1,562 results for sissy training

I blackmailed him

sissy phone sexThis little sissy slut was coming to me for training but for whatever reason he was very resistant. He even threw away all of his girlie clothes and panties and all that, can you believe that nonsense?? Well I was tired of his bad behavior so I went to his house and made him dress up with all the clothes I brought with me. Then I took a whole bunch of pictures and told him that if he eve disobeyed me again that I would publish them all and make sure that everyone he knew saw them. Oh boy he was definitely ready to obey me then! He was freaking out and crying and begging me to keep the pictures a secret, it was hysterical! I just laughed at him and told him that I would do whatever I felt like doing so he better keep me happy or else. Well, he handed me a wad of cash, took me shopping and promised that he would keep me happy so for now I will keep those pics to myself. I wonder how long he will last before he pisses me off…

Surrender to me

Sissy slave trainingYou’re walking around the house with your sissy clitty dangling down between your legs as you fantasize about who is gonna be the lucky cock that is going to get to fuck my perfect pussy next. This beautiful goddess hole of mine is so fucking full of cum from being pounded out non-stop. I’m so swollen but that’s exactly how I prefer to be! You are over in the corner masturbating your pathetic sissy clitty and daydreaming about how good it might feel to shove yourself deep into my cum-filled cunt like all the other luck horny real men get to do. Why don’t you shift your thinking and go worry about your bank account and how much i’m fuckin draining you all in the name of domination and erotic gratification. I love putting your heart in a blender and still you surrender your whole being to me, lol you truly are a lost cause! You’re such a worthless little bitch! Bow down and kiss my pretty toes while I pat you on the head and tell you what good sissy pet you are. Your sissy slave training really is coming along swimmingly.

Stretching Out My Sissies

Sissy girl training

My little sissy faggies need to get their fag holes stretched every single day after their daily chores. My personal faggot slaves love getting their daily stretching. They work tirelessly to finish their chores. I make those nasty sissies lick up all the leftover cummies on the floor from our last play time with their pink tongues. They got to work on those thick goopy globs of leftover cum and made sure to polish my black leather boots with their tongues. I made sure my sissy slaves were locked up tightly in their girly little pink cock cages. I have all of my sissies line up in a row on their hands and knees while I pull out my big strap on dildos. Each of my sissies must beg to get stretched out by mistress’s thick strap ons. I brought out the small white ones first that were 9 inches and then eventually I went bigger and bigger to really stretch those fag holes!

Let’s Get One Thing Str8, You’re not!

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That’s right you’re not Straight. Why would you call my adult chat lines to hear my big black cock fuck tales? You are my femboy, my bottom to my bull cocks.  I know you salivate for those anaconda black dicks. Oh, my baby, my pussy drips for my sissy men.  I know you need a good cock training. Now come into my playroom.  I’ll put on some tunes and you will start gyrating your hips as I find a locking cock cage. You want to be under my command. Cum when I say and not before! Look!  Your beautiful skirt is short so you can show off that cock cage when I command you too. I will be the young mistress who will be feeding you BBC in both ends. I know what you are! I wear the key to your cock cage around my neck proudly as your mistress and your BBC cuckold loving Princess! Bow to me I know what you are! Maybe if you’re a good slut I will help you fund a wardrobe! And feed you cum loads for dinner!  Cum to my sissy phone zone! sissy phone

Panty boy son

Forced feminization

Forced feminization is my specialty. It isn’t just weak men who seek me out and want me to break their spirits, sometimes women seek me out too. A hot milf sought me out and wanted me to take her teen son and turn him into her little sissy toy. He tried to resist, but men are so easy to control when you get their cock hard enough. I let him have a taste of my pussy while his mom stood and watched. His cock was so hard and he wanted to put it in me so bad that I could have gotten him to do anything! Men are pathetic. I had him down on his knees wearing a ballgag and pair of his mother’s sexy lace panties in no time. He was humiliated to be hard and practically naked in front of his mother, but I had him where I wanted him. I instructed him to lick his mother’s cunt for me and he did just as I said. After initial revulsion at the idea, he was soon lapping at his mother’s pussy like a good little slut. His cock was so hard for his mom that it was straining against the lace of his panties. I told him to lay on his back and stroked his hard little cocky through the lace panties before sliding them down and letting mommy fuck him. He was so ashamed and guilty about fucking his own mom, but he wanted it so bad too. His mom rode his cock and made him promise to be her perfect little pet. He whimpered at first and I gave him a slap on the side of his face. I told him if her ever wanted mommy’s pussy again he better be her good little slut. He was agreeing with gusto as he filled his mother’s cunt with his cum.

BBC Size Princess Humiliates You

sissy humiliation training

I love BBC! I am a black cock size princess! I love having my tight twat bottomed out right in front of your small white dick as you attempt to stroke it with your thumb and forefinger.  That is not a fucking dick. That is a needle, a canned sausage a fucking pathetic excuse of a dick that never grew.  Fuck, look at these hung 10 and twelve-inch cocks. Are you fucking drooling, is that little dickie harder? Omg, you want to suck them, your jealous that you will never ever have man meat this big unless it is in your mouth! I will let you suck them right before you help guide them into my bare sweet young cunt. Oh, how I moan for them. But, do you want to please me even more. Let them cum inside me and as you clean my creampie Black cock loving young pussy, make sure your ass is in the air white boy. You are fixing to get your first lesson in being a BBC loving sissy. Don’t come to me unless you are ready to be a slave to black cock. 

Slutty sissies are my toys

Sissy pantiesI love having a slutty sister that gets off to cumming in her pretty little sissy panties. You look sooo cute in your thigh highs & garter belt as you rub your clitty with your vibrator. Using you as my personal sissy toy is quite frankly my favorite hobby. You’re still developing into the naughtiest sissy that you can possibly become and I am there to guide you along every step of the way with my superior training skills. Let’s go shopping for some new outfits so that we can really have some fun playing dress up! Your bra and underwear match your bright pink lipstick that you have on those dick sucking lips of yours. Would you like it if I whipped out my big black cock strap-on and shattered your pretty little pussy open wide with it?! Well, I don’t really give a fuck what you think, I just like to tease you and see your opinion on how much it’s going to hurt to have such a massive chocolate shaft plunged into your pretty princess body. Your pink panties will be pushed to the side as you take a big ole’ fat dick like a good sissy should. You’re so eager, i’ve never seen anything like it! I guess you could say that my BBC training has paid off well. 😉

Hot Mistress Phone Sex

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This Mistress phone sex Sissy Trainer is getting ready for the biggest sissy summer parade. In the next few weeks, I will be hardcore training Sissy sluts from around the world. I will be enlisting Five special sissy girls who will show me loyalty by taking the biggest cocks I can find. Slurping, gagging and giving me sweet tight virgin ass holes to be fucked hard and deep.  And How does a  Young Mistress slut like me find Sissy sluts? They gravitate to my young tight body thinking I won’t mind a small cock, having not a fucking clue that I only will be fucked by the biggest and the blackest cocks! My mother was and is the biggest cuckolding queen making my dad her sissy slave. I grew up watching him grovel at her feet and when I skipped school it was on the wrong side of the tracks to find the thugs and football players who would fuck my Uppity Catholic school ass! Yes, this slut would slum it to be bottomed out and soon found that forcing my teachers to clean my pussy out of my cream pie became my addiction. So do you want to join my sissy parade? Only wearing the sexiest and best frilly outfits I can find? Knowing that you are under the command of the best sissy trainer on this side of the tracks? I command your presence to be my world class femboy! If you dare cross me I guess you will have to be a forced sissy slut! Because once I have my eyes set on you I do not back down, I get everything I want and if I desire you then you are my perfect fem princess and will do as I say! Come to clean my cream pie and stay to be my sissy slave!

Presley



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You know who I am, and you know why you’re here. I’m nothing like those other whores who do sissy girl training. I was named for the King, so it’s only fitting I am the Queen. I rule over those other sissy trainer bitches, and now I rule over you, too. Your body, your mind, your soul; pledge your fealty to one as radiantly masterful as me. I will instruct you perfectly in how to be a flawless Royal prissy sissy Princess. This is more than pantyhose and lace, pretty sissy girl. We will go beyond how to please huge kingly cocks.
Your upkeep will be my main focus, always as you will service only me. I will educate you in the best mannerisms for a sissy femboy Duchess in your forced feminization. I own you now, and you’ll do as I say. Or it will be off with your head, and I don’t mean the one on your shoulders. As my personal slave and handmaiden, I expect the best behavior no matter how horny you get in your chastity. You will hold your piss until I say you may be excused. Don’t you dare have an accident in the Court, beloved, or you’ll see that Snow White wasn’t the only princess who knew an evil Queen. The torment I can, and will, put you through is unimaginable. If you end up in my dungeon, my little girl will never see the light of day again. Only never ending torment. Is that what you want?
My new little love needs some femboy training, don’t you? At night, you can watch me Queen my bed, and play cum into my castle with the fat cocks that fill me up. I don’t keep a King to warm my bed, baby. His cock was too small, so he was my first prissy sissy Princess I ever made! You can watch me take huge pricks, and clean out my sweet Queenly cunt of all his juicy cum when he’s done, if you’re a good girl. If you really please me, I’ll let you take a thick load in that rosebud asshole of yours, or I’ll take that silly sissy clit out, and stroke it a bit. But, don’t you think about cumming. Every last drop, every orgasm, now belongs to Queen Presley.
Get me in a giving mood, and maybe you’ll experience some pleasure before this time next year. Welcome to my chastity castle, sissy girl. It’s the closest to Heaven that you’ll ever see, and as sweet and sultry as hell. And if you know what’s good for you, you’ll serve me without complaint as I turn you into the girliest royal sissy you’ve ever seen.

Ember



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I love being the best little sissy trainer there is! Silly little boys just need to be treated like live little dolls. You’ll have so much fun when we play dress-up in cute frilly dresses, stockings and adorable little panties and training bras. I have so much fun playing with my toys and training them how to be the perfect playthings. Do your best to please the big cocks and pink pussies that I bring home to you. Don’t worry, I’ll teach you how to take care of them! Do your very best and maybe I’ll even suck you off or let you fuck my perfect pussy with your little dick! Do you want to be my new toy? I think we could have a lot of fun together!