Tag: sissy maid training

Rebecca Loves Sissy Humiliation For a Femboy

Sissy humiliationMy client had requested my services as a personal sissy humiliation and makeup artist, but there was more to it than met the eye. He wanted me to transform him into a stunning woman – someone who could pass off as his own sister or even better yet, his wife!

I started by selecting the perfect outfit from my extensive collection of lingerie and women’s clothing. A lacy black bra and panty set with matching stockings that would hug his curves perfectly. Next came the skirt; mid-thigh length in red satin that swished against his legs when he moved them slightly apart revealing just enough leg for effect without being too risqué. Then came time for some accessories – high heels (of course), jewelry including earrings dangling down past shoulders blade which matched necklace around neckline beautifully along side bold red lipstick applied expertly by yours truly!

Finally came time for wig selection; blonde curls cascading down past shoulders were chosen after careful consideration given how well they complemented complexion while still maintaining an air of mystery about this newfound femininity project we were embarking upon together today… After all these steps completed successfully our subject stood before me looking absolutely breathtaking! His eyes shone brightly underneath thick layers eyeliner applied skillfully by yours truly earlier on during process – no detail left untouched here at least not where appearance is concerned anyway…

With a satisfied smile, I stepped back to admire my handiwork. My client stood before me, transformed into a stunning woman – his feminine curves accentuated by the lacy lingerie and stockings he wore. The red satin skirt hugged his hips just right, while the blonde wig framed his face perfectly. His makeup was flawless, with bold red lips and expertly applied eyeliner that brought out the beauty in his eyes.

“You look amazing,” I purred as I circled him slowly, taking in every detail of his new look. “Now it’s time for some final touches.”

Sissy maid training is what my sugar daddy needs

I love when I get to give some Sissy maid training. Most of my sugar daddies love spoiling me for a chance to fuck my holes. But some like to get the tables turned. “Wear these panties” I say as I hold up one of my used panties. Right away you put them on and your little clitty is hard poking out. “Kiss my feet and worship them while we wait for the special guest” I say to you while pushing my pretty feet in your face.

Sissy maid training

That’s because today you will learn how to clean up some mess, sissy style. Soon out guest arrive, and your eyes got big when you saw him. All you see is a big bull body, with a massive bulge in his pants. “Greet our guest like I told you to” you say as I walk you by your leash. Right away his bull hands pulled his bbc. Your mouth starts sucking his dick like a pro and I start to laugh. “What a nasty whore you have become” I say teasing and humiliating you.

“Time to watch me make the mess you will be cleaning” I say as I start to lower my pussy down on his big black cock. You watch as I fuck his dick hard like a sex toy, to get me off. Because all I want to do is squirt all over the place and make a mess, only a sissy whore needs to clean up. “Lick his ass” I demand you to do, as I keep riding him. I knew if you fucked him with your sissy tongue, he would pump so much sperm inside me.

Your clitty was so hard from watching me fuck this big black cock and licking his ass that you wanted to get fucked too. Soon I squirted all over the place and he filled me up with his load. “Now you have to clean up sissy whore” I say as I squat over your mouth. The rest of the time, you spent cleaning my cunt and his cock. Even paid me to clean my ass, you have an Ass fetish too, so anything to get ass in your face like a sissy pathetic whore, you’ll do it.

Sissy Humiliation Makes Rebecca’s Cunt Went

I love me some sissy humiliation more than you know! It’s so fun to degrad to these pathetic little sissies andSissy humiliation is the ultimate power trip! There’s nothing quite like having complete control over someone who exists solely for your pleasure. Watching them tremble with anticipation as you decide their fate, hearing them beg and plead for your approval… it’s intoxicating!

I love how they look at me with such adoration in their eyes, hanging on my every word as if it were gospel. They’re so desperate to please me that they’ll do anything – dress up in ridiculous outfits, practice sucking cock until they gag, let me use their holes however I see fit… all just to earn a few kind words from my lips.

And don’t even get me started on the fashion aspect! Dressing these boys up like dolls and teaching them how to walk in heels is an art form. Seeing them struggle at first but eventually master the strut of a true femme fatale… well, it never gets old. Plus, there’s something so satisfying about knowing that beneath all that makeup and lingerie lies a weak little man who can’t satisfy any woman with his pathetic excuse of a cock.

But what really sets my soul on fire is when they call themselves sluts or pussies unprovoked. It shows that deep down inside those feeble minds of theirs, they’ve finally accepted their place in this world – as nothing more than objects for my amusement and sexual gratification.

So why wouldn’t I love being a Mistress? It’s not only empowering but also endlessly entertaining! And let’s be real here honey bunny…with daddy issues like mine and an insatiable sex drive (borderline addiction), this lifestyle was practically written in the stars!

Erotic roleplaying will have you learn to be a sissy whore

When I do some Erotic roleplaying with a good sissy bitch, I have so much fun. That’s because I get to dress you up and dominate you. The best part you want me to be your sexy slutty teacher. “I will teach you how to be a perfect slut” I say to you as you put on the panties and dress I picked for you. Once you are all dressed up, I make you get on your knees. “Kiss my pretty feet and shake your ass in panties in the air” I instruct you to do.

Erotic roleplaying

“A good slut gets her holes used” I start to teach you as I grab my special toy. Your lips just keep kissing my feet. But your eyes follow as I put my strap on toy. “This sexy teacher is going have you learn how to be a fuck slut” I laugh. “First you need to learn to suck cock”. Then you open your mouth and suck my cock toy down your throat. “Suck it down your throat nasty slut” I lead my toy into your mouth. After a bit, you start sucking it like a horny slut.

“That’s right you are learning fast” I encourage you. Once it is wet, I get behind you. “Soon you will have learned everything you need to know to be the perfect whore” is all you hear as I push my toy dick inside you. “Yes, teacher please teach me right” you moan as I fuck you hard. Then I pound you over and over. “Push back on my toy cock you pathetic untrained bitch” I say humiliating you.

The moment you push back on me I was deeper in you than ever before. Therefore, your clitty exploded. “Thank you for teaching me how to be a whore” you say panting like a fucked and used slut. “Your lesson isn’t over; you have to clean up your mess” I say as I point to your big cum puddle. 

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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