Category: 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.

Sexy dominatrix gets spoiled by paypiggy for bbc

I love when I get to be the Sexy dominatrix, I love being with a sissy paypiggy. “Make sure you come over dressed in panties and with a wallet full” I demand teasingly. It excites you to be bossed around and humiliated in panties. Especially when you tribute me. It makes your clitty stir every time you spoil me. As soon as you walk in you hear, “take everything off and let me see your sissy outfit”. You watch as I giggle and point at you.

“Now get on your knees like a good little piggy and oink, while I count my tribute” I instruct you to do. As soon as you see me counting your sissy clitty cock stiffened up out your panties. Then you oink and my bbc bull buddy walks in. When you see his big black cock swing in between his legs. Your mouth starts to water as I grab his big dick with my hand. “I want you to show your mistress how hungry of a piggy you are” I say as I push his big black cock towards your mouth.

Sexy dominatrix

The way you have been needing to be used is shown, when you tribute me as you suck his cock. “That’s it, clean my juices off his big black cock” I cheer you on. Then I spank your clitty and tell you how you will be fucked next. “Thank you mistress, I know I am worthless and must tribute”, you say as you get into position. Before my bbc bull slams his cock in your worthless sissy cunt you tribute me. I watch as you get fucked hard until you squeal like a piggy.

“That’s it oink for your mistress” I cheer you on ad I count my tribute. It is so fun having a good sissy to spoil me and milk my bbc bull. Finally, your eyes get wide as you feel the sperm pump in your sissy cunty. That’d when I looked down and your sissy clitty made a big mess in your panties. “Before you leave you must tribute your mistress and clean up my bull’s cock” I instruct you with a big smile on my face. 

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 you need from a mommy

The Erotic roleplaying you need is particular and that is why you come to me. “First you must undress” I say as pull out a special toy. After you have all your clothes off, I make you bend over. “Mommy is now going to spank you for being so naughty” I say teasingly. It is what you have been wanting mommy to dominate you. After you are bent over, I start to spank you with my dildo. “Tell mommy you like being punished” I say in our roleplay.

Soon after you had found mommies dildo, you wanted to know what it felt like. So, you started kissing it and sucking it. That’s when mommy found you. But you didn’t get the punishment you needed. Therefore now, you need roleplay from this mommy. “Mommy I need you to punish me” you whimper like a horny slut. “Thats right bitch, you needed mommy to find you” i say as i start to push mommies’ dildo in your mouth.

Erotic roleplaying

“Taste mommy and clean her toy up” I instruct you to do. Like a hungry bitch you slurp up mommy’s toy. Roleplay mommy had just used it, so you can taste her off of it. “Since you want to be a slut, mommy will show you what it takes to be one” I say sternly. Once my toy was wet and gooey, I start to rub it on your roleplay sissy son hole. “Ask mommy to fuck you” I spank and tease you. “Please mommy punish me and fuck me hard” you moan like a pathetic whore.

After that I push momma’s dildo inside you. “This is how mommy fucks her pussy. I grunt as I fuck you with my dildo. “Mommy likes it hard and so will you” I giggle and fuck you. That is what you needed from your roleplay mommy, and you started cumming all over. From now on you need roleplay mommy to punish you right. 

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. 

Masturbation Mayhem: A Telefuck Tantrum

Sexy women masturbating

Hey, perverts! Want to hear something that’ll make your dicks throb and your pussies drip? Step into the world of telefuck frenzy!

You won’t believe the filth that’s about to unfold.Your truly—a masturbation mastery, a telefuck expert, ready to blow your mind. And damn, will you cum hard!Last night, Kyle experienced the time of his life. Why? Because this girl here knows no bounds when it comes to mind-blowing phone sex. I’m the queen of dirty talk, and your fantasy fuck.

Butt plugs, powerful wands, and cock rings—oh my! I had Kyle’s ass and cock dancing to my tune. And that remote-controlled stroker? Yeah, I piloted that motherfucker while he was at my mercy.Our session? It was a bisexual blast! I painted him a picture of two sexy ladies, their tongues entwined, exploring each other’s juicy holes. And damn, he was sold!I guided his rod, his balls, making him see stars. While he instructed me to play with my pussy, I imagined him—a horny god, ready to exploit. And explode he did, all over my hungry mouth.

But the fun didn’t stop there. No, we were just getting started. You see, Kyle’s a quick study, and soon, he was returning the favor. As I played with my toys, he controlled that stroker, sending shivers down my spine.

The mutual masturbation, the dirty talk—it was a symphony of seduction. We brought each other to the brink, again and again, until we were both spent, panting.

But hey, that’s not all—I’ve got more stories that’ll make you jizz!

So, grab your toys, and let’s cum together!

Savage Forced crossdressing with Mommy is truly sublime

Your Mommy domme will push savage Forced crossdressing upon ya! I have been too easy on you little slut. I want to put you in a bikini that will make you feel like a dumb slutty bitch. You’ll feel so degraded and pathetic while I make you model it for me. It will definitely be bright pink string bikini. It will be so tight your hungry boy pussy will turn it into a thong!Forced crossdressingI know baby, you wish to be like Mommy. Now, we can try but you will never truly be a hot sexy woman like me. However, your throat and bussy are very useful to me. Sex with BBC is so much better after Mommy humiliates you. I make you strut your stuff for me and my sexy friend’s thick BBC. I order you to bend over and show my friend how hungry your hole is.

Your Phone sex mommy loves it when you blush. Once I see those bright red cheeks beaming with humiliation, I will allow my little sissy mouse to suck on my big black cocked friend. Doesn’t that taste so good? Don’t you want to suck down all that man juice?Forced crossdressing

You will not stop sucking, just like little slut you are. I don’t care if your throat and jaw hurts, you are doing the only thing you are good for so better not stop. You better convince me you will worship every part of my perfect body before you even get a scent of my sweet wet pussy and that means a lot of gagging on fat cock.

Tap into something deep and primal. You will embrace your inner femininity, and you’re doing it for me, your mommy domme. I expect nothing but the best from my sissies, which means you’d better be ready to bend over and take what I give you. And if you’re a good boy, if you make me happy, then maybe, just maybe, I’ll let you suck his cum out of my warm wet pussy.

But only if you promise to be a good little sissy and do exactly what I say. Because that’s what Sissy humiliation is all about: submission, obedience, and the joy of serving your Goddess.

 

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!