Category: Sissy humiliation training

Sissy Maid Training For a Married Closet Sissy Boy

Roger Needed Sissy Maid Training. He is one of those little sluts that likes to be dressed in petite little outfits and given tasks. A Honey Do list. I put him in the perfect little French Maid outfit. Underneath that next to nothing skirt, the cutest pair of red silk panties, restricting his hard cock. It was so fun getting Roger Ready.

Craving Cock sucking, but You are the one on your knees?

He even went great lengths to perform each tasks I asked of him. I wanted him shaved completely. Not just manscaped cock and balls. I wanted those legs hairless, as well as his chest. I waxxed his body myself. To get away with it, Roger signed up for swim lessons. To keep his little sissy secret from his wife, Rog even signed up for swim lesson so he could keep that buttery smooth chest and silky legs. His cock would drip while we waxed his body.

Naughty Little Dick Loving Diva

I started by Making him Dress completely and while cleaning my house from top to bottom he would wear a vibrating but plug. I held the control to turn it off and on, make it buzz and pulsate. The best thing was that it had a little dial, so I could strengthen the intensity of the pulse and vibration. His butt hole was mine, and his cock belonged to me. Maid Training was just what he needed.

Rogers wife will Never Know

After and I mean only after, All tasks were completed would I dress in the sexiest lingerie. I’d also wear my harness and lock a nice always hard and ready, 7 inch dong in there. Watching Roger on his knees, he loved for me to ask what his Beautiful, Loyal Wife would think if she saw my fat hard rubber dick in his mouth. That’s when I took pictures. You never know when you might need to blackmail a little closet Sissy boy.

He always had to suck it good and deep, depending on what he did with that cock and how well he cleaned my house, I would ponder using his tight little starfish.

Should I fuck Him? or maybe I should fuck you instead! Let’s Bring that Fantasy of being dressed like a slut, and completely fucked to a reality, sweetface……

Sissy Maid Training

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Sissy Phone Sex Dom Needs a little Bussy to Fuck!

Sissy Phone Sex

 

Sissy Phone Sex Professional, Tanya, needs a really good girl to give some punishment to!                                               

Can I dress you up in little Dolly clothes with big puffy skirts and little stockings underneath? Be my little girl who knows how to take Mommy’s dick and shut up. 

I want your ass in the air and face down into the carpet like the worthless bitch you are. I am going to pull those little panties to the side and stick my biggest strap on in your teeny tiny bussy.

I need to watch as your asshole stretches out around my big dick. All I need to hear is you whimpering and crying at the pain of me fucking you all night long.

Only dirty girls like you get to be fucked like sluts.

 

More Sissy Shit on X! 

Humiliation Phone Sex Makes Peace A Hot Wet Mess

Humiliation phone sexHumiliation phone sex may come at a cost, but only to your ego. You pathetic little faggot, get your scrawny ass over here and start dressing up like the worthless cock-sucker you are. I am your Mistress Peace, and I want to see those silky panties on your skinny legs, and make sure they hug your tiny balls tightly. Don’t even think about touching that little clitty girl of yours; it’s mine now, and I’ll decide when and how it gets played with. Now move!

Being an Obediet Whore For Your Mistress

Good boy. Now, let’s see if you can handle these heels without falling on your face like the little sissy slut that you are. And don’t even think about complaining or trying to act tough; I have plenty of black friends who would love nothing more than to help me fuck a sissy boy like you in the ass until it hurts so good. Remember, this is all for my entertainment and pleasure…and theirs too!

Sissy Sluts Of Peace Must Look FabulousHumiliation phone sex

You look absolutely stunning dressed up as a woman, now come here and sit next to me while I do your makeup so we can go out looking fabulous together

Now, let’s get you looking like the pretty little sissy slut that you are. You know, I have a special surprise for you tonight. My black friends are coming over and they can’t wait to see how well you’ve been trained. They’re going to love watching me fuck your ass with this dildo while you suck their cocks like the good little cocksucker that you are.

You better be ready to please them because if not, there will be consequences…and trust me, sweetheart, you don’t want that. Now open up those lips and show me what a good girl looks like!

Sissy girl training teaches you to blow the right way

Sissy girl training, my dear, you want to learn the art of pleasing a hot, fleshy cock. You know the thing you don’t have between your legs, but you’re constantly drooling for them. Mommy knows what her little sluts need.

Hardcore discipline and a cum stained face.Sissy girl training

It all begins with a clear understanding of the orders you receive. Your Mistress dictates every move, and it’s your sacred duty as a sissy to follow my commands without hesitation.

So, the moment those authoritative words leave my mouth, your body should spring into action, like a well-oiled machine.

I do remember the day you came to me, begging me to teach you how to suck cock. And I told you learning how to blow the right way takes dedication, didn’t I?

So don’t be surprised when you have two fat cocks down your throat. See, Mommy is trying to destroy your gag reflex. If I want to pimp you out, I need to get your throat nice and wide for all the black cocks you will taste.

I’ll be there to hold your hair back. I’ll be guiding your head into the perfect position. You’ll try to lift your head, since it will be so hard to breathe with cock in your mouth. But I won’t let you.

Don’t disappoint your Phone dominatrix! Mommy wants to hear you gag and choke on cock, and right before you pass out from lack of oxygen, that’s when I’ll give you a little break.

All my boyfriends love making a bimbo slut like you, crying from choking on dick. That discomfort and shame have to be earned before you truly become one of my sissy sluts. Understand that all of your holes will be met with brutal force so that you can be fucked into a proper bitch.

Femboy Training with Tanya – Let her dress you up like a whore!

Femboy Training

 

When I first got into femboy training, I didn’t set out to change my guy, I just wanted to have my nasty little fun with him. 

I showed him how pretty he’d look like a whore – so I dressed him up in my lace panties, stuffed a bra, and threw on some red lipstick. 

God, you look so sexy dressed like a slut, I think I need to see you stumbling around in my heels. Go over to the kitchen and make us drinks. I want to watch your ass sway as you walk away. Be a good little girl for mommy. 

Good girls get surprised. Like mommy’s biggest strap-on stretching your tiny little tight asshole wide open. 

You just look so good as a girl. I need to fuck you like a girl. 

 

Find a trainer on X! 

Humiliation Phone Sex Brings Out The Sissy Faggot you try to Hide

Humiliation Phone SexHumiliation Phone sex brings out the vulnerable little bitch boy that you try to bury deep inside. You know the You that craves to be dressed like a little fuck doll. The one that wants to be dragged out to the Kink clubs and used by all my freaky friends. Haha! The One that wants to  do freaky faggot shit Like licking cocoa starfish’s and sword swallow big Black bats all night.

Sucking on dirty little shit holes makes you a bottom feeder right?

I plan to make you suck so much cock your throat will feel empty without it. Stuffing your asshole so full of Dick, you could gape and prolapse. Don’t worry, think I can’t make you my little sissy fag? Ill take some hot Little nap shots of you lovin on the D.  Would you Love your busted asshole showing on the outside? Id love getting that anal sleeve fucked good and hard. Get a few Fat cocks to push that lapse back in, just like new.

Dirty Faggot Fuck Boy, You’ll be Used By Me and My Friends

Passed around like a party favor. You’ll be a hot little Piece of fuck meat for me and all My Strap on wearing Size queens. We love big dicks that stretch little holes wide open. Blowin’ that Back Out. Twerk that tooter and show us whatchu werkin with!  Do Trix on the Dick!

Silly Faggot, Dicks are for Chicks!

Mistress phone Sex will Put you in your place. That’s why Its my Plan to turn you into the prettiest sissy boi ever. I want all my bitches to get that good good. I hope all your holes are ready to be filled to the brim with strange spunky sperm. You wanna be a Hoe, you gotta do some hoe fuck shit. Get up on my big Ole Dildo and Ride it. Show me you know how to fuck. Smile for the Camera Cum Slut, this ones for mama..

I gotta show her what a bitch she raised.

Mistress Phone Sex

Wanna See More Bad Bitches?

Pathetic and worthless, lets go for a nasty walk on your leash

Femboy training

It’s time to degrade your dumbass. Sissy fuck wants to just be a full time cunt cleaner. You’ve got that mouth that’s only worth one thing for constantly sucking all the white filled fluid flowing from my tight fanny. Your other job is throating and fucking thick dick down your throat, remember, I’m in charge honey. I wanna take you out for a stroll, let you piss on the sidewalk like a good little doggie. Leather bound, leashed up with adorable pink sissy bitch panties on. Little girls like you belong to me, submissive to my commands.

We’ll walk you into black room at the local black room swingers club. Show you off to all the men that’ll use your man pussy as their little fuck toy. With so many on lookers rubbing their cocks and wet tootsie’s, getting off on watching you getting tortured, stretched, you man gap getting absolutely wrecked.

On all fours with your pretty laced panties pushed aside, we’ll take you to the good ol glorry hole dungeon. Every hole has a sloppy surprise, so bend over you little bitch. Rub and grind while your down there or I’m cracking my god damn whip boy!

Femboy training hurts baby….

Your worthless cuck need to munch on some hairy ass. I wanna make sure you get your tight creampie twinkie used, violated. and abused. If I hear your whimper and cry it’s another beat down for you. Your pounded and smashed, I can see your sissy asshole skin getting twisted in your pink panty bunch. You belong to whomever wants to spread your fuck hole while we sit and watch.

And we’re never done till you do your main job and suck on some soaked up stretched just fucked twat while you got a nice big meaty BBC inside you, balls deep. rocking you back and forth, his hips smashing up against you, his big cock disappearing up your wrinkled tuna roll.

BBC sissy trainer

You’re the life of the pathetic public panties party without knowing it, your munchkin man’s pussy bitch, pencil penis is rock hard, leaking little cum shots as your violated leaving moist femboy clammy. 

Humiliation Phone Sex with Zuri Breaking You Completely Down

Humiliation Phone Sex

I sit back in my chair, phone in hand, smirking at how eager they are to please me. They don’t even realize how far I can push them, how much I can make them squirm just with my voice. Humiliation Phone Sex… that’s what I’d call this, but really, it’s about control, about breaking their perfect little egos down one command at a time.

“Do you think money buys you respect?” I snap, letting the silence hang for a beat. I hear them shift, hear the catch in their breath, and I grin wider. “I don’t care about your accounts, your yachts, or your fancy cars. You exist to listen to me, to follow me, and right now, you’re nothing without my approval.”

Their desperation is delicious. I tell them to strip slowly, every finger, every toe, like I can see them even over the line. I make them confess, out loud, how pathetic they feel under my gaze, how they want my attention, my control. And they obey. Every. Single. Word.

I tease them relentlessly, letting them imagine what’s coming next, pulling them tight with just my voice. I drag their egos through the dirt, laughing softly at how fast they crumble. “Tell me you’re worthless without me,” I demand, and I hear the shaky whisper, “Yes… I’m worthless…” My smile stretches, satisfied.

They beg without shame now, eager for more, and I push them even further. Instructions, tasks, little games of obedience…. I make them grovel verbally, trace their bodies with words, and shiver at every command I give. They’re powerful men in the world, sure, but with me? They’re mine to toy with, mine to break down and rebuild however I want.

By the time I finally let them rest, I hear the ragged breaths, the trembling, the quiet admissions of how completely I own them tonight. I hang up, smirking, knowing I’ve left them desperate, flushed, and utterly undone. Power tastes this sweet every time, and I can’t wait to do it again.

Phone Domination is The Best For Closet Sissy Girls

Phone Domination for sissy girls to lose all power and control, to me, Addilyn. When you called  me you quickly surrendered all control. During Business hours a CEO of your own company, barking orders at boardrooms full of men who feared you. But the moment you dialed my line, voice shaking as you whispered your secret fantasies. Right away I knew you were just another fragile little boy desperate for Mistress Addilyn’s control.

Phone Domination Under Mistress Addilyn’s Control

First off I laughed softly into the phone, my voice velvet and venom. “Strip, bitch. Right now. I want you naked and on your knees before we even begin.” Of course you obeyed instantly, cock already twitching.

The first lesson was simple: panties. I made you order the sluttiest pink lace thong online while I listened. The whole time mocking how hard you got sliding it up your legs.

As I teased and mocked you “Feel that fabric hugging your pathetic clitty? That’s the closest you’ll ever get to being a real man again.”

Night after night, I wove my web. I trained your walk—hips swaying like a desperate whore in the heels I commanded you to buy. Then I taught you makeup: cherry-red lips perfect for wrapping around cock, smoky eyes that scream “use me.”

My big, bouncy breasts filled your screen during our cam sessions, making you whimper with jealousy as I squeezed them, reminding you you’ll never have anything so perfect.

First, I broke your ego slowly. Next, I forced you to repeat after me: “I am Mistress Addilyn’s sissy slut. And I live to serve cock.” Each confession chipped away at the corporate mask until only the eager cock-whore remained.

The final test came when I brought in my bull—a real man with a thick, throbbing cock. You knelt before us on cam, thong soaked, begging to watch him fuck me first.

Kneel Before Mistress in Sissy Panties

I rode him reverse, my perfect tits bouncing while I stared into your eyes, laughing as you stroked your caged clitty.

Then I gave the order: “Suck him clean, sissy.”

Finally you leaned in, lips trembling, and took your first real cock—gagging, drooling, eyes watering as I praised you. “Good girl. This is what you were born for.

”When he came down your throat, I smiled, my gaze locking onto yours—my ultimate reward.

You swallowed every drop, liberated, intoxicated, finally free under my control.

Welcome to your new reality, my pretty little panty-wearing cock whore. Mistress Addilyn is very, very pleased.

Phone domination

 

Sissy Phone Sex Zuri Dominates and Commands Her Obedient Men

Sissy Phone Sex

They kneel the moment I enter the room, eyes lowered, backs straight, waiting for permission to breathe. I remind them why they crave me, why they sneak away from their boring, obedient lives to kneel at my feet… this hunger they feel is what Sissy Phone Sex only hints at, but what I deliver in flesh and authority.

I circle them slowly, heels clicking, letting the silence stretch until their need grows unbearable. These are grown men, husbands with rings hidden in their pockets, men who pretend to be powerful at home yet melt the second I look down at them. They cheat not because they’re weak… but because they’re starving for control, and I am ruthless enough to feed it.

“Eyes down,” I command, and they obey instantly. I don’t touch them yet. I don’t have to. My voice is the leash. I tell them exactly how to kneel, how to hold their hands, how to present themselves for my inspection. I mock their trembling, praise their obedience, and remind them who they belong to when they’re in my space.

They crave my approval more than affection, more than release. I make them confess… who they lied to, who they left at home, how desperate they were to be here with me instead. “Now who wants to get spanked first?” I ask them loudly. “Of course me your favorite faggot” one yells in the back of the room. Every word tightens my grip on them. I make them repeat it until shame turns into arousal and obedience turns into devotion.

I pace in front of them, issuing instructions with sharp precision. “Slower. Straighter. Better.” Each correction pulls a reaction from them… gasps, shivers, quiet moans they try to suppress. I don’t allow silence unless I demand it. I don’t allow movement unless I give permission. They exist to respond.

I lean close, letting them feel my presence without touch, reminding them that their secrecy, their cheating, their need to kneel all leads back to me. I don’t care who waits at home for them. In this room, I am the only authority that matters.

When I finally step back, I leave them exactly where they belong… pliant, obedient, and aching for more. I don’t reassure them. I don’t soften my tone. I simply remind them they’ll return, because once a man kneels for me, he never forgets who truly owns his obedience.