maid diane's sissy blog

sissy diane, serving Mistress Cassie since 2008. Poor little diane, a lifetime cross dresser - now a sissy bride, CAUGHT in Mistress Cassie's feminization trap. Slowly but surely being transformed into a Female. While Mistress freely and actively pursues Her sex life, diane gets constant plastic pussy, dildo and cock cage training from Mistress. Teased, tormented, cuckolded, that's this sissy's new life. Oh yes, - it's all about Mistress Cassie now - there is simply no escape....EVER! Oh my!

Sunday, February 5, 2012

Another guest caption (with some history)

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Here's another guest caption, courtesy of indecisivecaptions.com . This Model is One i'm quite familiar with, to the point where...
3 comments:
Saturday, February 4, 2012

sissy's dinner time

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sissy maid diane

The ring of cocks

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sissy maid diane
4 comments:
Friday, February 3, 2012

A guest caption (i'm impresssed)

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Here's another great cation form my friends at indecisivecaptions.com. i have seen this lovely Model before. my, She certainly has...
1 comment:

sissies earning money for their Mistress

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sissy maid diane
Tuesday, January 31, 2012

see through panty caption

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More sissy caption fun. sissy maid diane
Monday, January 30, 2012

Double strap on fun

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What could be abetter scenario for a sissy than submitting to the strap on? Submitting to two, of course. sissy maid diane
Sunday, January 29, 2012

Thawing out the cage

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Well, after nearly three weeks of being free of the cage i caved in early this morning. i was free to masturbate while my cage was frozen a...
Saturday, January 28, 2012

The reluctant sissy

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These young Women entertained a LOT of male quests at Their party last night. sissy maid diane

cuckold sissy caption

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Here's some Saturday morning capping fun. sissy maid diane
Friday, January 27, 2012

cock cage on ice

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While i'm a little under the weather, my cock cage is under a small block of ice. i'm not sure why Mistres had me fr...
2 comments:
Thursday, January 26, 2012

Feeling poorly, but still a submissive

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i had a spell in the hospital last week and will be recovering at home for a while. Forget the details, it's too depressing. i'...
2 comments:
Wednesday, January 11, 2012

A timely sissy caption

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Let's see now, Mistress like for me to moan during sessions with Her. She has given me a good does of 'feeling' Her strap o...
2 comments:
Sunday, January 8, 2012

Learning sissy humility, the hard way

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Well, for those of you wondering what in the world happened to compel Mistress Cassie to post Her January 7 remarks - here its is. Du...
Friday, January 6, 2012

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sissy diane will be entertaining  gentleman callers  all during the months of  January and February. If you want your dick sucked by a trai...
3 comments:
Tuesday, January 3, 2012

Cross dressing delight

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Now here's a picture i really enjoyed. This really looks like fun! These two cross dressers take things very seriously indeed. This...
11 comments:
Monday, January 2, 2012

sissy strap on fascination

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my fascination with the strap on has been rekindled of late. After my last session with Mistress Cassie it has been on my mind. i got a...
Saturday, December 31, 2011

Running for cover

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Here's a photo that i came across that sent me running for cover. The sight of a sissy being throughly dominated by use of the strap...

The sissy and the girdle reality

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What has gotten me so sideways lately is the retro image of a Woman in a girdle. A pink girdle at that. i've written before about t...
3 comments:
Friday, December 30, 2011

Back to the nail salon

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After my rewarding, and relaxing, visit to the beauty salon, it was off to the mall. It dawned on me that this might not be the best day fo...

Back to the beauty salon

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i was busted by Mistress a couple of weeks ago for not visiting the beauty or nail salon regularly. my excuse was the job, of course. But M...
Thursday, December 29, 2011

The 'cage gauge' goes off - again

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Well, here i am, caged - again. An experiment with using a nylon to enter the cage. i still have more than two hours before i meet the ...

Slipping into the cock cage

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i had a fun IM session last night with my closest sissy gurlfriend, Bianca. Among the topics was putting on the cock cage. i use baby o...
3 comments:
Wednesday, December 28, 2011

sissy salon day dreaming

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One of my two current assignments from Mistress includes a sissy pampering day. That will happen either tomorrow or Friday. A trip to th...
2 comments:
Tuesday, December 27, 2011

sissy gurl girdling

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i can't remember the last time i came into a girdle, before today. Lycra spandex is not the silky sheer nylon material that i prefe...
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