The sissification begins in earnest

i've mentioned 2008 as the real beginning of my feminization. That was the year, in May that i had my first phone session with Mistress Cassie. i also mentioned the year 2003. That was the year that i first encountered Her on line. Back then, Mistress had a website, which is now a blog: http://www.sissysalon.com

The website was something i followed with sissy horror and fear starting in 2003. mistress Cassie handed out sissy assignments, horrible assignments. One that i remember well was 'show some lace'. A closet croess dresser for years. i couldn't imagine being out in public 'showing some lace'. Forget about actually going 'out' in public, just showing lace was too much for me to contemplate. Mistress had sissies actually do it & post about the experience of Her website. i was, at the time, in another long term relationship, 2 years running. It was with a much younger Woman and She knew about my cross dressing & even participated to some extent. i should have been content.

But i kept going back to Mistress Casssie's site for 5 years. i was lurking, in awe of this Internet Presence, but never participated. She was becoming am obsession & seemed to offer what was missing in all of relationships with Women, including t3 marriages, a live in partner & an ongoing affair. i had an irresistible, compelling inner need to be dominated by a Female, a need for feminization. During the period of 2003-2008 i had incredible real like experiences in that LTR, including two instances when i dressed and submitted to a strap on.

A seemingly perfect scenario, but something was still missing. The domination i was receiving in real life was occasional role play. i ca to knowhe real meaning of Female domination starting in 2008. On line, on the phone? Yes. Real - YES. i am jumping ahead a bit, but in 2008 Mistress Cassie 'Queen Bee'd' the 7 year old  relationship out the door. She took over, completely.

Much more about that to come.

Tonight a reflection on 2003, the beginning of the remarkable web that Mistress wove to trap a sissy, a life time cross dresser who managed to keep it all largely inside, in a closet, and in denial. i had been denying my true inner self for all of those years. Eventually Mistress Cassie opened the door and i walked in. The door is closed & locked now. i am sissy maid diane, living in Mistress Cassie's world, on Her side of the door & She has the only key.

Mistress Cassie has never lost control, but She has allowed me to take a break to deal with some life issues. Soon i'll be dealing with adding new content to my blog restructuring efforts. Content to be determined by my Mistress. i am currently comfortable resting against Her breast. She will soon draw me back in and i will be suckled once again. Eagerly drinking in Her persistent, undeniable Authority.

Next, a look at some of my sissy toys. Soon, more about the Mistress/ sissy relationship & there will be new pictures. Pictures to be taken after my next phone session with Mistress.

sissy maid diane

frilly sissy petticoats

i have been fascinated by petticoats for some time. Just the frilly sissy appearance alone makes my heart go pittypat. For whatever reason though i was late in actually wearing one. It belonged to my last wife, and wasn't full, but it was a petticoat. Black and stiny with white trim. After that divorce in 1997, i exercised that wonder of an an online purchase & bought a couple of petti's. Too much organza & stuff going on to substitute for a slip over panties with the goal of sissy masturbation. But i instinctively knew right away it was a feminizing garment. So frilly! i own lots of petticoats now, and took lots of pictures for Mistress while wearing them.

When i transformed my bedroom into a sissy gurl's room last year, my closet became 100% sissy. The petti's are a daily reminnder of how much Mistress Cassie's training has transformed who i really am.

Not that long ago, petti's were an exciting curiosity. Now, they dominate my closet with their number, different colors, fullness, and frilliness. Every day when i open my closet, they scream - you are such a sissy!

And i am.

sissy maid diane

sissy high heels

What goes better with nylon stockings than high heels? Nothing! High heels really aren't natural. Extreme high heels are very unnatural. They are uncomfortable, hard to wear for any length of time, hard to walk in period. i personally prefer looking at Women in very high heels. Heels accentuate a Woman's legs, especially the calfs. They are very, very sexy. i think Women wear these wonderful, uncomfortable shoes knowing that the legs are shown off. High heels attract men, and they also attract sissies.

i like everything about high heels, even the discomfort. A small price to pay. They are so, so Female. i can wear panties all day, every day (and i do), but it can be my little secret most of the time. There's simply no hiding high heels, or their effect.

i often find myself walking around on the balls of my feet when i'm not in heels. A constant reminder of how much time i've spent in them. A lot of hours in heels, high heels, 5" or more high. i bought my first pair years ago and hid them like a squirrel buries an acorn. They came out of hiding for brief periods, when i would really feel the urge to dress. They didn't stay on long back then. Like panties, slips, girdles, stockings and bras, it was masturbation wear before Mistress Cassie. On went my gurly things, out came the cum, off went the gurly things.

Yes, those days are forever gone. i own lots of heels now, more than most Women, i think. i belong in high heels now. No, i don't wear them for a few minutes, masturbate, then quickly take them off & hide them. i wear them often now, enjoy them , and don't associate masturbation with wearing high heels. i am simply a girl who enjoys wearing high heels. i have learned to embrace and celebrate my feminization. i am trained.

These are the days of diane, sisssy diane, trained by Mistress Cassie to feel at home in heels, in lingerie, to miss it all when i'm not dressed as a gurl. i am Mistress Cassie's sissy girl diane.

Next up, petticoats. Soon i'll get into an overview of my massive collection of sissy things, including toys. Then, i'll address the Mistress Cassie Era, which started in earnest in 2008 - but has roots going back to 2003..

sissy maid diane

sissification and stockings, a short history

Stockings are another of the world's all time great creations. Featured in many of the ads i came to lovee in my youth, the girdles i viewed in school had garters, and the garters were attached to stockings. Great combination. i remember a magazine ad from the 60's that featured a lovely Woman sitting in a chair with Her legs crossed. The message of the ad was that the era of pantyhose was at hand. The Model was showing garters and stocking tops. Unsightly?? No, it was an image that drew a LOT of cum out of me. i have spent countless hours searching for that vintage ad, to no avail. If i ever found it, i would recognize it immediately. That image is forever burned into my memory. Pantyhose are fine & i own lots of pairs now. But stockings and garters - whether from a girdle, bustier or garter belt simply rule!

When i was just starting high school, right before my growth spurt, i used to catch the school bus at an elementary school a few blocks from home. In the winter, the bad neighborhood Girls would sit on the gym stage with Their legs crossed, giving gawkers like me quite a show. my favorite magazine ad came to life. i love the winter still. Back then, those Girls were regarded as sluts. me, well i likened Them to Goddesses. How ironic that i would eventually become a slut myself, a sissy slut.

my first real life appreciation of stockings came later on, when i first felt the silky legs of a young Woman in nylons. i got a much deeper appreciation of the wonder of nylon stockings decades later, in 2008. When Mistress had me shave my legs and i slipped on nylons over my smooth legs, it all finally came full circle for me. There will be much more about the Mistress Cassie influence to come, but for today, a tribute to nylon stockings.

Here are a couple of pics that are old blog pics of me, shaved, in nylons - a sissy slut properly trained by Mistress Cassie.

Next - high heels. They go on so much easier when nylons are on.

sissy maid diane

sissy's bra story



The bra, what a wonderful invention! It encases a Woman's breasts and can play a big role in encasing a sissy. Unlike panties, girdles and slips, the bra was not a central figure in my early crossdrsesing days. The magazine pictures were just as fascinating, but i didn't start to really appreciate bras until high school. Like a lot of teenage boys, i was guilty of awkward groping when i finally got some private time with a Girl. The feel of a bra covering breasts was a real eye opener. It was probably 50-50 on what i found more exciting - the bra, or what was on the other side.



As i got older and was priviledged to encounter more bras & breasts, it actually came to my attention that The Female might not have the same appreciation of a 'good feel' that i did. It wasn't until recently that i came to understand that response. More about that later.



Let's just say that after relationships turned to marriage, i didn't raid the bra drawer much, if at all. When my femming started in earnest in 2008, i can remember buying a powder blue bra (still one of my favs) with formed, padded cups. i was very, very excited and told Mistress as much. Yes, i added LOT of bras to my rather lame collection after the Mistress Cassie influence started to take hold. Before that, i had several, but filled them with foam inserts, if anything. A little over a year ago, i discovered silicone. Oh, my. That's when i really started enjoying feeling myself up, and feeling my blooming femininity.



But, i'm jumping ahead. i still have a strong attraction to pictures of Women in lingerie, including what i would call 'soft porn'.  Even hard core porn sets often start ou with The Woman wearing lingeries, a tease of sorts. So, here are some more recent pics that i love of Women in bras and a few of me.

There has been a development recently related to bras - a new purchase. i'll share that in new pictures once i've rebuilt something of a blog. And when i'm ready for the next phase of femming by Mistress Cassie. That will inevitably come, soon enough.

sissy maid diane



sissy slip love

Along with girdles and panties, my love of slips goes back to puberty. Slips and panties go together deliciously. Nylon on nylon. mmmmmm.........

Wearing a full slip for the first time as a boy, i appreciated the similarity to a dress, and the material was just heavenly. my first brush with possible cross dressing humiliation came in my sister's bedroom, just after donning her red skip. Fortunately, i had kust covered up with a robe seconds before she entered the room, her room. i had some explaining to do, but at least the embarrassment of caught wearing the slip was avoided.

It would be years before i bought my own red slip - in the late 1990's. It was a used slip i bought on line from a slip site. i had purchased pictures of the original owner wearing it. Then i bought the slip itself. It's still one of my favorites with lots of lace. The fact that it once belonged to a Woman makes it even more special. Now i own lots of slips of all lenghths and colors.

Yes, this sissy loves slips.

sissy maid diane

Panty love - a sissy's new perspective, courtesy of serving Mistress

So, it all started at puberty years ago. While i rebuild my sissy blog it's already apparent to me that i have a different perspective than i did when i started my 2008 blog. Three years of being feminized by Mistress Cassie has changed a lot of things for me. While being feminized, i was and still am serving Her interests. Mistress is in control, my role is one of sissy servitude. It is a mutually rewarding relationship.

It has dawned on me that i made a fundamental and recurring error in judgement in previous relationships with Women. Back to my teenage years, when the die was cast and i became a lifetime cross dresser. my addiction to lingerie was driven home by the feel good results of masturbation. When girls first started noticing me in High School, after my growth spurt, i graduated from magazines to the real thing. Girls!

The only problem was that i quickly fell 'in love' with what They were, not Who they were. i simply love Females, period. But falling 'in love' with the feel of real Female breasts in a bra, or a real, soft Female bottom in panties is not love. Women feel good, they are soft and pretty. They smell good, and they are silky smooth. And - They all come with Their own wardrobe!!! That alone does not make for a successful relationship, as it turns out. A lesson i learned over & over again. Until i finally met the right Woman, on line. Mistress Cassie. She has taught me more about Women and myself than i learned from all of my previous relationships with Women - combined. That will be the tone of this new blog, the new diane, the new me.

Before getting to the details of the last 3 years of my femming by Mistress, (and what comes next) here's some more of what led up to my current state

After getting regular peeks at girdles in school and discovering masturbation, it was panties that became the object of my desire. No other Female garment was, or is more important to me. During puberty, getting an up skirt peek at girdles was exciting stuff for sure. Looking at pictures of Women in girdles after such peeks given by school Girls and then cumming is where it all started. But girdles are not masturbation wear. Panties are. For years, even after i married for the first time at 19, i masturbated with borrowed panties. Now, of course i am 100% panty trained and have a huge collection of panties that i can happily call my own.

Interesting ,(i think), i never really had many up skirt peeks at panties. It was girdles mainly. But panties are the mainstay article of clothing that has really influence me the most. Of the thousand of times i've masturbated in my life, i would say that i was wearing panties for 99.9% of those events. Panties rule!

Next up - slip love.

sissy maid diane.

The sissy's feminization journey

This is a recap of my feminization, from the beginning. i'll be recapturing some of my past posts and work towards actively reentering the world of femming, femming by Mistress Cassie. This new blog is the first step in getting back up to speed. i'm not ready for a feminization phone session with Mistress. my last phone session with Her was a 'life' issues session. You see, Mistress Cassie is much more than my online Trainer. She is also my counselor in life matters. Such is the depth of the this Mistress/ sissy relationship. Her influence and control runs deep - as do my sissy roots.

i am not a young sissy. Thank goodness for make up! When i was approaching puberty (in the 60's) i became fascinated by Women's periodicals that i found around the house. Specifically magazines like Redbook and Ladies Home Journal. The lingerie ads in particular caught my fancy. In those days,. girdles and stockings were the norm. The lingerie ads were wondrous to me. Lovely young Women wearing all sorts of pretty lingerie. Store catalogs like Sears and JC Penny were also readily available at home. They had pages upon pages of lingerie for sale with accompanying pictures, of course.

While i was discovering this treasure trove of delights, adolescence was setting in, puberty was making itself felt. It was time to experience masturbation. A popular topic amongst my male classmates. As it was, there was also access to panties, slips girdles and other goodies in the house. my first masturbation event found me in panties with a Sears catalog in one hand, my pantyclad cock in the other. The die was cast.

Back then, i was just about the smallest guy in school. This was another factor in the grand scheme of things. The Girls naturally prefered the company of the bigger guys. So, in Junior High School, i was basically on the sidelines, watching the Girls with growing fascination and admiration. my goodness, they put on a show, even back then. Before the Feminist movement gained prominence, even young Girls still wore girdles, stockings and skirts/ dresses. It was normal every day school wear for them. And every day i was treated to upskirts that made the pages of magazines and catalogs real.

i masturbated frequently, never without panties on and usually with a borrowed slip and or girdle involved. The cross dressing hook was set very deep, very early for me. i experienced a growth spurt when i was 16 growing 10 inches in less than a year. Girls were suddenly attainable. In every relationship since then, my lingerie addiction played a role in one way or the other.

More on that later, but for today, a tribute to girdles. i saw lots of them when i was young. In ads, in school, in what should have been forbidden lingerie drawers. Now i have about 3 drawers full of my own girdles. Here are some pictures of an ad or two and of me, from a while ago. From the other blog.

sissy maid diane

sissy blogging Part 2 - starting over

Yes, it's me - sissy maid diane (formerly @ maiddiane.blogspot.com). i started a sissy blog in July 2008 as an assignment from Mistress Cassie. Last month it was disabled by Google. i'm not sure why, but it's a free service and getting it reinstated seems unlikely. i've tried. i'll be more careful this time around and the external sources content will be a little more judiciously chosen.

So, it's time to start another one. i'm still a sissy after all. And, i'm still very much under the the spell of my Amazing Mistress. i may not be posting a lot for a while as last month brought in other changes in my life. i have a new career, which has been a big adjustment - in positive ways.

For today, i'm reaching out to start recapturing my audience. Here are a couple of my favorite pictures from the old blog. There has been a lot of femming going on here since 2008. i still have a lot of the pictures. More importantly, i have retained the massive amount of training i've had from Mistress. i have been lucky to experience so many wonderful things that usually are for Women only. And only a Woman like Mistress Cassie could have pulled it off. i am forever changed by Her, for the better.

Yes, there will be more to come.

sissy maid diane