Category: Best sissy trainer

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.”

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.

Mistress phone sex always has my sissy’s obeying

Mistress phone sex, My little sissy bitch dialed me. The second I answered I ordered him to kneel in that ridiculous pink thong, cage locked tight around his useless clitty. I made him Describe the lock. Is it still sealed? Tell me! He confirmed. Metal clicked. Good.  Now open the drawer. Take out the black plug. The thick one. Lube it heavy. Force that fat thing up faggot pussy. I want to hear every sound you make while you push it in. He pressed the tip against his smooth sissy ass and pushed. I made him go slow so I could listen to the wet stretch and the soft whimper as the thickest part forced his tight ring open. When it finally popped inside he gasped. I smiled. Now the lipstick. Red. Make those lips look like the cocksucker you’re training to be. Coat them. Press them together. Blow a kiss into the phone like the dirty slut you are. He obeyed. Like a good sissy! Hand on the cage. Rub the outside only. No touching the tip. Edge that locked clitty until it’s leaking. Tell me when the drool starts running down the bars. He stroked the metal. Pre-cum was dripping. I kept him there rubbing, gasping, almost crying while I told him exactly what he was. You’re a locked, plugged, painted sissy bitch! You exist to take cock and swallow loads when I decide you’ve earned it. Say it. He repeated the words loudly! I kept him edging ordering him to bounce on the plug, to stick his tongue out, to beg. When I finally let him stop, a long shot of pre-cum hung from the cage to the floor. Clean it with your tongue. Then stay plugged and locked until you call again! Good girl!mistress phone sex

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. ????

Forced Feminization is all your sissy boys want!

Forced feminization

Forced Feminization is all your sissy boys want!

You call me up and BEG me to turn your faggot little ass into my little girl!

Oh, you want to be a sexy whore just like mommy, don’t you?

You want me to dress you up in my lace panties and matching bra.

Force you to shove that pathetic excuse of a cock inside my tiny panties.

If you want to dress like Mommy, you have to act like me too!

You know I go to the streets at night looking for big cocks to suck and fuck.

Well, you will have to be right next to me!

Men pay extra for fag bussy like yours!

These men will eat you up, pounding your ass like a real girl!

And you have to take it with a smile if you want to be just like mommy!

I know your ass will bring in a lot of money! 

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Sissy Phone Boys Love if I Watch Them Take Their First Big Black Cock

sissy phone I love talking to sissy phone boys. And I talk to a variety of sissies. Some I call closet sissies. Nobody knows but us, but they like to dress up in women’s lingerie and fantasize about sucking cock. And I talk to the down low sissies. The sissies who suck cock and even get fucked while dressed like girls behind their wives backs. And I even talk to some sissies who have a full-time mistress in their life. For some it’s their wife. But for others it’s a paid arrangement. Regardless of your sissy status, I enjoy phone calls with all sissy boys.

Last night I talked to a down low sissy. This sissy ‘s wife went out of town recently on a business trip. She returns home Friday. I convinced the sissy now would be the perfect time to finally get some cock. For almost a year I’ve worked with this sissy. She even owns a few of her own butt plugs and dildos. Weekly phone calls for almost a year provided my sissy with the proper sissy training she needed to pop that cherry.

The funny thing is as submissive as this sissy appears for me and big black cock she still wears the pants in her family. The wife seems clueless that she’s married to a pretend man. I’m sorry if you like to wear women’s clothes and suck cock, you’re not an alpha man. You can pretend to be one all you want, but you and I both know you’re a bottom bitch.

Nothing Hotter for a Trainer Than Hearing or Seeing a Sissy Lose Their Virginity to a BBC

This sissy invited somebody over that she met on a gay hookup site. And she wanted me there to hear it all. So, I acted as my sissy’s cheerleader, dominatrix and protector. You can never be too safe on those apps. But nothing went wrong with this sissy encounter.

I even spoke briefly to the black stud who popped my sissy ‘s cherry. Can I tell you how hot it is to hear a sissy scream from pleasure while getting a big black cock up her sissy hole for the first time. That never happens. Now I witness it sometimes with my real-time sissies but most of the sissies who call me live in fantasy land.

But not this sissy. Not anymore. Now that my sissy took her first big black cock in her mouth and her back door pussy, she wants more. This appears how a closet sissy becomes a down low sissy. The wife goes away or the sissy travels and he has a chance to finally get that BBC. And as a BBC sissy trainer, I love all my sissies equally. But I will add that I enjoyed hearing my sissy take her first big black cock. Once you go black, sissy, you never go back.

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.”

Dakota trains two sissies to be whores

Best sissy trainerBe My Fucking Cum Whore

I storm into the room wearing only a slutty micro skirt that rides up my bare ass and a tight crop top “Best sissy trainer” across the front clinging to my perky tits, nipples poking out hard. My two pathetic sissy boys kneel naked, their tiny clits already stiff and leaking. “Strip faster, you worthless cum-dump whores,” I snap, watching them yank everything off until their useless clitties bounce free. I grab one by the hair and smash his face into my dripping teen cunt, grinding hard on his tongue. “Lick my fucking pussy, you desperate sissy slut,” I growl, riding his mouth while I ram two fingers deep into the other sissy’s tight asshole, pumping until he squeals.

Their little dickie clits twitch and drip as I force the first one to suck my swollen clit, then slap the second one’s ass raw with my other hand. “You pathetic bitches live to worship my holes,” I laugh, spreading wider so they both tongue my wet cunt and puckered shithole at once. Their faces get soaked in my juices as I order them to tongue-fuck each other’s stretched asses, moaning and begging while they lick deep. I shove one down on all fours and make the other line up to fuck his gaping hole with his clitty, thrusting and whimpering until I squirt hard into their open mouths, making them gulp every drop. I keep them going, grinding on faces, spanking asses red, and fingering holes until they’re both leaking, gaping, and crying for more of my control.

Peace Loves Being a Hot BBC Sissy Trainer

Being a BBC Sissy trainer who loves making sissy’s dress up as hot sissy women is my passion.  Going all out of course because that is what makes those BBCs get hard and ready to fuck.  They love a hot sissy dressed to the 9s.  The panties to start off, nice and silky. The kind that show off that ass and make it fuckable.  A bra to make you look more feminine. The sexy lingerie that make those BBCs get all worked up.  A wig? Sure. Makes you look more slutty.  The makeup.  The high heels and of course the stockings.

It all adds up to make you primed and ready to go.  I want that big black cock to see you and instantly know they are going to use your sissy fuck holes for their own cocks to get hard. For their balls to tingle knowing they are going to drain their balls into those sissy fuck holes.

The minute you bend over and put that ass in the air, those superior big black cocks that use little sissy holes like yours with no regard. They call you a little faggot as they fuck your little boy pussy (your ass). The way that black chocolate bar stretches out your tight little ass and makes you just a little fuck doll at that point. Pounding away and makeing that sissy faggot ass theirs.

Those BBCs officially own you!

Forced Sissy Training to Be The Best at Serving BBC

When it comes to serving some hot BBC, Forced Sissy Training may be the way to go. This is at least true for a handful of my “guys”.
I am Addilyn, and I have a special kind of clientele. So, the guys who come to me crave to surrender.
Therefore, it is often through my dominance and control that I break them and make them surrender. And submitting is exactly what they will be doing.
Submitting to the BBC with the guidance of me, Goddess Addilyn. And I am your BBC Sissy Trainer.
First of all, deep inside many men is that inner Sissy that craves to emerge. And one of the greatest triggers of the lustful cravings is to succumb to BBC.
Consequently, I start the transformation by stripping you of your manhood. First, I lock their pathetic little cock in tight pink cages. Therefore, denying you any selfish pleasure.
Next, I force you to your knees before my waiting bulls. And your mouth hovers inches from thick black cocks. Thus watering with desperate anticipation.

Forced Sissy Training is a Deep Need

Then, I command you to worship every heavy inch. So, you gag and slobber, learning the taste of your new purpose.
Afterwards, I bend you over my training bench. With your shaved, tight asshole, you are slick and pink, ready to be ruined.
Now, my bulls line up, stroking their massive shafts. And one by one, they take their turns. First deep thrust always makes my sissy scream. Therefore, that stretching of her hole wide in a brutal claiming.
Meanwhile, my other bull feeds her throat. Thus, filling both ends completely. Every hard pump breaks down another layer of your former identity.
Finally, when my bulls have emptied their thick loads deep inside you, my new sissy. Now, I unlock those cages. And I make my sissies clean the cum from each other.
Then, I whisper that permanent truth into their ears. It’s that they exist to serve BBC. Therefore, you exist to worship your Goddess.
And this is your only purpose now is under the rule of the Best Sissy Trainer, Addilyn.
Forced sissy training