Category: Phone dominatrix

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

 

Forced sissy training with no mercy for my little cocksucker

forced sissy training Forced sissy training, I don’t waste time with soft talk. When I want my sissy ready, I strip my little faggot and throw the clothes at her feet. Panties first tight, lace, crotch cut so her locked up clitty is shoved back and up. Bra next, stuffed if I feel like it. Skirt short enough that it barely covers her sissy ass. Stockings, garters, and heels that forces her up on her toes. My sissy bitch stands there shaking while I watch her zip and clip everything into place. Then the makeup. I sit her at the mirror and take over. Foundation thick enough to hide every bit of stubble. Contour to kill the jawline. Blush high and bright so she looks permanently stupid. Black liner, heavy blue shadow, fake lashes if I want her looking extra used and like the cheap slut she is. Lipstick bright, sticky red that I smear on thick and make her pucker them cock sucking lips. I check the mirror. If it’s not whore perfect I wipe it off and start again until her slutty face is painted like the cock sucking slut I own. Once she’s dressed and painted I point at the floor. My faggot drops. Skirt rides up, stockings stretch, lipstick already shining. I grab the back of her head, shove her face forward, and tell her to open. That red mouth wraps around cock and I make her take it deep and slow at first so the lipstick smears all over the shaft, then harder until she’s gagging and the makeup starts to run. Spit and red streaks down my slut’s chin, tears ruining the liner, while I hold her there and remind her this is what the dress and the full face of makeup are for. She doesn’t get to stop until I say so.

You’re My Bitch in Sissy Panties

Sissy pantiesI dragged you in your Sissy panties, a pathetic little bitch, into my room and shoved you face-first onto the floor. “Get those knees under you and open your mouth wide, you useless cumrag,” I ordered while taking off my panties. My dripping wet pussy hovered right over your mouth. I grabbed a handful of your hair and shoved my dripping cunt against your lips. “Suck it, bitch. Lick up every drop like the desperate cum whore you are.”
Face Sitting and Ass Eating
I turn around and put my ass right on your face, smothering you completely. “Shove that tongue straight up my ass hole and clean it, toilet boy.” Your muffled whimpers vibrated against my rim while I reached back and flicked your locked clitty. “That tiny thing stays caged. You only get to leak when I allow it, and you’ll thank me by swallowing every bit.”
Pissing and More Oral
I shifted forward and let a hot stream of piss flood your open mouth. “Swallow it all, urinal. You’re my personal toilet now.” Once you gulped it down, I shoved my soaked cunt back onto your tongue. “Fuck my hole deeper, slut. Get that tongue working while I figure out how I’m going to destroy your boy pussy.”
Strap-On Fucking
I stood up in front of you, kicked you onto your knees, and made you bend over so you were on all fours, and I buckled on my thick strap-on. “Beg me to wreck that sissy hole,” I ordered, spitting on your winking puckered ass hole. You whimpered and pushed back, so I rammed the dildo balls-deep in your tight ass in one thrust. “Take it, fuck toy. I’m stretching you until you’re gaping and ruined.” I pounded you harder, slapping your ass bright red and twisting your nipples while you cried out. “Scream louder, bitch. Let everyone know a teen owns your worthless ass.”
Cleanup and Degradation
I fucked you until your legs shuddered, then I bucked the strap-on free of your wrecked ass and scooped the mess from your gaping hole. “Open up and eat this, cumdump. Every fucking drop goes down your fucking throat Bitch!”
Final Domination
“On your back, sissy. I’m riding your face until I cream all over you.” I crawled on top of you and my clit against your tongue. “Lick faster, you broken fuck toy. Make your mistress cum while you choke on my cunt.”

Femboy Training is easy when you are a Sissy Bitch!

Femboy Training

Femboy Training is easy when you are a Sissy Bitch!

You come to me as a weak, pathetic man begging to be turned into my little girl.

You are a sad excuse of a man with that small ass cock, and you’d be better off as a girl anyway!

Your pathetic faggot ass has been yearning for cock.

Mouthwatering at the thought of a man with a big black cock bending you over and fucking you.

I’ll be treating your ass like the tight little hole that’s never been stretched before.

I know how bad you want it, just admit it!

Youd love to be treated like a streetwalking whore getting fucked by any man that walks by!

Your small dick is leaking at the thought of being used!

See More on Blue Sky & Follow Me!

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

Sissy Training Requires a Woman Who is Equal Parts Sissy Trainer and Dominatrix

sissy trainingI enjoy sissy training. And a lot more than I ever thought I would. Before I started doing online training and phone sex calls, I worked as a professional dominatrix. And I made thousands of dollars a week putting losers in their place. But my sissy callers seem similar to my submissive, beta boys. They share many characteristics.

And a sissy trainer is still a dominatrix. She may be a mommy, or she may be a coed, but any woman who trains sissy boys remains in control and superior to her clients. Men who seek out a sissy trainer, or dominatrix are submissive men.

Sometimes I combine my skills when I’m dealing with a submissive sissy boy. Most sissies seek a sweet loving mommy who understands they want to wear panties instead of boxer shorts. Or who understands that they think about servicing cock sometimes too.

Yet, some men want not only a sissy trainer, but a phone dominatrix too. When Lewis called me, he explained what a bad disobedient little boy he’d been. The man got caught shoplifting panties. He’s a wealthy man who could afford thousands of panties, but he stole them because he seemed too embarrassed to buy them.

So, I called him a dumbass. Men buy their women panties all the time. In fact, I think more men buy lingerie than women do. So, anybody working in Victoria’s Secret will not think twice about a man buying panties unless he’s asking to try them on.

Most Sissy Boys Need Equal Parts Dominatrix and Sissy Trainer

So, Lewis seems like a masochist. He wanted punishment for bringing shame to his family. I googled him. Sure enough, he made the paper. An investment banker who gets arrested at the local mall for stealing six pairs of panties will make news in a small town. Although I know he won’t do any jail time, his family now knows he likes panties. I wanted to punish him just for being a dumbass.

Honestly, I wouldn’t have minded being a fly on the wall, listening to him explain to his wife why he shoplifted six pairs of silky panties. She thought he stole them for another woman. He would rather his wife think that he cheated on her than admit that he wants to wear panties. Once again, dumbass. I made him put on a pair of sissy panties and whip himself with a belt.

As he whipped himself, I made him call himself a dumbass repeatedly. Plus, I made him send me some pictures of what his body looked like with the welts from the leather belt. I know that sound. He really did flog himself with a belt.

Lewis is an interesting client. Wealthy. Fallen from grace. A sissy. And a submissive man. Oh, and a complete masochist too. But he called the right woman. I knew how to punish him for being a dumbass and imploding his world over panties. Plus, I knew how to dress him and train him to be a good sissy. Our relationship just started. But I’m equal parts, sissy trainer, and dominatrix and for some of you, that’s exactly what you need.

Dressed Up In Dirty Sissy Panties

Sissy pantiesMy good boy Joey loves to play with me in his Sissy panties, everytime we chat he gets all dressed up in his mommy and sisters dirty panties for me, I have him dump out their hamper, finding the dirtiest panties, filled with cum stains, some shit stains too, I always get him to smell and taste them before he slides them on his tight ass, his big long cock cant fit in the thongs, its too long and fat, we normally tuck his meaty memeber into a sweaty gym sock.

Joey stuffs his bra with dirty panties and cum stained stockings. I make him crawl to his mommy’s room like a good boy to put on his makeup and find something sexy to wear; today he dressed in a mini skirt and cum stained thigh high stockings.

Once all dressed and pretty, I sent him to find his mom and sister’s cum covered dildos, the biggest one for his tight asshole. My good boy puts on a good show every time to please me. I tell him how to ram his ass with his sister’s dildo covered in her juices; he really gets turned on when I tell him how his mom and sister are watching him on camera as he is dressed up in their stinky underwear. He shoots a huge cum shot in his sister’s sweaty thong like a good boy.

Best Sissy Humiliation training

sissy humiliation trainingI slap his cheeks, leaving bright red prints that make his lips tremble sissy humiliation training starts now. “Open wide, toilet.” I shove two fingers past his gagging lips, feeling his tongue sputter as I pump them in and out, mixing my spit with the drool dripping from his chin. “Suck it clean, you cum‑guzzling whore.” He obeys, cheeks hollowing, eyes rolling back as he gags on my fingers, his useless clit throbbing against the tight pink cage.

I yank my hand free, leaving a glistening strand of saliva stretching from his mouth to my knuckles. “Time for the main course.” I flip him onto his back, legs spread wide, his hole already gaping from the earlier abuse. I spit a thick glob directly onto his pucker, watching it sink in before I slam my strap‑on home dry, balls deep. His scream tears from his throat, raw and broken, as I begin to pound—fast, brutal, relentless—each thrust driving the air from his lungs in wet, choking gasps.

“Feel that plastic cock stretching your worthless ass?” I growl, leaning over him, my tits swinging inches from his face. “You’re nothing but a fucking urinal with a hole that loves to be filled.” I slap his thigh hard enough to bruise, then grab his hair, forcing his gaze to the filthy floor beneath us. “Lick it up, slut. Every drop of spit, piss, and precum you’ve been leaking.”

Good Fucking sissy bitch

His tongue darts out, lapping at the viscous mixture, shuddering as he swallows his own shame. I grind harder, feeling his walls clench around me, his cock jumping uselessly in its cage. “You love this, don’t you? You love being treated like a piece of fucking meat.” I bite his nipple, leaving a crescent mark, and whisper, “Say it. Beg for more.”

His voice is a wrecked whimper: “Please, Mistress… fuck me harder… use me…”

Final Fuck

I grin, slamming in one last time, grinding as I flood his ass with hot spurts, holding him pinned as he chokes on another denied orgasm, his body trembling, his soaked panties darkening further with fresh leaks. I pull out, wipe my cock on his tongue, and stand. “Clean the floor. Then thank me for not making you eat the shit off my boot.” He scrambles, tongue dragging across the grime, moaning degraded bliss as I watch my human mop do exactly what I told him to.

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. 💋

Sissy Training Starts With Tears

sissy training

 

I don’t do introductions; I do submissions. My new toy was already shaking, stripped bare and kneeling on the cold floor of my studio. I stepped into his line of sight, the sharp clack of my six-inch stiletto heels echoing like a gunshot. I was poured into a skin-tight black leather corset that pushed my breasts up and a mini-skirt that barely covered my ass. I looked down at him, my eyes cold, while he stared up at my towering heels with a mix of terror and hunger.

 

“Look at them,” I commanded, my voice a low growl. I pressed the pointed tip of my heel right into the center of his chest, pushing him back until he hit the wall. I could feel his heart hammering against the leather sole. I didn’t give him a second to breathe before I slid the heel down, dragging the sharp point across his ribs and stopping right at the waistband of his dignity.

 

I reached down, grabbing his chin and forcing him to look at me. “You aren’t a man in here. You’re just a piece of meat for me to mold.” I shifted my weight, grinding the heel of my shoe directly into his soft groin. He let out a choked gasp, his eyes rolling back. I didn’t stop; I twisted the heel, applying just enough pressure to make him whimper. I loved that sound—the sound of a man realizing he no longer owned his own body. I leaned in, the scent of my leather gear filling his nostrils, and whispered, “By the time I’m done, you’ll beg to be my little sissy.”