Feminization Starts Now

Hello everyone. I'm glad to see people are liking the stories. This is a long one. it happens over a week. Leo's power over Jenny is moving forward and it's time for it to move into her male life and get feminized.

Please leave me a comment so I know if I'm going in the right direction and if you enjoy the story.

Jenny.

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So,. it's been three months since that unforgettable night at the Boutique Hotel in Chicago. The night I finally mustered up the courage to slip into my Jenny persona and got to meet Leo. I still can't believe how perfectly everything clicked. Our first date was like a dream, and every moment since then has been nothing short of amazing.

Leo and I have been exploring the city, pushing boundaries, and diving deeper into our fantasies. Every time we're together, I feel like I'm unraveling a new layer of myself, discovering what it truly means to be Jenny. His guidance, patience, and passion have unleashed a side of me I never knew existed.

Leo's been dropping hints about taking our relationship to the next level. At first, I thought he meant intensifying our play or exploring new kinks. But no, he's got bigger plans. He wants to bring Jenny out of the shadows, to let her occupy more space in my life.

The other day we had dinner at his place and he opened the conversation. I sat across from Leo, sipping my wine.

"Jenny, I'm done with this part-time thing," Leo said, his voice firm. "I want you to go all in. Dresses, heels, lingerie -- every day."

'What makes you think I'm ready for that?' I asked.

Leo leaned forward. 'You've been craving this for years. It's time to stop hiding."

'But it's not that simple,' I countered. 'What about work? My friends?'"

Leo shrugged. 'We'll figure it out. You can't keep living two separate lives, baby girl. It's time to integrate."

'And what does that even mean, exactly?' I pressed.

Leo smiled. 'It means being Jenny, always. No more switching between personas."

'That sounds scary,' I admitted.

'Baby girl, that's been a fantasy of mine for years,' Leo said. 'Feminizing my gurl, transforming her into my perfect woman. I want to spend every moment, every dollar, making you into the goddess I know you can be.'

'What do you mean?' I asked.

Leo touched my chin. 'I want to erase every rough edge, every masculine trait. I want you smooth, silky, and radiant. Laser hair removal, for starters.'

'And then?' I asked, intrigued.

I could see the smile in his eyes hidden by his poker face."You'll wear what I want, baby girl," Leo said. "Dresses, skirts, lingerie -- all to make you look like my perfect little slut."

'I love that idea,' I said.

I could see him getting excited, he had really thought about this before. 'And professional makeup lessons.'

'That sounds amazingly fun,' I replied.

Leo leaned in. "You'll take massage lessons, my pet," Leo said. "You'll learn to ease my tension, soothe my muscles, and please me in every way. I want you skilled, obedient, and devoted to my pleasure."'

Leo's gaze roamed over me."Your body will be reshaped to please me," Leo said. "We'll hire experts. You'll be toned, curvy, and healthy, ready all the time."

"Ever thought about modeling lessons, Jenny?" Leo asked.

"No, never," I replied.

"Good. You'll learn to walk, pose, and spread your legs on command," Leo sai. "My rules, your body. You'll be my private showpiece."

"Oh, Dady, yes! I want to learn everything. Walk, pose, seduce... all for you. Your private model, your personal pornstar."

"Aaaaand hormones?" I asked.

Leo's expression turned serious. "Not yet, baby girl. First, we perfect the outside. The curves, the look, the attitude. Then, and only then, we'll consider the next level."

'You really think I can be that woman?' I asked.

Leo's smile was arrogant. "Fuck, yeah, baby girl. You're mine now. I'll mold you into perfection."

'What do I need to do?' I asked, wanting to scream on the inside, consumed by excitement and terror at the same time, but I kept my pretty face..

Leo leaned in. "You'll do exactly as I fucking say, when I fucking say it. You'll trust me completely."

I nodded.

"We'll start with small changes. Gradual transformation into my perfect toy. And when the time's right, we'll take it to the next level."

"I'm ready. When do we start"' I said.

Leo smiled and said."Come here, kneel in front of me and suck my cock while I tell you, Baby Girl"

I got up almost instantly, I walked slowly towards him, my index finger in my mouth, and foot across the other, and then I did as told. He took his cock already hardening out and I took it in my mouth, fully, slowly, but all the way to the back of my throat., then starting bobbing my head slowly, he would play with my hair, uncovering my face.

Then he said: 'Next week, baby girl. And every day, you'll have tasks to complete. Your transformation begins.'

I lifted my head and asked "What kind of tasks?" then went back up and down, all the way down

"'Starting small. Wear something of Jenny's underneath David's exterior at work. we are going to start with black sheer stay up stockings.'

"And then?"' I tried to ask with a mouth full.

Leo's eyes sparkled. "Each day, you'll receive a new task. Makeup, wardrobe changes, mannerisms...you'll report back to me every evening."

"How will we..." went down again "meet?" I asked.

Leo's smile was sly. 'We'll see each other at the end of the week. Friday evening, you'll come to my place, and we'll review your progress.'

Leo's hands went to the back of my head as I went down his ock and he kept me there without being able to breath. "Remember, baby girl, trust is key. You'll do exactly as I say, no questions asked."

I nodded. He released me.I gasped for air, taking his cock in my hand, jerking him with my mouth open and thick saliva still connected to my god

"And by the time I'm done with you, baby girl, you'll be a succulent little slut, begging for my touch, craving my cock." He slapped my face with mid strength. "You'll be my perfect, submissive, feminized plaything.'"

We had a great weekend.He played long and rough with me. Now it is Sunday and I'm supposed to go to sleep, how can i if I can't even sit down.

Leo's efforts to bring out my femininity have been tireless. He's always suggesting new things, new ways for me to express myself. And I have to admit, it's exhilarating. I feel like I'm finally living my truth, like I'm finally home.

Holy shit, I've been Jenny for days straight - a fucking record! It used to be just quick dress-up sessions, sneaking away for a few hours. But with Leo's delicious encouragement, I've been living as my true self for what feels like forever.

It's terrifying and thrilling, like I'm finally free to be me, no apologies needed. But god, the fear of losing myself, of not being able to switch back to David when real life calls! Leo keeps whispering in my ear, telling me not to worry, that he's got me. But it's hard to shake the feeling that I'm on borrowed time, that eventually, I'll have to stuff Jenny back in the closet.

Leo's been introducing me to a whole new world of pleasure. He's teaching me the art of submission, showing me what it truly means to give myself over to someone completely. Its nothing like my fantasies, it's way deeper than that.

His cock is my god, my purpose. Everything I do, I do to please him. Nothing we do together could ever be wrong or dirty because it's what Leo wants. And what my Daddy wants, My Master gets. I'm just lucky enough to be the vessel for his desires.

Oh. My. God. We've gone from subtle to scorcher! Leo, that deliciously sadistic master, has been ramping up the intensity! Rope, blindfolds, and now he's unleashing his crop, leaving me breathless and begging for more! Each stroke, each welt, I'm counting, I'm craving!

And Leo's whispers "Good little pain slut..." Oh, heaven! He's crafting me into his perfect sub, training me to surrender on command. I've never felt so alive, so free!

His control is my addiction. He knows exactly what I need, and it's terrifying how right he's been. Why wouldn't I trust him with this next step? Feminization, here I come!

I'm utterly enslaved to Leo's approval. He sees me as a sensual, submissive woman, and that's all I want to be. His toy, his plaything, his forever.

But tonight? Sleep's a no-show... again. My mind's racing and tomorrow is monday.

MONDAY

My brain's still adjusting to the idea of being David all week. As I'm ironing he's boring-ass shirt, Leo's text lights up my world: "Hey Baby Girl, make sure David's got something special under those clothes today." I can't help but smile, remembering our last mind-blowing session. When I was on all fours, ass red from his hand, he made it crystal clear: I had to wear something that screamed Jenny, even under David's dull exterior. Today's pick are Black stockings, lucky me.

I text back, trying to sound like the good little slut I am: "Morning, Daddy. David's getting ready for his job, and I've got your special surprise on. Black stockings, just like you wanted. I'm nervous as fuck, but so excited to see how this goes. Can't wait to hear from you again ;)."

Leo's simple "Good girl" makes me feel like I've won the fucking lottery.

But I'm not ready to let boring-ass David take over completely. I want Jenny to shine through. So I squeeze into skinny jeans and a tight white shirt - something to keep me connected to my true self. It's my little rebellion, my way of keeping Jenny alive in David's world.

Ordering coffee, I catch myself using my Jenny's high pitch voice and try to overcompensate with a deep "thank you" that sounds like I've got balls made of lead. Fuck, I hope no one noticed.

The morning at the office is sooo slow. I'm dying for something to break up this mind-numbing monotony. Then, just as I'm about to lose it, Leo's message pops up at noon: "Time to hit the bathroom and edge, baby girl. Picture yourself on your knees in that pink outfit from the dressing room. Imagine me about to paint that pretty face with my cum. Stop just before you cum, then get your beautiful ass back to work. Report back when you're done." Holy fucking shit, this is SO FUCKING HOT!.

Of course it doesn't take a whole second before I'm on my way to the bathroom. I'm practically sprinting, trying to look casual but feeling like everyone can see right through me.

I'm shaking like a fucking leaf as I lock myself in the stall. Taking a deep breath, I scan the area, making sure I'm alone. Then I slowly peel off David's pants. Holy shit, my legs in these black stockings are so hot. I can't help but admire myself for a second.

I close my eyes and dive into Leo's fantasy. There I am, on my knees in that pink vinyl bimbo dress. The dressing room mirror reflects every detail, the lighting perfect like we're on a porn set. Leo's standing there, looking at me like I'm the hottest thing he's ever seen.

In my mind, his glorious cock grows bigger and bigger in my mouth, pushing against the back of my throat until I'm gasping for air. Fuck, I'm getting so close. Too close. I have to stop, but it's like torture. I'm panting like I've run a marathon, reminding myself I can't finish. Not yet. Leo's orders.

I wait in the stall, willing my hard-on to go down. It feels like forever before I can put David's pants back on without looking like I'm smuggling a banana. These fuckers are way too tight now.

Finally, I feel like I can leave without everyone knowing I just nearly jizzed my pants in a bathroom stall. I splash some cold water on my face, trying to cool down and focus on the rest of this mind-numbing day. Fuck, how am I supposed to concentrate on work now?

Time to text Leo: "Mission accomplished, Daddy. Edged in the bathroom just like you said. Nearly lost it thinking about that pink dress and your incredible cock. These stockings are driving me crazy. Can't wait for more instructions. Your baby girl is always ready to please."

I hit send and wait for a response, but there's nothing. The bulge in my pants comes back quickly. Shit, time to focus on those urgent tasks.

But as I sit down at my desk, I realize I'm having trouble concentrating. My mind keeps wandering back to the bathroom stall, to the feeling of the stockings on my legs, to Leo's eyes on me, to his magnificent cock in my throat. I try to push the thoughts away, but they linger. I send Leo a text telling him of my situation.

"Hey Daddy, having trouble focusing on work. Can't stop thinking about the task and your glorious cock. Need help getting my mind back on track."

That's when he replies: "You have to realize you need to let Jenny take over. Relax your shoulders, and let her do the work." I'm so fucking turned on by this, how can I even concentrate now?

Of course, I don't say that to him. I reply "Yes, Daddy. Thank you, Daddy. I'll do just that." I take a deep breath, trying to relax my shoulders, trying to let go of David's inhibitions. I start to think about the tasks at hand, but this time, I'm thinking about them as Jenny would. It's weirdly liberating.

I'm typing away, answering emails, and crushing tasks like it's nothing. But it's not just about getting work done - it's about embracing this part of myself. I feel like I'm dancing on the edge of something, like I'm teetering between David and Jenny.

Leo's words echo in my mind: "Let Jenny take over." It's like he's whispering in my ear, urging me to let go, to be free. And I am. I'm free to be me, to be Jenny.

Fuck, I can't wait to tell Leo about this. To show him how well I've followed his instructions, how I've let Jenny take over. I hope he'll be proud of me. I hope he'll reward me.

But for now, I've got work to do. And Jenny is more than up for the task.

I'm itching to text Leo again. My clit's rock hard just thinking about telling him every detail. But Daddy said focus, so I'm trying to be his good girl. Who knew being a good girl could be such a mindfuck?

The day drags on forever. By the time I get home, I'm happy and tired, I guess it does take a toll. This week's gonna be intense. No clue what kinky little things Leo's got planned, but I bet I'll be begging for more like the cock-hungry slut I am.

I text Leo right away, let him know I'm home and how I was able to work letting Jenny flow.. His response makes me throb: "Good girl. Put on your red corset - you know, the one that makes you look like a porn version of Jessica Rabbit. Leave the stockings on, and red heels, always in heels around the house. Let Jenny take over. David stays out. "

Fuck yes, Daddy. I strip down in seconds, squeezing into that uber tight corset. It cinches my waist so tight I can barely breathe, pushing up my fake tits till they're almost popping out. I look in the mirror and holy shit. I have these red patent stilettos that are impossible to walk in, with metallic heel. Of course those are the ones I choose. - I'm a walking wet dream. This is Jenny - Leo's obedient little fuckdoll, ready for whatever he dishes out.

As I walk around, I focus on moving like the slut I am. I sway my hips like a seasoned stripper, my ass jiggling with each step. It's fucking intoxicating.

In the bathroom, I go full fem. I slather on some cherry-flavored lip gloss, making my lips look bee-stung and cock-ready. I brush out my wig, the long blonde locks falling around my shoulders like a porn star's. A dash of mascara, and Jenny's sultry eyes stare back at me from the mirror. It's still mind-blowing to see myself like this, but Leo says it's who I am. And fuck, do I want to believe him.

I'm so turned on I can barely think straight. But I won't touch. Not without Daddy's permission. That's what good girls do, and I'm determined to be the best little fuckdoll Leo's ever had.

I'm about to fix some dinner when my phone buzzes. It's Leo: "Send me a pic, slut. Show Daddy how pretty his girl looks."

My clit throbs as I pose in front of the mirror, angling my phone to capture how the corset barely lets me breathe. I look like I'm auditioning for a sleazy porno. Perfect. I hit send, then wait, barely breathing.

"Good girl," comes the reply. "Now edge yourself for 90 minutes. But remember, no cumming."

Fuck. I'm shaking as I start to touch myself, already so close. It's gonna be a long fucking night.

TUESDAY

I wake up with my clit throbbing, phone buzzing with a new message. Fuck, I'm already leaking. I stumble to the kitchen, instinctively walking on my toes like some slutty caricature of femininity.

Leo texts me: "Morning, slut. Wear a pair of tiny cheeky shorts under David's clothes and a small butt-plug to work today. I'll be thinking about your ass all day." Holy shit, yes. "Thank you, Daddy. Good morning" I reply.

First thing I do is put on the plug as I brush my teeth. It's certainly coming in easier than before Leo.

I dig through my drawer, fishing out those black cheeky shorts I impulse-bought at Target ages ago. They were on sale, way too small, but I couldn't resist. Typical CD bullshit, right? I squeeze into them, feeling them ride up my crack. They make my ass look fucking obscene.

I pull on David's suit, its a beautiful one, I've got standards, even for boy mode. But underneath? Pure Jenny. I catch a glimpse in the mirror - power suit on the outside, Leo's personal fuckdoll underneath.

My clit's already twitching, and I haven't even left the house. Fuck, I hope Leo's got more planned. I'm so ready to be his good little slut.

Exactly at noon my phone buzzes, my shorts shrink even more with the sound, WTF that's a long ass text.

"Listen up, slut. Lunchtime game. Get your ass to a bathroom stall now. Here's what you're gonna visualize:

You're walking into a packed nightclub, the center of attention. You're in a skin-tight red dress that barely covers your ass, tits pushed up, looking fake as fuck. Six-inch stilettos make your legs go on forever. Heavy makeup, bright red lips, you're a fucking vision.

Every eye is on you. Men want to fuck you, women want to tear you down. You hear them whispering, 'Look at her, thinking she's a real woman.' 'What a fake, what a slut.' 'She's just a man in a dress.'

But you keep walking, posing, enticing. You shake your ass, you swing your hips. Men shout, 'Hey, baby, show me what you've got!' 'Fuck, you're hot!' 'I want to fuck you all night!'

Women sneer, 'You'll never be a real woman.' 'You're just a pathetic man playing dress-up.' 'You're disgusting.'

You take it all in, every word, every glance. You feel the heat of their eyes on you, the weight of their judgment. But you don't stop. You keep walking, keep posing, keep enticing.

You're exposing yourself, you're putting yourself on display. You're doing it all for me, you're my little slut, my little whore. And you're going to keep walking, keep posing, until I tell you to stop.

Hold it, whore. Teeter on that edge. If you cum, there'll be consequences.

This is the only fantasy you're allowed. Don't add anything to it. My thoughts are the only ones that matter."

Fuuuuuuck! I try to cover myself, to hide the bulge in my pants. I wrap my arms around my waist, holding my suit jacket shut. It's not enough. I can still feel their gaze, like a weight on my skin. I'm so exposed, so vulnerable.

I make it to the bathroom. I lock myself in the stall,breathing heavily. I'm safe, for now.

I'm such a whore. I'm Leo's whore. And I love it. I hate it. I don't know what I am anymore. All I know is that I have to do this, for Leo, for myself. I take a deep breath, trying to calm my racing heart. I can do this. I have to

I slide the lock into place, I begin to visualize the scene Leo described. I'm in a packed nightclub, the music pulsating around me like a living thing. I'm wearing a skin-tight red dress that barely covers my ass, my tits pushed up and out, looking fake and fabulous. Six-inch stilettos make my legs look endless, and my heavy makeup and bright red lips make me look like an expensive whore.