Category: Best sissy trainer

Sissy Phone Chat is Where You Best Surrender to Mistress

Sissy Phone Chat is where desperate Sissy faggots come to surrender to a Goddess. So, I am Mistress Addilyn, and this is my lair.  And this is where you arrive already broken and ready to surrender.
Consequently, you stand before me wearing nothing but those thin nylon panties that cling to your pathetic leaking clitty. Since you crave my expertise and commanding ways, I will begin your conditioning immediately.
First, I introduce you to your new best friend, a big black dildo. And this is a tool to train you well. So, part your pretty lips and start sucking. That’s right, sissy, start to show Mistress your skills.
Therefore, the sheer girth of the BBC dildo makes you struggle to take it in your dick-sucking lips. When I feel satisfied with you taking the dildo in your lips, I move on to the next step.
Now, I position the big black dildo in my strap-on harness. And I command you to kneel. That’s it kneel before Mistress like a good sissy slave. Now we will practice you making eye contact as you start to worship my BBC.
Meanwhile, the friction of the sissy panties against your sensitive skin intensifies the pleasure of your clitty. As a result, your body reacts instinctively, and you begin to leak precum that soaks into the fabric.
Now, it’s time that I train that man pussy. So, I direct you to my training bench. Here I will cuff you and spread your legs as you are bent over. That’s it, thrust that sissy ass out for Mistress’s big black dildo.

Sissy Phone Chat With Mistress Addilyn Will Break You

At last you are about to get opened up and take my dick. And I begin to slide inside that sissy cunt. Therefore, you begin to whimper a little like a little bitch.
Subsequently, I increase the pace of the thrusts, forcing the BBC deeper into your tight hole. That’s a good sissy; just push against it and leak more in those panties. After all, I keep them on you and just shove them aside.
Furthermore, I grip your hips firmly, pulling you back onto the shaft with each stroke. Ultimately, the best sissy trainer is really introducing you to the BBC. Soon, you will enjoy the real thing.
Additionally, the constant rubbing of the nylon against your clitty sends waves of pleasure through your entire body.
Moreover, I vary the angle of penetration, hitting new sensitive spots inside you with every thrust. In addition, I reach around and press my fingers against the wet spot forming on your panties.
Consequently, the pressure on your leaking clitty drives you closer to the edge. Nevertheless, I do not allow you to cum yet. Instead, I slow the pace and edge you repeatedly.
Thereafter, I resume the relentless pounding, stretching you completely through the thin fabric.
Ultimately, the constant stimulation and denial leave you trembling. And you are leaking uncontrollably through your panties as you surrender fully to my training.
Finally, I have molded you into the perfect leaking sissy, desperate for more.
Sissy Phone Chat

Forced Sissy Training Ends With A Bang

 

forced sissy training

The finale was a blur of leather, sweat, and cum. I had him draped over a bench, his ass high in the air, trembling. I didn’t use a toy; I used myself. I climbed on top of him, my leather skirt riding up to reveal my soaking wet pussy. I guided his cock—now leaking pre-cum and desperate—right to the edge of my heat. But I didn’t let him in. Not yet.

 

I spent ten minutes teasing him, grinding my clit against his shaft while I used my heels to pinch and pull at his nipples. I wanted him on the absolute brink of explosion. “Please, Rosemary… please let me cum,” he begged, his voice high and broken. I laughed, a cruel, melodic sound, and finally slammed down onto him, taking every inch of him in one wet, sliding motion.

 

I rode him with a violent intensity, my leather corset creaking with every thrust. I wasn’t looking for intimacy; I was claiming ownership. I watched his face as I pushed him past the point of no return. As he finally erupted, spraying hot cum deep inside me, I leaned forward and whispered in his ear, “You’re mine now. My sissy, my toy, my slave.” I climbed off him, leaving him shaking and spent on the floor. I stepped over him, the clack of my heels signaling the end of the session. He didn’t even try to move; he just lay there, completely broken and utterly mine

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.

Adult Phone Chat Lines the sneaky way to explore your kink!

Adult Phone Chat Lines are the sneaky way to get your fantasies out!

Does your wife not know about your dirty little sissy secret?

Adult Phone Chat Lines

Does she know that you steal her dirty undies and bras to parade around the house in?

Like you are a good little whore all dressed up for the part.

Does she know her husband is a sissy fag begging and searching for a cock to suck?

But don’t worry I’ll keep your dirty secret between just us.

She doesn’t have to know that your mouth is watering at the thought of a big black cock face fucking you.

Or even bending you over, spreading your ass cheeks wide open and fucking that tight little virgin bussy hole. 

Would be a shame if she found out about all your faggy little desires. 

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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!

Forced Sissy training for the weak…..fuck slaves

Forced sissy training

Forced sissy training starts now, I start by shove your face into the bed, yanking your sissy panties down over your girly ass. A string of pre-cum dripping from the tip of your caged pathetic dick, soaking the frilly fabric. “Look at this,” I sneer, grabbing a fistful of your hair to twist your head around. “Your clitty is so desperate it’s crying, and all I did was look at it.”

I roll you onto your back. Your legs open. The metal cage is taut around your useless cock. I grabbed the giant bottle of lube. “You know the rules, cock whore. Sissies slaves don’t get hard. Sissy slaves get fucked.”

Sissy Fucking

I slick up the biggest strap-on cock I have, a huge, thick, veiny dildo. I slap it against your cheek. “Open up!.” You obey; mouth stretches around the head. I fuck your face with it, slow at first, then pounding your throat. Gagging. Tears. Mascara rivers. “That’s it. Choke on it.  the taste. This is all, your throat is good for now.”

I pull out, spit and lube coating your lips. I spread your legs wide and press the huge head against your tight hole. You flinched. “Don’t you dare flinch on me.” I slap your ass cheek so hard it echoes. “Relax that hole for your Mistress. You’re a fuck whore now. Whores take it in the ass.”

I push inside. You screamed, muffled by the pillow. I don’t stop. I sink my hips against your ass, burying the whole length. “This is your cunt. This fuck hole is your pussy now. This is where I fuck you. I own you.”

I start pummeling into you. My thighs slap your ass. “Who owns this hole?”

“You do, Mistress!”

“And what are you?”

“Your sissy fuck slave!”

I reach around, grabbing your throat from behind, pressing down as I fuck you harder. “Louder. Tell the whole fucking house what you are.”

“I’m your fuck slave! Your fuck hole! Your personal cum-dumpster!”

Breeding your pussy

My clit grinds against the strap-On’s base, my own pleasure climbing with your humiliation. “I am breeding this pussy. I am training it to take cock like the perfect little cunt it was always meant to be. Now cum. Cum from having your pussy wrecked, you pathetic bitch.”

Your body convulses. A dry, shuddering orgasm wracks your caged cock. You drooled on the sheets.

I pulled out. A gush of lube drips out of your gaping hole. I shove the dripping strap-on in your face. “Clean it. Lick it clean. Every drop. Then I’m going to break that mouth again. You aren’t a man anymore. You’re a meat-puppet. My meat puppet. Got it?”

“Yes, Mistress.”

I lean down and bite your neck. “Good sissy slave.”

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

Dressed Up In Dirty Sissy Panties

Sissy pantiesMy good boy Joey loves to play with me in his Sissy panties, everytime we chat he gets all dressed up in his mommy and sisters dirty panties for me, I have him dump out their hamper, finding the dirtiest panties, filled with cum stains, some shit stains too, I always get him to smell and taste them before he slides them on his tight ass, his big long cock cant fit in the thongs, its too long and fat, we normally tuck his meaty memeber into a sweaty gym sock.

Joey stuffs his bra with dirty panties and cum stained stockings. I make him crawl to his mommy’s room like a good boy to put on his makeup and find something sexy to wear; today he dressed in a mini skirt and cum stained thigh high stockings.

Once all dressed and pretty, I sent him to find his mom and sister’s cum covered dildos, the biggest one for his tight asshole. My good boy puts on a good show every time to please me. I tell him how to ram his ass with his sister’s dildo covered in her juices; he really gets turned on when I tell him how his mom and sister are watching him on camera as he is dressed up in their stinky underwear. He shoots a huge cum shot in his sister’s sweaty thong like a good boy.

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!