NEW! Short Story: "Lulu's Story."

Clever Sissy

Please allow me to introduce myself. My name is Lulu. I am a Sissy Maid....

Just three years ago I was you.  Sitting at home in front of the computer or scrolling through posts on my phone.  I too daydreamed about being a sissy.  Feminized by a man or woman whom I’d willingly and enthusiastically submit to if given the chance.

I too looked at the erotic pictures, read their captions, and dreamed of being the main character of the same fiction you stroke yourself to.  I too dreamed of wearing the outlandish beribboned satin dresses; with their accompanying petticoats, satin panties, thigh highs, garter belts, and more.  You see, we wanted the same things.  But I must warn you, there is more to becoming a sissy than those things.  There is so much more…

When I told my girlfriend about my interest in chastity she was quite unsure at the time.  Why would a man want his cock, that which makes him a man, locked away 24/7 and inaccessible to everyone else, including himself?  Wouldn’t that be humiliating and degrading for him, she mused?  What would he say when showering at the gym after a workout?  She didn’t quite understand it in the beginning, but nevertheless, she played along with his somewhat unusual fantasy.

Quickly though, she came to realize the power her key possessed over me.  Void of self-pleasure, I was soon subjugated to pleasing her more than myself.  With a plethora of material online, it didn’t take her long before she began to tease me further.  I vividly remember the first time she woke me up in the middle of the night by planting her sex on my face.  “You’re going to make me cum until I say stop.” Were the only words spoken before her slick pussy muzzled my face of any protest.  After a mere four weeks in chastity she had already been queened while my sex remained locked, begging for release.

A few months later she came across my one and only sissy dress.  A bespoke French maid outfit no self-respecting woman would ever be seen in.  This wasn’t the typical French maid outfit worn by Jennifer Aniston.  No, those were much to refined.  I, a sissy, required so much more than that.  Satin, ribbons, petticoats so wide doorways became troublesome, pinafores tied behind my back, unforgiving five inch heels locked to my feet, thigh highs, and garter belts.  Unbeknownst to me at the time, these were just the beginning in my three year long transformation.

Soon enough, bells were added. “They allow me to know not only where you are at all times, but also that my little sissy isn’t slacking off.  A jingling sissy is a busy sissy.” Was how she explained their necessity to me.   Nowadays, I wear bells on my heels, wrists, and collar.  “Now if any part of you moves ill know!”  she exclaimed enthusiastically the first time.

Even still, you may still be thinking to yourself this all sounds like a dream.  A fantasy land so many sissies would die to experience.   What sissy wouldn’t enjoy these things?  After all, isn’t it in our nature to be denied, humiliated, degraded, used, and overly sexualized in our appearance, mannerisms, and lifestyle?  I too enjoyed the mincing and prancing, the swishing petticoats, the hair, makeup, and breast forms.

But, as with many people, enough is never enough.  Learning to reliably cum from anal stimulation alone took months to acquire.  In that time, I was forbidden from being released.  I was only allowed one supervised unlocking every two weeks to shave.  Of course numbing cream was applied before starting to ensure I remained flaccid.  Mistress, yes, that was her name now, also locked my hands behind me to prevent any urges I may get during that time.  I was also blindfolded during this.  She insisted a sissy shouldn’t be permitted to look at their own unlocked clitty.  That privilege was reserved for her.

Do you know how dehumanizing and degrading it is to not see your own sex?  Not only can I not touch it, I can’t even see it locked behind the pink plastic!  You, the person reading this, most likely still have the ability to touch yourself, stroke yourself, and even orgasm on your own.  I’m afforded none of those privileges.

My milkings, which elicit virtually no pleasure for myself, occur on the first Saturday of every month at precisely 8 AM.  In the pursuit of efficiency, Mistress purchased a prostate e-stim device that, when inserted in my pussy, will milk me in less than 30 seconds.  I feel the tingling deep inside me as my prostate releases what little maleness I still retain.  She then brings the small dish of cum up to my mouth as I obediently swallow, thanking her at the end for being such a wonderful and caring Mistress.  Before leaving me though, I’m required to ask her to do the same to me the following month and to never unlock me again.  My once cherished release is now utilitarian in nature.

In order to keep up with her relentless chores and schedule I was given a choice.  I could either quit my day job and become her full time sissy, dedicating myself to this lifestyle.  Or, I could leave and never return.

I’m sure you can guess which option I chose.  My wardrobe quickly ballooned in size.  Dresses, shoes, and lingerie were delivered almost daily until my closet ran out of room and what remaining male clothes I had were donated.  Nowadays, the closest thing I have to what a man would wear are a few blouses I’m permitted to wear when running errands in public.

Her latest change has worried me more than anything else though.  Yesterday she showed me her Tinder profile for the first time.  She had men, real men, lining up left and right for her.  She flipped through a few of her matches before stopping at one in particular.

“His name is Liam and he’s taking me out for dinner this evening.”

My heart sank at this revelation.  My love, my Mistress, was seeing another man, a real man.  I was being replaced right before my eyes.  I was no longer her man.  I had very abruptly, and unceremoniously, been relegated to the role of cuck.

So yes, according to many people I’m living a dream.  But this ‘dream’ has cost me so much.  Please think of me next time you make love, masturbate, or read erotic literature, and know that I’ll be here in my own feminized world.  Devoid of all those things you take for granted.