The Beginning

Every story has a beginning. Mine started years ago, when I was fifteen.

I remember that day vividly — it was the day after Eid. The house was unusually quiet. Everyone had gone to my uncle’s place for the post-Eid gathering, leaving me behind to prepare for my Maths exam the next day. After forcing myself through a few pages, my eyes wandered.

In my little sister’s room, her favourite salwar kameez lay folded on the bed — a soft, glowing pink one, covered in delicate stone work and intricate embroidery. The first time she’d shown it to me, I’d felt something stir inside me, an instant, quiet longing I didn’t understand.

With the house empty, the temptation was too strong.

I locked the door, undressed quickly, and slipped into it.

The fabric felt cool and light against my skin. The dupatta draped over my shoulder like it belonged there. When I stepped in front of the mirror, I froze.

I wasn’t looking at a boy wearing a girl’s dress.  

I was looking at someone beautiful.

“I’m… so beautiful,” I whispered to my reflection, half in disbelief, half in wonder.

That single moment cracked something open inside me. From then on, I lived for the stolen hours when I could be alone — slipping into my sister’s clothes, sometimes her bangles, sometimes her earrings, always careful to put everything back exactly as I found it. Each time, I felt more like the girl I saw in the mirror, and less like the boy everyone expected me to be.

It was my secret. My safest, most dangerous secret.  

No one could ever know — not my best friend, not my cousins, certainly not my deeply orthodox family. The shame it would bring them… I couldn’t bear to imagine it.

So I buried the longing and threw myself into studies.  

If I could just get out — really get out — maybe I could finally breathe. Maybe I could finally become the person I kept seeing in the mirror.

Years of relentless effort paid off.  

I earned a seat at a university in Europe.

Freedom, I thought.  

Real freedom at last.

But freedom wasn’t the fairy tale I’d imagined.

With the scholarship money and a tight budget, living alone wasn’t possible. I ended up sharing an apartment with three other students. Back to hiding. Back to caution.  

Still, weekends offered small windows of possibility. When my roommates went out, I would lock the door, open my secret suitcase, and become her again — even if only for a few precious hours.

Then came social media. Dating apps.  

The virtual world felt safer. I could be myself without risking everything.

There were matches, conversations, flirting… moments of being desired. I played the part of the teasing, virtual “sissy” for some — and strangely, I enjoyed it. But one person stood out.

He was a Desi guy, older, married, two kids, worked in a bank. His messages were calm, patient, never pushy. We talked for months. He made me laugh. He made me feel seen.

One day he sent a simple question:

“Are you okay with meeting sometime?”

My heart stopped.  

I disappeared from the app for a full day.

The next evening, I gathered my courage and asked why he wanted to meet.

He replied he had a free weekend and, after months of talking, just wanted to see me in person.

I said yes — even though every nerve in my body was screaming with anxiety.

We met at a quiet café.  

He was everything he’d promised: gentle, respectful, attentive. He listened. He smiled at the right moments. He complimented me softly, in ways that made my cheeks burn.

I left the café floating.

Over the following weeks, we grew closer.  

He knew I was a virgin. He knew I identified as a sissy. One night he said something that still echoes in my head:

“I’d be the luckiest man alive if you let me be the one to take your cherry.”

My heart raced.  

No one had ever spoken to me with such tender desire.

In that moment, he felt perfect.  

Safe.  

Right.

So I said yes.

And just like that…  

the next chapter began.

The date was finally set.  

Ten days of spiraling anxiety followed.  

I read everything the internet had to offer — guides, forums, horror stories, success stories — and the more I read, the tighter the knot in my stomach became.

Then D-day arrived.

I shaved carefully, showered twice, perfumed myself like it was a ritual. When I stepped out of the metro station and saw him waiting, my legs felt like jelly. He smiled that calm, steady Daddy smile and led me straight to the nearby hotel. No awkward small talk in the lobby. We checked in quickly, silently, like we both understood the gravity of what was about to happen.

The door clicked shut.  

And I froze.

I stood in the middle of the room, clutching my small bag, heart hammering so loud I was sure he could hear it.

“Farzin,” he said gently, voice low and warm, “come sit next to me.”

I obeyed, perching on the edge of the bed like a frightened bird.

He looked at me for a long moment.  

“Oh my God… you are so beautiful.”

“Thank you,” I whispered, barely audible.

He noticed the tremble in my hands.  

“Don’t be nervous, baby. I’m not going to bite you, and I’ll never do anything you don’t want. But it’ll be so much better for both of us if you can talk to me. Can you do that for me, Farzin?”

I nodded quickly.

He leaned in and pressed the softest kiss to my cheek.  

“Good girl.”

The words landed like electricity.  

No one had ever called me that in real life. My face burned; I could feel the heat spreading down my neck.

“You know,” he murmured, smiling, “you look absolutely stunning when you blush.”

I blushed harder.

“We should get comfortable,” he said. “Do you want to change?”

“I… didn’t bring anything extra.”

He reached into his bag with a small, knowing smile.  

“I brought something for you.”

He handed me a simple red babydoll — soft cotton, nothing extravagant, just short, sweet, and feminine. My fingers shook as I took it.

I slipped into the bathroom, changed quickly, and looked at myself in the mirror. The hem barely reached mid-thigh. I felt exposed. I felt… right.

When I stepped back out, he was already down to his boxers.  

Forty-four years old, salt-and-pepper hair, neatly trimmed beard, broad shoulders — he looked every inch the Daddy I’d fantasized about. Calm. Commanding. Safe.

He patted the bed beside him.  

I sat.

He cupped my face gently with both hands, turned me toward him, and kissed me — slow, deep, romantic. His breath was clean, minty. The kiss melted something inside me. My nerves unraveled. A warm, tingling heat started spreading low in my belly. I could feel him hardening against my thigh.

He pushed me gently onto my back.  

Then he was everywhere — kissing my neck, my collarbone, my shoulders. When he tugged the straps of the babydoll down and closed his mouth over one sensitive nipple, I arched off the bed with a loud, helpless

“Aaaahhh…”

“Do you like that, Farzin?”

“Yes… Daddy.”

The word slipped out naturally this time.  

His eyes darkened. He growled low in his throat and became hungrier, more possessive, worshipping every inch of my trembling sissy body.

By the time he was done teasing me, the bottom of the babydoll was soaked with my own precum.

He stood, slid his boxers down.  

His cock sprang free — thick, heavy, fully erect. I didn’t know the exact size, but it looked massive. Intimidating.

I expected him to guide my head down.  

Instead, he turned me over onto my stomach.

“Lift your bum for me, baby.”

My heart thundered.  

This is it. I’m finally going to become a woman.

He rolled on a condom, coated everything generously with lube. His index finger pressed in first — slow, careful. Even that felt impossibly tight.

“Fuck… you’re so tight, sweetheart. Try to relax for me.”

I tried. I really tried.

He worked me open patiently, one finger, then more, until I was whimpering and rocking back just a little.

Then I felt the blunt head of his cock at my entrance.

“Deep breaths, Farzin. Relax.”

“Yes, Daddy… just go slow, please.”

“I will, baby. I promise.”

He pushed.  

The tip slipped inside. I gasped, fingers clutching the sheets.

“I’m going to go a little deeper now.”

He pressed forward again.  

Pain flared sharp and sudden. I whimpered.

“Daddy— stop, it hurts—”

He froze immediately.  

Tried again, slower.  

I tensed harder.

“I’m sorry, baby,” he murmured. “You’re scared, that’s why it’s fighting. Just breathe… I’ve got you.”

Then he pushed in one steady motion — all the way.

White-hot pain ripped through me.  

I cried out, lurched forward, tears spilling instantly.

He pulled out right away.  

“Shit— sorry, sorry, I’m so sorry…”

He checked me frantically.  

“No blood. You’re okay, Farzin. Your cherry’s popped. It’s going to hurt for a bit, but it’ll ease. We can stop here, rest, cuddle… whatever you want.”

“I’m sorry, Daddy,” I sobbed quietly.

“Don’t be.” He kissed my temple. “I’m the lucky one who got to be your first. That’s enough for me.”

I sniffled, then looked up at him through wet lashes.  

“Daddy… can I suck you instead?”

His smile was soft, relieved.  

“Of course, baby.”

He sat on the edge of the bed.  

I knelt between his thighs like I’d practiced in my head a thousand times.

I kissed the tip first.  

It jumped at the contact. I giggled — a silly, excited schoolgirl giggle.

Then I took him into my mouth, remembering every video I’d ever watched.  

He groaned low when I swirled my tongue. That sound made me bold. I looked up into his eyes while I sucked, hollowing my cheeks, trying to take more.

The gag reflex hit hard.  

I coughed, pulled off, stroked him with both hands while I caught my breath, then went back to worshipping the head and upper half, massaging the rest with spit-slick fingers.

It didn’t take long.  

His thighs tensed, he moaned deep, and thick ropes of cum painted my face and lips.  

I swallowed what I could, the rest dripped down my chin.

“Did you enjoy that, Daddy?”

“God, yes, Farzin.” He brushed my hair back. “You?”

“I did… so much.”

We cleaned up slowly, tenderly.  

Then we hugged, skin to skin.  

And somehow he was hard again.

I blew him twice more — once swallowing everything, once letting him finish across my cheeks and lips while he whispered how perfect I was.

When we finally parted, I rode the tube home in a daze.  

The day hadn’t gone like the fantasy versions in my head. It had been messy, painful, imperfect.  

And still… unforgettable.

My cherry was popped.  

I laughed out loud at the absurdity of it, alone in the carriage.

The train emerged from the tunnel.  

Signal returned.

My phone buzzed.

Daddy: Don’t worry too much about what didn’t go perfectly. I loved every second of our time together. Hoping to see you again soon — when your pretty little ass has had time to heal. This time I want you to come a little more… trained.

I typed back instantly, pulse racing again.

Me: What kind of training? 😳

Daddy: I’ll tell you tomorrow, baby girl.

Excitement and fear twisted together in my chest.  

Whatever it was… I already knew I’d say yes.