Sunday, April 13, 2014

Released from caging, i now pay for masturbation privelidges

Mistress Cassie has long ago conditioned & trained me to masturbate on Her terms. Every time i masturbate i cage for a minmum of 4 hours, much more at times - especially after a phone session with Mistress.

News flash - after 7 years of being trained to wear a cock cage after every time i masturbate, i have been released from the arrangment. The cage is no more. In it's place is a new arrangement with Mistress Cassie. Now i must pay Her every time i masturbate, not just for phone sessions. i have set up an account at Niteflirt & will be held accountable for any future masturbation event.

When the fee is paid to Her, She will know what it's for. And that is exactly what is so wickedly appealing about it to a sissy like me. Heretofor,Mistress didn't know when i masturbated. She knew that i did it in a way that furhetred my feminization, but there was no other accountability beyond the caging and training. Now She gets a payment every time i get a little more feminized in what used to be private.

Any sissy will know how exciting this prospect is, true control of my masturbation habits for sure. Controlled by a Domainat, Beautiful Woman. Any sissy who wants to experience the same level of control, just needs to set up an account at Niteflirt and start paying a masturbation fee to Mistress. The link is at the top right of my blog. In any event. i'll be doing it!

And the femming continues.....

sissy maid diane

Saturday, April 12, 2014

Battling the 50's and Mistress Cassie's hold

i am a porduct of the 50's, one of the great era's in American history. The clothes and lingerie that Women wore into the 60's was the best ever, in my opinion. While i was growing into puberety in the early sixties, this era was still alive and well. And, that cloting left an indelible impression on me. Girdles, stocking, petticoats - oh, my!

So i bought a (made for a petticoat) polka dot 50's style dress in January. It \just so happens that i have a day as a 50's Woman assignment from Mistress Cassie that is way overdue. Yes, i had the dress and girdle, petticoat, etc. on last night. But, i am battling against the urge to put it on again. Becuase the next time it will be as part of my 24 hours as a 50s housewife. Ptrobably as my 'welcoming hunny home from work attire.

Like all battles with feminization and Mistress Cassie the outcome is preordained. Mistress simply never loses! She's posted here about this and just a whisper from Her now and i'll capitulate. She didn't put a deadline on the assignment, so i'm still holding out. But, i'm running out of time in any event.

The urge grows strong........

sissy maid diane

A sissy gets spanked

Yes, i have been away for awhile, and yes, i'm struggling. i'm struggling with behaivior isssues and i'm in pretty intensive therapy. It's a struggle allright, changing lifetime behaivior patterns like cross dressing. The funny thing is i'm making progress. Anyone who follows this blog jknows that i can be over the top at times (to say the least) obsessively posting in copious amounts. And, i do things like marry an online Mistress, Mistress Cassie.

i have had no contact with Her since January, and i've not looked at the blog at all until today. i even donated the wedding dress to a non profit organization. Also, i dontaed a bag full of sissy cothing. Now that's progress.

So, why is it such a struggle, and who's winning?  Mistress Cassie has emplored me for years to try and attain some balance in my life. Balance between work and personal life, and balance in my sissy diane life. She knew what io didn't - my carerer is over. i was into work so much that i lost my way and basically my mind. But is ignoring Mistress Cassie and diane's needs altogether the correct path for balance? Maybe not.

i'm not promising a return to the old diane and my past blogging ways, but here's a post. When i did look at the blog, i saw Mistress Cassie's post. She correctly pointed out two things.

One - i need to be spanked by Her
Two - there is an outstanding sissy assignment, given in January that is overdue. i am to spend 24 hours as a 50's housewife and post with pictures.

The spanking will come, in one way or another. Who's winning this struggle? Mistress Cassie, of course. The wedding dress may be gone, but the vows are not. i'm still very much Her sissy bride, still hopelessly caught in Her feminization trap.

i have my 50's dress on now, along with a petticoat, girdle, stockings, bra, panties, heels, and camisole. i'm holding out on the make up, hair, pictures and posting. i'm holding out on the assinment, still struggling with it all.

But, at the end of the day, i realize that this struggle is counter productive to my recovery. Mistress Cassie is not going away, and She dosen't give divorces from sissies. She will not let a trained and trapped sissy escape. It's not Her nature.

And it is my nature to submit to Her. It is also my responsibilty to find balance in my life, not Hers. She's waiting for the inevitable as i suspect my reader's are.

For now, the struggle continuses, but this is a step back towards feminization and back into Mistress Cassie's world.

sissy maid diane

Thursday, March 27, 2014

A spanking for a sissy bride

well  diane,     have you prepared yourself for your full day as a real 50's woman?

you wouldn't want to be spanked now, would you.  ( probably you would)


Mistress Cassie

Monday, January 20, 2014

'Head'ed in the right direction

Mandy is a lovely Woman for sure, and She knows how to please a man.

Here She has got him to come - next that cock needs to go back in Her mouth . Just one sissy gurl's opinion................

sissy maid diane

Analysis of proper deep throating

Now this cock has been properly seated, deep into the sissy's throat. X-ray's don't lie. A nice big load is sure to follow - as it should be..........

sissy maid diane

Swallowing preferred

Yes, She's done a fine job here. But what about swallowing! Many porn pics and vids like to sahoe the man cumming - that makes it real. But as a sissy gurl, i think the real reward of a blow job is the load down the throat!

sissy maid diane

Modern day lingerie ads

While i'll always have a special soft spot for 1950's and 1960's lingerie ads, newer ones are inspiring as well.


All it took was a quick search to come up with a few Models who are really paying tribute to timeless lingerie essentials, just in a more modern way. It seems that garters and stockings never go out of style. Thank goodness!!

sissy maid diane

And into a girdle i go...........


i've looked at so may girdles of late, that i found myself wearing one today. A blue long line girdle, in fact.

sissy maid diane

Classic Lingerie ads

sissy maid diane

Sunday, January 19, 2014

More vintage lingerie ads

Just preparing myself for the upcoming 50's assignment.  :o)

sissy maid diane

Blow job practice

Girls having fun and learning at the same time.

sissy maid diane

Girdle ads and eye contact

Lingerie ads and especially girdle ads got my attention and were a big influence on me during puberty. Whether it was in Women's magazines or the lingerie catalogs from major retailers, it was the closest i could get to porn at that age.

Many of the ads featured Women in demure poses without eye contact. The lingerie, the Model's figure and femininity were nicely on display.

But what really got my attention was the ads with Model's that made eye contact with the camera. That made it much more personal.

i didn't know it at the time, but these lovely Women were feminizing me at an early age. Every time i  masturbated to these images, i was drawn further down the cross dressing road, and ultimately towards being a submissive sissy. Yes, the die was cast at an early age..............
sissy maid diane

What to do for a 50's dress?

Hmmm, i need something appropriate for being a Female all day, a 50's housewife dress. Something that will accommodate on of my many petticoats.

What to do????

Problem solved & on the way!

sissy maid diane

Saturday, January 18, 2014

There's no hiding the femininity of a petticoat

A sissy can wear all shorts of girly underthings undetected, and still feel oh so feminine. Panties, bras, garter belts, girdles, stockings, and camisoles.

But one of the most feminine of items of all was very popular in the 1950's - the petticoat. There's no hiding this, either the garment or the sheer girliness of it.

When i've completed my '24 hours as a Woman' assignment i will have a new appreciation of this garment for sure. i'll be a 50's housewife after all. Back then, a petticoat was required wearing fgor girly girls.

sissy maid diane


When a sissy becomes a 50's housewife

Not only am i going to spend 24 hours as a Female, it will be as a 50's housewife. i'm expecting that it will require a lot of effort. It wasn't easy being a 50's housewife, i think. Lot's of expectations, and like today, a lot of work just being Female. Back then, The chores, the hair, the dress, the apron, the girdles, stocking heels, nylons,  - while at home!


 What scares me is that i will find, and get trapped in, the prefect role for sissy diane. Oh, my!!!


sissy maid diane

The 50's Housewife & discipline

While i (probably) won't have a 'husband' coming home on my assignment day, 50's Housewives did. And after a hard day's work, he better come home to a clean house & properly prepared hot meal. Or else............

Even the Iconic Actress & Comedienne Lucille Ball got turned over Desi's knee - on national television! If i don't get this assignment right, i expect Mistress Cassie to mete out a similar punishment.

At least the husband had the decency to wear a tie, after the Housewife spent the day in heels and a dress!

Now, of course, the husband is more likely to receive the spanking. Oh, yes - things have changed! But not for me, i am a sissy bride forever linked to the 50's & 60's - and to Mistress Cassie.

sissy maid diane

Preparing for the latest assignment - the 50's housewife

i am a product of the 50's - a baby boomer.Ah, those were the days! Not necessarily for the housewife though. She was required to wear many hats, much like today's 'House' Woman, with a very big difference. Today's stay at home Wife is much, much more liberated. Rather than being a virtual servant to the husband and kids, today the Woman is at least an equal partner in the relationship - or should be!

Ah, but this post & the upcoming assignment will be a tribute to the 50's Housewife. my recollections will be on display, and i am preparing myself for the inevitable surprises that will accompany my being a Woman for 24 hours. It seems a logical choice given my recent sissy 'marriage' to Mistress Cassie.

Among other things there will be housework and cooking. Also, i'll change my TV viewing habits and many other habits that day. It will all be documented, including pictures.

One of the things i find fascinating - and exciting - is the clothing worn by Women of that era. There are many images of Women wearing heels & a dress in the 50's while doing housework. Oh, my - it's a good thing that i have plenty of gurly undergarments that are era appropriate!

Much more to come on this.........

sissy maid diane