Category: Online sissy training

Let me rule your SISSY PHONE SEX world.

Sissy phone sex

There’s nothing I crave more than ruling the whole sissy phone sex world, making all of the sluts love and worship me as they rightfully should. I mean look at me, I’m perfection, and you want to be just like me. Prefect round tits, and a banging body that makes all the heads turn. Imagine if you were as hot as me, how your life would be totally different. Maybe you wouldn’t be so ashamed of being a sissy. I think sissy lifestyle routines should be implemented into Mistress phone fun.

It’s not really enough to talk about it, you should be about it. Striving to live your best life as the slutty sissy girl you and I both know you crave so much to be. So why don’t you do it, take that jump and come play with me? Let’s see if we together, have what it takes to turn you into the drooling little sissy slut of your dreams.

Sissy Slave Training With A Goddess!

Sissy Slave Training Emerson

Are you craving to be treated like the true sissy you are? Ready to be my slave, I knew you were. After all, only a true sissy would want to be recruited for sissy slave training. That’s right, you heard me right, training to become the best and utter most beautiful sissy in the world, says me of course. I will train you to become the best sissy you can be.

I only have one wish and that’s for you to become either the sluttiest version of yourself, or the most beautiful pretty, princess you can be. I will dress you up and I will flaunt you all around town while you watch me take all of this cock. But I’ll only start them out, these cocks are all for you, my loves. I want them to prob and stretch those perfect pussies of yours and to make that little clitty of your squirt all over the place.

Seeing how hard your clitty gets and how swollen with all that yummy cum is so satisfying. I absolutely lose my shit when I see you and hear you explode and squirt all over the place for me. It is so delicious I can’t help but clap for you and be proud of the slut you have become. But I can also clap for the sissies that love to dress up and be pampered and paraded around town, teasing all the men making them so jealous. Let me spoil you like you deserve, my love, I promise you will love every minute!

Best Sissy Trainer for My Glory Hole Goon – Goddess Addilyn

My name is Addilyn, Mistress Addilyn to you, and I am the Best Sissy Trainer. At least that is the case for my dear old man Glory Hole Goon. In her Sissy panties and all, this one shines. 
You see he tried to act straight, and pretend that he hated the thought of being a sissy faggot. Getting to the truth was as easy as creampie with this one.

I simply forced him down on his knees before me and had him lapping up the creampie from my beautiful cunt. She followed the rules like a good little cum slut sissy faggot.
Ok, so straight men have been known to be cuckolds and doing just this. But most straight men don’t start creaming and moaning like a bitch from the first taste of another mans jizz.
My glory hole goon however, showed her true colors. Worst yet, I pushed her face from my cunt and made her undress. She was trying to avoid this. Sooner than later I found out the truth.

There she was in Sissy panties and a silky training bra.


Oh, and the best part…. little sissy faggot Glory hole goon was creaming in those panties. She confessed that she loved to go to glory holes late at night and secretly suck off cock.

She even went to far as to take strange men’s dicks in her sweet panty covered ass cunt.

Best sissy trainer

Sissies Get Used By Prisoners

Online sissy trainingI got a call from a friend saying that he’d pay me a bunch of money if I could lend him my sissy sluts for the day. I asked him what the job was and he told me he is a warden at a prison where the guys hadn’t had the touch of a woman in ages. Since I would not be caught dead in a men’s prison, he knew that my whores would love to have their holes ruined by them. I got a few of my sexiest, sluttiest and most eager whores and let them loose on the prison. Once they opened the cells in the morning, the cum whores could not escape their clutches. Cock after cock was shoved into every one of their holes. They barely had time to breathe before another cock was shoved into their throats. They loved getting abused by those prisoners, and the prisoners enjoyed fucking them so much they asked to use them again. Once my sluts can walk again (They got fucked so hard they can’t use their legs), they will be ready to take them on.

Sissy panties worn by Cum receptical

Sissy panties

My submissive wears Sissy panties and I love raping his ass when he does. Cum sluts come to see a mistress like me because they need to be reminded of their status in life. You crave to be submissive to cock but your shallow ego keeps you wearing pants until you come to see me and we make sure you play your actual roll in life. Seeing you dress up like a sissy bitch gets me so excited. You in those pretty panties and short skirt. Your mouth held back by a gag so it’s only good for one thing. Servicing my 12 in strap on before you get your twat used by BBC. But you know when your a work trying to be straight and not gay you’re actually a fucking faggot panty pretending to be a man. With me your the cum slut you hide behind the curtains and your going to worship cock in front of me. Keeping your eyes close while your mouth gets raped and I fuck your ass until I see that jizz dripping from your lips. When you’ve licked up all that cum you’ll clean your ass off that strap on.

Full-fledged Sissy training means serving all of my desires!

Sissy trainingSissy boys are my favorite, I think I get off knowing I have control over a man wearing my panties! Bending you over and watching your lashes bat from the pressure of my 13 inch strap on makes Mistress so horny and wet… Especially when you beg me for the man that sits there watching me humiliate you while he’s stroking his big dick that you are drooling over. You know that big dick wants you gaping and easy to slip into. Your ass is under my control now! I have you post ads and set up dates where you and I have a mutual agreement.. I get 80 percent and your take home is 20 percent paired with a creamy load drooling out of your cock craving hole..

Your cum filled Sissy panties, I have you wear around town under your sexy outfit.. Doesn’t it make you feel so naughty knowing your undies are full of cream.. When we get back home I have you slip out of your panties and suck the crotch while you bare another round. If you are on your best behavior I may just rub your clit while you get mounted causing you to squirt and piss at the same time.. Those are the best orgasms aren’t they? A hard pegging and huge cumload from a glistening big black cock for you to clean when he is through is the perfect treat for you!

You love being a faggot for me and I love offering you Sissy slave training.. Fucking a sissy boy anally while you surrender is everything a mistress dreams of… I get down on my knees and teach you how to properly swallow up every inch of a big thick hard dick.. Teaching you how to be the best sissy slut you can be! If you don’t do well after training I will put you in chastity to enslave, humiliate, tease and deny you any sort of pleasure for weeks.. I will selfishly take his cock and make you watch as I drain his balls inside of my sweet pink hole..This can all be avoided as long as you know how to follow instructions! You and I both know Sissy training is to be taken seriously. Do not waste any of mistresses time or you will be paying in consequences. 

Sissy Training On and Off the Phone Gives Me Sissy Mom Pride

sissy trainingI love sissy training. In fact, I have a sissy’s dream closest. It is full of vintage and modern lingerie, pretty dresses, all kinds of underwear, stockings and high heels. My daughter and I are a sissy trainer duo. We share custody of a few sissies. One more recently, is a friend of hers from high school. He was born in the wrong body. I knew it before he did. She is living her best life as a sissy now thanks to my daughter and I. He works from home doing computer graphics, so no one cares if he looks like a pretty girl while he works. I know most of my sissies cannot be out about who they are. Sissy phone sex is the best they can aspire to. But when I get my hands on a sissy without a care in the world, I go all out. My daughter and I took our sissy to this road stop sex shop. They are all over the highways on the east coast. It was a Lion’s Den. Maybe you have heard of them, or even been inside one. Many of them have glory holes. They attract a lot of truckers who honestly do not give a fuck who is sucking their cock. My girl and I dressed up our shared sissy. She is only 19, like my daughter, so I knew she would be popular. Tight holes, soft skin and pretty lips. I dressed her up in a pretty pink dress. Not frilly, but slinkier. I was going for the lot lizard / hooker vibe. My daughter did her hair and makeup. I oversaw the wardrobe. We took our pretty girl to get some cock at the Lion’s Den where she was the belle of the ball. She sucked over 20 cocks. My girl and I had some femboy training pride because our girl swallowed every drop too. She even took cock in her back door sissy hole and made her clitty squirt. I was a proud sissy mom. Think you can make me that proud?

 

Mistress Arabella’s Hypno Session

Sissy hypno training

Arabella’s Session

Are you ready to take my Sissy hypno training? Good grab your lube get naked and get comfortable. 

Ready? Perfect, I want you to close your eyes and listen to the sound of my voice. “I know you have been trying so hard to fight your urges. Be a good straight man, but I want you to picture a big fat black cock. I mean a massive one. 11 inches long with the girth of a fist.”

“Look at you! You are practically drooling aren’t you. You want to taste it, I know you do. Envision that cock now pointed at the mouth of yours. Pushing against your wet lips. It is begging to come inside. Go on, open your mouth, let it in.”

When I snap my fingers you will open your eyes and know your true calling. You are a sissy cum dump. Your sole purpose is to serve big fat cocks. 

Femboy training sometimes requires a gentle touch.

Femboy trainingIt was raining out where this femboy training master lives, and while my pussy was in need of a good pumping and cumming, I felt the need to head around the back of my house and walk a little instead. I’d find a man soon after I got back, was what I thought. In fact, I called one while I walked, told him to show up at my house for a hot ride. Then I ran into a cute girl on the path, she was in torn clothing, drenched from the water, and her soft skin really stood out to me. I was gonna pass her by, she really wasn’t my problem even if I did feel sympathetic, that was until I noticed the cock. “Are you a guy?” I couldn’t help but ask, and at the shake of her head, I knew I’d found a sissy who would worship me very easily. “Come on.” I turned back. “Let’s get you cleaned up and clothed.”

One of the best decisions I’ve ever made. That’s a loyal sissy, doesn’t ever question me, I’ve had her lick my toes in front of visitors dozens of times just to prove she’s obedient to a fault. And when I’m feeling froggy, I have someone ready to lick me to a messy orgasm on the spot!

Sissy Training With Goddess Emerson Will Leave You All Dolled Up!

Sissy Training Emerson

Online sissy training is my absolute favorite! Sissy training in general is amazing, but the fact that I can turn one man into his true self from hundreds of miles away makes my pussy sopping wet! Just thinking about all of the “men” out there who crave the touch of a Goddess like me makes me excited. You know who you are, and you know exactly what you crave.

Its only natural that you come crawling to me and call me up asking and begging for me to make you into your perfect slutty or princess self. I can either turn you into a big and beautiful princess of a woman, or I can break you down and make you into the whore you were born to be. Leaving all of your whore holes fucked and filled with that oh so creamy delicious cum you crave. This is all simply with my voice over that phone, of course.

So, what’s it going to be? Are you a pretty, pretty, pink princess? Do you long for me to dress you in the finest of finery and drag you to only the best places in the world? Or do you crave the rush of not knowing who is fucking you and filling all of your whore holes? Either way, I am the woman for the job, and I love making you into your true self. It gives me a rush and makes my pussy drip in excitement whenever I am able to turn my latest masterpiece into its truest form.