Tag: Sissy training

Sissy Training is My Specialty, and So is Being a Loving Mommy

sissy trainingSissy training is my specialty, but I get a lot of mommy calls too. I guess you could call me a sissy mom. I have two trans sons. When I first started this job, my boys were schoolboys. Just young boys who liked to play dress up in mommy’s clothes and play with make-up. I knew then that they were special. I mean boys their age played with cars, Legos and trucks. They wanted to wear jeans and t-shirts. I let them be who they were. I think it is harmful to stifle a young one’s natural exploration to find out who he or she is. Most women are not as enlightened as me, though. I get all sorts of sissy phone sex callers who talk to me about how they were shamed and ridiculed, even punished by their parents when they got caught wearing mommy’s pretty things. Some of these men are pretty fucked up because their parents just did not understand.

I like to recreate the mothering experience with callers. Be that nurturing, loving, encouraging mother that they should have had. The kind of mother my boys have. My twins are living their lives in that in-between world that scares so many people these days. They go to an arts school where their creativity  can blossom. They go to a school where they can wear dresses and makeup to school daily. They have friends. They have boyfriends. They thrive socially. Regular school was not so welcoming, but I recognized that immediately and switched their schools. What mother does not want her offspring to thrive? When they are 18, they can decide if they want to have sex reassignment surgery, or become trans girls. Whatever they choose, I will support because that it what a good parent does. They support their offspring. And the best sissy trainer supports you. Nurtures you, encourages you and only punishes you in order to train you properly.  Mommy is waiting for you boys.

His first Sissy training session went well

Sissy trainingThere is a new sissy in town and he’s going to be squeezing his little link into his first pair of Sissy panties! He was at work when his asshole started feeling all slimy, he couldn’t help the tingly sensation that ran through his body.. He needed a fix, even if that meant in the parking lot of his place of employment.. Risky business! He took his 15 and called me up from the back seat of his compact car..

He didn’t have any toys so we settled with his fingers! He slicked his tips up by slurping and sucking them, like they were a fat cock.. Then smacked the excess saliva that he scooped up from his chin onto his manhole.. The windows of his car were not tinted but they did naturally fog after a while of his huffing from the sensational fuck he was giving himself; while I whispered humiliating things into his ear.. He or should I say she?

Anyway, the faggot is aware of his position.. Not every call will he get off; sometimes he may even just have to sit back and listen to me breathe.. I mean whatever it takes to talk to a hottie, you couldn’t stand a chance with in reality! uhh, the good in fantasy, huh? haha, Sissy training has only just begun, we went shopping for some fun stuff..

So far we’ve gotten a clear 7.3in soft realistic dildo to gag his bussy with and a plus size contrast lace mesh slip with a matching thong… It’s even got a satin bow that sits right between his knockers. I can’t wait until it arrives so I can show the world that a Sexy BBW does exist.. His juicy phat ass is going to look amazing sucking up a g string.. He has never had his man hole stretched with anything besides his finger.. Lucky him, I am the sexy bitch who’s going to break him in. Welcome bitch, You’ve got yourself the Best sissy trainer on the net, Good taste!

Domination phone sex Open Psyche

Domination phone sex

Sissy cunts need Domination phone sex in order to know their places. So many sissies running around here needing a proper mistress to fill their promiscuous cup.  Some men run around thinking they are capable of handling what they lack inside by pretending to be something they aren’t. Capable. They have no sense of direction and they will die lonely old men never knowing the satisfaction of submitting to a highly anointed mistress. The sub that can close his eyes and travel within to the darkest corners of his perverted sissy cunt. Realize he still have more within him that he could give over. Here in the beginning with Genesis the male sissy can carve out his space to blast open his psyche and realize what all can make his cock hard. What all can stimulate his pathetic mind into controlling or loosing control? What does a Femboy cunt feel to fill whole?

Best Sissy Trainer Coraline is Part Phone Sex Therapist Too

best sissy trainingI am not so egotistical to say I am the best sissy trainer here, but I am one of the best. I think what makes me good is that I am equal parts sissy trainer, mom and phone sex therapist. There is no cookie cutter sissy caller. You must know how to listen to a sissy when she is talking. Some do not want cock, some are all about the cock. Some want sissy humiliation, others want encouragement and nurturing. Some like to dress up in frilly dresses and be exposed as sissy faggots. Yet others just want to wear panties and stay in the closet. A good sissy trainer does not treat all her sissies the same way. I am part sissy phone sex therapist. I listen to my sissies. I help devise a sissy plan that best fits them. Jake for example, lives in a rural city. He wants cock, but it is hard to get cock in a small town. It is also hard to dress up and go to glory holes when your town has no glory holes and everyone in town knows everybody else. I have been encouraging Jake to travel. He finally did and he called me from San Francisco the other night. He wanted some encouragement on where to begin. In a large city full of gay men, sissy faggots and all kinds of alternative folks, Jake could blend in. I sent him to a glory hole first. I found an adult bookstore near his hotel and instructed him to go there. I was with Jake the entire time. He wanted me to hear him suck his first real cock and I did. I was like a proud mama bear. My months of sissy training finally being put into practice. It was hot hearing Jake swallow cock after cock. I helped Jake get what he wanted out of the sissy life. His journey is just beginning, however. Maybe I can help you with your sissy journey too.

Mistress phone sex whore Remi

mistress phone sex


I found a cute, little sissy bitch in need of a hot, mistress phone sex trainer to teach him how to take dick! I could tell from the start that I was going to have to be mean to this little whore! He was already dressed up all girly and slutty with thigh highs and a sexy thong. He had a nice, thick buttplug popped in his sweet, tight fuck hole but that wasn’t enough. My sissies are bbc sluts so they have to be ready to take the biggest and fattest cocks. I made that little slut ride a huge, fat dildo and stretch his sissy pussy wide open! I kept telling him what a pathetic cum whore he was and laughing at him. He looked so desperate and sad, bouncing on a dildo and dribbling drops of precum everywhere. I noticed that whore was making a mess on the floor so I started slapping him around and demanding that he clean it up. I made him stop riding that fat fuck toy, take it out of his whore hole and use it to scoop up the sticky cum that was all over the floor. Then I made that little bitch lick and suck the dildo clean for me while I kept telling him what a little bitch he was and how I owned him. I had so much fun with my new slut and I can’t wait to make him take a real cock tonight!

Sissy Panties: What color do you like wearing?

Sissy PantiesSissy panties always need to be worn when a pretty little plaything is in the presence of a hot young Princess like me. I can smell pathetic sissy losers in the air whenever a sissy faggot is well within range. Brainless sissys need to feel the silky panties against their little winky, it feels way better than fake men’s boxers. They can be so rough, a real puss needs panties after all. Catching a sissy wearing fake man clothes will result in caged punishment and withheld cum. There is nothing worse to a sissy bitch than knowing that he has to look and not touch. Why even push the envelope, put your panties on, and ring up the hot young mistress of your dreams? 

Maddie’s Punishment

Sissy Slave Training

I used to have the best sissy slut slave Maddie, but she’s been MIA recently. Where oh where have you gone Maddie?! I don’t know where you are or what you’re doing, but you’re NOT fulfilling your duties to the BNWO. Such a pity – you were the model sissy slut and you were going to train the other pathetic white slaves … but you’ve now lost your favor. As penance, you must wrap your shock collar around that pathetic clitty of yours and shock it until it’s raw and red. I’m going to see to it that you piss all over yourself and you won’t be allowed to clean it up. I’m also going to get the biggest, blackest, thickest bull to bend you over and stretch your pathetic hole open; you won’t be able to sit or shit properly for the entire month of March.

Here’s a math question for you: If a cock training is running south down your sissy whore throat at 40 miles per hour and another is pounding up your anal expressway at 50 miles per hour, how long until your pathetic, white cum dumpster self is a sniveling mess of cum and saliva? Or how about, how many pumps does it take to get to the center of a sissy bitch? I’m going to leave you chained up with your ass at the ready and your head propped up so your mouth is exposed and at the ready for a fucking so we can find out the answers!

Forced sissy training for Submissive Sub

Forced sissy training

Most subs crave Forced sissy training, but few can handle it. So many wanta be subs cry and beg for you to make them your sissy but most are too blind and inattentive to become a slave for a powerful mistress like myself. Most submissive males are voyeurs and not participants because they just can’t get out of their own way and submit to the pleasure zone. It requires a big commitment on the part of the mistress and slave. While I may use my cunt to obtain a following don’t be fooled. This cunt requires hours of service if you are to be collared by me. My slaves all know the different sensations of pleasure I demand. Not all pleasure is cut out equality and some pleasures have many layers underneath the top layer of pleasure. The question is are you ready to commit to exploration of pleasure? Are you ready to find out how pleasure can be used for and against yourself? Do you have the ability just to take another breathe and ride the waves of desire and pleasure only a mistress can bring to her submissive?

Sissy training with Miss Remi

sissy training

I keep a sissy slut with me at all times because you never know when a sexy bbc stud might need a tight, little slut to stretch, pound and explode into. The guys around my neighborhood know what kind of pimptress, slut I am. Everyone knows that I’m a sissy training whore and I always have a hot, little bitch for sale. I moved one of my favorite little bitches in with me so that I could dress her up and share her slutty, tight pussy whenever I want! I keep her dressed up in lingerie and ready to please a fat, throbbing fuck rod, at all times. I can’t tell you how hot it makes me when I get to watch men use her slutty mouth and pussy hole. I get to watch and I get paid for them using her cum holes! I bring her at least 3 men a day and it’s always the same. I watch her drop to her knees and start running her tongue all over his thick shaft. She uses her drool to get that fat dick dripping wet because she knows what’s going to happen next. I’m right there to encourage her while she’s getting a huge, monster cock rammed into her tight cunnie. I rub her cute, little clittie and tell her what a good slut she’s turning into and how our hard work and training is paying off. Every sissy slut needs an encouraging mistress to teach them how to please a man…


BBC sissy trainer blacks you

BBC sissy Trainer

It’s time to get and stay Blacked by your favorite BBC sissy trainer! I know how much you envy and lust after those swinging tree trunks of BBC. I too love the wonderful joy of having my ass clapped by a thundering big black dick. My thighs often break the speed of sound as my Black man fucks his snow bunny. I have that tight body of a white girl with a fat ass that black men can’t deny. I love you sissy maid bitches asking about my boyfriend. I always assume you mean Mike my black daddy. 

But yeah there’s Trent with his small dick out asking me if he can start working at the sissy maid hotel. He says it would be wonderful to work and pay my way through the salons they have created just for mistresses such as me. I get a discount and Sissy’s checks to pay for my stay. Of course, ill be staying in the BBC wing where they have Black men on speed dial for white women who need some strange, sweet-swinging dark meat. Trent is my boyfriend, I guess… But he really doesn’t get to fuck more than my ass on holidays and such. He spends more time worshiping black dick than I do. I have so much to learn! I guess I’ll keep him around to pamper me and learn the true art of being a sissy maid training to be a  queen for BBC.