Tag: sissy maid training

Sissy maid stories from My countryside estate orgy

Sissy maid stories from a mistress such as I who has worked hard to build her empire, But Now Have to deal with getting the best sexy sissies as my maids and servants! Oh, I have a special plan for the bitches of my household staff. See, I have penchant for little dicked men, and love using them as personal housekeepers and ‘fluffers.’ You know I have assembled a team of sissy maids, all of whom are more than happy to serve their mistress in any way! 💋

Sissy maid stories from My countryside estate orgy

My favorite among them is a man named Tim. Tim has a natural submissive streak and loves nothing more than dressing in frilly maid outfits and doing chores around the house. He is also more than happy to service Mistress Gwen’s other male guests, acting as a ‘fluffer’ to get them ready to fuck Miss Gwen with big hard hung cocks!  Tim is always eager to show off his cocksucking talents and is always willing to be a cum catcher!  He is also more than happy to Lick a big load off his Mistress’s face as a sign of his devotion.🧚Sissy maid stories One day, I decided to throw a wild Sex party at my countryside estate. Inviting all of Sissy Whore Tim’s favorite hung men! It was time to put all of Tim’s Sissy maid training on display! I put him in his best sissy maid dress and put him on the floor. Queen of the sissy maids has a reputation to hold up, after all! The best sissy maids were on hand to serve and entertain.

Sissy maid training for Tim Shows at My Orgy!

Tim was especially busy, darting between guests with a tray of cocktails and offering his cock ‘fluffing’ services to anyone who needed them. The party soon turned into a wild and steamy orgy. Mistress watches with delight as her guests paired off and began to explore each other’s bodies. How proud I am as I saw Tim on his knees, eagerly deep throating one of the other 9-inch cocks! 🍆💦

Small dick humiliation is the cruel reminder you deserve

Small dick humiliationHello, mortals. Looking for Small dick humiliation? Good thing you found me, the illustrious and sultry Mistress Lena. You are lucky to have me grace you with my presence! I know, I know, you’re probably trembling in anticipation, wondering what filthy secrets I’ll reveal about my life as a hot, sophisticated domme. Well, wonder no more, for I am here to share with you the ins and outs of being a goddess among men.

Let’s start with the object of your desire, my perfect, heavenly ass. I can feel your eyes devouring it as I walk past you, your tongue begging for just a taste. But alas, you will never have the pleasure of touching or tasting something so divine, for I am far out of your league. My ass is a masterpiece, a work of art that deserves to be worshipped from afar. Bow down, mere mortal, and show some respect.

I know you can’t help but stare at as I saunter by with my Sexy legs!  They are long, toned, and strong as hell. The perfect complement to my round, irresistible ass. I can see the jealousy and envy in your eyes, the way you wish you had legs even half as amazing as mine. But no, you are stuck in your weak, feeble body, while I continue to strut around in my stilettos, flexing my powerful muscles.

And speaking of weak and feeble, let’s talk about your tiny, worthless dick. Yes, I know, I can see the embarrassment and shame on your face, the way you try to hide it when you’re around me. But there’s no point in denying it, for I can see right through you. Your pathetic excuse for a cock is no match for any pussy, I mean how did you become such a lame fucking loser?

You’re style is totally basic, its completely fucking pathetic. You try to play off like you’re a real man but in fact you are just a teeny weeny, short dicked sucker. Good thing you have enough cash to burn for my attention. my fiery, dominant personality will show you how small you truly are pig. 

As your new role as my Sissy humiliation slave, you will have to serve whatever cock I give you. No matter what the grith of the meat, it goes deep in your slutty sissy hole. I know, I know, it sounds like a dream come true for you, doesn’t it? 

You need to be at the mercy of a hot, sophisticated mistress like me, doing my bidding and worshipping my every curve. And believe me, I will make sure to take full advantage of your weakness and obsession with me. I will be sure to dress you in the pinkest, frilliest outfit just to add to the humiliation. And of course, I will make you bend over and take it like the worthless sissy you are, All while I laugh and mock you and your clitty will be begging to bust.

Don’t worry, my dear sissy, I will be fair and just in my domination of you. I will give you the chance to prove yourself to me, to show me that you are worthy of my attention and affection. And who knows, if you’re lucky, I might even let you touch my perfect body, as long as you worship it properly. You need to show the proper amount of respect and devotion. Bow down slave and submit to my will!

 

The Sissy Switch: When Roles Reverse

Sissy maid training

I stood beside my husband, watching our guest, his eyes downcast, anticipating my instructions. The role reversal was a thrilling twist, as I, the sissy trainer, prepared to transform another man into a submissive slave.

The sight of my husband’s chiseled physique, contrasted by the submissive male’s slender frame, ignited my desires. I began the training, my voice firm and commanding.

The submissive’s eyes widened as I presented him with a skimpy maid’s outfit, his cheeks flushing in embarrassment. I ordered him to change while my husband and I shared a mischievous glance.

The new sissy emerged, his small cock peeking out from the lacy maided panties. I smiled, relishing my power, as he blushed, aware of his humbling situation.

I made him work for his pleasure, starting with some cuckold fantasy roleplay. I had him clean the entire house—vacuuming, dusting, and mopping—with his tongue and tiny sissy hands.

Then came the moment I’d been waiting for. I straddled the submissive’s face, forcing him to worship my husband’s and my cunts. He licked and sucked, his nose buried in our steaming folds, as we moaned in delight.

But the true test was yet to come.

I instructed him to take a huge dildo, penetrating his willing ass, while we watched, masturbating to his humiliating performance.

He pleaded for more, and I granted his wish, riding him hard, dominating his body as my husband cheered me on.

The night ended with us satisfied, the sissy remains a quivering mess, and I, proud of my sissy training skills.

Sissy humiliation trains your tongue for the whore Olympics!

Sissy humiliation

Sissy humiliation trains your tongue for the whore Olympics! I have an eye for sissy sluts. They love to pretend to be so manly, but I know what’s packing in between your legs. A little clitty just begging to be abused. 

I’m not afraid to push the limits. I’ll make your tongue work non-stop, and your bussy won’t be spared either. I’m here to train you to be the best whore you can be, and I won’t settle for anything less.

My sessions are not for the faint of heart. I demand obedience and submission from my sissies. You will do as you’re told, and if you’re a good little slut, you might just earn my praise. But don’t worry, even if you’re not the best, I’ll still make sure you’re thoroughly humiliated.

I expect Great blowjobs by that slutty mouth. I want tears streaming down your eyes and snot pouring out. Your makeup will be smeared all over your face when those cocks shoot you up with splooge. You’ll eat out my cum filled ass while I torture your sad little clitty. So tiny, may as well turn it inside out!

But what sets me apart from other dominatrixes is my attention to detail. I’ll make sure every inch of your body is soaked in cum and humiliated. From your toes to your clitty, nothing will be spared. I take pride in my work, and I’m not satisfied until I see my sissies broken and begging for mercy.

You’re a whore who needs extreme Forced feminization, you have no choice. I’ll make you dress up in the most embarrassing outfits and parade you around for all to see. And don’t think you’ll get mercy from me, I’ll make sure you’re the laughing stock of the entire town.

I’ll make every sensation and emotion come to life, and you’ll be left begging for more. You will be pushed to your limits and you’ll see just how far you can go. So come on, sissies, call for me and let’s get started. I promise you, you won’t be disappointed.

 

Summer Sweat: When Phone Sex Hits Different


Princess phone sex

 

Hold up, guys! I’ve got a story that’ll make you sweat like it’s the freakin’ sauna in here. It’s a steamy June afternoon, and I’m chilling at home, enjoying the sun when I get this random call. Usually, I’d ignore it, but something about the number catches my eye—it’s a bit funky.

So, I pick up, and oh my god, this guy has the smoothest voice ever. He’s got this kinky twist, saying he wants to play a little game called “Princess Phone Sex.” I’m usually not into this stuff, but his seductive tone draws me in.

He starts off by calling me his little princess, which is kind of cute, but then things take a freaky turn. He wants me to strip down to nothing, stand before him like a present waiting to be unwrapped. Yeah, a bit odd, but who am I to judge? I play along, describing my every move as I disrobe.

He’s got this thing for completeness, so I make sure he knows every curves, every dip, and every sexy bit of this fine ass body. He’s turned on, I’m turned on, and things are getting damn steamy. He asks to inspect my goods, and I let him enter every freaking crevice of my body—a full body massage, if you will.

His fingers aren’t enough, so he goes deeper, fingering my pussy, playing with my butt. We’re both breathless, and the temperature in the room is soaring. I grab his cock, tweak his nipples, and damn, he’s loving every second.

It’s a phone call that goes down in history. We’re both moaning, panting, and sweating like crazy. And when he cums, he does it with a bang. Shot after shot of creamy goodness—I think he chose my tits for the grand finale.

Who knew a random call could lead to such a fiery afternoon delight?

 

Sissy Maid Training With Rebecca

Sissy Maid TrainingAs a therapist myself, sometimes forcing some sissy maid training to get your small cock sissy’s in line is not only fun (for me) but necessary for your pathetic little loser selves. I mean, you are existing to serve because we all know you are not serving anything with what’s between your legs. By the time most sissys come to me, they’ve accepted that they are nothing more than little sluts that need their holes to be used and abused.  Some still struggle with thinking they have some self worth, which is far from the case and I need to take them down a few notches to make sure they know where they stand.

So after you come into my office, we will strip you down to nothing.  Your little worthless cock dangling right there in front for me to laugh at.  I will proceed to give you your little maid panties and little maid dress with the strappy heals that you must do all your tasks in. The tasks you will do will range from using your little pussy to dust my enter office.  I will make you clean my bathroom with your tongue making sure you get all the nasty little crevices all around the corners.

I will then make you have madatory dildo sucking and fucking to practice with my dildos because you never know when it will be needed to take a huge cock for me.  Sometimes I need sissy’s t suck big black cocks to get them hard before they stretch my pussy out.  Sissy’s seem to love this part of their maid duties. Sometimes, I will even let you come up to cunt and clean the cum out. I love watching your slurping ap=sssa

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Sissy humiliation for a fag hubby who needs trained

Sissy humiliationSissy humiliation at my hands means that little bitches get their Just deserts. Not only am I known for my excellent pussy pounding skills, I fuck a tight ass just as well! I’ll leave you in a blur as I take your wife and bust a nut with my silicone cock. Oh, did you think your ass would be safe from the priestess of anal whore fucking.

Fag🦄

I have humiliated my fair share of small dicks! You are not the first, but it will feel like the first time as you confess the sin of not having enough penis for me or your wife. Soon you will be pressured to be the best fembot around with a smidge of Forced crossdressing! 

You will never be able to forget me and the pleasure I gave you. You will learn your place and be grateful for it. Your life will never be the same.

Sissy humiliation for a small dicked married little bitch in panties!🩲

Your wife Sarah hairy ginger pussy sure does love how I fill her to the brim with my strap-dick! Look at her hollering and begging me not to stop.  You will learn to love me and to serve me. I will be your Teacher and your goddess.

Sissy bitch💫

I will be the one in control teaching your wife how to fuck you properly. It takes nothing to have you dressed in her dirty panties, stockings, and bra. Next, I help her harness herself up and come at you with a big swinging dildo. I hope you are ready to be fucked you little pathetic bitch boy! Mother fucker you better take every inch of it, and enjoy it!

Your wife and I will make sure you never forget this fagging out night! Now get down on your knees and worship me, BITCH! Get ready for the best Forced feminization of your life!!!

Cum on boobs is what you will clean up

When I get Cum on boobs, I call my favorite sissy bitch. He loves the taste of nut and that is why I have him always come over to clean me up. When I know I will be having a fun night of fucking my sissy bitch comes right over. “First I want you to fluff him for me,” I said teasingly. “My lipstick is too expensive for me to be sucking cock. Then right away he got on his knees in front of my fuck buddy and started slurping on his cock.

Cum on boobs

“You were hungry for cock today, but you won’t get his nut yet” I said laughing. Then I pulled my panties off and spread my legs. “Lick my ass and cunt, make it wet for his cock”. Since I love getting my ass licked, I make my sissy bitch lick it for me. That’s because I have an Ass fetish. “Wiggle your tongue” I say as I push my ass on his mouth even more. As soon as my cunt was leaking, I slammed my wet pussy on my playmate’s cock.

“Lick his ass lick i make you lick mine” I moan out as I ride his dick. When he was about to cum, I jumped off his ready to explode dick. Then he started spraying my tits with his big load. “Now clean my tits” I say to my sissy bitch friend. Just like that he starts licking the cum off my boobs. Once I was all clean my playmate was ready to fuck again but I wasn’t going to use my pussy. I was going to use my sissy bitch maid’s pussy. 

Forced crossdressing will help you embrace your inner feline

Forced crossdressing Most men try to blame me for Forced crossdressing but I know that’s exactly what they came for… Guys want me to dress them up like sleazy sluts so they can join me for a girl’s night out. They know hot girls have more fun and I am a black cock magnet! Black men just can’t keep their eyes off of me and Sissy white boys would do anything to get the attention I receive. Well, my latest slave slut is a guy I was once dating… He is a subscriber to my camgirl account so he knows firsthand of my great service of Big black superior cocks.

He catfished me… He sent me photoshopped pictures of himself with a huge dong…

I mean the depths this loser went just to get a taste of my Shaved wet pussy. He is so good at oral I didn’t think twice the first few times he came over and enjoyed my sweet pussy.. It was when my foot brushed up against his cock through his denims that I noticed he wasn’t packing what he said he was… I didn’t say a word, instead, I waited for him to get in the shower and barged into the bathroom while he was butterball naked.

To my finding, he was standing in front of the bathroom mirror with my bra and panties on… When he turned his face I noticed my sheer pink lipstick coating his lips. I wanted to be upset but I couldn’t help but burst out laughing.. He dropped to his knees and begged to be me! Well, that was the first night I dressed him up as a Sexy babe and we took on the night together… Now, he takes cock in his sissyholes and gives me all the money he makes.

What a good sissy slave slut he is.

Sissy humiliation Mistress Rebecca Trains To Take that BBC

Sissy humiliationSissy humiliation brings out my Femdom side and boy do I love the feeling my pussy gets when it tingles thinking about those sissy’s! I absolutely adore seeing those sissy boys all dolled up by their mistresses. It starts with your panties, they love the way they feel around their little cocks, huh? Then your clothes, all your slutty little outfits they graduate into wearing. The way they strut around in their heels and skirts is just too damn cute! And when it comes time for me to give them my big black cock? Well, let’s just say that nothing gets me going quite like the sight of a beautiful woman taking what she wants from her man. Or from her man turned sissy.

I love how pathetic they are as they take my huge dick deep inside them. They moan and whimper like little bitches while I pound away at their tight ass pussies. Their eyes roll back into their heads as if begging for mercy but really craving more of of the hard dildo strapped onto me, pounding them over and over. It makes me feel so powerful having these sissies under my control as I fuck the shit out of them. Making them suck the dildo like a real cock, completely degrading them calling them names like a “faggot” or “cocksucker”

The sound effects coming outta these pretty mouths… “Ungh!” *slurp*  The way they shake and quiver under my relentless thrusts… It’s like watching a live porn show unfold right before me. And when I finally cum inside them? Oh, honey! That’s when things get really good. They groan in ecstasy mixed with humiliation as hot sticky loads fill up every crevice of their feminine bodies – proof positive that only someone like me could ever truly satisfy them after being transformed into these beautiful creatures by their dominatrixes .

And let’s face it – who doesn’t love seeing those pretty little lips wrapped around a big black cock after you’ve had your way with them?