Category: Sissy humiliation training

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!

Sissy Panties for Loli w/Heaven

 

When Heaven and I put you in sissy panties you fucking know it. Lolipop came to be used one morning asking if we could help her get all dressed up and fuck her butt with our handy dandy sissy strap-ons. We already know how Lolli likes his deep-complected Mistresses. And Heaven is that Bittersweet Candy that Sissy men like Lolipop can’t get enough of. The way she just pounced on a Femboy had me so fucking hot. This Sexy Black lady definitely knows how to put white men in panties, frillies, and slutty BDSM outfits. I shouldn’t have been surprised, I almost volunteered myself to ride that big black dick she had swinging and ready for Lolli! 

sissy panties

Not That Lollipop the sissy needs Forced feminization, but as hard as Heaven was putting her through the hoops, I knew that she meant business. It’s so majestic to watch another mistress find a new slut and take control of her sissy boi ass like no other. Both of us took turns dressing our slut up and fucking her butt pussy. I just love pulling those panties to the side under her spanking skirt and finding out that she is now off of her period and she can not only take our big dongs, but she is ready to meet Heaven BF and mY black bull for some good ass sex. We even picked out a new toy for Our slut and she is going to Write Heavens Name on it and send pics with her ass full of her new dildo! Always a pleasure to introduce company sissy sluts to a new mistress!Forced Feminization

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?

 

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.

Sissy humiliation training fun with Miss Remi

sissy humiliation training

Are you a secret sissy in need of some dick? I could train you to be the perfect cum dump slut! My favorite thing to do is to teach men how to be girly, sissy bitches! I just had a kinky cum slut call me for some sissy humiliation training over the phone. He sent me some pictures of his pathetic, little dick which showed me why he’s a sissy bitch in the first place. I laughed my ass off and told him to go hide that tiny thing behind some pretty panties. There’s nothing a sexy slut like me hates more than having to look at a mini dickie like that! I made him put on a tight, little dress and go out to find a fat cock to take. I had him stay on the phone while he walked around the bar, dressed up like a whore. He was telling everyone what a little panty slut, bitch he is and how badly he wanted to take a fat dick for the first time. I made him walk around, flashing his panties at different people and humiliating himself until he found a hot, older Daddy with a giant bbc. From there, I made him stay on the phone with me while he gave up his virgin, sissy pussy to that massive fuck rod. I could hear him slurping and gagging and I got so turned on! I could hear the sound of his panties being ripped and torn off of him and then I could hear him moaning while his slut hole was being stretched for the first time ever! I’m getting so wet thinking about how he was screaming and moaning for that fat dick to cum for him! Call me so we can talk about my sissy sluts or you can become my next cum lover whore!

 

Cock Sucking Sissy Phone Chat!

Sissy Phone Chat

The best way to learn to suck dick like a pro is to have hot cock sucking sissy phone chat with sissy training mistress Raine! I’ve sucked more than a few dicks in my life because I’m a down and dirty phone dominatrix with a craving for deep throat fucking. I’d even say I’m the head bitch in charge of gobbling cock so any of my sissies must be trained to my standard! That’s why whenever I have nasty sissy phone chat, I make sure to tell them to grab their biggest dildo so we can practice slurping down big hard dick together. My sissies love it when I have my stud cock join us on a phone fuck so they can hear me gulping and gagging like a filthy mistress phone sex goddess. I have to make my sissies the best at swallowing cock because their sloppy top skills absolutely reflect on me and I have to maintain my reputation as the best bbc sissy trainer that money can buy!

Online sissy training never gets better than traps and punishment!

Online sissy trainingOnline sissy training with men like these is fun, but what’s more fun is when I’m done and they get their graduation present. I don’t always do it the same, sometimes I’ll keep them on as maids, or sluts, or cock gobbling heroes. This time I’d trained them especially in how to eat begging cunt and make a mistress like me writhe and lose a little bit of herself in the moment. Only the best sissy get trained like that, because it makes a host vulnerable to orgasm too hard, so they need to be obedient enough to know not to take advantage when I’m on the floor, sweating and panting, legs spread and my – oh who am I kidding, I want that so badly! I graduated these ones a little too early, set them up for a great trial, practically knocking me – their phone dominatrix – out with their swift and powerful tongues, and then when I was vulnerable I puffed up my pouty lips and spread my cunt lips a little with my fingers to tease them. “A good pet wouldn’t even be tempted.” I said, knowing I’d very quickly have a cock in me and I was pleased to know these predictable sissies can’t resist. I’d be punishing him endlessly for this, he’d be in remedial classes and getting the hard whippings for a good long time for the pounding he was giving me, but that’s half the point isn’t it? True power is picking a guy who wants you to destroy him, and doing just that. Making things seem fair when you’d planned their downfall right from the start. Is it entrapment if you’re just a sissy training master picking someone to torment and get a nice helping of cum in your cunt at the same time? Legally, not sure, but it sure feels like it. The knowledge I set him up to fail and now get to punish him made me cum long before his cock did, but I definitely lost myself on his dick so it was worth it in two ways!

Forced feminization for what, when you can roofy his drink!

Forced feminizationI turned a “man” into a F A G G O T. He came over for a good time to find me and a group of black guys celebrating his arrival.. Forced feminization was in the works! I’ve known him for a while and his dick does not measure up to my liking.

I decided to introduce him to his inner-self he never knew. As quick as he cums when we fuck, I knew there had to of been no way he was actually enjoying himself.. His hypersexuality had him coming back for more but realistically speaking he didn’t last long enough to actually feel the true sensations that sex has to offer. I poured him a glass of wine that I had roofied with molly.. I knew for certain the only way he was going to give in was if he were intoxicated..

As soon as he started swaying I stripped him of his denims and muscle shirt and tucked his clit into a sexy red pair of Sissy panties.. Well, TBH they were my used panties from the hamper; I wanted his clit to have the fresh scent of my pussy so when the guys went down on him they would get a whiff of heaven tucked between his legs. His man pussy was prepared naturally with a rim-job and a slip of masculine fingers rotating in his ass.. His woody stood tall while he got his prostate massaged.

I knew he would enjoy the feeling of his skin clench and heat up when the head of a big fat cock slid into his asshole. Goosebumps filled his body while he was bent over the barstool taking a big thick dick deep into his derriere. A prostate milking was what he deserved! I gently caressed his nub while he howled and pleaded “harder, harder OMG ————-> daddy!” My jaw dropped; he naturally surrendered. He didn’t even require too much force! For the entire night he pleaded for round after round and ever since he’s become an addict with a need for Big black cock! What makes me the Best sissy trainer? Simply by helping you establish your sissy persona and desire to reach your true potential of satisfaction! This process happens naturally in due time.