Category: Taboo phone chat

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.

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 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.

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.

The Best Sissy Trainer Sucks Cock Too

best sissy trainer The Best sissy trainer treats her pets like royalty. I sometimes make my potential sissies feel like royalty before I pimp them out, turning them into sissy cum holes, bathing them, washing them from head to toe, dressing them up in sexy slutty thongs, making them feel super sexy, lips covered in red lipstick, long blonde wigs, and sexy heels.

I am dressed sexy as fuck, wearing a satin one-piece crotchless outfit with heels and a garter belt to match, my big black strap-on already in place.

Grabbing my sissy by the cock, pulling his thong to the side, sucking that clitty, licking his balls softly, making my way down to his taint with my warm wet tongue, his asshole licked and sucked, my two fingers in his asshole, stroking his clit. 

Once I get him all stretched out, I shove my fat dildo in his asshole. When I am balls deep inside his ass, my big black bull slides his nigger cock in his ass, both of us balls deep in his sissy asshole, giving him every inch of cock we have.

When my bull fills his asshole with cum, I keep fucking his hole as the bull shoves that big nigger dick down his throat, making him clean every inch of his dick with his sissy mouth.

Domination Phone Sex bring Sissy boys to their knees!

Domination Phone Sex

Domination Phone Sex bring Sissy boys to their knees.

The only way to cum is to dominate these men myself!

If I want to squirt and moan, I have to do all the work myself.

I will straddle your lap and hold you down forcibly.

Guess someone has to show you how to fuck a pussy properly.

I’ll be riding that cock, up and down, squeezing my pussy tight, milking the cum out of you!

You can finally feel what it’s like to make a woman cum.

Finally, man enough to have that pathetic, useless cock be used.

Looking at the stupid face you make once I get you cum everywhere.

That’s all you are good for: being used for your cock.

It’s not even a big or thick cock, but it’s mine to control! 

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Peace Takes Her Sissy Girl Training Sex To Zoom

Alright, it’s time for a special sissy girl training treat. I get to watch you on Zoom, you don’t watch me but I need to see your pathetic sissy slut selves. It goes something like this..

As each one of my pathetic slaves obeys and exposes their chests for inspection, I can’t help but feel a rush of power course through my veins. None of them have developed anything worthwhile; they are all just as flat-chested as ever. Disgusted by their lackluster attempts at being women, I continue with the next part of today’s lesson – dressing up in lingerie like the good little sluts they are meant to be.

“Now then,” I say while watching on screen as each one struggles into lacy bras and panties that barely cover their tiny cocks or plump asses “make sure those stockings aren’t too tight around your dicks.” My eyes roll back in amusement when one tries desperately not to reveal his hard-on underneath his silky garments – such weaklings these men truly are! But it only makes me want more from them…and myself too because damn does this turn me on knowing how much control i hold over these pitiful creatures who crave nothing more than becoming submissive females beneath my command..

Next comes makeup application which most fail miserably at doing correctly due mainly because none possess even an ounce talent when it comes beauty regimens designed Alright, you little sissy boys. It’s time for our weekly Zoom call where I get to see how well you’ve been practicing your feminine skills! First things first, let me check if any of you have grown some tits yet. Strip down and show them off!

As each one of my pathetic slaves obeys and exposes their chests for inspection, I can’t help but feel a rush of power course through my veins. None of them have developed anything worthwhile; they are all just as flat-chested as ever. Disgusted by their lackluster attempts at being women, I continue with the next part of today’s lesson – dressing up in lingerie like the good little sluts they are meant to be.

sissy girl trainingI have plenty of time to teach them how pathetic they truly are when it comes down doing something right without any guidance from me whatsoever!

Sissy maid training whore now is my own Cinderella

Sissy maid training Sissy maid training sluts have to work extra hard for what they want. I am not going to be easy on you at all.

You’re here to serve me, you understand? If you ever want to pass and be desired by a man, then you must listen to me.

You are my Cinderella, and you will clean me up!

I have a lot of boyfriends, and they all cum so much. I know you are hungry, probably frothing at the mouth and clitty.

Get that fetching maid costume on. You must look the part to play the role. Once you are dressed, get on your knees. You are not allowed eye contact; you don’t deserve it.

Lick my fucking feet, you stupid fucking faggot. I know you feel so good at the bottom of the barrel; it’s where you belong. Slide that tongue up into my cunt. It’s filthy and needs a good tongue cleaning. Cinderella, how does it taste?

I bet it tastes like pure jealousy because you know you will never be a beautiful woman like me. However, if you do a good job licking me clean, I will allow you to be fucked like a girl, even though you are a faggot. My boyfriend’s ten-inch cock will fuck you through your soaking wet Sissy panties and destroy you completely.

 

 

 

 

 

 

 

 

 

 

 

Sissy slave training makes you into your true form

Sissy slave trainingFrom the moment you pleaded for my special Sissy slave training, I knew we were gonna have an absolute blast transforming you into a cock-hungry, cunt-worshipping girlie.

First, I need to make sure that clit cage is nice and tight.

I mean, we wouldn’t want your clitty to explode too fast. Even when it’s all locked up, it’s just dribbling sissy cum. I can’t wait to watch it shrink down to a cute little clit as you get your hole wrecked.

Once I sink my claws into a bussy, it’s like a magic spell – they’ll be skipping around in Mary Janes and pigtails, eager to please my every whim.

I order you to take Daddy’s lollipop all the way down. I want to see gagging, I want to see drooling. I want you to struggle to fit it down your throat, and you’d better get it that way.

If not, I will expose you. Maybe that would be the best thing for you anyway. I can burn your life down, and we can start anew! You know you don’t want to live the way you are now. You are not a man. You are my girl, and I feed you cock.

Including deepthroating my boyfriend’s huge, fat cock. Don’t you want to be a good sissy cumslut for me? Then you’d better get to sucking his big black cock and thank me for letting you get a taste. I see by the way you are sucking it, you are going to need a lot of Sissy training, you silly bitch. Good thing my boyfriend has friends with big dicks just like his.