A heartwarming dedication

i got the most heartwarming "sweetest" note in my chocolate wrapper last week! It made me smile both inside and out. Because as soon as i read it, i knew how true it really was.

It seems like all too often i read stories or chat with other crossdressers who are married, and their wives either have no idea or are disgusted by their dressing. i don't know how i got so lucky to have found the perfect soulmate who truly does "accept me completely".

This post is dedicated to You, Miss Scarlett. You are the greatest gift a submissive sissy could ever have. You've made me a better person over the years. You've allowed me to explore my sexuality without judgement or criticism. We have had so much fun together, and there is no person i would want to spend the rest of my life with!

Love always,

~sierra

An up(down?)grade

For the past year and a half, with the exception for a couple months i was in a pink Cherry Keeper, i have been wearing a shortened version of my original Mature Metal Jailbird. Shortened from 3 1/2 inches (who was i kidding!) to 2 1/4" (which fit MUCH better). i have been tossing around the idea of going just a smidge shorter though. Well i have been talking with a friend who i meant within the chastity scene. He had offered to send me an unused Mature Metal cage he had which was shorter than mine. 

How much shorter, well "just" 3/4 inch. 3/4 of an inch doesn't sound much, but when you're talking going from 2 1/4 inch to 1 1/2 inch, that's HUGE. And let me tell you, it is tiny. my first reaction was "i'll never fit in that". i was wrong. Not only did it fit. It's so much more comfortable. Yes my sissy clit is quite smooshed in there fairly dramatically. 

i've been wearing it now for the last 3+ days with zero complications. Using the toilet, not an issue. my Fear was because i was so smooshed in there, that i wouldn't be able to keep it clean and dry. Well, that doesn't seem to be an issue either. It's infinitely more comfortable wearing under my "normal" male clothes too, especially under jeans. 

It's not a 100% perfect fit, and the only reason i say that is becuase of the nature of a custom made cage. Each cage is "married" to a ring simply due to the nature of hand made products. So this cage doesn't line up exactly right with my ring. It's slightly off center. Now i need to decide if i'm going to send my cage back (which i THOUGHT was perfect) to have it shortened. And by how much???

~sierra

Some time away

i just got back from a trip to visit some family. Due to schedule conflicts, Miss Scarlett was unable to come along. I was 100's of miles away, and many states. But remained securly locked in chastity. i did however have the key with me. In a lock box that i have no idea the combination to. Just for emergencies. 

Why was this a big deal? i haven't been unlocked in nearly a month, yet somehow this felt different. Like it felt more permanent. Like, chastity is no longer a game like it started out as. Would i have been locked if Miss Scarlett was with me, 100% absolutely yes. Would i have a chance of being release? Chances would likely be less than 1%. 

What started out as a fun little game of foreplay so many years ago has completely evolved into something entirely different. Chastity is now a way of life. It is, for all intents and purposes, permanent. And you know what? i've never been happier!

~sierra

I begged her for it

The last few weeks in my professional life have been quite stressful. Long hours, difficult work, seemingly impossible deadlines, and such. It's easy to get burnt out quick when your foot is to the floor. i'm not happy about it, a little ashamed actually, but this past Friday i safe worded to be released from chastity. Miss Scarlett was away on business, but understood, and promptly gave me the combination to the key safe.

She arrived home very early Saturday morning, and we had a long lovely chat. Saturday night there was plenty of playtime and i was put right back in sub-space. i received a spanking for some broken rules, and orders that were not followed while She was away. Then a generous amount of lidocaine was applied to my sissy clit, along with a condom to keep it all in place. 

Plenty of sex followed. i can't say i didn't enjoy it, any time inside Her is wonderful! However, because of the lido, i couldn't feel any of it. She had her orgasms, thanks to Her magic wand. Then i did something i wasn't expecting. i begged her to lock me back up. For the long haul... no erections, no orgasms, just the cage. "Until i break", was the phase i used. 

She told me to cum, and that i would be licking it all up. She told me to enjoy it because it'll be that last time in a very long time. i tried, and tried, and tried... but i couldn't feel anything. Then i asked if i could use her vibrator. That did the trick after a couple minutes! Still, if you've never experienced an orgasm with a completely numb penis, it's undeniably frustrating. You feel the contractions but that's about it. A full-on orgasm, but with none of the pleasure.

Needless to say, as i sit here and write this, i'm safely and securely once again locked. This time for who knows how long. My record? 125 days...

~sierra

2024

A new year! Yes i know, i'm like a month late to the party. Ya know, life and whatnot. Call it a new years resolution, or a vow, or whatever, but this year is going to be different.

This year, my goal, is to become a better submissive to my Wife/Mistress. Not that i was insubordinate before. This year i pledge myself fully to Her. i've never had more trust in Her than i do now. Our relationship is reaching new hights and we couldn't be happier. 

We're calling it the "year of submission". Kinda tacky, but it works. Our D/s relationship is slowly moving out of the bedroom, and into more of our every day life. i'm not really going to go into specifics right now in what exactly that means. Perhaps over the coming weeks/months i'll write about it. For now, my lovely readers, here's to a New Year, and a new life!

cheers
~sierra

FLM

i found the picture at the bottom of this post on another blog, submissive husband in Phoenix, in a wonderful post about submission, chastity, and FLM. You can read it yourself here. The article i thought was very acturate, at least in our (my Wife and i's) marriage. 

For us, She is in total control. i have accepted the fact that i will be in chastity at all times. Her pleasure ALWAYS comes first. my pleasure comes solely from Her. She decides when or IF the cage comes off. And any and ALL of my orgasms are Hers.

Once a submissive fully gives themselves to their Dominant, true happiness is achieved. my only concern is making sure my Wife and Mistress is happy. For if She is happy, then i am happy.

~sierra

That first step is the hardest

Well... i did it!!!! i can't believe it, but i did it. sierra, has made her public debut!

A few months ago, Mistress and i bought tickets to a show and a room away for the weekend. That weekend was a couple weeks ago. It had been the plan from the start that Scarlett and sierra would be going away. i was terrified when we booked the trip, but also unbeleivably excited. 

When someone says the "first step is the hardest", that couldn't have been more true. i was for real shaking. The entire time doing my makeup, getting dressed, and finally talking myself into actually taking that first step out of the hotel room door.

But you know what? i heard no comments (i'm sure there were out of earshot), i saw no reactions, and nothing negative happened at all. It honestly was no big deal. Honestly i felt the same way when i started shaving my legs and wearing shorts in "boy" mode. No one cares, no one pays you any attention. 

i wore a really cute red lace dress, short sleeve and knee length. Sheer black nylons and black flats (didn't want to be taller than i already am). The show was amazing, and we had so much fun! Being out as "one of the girls" was an experience i'll never forget, and one that i hope i get to live again. i've come a long way since i fist started crossdressing as a "dude in a dress", to a feminized sissy male, to dressing to "pass" or at least blend in.

~sierra