Category: 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?


Femdom Phone Sex Goddess Rebecca Will Have You O Your ?Kees

Femdom phone sexAs a femme dom, I love femdom phone sex of course.  Which means, I love  nothing more than toying with men’s emotions and reducing them to nothing but submissive sissy sluts. My allure was undeniable; dressed in the finest lingerie, my body perfectly accentuated by each curve and crevice on display for all who dared look upon me – Mistress Peace! With every step taken in those six-inch stilettos came an air of dominance that commanded respect while simultaneously breaking down any remaining shreds of masculinity left within their core.

I enjoyed watching as they squirmed under my gaze filled with both desire and fear knowing full well what lay ahead if they were lucky enough (or unlucky depending how you looked at it)to catch my eye tonight… Their pleas for mercy fell upon deaf ears as I pushed them further into submission time after time again proving just how little worthless cocks truly meant when compared against powerful women like myself who knew exactly how get what we wanted without hesitation or remorse!

My friends, all beautiful black men themselves, would often join in these little games helping me fuck our sissy boys harder than they ever imagined possible. The sight of their asses being pounded by not one but two (or even three!) cocks at once never failed to bring a smile to my face or turn another head towards us as we dominated yet another pathetic excuse for manhood right before everyone’s eyes!

Tease and denial phone sex: A Sissification Story

Tease and denial phone sex


Ah, pathetic losers, prepare to have your inadequacies laid bare. For I, the majestic dominatrix, bring you a tale of tease and denial, a symphony of humiliation that will make your tiny members shrivel in shame.

Imagine, if you will, the pathetic spectacle of Loserdom incarnate—a miserable excuse for a man, with a microscopic penis to match. So pitiful, so laughably small, that any woman who lays eyes on him can spot his deficiency. And guess what, little man? I’m here to rub it in, quite literally.

Your evening’s entertainment, as decreed by me, the glorious mistress, entails an exhilarating session of small dick humiliation, live on video. But wait, there’s more! I’ve got a cock ring that will accentuate your inadequacy, making your dicklette dance with Joy. Oh, the irony!

My sissy, you see, will be putty in my hands. While he drools over my curvaceous friends and I, our voluptuous figures leaving him warfare, we’ll subject him to a cacophony of teasing and denial. Our alluring assets will be the backdrop to his misery, as we remind him, loud and clear, of his minuscule manhood.

For such a pathetic sissy, attention is a precious commodity. And he will grovel, pay, and endure any embarrassment to catch a glimpse of our divine feminine presence. But let’s be clear, this sad little man doesn’t deserve any form of sexual gratification. His sole purpose is to amuse and be humiliated, a meek vessel for our amusement.

So, sissies, take note. This is the fate that awaits you if your manhood fails you. Embrace the ridicule, for it is the only attention you’ll ever receive.

Does my tale of sissification strike a chord, my fledgling losers?

Tease and denial for piggies w/ dicklets, cash for ass loser

Tease and denialStroke you little dick loser, you won’t be able to resist my Tease and denial… Just the sound of my sexy voice will have you on edge and the fact that you are finally getting attention from a woman. Of course, the only way for you to get any sort of attention though is by paying! Pathetic sissies like you aren’t worthy of an orgasm but the adrenaline rush you receive from having my attention gives your pathetic ass more than enough excitement… Doesn’t it? Every woman who you have ever laid eyes on knows you have a tiny dick just by looking at you.

Such a sore-loser sissy you are, no woman has ever taken you seriously, and neither will I.

On video is how you will be spending your evening entertaining my friends and me, through Small dick humiliation. I’ve got you a cock ring, I want you to tighten it up right at the base of your cock so we can get that dicklette of yours extended to its max capacity. It’ll be so much fun watching your dinky jump for joy while we tease you with our Big tits and asses.

A man like you would love a chance with hotties like us but we both know deep down inside you don’t have the self-esteem nor the cock to make you worthy. Anything for attention, right? Even if that means serving as nothing more than pure entertainment. There is only one way a guy like you gets attention from girls like us and that’s through Sissy humiliation.

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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Small dick humiliation at my hands for your wife

Small dick humiliation Small dick humiliation because your pin Prick isn’t worthy of any kind of words! My fuck machine is much better than your little dumdum sucker! Humiliation by fuck machine is what you need right now! Your woman sent me to seduce you into a date tonight. She is fucking tired of you thinking your cock of the walk with no fucking cock! I plan to treat you to a sensual massage and get your penis hard for me. At which time I demand you to show me. 

Small dick humiliation

I tell you that you are not a man and that you should never fuck another pussy! See, even your woman knows how much you need my Femdom phone sex is needed for a bitch like you. My fuck machine is ready as I pull the sheet off and make you watch me fuck my own brains out while your use two fingers on your tiny penis. With a deep guffaw laugh I tell you exactly what your wife text me.

“His dick doesn’t rub my pussy walls at all. He thinks 5 inches is average and he gets me off. I have faked every orgasm for the last three years. I’m so tired of dealing with a little boy in the bedroom. Please humiliate him and tell him how I hate his little dick. I never want to have him try to penetrate my pussy ever again!”  

Femdom phone sex

Make a cum drop in your hand and lick it up for me.  I want you to humiliate yourself for me. Beg for my mercy, you little bitch. After I cum the first time on this huge dildo I am going to dress you up. Oh, don’t be like that, some panties are not going to like you. How about some Dior lipstick and some, falses?   Now kiss my feet and thank me for humiliating you. Now lie on your back and spread your legs. I’m going to make you cum for me. Sissy humiliation at my hands goes farther and more intense the more humiliation I get to give.