Category Archives: Chastity Sissy

Sissy Chastity – Do You Have What it Takes?

 sissy chastity

There are a lot of wannabe sissies that truthfully, don’t have what it takes to be a bonafide sissy that is worthy of the name. Let’s find out whether or not you have the potential to become a real sissy maid.

I think it all begins with the proper mindset. Becoming a chastity sissy to be proud of will
require you to exorcise any ‘macho-man’ desires still left inside of you? A true
sissy is no longer a real man, but a chastised sissy maid. Being a sissy means you are no longer
required to control anything or anyone. Your only role is now to perform the
duties of a sissy maid. You simply do what you’re told to do. Couldn’t be
any simpler than that.

The next issue is body hair. Women shave because it’s feminine and sexy. As a
sissy, you need to start shaving from head to toe…. no body hair allowed! Once you start to shave, a shift will begin to take place inside of your
head. A transformation from male to sissy. Once a week is fine to begin with. You
will be amazed at how quickly you become proficient at it. Before you know it,
you will look forward to shaving more often.

sissy lingerie

Time to talk about clothes. Sissies are gurls so they don’t wear men’s
clothing unless absolutely necessary. Real women adore the sexy feeling that
soft, silky fabrics have against their body. If you work outside of your home, a
pair of panties, garter belt, and nylons should always be worn under your work
attire. When home alone, thong panties with a matching bra along with high heels
at least 4 inches in height should ALWAYS be worn.

Start keeping your panties, bras and lingerie in one of your regular dresser
drawers. There is no need to hide them away any longer. You are now becoming a
true sissy so start acting like one.

You need to wear high heels constantly as you will need the practice
to learn how to walk properly in them. This will take some time. As a new 
chastity maid
, you have a lot of catching up to do. You eventually will become very
comfortable wearing heels, so much so that the time will arrive that you will
never want to take them off (and why would you)!

sissy chastity

You are beginning to look and feel like a real sissy. There is one
problem though…. your undersized and underperforming dick. Look, if you were
hung, there wouldn’t be any reason for you to be a sissy.

Real men have big dicks, that consistently get hard, so as to fuck women the way they need to be
fucked. That’s not you; women don’t fuck sissies! That’s exactly why a sissy’s dick is kept under lock and key because she doesn’t qualify as a man anymore.

The only way you should ever be fucking a girl again is with a strap on dildo.
That’s your role as a chastity sissy.… to serve…. preferably in the most humiliating,
and frustrating way possible.

If you don’t have a chastity device yet, it’s time to start thinking about
ordering one. Long term denial will keep you in a constant state of arousal that
will enhance your ability to perform your sissy duties in outstanding fashion.

What Does It Take To Be a True Sissy In Chastity

A true sissy wants to always look as sexy and desirable as possible. Skinny is sexy!
You will look better in feminine clothes with an in-shape body. You are no
longer a macho-man-pig that eats pizza and drinks beer. Sissies don’t do that;
beer bellies don’t appeal to them.

It’s time to ‘starve-down’. Your appetite and psyche
will adjust accordingly once you commit to eating less…. a LOT less. When you
acquire that thin body that looks fabulous in your sexy sissy outfits, you will
be super motivated to stay sleek and slim.

sissy makeup

Let’s talk make-up. A capable make-up job will add the finishing touches to
your sissy persona. If you don’t have anyone to help you out with this, it’s
really not a bad idea to learn how to apply make-up yourself. This will take some
time and practice to become good at, so start practicing now!

Besides the essential stuff to have in your make-up kit like foundation, powder, eye shadow,
eye liner and lipstick, you should also add a lip-liner pencil in order to draw
in fuller, sissy-like lips. And nothing will turn you into a desirable sissy
faster than a set of extra long false eyelashes.

One last thing to talk about. Since you have given up your role as man, such
as it was, and now consider yourself a true sissy gurl, you will undoubtedly
find yourself in situations that any woman would, sexual relations with someone
of the opposite sex. The opposite sex of you is now of course a man.

You’re still heterosexual but as a sissy, the
naturally sex partner for you is now of the male gender. Although you’re no longer qualified
or permitted to fuck girls, you are more than capable of pleasing a man. But you
need to start practicing. You can develop and refine your oral sills sucking on
a dildo. Also, purchase a butt plug and keep it in your ass for extended periods of
time in order to stretch yourself out.

Men typically don’t like the gagging associated with an inexperienced sissy
attempting to swallow a dick that’s too big for her. That same big dick will
tear your ass apart if your aren’t adequately stretched out beforehand.

dildo training

If the thought of having a sex with a man thoroughly disgusted you when you
were a ‘man’, don’t worry. As a sissy gurl you will learn to crave a nice cock,
both in your mouth and up your ass. When you are able to swallow his load
without gagging, you have reached the position of a true sissy.

To recap, you’ve come to terms that your lot in life is as a sissy maid and
completely given up on the idea of being a real man.

You’re now smooth and sexy, as in hairless.

You wear bras, panties, high heels and lingerie every chance you get.

You’re dick is now locked up (as it should be) and you are beginning to feel
the benefits of long term orgasm denial.

You are losing weight as you want to be the best looking sissy you can be.

You’re taking every opportunity to improve on your make-up skills.

You are training your mouth and ass to properly service a dick.

Being a true sissy is all about letting go of the need and desire to be a man any longer.

It is so freeing; there is nothing to worry about any more.

You no longer need to be afraid to approach women. You will never again
be nervous about asking a girl out as you won’t be doing that any more. There will
be no anxiety associated with getting it up and keeping it up. There are no dates to pay
for or presents to buy. All your extra money will now be going towards make-up,
lingerie and high heels.

There is nothing more for you to concern yourself with other than looking as
pretty, sexy and feminine as possible.

Once you admit to yourself and the world who you truly are (a sissy),
everything naturally just falls into place.

You now think and act like a gurl. But remember, in order to completely
remove any last remnants of masculinity, your dick must be locked up and denied for
extended periods of time. The only way to effectively do this is with a chastity
device. You can find some nice ones by clicking here.

A Day in the Life of a Chastity Maid

chastity maid

You may have your own idea of what a day in the life of
a chastity maid is like…. and since I happen to be one, I have mine.

A chastity maid no longer qualifies as a husband or even a boyfriend for that matter.
She’s now merely a sissy maid, which is barely one notch up from male chastity slave status.

A chastised sissy maid serves only to make the life of her Mistress (and
her friends) easier…. A LOT EASIER.

My day begins early in the morning, long before my Mistress wakes up. I start
off my daily routine with shaving, showering and applying full make-up.

I then put on a bra, panties and nylons under her sexy maid’s outfit. My maid’s uniform is completed with 4 inch patent leather pumps.

It’s now time for me to wake my Mistress up without any touching. As a sissy
maid, I’ve learned my place.

I proceed to serve her coffee and fruit for breakfast
and then scurry off to run her shower. While Mistress is in the bathroom getting ready for work,
I lay out her clothes for the day, as per instructions from the night before.

I now run off to my bathroom, as fast as my high heels
will allow me, so I can get ready to go to work. Yes, I’m still legally
married to Mistress and although I’m no longer needed to play the part of her
husband, I’m still required to pay it.

The income from my job serves to keep my Mistress’s dresser drawer full
of fine lingerie and her shoe closet packed with expensive high heels.

Then there are the costs associated with her hairdresser, manicurist, tanning salon, health club
membership, massage therapist and tennis lessons to take care of.

I am also required to put away a good portion of my pay check in a vacation fund…..
for Mistress and her boyfriend. Once, every so often, they take me along to serve
as their personal maid, dressed as such. I’m not quite passable, so it’s
an overall humiliating experience for me.

Once my make-up is off, I jump into the shower and attempt to clean around
and under my
. It hasn’t been removed for three
straight months now as Mistress’s new boyfriend isn’t yet completely sold on my role as a chastity
maid and feels a bit insecure with another ‘man’ living under the same roof as his girlfriend.

As a good chastity sissy maid should, I always wear a pair of panties, a garter belt and nylon stockings under
my ‘male’ work clothes.

Once I get to work, I can expect a daily text from my Mistress telling me to run an errand
or two during my lunch hour. I usually forgo eating any lunch as I’m expected to keep my
girlish figure in tip-top shape.

I rush home after work to re-apply my make-up, get dressed, don a frilly
apron and began preparing dinner. Mistress’s boyfriend is coming over for the evening and everything must be
perfect. If it isn’t, she has a penchant for the riding crop and has proven
that she’s not shy about using it on me when necessary.

My Mistress arrives home and I must greet her at the door, kneel down and
kiss the tips of the toes of her high heels. I then take her coat and purse and brings
her a glass of wine before continuing with dinner preparations.

When her boyfriend arrives a bit later, I must greet him at the door,
kneel and kiss his shoes. I absolutely HATE doing this this but Mistress claims that
this submissive behavior of her chastity maid produces a warm glow inside of her pussy.

Her boyfriend and her sip wine and make-out on the couch while I work on
dinner. After eating, she calls me in to inform me that while she’s feeling exhausted and not up to any lovemaking for the evening, her lover is quite
horny and will require some ‘feminine attention’.

I am instructed to clear the table, clean up the kitchen and then head upstairs to get all
dolled up. I am told to freshen my make-up, apply extra long false eyelashes, then put on
my sexiest lingerie and highest heels. I am admonished not to keep them waiting long.

My Mistress always like to have her boyfriends set the proper tone early on in
their relationship in order to show her chastity maid who the real man of the house is. Tonight is that night.

She has me swallow a muscle relaxant, gives her boyfriend a Viagra, sits
back with a glass of wine, and watches the mayhem begin. It’s quite an erotic and
enjoyable show for her as I’m forced to show off my improving oral
skills and then eventually I get the shit thoroughly fucked out of me.

Her and her lover then head off to the bedroom while her chastity maid is left to clean up the mess.

The following morning I lightly knock on her bedroom door, fully dressed
and made-up of course, to take their breakfast-in-bed order. The delicious eggs
benedict and champagne meal that I serve has rendered my Mistress quite horny and
her boyfriend also seems aroused.

I am instructed to bring in a pad and pen so I can write down my chores for the day. As
I prepare to receive my orders, she sits up and straddles her lover, guiding his now raging
hard-on into her wet pussy.

She then erotically gives me my instructions; vacuum the entire house,
hand-wash her bras and panties, detail the car as they will be going out tonight,
press her boyfriend’s shirt and shine his shoes.

Mistress begins to softly moan as she is telling me to wake them both at noon after
making love followed by a short nap. She can now no longer talk so just snaps her fingers as a signal for
me to leave so I can begin my work…. while she plays.

I wake them up on cue and my mistress is horny again. Her boyfriend doesn’t
seem to be responding in like fashion so her chastity maid (me) is instructed to ‘fluff’
him up to size. I’m am then forced to stand there and watch them make love as a painful reminder of
my inability to please a woman with my shrunken and caged-up dick.

The sight of her chastised, feminized and frustrated maid standing there,
sexually denied, while she is free to make love with abandon is just too much for
her. It soon sends her tumbling over the edge, screaming in delight. Her lover follows suit shortly.

I used to be required to clean my Mistress’s my pussy after intercourse but
I’ve since been cut off from all sexual intimacy and contact. I am made to perform ‘clean-up duty’ on
her boyfriend however. I have learned to do this without flinching as the memory of one of
her brutal ‘cock caning’ sessions is forever entrenched in my mind.

After showering, she has her boyfriend go out and inspect the car to make sure
it is detailed to her satisfaction. When he returns, she calls her chastity maid in
as she has a little surprise for me.

It seems that her lover is having concerns over the security of my
chastity. She has assured him that it is very secure and I’m rarely let out except for quarterly supervised orgasms of the most humiliating variety.

Never-the-less, he has insisted that I get a

male chastity piercing
for my dick as added security. She wholeheartedly agrees and instructs
me to make an appointment that afternoon to get a PA piercing for the end of my dick. I’m
told to request a young female technician to perform the piercing. She and her boyfriend
plan to accompany me and watch the entire procedure.

She then informs me that, from this point forward, her lover will be taking sole possession of the key to my chastity cage. I
immediately turn pale and begin to visibly shake but I eventually calm down enough to
re-assess my predicament.

I will now be performing sissy maid duties for two. I am instructed to go fetch
my lipstick. When I return I am told to fall to my knees, crawl over to where her boyfriend is sitting and re-do my lips.

She then removes the key to my chastity cage from around her neck, hands it to
her lover and orders me to unzip his pants and gently pull his growing dick out. “He now has the key to your cage”,
she says to me. “If you want to cum again anytime soon, kiss it softly and sweetly, as if it’s the most important thing in the world to you.”

And I do.

I’m a perfect example that a sissy maid can only be at her best when her dick is kept locked up. Being kept in a constant state of arousal helps me to focus my attention where it should be, on my chores.