Crossdressing Stories

It was just another soul-sucking Monday morning. I sat in my cubicle, eyes glazed over as the Excel sheet on my screen blurred into meaningless columns. The constant hum of office chatter, the tapping of keyboards, and the buzzing fluorescent lights all melded into one dull, suffocating fog.

Two years ago, life was different. I had a girlfriend, Lila. She had been the light in my life—until she discovered my secret.

She'd come over unannounced one weekend and found me in my room, twirling in front of the mirror in a lavender skater skirt and white stockings, soft music playing in the background. Her eyes widened in horror, then narrowed in disgust. "What the fuck, Gordon? Are you serious right now?"

I had tried to explain, but she was already taking photos—of me, of the room, of the clothes—and left with a sneer. A week later, her friends were whispering about it. Her captions online—"Guess I dated a perv in disguise"—went viral in our social circle.

I shut myself off from the world. Parties stopped. Group chats were left on read. People from work glanced at me with vague recognition—maybe they'd seen the thread? I couldn't be sure. But every time someone laughed across the room, I winced, wondering if it was about me.

I buried myself in work, rented a tiny studio, and adopted a cat. Social interactions were limited to food delivery and emails. But the urge to dress up never went away. At night, after my chores and freelance projects, I would pull out my secret suitcase: neatly folded blouses, pleated skirts, knee-high socks, and a few wigs.

I created a burner Instagram, wore a mask in all my photos, and called myself "CherryCloud." The account didn't have many followers—just a few people who left heart emojis or "cute!" comments. It was enough. Just enough.

Until one night, a DM popped up.

"Hey CherryCloud. 💖 You're absolutely adorable. Wanna be friends?"

– Scarlett_

I stared at the message. Scarlett's profile was surreal—long legs, red lips, curves that looked painted by desire itself. She posted makeup tutorials, gym selfies, sultry bedroom lighting photos. There was no way this was real.

I didn't reply for a day. Then two. Then finally, heart pounding, I typed:"Hi… thank you. Sure, we can be friends :)"

And just like that, the messages flowed. Scarlett was funny, supportive, and never pried. She asked me about my favorite outfits, complimented my poses, and sent me makeup tips. We talked about movies, food, terrible bosses. She told me her real name was still Scarlett, and she worked as a freelance model.

I didn't know if she was flirting or just friendly—but I lived for her DMs.

A month passed. Then came the message that froze me:"Hey, want to meet up? No pressure, but I'd love to see you in person."

I nearly deleted my account out of panic. But something inside me said yes. I agreed to meet on a quiet Sunday afternoon, in a park café far from my neighborhood.

That morning, I dressed carefully—white lace blouse, soft pink skirt, sheer tights, and my favorite brown bob wig. My heart thudded as I pulled on a medical mask and added sunglasses, hoping it would be enough.

Scarlett was even more beautiful in person. She wore a tight crop top and ripped jeans, hair cascading over one shoulder, makeup glowing. She greeted me with a warm hug. "You look so cute!" she said.

I squeaked out a "thank you," voice deliberately soft and raspy.

"You okay?" she tilted her head. "You sound sick."

I panicked. "Yeah, cold. Throat. Sorry."

She reached out and touched my forehead. "Hmm, don't feel feverish."

I flinched at her touch and stood up abruptly. "I—I should go. Sorry. Not feeling well."

Scarlett blinked. "Oh… okay. Let's talk later?"

I nodded and hurried off, nearly tripping over a curb. My heart didn't stop racing until I locked the door to my apartment behind me.

She messaged me that evening:"Hope you're feeling better. 🥰 You're even cuter in person."

I stared at the message for hours.

10 days later, we met again—this time at a low-key queer bar downtown. I wore a long cardigan over a tight black dress, tights again, ankle boots, and minimal makeup. Still masked.

This time, I drank too much.

As the alcohol blurred my mind, my memories of Lila's cruelty came rushing back. The laughter. The humiliation. The loneliness.

Scarlett noticed my silence. "You okay?"

I shook my head, eyes glassy.

She gently took my hand. "Come on, let's get you home."

I barely remembered the Uber ride or the elevator. Just her arm around my shoulder, the scent of her perfume, the warmth of her hand.

In my bedroom, she helped me lie down.

"I'm gonna go, okay? Get some rest."

I grabbed her wrist weakly. "Don't… go."

She paused, looking at me. "Okay."

She gently began unbuttoning my cardigan, trying to help me cool down.And that's when she saw it.My man body underneath.

Her hand froze.

My eyes shot open. My drunkenness peeled back, horror replacing it. "No—no, wait—it's not— I'm sorry—I was just—"

Scarlett looked at me. Not with disgust. But with surprise. And softness.

"Gordon… it's okay."

I blinked, stunned. "What?"

"I mean, I thought something was up. I didn't expect this exactly. But… it's okay. I like you. Not 'cause of your gender, but because you're you."

My lip trembled. "I thought you'd hate me."

"I don't," she said, voice low. "I think you're beautiful."

Hearing that, my heart lurched. Before I even realized what I was doing, I scooped Scarlett up and gently but urgently pushed her back onto the bed. My cheeks burned as I hovered over her, then suddenly froze. "I—I'm sorry…" I stammered, scrambling to sit up, my hands trembling.

Scarlett's eyes danced with warmth. In one swift, playful move, she grabbed my shoulders and flipped me so that she was on top. "Shh," she whispered, pressing a finger to my lips. "It's okay."

We stared at each other, breath mingling, the tension morphing into something electric. Scarlett leaned in, brushing her lips against mine. My embarrassment melted away, replaced by a fierce joy. Our kisses deepened, soft at first, then hungry, as we gave in to the safe thrill of being fully seen.

Clothes peeled away in a haze of whispered names and shared laughter. Every touch felt new and right, as if we were discovering each other—and ourselves—for the first time.

For the first time in years, I didn't feel like a freak. I felt desired. Cherished.

The next morning, we lay tangled in sheets, sunlight pouring through the curtains.

Scarlett was tracing lazy circles on my bare shoulder.

"So," she said with a smirk, "do I get to see more of CherryCloud's wardrobe?"

I laughed, heart full for the first time in years. "Only if you promise not to steal my skirts."

"No promises," she winked.

And somewhere deep inside, I knew—I wasn't alone anymore.

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