Thursday, January 31, 2013

Just because........

This post, just because i like this pic.

sissy maid diane

Panty load

my, what a pretty sight!

sissy maid diane

Appreciating pantyhose

i have always been a big fan of nylons. While i was not happy about the introduction of pantyhose years ago, i have come to appreciate them. i still think that nylons and garters are the way to go, but there is real value in panty hose.

Quite appealing to view, and like hold ups, they feel wonderful against freshly shaved legs.

sissy maid diane

Tuesday, January 29, 2013

Transforming a man into a feminized sissy

Come on in Girls! We've got a man in our bedroom. 
We're going to have some real fun today. The plan is
to completely transform and feminize him in one day. 
We'll tease him along the way - of course. LOL!

sissy maid diane

Sunday, January 27, 2013

Bow job practice - caption


sissy maid diane

Female domination by young Women - caption

Women are inherently Dominant by nature, i believe. Never too young to start (after 18th b'day).  :o)

sissy maid diane

Saturday, January 26, 2013

sissy maid cuckold caption

i love this picture and have used it before. It's used me too, causing hours of cage time. Today, i changed the caption, and more cage time looms.

sissy maid diane

'Slip" into a strap on

i just luv slips!

sissy maid diane

Friday, January 25, 2013

Taking sissy out - caption


She is so sweet! And how thoughtful - taking Her sissy out to dinner.

sissy maid diane

sissy cuckold caption

When i saw this Beauty, i pondered being a cuckold. So, here's a cuckold cap for a change of pace.  :o)

sissy maid diane

One more strapon cap

Okay, i think i'll change subject matter, but first one more strapon caption.

Wow, i'm really taken by Her breasts! Just beautiful. The rest is sweet too. i think i need a little 'alone time' with Lililola. :o)

sissy maid diane

More strapon gang bang action


sissy maid diane

More strapon fun

i guess it's obvious what i'm think about theses days...

sissy maid diane

Milking the sissy

Once a Mistress uses the strapon, a sissy's life changes forever. When She milks him in this position, anything is possible.

sissy maid diane

Ready for implants - almost......

Not me, silly. Not yet.

sissy maid diane

Strapon gang bang - part 2


sissy maid diane

Strap on gang bang

Group femming............

sissy maid diane

Thursday, January 24, 2013

Feeling pretty - my favorite diane pics

i am really feeling feminine & pretty theses days. More so than ever!

i took a look at some of my photo folders from shoots past, and decided to post a few of them in the one place - here. These are among my favorite pictures of all time (diane's time).

There's even on eof me with Lililola.

i was feeling a bit slutty in some, flirty in some, and sissified in others. But they all have one thing in common. i was feeling pretty and Female in all of them.

And that's a very, very good feeling.

sissy maid diane

New sissy poll - what do you like?

When i browse the Internet for images, i'm always a little delighted when pictures of me show up. Especially when the search subject is forced femming and Femdon categories.

i also delighted that i get so many visitors. Thank you all for your interest, and for stopping by.

So, today i've posted a new poll. i'd like to know what appeals to reader's most about my blog. It will help me to determine content moving forward., I'll keep it open for a week.

Thank you for following & for your vote!

sissy maid diane

Dressing up for Mistress - caption

Here' a nice scenario. What a considerate Mistress, helping Her sissy with wardrobe selections.

In other news, i came across this while browsing for feminization images. It's not very exciting to look at, (not too sure about the grammar either), but the message is on point.  :o)

sissy maid diane

Wednesday, January 23, 2013

Tormented by Pussy - caption

So, i am all settled in with Lililola, my plastic pussy. In lieu of real Pussy, i'm very happy with Lili. Still, i can't help but torment myself once in a while with images of real Pussy. Real, very pretty Pussy!

sissy maid diane

When Women rule the world.....

Women are inevitably going to rule the world,  soon i think. They are, collectively, the Superior gender in all important categories.

When to the world order finally changes, i think i'll be in good shape. At the end of the day, feminization has it's rewards.

sissy maid diane

Tuesday, January 22, 2013

Shredded by Mistress Cassie

Oh, my!

sissy maid diane

Shaved legs and nylons

i'm currently bidding on 28 pairs of vintage nylons on E-bay. The auction is over at 9:30 P.M. EST tonight. i'm looking at this because several of the pairs are sil stockings. i'm really wanting to hear the swish of the stockings when i walk. i expect to do a post about this topic soon, maybe a video with sound. 

my legs are shaved. Hopefully i'll have some new (to me) silk stockings to model in a few days. 

sissy maid diane

Monday, January 21, 2013

Plastic pussy caption - learning from Mistress

One of Mistress Cassie's many strengths is Her ability to teach. She has shown me numerous feminine insights while getting me to embrace my inner Female self. And i have learned....

Naturally, real Pussy is now strictly off limits for me as She continues my feminization. my latest lesson - that plastic pussy will suit me just fine from now on...........

Oh, my!

sissy maid diane

Introducing Lililola

The answer is yes! i simply love Pussy! There is nothing better in the world. i love it so much that i have found my increasingly emulating Women as a result. One Woman, in particular, Mistress Cassie, has taught me the real power of Pussy, and has essentially pussified me. And Saturday evening Mistress  gave me a great gift. She allowed to to cum into pussy. The earth moved, such was my orgasmic delight.

It wasn't the real thing, of course. i've been permanently weaned from real Pussy by Mistress. But after Saturday, i now have Lililola in my life to help fill the Pussy void.

Saturdays' session had a cordial getting caught up tone to it early on, After all it had been a year since my last session. Then Mistress asked what toys that i had in bed with me. It was the big dildo, the clitty cage, and my plastic (Fleshlight) pussy.

Mistress wanted to know if i'd named my pussy yet. It had never occurred to me, especially since the relationship had not been consummated. In fact i had never been able to cum into any masturbator for decades, despite numerous purchases and efforts. So, She suggested Lillian, a lovely name for sure. But it wasn't satisfactory. i suggested one of my picture game Models as a possible name. i started with my favorite, Monica......

That seemed appropriate, what with my freshly shaved legs and silky new nylons. But it didn't strike a chord. Then, i threw out the name of a newer Model of interest, Lola.....

Mistress like that and combined it with Lillian to make a new name, that rolls off the tongue. Lot's of l's W/we actually tried a few different spellings and Lililola was born. i was already obssesing about Lola and had purchased a pink opaque pair of PVC panties, similar to what She is wearing.....

The greatest obsession of all. with Pussy had taken on a new dimension. Lola gets an assist, but it was Mistress would did the impossible.

Mistress used Her amazing hypnotic talents & voice to set the mood. As always, She was drawing me further into hypnosis with that remarkable Voice. As the session subject turned to Lililola, She suddenly put me on the clock. She counted backwards from 10, all the while interjecting mind control remarks about Her control over me, and the inviting plastic pussy, which i had now entered.

By the time She got close to 'one' i was beginning to realize that i was about to cum.. And cum i did - right on time!

i came and came and came. It was as if all those years of not being able to masturbate to orgasm in a masturbation device had backed up into a cum reserve. It was a game changing explosion.

It will be interesting to see where this leads. Armed with a very effective new toy, Mistress will undoubtedly be femming me even more. i will follow Her lead. me & Lililola.

The teasing, plastic covered Pussy of Lola will figure in there too.  :o)

sissy maid diane

Sunday, January 20, 2013

my sissy gurl friends

While i have been under feminization by Mistress Cassie, i have made numerous sissy friends. Mnay as a result of this blog, and Mistress encourages me to have sissy gurlfriends.

My sissy gf's include sara, leanne, michelle, candii, and toni to name a few.

Then, there's bianca, my best gf. Last night,  i IM'd with her just prior to my session with Mistress. We chat about all kinds of gurl things and last night she shared a link to a site she's joined.

Check her out at

bianca is a hottie - and a sweetie.

Kisses bianca! And all of my gf's  :o)

sissy maid diane

Locked in lace - Part two

Here are more pics from last night's 'locked in lace' shoot. More to come about the details of my session with Mistress Cassie.

My 6" locked heels:

The cock cage:

The locked collar & leash:

sissy maid diane