Category: Best sissy trainer

Femboy Training is What’s In Store For The New Year

Femboy training is certainly in store for you this coming year! As a sissy dominatrix I thrive on training men to be sissy girls.

I decree 2026 the year I strip away every shred of your manhood and forge you into my perfect femboy slut. As your merciless sissy dominatrix, I live to shatter cocky men like you and rebuild them as simpering, cock-hungry little girls.

Femboy Training is Your New Years Resolution

And you exist only to please Big black Cocks. In fact I waste no time. First off, I command you to shave that disgusting body hair smooth—every inch. Then I force those silky pink lace panties over your worthless clitty.  Now feel the fabric tease your skin while your cock betrays you. Imagine leaking like the desperate bitch you are. Next, I lock you in chastity. 

Understand that your orgasms belong to me now. When You throb, drip, and beg, I will just laugh. All while I hold the key and laugh at your frustration.

Then I will drill you in heels until your hips sway like a cheap whore. With your ass arched and presented for use. When You stumble. I punish you. You improve. Only then I reward you with a smirk.

And I train that greedy mouth every single day. When You kneel before my thick strap-on, you understand it’s to train you. And how you choke on it, gagging, drooling, eyes watering as I grip your hair and ram deeper.

“Swallow it all, sissy,” I growl.

Obviously, You obey because you know I own you. With skill I paint your face myself—slut-red lips, heavy liner, long fake lashes.  When you stare at your feminized reflection and whimper, I smirk some more. 

Of course Your caged clitty strains harder. Pathetic Then comes Mid-year, I dress you head-to-toe in stockings, garters, and a frilly maid uniform. As I parade you live on cam for hundreds to mock and admire. Like a good slut You curtsy, serve, and thank me for every degrading order.

The ultimate test of the Best Sissy Trainer? 

It’s when I bring in a real man—a hung bull. First You watch him claim me, then I shove you to your knees. Next You suck him eagerly, tasting superiority, while I lean in and hiss,

“This is your life now, femboy. Cock is your god.”

So You finish the year broken, grateful, and utterly mine—begging for more humiliation. Now be a good  slave, Kneel and message me right now.  Tonight I start your destruction.

Disobey, and I ignore weak boys forever.~ Your Sissy Dominatrix Addilyn

Femboy Training

Femboy Training gets Twinks Fucked in their Stinks

Femboy TrainingFemboy Training is what you need! A Sissy Faggot Like you would be perfect for me to dress and prance around all my Thick Cocked Boytoys. I think Ill start By Having you Give Hand and Suck Jobs on Fleshy Fuck Knuckles. You are To Serve these Cock and Sacks your tongue and holes at every command.

Silly Faggot, Dicks are for Tricks- so Do Some!

Lubing your shit hole cunt up with this creamy vasoline, it sticks and lasts. Goes a long way for all the rod you are gonna ride, and buss it open for. Faggot Flamer. Let your Freak Flag fly little fem fuck. I want you to beg for the dick, show it what a good girl looks like when she will do naughty things to get her fuck holes gaped. First, slide your hand up and down that dick. Your Pathetic ass has to start off somewhere. Wacking off  Willies and sloppy suck jobs are your new beginnings.

I want your face fucked like a cunt, and slobber and snot pouring from your nose. Better learn to choke like the cock sucking slut you were always meant to be. Blow that shit out and suck like a psychopath! Gurgle and gobble the dick like you are possessed, all the way down to the Full Ballsack. C’mon Baby I got Faith in Fag bags Like you!

Then we going to throw dat ass in a circle, and do tricks on the dick! Slam your fart box all the way back on that big shaft. Show them you can take a big ole piece of man meat. Dirty Little fem Fux like you are a big Ole Burly Bears Dream. Wanna be a cubby? Get taken care of by that cock, using your sweet candy ass to make him cream deep inside your shit schute?

Do it for Miss Bri Baby, Nothing makes my pussy wetter!

Click to Bring out the freak!

 

 

 

 

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!

Sissy slave training turning men into sluts

sissy slave training

Sissy slave training, I can honestly say, is so much fun. I love taking a manly man and turning him into my pathetic little sissy bitch. Especially high-class men, like captains, pilots, or even corporate bosses. Either way, I know I will make them crumble and cave.

Making them crave and want to be in their tight little panties all the time. Which in training panties are an everyday thing and will replace any manly boxers you think you’re going to keep. Nope, my little bitch boy will do whatever I tell him to. Including watching me throw away all his many boxers and swimsuits. Replacing it with tiny sissy thongs and bikinis.

They have no choice but to send me daily check-ins. Part of being a good little sissy slave is telling your mistress and showing her how well you can follow her orders. Sending me daily pics and them begging for me spit to hit their worthless, greedy tongues. 

Training is complete once I know that they would rather be a sissy bitch than a man. Because that’s all they were meant to be for me anyway. A good little sissy that mistress plays with like a little sex rag doll. Once they can’t stop thinking about it and only crave it. Then that’s when I know they are forever mine, and the training has made them realize who they belong to.

Mistress Phone Sex with Zuri Seducing You All Day and Night

Mistress Phone Sex

The second he stepped through the door, I felt that familiar thrill coil in my stomach. Dressed all in black, my whip in hand, I let my eyes roam over him, savoring the way he couldn’t stop glancing at me. Tonight was ours, a secret little escape where I got to be bad, and he loved every second of it.

We’re about to indulge in some Mistress Phone Sex, though tonight isn’t just about whispers over the phone. It’s the anticipation, the stolen touches, the tension that builds because he’s handed me his weekly allowance to keep his secret… and oh, I intend to make him earn every moment of it.

I paced slowly, hips swaying, letting him see me, letting him feel the control I have over him. He loves this…the dominatrix side of me…and I love teasing him, knowing he’s craving more. Every flick of the whip, every sultry smirk, every commanding look keeps him on edge, reminding him that he’s mine for tonight.

I let him inch closer, and I lean just enough to make him wonder what I’ll do next. My voice drops lower, husky with playful threat, and I whisper promises he can’t resist. The thrill of secrecy makes everything hotter…he can’t tell anyone, and that forbidden tension makes him desperate for me.

I tease him relentlessly, walking just out of reach, letting him ache a little, knowing it makes him ache more. The way he watches me, eyes dark and hungry, makes me smirk…he’s completely under my spell, and I love it. Every playful touch, every daring move, keeps him begging for more, though he doesn’t even realize I’m the one holding all the cards.

I love when he’s begging on his knees telling me not to tell his wife about his little secret. It’s not just the allowance, the secret, or the game…it’s the heat, the thrill, the teasing power I have over him. Every week, every stolen moment, every naughty little punishment keeps him coming back, craving my presence, my control, my touch.

He knows it’s wrong. He knows he shouldn’t. And that’s exactly what makes it perfect. I’m the fantasy he can’t tell, the thrill he can’t resist, the naughty mistress who owns him all day and night, and I plan to keep him hooked until he can’t think straight without me.

Sissy Phone Chat Gets Dark With A Sadistic Teen!

Sissy Phone Chat

Sissy phone chat with a mean humiliation sissy trainer like me is always fun. I made my boyfriend dress like a sissy whore. He had thigh-high stockings on and garters, paired with pink lace panties. He also wore a schoolgirl skirt and a sexy white collared shirt. I made him put on a wig, put it in ponytails, and do his makeup. Now he looks like a proper slut. I take his pictures and tell him how I’ll send them to his friends and family. I laughed and told him to lick my pussy and drink all my pussy juices as they pour out of my slutty cunt. He licked my bald cunt like it was his favorite treat.

I had a surprise for him, though, three BBC’s ready to break in his sissy slut hole!

 

Sissy Girl Training

He screamed like a virgin being manhandled for the first time. I giggled and told them to be gentle. This bitch was a delicate flower after all. They laughed with me and pinned him down, and the first one penetrated that tight hole fast and rough. My boyfriend screamed as his virgin ass was fucked brutally and without mercy. He couldn’t move or push away, and his ass was stretched so wide you could see deep into his intestines. He screamed and cried as they all took turns on him using his fuckhole like he was a good fuck doll. They each filled him with cum, and it leaked out of his gaping hole like a creamy white river. Then I knelt and kissed him, and said this was his only purpose now because he was a useless sissy bitch.  I just loved sissy phone sex humiliation games.

Be a good sissy slut and follow me on X, formerly known as Twitter.

 

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 Panties For My Sissy Bitch

Sissy pantiesSissy panties covering your ass makes you feel like a slut. You feel so sexy as you go about your day, running your errands shopping and feeling pretty, nobody knows that underneath your clothes you have on a pair of silky satin thongs, the material against your cock and balls give you a raging hard on. 

It’s a part of you becoming one of my pets, first i make you dress in sexy lingerie under your clothes, leading up to you being fully dressed like a sexy slut for your Mistress. 

The first night of you being mine I am gonna make you all pretty, take you to a bar or lounge and make you get as many straight guys as you can to buy you drinks and fuck your tight little pussy, right in the bathroom. 

I want to pimp that bussy out to all the fellas, I can’t wait to watch them rail that tight fucking hole. You are going to take so many big black dicks for me your hole will be stretched out gaping and full of cum. 

When you get home your sister slaves will clean you all up with their tongues and get you all cleaned up, I am sure you will enjoy that, once your all clean and fresh I will be in your room to tuck you in and give you a little treat. 

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.

 

Meet other Mean Mommys on X!

Mistress Phone Sex With Peace Leads Us to The Theater

Mistress phone sexMistress Phone Sex for me changes every day. Today, we had a field trip so my little slut Lisa got to get fucked for the first time.  She was dressed up in a red skirt, fishnet stockings, a loose fitting silk black blouse, black panties and red slutty high heals. Topped off with her long blonde wig hiding from his wife who was sleeping on the couch.

We started by sucking dildos right by his sleeping wife but wanted something more adventuerous. Lisa decided her and her three dildos were going to the theater at 8am on Sunday monrning!  She messaged me when she got there and I helped that slut become a true sissy whore today.  First off I wanted a real cock in her mouth.  She showed off her skills with her 8 inch dildo and before that little slut knew it, a man made his way over to her. Sitting tightly next to her as he stroked his cock.

Lisa has a nice bulge for a sissy. She had to let her bulge throb today as we were focused on those slut holes being filled up and used as a cum dumpster.  Not every day I am able to get real cum in my sissys over the phone or chat so I wasn’t wasting a moment of time.  I instructed Lisa to start sucking the guy next to hers hard cock and boy did she.  She sucked and gagged until he started squirting ropes of cum down her throat.  Having the first hole filled up, it was time to get Lisa fucked by a real cock for the first time.

Again not long after our hunt began, she made her way over to another guy stroking his cock and asked first if she could suck his or if he would suck hers.  He very plainly said “no but I want to fuck you” at first I don’t think she was expecting an answer so quickly but I told her that there is no sissy slut of mine turning down a chance for a cock to be in you. That’s like blasphemy of the sissy world.  This man took her to a private room where he lifted up the skirt, bent her sexy sissy ass over and put his cock in her ass.  He pounded the crap ouf of her. Having no mercy on her virgin ass.  He used that ass good until he was ready to drain that load into that tight asshole of Lisas. And he let out a huge moan as his cum shot deep into that beautiful slutty sissy asshole.

All this before 9:00 a.m.!  If only every day started like that, I’d be living the dream!