Another guest caption (with some history)

Here's another guest caption, courtesy of indecisivecaptions.com. This Model is One i'm quite familiar with, to the point where there's some history for sure.

For regular readers, you may recognize a couple of previously posted pics of the magnificent Erica. She is amazing.

Yes, there's some history here. i have a habit of becoming infatuated with Lovelies like Erica. Sometimes, they become dominant figures in my feminization, especially when my infatuation is timed with some other femming 'event'.

In the case of Erica, my one and only journey into the 'adult baby' side of sissification happened to coincide with my love of Her pics in blue. So,, seeing this new Erica caption tonight led me to the plastic 'baby' panties. Let's just say that when i masturbate while gazing at this Beauty, it is very embarrassing to have Her 'see' me in those frilly plastic sissy panties.

Ah, such is the imagination of the sissy. But what's real is that under my plastic panties, i now have a cage locked on - courtesy of Erica. yes, Erica is the epitome   of sexy. Voluptuous, beautiful, wearing only the finest lingerie She is every sissy's fantasy.

sissy maid diane

sissy's dinner time

sissy maid diane

The ring of cocks

sissy maid diane

A guest caption (i'm impresssed)

Here's another great cation form my friends at indecisivecaptions.com.

i have seen this lovely Model before. my, She certainly has a magnificent figure. i just love the air of annoyance that Her sissy is asking for release from caging - again. It seems the whole pestering thing is starting to give Her something of a head ache.

This is when a sissy should simply stop whining and show some proper appreciation for the honor of caging for Mistress to begin with. Geeez, sissy, give the Woman an aspirin and a massage!

sissy maid diane

sissies earning money for their Mistress

sissy maid diane

see through panty caption

More sissy caption fun.

sissy maid diane

Double strap on fun

What could be abetter scenario for a sissy than submitting to the strap on? Submitting to two, of course.

sissy maid diane

Thawing out the cage

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 away in a mug full of ice. Free to masturbate!

Alas, only temporarily free. The long term prognosis for real freedom from the cage isn't good. i was having trouble sleeping last night and finally succumbed to that nagging need for caging.

As i thawed the frozen mug as quickly as possible with very hot water, my excitement and longing grew. So did my clitty.

It didn't take long to thaw it out and took much less time to come. The cage went on under my see through pink panties.

 i'm kinda embarrassed to admit that i didn't have any problem sleeping after the cage was back on. Back where it belongs, it seems.

Oh, my....................

sissy maid diane

The reluctant sissy

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

sissy maid diane

cuckold sissy caption

Here's some Saturday morning capping fun.

sissy maid diane

cock cage on ice

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 freeze it, but for now anyway, i'm free to masturbate without caging.

On Wednesday though, my hard clitty in my yellow panties seeemed to want what's in that mug.

There's just something about those cuckold Wednesday's. Oh, my!

sissy maid diane

Feeling poorly, but still a submissive

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'll survive, and i'm pretty sure i'll still be a subbie.  :o)

sissy maid diane

A timely sissy caption

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 on in recent sessions. And, there's this whole thing about sucking cock that i have to deal with.

Yes, i would characterize this as a timely caption that sums recent events up quite nicely.

sissy maid diane

Learning sissy humility, the hard way

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

During an IM session late Thursday into Early Friday morning, i was stressing out about a work issue and a big meeting to come on Friday evening. Mistress was capably playing the role of advisor, and i ultimately talked to Her on the phone as well. All good.

Mistress was giving me good advice while patiently listening. This is exactly what separates Her from most in Her profession - i think. It's not just about phones sex, sissy training and control. She brings a lot more to the table than that. When She plays the role of advisor, She's giving me the experience of a successful Woman's perspective on a problem that is insightful in two ways. One is just that - a different perspective, a different angle, a Female interpretation of what the right path is for me to take when a complex problem is at hand.

The second value of what's She's doing is actually a form of long term feminization. Real feminization is more than wearing panties and sucking cock. It's ultimately about feelings and thought process. i love the feel of nylon panties. But after wearing them all day every day, i slowly, surely begin to feel for feminine. One is an outward joy and feeling. Nylon material against my male genitalia is very nice indeed. Over time, another feeling, an inside feeling is growing under Mistres' tutelage.

i doubt that i'll ever have sexual reassignment surgery. i'll aways have male genitals. They belong top Mistress now, and that's the difference. i am a male who is becoming a Female, one step at a time. From the outside in.

When i back pedal & make a mistake like i did early Friday morning, Mistress has to take swift action. i was being arrogant, and was literally asking for Her to exert her Authority. Why would i do that? i could explain it like this - when She was counselling me the other night, my love for Her was overwhelming me. everything She does brings me closer to Her. When i'm feeling overwhelmed, i can make a mistake, and i did.

Here's just a part of the IM exchange, a small part:


pettimaid (1/6/2012 1:14:50 AM): You're killing me here. Show Your real Power. Leave more comments, use Your admin rights and post on my blog to Your delight. i live to please You. Have some fun! You just gave me 30 minutes, get Your ROI, Mistress Cassie. Use me, please............
Cassie_jones16.src%3Dpg (1/6/2012 1:15:30 AM): dont ever fear you won't be used....
Cassie_jones16.src%3Dpg (1/6/2012 1:18:14 AM):  I am just doing alot of reading here... this must be the best sissy blog on the web.
Cassie_jones16.src%3Dpg (1/6/2012 1:18:17 AM): go to bed.



Now, this may just a sample, but when She said 'Go to bed', i should have listened. i didn't LISTEN. She had already sessioned me, counseled me, during an earlier IM session and a phone session. During the 2nd IM session, She did what i asked Her to do, She looked at my blog. She complimented it and left comments. No sissy could ask any more from a Mistress.

BUT AFTER SHE COMPLIMENTED MY BLOG, i MADE THIS HUGE BLUNDER, INSTEAD OF THANKING HER AND GOING TO BED:

pettimaid (1/6/2012 1:21:13 AM): You should see my ranking on web searches. It's unbelievable how high my site anks on some searhes that compete with pay sites that i recognize. i'm a fucking sissy rock star!

There you have it. What an idiot! It took Her about 30 seconds to post and exert Her authority!

THIS IN NOT mY BLOG!!!!!! If i belong to Mistress Cassie, and i do, this blog also belongs to Her, and it does. i'm a sissy for sure, Mistress Cassie's sissy. i am NOT a rock star, She is.

Well, now i've got to deal with Her post and the ramifications. i'll have to find a way to appease Her. i will have to pay the price for learning - once and for all - real humility.

Much more to come on this - obviously.

sissy maid diane

sissy diane will be entertaining  gentleman callers  all during the months of  January and February.
If you want your dick sucked by a trained sissy,     post here, or email   sissy maid diane.  

Lets see,  how many cocks can she suck before the end of  February?

I am going to say  5 realistically,  but  I would love to see a score of at least a dozen.

Mistress Cassie.

Cross dressing delight

Now here's a picture i really enjoyed. This really looks like fun! These two cross dressers take things very seriously indeed. This being blue panty Tuesday for me, i might say that i can relate to the miss in blue. i really like her outfit and it's clear that she's just recently shaved. yes, lovely lingerie, and smooth nylon clad legs. Very inviting!

Being as i'm a 'giver' by nature i would happily trade places with the miss in black. It's what i've been trained to do, after all. And what a lovely package that resides under those blue panties. They both seem to be enjoying the moment, as did i when i first laid eyes on it.

Nice, very nice.

sissy maid diane

sissy strap on fascination

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 real ear full of Mistress giving me the business while i sucked Her lover's cock.

i recall a long time interest in this subject. Below is scan from an old copy of Club magazine that i happened to think of today. It's kinda worn (the cover is long gone) and there's no date, but i believe it's from the early 90"s. Let's say 20 years ago. i was married at the time, and D'x was not how'd i'd describe that relationship. i cross dressed in secret, and had secret magazines.

The ad is quite small, on a page in the back of the magazine with 12 other phone sex ads. But the impact wasn't small. i secretly masturbated to this ad, wanting to become Her girlfriend. Wanting Her to make me Her girlfriend.

The girdle has a lot to do with my cross dressing roots. This scanned ad form years ago has a lot to do with my interest in Female domination. And what better way for a Female to show Her domination?

sissy maid diane

Running for cover

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 on. Thoroughly Dominated.

i ran for the plastic cover of my cage, cowering.Oh, my!

sissy maid diane

The sissy and the girdle reality

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 those days in school when glimpses up Girl's skirts collided with puberty and was a major influence on my cross dressing.

The more i look at this picture, the more i look at the past. i think the most significant conclusion is that i was enamored of what i saw up those skirts before i saw what was behind the girdle. By the time i was finally introduced to Pussy, i had become a cross dresser. my interest in what covered the Promised Land has never waned. It's totally ingrained for me to be aroused at the sight of lingerie, and the feel of it.

It was a natural progression, and something that i was vulnerable to, for this to lead to submission to what lies on the other side of girdles and panties. Wearing them n,myself is half of the equation. Mistress Cassie is the other half. She turned my cross dressing into sissification and ultimately submission to Her.

i can't unring the cross dressing bell. That's a permanent part of who i am. The 2nd more recent bell that i can't unring Mistress holds in Her hand. When She rings that bell, i answer the call to servitude.

Like cross dressing, my submission to Mistress is also permanent.

sissy maid diane

Back to the nail salon

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 for a pedicure. The day before New Year's Eve, and a day when many are off. And at the mall, still lots of shoppers looking for bargains or returning gifts.

But i went anyway. Today was salon day for me. i went to this mall because it's (again) not too close to home. And because i have fond femming memories and experiences at that mall. It was there that i got a Macy's makeover, fully dressed in 2008. The mall also has more than one nail salon.

It was crowded, but not impossibly so. i found a parking spot and went to the salon that i used to frequent. There i also had built a relationship with a manicurist - 'M'. Happily for Her, but unhappily for me, She left the business early last year to start a family. And while i went to that salon and a couple of other's after She left, it wasn't the same. Like my hairstylist knew that i wanted the big girl hair dryer, M knew that i wanted color as a part of my pedicure.

The first time wasn't easy, and i sorta mumbled 'pink polish'. She either didn't hear me, or understand me. i got clear polish. It was on the 2nd trip that i got up the nerve to ask for color. And She didn't bat an eye. After that i usually let Her pick the color. It was all good. Especially the pedicures themselves.

This has to be one of the best kept secrets of the Female world. For a modest sum, the amount of personal attention, the wonderful ambiance, the vibrating chairs - it's unbeatable. Men are such idiots. i don't know one man who admits to ever getting a pedicure. It's a Woman thing.

Well, i'm guessing that Women everywhere hope that men keep thinking that way. i always feel a little self conscious when i get a pedicure. It's not so much fear of discovery either. It's more like a feeling that i'm in a Female sanctuary of sorts. The racks of polish, the pretty decor, the hushed tones of conversation (or gossip?). It's all so wonderful.

However, my manicurist is gone. So, i'm starting over. Todays' visit to my old salon didn't go well. There was no one to greet me, just a sigh in sheet. i signed and sat down. It wasn't all that busy, as i was the only one seated. i waited patiently as two customers came in after me and were taken in immediately. Maybe they had appointments, but i don't think so, given whet i overheard.i think it was a lapse in service, or maybe an assumption that i was waiting for my Girlfriend or Wife. Whatever the case, i decide to try another salon.

The good news was that i got a chair right away at location number two. The bad news was that the pedicure chairs were off to the side, barely, instead of in the back, like my old salon. i felt more exposed and the lighting was bright. More good news, though - i was the only one getting a pedi.

So, as the warm water engulfed my feet, i perused the menu. There it was, French or American pedicure. -$28.00. i wanted the French pedi. Rather than blurt that desire out, i asked what an American pedicure was. The Manicurist answer was that it was color, then She immediately suggested a 'manicure supreme'. Well, that conversation didn't go as planned, and i numbly accepted Her suggestion.

The supreme was great, of course. It involved a sea salt ex foliation, a mask, a lot of scrubbing away at calluses, and a lot of massaging. Nial polish wasn't part of the deal.

But, it was wonderful in every other way. my feet just felt alive afterwards, absolutely delicious. As usual, Mistress was correct in admonishing me for letting my salon visits wane. Being feminized can be difficult at times, but there are many rewards as well. Getting pampered at salons is high on the list. i will get another pedicure soon enough, and i will get up the nerve for color.

Just like my relationship with my Hairstylist, i'll find a new manicurist to build a relationship with. And Mistress doesn't need to worry about me sliding back into bad habits, like not going to the salon.

What was i thinking!

sissy maid diane

Back to the beauty salon

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 Mistress wasn't about to let me slip backwards in my training. i had until the end of the year to do a pampering day at the salon(s) or pay dire consequences.

So, today was salon day. This morning i called the beauty salon that i used to frequent. Not this salon, but close enough.

i had not been there since March. The Owner answered the phone and i asked if 'L' was in today. Right away the Owner asked "is this mr. d? (my other name also begins with d). When i replied yes, She went on to say how they've missed me.

Well, the whole thing about a gurl and the relationship with her hair stylist came flooding back to me. That's kinda the whole point in going to the salon. Relationships. The whole Female domain thing is part of it too, but after going there for 3 years i had built a relationship. Going to a chain Hair Cuttery is more convenient,  faster and a little less expensive. i got into the habit of going there because of time restraints. What i got was a quick, cheap, decent hair cut. Period. What i also got was a different stylist every time. No appointments, in and out.

Today, it was a lot more enjoyable. After getting caught up with 'L', i was surprised at how much She remembered about me, and likewise. After the hair cut, She washed my hair and as W/we approached  the 'big girl' hair dryers, She asked if i wanted some time under the dryer today. i did, of course, and i was about to suggest it. But again, She remembered. And i was reunited with the dryer.

The moral of part one of my salon day is that getting a hair cut can be just that, or much more. i chose the salon originally, in part, because it is 1/2 hour from home. A safety from discovery issue. The problem is that i now work in the other direction. But, the reality is that i need to find an hour a month of travel time to make the trip - for the relationship. The relationship between a sissy gurl and her hair Stylist.

Next, a different result on my nail salon visit.

sissy maid diane

The 'cage gauge' goes off - again

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 Mistress Cassie imposed minimum of 4 hours locked up. So, i found myself browsing through my picture folder.

Since i haven't masturbated, the 'gauge' is a little sensitive. But it really went off when i took a look at the scene above. Maybe it's because i got a thorough cuckold session from Mistress a couple of weeks ago describing, in detail, Her giving me the strap on while i orally attended to Her lover. Maybe the fact that Mistress made me suck a cock for Her a good while back and keeps that fact front & center - along with my dildo training.

Whatever the trigger, i posted weeks ago about sharing things that make my cage fill & here's tonight's installment. And the cage is really full tonight. :o)

sissy maid diane

Slipping into the cock cage

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 oil as a lubricant but Bianca suggested trying the stocking method, and described it along with giving me a link for instructions.

So, i tried it just now. i didn't masturbate, and that complicated things. The stocking i used was a nylon stocking that had a run in it. i cut off several inches from the toe up. Then i put the ring of the cage on and threaded the stocking through the cage. Basically, after inserting the head of my clitty into the open end of the stocking, i pulled the toe end through the opening and my clitty followed.

The only problem was that i was getting hard fast as i felt the nylon gently tugging me towards imprisonment. But it worked! Tomorrow i'll be going to the salons for pampering. i think afterwards i'll dress up and take some pictures.

Then i'll cum, gazing longingly, excitedly at the photo of Mistress above. After i cum, i'll demonstrate the stocking method with pictures. It should go on easier after cumming, and make at least the start of my next confinement period more enjoyable.

Thanks Bianca!

sissy maid diane.

sissy salon day dreaming

One of my two current assignments from Mistress includes a sissy pampering day. That will happen either tomorrow or Friday. A trip to the beauty salon for a hair cut & blow dry under the 'big gurl' dryer is a give. But then i think it's overdue for me to get a pedicure.

Pedicures are great and i actually miss getting my nails done. The only stressful part was the occasions when i got color. That trip form the chair to the drying station was a little embarrassing when i had a color like red applied. And yet a professionally applied coat of polish is so much more appealing than my do it yourself polish.

Since my hard to find  (t gurl friendly) manicurist retired to family life, i have been reluctant to search for a replacement. Maybe i'll inquire about French nails when i get my pedicure. They are very nice looking and i've been curios about the process for some time. And lots of the Women i view have them, usually on the fingers though. But not always....

Anyway, it may be a little less noticeable on my trip to the drying station. We'll see. i'm trying to get my nerve up now.

Maybe tomorrow's the salon day....

sissy maid diane

sissy gurl girdling

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 prefer. But today was a day to shave and put on lots of lotion and pamper myself. i'm feeling very very femme these days. Since i have some time off (finally) i'm going to enjoy being diane.

There will be more to come this week, but i wanted to start at the beginning, the girdle. The retro picture gallery of Tori took me back to the 60's when a good day was getting a peek of a Female Class mate's undies. It was usually a girdle. A great day was when one of them got careless and i got a look all the way to the gusset.

Two of the many things about Tori that really got my attention was Her spreading Her legs for that great gusset look, and the mixing of colors. my gusset isn't as smooth and inviting as Tori's (too much junk down there), but i liked the feel of spreading wide. It was also fun to mix colors of lingerie, something i rarely do.

It was fun - period. And it led to me soiling my girdle and caging. Usually when i masturbate wearing a girdle, i pull it down and let my panties 'do their thing'. Today, i was in such a girdle frenzy that i didn't even wear panties, like Tori. i just rubbed away and shot into that controlling spandex material. Then i caged and pulled my girdle back on..

Ah, Mistress Cassie's Hierarchy of  images and porn stars strikes again. If i had seen these pictures of Tori before becoming so enamored of Her, i might have figured out She was a bad Girl, a hardcore porn star who seduced me into caging & girdling with Her girdle shoot. Too late now.

Yes, Her impact was already registered when i saw just what a bad Girl She is. But i just had to do a pink girdle and blue bra shoot and here it is.

Much more to cum this week.  (wink)

sissy maid diane