Sunday, December 30, 2012

sissy denial and begging Mistress for release

Yes, the twists and turns of my personal life continue. i apologize to those who perceive my recent posts as a delay tactic and are put off by my not delivering on a promised picture post.

There is no balance in my current situation. Too many problems, and too much pressure. One thing that i have delivered on is my promise of chastity until i session with Mistress. It's been over 3 weeks now without  masturbation. Another type of pressure is building daily. Some days i fight through the pressing biological need to cum without a lot of difficulty. This is not one of those days.

Mistress already knows that i will eventually submit to Her. my unheeded need for Her is what is ultimately out of balance right now. i have been inescapably caught in Her hypnotic and overpowering trap. Sadly for me, Mistress doesn't seem to be a big fan chastity, long term or otherwise. She gets more results from sessioning Her sissies to orgasm. It is a very, very effective way to condition a sissy and exert Her control. She has an expert's timing in delivering a lasting message at the height of Her subject's orgasm. And, She makes more money, of course. it is what She does for a living after all................

Sometimes chastity seems like a more humane alternative, at least for this sissy.  :o)

There is one escape though. Only Mistress Cassie can release me from my current state of frenzy, one way or the other. It may be denial, but i can ask:

Please, please Mistress Cassie. Please let me go, free me from Your feminization trap and Your control........

i am literally on my knees, begging.

sissy maid diane

Friday, December 28, 2012

Real feminization with a plastic reality

My feminization by Mistress Cassie is very real. So is the plastic reality that has defined my sexual identity while being trained by Mistress.

First the dildo & followed shortly after by the hard plastic.cock cage.

Now the plastic 'Fleshlight' pussy has gotten my attention as well as Mistress' attention. As She has commented, it's the closest i'll come to real Pussy now.

Finally, my ongoing obsession with Pussy has taken a turn towards plastic covered tease Pussy.


Yes, Mistress Cassie is for real. And so is plastic.

i haven't seen Mistress on line the last couple of days, but i have sissy tan lines, and it won't take long to get dressed when i first IM with Her. Then the phone session. It could happen tonight, maybe tomorrow, but soon in any event.

And it will all be documented here - with pictures.

sissy maid diane

Thursday, December 27, 2012

The perils of wearing a girdle daily

my long time obsession with the girdle has led to Mistress Cassie mandated girdle training. At the time, it seemed easy enough, even exciting. After all my panty training by Mistress was quickly and painlessly implemented (permanently).

Girdles are another matter though. A control garment by design, they can be very uncomfortable. i don't know how Women do it on a regular basis. i've been wearing open bottom girdles when i can, but i have a limited supply of that style in the required colors.

On the other hand, my large collection panty girdles simply make me sore on most days. They aren't designed for sissy genitalia, as the lovely model Tori demonstrates in these caps.

Hopefully this training will be more like conditioning for regular wearing that doesn't necessarily mean every day. Like with so much of my training after a while i need the things i'm trained for.


i need to pee sitting down
i need to cage after masturbation
i need to keep my body hair shaved

All of these things are needs that have been trained into me by Mistress. But i don't pee, cage or shave for hours every day.

There's no doubt now that i have spent a lot more time girdled during the last 2 weeks than most 6 month periods in the past. It's obvious to me that i will need to adorn a girdle much more frequently moving forward, and will abide by the color schedule when that need arises.

Hopefully Mistress will show some mercy here and not require daily girdle wear in the future. i'll find out soon enough. There is another pressing need now. The need for a phone session with Mistress.

sissy maid diane

Property of Mistress Cassie

One of the themes in my upcoming picture post will be "property of Mistress Cassie". i have added something else to my toy box. It could be called a prop, but it's symbolism is real. It requires locks.  :o)

i have been enslaved.

sissy maid diane

It's session time with Mistress Cassie

It's long overdue and nearly here, a phone session with Mistress Cassie. i'm in a girdle now & will be all day.
This evening i'll be freshly shaved with new nail polish on, completely dressed and will be showing off my new sissy tan lines. i'l be showing off Mistress Cassie's femming handiwork period, with a picture post.

Once Mistress is on line, i will IM with Her and then submit to a phone training session. It may not be tonight, but will be as soon a She is available.

i've been in chastity for weeks now and the frenzy has reached a breaking point. All i think about is pussy, my pussification, having one, the plastic pussy. It's consuming me now.

To emphasize my condition, here's three inspirational and influential photos of the mesmerizing Lola: In a loving caption series.

Lola is the latest addition to Mistrress Cassie's feminzation heirarchy.Yes, i'm finally ready for Mistress now.

sissy maid diane

Sunday, December 23, 2012

More sissy pussification

Panties look so much more appealing when there's no 'bulge' down there. They lay so smoothly. So pretty....

sissy maid diane

Saturday, December 22, 2012

sissy transformation in progress

It's been over two weeks now without cumming. That's a lifetime for me and the need grows. The need for orgasm, Mistress Cassie and more pussification.

sissy maid diane

The bulge in the girdle

One of the problems with wearing a girdle every day, is that unsightly bulge between my shaved legs. It's still there though ........ for now.

sissy maid diane

Thursday, December 20, 2012

sissy cuckold caption

This is a pre scheduled post. i'll be back in town late on 12-20-12 and the girdle training will start in earnest then. It won't be long until a session with Mistress Cassie follows - trust me.

Meanwhile, here's a pic that got my attention. Maybe it's the dark hair - like Mistress. Whatever the reason, the very sexy Aletta (and mystery friends) inspired this cuckold caption.

Back soon.....

sissy maid diane

Wednesday, December 19, 2012

Girdles, chastity & sissy tanlines - oh my!

                            Nothing says 'feminized sissy' like tan lines

i have been a chaste sissy since Mistress Cassie posted on my blog last week about girdle training. i spent several hours 'girdled' today & masturbation seemed imminent (and was needed). Then Mistress left a comment today & i decided that chastity until my next session with Her was in order. After all, while i haven't masturbated since last Wednesday (this is day 6), i also haven't starting my girdle training in earnest. i am out of town, and will be back on Thursday evening. By this weekend i will have shaved and will do a dress up girdle post for Mistress.

It won't take long after that and i will be calling Mistress for my first session with Her since January  i will be in a girdle and chastity frenzy, very much in need of Mistress.

So, while i'm at it - nothing says 'feminized sissy' like tan lines. i've done it once with cream. It is the  equivalent of a sissy 'tramp stamp'. Or 'property of Mistress Cassie".

Back when i had lines for a bit, they were a constant reminder of my sissy state and of Mistress. So, there will be cream involved again, it just came today.It's a better quality than what i used in my last attempt to tan.

So real sissy girdle training starts this weekend. Chastity is well underway. Posts, tan lines and the long awaited session to follow.

sissy maid diane

Tuesday, December 18, 2012

So many panty choices........

Well, i recently purchased 5 new pairs of Vanity Fair panties on line @

These panties are wonderful! When they arrived, i didn't bother to keep my existing panties on, there will be no returning the panties.

i also really liked the image of 6 pair of panties on a Model. Nice. Since i now own in excess of 300 pairs, this image really struck a chord with me.

But these panties are so silky, all nylon:

In other new, my girdle training will begin in earnest soon. When i get the opportunity to do it right, which will include a fresh shave & dress up shoot to get things started. In any event, i will get it done by years' end.

sissy maid diane

Friday, December 14, 2012

The fear of fleshlight training

Without exaggerating (or extensive analysis), i've probably masturbated somewhere in the neighborhood of 15,000 times since puberty. I'd say that about 99.9% of these events involved wearing panties. Yes, i masturbated early & often, wearing panties. Usually a slip was involved as well. i love the feel slippery feel of nylon on nylon. Long before i was panty trained and feminized by Mistress Cassie. Until Her training took hold, i always took the panties (and other lingerie) off, as quickly as i came. i was horrified by my obsession and need to Female underwear. Now, of course, i embrace that need.

So, another masturbation factoid. Out of the thousands of masturbation events i have cum exactly 0 (ZERO) times using a masturbator. It's not like i haven't own a few. i still have two supposedly 'pussy like' sleeves that have never been cum into. i also have a pump, a suction tube with vibration. i tried feverishly to cum into that thing. No dice. i've also tried repeatedly to cum in the cock cage while wearing it. Talk about futility.

There have been other unsuccessful toy purchases along the way. Other masturbators. NADA. ZILCH.

Then - along comes the Fleshlight. i ordered it several months ago and after lubing it up i was instantly aroused, and entered the 'flesh'. i knew right away that this one had REAL potential! i believe the manufacturer's claim that it is the #1 selling sex toy of all time. Yet i didn't cum and didn't try to, because i felt that Mistress needed to be involved. i obsessed about it for a while, posted about it, and planned on a session with Mistress Cassie.

Instead it's hidden it now under my bed in fear. Fear that She will get me to cum into and fear of the implications.

Mistress has forever weaned me from real Pussy.

 She has trained me to enter the hard unforgiving plastic of the cock cage every time i masturbate. EVERY time. i'm cage trained. A non stop theme of Her training from day one was the cock cage. Just like my 'pre Mistress' panties, i owned a cock cage. And just like the panties, i lost interest in it after masturbating. It was exciting to think about, but actually putting in on after masturbation just wasn't going to happen.

Mistress certainly broke down that wall with ease, in the first phone session. Now, i there's the frightening thought of the Fleshlight. i suspect that Mistress could session me into a fleshlight cum. There's no reason to think She can't. But after all these years of never cumming into a masturbation device? omg!

Between the denial of real Pussy, the plastic cock cage prison and now maybe the plastic pussy?  Talk about pussification.

So, we'll see. This is the second of the 'fear' series of posts. And, the second of the 'be careful what you wish for' posts. Will Mistress girdle train me? Will Mistress get me to cum into the fleshlight plastic pussy. Will She  fleshlight train me? Oh, my!

Stay tuned.

The hobble skirt & high heel 'fear' post is up next.

sissy maid diane

Thursday, December 13, 2012

Girdle Schedule

Hello diane,

I have a little present for you.  I know you love schedules, so I took a few minutes and  drew up this schedule for you.   I am sure you will eventually get used to it.  lol

Monday -  Yellow
Tuesday  - Green
Wednesday - Blue
Thursday - Purple
Friday -  Pink
Saturday - Red
Sunday - White

A rainbow of girdle training for sissy maid  diane.  How  perfect.       Feel free to experiment in  patterns,  florals, stripes, polka dots... you get the idea I am sure!      I want My sissy to feel completely controlled,  trapped and  held tight!

Talk to you soon,   diane.

Mistress Cassie

The fear of girdle training

Girdles are an article of Women's undergarments - a control garment. Since my youth, when i cherished upskirt glimpses of Female school mates girdles, they have been instrumental in sending me on a long journey form cross dressing to feminization.

i have posted many times about girdles & i have an extensive collection. Mistress Cassie introduced me to open bottom girdles and has 'girdled' me on an occasion or two.

i still have a preference for long line panty girdles, but are all girdles are wonderful. As long as they have garters. Nylons are a mandatory accessory when this sissy is girdled.

While Mistress has girdled me before, i don't actually consider myself girdled trained. Conditioned?  Influenced greatly by this Garment? Absolutely! But girdle training remains basically unexploited by Mistress. Such training is a fearsome thought indeed.

Back in 2007, when Mistress first panty trained me, i already owned quite a few pairs of panties, including a set of nylon & lace trimmed Day of the Week panties. She put me into the 7 day cycle of DOTW panties and soon after i was trained. Now, i own hundreds of pairs of panties & 0 pairs of 'boy' underwear. Mistress also has be panty color scheduled me and i have since bought a set of coordinated DOTW "Property of Mistress Cassie" panties. my absolute favs. Shimmering nylon with frilly lace trim. mmmmmm

Sunday - White Panties

Monday Purple Panties

Tuesday - Blue Pantiies

WednesdayYellow Panties

Thursday - Pink Panties

Friday - Green Panties

Saturday - Red Panties

O, wait. We're talking girdles here.  :o)

i own girdles in all of these colors and more. Mistress could easily, on a whim, put me in girdle every day,  just like the school girls used to wear them. i'm still in sissy school after all. She could easily put me on a girdle schedule. She could easily girdle train me. The next phone session maybe.

This is the first of 3 'sissy fear' posts, that are clearly starting to look like 'be careful what you wish for' posts. Scary, but i can't help it.

Like the fly caught in the Spider's web, the more i struggle to free myself, the more hopeless my plight.

sissy maid diane

Wednesday, December 12, 2012

sissy fear - fear of girdles, masturbators, hobbling & Mistress Cassie

Living in fear can be a terrible thing. i fear Mistress Cassie and the hold that She has on me. She has panty trained me, toilet trained me, cock cage trained me, and has done it all without a slave contract. She has told me (correctly) that She simply doesn't need a contract to enslaves and feminize sissies.

She can post a panty color schedule on a whim & i now wear those ordained colors for Her every day. It's a contract of sorts, but it doesn't need to be a signed document. It's a done deal.

i pee sitting down now, no contract. i have to factor in a minimum of 4 hours in the cock cage every time i masturbate, no contract.

i am in fact, a Mistress Cassie trained sissy - period. Such is Her Power over me.

So, these three things are a 'trained' given (and there are more - (shaving, painting nails, etc) which is why i live in fear of Her. These three things though epitomize what i am really vulnerable to with Her. And that would be 'task specific training'.

Currently i can think of at least three more things that i would fear training of by Mistress. It's one reason that i've been holding out on a phone session.

1) Girdle training

2) The fleshlight

3) Being 'hobbled' by the hobble skirt & locked heels

Why such blinding fear? Instead of a series of girdle posts, i will be posting 3 times about these three little fears. the first will be about current training fear #1 - girdle training.

Tonight though, i'm trying not to think about what the future holds for me. The inevitable phone session with Mistress looms large now. And there will be repercussions for me waiting so long.

It's a fearsome situation!

sissy maid diane

Girdles for men

i think this will be the first in a series of posts about girdles. For those who are not a girdle fan, i apologize in advance.

The fact is, i'm in something of a 'girdle frenzy' right now - again. Yes. i've posted about girdles numerous times. It goes back to puberty for me where girdles are concerned. Like the Mistress Cassie feminization trap i'm caught up in, the girdle influence simply isn't going away.

So, what about this frenzy? Well, for starters, due to personal & professional 'issues' this year, i have bought very few new gurly things in 2012. That is until 2 very affordable girdles in the last couple of weeks. More about that later, but let's just say that this post from yesterday is related:

It's complicated (as usual), but if you watch & listen to the video, there is some noticeable 'swishing' going on as She disrobes. Oh that wonderful skirt over nylons sound! Well, let's just say that my new  girdles have a certain 'swish' about them.

So, more to come, maybe even a video w/ sound, my new girdle sound while i walk in heels.

For now, this ad from what looks like my puberty era got my attention in more ways than one. The wording is interesting. Like "Choose Kayser for men". Girdles very much attracted me as a young 'man', but i don't really equate them an attractant per say for the average man, especially these days.

But, read the ad - it's interesting. From a different era for sure, and for me - cage worthy.

All these years later.

sissy maid diane

Guest caging cap

Here's a fun one from

i like Her.

sissy maid diane

Transvestite party

One of the things i enjoy monitoring on my blog is web searches. my blog gets hits from a lot of searches with key words like "feminized sissy", "panty slave", "girdle trained", etc. i usually see search images. i am frequently in them, and i also frequently see images that appeal to me.

Like this one:

It came up with the key words "transvestites sucking cock". Nice. It looks like great fun! And, there appears to be a cock or two available. :o)

sissy maid diane

The never ending cycle of Female Dominants

There is always a new generation of Female dominants from a sissy's perspective. In fact, every year there is another crop as young Women come of legal age. Women are inherently dominant of sissies. Here's a few samples of the new generation, in caption form.

As dominated as i am by Mistress Cassie today, if i was 40 years younger these days, i'd be in real trouble! i'm securely under Mistress' thumb for sure, but She's a professional sissy trainer. It could be much worse. :o)

i could be dominated by an amateur teen. Oh, my!

sissy maid diane