Tag: humiliation phone sex

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

 

Tanya loves Humiliation Phone Sex and making you her little Bitch!

Humiliation Phone Sex

Let me show you how good at humiliation phone sex I am.  I’ll treat you exactly like the piece of shit, pathetic excuse of a man you are. 

I’ll dress you up in my sexy clothes as punishment for that sad, tiny little dick of yours.

You want to dress like a girl, then you’ll get treated like a girl. And bad girls get fucked in their asses until they are sobbing and begging Mommy to stop.

So, you better be a good girl or that asshole will be stretched out wide with Mommy’s big black strap-on.

Don’t make me bend over so Mommy can spank you for being bad. If you can’t be good,  then i will have to force you to wear my clothes all the time as punishment. 

2026 is the Year For Lots of Sissy Phone Sex

sissy phone sexI want to see more sissy phone sex with sissy’s feminized and fucked in 2026?  Who is in with me?  First of all, I need to find some pathetic little cocksuckers who are willing to submit themselves to my control. Once I have them under my thumb, it’s time for some serious training.

I will start by making them wear lingerie and high heels around the clock. They will learn how to do their hair and makeup like a true diva. If they resist or complain, I’ll just remind them who’s in charge here – me!

Next up is anal training. These faggots need to learn how it feels when a real woman takes them from behind. So every day, multiple times a day, they will bend over and let me pound away at their tight little assholes with my strap-on dildo until they beg for mercy… which of course won’t be given because that would ruin all the fun!

As for humiliating these worthless cocks… well there are endless possibilities really: calling them names like “slut,” “cocksucker,” or even worse; forcing them into public displays of submission where everyone can see just how much of a sissy whore they truly are; making them worship at my feet while begging for permission before doing anything else – including breathing!

And finally? When we get together with our black friends (who love helping us fuck these pathetic white boys), we can all enjoy watching these sissies take turns getting double-penetrated by two huge black cocks.

…while I sit back and watch with a smug smile on my face, knowing that these faggots are nothing more than playthings for me to use as I please. Of course, they’ll think it’s all about them being “trained” or “transformed,” but really it’s just an excuse for me to live out my most depraved fantasies at their expense.

And when we tire of using them sexually? Well then maybe we can find some other way to humiliate them – like making one wear a diaper while another wipes his ass clean after he takes a shit… now THAT would be truly satisfying!

Mistress phone sex trainer slut Remi

mistress phone sex

 

Mistress phone sex slut Remi trained a brand new sissy girl today. Another closet fag that claimed he had never done anything like this before.

Yeah right! That’s what they all say!

I had that sissy bitch screaming “Fuck me like a slut, Miss Remi!”

The bitch claimed he had never been dommed by a kinky, little mistress.

He sure threw his ass back to take all 8 inches like a pro though. He acted like it wasn’t his first time being held down and having a hard dick shoved up inside of him.

It didn’t take any convincing to get him on his hands and knees either.

Once I talked him into putting on a pair of my lace top thigh high stockings and a pair of my panties, he opened right up!

I put him on his back at first. That cock crazed slut instantly pulled his legs up to his chest like a whore, ready to take that dick!

I pulled the silky panties he was wearing to the side and popped it right into his tight, sissy fuck hole!

He moaned like a whore and begged me to shove it in deeper.

I fucked that slut as hard and fast as I could but that still wasn’t enough for that sissy faggot.

This bitch needed to be flipped over, held down and force fucked good and hard. That’s exaclty what I did.

With his face down in the pillows and pretty sissy ass up in the air, he was begging for it.

I rubbed my nails down the back of his stocking clad thighs. Tickling him softly as I teased his winking sissy fuck hole with the head of my dildo.

I had that bitch rocking back, desperate for more of that cock.

I When I finally shoved it back into his tight, he-pussy, that’s when the bitch started moaning and telling me to fuck him like a slut.

Some sissies are just born to be used like cumrag bitches.

Training new sissy faggots is the best!

Sissy bitch get’s trained with a leash..

BBC phone sex

I like my sissy fucks close, on a leash. I gotta make sure your doing your nasty duty’s and always ready to taking a pounding. I prefer you on all fours with your ass in the air, dressed or not, ready to take that plane that’s landing right into your gaping man pussy. Sound sleezy enough for you boo?

So It’s time Miss Jackie takes you for a walk with the collar, leash and chain. However, before we do, I wanna dress you up like the little bitch you are because you gotta job, on duty you dirty cuck slave. I like to walk my girls in style, little pink panties, pink bras, little bows, and a cute long ass,big black rubber dildo up the ass the same time. Preferably one with a tail so I can kick and pull you in the ass when your not following directions. 

I’m here to humiliate you, make you feel even more unwanted with your inverted cock.

Once we got you looking hot to trot, makeup too, lets go for a stroll and see what that ass can do.

I wanna show you off to the public, let everybody know with a sissy little faggot fuck you are as you walk with that rubber monster cock up your ass, let me give you a swift kick and push. I need to hear you whimper and cry ,beg me to stop. So scream bitch!!

Family tranny training has his perks, but sometimes you get stuck with shit up your ass and it’s my  job to stretch that man pussy as far as it goes. I want you to feel the air between your legs when you wear those tight hose. And also fill it with two cocks at one time.

Taboo phone sex

You’ve been walked with a wide fat can cock far up your sunshine, wide range and a hook, you need to suck it clean after he shoves it deep in my tight hot cookie. Just god damn stay on your knees and use that tongue, your a worthless fuck and I expect you to glisten his balls, and suck the cream dream from my cunt for your desert.  

Mommy caught you in your Sissy Panties. Oh No!

Sissy Panties

 

Oh honey, you look so cute in your little Sissy panties. But I know those are the pair of my undies that went missing a while ago.

Have you been wearing them? Waiting until I’m leaving the house to parade your little faggot ass around the house like you would be my little girl?

 

Well, if you want to dress like a girl, we might as well treat you like one. Maybe Mommy should bend you over and teach you a lesson about stealing people’s panties.

You want to be a little girl, then I am going to fuck you like a little girl. Mommy is going to lube up my strap-on and get your tiny, tight asshole ready to take a beating.

That will teach you not to steal mommy’s panties anymore! 

 

 

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Femboy fuck toy turning into a princess man pussy

Best sissy trainer

Most of you who I talk to are so easy and eager to train. Willing to get dressed up to a tea and look like the princess fuck toy I need you to be. Get out of that suit you wear everyday and put on some panty’s. Feel how soft that satin is when I pull it up your ass cheeks. You bend over backward to see me, hear my voice, begging me to make your pretty like me.

I need a special sissy one that loves to dress up in little panties and bras. That’s how I work. You wanna be a little cunt? Well dress like it too. Shove that pathetic inverted tiny peen you got int them. I’ve talked to a few that have been hesitant but when I insist you call me with a pair on you always bust quick.

My forced feminization is what’s gonna get you fuck up your man pootie honey…

That pretty make up. Eyeliner, mascara and blush, maybe a wig for the final touch. And don’t leave out, my femboy’s wear butt plugs, especially when in training. You’re all pathetic and worthless, you really are.  A perfect slut whore, now a sexy and sultry a woman ready to get her fuck on at the boom boom room, spreading her man pussy wide open for all those random dicks to smash your goey nasty wet fuck hole.

I’ll put you in a long blonde wig or even red it’s your choice. I need you to look a pretty faggot sissy fuck when you’re desirable to men bent over. Your crack is now their snack, yummm! You’ll get those pretty things all ripped up when that big cock gets shoved up your sloppy wet gaping man pussy. I want your hose to split and tear open while you squeal and cry.

Sissy panties

This and BBC strap on’s are all part of my training, cute for the cock, ready for the punch. Throw you on your back and spread those legs wide for big daddy dick. Show fear in your eyes and he squeezes your balls, pulls your hair while he’s balls deep. When your ready to be a bad bitch, hiding the worthless man that you really are class begins when you give me a call.

Sissy phone sex with Miss Remi

sissy phone sex

Miss Remi the sissy phone sex trainer slut is ready to play with you!

Let’s strip you out of those stupid manly clothes and get you into something sluttier!

The cute panties and matching bra is just the start to turning you into a girly whore.

Your training starts the second you get your slut lips around a fat, throbbing cock.

Tasting that precum on your tongue makes that sad, little clittie jump doesn’t it?!

I know a sissy bitch like you can’t wait to feel a thick, girthy rod in your throat!

Rub the front of your panties and tease that pathetic clit while you milk that dick into your mouth.

If you think swallowing up thick, gooey jizz was all I had in store for you, then get ready! You’re about to have those panties ripped off of that sexy, sissy body.

I’m going to hold you down and drill my strap-on so deep in that sissy cunt that you’ll feel it in the back of your throat.

While you’re moaning and rocking back to take it as deep as you can, I’m calling in backup.

My studs are going to surround you and take turns fucking your whore face and sissy pussy at the same time! I can’t wait to see you get turned into a double stuffed, creampie princess!

Cum to Ms. Jackie for the best man pussy spreading dreams

Best sissy trainer

Your ass would look much better baby with a fatty black rubber all lubed up fat Holiday dick up it. Your gaping man pussy makes my creamy cunt pulsating for punishment. All you ever do when you call me is whimper and beg, begging me not to shove this shit up your ass while slapping your pathetic cheeks. It’s all you think about. A man on the outside and a little bratt on the inside.  You’re pathetic and worthless that’s why it’s gonna hurt going in, I promise. And it’s become a habit of all of yours that when I’m doing my wind up before I smack, it’s always, “no no please Ms. Jackie.” 

I just need to work and stretch the fuck out of your prostate and spread that tight man pussy out. You’ve got such a tight squeeze clammy pussy hole, my favorite! I just love stretching  it out like the sissy princess you dream of becoming. 14 inches long, 4 inches wide and he don’t play! I’ll turn that bad boy up to tent just to watch you jerk, demanding you twerk that cute ass in my face, roar! But before we do some fuck boy training there are a few things I need to do. 

Forced feminization is my thing, dresses, skirts, I’ve got all the works..

You’re going to need to put on a lacy one piece with openings for all your holes and pop out that ass of yours and bend boy, touch them toes femboy. When I take my sissy’s slaves out on the town this is what they wear. With boots, heels and a wig, you’ll be the prettiest thing any man has every seen! Dressed up like the whiny weak faggot fuck ready for your asshole to get ripped into and violated. That’s how I roll when your down to get dominated by Mistress Jackie.

Do you have what it takes to embrace your gaping man pussy BBC fucking power?

Femboy training

My big black rubber lover likes his bitches on their back with their legs open wide, so get down low  and get ready for him to implode those large chunks. Let me lube up and rub this giant black cockhead with my spit and swirl it around your sucked up starfish with some rubber band balls.  I don’t want them to bounce while I’m inserting,  no whimpering or crying baby bitch boy. 3, 2, 1 go!

Ass fuck big daddy deep inside you with that girth tip poking out the bottom, time to sit up on that BBC and spread. Smile and tell me what a bitch you are as you dig out your fecla cum spewing…

Sissy Maid Training with Tanya will have you on your hands and knees!

 

Sissy Maid Training

I’ve really become a master at sissy maid training. Let me dress you up myself, a cute maid uniform, thigh-high stockings, and heels picked to match. I choose the prettiest panties for my naughty girl, and underneath them I lock away that tiny, pathetic thing you call a cock.

I love watching you stumble through my place in heels, feather duster in hand, knowing I’m just waiting for the right moment.

“You worthless little bitch,” I say. “Clean the rug. Get on your hands and knees. Now.”

I don’t hesitate. I make you bend over, lift that tight little ass into the air, and I fuck it hard.

I’ll slam this big, thick strap into your tight little bootyhole. God, the sounds of your whimpers turns me on, but you’ll never know that. 

Be my good little girl and make this place spotless. I’d hate to punish you.

 

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