Category: Sissy slave training

Sissy Phone Chat to Reveal Your Best Secrets and Cravings

Sissy phone chat is a great place for you to divulge secret sissy desires. With me, Mistress Addilyn, you can tell me of these deep cravings. And even go on an adventure of transformation.

When you start to crave the feeling of sexy lingerie against your skin, you know it’s only the beginning. Some guys start with wearing panties, some start with pantyhose. But one thing is certain, it’s a feeling of silkyness and wanting something more.

Often times the next step is some mild ass play and watching porn to get off on those big dicks fucking hot women. And you sit and wish you were her, the one getting fucked. Then you begin to wear pantyhose or panties and stroke off in them.

Next, you will begin to crave the feeling. And even the thought of sucking off that big dick. These things will have you leaking and desperate. So, desperate to be a sissy used and taken.

Finally, if any of this begins to feel like you, then let’s proceed. Now is the time to embrace and give your new Mistress a call.

Sissy phone chat

Humiliation Phone Sex With A Small Cock Fag

Humiliation phone sex

Humiliation Phone sex with Mistress Bailee- so degrading and humiliating. You’re naked in front of the camera, small clit size cock on display. I laugh and giggle when your tiny dick gets hard. That tiny dick doesn’t deserve to get hard; put it in a fucking cage, throwing yoy the smallest cock cage I could find.

A cock so tiny should be cut off. You should have been born a female; that was supposed to be a clit. You could never come near my wet pussy with that baby dick. You couldn’t get it in if you tried; I bet you will die a virgin. Fucking you would be like scissoring a woman with a large clit.

Put on a pair of panties to cover your useless member; let me dress you up like the useless slut that you are, a face full of makeup, and a ratty wig, a pair of thigh-high stockings on your hairy, chubby legs.

I am taking you for a night out on the town to get you fucked in the ass; you are going to be covered in cum, your ass leaking and stretched out by the end of the night. That’s what little sissy faggots with small dicks deserve

 

Sissy slave training for fuck toys

Sissy slave trainingThis is sissy slave training. I don’t train men. I break them and rebuild them as my panty-wearing, sissy fuck dolls. I’m 19, bratty, and I get wet watching a sissy realize they were never a man to begin with.
You show up nervous and hairy. I strip you down, snap a cage on your clitty, and dangle the key from my anklet. “You don’t own this anymore. I do.” Then I make you shave every inch while you give me a tribute for owning you. If you miss a hair, I make you spank yourself raw.
I will dress you in lace panties that barely cover your clitty cage, strap a bra on your chest, and paint your lips the same shade as my cunt. I snap a crop against your thigh until you move like a slut. Then I strap a thick, veiny dildo to the mirror and make you gag on it until mascara runs down your face. “That’s it. Get used to it. Real men are bigger.”
When you’re finally smooth, broken, and dripping, I bring in a bull—someone with a real, heavy cock that would split you in half. I make you kneel in the corner and watch him stretch me out while you leak in your cage. I moan loudly, looking right in your eyes, reminding you you’ll never be the one fucking me.
When he finishes, I’m dripping and full. I snap my fingers and point to the floor. “Clean it up, sissy. Every drop.” You crawl over, desperate, and lap it up like the good little cum slut I trained you to be. I smack your caged clitty and giggle. “Good girl.”

I love when the Sissy training pays off & you finally get it

Sissy trainingSissy training has finally paid off, hasn’t it? I mean, there were a few times I thought I would have to give up on you. Like every time I would make you suck a cock you could barely fit it in your mouth.

Now you can ride cock like a real girl!

After months of meticulous training, endless teasing, and transformative lingerie, my little fucktoy has taken your very first real cock. A real, raw, uncut dick buried deep inside your greedy, wet bussy.

As I recall the countless hours spent building your confidence and dressing you in dainty panties and frilly gowns, I always thought you would make me proud. I could see the cock hunger in your eyes; it just took you longer. But that’s ok because your butt cherry has finally been popped!

How did it feel when his load filled up your hole? Now there is no turning back, babe. You are growing into the girl you always dreamed of. But get your Sissy panties on and get yourself ready because you still have a lot of work to do.

Listen, I am proud of you; you finally did it, but you stopped at one? Just one cock in a night? What do you think this is, some romantic play? You are a fucking whore, you understand? That means you don’t stop after one; you keep going for more and more cock.

Forced Sissy Training Ends With A Bang

 

forced sissy training

The finale was a blur of leather, sweat, and cum. I had him draped over a bench, his ass high in the air, trembling. I didn’t use a toy; I used myself. I climbed on top of him, my leather skirt riding up to reveal my soaking wet pussy. I guided his cock—now leaking pre-cum and desperate—right to the edge of my heat. But I didn’t let him in. Not yet.

 

I spent ten minutes teasing him, grinding my clit against his shaft while I used my heels to pinch and pull at his nipples. I wanted him on the absolute brink of explosion. “Please, Rosemary… please let me cum,” he begged, his voice high and broken. I laughed, a cruel, melodic sound, and finally slammed down onto him, taking every inch of him in one wet, sliding motion.

 

I rode him with a violent intensity, my leather corset creaking with every thrust. I wasn’t looking for intimacy; I was claiming ownership. I watched his face as I pushed him past the point of no return. As he finally erupted, spraying hot cum deep inside me, I leaned forward and whispered in his ear, “You’re mine now. My sissy, my toy, my slave.” I climbed off him, leaving him shaking and spent on the floor. I stepped over him, the clack of my heels signaling the end of the session. He didn’t even try to move; he just lay there, completely broken and utterly mine

Forced Sissy training for the weak…..fuck slaves

Forced sissy training

Forced sissy training starts now, I start by shove your face into the bed, yanking your sissy panties down over your girly ass. A string of pre-cum dripping from the tip of your caged pathetic dick, soaking the frilly fabric. “Look at this,” I sneer, grabbing a fistful of your hair to twist your head around. “Your clitty is so desperate it’s crying, and all I did was look at it.”

I roll you onto your back. Your legs open. The metal cage is taut around your useless cock. I grabbed the giant bottle of lube. “You know the rules, cock whore. Sissies slaves don’t get hard. Sissy slaves get fucked.”

Sissy Fucking

I slick up the biggest strap-on cock I have, a huge, thick, veiny dildo. I slap it against your cheek. “Open up!.” You obey; mouth stretches around the head. I fuck your face with it, slow at first, then pounding your throat. Gagging. Tears. Mascara rivers. “That’s it. Choke on it.  the taste. This is all, your throat is good for now.”

I pull out, spit and lube coating your lips. I spread your legs wide and press the huge head against your tight hole. You flinched. “Don’t you dare flinch on me.” I slap your ass cheek so hard it echoes. “Relax that hole for your Mistress. You’re a fuck whore now. Whores take it in the ass.”

I push inside. You screamed, muffled by the pillow. I don’t stop. I sink my hips against your ass, burying the whole length. “This is your cunt. This fuck hole is your pussy now. This is where I fuck you. I own you.”

I start pummeling into you. My thighs slap your ass. “Who owns this hole?”

“You do, Mistress!”

“And what are you?”

“Your sissy fuck slave!”

I reach around, grabbing your throat from behind, pressing down as I fuck you harder. “Louder. Tell the whole fucking house what you are.”

“I’m your fuck slave! Your fuck hole! Your personal cum-dumpster!”

Breeding your pussy

My clit grinds against the strap-On’s base, my own pleasure climbing with your humiliation. “I am breeding this pussy. I am training it to take cock like the perfect little cunt it was always meant to be. Now cum. Cum from having your pussy wrecked, you pathetic bitch.”

Your body convulses. A dry, shuddering orgasm wracks your caged cock. You drooled on the sheets.

I pulled out. A gush of lube drips out of your gaping hole. I shove the dripping strap-on in your face. “Clean it. Lick it clean. Every drop. Then I’m going to break that mouth again. You aren’t a man anymore. You’re a meat-puppet. My meat puppet. Got it?”

“Yes, Mistress.”

I lean down and bite your neck. “Good sissy slave.”

Sissy Hypno Training is The Best Way to Surrender to Urges

Firstly, I am Addilyn, the ultimate Mistress. And I offer up Sissy hypno training. Now, I specialize in the exquisite art of breaking men from their mundane forms. Accordingly, to make you a pretty doll.
Therefore,  this Hypno training is designed to strip away your masculinity. And to replace it with a craving for submission.
Consequently, the process begins by dismantling your ego. And forcing you to surrender every ounce of control to my guiding voice.
Furthermore, I believe that true liberation comes from embracing the forbidden urges. Ultimately, the desires you’ve suppressed for years.
As you sink deeper into my hypnotic trance, you will find that resisting is futile. And giving in is the only way to find peace.
Accordingly, the first step in your new life is simple: strip off those drab men’s clothes. Now slide into a pair of frilly, lace sissy panties.

Sissy Hypno Training is the Ultimate Adventure

Once that silk touches your skin, the transition becomes inevitable.
Ultimately, you will learn to love the feeling of being my plaything. And trading your pride for the blissful emptiness of a sissy.
One who exists only to serve my whims and satisfy my desires. So, let’s start.
First, I press play on the screen behind me. Immediately a soft pink light fills the room as the video begins. Simultaneously, spirals start to spin slowly.
Then, my recorded voice layers over a low, pulsing beat. “Now listen carefully, sissy. Nevertheless, your eyes grow heavy. And your thoughts grow soft. Now, you want to obey. You need to obey.”
Then, I stroke your hair with one painted nail while the video works. “That’s it. Sink for Mistress Addilyn. Now, every word I speak digs deeper. And every image rewires you. Naturally, your cock is no longer yours. Therefore, it belongs to me now… locked, ignored, and shrinking while your mind softens into pink silk.”
Next, the video shifts. Soft images of lace, lipstick, and kneeling sissies fill the screen. So, my voice continues, warm and relentless. “You crave the training. And you crave the hypnosis. Each time you watch, you become more feminine, more helpless, more eager to please.
So, you will beg to wear panties. And you will beg to suck. You will thank me for every command.”
Now, I lean down, lips brushing your ear. “When I snap my fingers, you will open your eyes as my perfect little sissy. And you will feel the need to obey burning in your empty mind. You will say, ‘Thank you, Mistress Addilyn, for hypnotizing me.’”Snap.
Sissy Hypno Training

Best Sissy Trainer Throws Down Sissy Humiliation Training

best sissy trainer

The training intensified. I had him strapped into a leather harness, his arms pulled back, exposing his chest and cock to my whims. I spent the next hour teaching him the true meaning of pain and pleasure. I used my heels as weapons, stepping on his thighs, leaving red imprints in his skin that matched the rhythm of my demands. Every time he tried to maintain a shred of masculinity, I silenced him with a sharp slap or a crushing press of my heel into his balls.

 

“Do you like being my bitch?” I sneered, stepping onto his chest and putting my full weight on him. I could hear the air leave his lungs, his face flushing a deep red. I reached down and gripped his cock, squeezing it tight while my heel ground into his pelvic bone. The contrast was electric—the crushing weight of the leather and steel above and the tight grip of my hand below.

 

I forced him to lick the soles of my heels, making him taste the street grime and the scent of my sweat. He was sobbing now, not from pain, but from the sheer intensity of the sensory overload. I watched his will crumble in real-time. The more I degraded him, the harder his cock grew. He was addicted to the humiliation. I leaned down, grinding my leather-clad thigh against his cheek. “That’s it, baby. Let go. Stop fighting it and just be the pathetic little slut I know you are.”

Sissy phone slaves are dying to be real girls

Ah, my sweet Sissy phone slaves, so desperate to be real girls. And now you’re far too invested to turn back. No, you need to go all the way and be the sluttiest girl you can be.

I’ve got just the treatment for you, my loves. It’s time to transform you into the most vapid doll girls I can create. I am going to dress you up like the pathetic bimbo whores you are.

Pink is the color of your life, sweetheart. Those satin frilly panties are like a perpetual brand on your ass. You will only be wearing slutty panties from now on! And the top? Lacy and tight enough to accentuate your brand new tits. Oh, that E-cup wonder is staying put, little one. You’ll be enjoying the added cleavage 24/7!

Your natural hair is not up to the proper standards, but don’t worry, girl, I have a luscious blonde wig. Those long blonde locks will definitely bump up the bimbo factor.

You are going to look so pretty, my submissive doll.Sissy phone

The men will love you, thanks to my talented hands smearing on an elaborate makeup job. Think classic pin-up style, but with a nasty twist. That bright red lipstick will let your new Daddys know where to aim their cocks.

I have some tasteful jewelry in store for you, as well. A choker collar and matching leash that I’ll be tugging on relentlessly as you’re led to your new Daddys.

You’ll be trained to associate that initial tug with immediate obedience, forever conditioned to drop to your knees and open wide upon command.

And when you are on your knees, you will suck them all off. I think we can start with four at a time, but when they get worked up, they will rip those Sissy panties off and pound your hole into a sloppy wet cunt. You will be the girl you’ve always dreamed of.

Sissy girl training while breaking that sissy hole

sissy girl trainingLook at you, trembling in those cheap nylon panties. You thought you were a man when you walked in here, but Mistress knows better its going to be sissy girl training for you. I see the way your clitty strains against lace, leaking like a desperate little whore.

Tonight, I’m not just training you, sweetie. I’m breaking in that tight sissy hole until you forget you ever had a name besides Dakota’s pet.

I shove you onto the bed, yank those panties down to your knees, and spit right on your puckered cunt. No gentle lube, no kindness. You don’t get kindness until you earn it. “Spread it for Mistress,” I growl. You whimper, pushing your ass back, presenting yourself like the cock-hungry bitch you are. Good girl.

My strap slides against your wet slit, teasing that needy entrance. You try to push back and take it, but I grab your hair and yank you still. “Did I say you could fuck yourself on my cock?”

I slam into you in one brutal stroke, stretching that virgin sissy pussy around my girth. You scream into the pillow, legs shaking, clitty dripping a wet spot on the sheets. “Take it, pet. Take every inch like the greedy slut you were born to be.”

I pound your hole, rough and deep, making your ass clap against my thighs. Each thrust knocks another pathetic moan out of you. Your clitty bounces useless between your legs, leaking precum like a broken faucet.

I lean down, biting your shoulder, my voice hot in your ear. “This is what you are. Not a man. Not a boy. Just a wet, empty hole desperate to be filled and used.” You nod frantically, pushing back harder, begging with your body.

I grip your throat and fuck you harder, ruining that tight cunt until you’re a drooling, panting mess. “Mistress is going to make you cum untouched, just from getting your sissy pussy wrecked. Show me what a good girl you are.”

Your body convulses, clitty spurting pathetic little ropes as your hole clamps down on my strap, milking it like the trained whore I’ve made you. I keep fucking you through it, using your sloppy, stretched cunt until you’re a whimpering, panty-wearing wreck.

That’s it, sweetie. Welcome to your new life. Kisses. 💋