Category: Best sissy trainer

How Will You Serve Mistress Raine?

Mistress Phone Sex

My sissies love making their Mistress Raine cum hard hearing about all the cocks they have taken! It’s no secret that my sissies are the best cum sluts out there, they fuck with the intention of telling me all about it. They love hearing the happiness in my voice when I tell them they drained those balls exactly as I would have. My sissies are completely devoted to being obscene cum dumpsters on a mission to take as many cocks as they can before their holes are all fucked out. My sissies love sending me pictures and even videos of them sucking a taking cock in their tight little boy pussies. If you think you have what it takes to serve me and be one of my very fuckable sissy sluts, Call me!

Sissy phone sessions

sissy phone

Get ready for some wild sissy phone fun. I’m going to use terms that will be hypnotic. You will be my sissy slut who will do whatever I say. Once you do what you want, you will move on to the next level. Sissy tasks tend to be all about what makes your mistress happy. What makes me happy is a fluffer and a vacuum cleaner. Go ahead and suck a cock till it’s hard, and clean up the effect. Take notes and learn what will make you the best sissy slut.

It is an honor for you to learn the best tricks and tips for becoming the best cock sucker and the number deepthroater. you are so lucky to enjoy training from the best red headed goddess around.

Femboy Trainer Jackie

femboy training

If you’re in dire need of femboy training, then I am just the Mistress for you. I love nothing more than helping boys just like you transform into the most gorgeous femboy slut you’ve ever seen in your life. Sure, you can be a sissy and just kind of do it haphazardly, but that’s not what you really want, is it? You want to be the very best version of yourself and if you stick with me, that’s exactly what you’ll be. Everyone will be in awe of your beauty and transformation, and that’s when you’re going to start getting cock.

So, until your training to be a femboy is complete, you don’t need to worry about dick. You will get it in due time, but that time is not right now. We’ll be talking about how to turn you into the prettiest sissy in your town. Hair appointments, waxing appointments (this one is super important), manicures and pedicures, lingerie, and shoe shopping – all of that and then some is in your future. Are you ready to be fully feminized by a woman who knows exactly what she’s doing? Then book a session now for your Cinderella moment!

Teaching Him His Place

forced sissy trainingHe was a regular of mine who loved to fuck my tight wet cunt with his hard cock. I got bored and decided today that he needed to know his place. I was on top of him riding his thick cock so fucking good when my boyfriend came in. He came in with his long hard black cock I grabbed my little cum whore and told him that he is going to learn his place today. I told him to suck my boyfriend’s cock like a good little bitch. He was doing so good, and I decided I could make a lot of fucking money off of my little slut, I called my men over to come and fuck my cum rag while I count their money. They all came in and he got straight to work, he went over and started sucking all of their cocks one by one. I went up while he was sucking one of their cocks and shoved my fingers up his tight little asshole. I stretched his asshole out with my fingers getting him ready for the huge black cock that was about to be shoved in. He was such a good little cum whore and he took all of their cum cleaning off all of their huge fucking cocks.

Forced Sissy Training

Best sissy trainerSissy TJ hasn’t been following the rules as he should. He seems to think I should grant him plenty of hall passes. He has no idea what’s in store for him! Master Brielle doesn’t like being disobeyed and once I get my claws on him I am going to show him who his fucking Superior is!! Does he really think I am that kind, that I just have all the heart in the world to continue granting him passes for his disobedient behavior… Well that poor thing thought wrong! I am going to ram his fucking asshole so fucking hard during our next session! I will be force feeding him a big fat long double sided 24in cock!! Think he can break a record? Well we are going to find out! I am going to show that fucking slut no mercy! A real woman keeps her word and she obeys her superior; she serves her fucking King/Queen on a golden platter. It seems Sissy TJ has a lot to learn and if she continues to go down the path she is on she will meet the darkest side of her Master. I want to hear her choke, gag and drool.. Gasping for air as I ram her throat so hard. She will soon learn to sit with poise to obey her Master or she will be suffering severe consequences! Forever your Master whether you like it or not. You get what you signed up for. Now get down on your knees so I can show you what a real pussy looks like.

Sissy Panties Full of Cummies!

Sissy Panties

Your sissy panties are going to be soaked when I’m done with you! You are such a good sissy that Mistress is going to let you feel her superior pussy pressed up against your clitty! Only though the panties though as I don’t want you to get too spoiled. Giggles. As I grind back and forth making your itty bitty dickie will feel wet and sticky from my cunt juice you need to be worshiping me as the Goddess I am. I’ll even let you suck my toes while we scissor. pretty little slit so wet and sexy but no more for you! Get down and assume the position so I can spank your tush! The only sound I want to hear is the sound of you moaning and begging for BBC while I smack your rump! Right when When I think your man purse is ready for me to drop change in it, I’m going to go balls deep in you! Mistress is going to milk that prostate until your man pussy squirts! 

Breaking In New Pretty Little Sissy Bitch

I have a new pretty little sissy bitch since my perfect sissy has strayed and I wanted to show my new one how to be.

Sissy slave training

I bought the biggest two-sided dildo I could find. I bought some new sissy panties and bralette set with matching stockings. When my sissy walked in, she got naked right away I love watching her little clitty in between her legs excited to see me. I turned her around and spanked her ass and made her tell me who she belongs to. She got dressed in 6-inch heels and crawled to me. I spread my legs so my sissy slut could lick my cunt and get it wet for the strap on dildo I had for us. She did as she was asked and when I put it on, she was bent over spread open showing me that man pussy. As I pushed my strap-on deep in my new pretty little sissy the other side went deeper in my cunt. I started fucking her hard and deep making sure I used her so I can cum hard. I didn’t stop until I felt my body tense up, I started cumming hard. I pulled out of her now gappy man pussy and told her to stay that way until I was ready for more.  

Best Sissy Trainer

Best sissy trainerLet’s go shopping! I’ve turned Sissy cooper into the perfect slut. No matter what he will never be a woman so he will always come back crawling to me. He knows fairly well who his superior is! He aspires to be a woman much like myself, one with sass and a nice round ass. The kind of lady that turns every man’s head! Cock drawn to her without a mention. He’s learning how to suck cock like the perfect princess fuck slut that he is. We have been practicing his nice feminine moan. No man wants you grunting while giving him a blowjob. You are going to have to learn to squeal and let out musical moans to raise the hair on his body. What better way to learn than by the best sissy trainer out there. You can check my resume! Come find out for yourself. I don’t want an average Jane. I want an extravagant bitch who knows that a woman requires daily grooming. A dramatic style with one that stands out in every room. There is no competition!! We see no competition!! When I am through with her. She will have all the other sissies wishing they could be her. Manicures, pedicures and waxes from head to toe. Lace fronts and Jewels. Nobody said becoming a woman would be easy but for certain it isn’t impossible. Sissy Cooper will be one of a kind when we are through with sissy training!

Sissy Girl Training

sissy girl trainingLooking for sissy girl training? I love to train sissies. I am a mommy and a nurturing sissy trainer. I treat my sissies like my daughters. I dress them up frilly and pretty. And I teach them all the things they need to know to please men. I have a new real-time sissy. She found me through my daughter. He used to go to school with my daughter, but he dropped out before graduating because he was bullied. He was a femme boy then. Still is, but now he wants to transform. He plans on becoming a T-girl. She is saving up for a boob job, but in the meantime wants to work the truck stops and glory holes for money. My daughter brought her former schoolmate to me because she knew I was the best sissy trainer for the job. She was right too. I know how to turn a boy into a cock sucking princess. A few days with me as her trainer, Mark became Michelle. I did her makeup. I put her in a wig and some very pink and frilly clothes. I showed her how to walk like a woman. I showed her how to suck cock like one too. Such a pretty girl afterwards. She is a natural cock sucker. Honestly, one of the best I have trained to date. She took my big black dildo balls deep after the third try. It is 12 inches long. I knew where to get her maximum money for her skill set. The truck stop is full of black truckers in need of an eager mouth to drain their balls. When she became Michelle, she wanted big black cocks. So many sissies do. I am a BBC sissy trainer because I am a BBC slut. The bigger the better if you ask me. Same for Michelle. I took her to the truck stop last night and she made a couple thousand dollars just sucking on big black dicks. She will have her money for her boobs in no time with me as her trainer.

Sissy panties required!

sissy panties

I want to tell you about the first time I caught a sissy bitch wearing his sissy panties in public. I was a cheerleader when I was younger and he was a football player. His shirt rode up on the bus one day and I saw a peek of his frilly, pink thong! No one else noticed but I did so I snapped a quick picture. After the next game, I confronted him and told him that unless he wanted the whole team to find out, he better agree to be my little, sissy cum whore! I brought him back to my house and played dress up with him. I put him in a tight, slutty outfit and called my daddy and uncles into the room! It was so hot watching him get his virgin pussy hole used for the first time! I have so many stories about catching men wearing panties in public but that one always makes my little, slut trainer pussy wet!