.95!  (Don’t call me a sexist; we’ve all rated people before!)

So if this earthbound angel is my Mistress, what was I questioning?  Simply put, Why Me?  Why would someone so amazing, choose to guide someone so lackluster, so blah?  The answer, I have no idea. 

After exchanging some emails with Mistress, one line stood out to me. Mistress said she can see the good in me.  Something no one has ever told me before.

So now as I am about to go to bed, I know I will lie there, pondering Her words, and trying to wrap my head around the idea that Mistress sees something in me, that I simply don’t.  I’m sure a smile will be on my face as sleep arrives.

DAY 11 – Tue 2/11/20

Definitely in a better mood today, I tried on some jeans that had been sitting in my drawer for quite some time now, and they fit, I’m so stoked, a size smaller (no, not sharing my size. . . yet)

I also spoke with Mistress tonight, which is always nice!  We had a nice chat about things going on in both our lives and in my journey.  All in all, a very nice chat!

Well I did it! I choose my quit date, the day I am giving up cigarettes!  Monday, 3/2/20 is the day.  I am going to ask for your support.  If you’re on Twitter, please leave an encouraging word or two. If you just read this blog, please leave them in the comments section.

Cage Sanding Update!  I think I’ve gotten the ring smooth enough to do an overnight test!  I took my time and did the entire base ring with 800 grit wet sandpaper, it was messy.  I’ll let you know if it worked or if it needs more sanding.

DAY 12 – Wed 2/12/20

Didn’t have a good day today, I got into a very heated argument with someone and they said a bunch of extremely hurtful things.  Things that made me doubt my self-worth once again, this time on a level that made me consider abandoning my journey and just continuing my unhappy existence as a ‘wanna-be” man.

I didn’t even do any of what is becoming my new normal routine, Wash & moisturize my face, take my evening supplements, sleep in a nighite. . . I was even short in an email reply to Mistress.  I simply didn’t care!  It’s so hard to try to remain positive, when I am continually bombarded with negative energy from someone close to me.  They have no idea about the journey I’ve undertaken, at least not yet, so I know that is not the root of their negativity, they are just a very unhappy person!

Mistress Delia went the extra mile, making me a playlist of some of her favorite, positive tunes.  She is a truly amazing woman, and I don’t know where I’d be without her!  I know Mistress reads this blog, so. . . THANK YOU AGAIN, Mistress Delia!

DAY 13 – Thur 2/13/20

If you’ve read this far in my blog, you know that I had a really, really bad day yesterday. I spent a ton of time thinking about it.

I was really ready to give up last night, on everything, the journey, myself! Hell I wanted to go to sleep and not wake up!  I know, I would never do anything to hurt myself, but I didn't care.  Then I sat back and just jammed some tunes, especially The Light by Disturbed. . .  and it kinda hit me, the refrain from the song. . .

When you think all is forsaken

Listen to me now (all is not forsaken)

You need never feel broken again

Sometimes darkness can show you the light

Those words made me think and I’ve decided that I'm going to try to take that negative energy that surrounds me, and turn it into something positive I can use on my journey with Mistress Delia!  Not sure if I can, but I'M SURE GONNA TRY!

Also, I need to get into my head that Mistress Delia is always there, and not going to bail on me, like so many others in my life have. At least I hope Mistress isn’t!   I guess I look at Mistress as a calm port in a storm. She is my safe-haven, my refuge, the one place that is safe and I know I'm ok there, with Mistress.  OMG, I am so laying my soul bare right now!  I need Mistress Delia for this journey; I seriously don't think I can do it alone.

I keep having doubts about it, then I sit back and look at some of the pictures I've saved for motivation, and I SO WANT IT.  I know I'll never be as beautiful as some of the pictures I've saved, but I can try my best to be the most beautiful ME possible.  I know this won't be easy, nothing worth it ever is, and I know it will take time. . . thou I want to snap my fingers and instantly be the best sissy Mistress Delia knows!

DAY 14 – Fri 2/14/20

HAPPY VALENTINE’S DAY

WOW!  What a Valentine’s Day!

Around 6 pm I got a message from Mistress Delia to put my edge in and meet her in SL in 15 minutes!  I quickly ran to the bathroom to get myself clean and pop in my toy.  As the toy is new, only the second time Miss & I have played with it, it took me a bit longer to pop in than I expected, but I still made it into SL in time.

As I sat down in my chair, my toy firmly pressing against my needy prostrate, my phone chimes. It’s Mistress asking for control of my toy, which I gladly gave her.  Quickly a soft buzz begins to radiate thru my sissy-pussy.

As I connected to SL, and accepted Mistress’ call, her sensual voice filled my headset. . . “Hello Sweet Sissy, how does that feel”?  Oh My God! It felt. . .  well Amazing would be an understatement! As Mistress and I talked, She varied the intensity & pattern of the vibrations, exploring all the combinations that the toy was capable of, and there are quite a few!

Soon I was begging Mistress Delia for permission to play with my sissy-clit, to which she replied, “Go ahead Sweet Sissy, it is Valentine’s Day and I want you to have fun”.  Quickly smearing lube all over my freshly shaven sissy-clit, I began to rub just the tip, as stroking is Strictly Forbidden!  The combination of the toy in my sissy-pussy, and the sensation of rubbing my clit was beyond words; I was gasping into the mic, and hearing Mistress’s obvious pleasure at being in total control.  Soon I had to stop rubbing my tiny clit, as I didn’t dare make a cummies without permission!  Mistress responded by increasing both the internal & external vibrations of the toy. . . OMG I thought I was going to die!

After Mistress brought me to the edge a few more times, I was begging Her permission to cum. Mistress chuckled in my ear and told me to go ahead and make a sissy-cummie.

I am at a total loss for words in trying to describe what happened next! 

My clit remained totally limp; the head was so sensitive I thought it was going to explode. . . I was gasping, rocking my pussy against the chair like a sex-crazed sissy slut, which I am beginning to believe I am!  The sensations pulsing thru me were earth-shaking. I do remember telling Mistress, “this is what I was made for. . . being a total sissy-slut”!  For the first time during this play session my sissy-clit began to swell, not much, maybe a 20% increase in size. . . Then BOOM! The freaking world exploded! I felt every nerve in my body stand on end, and then proceed to do their own version of a “happy dance”!  I had never in my life felt the sensations coursing thru my sissy-clit, my ass, my body!  I could hear the intense pleasure in Mistress’ voice as she asked if I had a “sissygsam”. Quite frankly, as I write this the morning after, I have NO IDEA!  I do know I definitely WANT that feeling again, and again and again!

Thank you for the BEST Valentine’s Day EVER Mistress Delia!