1,509 results for sissy training

whipping these sissies into shape

Sissy maid training

 As a mistress, I will go to the end to ensure my sissies know their place. Whenever a sissy breaks a rule or two, that’s their ass getting whipped into shape. Physically or emotionally, I like to torture, depending on the situation. When you return on your word, I will make sure to have your ass broken into by a massive cock, and I know that sounds more like a treat than punishment, but I will up the ante in ways you would be too scared to experience. You know I’m going to put you on blast and show the world your sissy ass getting fucked while I handcuff you and whip your sissy body. I’ll let the world know all the pleasure you get from being a submissive sissy whore. Keep thinking your secret is safe to play all you want, but once mistress Alessandra reaches her breaking point, you will have to suffer the consequences. You’ll thank me later, sissy slut. Sissy Hypno Training Queen will get you where you need to be.

Semen Servings For Sissies

 

There are a few tenets of sissy slave training that absolutely have to be present if you plan on successfully turning a tender femboy into a full on sissified sex slave.  I won’t give away all of my secrets, I’m not a fucking idiot.  I will tell you one of the best ways to get a girly guy to submit to your will, though.  You absolutely have to make your slutty slave girly guys gulp down gallons of their own jizz to make sure they’ve completely given into you.

Every single load you let your clitty clowns fire off that no one had dibs on needs to go right back inside of them.  Hell, even the gobs of chunky cock goo they take in their gaping backdoor fagholes should make it into their pathetic he-whore mouths, so I hold a teacup up to their raunchy reamed out rosebuds and let them push and drip every drop of shitty dong sauce out so they have some strange cum to enjoy at tea time.

 

Sissy slave training

 

The jizz they get from other guys is a given, though.  Every real slut craves it!  If you want your girlyguy slaves to show they will do whatever you want them to do, serve them a saucer full of their own sperm soup or give them a shot of warm semen ceviche soi-meme.  Cocktails full of their own clittycock spunk mixer are a really easy way to get them loosened up and full of their own ball batter.

Whatever you do, if you ever hope of becoming the best sissy trainer ever, you should start making your butt sluts slurp down their own cock snot.  It just makes good sense.  Besides, do you want to have to clean it all up?  

 

It’s goddess to you!

Best sissy trainerIt’s goddess to you, you stupid little sissy slut! Why do I even have to correct you at this point?! You say you want to be my sissy pet but have shown you are not even worthy of my time! Why do you have to be told to suck the beta’s massive cock? You should be eager to get the chance to wrap your warm wet sissy mouth around his beautiful veiny rock-hard cock!  You are lucky to even be in our presence! You know you don’t even deserve that! You are scum sissy! The only thing you are good for is to be fucked and for you to suck, and you can’t even do that right?! Crawl over to me like the fucking filthy sissy slut you are! Don’t you dare look at me! You look at the ground sissy! That same ground that you should be worshiping because I walk upon it sissy! Now I’m going to sit up my throne which is your dirty little sissy face, and you are going to eat my ass! Clean this goddess’ fucking fat ass femboy! No, I don’t care that you can’t breathe! What does that have to do with me?! You better fucking figure it out sissy before I suffocate you with my dirty ass! Now lift your legs and take this huge cock deep inside your sissy hole! I would say don’t make a sound, but your face is a little preoccupied being my seat! Its ok sissy by the end of this training session you will be thanking me and kissing my fucking feet!

Humiliated by Jackie

sissy humiliation training

Not all sissies love being humiliated at first. It’s an acquired taste for some. But by the time I’m done with your sissy humiliation training, you will love it and your little clitty will get SO excited when I’m telling you what a dumb slut you are. And when I tell you how the likes of you would never be good enough to fuck me and you should just go ahead and commit to the sissy life? Well, that will just send you over the edge and you will be my little sissy slave forever. There are worse things to be, don’t you think?

You know, like the ugly man you have always been. You probably should never have even called yourself a man. It’s not like you were ever able to make a woman happy between the sheets. But you know who you CAN make happy? Me by sucking every single cock I put in front of you. And by taking every cock in your pussy that I command you to. You’re going to be a very well fucked sissy, but don’t you worry. The humiliation is always going to be there and you’ll love every fucking minute of it.

 

Small Dick is a Deal Breaker

sissy humiliation training

It really is a shame that you have such a small cock. You’re not half bad looking but that lil dick is a deal breaker.  What superior sexy woman do you know that’ll settle for a tiny little cock like that? You’re so fucking pathetic the only way that I would even consider speaking to you is if you paid me for it. And honestly, the conversation better be short because I don’t like to waste too much of my time on lil dick pansies. My clit is bigger than that teeny tater tot in your panties and your nuts look like two sad ass seedless grapes. LOL. Let’s just get that embarrassment of a dick locked away in Chastity so you can concentrate on worshiping my ass and twat. I don’t need your little cunt to start squirting while I grind my ass crack up and down your face. Nose dive in my perfect booty while you tongue fuck my pussy hole. I’m gonna make your ass work since you can’t make me cum any other way! When mistress begins to squirt, I’ll squat over your baby dick in a cage and let my wetness soak you. Once I’m done using you as my slutty toilet paper and cleaning my pissy cunt with your mouth,  you can use that juice to finish yourself off. You better make sure you eat up every last bit of cum after you’re done. You know I don’t like a mess!

Phone Dominatrix

Best sissy trainer

Hey slut!!

Look at my pussy and tell me how badly you would love to indulge in some juicy throbbing cock! I bet you wonder how good it feels to be deep inside of a pussy. I guess that’s why its my duty as your fairy godmother to make that possible!

Let’s get you all dressed and add some dressing to that nice tight pink sweet pussy of yours! I want to drench that pussy in lube.. Make it nice and wet. So we can take cocks together! I have been fantasizing about getting you dressed in a hot sexy lace teddy and having you and I lay on top of each other making it possible for a nice juicy cock to take turns ramming our silky wet pussies!

He can spread my tight rigid wet walls and slide his cock down low to bury it deep in your pussy. Oh my, him running his juicy throbbing hard cock down the center of my pussy lips and then rubbing all my juices all over your clity in circular motion! Fuck, I am so ready to have some fun! Let’s start training!

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!

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.

Forced Feminization Cum Showers

Forced feminization

Do I really have to tell you that part of the process of forced feminization is taking showers of cum from a bunch of femboy butt stretching, manwhore mouth craving cream spewing cocks?  Of course you do, you stupid boy-bitch!  What kind of fly by night sissification operation do you think I run here?!  I swear, sometimes you little clitty queens can be really fucking dumb.

Let me clear up any misconceptions for you; YOU WILL BE COVERED IN AS MUCH CUM AS I DEEM NECESSARY TO TURN YOU INTO A PROPER NANCY!  Is that clear, cockboy?  I hope so, I am speaking English and you’re not a total fuckwit, are you?  Your other sissy trainers might have let you get away with just throwing on a frilly little dress and wig and letting you just paint yourself up with a shit-ton of makeup like some kind of street whore then call your transformation good, but that doesn’t even come close to Mistress K’s masterful way of manhood manipulation.

I won’t even get into all of the mental shit I have to do to get you to fully give into me, or what kind of attire will be required of you to attend my training sessions.  I’m specifically talking about how much sperm you will have swimming around on, and in, you before I will be happy to show you off to the world as one of my perfect femboys.  You figure the average fertile male pumps out about 5 milliliters of jizz per ejaculation with around 100 million little swimmers in each ml, makes it about 500 million fuck pole tossed tadpoles per prick that penetrates you.  Multiply that by the hundreds of dirty dicks I’m going to make you please throughout this whole process and I figure I can have your donated sperm count up into the jillions in no time.  Month, month and a half, tops.

You get it, right?  I know a lot of people learn more by doing than any other method, so you’ll just have to swing by and let me show you.  I have a few cocks full of sperm packed spunk here waiting for you.  Let’s get started, shall we?

we need to have a meeting

sissy phone

As part of my sissy phone sessions, I love to have meetings and will expect nothing but the best from my sissies. I want to make sure you are intelligent and working smart. When you are jumping into the world of sissy life, you have to know you will not be the only person around who has ever thought of being sissified. You must come through with the work. I want to make sure you are sucking so many cocks and taking lots of cum. I don’t have time for games and will put you to the test. I will make sure you outdo yourself and show me you were born to be a sissy whore. I want to see improvement from your walk to your clothing attire to your personal dating life. You must show me you are all in so that I can keep training you and making you a complete sexy vixen sissy slut.