Category: Forced sissy training

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!

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.

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 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!

 

Do What I Say

Sissy girl training They love that I make them beg for more. They love that I make them get on their knees and beg for a taste of my wet cunt. I love to dress them up in bright pink panties like the fucking sissies they are. I love to humiliate them by telling them no woman will ever be satisfied by their tiny cock. The only thing that a sissy is for is taking a big fucking cock and shoving it right into their tight little shithole. These sissies know their place and they are all lined up waiting for the next big cock to assault their tight fucking ass. They know I love to hear them beg for that huge cock and if they don’t do it good enough, they get punished. They loved to be punished by me. They beg for my little fuck machine to come out while I whip them until they beg for me to let them cum. They know they have to make their mistress cum before they do so they beg to lick my pussy with their little faggot tongues. Then right after I cum I order them to cum all over my stomach and then clean up their fucking mess.

Maid Training Mistress

sissy maid training

You probably already know this, but one of the things I love most is when I get to do sissy maid training with a new caller. Now, don’t get me wrong. I love all of my longtime sissy maids. But everyone loves the feeling of something new and I’m no different. Helping a new sissy maid pick out a cute uniform, sexy heels, hair, makeup… that’s just one of the most fun things to do. I love the excitement that brand new sissies have. And so many just love taking care people, so being a maid works very well for them.

Do you want to go with the classic French maid uniform? Or would you like to try some different looks to see what looks best for you? You definitely need the cute little feather duster so you can just prance around in your heels like a dainty little lady. But we all know that you’re going to be used like a nasty slut. You might try to play it off like you don’t like it, but we all know that you do. I hope you’re ready for the very best sissy maid training around!

 

dick breath

 

Are you craving chocolate honey, aren’t you? Something big and juicy won’t fit, but you will beg to make it work, huh? Don’t lie. You know you want the mark to fuck your ass pussy. Don’t get your panties all wet, and you sissy cum fuck. There are some rules to fluffing because that’s what you will be ultimate. Mark wants no part of your sissy cock. Instead, he wants you to prep him up by sucking his cock and being the vacuum.

What do you think a vacuum is…. I’ll wait. Hmmm, still doesn’t come to your sissy mind? Maybe it’s cause you keep staring at Mark’s big cock! Now you stop it right now. You better listen to me give you some humiliation phone sex to pass the test. A fluffer is a pregame and endgame. You should be happy you start something and clean it up like a vacuum. Enjoy your dick breath bitch!

Humiliation phone sex

My Boyfriends into sissy training

 

Best sissy trainerSo, My soon to be ex boyfriend has been having me give him anal. I haven’t got off much lately by his cock but something about seeing him look back at me while I fuck him deep in his asshole has really been making me weak lately. Recently I created an ad on craigslist since he loves anal so much. I dressed him up in a cute lavender teddy and invited about 6 dates over from online. You should have seen his face when he found out he was going to be serving his asshole to some real juicy throbbing cocks. He was so excited and so was I. I mean hello he’s working for me now. That asshole is paying bills around here. He is my new personal escort and he loves his new job. He gets to cream and slurp on cocks all day. I am sure he’d be doing this for free if I didn’t come up with this bright idea. I have this rule where they have to roll the money up and put it in his asshole. Then he has to waddle over to me and squat over the palm of my hand. I take the money out of him and squeeze a bottle of lube into his ass. He gets down on all fours and those men plow his ass with no mercy. We have been practicing his walk and talk. I want him to be as feminine as possible. So far we are trying out some strap-on tits…I have been thinking if he continues to make this much money he can get breast implants done professionally. Time will tell. He’s a well behaved sissy slut! My BFF everrr!