Forced crossdressing Naruto Part 6: Pajama Night with Sakura (Patreon)

The dinner had been pure torture. But the real nightmare began after Sakura agreed to stay the night.

Tsunade had everything prepared. After dinner, she led us both to a large bedroom with two beds. On one of them lay a soft pink babydoll nightgown — short, silky, with thin straps and delicate lace.

I stared at it in horror.

“No… absolutely not,” I whispered, backing away.

Tsunade smiled. “You will wear it tonight, Naruko. Sakura is here to help you get used to it.”

Sakura looked uncomfortable but didn’t argue. She seemed torn between pity and curiosity.

Tsunade first sat me down in front of the mirror. She brushed my shoulder-length blonde hair and tied it into a neat high ponytail with a pink ribbon, making me look even more girlish. Then she helped me change into the pink babydoll. The silky fabric barely reached mid-thigh and felt far too revealing.

When I looked at myself in the mirror, I felt my stomach drop. The ponytail, the light makeup still on my face, the delicate pink nightgown… I looked like a cute girl ready for a sleepover.

“I can’t… I look ridiculous…” I muttered, my voice soft and high, pulling uselessly at the hem of the short nightgown.

Sakura sat on the edge of the bed, blushing slightly as she looked at me.

“Tsunade-sama… this is going too far,” she said quietly.

Tsunade simply chuckled. “Nonsense. Naruko needs to get comfortable being seen like this. You two are going to have a nice pajama party tonight. Talk, do each other’s hair, maybe even practice some feminine gestures.”

She left the room, locking the door behind her.

An awkward silence filled the air.

I stood there awkwardly, arms crossed over my chest, the silky babydoll brushing against my thighs. Sakura finally spoke:

“…You really hate this, don’t you?”

“Obviously!” I replied, my voice cracking. “She’s turning me into… this! I tried to run today and she still caught me. Sasuke saw me too…”

Sakura’s eyes softened. She stood up and gently adjusted the ribbon in my high ponytail.

“You look… strangely cute,” she admitted, almost embarrassed. “But I can see how much you’re suffering.”

For a moment, I felt a spark of hope.

“Sakura… please help me escape. I can’t take this anymore.”

She hesitated, biting her lip while looking at me in the pink babydoll and ponytail.

Before she could answer, Tsunade’s voice came from outside the door:

“Girls! Don’t forget to do each other’s nails before bed. Naruko needs practice with soft, feminine colors.”

Sakura sighed and looked at me with conflicted eyes.

And as I stood there in my pink nightgown, hair tied in a cute ponytail, completely vulnerable, Sakura whispered:

“...I’ll stay tonight. But I don’t know if I can stop her.”