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She Said They Were Just Supplements. Now I’m Her Maid.

Crossdressing Story

By Lena JhonsonPublished 8 months ago 12 min read

There was nothing dramatic about the beginning.

No sudden realization. No big announcement. No tears or speeches or breakdowns. Just a quiet evening, and the familiar sound of Emily in the kitchen—humming the same old tune she always did when she was cooking something warm. ( Crossdressing Story)

I was sitting on the couch, scrolling through news I wasn’t really reading, wrapped in a throw blanket that smelled like her perfume. Outside, the sky was turning purple.

She came in, holding a glass of water in one hand and two little pills in the other.

“Here,” she said softly, like it was nothing. “Last ones.”

I didn’t ask what they were. I didn’t need to. I’d been taking them for weeks. Just like she said. “Something to help take the edge off,” she’d told me the first time. “You’ve been so wound up lately.”

I’d agreed without much thought. Life had been noisy. Work, stress, expectations. I was tired of feeling like I had to carry something all the time. So, I took the pills.

I opened my mouth. She dropped them in. I took the glass and swallowed.

She kissed my forehead.

“That’s it,” she said, brushing her fingers through my hair. “You’ve been doing great.”

I smiled, a little unsure, but still smiling.

She sat down beside me, curled up like she always did—legs folded under, body leaning into mine. Her head on my shoulder, her breath slow and steady.

We didn’t talk for a while. The quiet between us wasn’t awkward—it was lived-in. Familiar.

But something in me had been stirring. For days now. Maybe longer.

It wasn’t anything loud or specific. Just... a feeling. Like the edge of something had softened. Like I was fading a little from the sharp version of myself I’d spent years trying to protect. And somehow, that didn’t scare me.

I noticed it in little things. How I’d stopped rushing through the mornings. How my skin didn’t feel as rough when I ran my hands through the shower. How shirts I used to love suddenly felt wrong on my shoulders.

And the strangest part? I didn’t mind.

I felt calm. Not empty—just calm. Like I was stepping out of a too-tight suit I'd been wearing for years without realizing it.

Emily noticed too, of course. She didn’t say it out loud, not yet. But she looked at me differently. Her eyes lingered in quiet moments. She smiled a little more when I laughed.

I think we both knew something was shifting.

But neither of us named it. Not yet.

That night, we watched a movie we didn’t finish. She fell asleep with her head on my chest. I lay there, staring at the ceiling, my fingers lightly tracing patterns across her shoulder.

Something was changing.

I didn’t understand it.

But for the first time in a long time... I didn’t feel like running from it. It started with a glance.

One of those lazy, half-lit evenings where everything feels quiet and suspended. Emily and I were in bed, the soft hum of the fan mixing with the distant sound of a neighbor’s dog barking down the block.

We weren’t doing anything special—just lying there, side by side, legs tangled under the sheets. My head on her chest, her hand in my hair. It was one of those moments where the world felt small and safe.

And then I said it.

“Hey,” I murmured.

She hummed a response.

“How long has it been?”

She shifted slightly. “Since what?”

I hesitated, suddenly unsure if I wanted to finish the sentence.

“You know… since we’ve been… intimate.”

There was a small pause. Not uncomfortable. Just thoughtful.

She ran her fingers down the back of my neck, slow and steady.

“You haven’t really seemed in the mood,” she said gently.

“That’s the thing,” I replied, “I kind of do feel it. The need’s there, it’s just… not the same.”

Her hand stopped for a second. Then she kissed the top of my head.

“Well… it’s probably the hormones,” she said quietly, like she was testing the waters.

I lifted my head. “Hormones?”

Her eyes met mine, warm but cautious.

“You’ve been taking them for almost a month now.”

“I thought those were just… supplements. You said the first bottle was nothing serious.”

She nodded slowly. “Yeah, the first one was. But the next bottle wasn’t just vitamins.”

I sat up slightly, blinking at her.

“I thought you knew,” she said. “You didn’t notice the label change?”

“I don’t even remember finishing the first bottle,” I said, my voice catching slightly.

She looked genuinely guilty. “I should’ve told you. I honestly thought you were on board. You never questioned it.”

I didn’t yell. I didn’t panic.

I just sat there, taking it in.

Part of me felt like I should be upset. Like I should have been angry, or betrayed. But I wasn’t. Instead, there was this strange… stillness.

Because the truth was, deep down, a part of me already knew something was different. And not just physically.

Emotionally, mentally, the edges of who I was had been softening for a while.

And even stranger?

I didn’t hate it.

Emily touched my hand. “They’ll wear off. Your body will go back to normal if you stop now.”

“Will it?” I asked, quieter than I expected.

She looked at me with that familiar gentleness. “Probably. But I don’t think you want to stop, do you?”

I looked at her, then down at our hands, fingers loosely woven together.

And I didn’t answer.

Because the truth was still sinking in.

Maybe I didn’t want to go back.

Maybe I wanted to see who I was becoming.

The days that followed were quieter than usual.

Not in a bad way—just... softer. Like the volume of the world had been dialed down a little. I started noticing things I hadn’t paid attention to before. The way sunlight moved across the bedroom wall in the morning. How warm towels felt fresh out of the dryer. How I looked in the mirror when no one was around.

That last one stayed with me.

At first, it was just a passing glance. I’d be brushing my teeth or running a comb through my hair, and I’d catch something—something in the way my jaw looked, or how my skin seemed smoother than before. My features weren’t changing dramatically. But they didn’t feel as sharp. As heavy.

I lingered longer each time I stood at the mirror. Not out of vanity—but curiosity.

I started to wonder who was looking back at me.

One afternoon, while folding laundry, I held up one of my old T-shirts. It used to be my favorite—soft, faded, worn in all the right places. But now, it felt... big. Boxy. Like it belonged to someone else.

I slid it over my head anyway and stared at myself in the mirror.

It just didn’t feel right anymore.

Emily walked by the doorway, then stepped back and looked at me, smiling a little.

“You okay?”

I nodded. “This shirt feels weird.”

She leaned against the doorframe, tilting her head. “You’ve changed. A little.”

I raised an eyebrow. “How so?”

She walked over, her hands warm against my sides as she adjusted the shirt slightly.

“You’re softer,” she said, not just meaning my body. “There’s this quiet around you lately. It suits you.”

I didn’t respond, but I didn’t disagree.

That night, while we were curled up on the couch, she whispered something in my ear that stayed with me.

“You’re blooming.”

I turned to her, surprised. “What does that even mean?”

She smiled. “It means you’re growing into something. I don’t know what exactly… but it’s beautiful to watch.”

I looked away, heart fluttering in a way I couldn’t explain.

For the first time, I started wondering if this wasn’t just about taking pills. Or trying something new. Maybe this wasn’t a phase or an experiment or a game.

Maybe this was me becoming more me.

I didn’t have the words yet. I barely had the thoughts. But that night, I took an old tank top Emily had stopped wearing and tried it on in secret when she was asleep.

It was nothing dramatic.

Just a moment. A little rush. A quiet kind of comfort.

But when I looked in the mirror that time…

I didn’t feel like I was pretending.

I felt like I was remembering something I’d forgotten.

It happened on a Tuesday.

That’s the part that always struck me later. Not a weekend, not a holiday, not some big dramatic moment—just an ordinary, boring Tuesday morning.

I was sitting at my desk, staring at my computer screen, and I realized I didn’t care. Not a little, not even a tiny bit. It was like the words on the screen weren’t even mine anymore. I couldn’t remember the last time they felt like they mattered.

The emails, the deadlines, the tasks—they used to feel important. Necessary. Like they were holding something together.

But that morning, I knew they weren’t.

I closed the laptop and just sat there for a while.

When Emily walked in with a mug of coffee, I looked up and said, “I think I’m done.”

She paused, blinked. “Done?”

“With work. I think I want to quit.”

She didn’t look surprised. In fact, she just set the coffee down beside me, leaned in, and kissed the top of my head.

“I think that’s a wonderful idea.”

There was no long conversation. No need for one.

Because the truth was—we both knew it had been coming.

The job was never really me. It was something I did because I was supposed to. Because that’s what men like me did. We worked, we climbed ladders, we proved things.

But lately, I didn’t feel like proving anything to anyone.

Especially not as him.

That afternoon, I typed up my resignation email. It was short and polite and honest. I hit send before I could second-guess it.

The next day, my boss called. He wasn’t angry. He actually sounded... relieved.

“You’ve got bigger things ahead of you,” he said over the phone. “I could see it on your face the last time we talked.”

We met for lunch. He gave me a hug, paid the bill, and wished me well.

No questions. No judgment.

And that’s when it hit me—sometimes the world doesn’t fall apart when you stop pretending. Sometimes it actually opens up.

On the train ride home, I stared out the window, feeling like I’d left something behind—but not in a sad way. More like shedding a skin that never quite fit.

When I walked through the front door, Emily was waiting for me.

She looked proud. Like she already knew what I’d done.

I didn’t say a word.

She reached behind her and pulled out a small box wrapped in silver paper and tied with a ribbon.

“What’s this?” I asked.

She grinned. “A gift. To celebrate.”

I took the box from her hands, sat on the edge of the couch, and started to peel the paper back.

I didn’t know it then,

but that box was the doorway to everything that would come next.

The box wasn’t heavy.

It sat in my hands like a secret—wrapped neatly, ribbon curled at the ends like Emily had spent time getting it just right. I hesitated before opening it, something in me fluttering.

I wasn’t nervous.

I was... anticipatory. Like part of me already knew this wasn’t just a gift—it was a gesture.

A question.

Inside was something cold and silver, carefully nestled in tissue paper.

At first, I didn’t understand.

Then I read the card she’d placed underneath it:

“Some things aren’t about stopping—just slowing down long enough to feel something deeper.”

She was standing by the window when I looked up. The light caught her face just right, her expression soft.

“What is it?” I asked.

She walked over and knelt in front of me, gently taking the box from my lap.

“It’s... a little symbolic,” she said, brushing a finger over the device. “It’s used to help people pause. Let go of distractions. Of pressure.”

I recognized it then. Not from personal experience, but from late-night reading and forums I used to scroll through without ever commenting. I knew what it was—a chastity device. Not extreme. Not threatening. Just simple, stainless steel. Sleek. Small.

Intimate.

“You want me to wear it?” I asked, not accusing—just... unsure.

She shook her head. “Only if you want to. I just thought it might help. With focus. With clarity.”

I looked at it again. It wasn’t scary. It was precise. Elegant, even. And strangely enough, a part of me wanted to try.

Not out of obedience. Not even out of arousal. But because it felt like another layer of surrender. And not the weak kind.

The kind that made room for something honest.

I nodded slowly. “Okay. Let’s try it.”

Her eyes lit up—not with excitement, but with understanding.

We went upstairs. She laid out a towel on the bed like she was preparing a sacred little space. The room was quiet except for the hum of the ceiling fan.

“Lie back,” she said softly, and I did.

She didn’t rush. Her touch was calm, careful, never clinical. She explained each step in that gentle, soothing voice—checking if I was okay, if I wanted to stop. I didn’t.

When she finally clicked the last piece into place, I felt... something shift.

Not pain. Not shame.

Stillness.

A kind of hum just beneath the surface. A physical symbol that something inside me had changed—and not just that day. Gradually. Quietly. Over time.

She rested her hand on my stomach and looked me in the eyes.

“How do you feel?”

I searched for the right word.

“Contained,” I whispered.

She smiled.

“That’s not a bad thing,” she said.

And for the first time,

I understood what it meant to give yourself permission

to stop performing—and just be.

I didn’t expect to sleep well that night.

But I did.

I slept like a stone, wrapped in warmth and stillness, the kind that doesn’t come from silence but from being held—fully, without judgment. Emily lay behind me, her arm draped over my waist, her breath soft against the back of my neck.

I could feel the device—cool, gentle, undeniably there. But it didn’t hurt. It didn’t poke or sting or squeeze. It simply reminded me.

That I had chosen this.

That something had changed.

In the morning, I sat on the edge of the bed in my T-shirt and loose shorts, rubbing sleep from my eyes. Emily walked in with coffee and set it down on the nightstand. She leaned against the doorframe, watching me in the kind of quiet way she did when she didn’t want to interrupt a moment but didn’t want to miss it either.

“How do you feel?” she asked.

I sipped the coffee, then shrugged. “It’s weird. But not in a bad way.”

She nodded. “It takes getting used to.”

I hesitated, then glanced down. “You still have the key?”

She smiled faintly and patted her chest. “Right here.”

Part of me felt vulnerable hearing that. But a bigger part of me… felt safe.

Like I didn’t have to figure anything out. Like someone else was holding the map for once.

The next couple of days passed in this quiet rhythm. I didn’t go anywhere. I didn’t need to. I wore softer clothes—things that used to belong to Emily, now folded neatly into my drawer without either of us ever really talking about it. Tank tops. Lounge shorts. A soft, oversized hoodie I found myself living in.

There was no pressure, no performance. Just… existing.

The device stayed on.

Not because I was afraid to ask for it off—but because something about it felt right. Like it belonged. Like I belonged, more in my skin than I had in a long time.

There were moments of frustration, sure. Flashes of heat, tension. Late at night, I’d shift under the sheets, feeling the pressure of desire and the impossibility of release.

But Emily always sensed it.

She’d pull me close, wrap her arms around me, whisper something like, “You’re doing so well,” or “Just stay with it a little longer.”

And I would.

Not because I was being controlled.

But because I was learning how to let go.

One night, as we lay there in the dark, her fingers tracing soft lines on my arm, I whispered, “What if this changes me?”

She pressed her lips to my temple.

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About the Creator

Lena Jhonson

Sissy Stories, a safe and empowering space where identity, transformation, and self-expression take center stage. My name is Lena Jhonson, and I created this platform to share heartfelt, thought-provoking, and entertaining stories.

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