Tag: sissy humiliation training

Sissy Humiliation Training With Mistress Bailee

Sissy humiliation training Sissy humiliation training with Mistress Bailee is never boring, I put my potential slaves through a grueling training process, nothing is taboo or off limits. I make sure my future slaves know they will never be in control and will always be dominated by my big cock warriors or myself. 

One of my requirements is that you must take cock, in your ass and mouth whenever and wherever I say with no question, so if i want you to go in a bathroom at the mall and get your hole stretched out, I expect you to go get fucked. 

Another requirement is you must get off on being my cuck clean up faggot, I want you to look forward to watching me get fucked and wait patiently to clean the cum from my cunt, as well as my lovers’ thick cock. 

Sexy lingerie and make up is a most as well, all hair must be removed, I want your skin soft and silky at all times. 

The only questions you are allowed to ask is whose cock will you be servicing today, follow these rules and you will be a very successful sexy sissy faggot for Mistress Bailee. 

Humiliation Phone Sex With Pathetic Sissy Sluts

humiliation phone sexHumiliation phone sex, it’s the best is it not? Oh, you’re such a pathetic little sissy boy. It’s time for your humiliation makeover! I can’t wait to dress you up like the slutty little girl you are and parade you around for my friends to laugh at.

I grab a lacy black bra from my closet and toss it at your chest. “Put that on, faggot,” I command as I watch with amusement while your hands fumble with the clasp behind your back. Once it’s finally on, I step in front of you and adjust the cups so they accentuate your tiny tits perfectly.

Next comes a pair of black lace panties that barely cover anything – just how we like our sissy sluts dressed! You struggle to get them pulled up over those huge balls of yours before finally managing to stuff yourself into them like the disgusting cocksucker that you are.

Now for some sexy lingerie on top! A red silk corset goes next, cinching your waist tightly and pushing out what little chest you have left even more prominently than before. Then comes a short black skirt that barely covers your ass cheeks when combined with those ridiculous high heels we made sure were part of this ensemble earlier today (which also happen to be strapped onto each one).

Finally, just because we can never resist adding an extra layer of humiliation…a frilly white apron goes over everything else – complete with ruffles along its hemline! Your face must be bright red by now as you stand there, looking like the pathetic little sissy girl we’ve turned you into.

I grab my phone and start snapping photos of your exposed body, laughing hysterically at every click of the camera. “Look at this disgusting faggot!” I exclaim to my friends, who are doubled over in laughter themselves. “Isn’t he just too much?”

One of them grabs the apron strings and yanks on them playfully, causing you to stumble forward slightly before regaining your balance (or rather lack thereof). Another friend steps up behind you and starts playing with those tiny tits poking out from underneath that bra – pinching them hard enough that tears well up in your eyes but not so hard that they actually hurt…because then it wouldn’t be funny anymore!

We continue like this for what feels like hours: taking pictures, touching inappropriately, making lewd comments about how pathetic our little sissy slut looks dressed up like this…all while laughing maniacally at every moment. And all because deep down inside where no one can see or hear us – including ourselves sometimes – we get off on reducing others to nothing more than objects of humiliation…and maybe even lustful desire once they’re completely broken down emotionally enough by our cruel gamesmanship.

Humiliation Phone Sex Master, Tanya, Will Make You Cry!

Humiliation Phone Sex

As a Humiliation Phone Sex Master, I only want to hear you cry.

I know how much you love big black cocks, even when you try to lie to me i know the truth, you little faggot.

Admit to me how much you like choking down cocks when no one is looking.

Imagine everyone finding out you love being a little faggot whore for men with huge cocks—how embarrassed would you feel?

You can’t cum without them! Even balls deep in pussy, you are thinking about cocks cumming all over you.

Drinking all that black man’s cum down your throat.

Lift your ass high in the air like the good little fag you are and get yourself ready to be dominated by those big ass cocks.

Bend over, baby, and let me watch you take it and get yourself stretched out real good.

 

See More on BlueSky  &  Follow Me!

Sissy boy wants to dress up like a littleone to get smacked

Femboy training

You’re a gluten for punishment. That’s all you need and want to survive. Calling me up and begging me to brutally beat you into being my submissive little slave boy. You love this shit and so do I. “Please mistress Jackie dress me up”, you all beg me for the same thing and I’m more than happy to help you dress like the little one you long to be. From panties to your hair I’m here to femboy you up. It’s what I do and love best however I will be you to a femboy slave faggot bitch boy test, are you ready to perform for me?

Femboy training is what I do best baby

I wanna make your eyes glitter with red cheeks and lips too. High heels and a short skirt. Any male I bring around is gonna look at you like a little snack. This is what you dream about while you live an unhappy life. Always looking forward to your time with me, don’t you? You desperately wanna take off those shlumpy clothes you have to wear all day and slip on some cutie panties, bra, hose and heels. How cute do you wanna be?

Humiliated with your ass out

Once I’ve got you looking in pretty it’s time to spread that man pussy of yours, I’ve got a big beef stick to stuff that muff. I love it when you boys bend your asses over so I can whip you into shape and your getting spread open like cheese and filled to the brim. Bummed rushed by a massive 13 incher, so good your sweating and thrusting at the same time. Sweet sucker starfish looks better when it’s stuffed with his low hanging fruit dangling from you. So while your getting stuffed look up at Ms. Jackie and tell me “how good it feels to be a lovely lady”.

God damn, I love watching your male pussy cheeks flapping. Dressed to a tee, and I prefer this getting done to you while your in heels. Can you stand it baby? Once you call me I’ll tell you what else this big fatty beef stick’s gonna do to you..

Phone Dominatrix is my favorite kind of phone sex play.

Phone dominatrix sex is the best kind of call I can get…nothing beats training a dumb little sissy into a good submissive slut!

Phone Dominatrix When I get a phone sex call from a baby boy needing a good mommy or mistress, I can’t help but grin and chuckle with the red-hot feeling of dominating a well-trained slut. I love imagining pegging my little fuck-sluts and fantasy raping their faces, asses, and little cocks.

My favorite thing to do to a submissive sissy slut is to jam my monster dildo cock so far up their tiny asses that their prostate causes them to explode–hands off. Making a good bitch cum for me on the other end of the line fills mistress with a deep, dark pleasure.

I use my vibrator and bring myself to a wet, squirting climax as my puppies tell me “yes mistress” “of course, mommy” and “yes ma’am.” A good slut works for MY pleasure.

Humiliation Phone Sex Gets Peace Off

Humiliation Phone Sex- I can’t tell you enough about how excited it makes me as a sissy slut trainer.

Humiliation Phone Sex

I love humiliating my sissy in public. It’s one of my favorite things to do. I’ll dress him up in the most ridiculous outfits, like a bright pink wig, a tight mini skirt, and a pair of high heels that make him stumble and trip over his own feet. Then I’ll take him to the busiest places in town, like the mall or the grocery store, and make him walk around with me while I point out all the things that are wrong with him.

I’ll make him wear a sign around his neck that says “I’m a sissy” or “I’m a slut” and I’ll make him repeat it out loud to anyone who will listen. I’ll make him do embarrassing tasks, like singing or dancing in front of people, and I’ll laugh and mock him the whole time.

I’ll also make him go into the men’s restroom with me and I’ll make him watch while I use the urinal. Then I’ll make him get down on his knees and suck my cock while I’m still standing at the urinal. It’s so humiliating for him, but it’s also so hot.

Sometimes I’ll even make him wear a diaper and I’ll make him change it in public. I’ll make him lie down on the floor and I’ll pull down his pants and diaper and I’ll change him like a baby. It’s so degrading and humiliating, but it’s also so sexy.

I love humiliating my sissy in public because it reminds him of his place and it makes him feel like the worthless slut that he is. It’s also a great way to get attention and to make people stare. I love being the center of attention and I love making my sissy feel like he’s nothing but my personal plaything. It’s the ultimate power trip for me and it makes me feel incredibly sexy and dominant.

Forced Sissy Training Zuri Breaks Faggots Down Completely

Forced Sissy Training

Look at you, standing there in your custom-tailored suit, thinking your bank account makes you a man in my presence. You’ve spent your whole life barking orders in boardrooms, but the moment you stepped through my door, your status became as flimsy as the place I’m about to put you in. This Forced Sissy Training is exactly what an arrogant, wealthy elitist like you needs to finally understand your true place at my feet. 

I might be a petite, tiny thing, but I have enough power in my pinky finger to break your fragile ego into a million glittering pieces. I want you to feel the weight of my gaze as I look up at you, mocking the very masculinity you’ve tried so hard to protect. It’s adorable how you think your money can buy respect here; in my world, your only currency is your absolute obedience. 

Get on your knees and start unbuttoning that expensive shirt, darling. I want to see those broad shoulders slump as I whisper exactly how I’m going to turn you inside out. You aren’t a CEO anymore; you’re just my newest project, a high-end toy that needs to be properly calibrated to serve.

As I circle you, I can smell the expensive cologne and the even stronger scent of your desperation. You’ve been craving this, haven’t you? You’ve been dying for a woman half your size to strip away the mask of the “great man” and reveal the shivering, submissive mess underneath. I’m going to make you trade that silk tie for a choker, and those leather oxfords for something much more humiliating. 

By the time I’m done with you, you won’t even remember how to stand up straight… you’ll be too used to crawling. My training is thorough, and I don’t accept anything less than total surrender. I’m going to push you until those “elite” sensibilities are completely shattered, replaced by a frantic need to please me. 

I want to hear your voice crack as you admit how much you love being reduced to nothing. It’s so addictive, isn’t it? The way the power shifts when I put my hand on your neck and remind you that I own every thought in your head.

Now take this dick up your asshole, while emptying your bank accounts with your pride being completely demolished. You’ll be my perfectly trained, hyper-feminized little secret, begging for the chance to come back and be broken all over again. Now, be a good little faggot and show me just how much you’re willing to sacrifice to stay in my favor.

 

Femboy Training with Tough Mommy Tanya!

Femboy Training

Mommy wants to do some Femboy Training on my little sissy boy!

I caught you looking at my bras and panties again, and I think it’s time we just dive right into you being my whore daughter.

Since you love my little panties so much, why don’t you put them on? That little clitty you have will fit perfectly!

I’ll throw on the matching bra and pad them with tissues to make you look like a mini me!

What a gorgeous little slut you are turning into.

You’ll be the perfect little hole for all of Mommy’s boyfriends with big black dicks!

They will have a blast stretching out that tiny bussy hole!

So be a good little sissy girl for mommy and bend that ass over and high in the air!

Sissy Phone Sex

See more on Mastodon! 

Best BBC sissy trainer, learning how to gag the best way

BBC sissy trainer

I’m a bit of a hardcore sissy fuck trainer. I prefer to dress you up as a little slut before the real mother fucking fun begins. I’m not easy on you. I wanna spread and widen any man pussy that cums my way and yours is looking pretty damn good. I can always tell when I do my sissy trainer that those boys with the extra tight bungholes haven’t had the BBC need to complete my nasty course. Are you down to get browned?

BBC sissy trainer, better get ready to get wrecked. 

I have a side fuck big black beautiful man who loves to partake in all my sissy training along fucking the shit outa me on the side. Before he busts your hole and rips, tears and shreds your insides out, it’s time to make you pretty. I prefer my sissy’s to sit at my vanity. Look at themselves as they go from manly to slutty. The makeup hair, bra’s, panties, hose and heels, your ready to get rolled.

My big BBC boy prefers his sissy faggots on their stomachs. So get on that bed and spread your crispy cookie open.

Now that I’ve made you so pretty, we’ll call you trick bitch. The sexy girl with a big flat ass ready to get pummeled. He reaches up your skirt and puts your panties to the side. I instruct him “go ahead baby, grab his nuts hard too”. With one swift punch he’s packed in your ass, his massive big black dingleberries smacking you. I love to assist to get my clammy moist and ready. Pulling your panties so tight while he’s slamming you raw. “Spank him good, make him beg to be called a faggot whore”.

Sissy humiliation training get’s me off, my pussy swells watching you get werked honey!

Humiliation at it’s best, I love this shit, being a trainer cums with prizes. while your screaming with blood soaked cum running down your panty hose your begging for him to pull out his BBC beast. “How bad do you want him to stop?” as I grab your balls. “Please please mistress I’ll do anything”.

He pulls out his massive black anaconda, dripping with your fecal shitty bloody cum and force feeds it down your throat. “Surprise boo, that’s what you asked for”. Your gagging and choking, clinging for life. This is why I’m the best damn sissy trainer around!

 

Sissy Maid Training For a Married Closet Sissy Boy

Roger Needed Sissy Maid Training. He is one of those little sluts that likes to be dressed in petite little outfits and given tasks. A Honey Do list. I put him in the perfect little French Maid outfit. Underneath that next to nothing skirt, the cutest pair of red silk panties, restricting his hard cock. It was so fun getting Roger Ready.

Craving Cock sucking, but You are the one on your knees?

He even went great lengths to perform each tasks I asked of him. I wanted him shaved completely. Not just manscaped cock and balls. I wanted those legs hairless, as well as his chest. I waxxed his body myself. To get away with it, Roger signed up for swim lessons. To keep his little sissy secret from his wife, Rog even signed up for swim lesson so he could keep that buttery smooth chest and silky legs. His cock would drip while we waxed his body.

Naughty Little Dick Loving Diva

I started by Making him Dress completely and while cleaning my house from top to bottom he would wear a vibrating but plug. I held the control to turn it off and on, make it buzz and pulsate. The best thing was that it had a little dial, so I could strengthen the intensity of the pulse and vibration. His butt hole was mine, and his cock belonged to me. Maid Training was just what he needed.

Rogers wife will Never Know

After and I mean only after, All tasks were completed would I dress in the sexiest lingerie. I’d also wear my harness and lock a nice always hard and ready, 7 inch dong in there. Watching Roger on his knees, he loved for me to ask what his Beautiful, Loyal Wife would think if she saw my fat hard rubber dick in his mouth. That’s when I took pictures. You never know when you might need to blackmail a little closet Sissy boy.

He always had to suck it good and deep, depending on what he did with that cock and how well he cleaned my house, I would ponder using his tight little starfish.

Should I fuck Him? or maybe I should fuck you instead! Let’s Bring that Fantasy of being dressed like a slut, and completely fucked to a reality, sweetface……

Sissy Maid Training

Want to see more sexy fun! Wbmt is your sexy one stop shop

Check Us out On Mastadon