The Slut to Sissy Cocksucker Conversion

Training a sissy cocksucker
 

Jaz lets us peek into his slut to sissy transformation journal

Diary entry 1
May 5th 2015

My last visit to Ms Sloane was an eye opening experience. Ms Sloane has a way about Her that makes you want to do whatever it takes to please Her. Usually it involves Her teasing and putting you in a humiliating situation that leaves Her giggling and planning the next adventure that test your limits.

Like…

That last night I was there, Ms Sloane introduced me to one of her Bulls named Thomas, and it was the night my whole life changed.

I am now and always shall be known as a Sissy.

That’s something I’d always had problems admitting to. Well, until last month, that is. Ms Sloane and her Bull made sure there was no time to think or to get the cocksucking jitters. She simply told me to suck his cock. So I did, all the while being guided by Her instructions. I stayed on my knees and sucked and licked until he grunted and exploded directly into my mouth.

I couldn’t believe it. I had just sucked my first cock.

I really am a sissy cocksucker!

I didn’t have much time to revel in my victory though. Ms Sloane and Her Bull began to slide a butt plug in and out of my tight ass, telling me that I had to be stretched for what was to come. Gawd, the pleasure-pain sensations felt so good and my own cock strained within it’s device, begging to cum.

Next thing I knew, Thomas’ big cock was working it’s way up inside me. Ms Sloane told me to sit on it and relax.
Ha!
Easier said than done. Adjusting to the thickness and length was more difficult than I’d imagined. But as different as it felt, I knew it was where I belonged. And that bouncing on that cock did make me feel amazing.

Her Bull made me his bitch and I love it

We didn’t have any fun after that glorious night, not for a month. She sent me back home, explaining that She would call when my services were required. Despite my soreness, I hoped it’d be sooner rather than later. Turns out it was exactly a month later.

When I arrived, Ms Sloane escorted me into Her office and had me sit. She walked around to her desk, her heels clacking softly against the hardwood floor and sat down to regard me silently for a moment.

“What are you?”

“I am a Sissy Ma’am.”


 

From Slut to Sissy Maid Part 2

 

Sensually dominating my sissy maid

 

 

 

Jaz’s sexy story continues…

When we last left the slut turned sissy maid…things were heating up…

“Stop slut. I’ve no need of it right at the moment. I’ve another use for you.”
“As a maid it is your duty to see that I have a clean and well stocked house at all times. Since you failed to do so, your tongue will do your service for you. How humiliating it will be for you, making Me cum and you not even so much as able to touch yourself…hmmm?”

There was little else I could do but to comply, knowing that this act was a sealing of my fate. That by my oral servitude, I will tighten the bond between us, just as surely as if You placed a collar around my neck and locked it.

Might as well live it up, because I’m in it this far already.

With a sigh, I sink to my knees by the bed and leaning in, I extend my tongue. I lap at Your folds, slowly at first and then faster, encouraged by the breathy moan that escapes Your lips. Gawd, You taste so good. As I glance up, I notice how sheer Your blouse really is.

Add that to the fact You aren’t wearing a bra. Damn. I can’t un-see any of this and my cock throbs in the device.  I stifle a moan of pain as You laugh at my discomfiture and then orgasm loudly. On my upturned face.

You don’t play fair.

My cock hates this cock control and being denied any chance of an explosion.

You push me away, walk down the hall back to the living room to sit on the couch with Your legs spread.

Take off my panties, slut. They’re all wet

I try not to look down at my cock expanding and the pain begins to gnaw at me. As I stare at Your glistening pussy, You matter of factly inform me that I will be serving You in the dinning room shortly and that I could eat in the kitchen, as fitting my station.

After dinner has concluded, but before I can breathe a sigh of relief for not having incurred your wrath, You tell me that,”You’ve done well, slut. I’m in a good mood so I’ve decided that you’re going to get a special treat in reward for your good behavior.”

I’m afraid to ask.

Help me get dressed.

As we venture to the bedroom you casually mention that Your Bull, Thomas is coming over. As You tell me about him, his thick cock and his preferences about all things sexual, You see the fear in my face and grin. My cock twitches. I’ve always wanted to know what sucking cock would taste like. It might not be all bad.

I hoped.

Do as you’re told tonight, slut and you’ll love it.

“You’ll be answering the door when he arrives and you will extend him all the proper courtesies before ushering him here, to My bedroom. Are we clear?”

“Yes, Ma’am.” I muttered.

Things were about to get scary.

Check next Tuesday, for the final installation of Jaz’s story and how becoming My sissy maid cocksucker isn’t such a bad thing after all.

 


 

From Slut to Sissy Maid Part 1

 

I’m sharing this erotic story with permission by the very lovely Jaz. Enjoy!

 

Feminization is almost complete

 

I arrive not knowing what’s on that devious mind of Yours. I dress causal, You not wanting the neighbors to know just what You do as I step through the door and all. You usher me to the bedroom where I’ll be spending the weekend. I have made this trip several times now considering Ky is only 3 hours away from me.

I’m so glad you’re here slut. Strip down, take a shower and be quick about it.

“I have several things for you to do once you’ve settled in. I see you packed light, that’s perfect. I’ll be allowing you to wear what clothes I deem appropriate this weekend and nothing more. So go shower. Be sure to shave from the neck down and hurry.”

Knowing better than question You, I do as told. When I return to the bedroom, You’re standing there and tapping your foot impatiently. There is a maids uniform upon the bed, complete with stockings, garter belt and a bra and panty set. Placed next to those are bra inserts and heels. I look at You, then the bed, my eyebrows raised questioningly.

I need My slut to be focused and that thing will just get in the way…

You glide over to me, yanking the towel from my waist and tell me to turn around and bend over. You lube up a butt plug, You slide it home, chuckling and whispering about needing to stretch me out for later. Turning me around, You grab my balls and squeeze them hard, making sure any thoughts of getting an erection this weekend are no longer a possibility.

You laugh as I bend over in pain.

“This little treasure will come off when you’re on the way out the door and heading back to Ohio. You are here for Me. My pleasure. And that thing of yours is no good to me.”
So here I stand, a slut with a butt plug in my ass and a chastity device on my cock and I can’t help but wonder what I’ve gotten myself into. Out come the handcuffs, with the instructions that they will come off…as soon as I’m dressed like a sissy maid. You help me place the breast forms with a flourish and un-cuff me. My transformation is complete.

No wig and no make up for you, slut. You haven’t earned the right yet.

“Not until I have witnessed you taste a real live cock and have had a real cock sliding in and out of that pussy of yours, do you get to become female. Until that happens you aren’t a male, you aren’t a female, you’re just a sissy to be used for pleasure. I want everyone who steps through the door to know that. Once I have witnessed your deflowering you shall remain as you are now….Understood? ”

“Yes Ma’am,” I reply meekly. “It may take a few more visits till I’m ready to take that step,” I reply.

My house needs cleaned and supper to be prepared before 7 o’clock, so you better get busy.

“The menu I need you to prepare is on the kitchen table, so you better get busy because by the stroke of 6:00, I’ll be inspecting your work and if it not up to my standards… well, you know what that means…”

You laugh and walk out of the room. I follow quickly behind, heading toward the kitchen while attempting to master the 4 inch heels. I open the fridge see a box of leftover Chinese food. Smelling it carefully, I shudder and open the box to see a thick layer of mold. I throw it away, stifling a groan. Since taking everything out of the refrigerator seems the best route, I wipe down the shelves as I go. Looking up I see an open closet with cleaning supplies. Awesome.

I finish cleaning up the kitchen before venturing into every room in the house. I became a cleaning machine, furiously dusting, vacuuming, washing the windows and desperately hoping no one sees me through the windows. Just when I think I’m in the clear, on the last room and ready to breathe a sigh of relief, both for not breaking an ankle or being caught in this sissy humiliation from hell that came gift wrapped in a maid’s uniform, I hear…

slut, bring Me a glass of wine. Make it snappy!

Damn. I trip over to the shining fridge and pull out a nice Riesling. Locating your wine glasses and pour You a glass without spilling a drop. Entering your office, You look up with an ornery grin and say “So how’s those heels treating you? ” Without letting me answer, You continue on.

It doesn’t really matter you know, by Sunday you’ll be able to walk just fine.

As I exit the room and head back to finish cleaning, You call me back in. Stopping once more, I walk back in the office. Without looking up You say,

Never mind. I just wanted you to get used to walking. Every woman needs to know how to walk in heels.

And You laugh and laugh as my ears burn.

About an hour later, I hear You emerge from your office and get yourself another glass of wine, before slipping off to your bedroom. I hear You calling out for me again, this time from the bedroom. Standing tall and regal, one hand cradling the glass and the other carressing a flogger. I bent down on one knee, hoping that whatever I’d done, it wasn’t going to hurt too much.

“Yes, Mistress?” I whispered.

“Dammit slut! All this cleaning and you fail to supply toilet paper?! What’s wrong with you?”

I feel the swift strike of Your bare hand on the back of my head. “I’ll get it, right away. So sorry Mistress.”

This will cost you dearly, I hear You whisper in my ear as I struggle to regain my feet, sliding around in the 4 inch heels.

You lean back against the bed, yanking up the mini skirt and pulling the sheer panties to 1 side. I was face to face with heaven and hell. Seeing Your beauty and being teased and denied my own orgasm. You tilt your pelvis and taking your right hand, you spread open your lips wide…

Check back next Tuesday for part 2. Now that I have My sissy maid doing my biding, it’s time to bring in the Bull. It only gets hotter.


 

Surprise! Sexy Mistress Sloane is Back

 

Cougar Sloan is Back!

Cougar Sloan is Back!

 

No this is no April Fool’s Joke! My wing-gal and fellow MILF, has returned to the LDW Empire. I’ve known of her arrival for a little while, and we’ve been gabbing it up too. As a treat for the fellows that have been pining away – Sloan’s has sent a post to share, until her blog is set up and ready to go.

The Mistress Sloane Chooses The Topic

It could have been anything from body worship to cuckolding, but she picked a topic I am very fond of – Cock Sucking. Sit back, relax and welcome back our sexy Cougar, Sloane.

Suck it for Me Because you Like it

I want you to think about that little secret you told to me, not too terribly long ago.  The one you’re probably hoping I’d forget?  The one that you bravely confided to me in a breathy little voice?  The one about you getting down on your pretty little knees and taking a cock between those pouty lips of yours  for the first time?

Ah yes. You do remember. So do I. And now that I’m back, it’s time to make good on that little cocksucking fantasy of yours.

Oops…did I just tell your secret? Yeah…too bad.

Sucking cock for the first time can be daunting, but oh so enjoyable. I’ll bet as mad as you are right now for my busting you out, your panties just got slightly humid. Am I wrong? Of course I’m not, my cute little wanna-be cocksucker.

Think about it for a moment.

Note: I didn’t say touch yourself and think about it.

Can you imagine what it might feel like? How wonderful it will be to feel a soft cock begin to grow in your mouth as you lick then suck it with a moan? I can. I want to be there to watch your transformation. Hear you tell me that you sucked my Bull’s cock and that you loved every single second from gag to swallowing that very last drop.

Say “Yes Ms. Sloane.”
Good.
Get on your knees for me.

 

 

 


 

MILF Mistress Vivian Pops Up

Read: A Rare Spring Day

A Rare Spring Day!

Hello dear Readers! I can’t believe it’s been so long since I’ve posted here on Your MILF Mistresses. It has been one heck of a Winter over here at the Casa de Kinky. Texas saw some snow, but Nothing like our Friends on the East Coast – who still haven’t seen the end of it. However today, Spring is starting to Pop Up – just like this sexy old gal. :)

In the spring a young man’s fancy lightly turns to thoughts of love.

Isn’t that a wonderful phrase .. a young man’s fancy? They haven’t cornered the market on fanciful, not these days. What about the Senior Set? This MILF is still  fancy and fanciful, even girlish and blushing when a compliment paid, is genuine and sincere.

Is youth wasted on the young?

Of course not! What is a sexy Cougar – without her young man to toy with? No waste here when a tasty young man prostrates himself in submission to me. It warms my heart, and jump starts my libido, when I look down on such a sight. So eager to please and so unsure how that is done, they are like the 1st blank page of a new journal – fresh, virginal and with a spine – yet to be cracked. Muhaha .. I digress ..

The Rites of Spring Mistress Vivian Style

Are you starting to feel it? The pull of Mother Nature that encourages the sap to rise, and not just in the trees. 😉 It is a time for celebration of renewal, and you can join in too. It will take some effort on your part to gather the needed items, either in the wild or florist shop. Keep your eyes vigilant for Springs’ first blooming shrubs and trees.

Gather ye rosebuds while ye may

Forsythia, with its tiny yellow blooms, or  cherry tree branches as they first begin to bloom, will be ready long before a single rosebud pops up, so keep a look out. Pussy willows and bundles of crepe myrtles can be found at most flower shops, and will do very well for our welcome to Spring Rites. Clip the ends, give them a good drink of water – and we are ready to begin.

Well …

Right after you drop those pants, and lay yourself across my lap.

 


 

MILF Mistress Vivian and Nurse Naughty

Turn Left & Cough

Remember back dear readers to those times when your imagination wasn’t filtered by years of living, and you could play Cowboys and Indians till the sun went down or the street lamps cam on. Sometimes that’s how I think about our BDSM sex play,  grown up games from the . . . → Read More: MILF Mistress Vivian and Nurse Naughty


 

The MILF & The Alpha Man

Do Fem Doms Switch?

 

Good Evening MILF Fans It has been way too long since I dropped some love over here on Your MILF Mistress! You know how it goes fellows, `tis the season for all kinds of shiny distractions, and endless errands. Today however, I am not leaving the house – . . . → Read More: The MILF & The Alpha Man


 

Why Ms Delia Loves Being a Cougar

Cougar Mistress Delia

I love being a cougar, and I think to be one, a woman must have a certain look, the right attitude, and plenty of sexual confidence. Those three characteristics are essential for the hot and sexy cougar woman! Really being a cougar IS all the rage now! We even had . . . → Read More: Why Ms Delia Loves Being a Cougar


 

Do You Need an Older and Wiser Fem Dom?

Real World Advice

 

Hey there, fellas.  Seeking that special someone?  The person who will listen to your darkest fears and brightest joys?  That woman who will brighten your path in life with her warm words as you walk along?  Want that wonderful, one-of-a-kind experience that you can only get with the right . . . → Read More: Do You Need an Older and Wiser Fem Dom?


 

Why Choose a MILF For Your Next Erotic Phone Sex Session?

Put Your Cock Into The Hands of a Mature Fem Dom

Hello there, Gents! What a Beautiful Day it is in TEXAS! So pretty that I snuck away for a few early morning hours at The Big Red, watching the birdies gathered at the river, fighting for what little water is left in . . . → Read More: Why Choose a MILF For Your Next Erotic Phone Sex Session?