Sissy Makeover Stories: Real-Life Transformations

Sissy Makeover Stories: Real-Life Transformations

Here’re 2 sissy makeover stories for you:)

HE BECOMES…

He stands awkwardly at the door, unsure whether to ring the bell again. There are no sounds from within to tell him he’s expected. Is this the right place?

Sissy Makeover Stories

Suddenly the door opens, making him jump just a little. She’s not what he expected – casual clothes, hair tied back, barely any makeup and an easy smile. Yes, it’s the right place. She greets him by name and ushers him in.

Safely inside, he finds himself nervous again.This isn’t what he imagined. It’s too… too normal… Just a normal house. No signs of what they had discussed at length before. She takes his coat and offers him a drink, which he accepts politely. Standing there, he’s not sure what to do next and starts making small talk about the journey.

She waves the conversation away with a casual flick of her hand. “Let’s get you ready.”, and she turns and leads him through a door.

It’s still disconcertingly normal. A neat and prettily decorated bedroom with a window letting in plenty of light and a large dressing table. When they had discussed this earlier, she had sounded so dominant, so fiercely deviant. This seems so much at odds with those urgent confessional emails, her determined questioning and wicked suggestions. Just a bedroom like any other.

Except his eyes are immediately drawn to the bed where delicate lingerie is laid out next to a shimmering satin robe.

“Get undressed, put all your clothes in this basket and then put those on. I’ll be back in a minute to do your makeup. Wait in the chair when you’re ready.”. She’s quite relaxed about it, not unkind, not demanding, just utterly confident that this is what will happen. He’s suddenly aware that these are her rules, this is her game and he’s agreed to play it.

When she returns he’s sitting in the chair, just calming down after the wave of nerves that had crashed over him as he pulled on the satin robe. She smiles at him approvingly, picks up the basket containing his clothes and walks out again.

“Good girl, I’ll be right back”.

He blushes, then suddenly wonders where she has taken his possessions.

It a moment, she’s back and setting to work. She puts on some music in the background, pulls out makeup boxes and chats casually as she skillfully erases any sign of masculinity. Eyebrows blocked and replaced with fashionable arches, blush and eyeshadow, long feathery lashes. The makeup is dramatic and stylised as they had discussed. The process is soothing and not exciting as he had imagined. They discuss the exact shade of pink to use and he finds himself relaxing, pampered and comfortable.

When her work is complete, she ushers him to stand and inspects his face briefly for imperfections. Then she turns to the wardrobe and opens it to reveal racks of clothing, shoes, boxes marked ‘bows’ and ‘bracelets’ and other feminine promises. She begins to search out the costume they had agreed.

“Take your robe off, we’ll get you dressed”

The outfit goes on in layers. The heavy corset pulled into place, the short but impossibly full petticoats, bra padded with large, convincing forms and over it all the frilly, effeminate little dress she had described. She calmly presents him with each item and instructs him how to put it on. Then she guides his feet into skyscraper heels that leave him wobbling uncertainly.

For a moment he thinks it’s done, but then she goes back to the wardrobe and pulls out accessory after accessory. A necklace, clip on earrings, bracelets, bows, rings, more and more… each placed and carefully adjusted to complete the picture. He’s dripping with decoration, aware that each item is another commitment to looking pretty.

Finally, she brings out a large box. It reveals a mass of immaculately styled pink hair. He sits obediently to allow her to put it in place, like a princess being crowned. The wig is both outrageously over the top and carefully convincing. Big pink waves erupt from his head and cascade over his shoulders. She carefully adjusts the hairline so it looks like this really is his hair, styled into ridiculous femininity.

At last, it really is all done. She selects one last outsized bow and places it delicately on his head.

“Perfect! What a pretty little thing! Let’s get those photos!”, she’s delighted and so is he, though she won’t let him see a mirror to see the effect. He basks in her approval and smiles, relieved that she’s pleased with her work. As he teeters after her to the next room, each step brings new sensations of femininity and the nerves return as he feels overwhelmingly transformed.

The next room is set up as a light and airy studio, a large space with areas sectioned off for different settings. One corner has dark, rococo wallpaper; another has the air of a 1950’s domestic set. She ushers him in front of a white background and picks up the camera waiting nearby. It seems completely natural to pose for her, to follow her instructions and pout and preen for the camera. She compliments him, teases him to make him laugh, takes a short video and passes him various props. He’s in a daze, hardly blushing when she calls him a good girl, obediently taking up each pose, even when she begins asking for more.

She passes him a new prop – a thick pink dildo. For a moment he freezes and she looks up from the camera.

“It’s ok, just give it a little kiss and we’ll stop there, alright?”, she smiles reassuringly. He cautiously kisses the tip and the camera clicks one last time. “Good girl”

“Now, you remember what we discussed?” she asks. He nods nervously. She leads him to a side room and his heart hammers as he sees what is laid out for him. He’s suddenly sharply aware that she has led him step by step to this point without a single sharp word or harsh command. It doesn’t seem possible to stop though, and he steps in.

The room is medical white, with a forbidding white examination chair in the centre. She gestures to it and he finds himself carefully climbing into it. She’s still smiling and casual as she helps him raise each leg wide apart and straps them into the rests. His wrists are strapped down with identical white leather restraints. She pulls a heavy collar around his neck and attaches it to the chair so he is immobile, staring at the ceiling. Then she places high-tech glasses over his eyes, that fill his vision with coloured lights that dance with the sounds in the room. Finally, a pair of ear plugs are put in place and he is cut off from his surroundings.

After a moment, a calm, soothing, feminine voice fills his head.

“This audio is designed to hypnotise you, to train you to act like a horny little bimbo when you hear the trigger phrase. You will be helplessly obedient, a giggling plaything. It’s fun to be a vacuous attention whore. Until you hear the release phrase, these will be your thoughts and you will crave to be the prettiest, pinkest, bestest little bimbo you can be. Let your subconscious mind listen to my voice as you take a deep breath in and start to relax..”

The voice continues, warmly trickling into his ears as the coloured lights dance in his vision. It guides him to listen and relax into a trance. It talks about mannerisms and obedience and how horny it is to be so empty headed. It tells him to repeat the trigger phrase out loud and he automatically obeys, feeling warm and aroused with each repetition. It describes just how he must behave, how difficult it will be to fight it, how much he wants to be the girl of his fantasies.

As he lies there, he’s dimly aware of movement around him. Then she’s standing between his spread legs, pulling his panties to one side. A well lubricated hand wraps around his erection. It barely stops him repeating the trigger phrase as the audio instructs him. Then something is slid over his cock. A moment later it begins rhythmically sucking at him. She moves away, but the milking machine continues, pulling at him steadily, each pulse making him harder.

The audio too is telling him how aroused he is, how much being a bimbo turns him on, how much he needs to cum. The machine tugs at him and the voice tells him what a good girl he is. It reaches a crescendo and he cums noisily, all the pent up emotions of his experience crashing into spasms and gasps. At last he is exhausted, lying helplessly immobile in the chair. For a moment, he catches his breath, letting reality flood back in..

Then the voice starts again.

“This audio is designed to hypnotise you, to train you to..”, the voice repeats from the beginning.

He’s momentarily shocked by the trick she’s played on him. Then he becomes aware that the milking machine is still sucking at his limp cock. The colours fill his vision and this time he sinks into trance faster, deeper.

The second orgasm comes slower, and he is more aware of the length of the audio, how lovingly it guides him first into trance and then into obedience. How it repeats his own fantasies back to him, turns them into actions he must follow and adds twists of its own. It becomes hard to keep track of time and when it repeats again, and again he accepts and obeys, cums and calls out his own trigger.

Then suddenly she’s back, disconnecting him and pulling his panties back into place. She pulls out the ear plugs and undoes each strap in turn before helping him to his unsteady feet. He stretches and tries to shake himself back to wakefulness, dimly aware of how feminine the noises he is making sound. Finally she takes off the glasses and he blinks himself back into the room. And gasps.

Now she looks the way he had imagined. He’s not sure how long he was strapped to the chair, but she has transformed herself as expertly as she transformed him. Wicked, slightly gothic makeup. Hair styled into glamorous curls. An outfit he had once described, half joking, thinking she would never wear something like that, not for him. Stockings on show and towering heels. Everything perfect.

She’s far from the severe dominatrix. Instead she’s effortlessly sexual, playful. A teasing smile and eyes that are looking so deep into his own. She steps back to check he can stand on his own, and he drinks in her power and confidence.

“Good girl, come on”. She turns and leads him to a new room. Where she takes elegant, feline strides, he finds himself daintily putting one foot neatly in front of the other, swaying his hips and swinging his splayed hands to ruffle up his petticoats. In his head he recalls the voice telling him this is how bimbos should walk.

This time there are the dark trappings of fetish and deviance. Restraints hang from frames and lie on a heavily padded bench. Paddles and whips form neat rows on one wall. She takes a power pose amongst the toys and implements, waiting for him to teeter in to the room and stand nervously before her.

“Do you know, right now I want two completely different things!”, she smiles at him.

“I want a good… hard… fuck. That would be your fantasy, wouldn’t it? Fucking me?”, she pauses and he nods, wide eyed and speechless., “Yes, a good, no holds barred, filthy fuck”.

“But you know what? I also want to order around a dumb little bimbo. I want her to do dirty things for me just because I say so. I want a helpless little fuck toy to torment. Can you imagine?!”, she giggles happily at the thought, not caring about his reaction.

“And, ” she adds, ” I’m going to let you make the choice. We can fuck like animals, or you can be my obedient little bimbo”.

“So here’s the deal. If you can show me you’re a man, I’ll unlock your dress and shoes – yes, they are locked in place – I’ll give you back your normal clothes and we can fuck any way you like. If you’d rather be a bimbo, you agree to do whatever I say until I get bored and send you away. Just to be clear, all the depraved things you told me about when we discussed this – you’ll be doing them, and you’ll do them with a smile and a giggle. You’ll beg me to do them. Understood?”

He nods in terror.

“I know you’re horny as hell. Don’t you just want to fuck and suck and cum and cum? Well, get yourself hard for me and just say ‘I want to fuck you’. Then you can be a real man again. Go on, play with yourself. You can do it!”, she pouts and teases. Obediently he finds himself reaching into his sticky panties and tugging at his cock.

“But if you can’t get hard. If you’d rather be a bimbo, then just say ‘I’m a bimbo, Mistress’. But understand that this means you really, really want to be a bimbo. It means you absolutely accept that you’re my dumb little slut. You agree to obey me without question. OK? I might choose to spank you, or I might send you to the shops dressed like that. Whatever I choose. There’s no going back.”

He’s pulling at his limp cock desperately, but the milking machine has done it’s work. He’s so horny, so aroused, so desperate to be hard again, but he can get no reaction. He aches and he find himself moaning little girlish gasps of frustration. The machine has sucked him dry.

Then he slowly becomes aware that she’s giggling at him, laughing as he pathetically tugs and moans. She points behind him and he turns to face a wall to wall mirror. For the first time he sees the head to toe transformation. The pink hair, girlish makeup and big, round boobs. The ridiculous frilly dress and pretty pink heels. Everything in place to give just one impression. In the mirror an over-sexed bimbo helplessly rubs at her panties and stares back with wide, heavily made up eyes.

She stands next to him, as confident as he is weak. She’s taller than him, more poised, strong and sexual. In one hand she holds the dildo he had been scared to touch. At just the sight of it he finds himself dribbling. In the other hand she holds a thick butt plug. She smiles, “Sorry, I don’t play fair.” and leans close to whisper his trigger phrase softly in his ear.

The words spill from his mouth in a girlish squeak, “I’m a bimbo, Mistress!”

“Good girl, let’s see what we can do with you.”

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