Category: Online sissy training

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.

Miss Remi the training slut

mistress phone sex

I’m ready to play with a panty boy and turn him out as a bbc cum guzzler.

I have a sissy slut that’s about to get his virgin pussy wrecked and ruined by fat, bbc. He doesn’t know it yet but I’m sending a group of young bullstuds to his house so that they can turn him out. I just wish that I could be there to bend him over, pull his panties down and hold his ass open for those giant cocks.

Let’s talk about what happened last time my studs and I turned out a panty boy sissy fag. I showed up at his place in the middle of the night and forced my way in. He was already dressed in some silky, satin panties and a matching nightie. His ass cheeks peeked out from his panties and looked cute when I made him bend over for my studs. I slid them down just past his round ass and held his cheeks open.

The stud with the biggest cock was the first to step forward and ask Miss Remi for that sissy’s cum hole. I held that massive meat sword in my hand and stroked it while lining the head up with my slut’s cunnie. My sissy bitch panty slut backed her ass up onto that huge cum cannon and let the head pop into her tight fuck hole. She clenched up, tightening her he-pussy around that big dick. My stud held her hips and worked his huge dick in and out as fast as he could.

Another of my studs got in front of that sissy slut and fucked her throat. The muffled, wet choking sounds filled the room as they pumped faster and faster. Those two massive cocks were slamming the slut back and forth in a hot, spit roast scene straight from a porno. The cum rag, panty slut ended up getting double stuffed with hot, sticky cum while I played with my cunt and recorded the whole thing. You probably crave cum in your throat and sissy fuck hole too don’t you?

Let Miss Remi turn you into the cum gutter slut that you’ve always dreamed of being!

Sissy Girl Training with Tough Bitch Tanya!

Sissy Girl Training

Which one of you needs Sissy Girl Training?

I know a pathetic, small cock man the second I hear your voice.

Your miserable life would be much more fun if I turned you into my little sissy girl.

A tiny, useless cock like yours would be better suited in my little lace panties.

And forcing you to wear a matching bra.

You are an ugly man, but you’d make a decent-looking whore, I think.

No one can ever tell your sad excuse of a clitty is in there!

You can’t hide now, when I take your sorry ass to the streets.

A shy, little ass, virgin like you is fresh meat for these paying men!

And I know they’d pay good money to be the first cock inside you!

Pop that cute little cherry hiding in your panties until you are screaming in pain!

Has your little hole been stretched this much?

Because tonight it’s only going to be gaped open!

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Sissy Hypno Training is The Best Way to Surrender to Urges

Firstly, I am Addilyn, the ultimate Mistress. And I offer up Sissy hypno training. Now, I specialize in the exquisite art of breaking men from their mundane forms. Accordingly, to make you a pretty doll.
Therefore,  this Hypno training is designed to strip away your masculinity. And to replace it with a craving for submission.
Consequently, the process begins by dismantling your ego. And forcing you to surrender every ounce of control to my guiding voice.
Furthermore, I believe that true liberation comes from embracing the forbidden urges. Ultimately, the desires you’ve suppressed for years.
As you sink deeper into my hypnotic trance, you will find that resisting is futile. And giving in is the only way to find peace.
Accordingly, the first step in your new life is simple: strip off those drab men’s clothes. Now slide into a pair of frilly, lace sissy panties.

Sissy Hypno Training is the Ultimate Adventure

Once that silk touches your skin, the transition becomes inevitable.
Ultimately, you will learn to love the feeling of being my plaything. And trading your pride for the blissful emptiness of a sissy.
One who exists only to serve my whims and satisfy my desires. So, let’s start.
First, I press play on the screen behind me. Immediately a soft pink light fills the room as the video begins. Simultaneously, spirals start to spin slowly.
Then, my recorded voice layers over a low, pulsing beat. “Now listen carefully, sissy. Nevertheless, your eyes grow heavy. And your thoughts grow soft. Now, you want to obey. You need to obey.”
Then, I stroke your hair with one painted nail while the video works. “That’s it. Sink for Mistress Addilyn. Now, every word I speak digs deeper. And every image rewires you. Naturally, your cock is no longer yours. Therefore, it belongs to me now… locked, ignored, and shrinking while your mind softens into pink silk.”
Next, the video shifts. Soft images of lace, lipstick, and kneeling sissies fill the screen. So, my voice continues, warm and relentless. “You crave the training. And you crave the hypnosis. Each time you watch, you become more feminine, more helpless, more eager to please.
So, you will beg to wear panties. And you will beg to suck. You will thank me for every command.”
Now, I lean down, lips brushing your ear. “When I snap my fingers, you will open your eyes as my perfect little sissy. And you will feel the need to obey burning in your empty mind. You will say, ‘Thank you, Mistress Addilyn, for hypnotizing me.’”Snap.
Sissy Hypno Training

Miss Remi’s new sissy slave

sissy phone sex

I met my newest sissy bitch on a kink app. His profile said that he was “straight but curious” and I knew what that meant. He needed a hot, little mistress like me to train him. I sent him a short but sweet message telling him to meet up with me on Friday to start his week of training.

On the first day he showed up still dressed in his manly clothes. He had on a pair of cargo shorts and an old, ratty tee shirt. I opened the door dressed in nothing but thigh highs and a sexy corset. After inviting him in, I ordered him to strip down naked in front of me.

His dicklette jumped in his pants and I laughed at him and then locked the door.

I forced him to shave his entire body for me. Legs, arms, chest and even his balls. Then I dressed him in the softest, lace panties that I could find. They were pretty, pink and had a little bow on the front of them. His less than average cock twitched in the front of them and I laughed and flicked it a few times. The matching bra and a tiny, tight mini skirt completed his sissy fag look. We spent the first few days making him practice walking in high heels and applying makeup like a real girl.

Once he had perfected the art of painting his face and prancing around in heels, it was time to start training.

The entire third day consisted of this sissy whore learning to suck my strap on. I held his face and pumped that thick fuck toy down his throat. He whimpered and gagged but I kept reminding him that this is what real sissy faggots live for. I watched his tiny clittie dick jump around in his panties and could tell how badly he wanted to stroke it.

After fucking his face for hours, I locked his clittie in a cage and sent him to bed stiff and desperate to cum.

The next day was even more intense. I invited a bullstud over and had my sissy bitch show all the cock sucking skills that I had taught her. That big dick sliding between her painted lips looked so hot! I giggled when the little panty boy got his mouth blasted full of cum. He cried a little when he first swallowed the milky cum shot but then he started begging for more.

By the end of the week I had that slut fully trained and turned into a sissy fag, panty bitch. He was walking with a little sway to his hips in a way that told everyone exactly what he was. Call Miss Remi so that we can talk more about my exciting week of turning this average guy into a cock worshiping sissy slut!

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

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.

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.