FREE READ: Little Red Riding Hood, A Cross-Dressing Fairy Tale

No idea where this came from, but there was almost nothing to do at work today, so I wrote it. 1658 words

Warnings: I’m not giving you any, because fairy tales never have warnings. Read it at your own risk.

“Red, take this basket to your grandmother and hurry it up. Darkness falls early these days.”

Being a polite young man, I accepted the basket. “What’s in here? It’s heavy.”

“A freshly baked loaf of bread and some greens from the root cellar.”

No wonder the basket was heavy. Mom was not noted for her baking skills. Last winter, I chipped a tooth on a slice. Good thing it was a back tooth; my smile was still pretty. “Can I borrow your cloak? It’s cold today.”

She heaved a long-suffering sigh. “What’s wrong with your thick wool jacket? You look so good in green, too.”

I did not look good in green. I looked like a spangled Christmas tree because of my long red hair. I loved my hair. It was a wonderful color that flattered my perfect white skin. A lot of village girls had made doe eyes at me over that hair. It wasn’t their fault that I had no interest in them. The one I wanted was Kal, the woodsman, but he was courting a silly hen named Gwen. I suspected he was in love with her breasts, which often overflowed her bodice in a way that attracted me not at all, but had every other young man in the village trotting after her like slavering puppies.

“Take it then, and stay the night. Don’t come home through the woods in the dark. An enchanted talking wolf has been killing in the district.”

“Wolves, shmolves,” I said under my breath, settling the bright red cloak around my shoulders. Strangely enough, the color did not clash with my hair but only served to emphasize it’s glossy beauty. I was not overly concerned; there was always some enchanted something or other roaming the countryside, bothering the peasants.

Basket swinging from one hand, the cloak swirling around my knees, I set off on the path that led through the woods. It was already late in the day, but I stopped, as usual, at a hollow tree a few yards off the path halfway to Granny’s house.  Inside it were my treasures: a girl’s fluffy, scoop-necked white blouse, a hand-stitched piece of material shaped to hold my “breasts,” a long flowing skirt of fine material, stockings and underwear, shoes, and bits of worthless jewelry. I dared leave none of these things at home, because my mother would find them during one of her cleaning frenzies and I would be discovered.

Granny knew all about my desire to dress in girl’s things—some of them had been acquired with her help—and I always changed before reaching her small place in the forest and changed again when I went home. While we visited, she would brush my hair while we gossiped about the village ladies. Granny was a marvel: “live and let live” was not just a saying to her. It didn’t bother her that I wanted to live with another man, nor that I liked the feeling of women’s panties rubbing against my genitals.

I was seven years old when she caught me in her bedroom trying on her stockings. She stopped short on the threshold and slowly raised an eyebrow. “What are you doing, Red?”

“Playing dress up,” I said, cheeks flushed with embarrassment.

She hesitated only a moment before crossing to my side. “I think this necklace would look nice with that.” She scooped it off the hook from which it hung and handed it to me before bending down to whisper in my ear, “I suggest you not do this at home, sweetie. Your mother wouldn’t understand.”

I nodded, relieved. Even at that age, I knew how things were.

Once I had changed into my dress up clothing (for that was how I thought of it still), I continued on my way to Granny’s cozy cottage. A cold wind had come up, and it blew through the red and gold leaves, pulling them loose so they rained down around me. If that kept up, they would soon all be on the ground.  Drawing up the hood of the cloak, I moved faster, already envisioning sitting before Granny’s warm fire while we drank tea and talked.

As I hurried along the well-known path, the silk and lace underwear I wore beneath my long skirt rubbed against my penis deliciously, arousing me. Often, I would have to stop and masturbate, the desire grown so strong I could not resist, but today I was chilled and wanted only to get in out of the cold.

A welcoming plume of smoke curled upward out of Granny’s chimney, and I smiled and ran to the door, rapping on it sharply.

“Come in!”

I lifted the latch and slipped inside, shutting the door firmly behind me. Shivering, I looked around. Granny was in her rocker by the fireplace, a shawl draped around her shoulders, wire-framed glasses resting on her nose…which, I suddenly noticed, was rather large. And hairy.

Grasping the basket nervously in both hands, I said, “You are not my granny.”

“How do you know?” Yellow eyes peered at me through the glasses.

“Last time I checked, she didn’t own a fur coat.”

“You’re quite observant, aren’t you?” The luminous eyes swept over me. “It seems we are both masquerading today.”

“I don’t know what you mean,” I said huffily.

“Lift your skirt, let me get a look at you.”


A fierce growl echoed through the cheery, fire-lit room. “Do it, or I’ll eat you right now.”

Tears sprang into my eyes. “You ate my grandmother?”

“Very tasty she was, too, for an old woman.” A large pink tongue slid out of a mouthful of gleaming teeth and licked around dark lips. “But I’m not so full that I couldn’t force you down. Lift it.”

Shaking, I put down my basket and raised the skirt to my knees.

“Nice legs,” the creature commented, sucking its tongue back into its mouth. “Higher.”

I did as I was told, feeling a cool eddy of air circle my stocking-covered legs.

“What’s this? A prick instead of a pussy?” The creature laughed. “You’re no girl. Why do you dress like one?”

I dropped the skirt and picked up my basket, holding it before me as if it might offer protection. “Never mind that. You are the enchanted wolf everyone is talking about, and you killed my sweet granny.”

Reaching into the basket, I pulled out a hatchet and, taking one long step forward, swung it across the creature’s neck. It cut cleanly, and the head flew off in an arc and landed on the planked floor with a thud, where it rolled two feet and stopped. The bright yellow eyes blinked and dimmed as a long pink tongue fell out of its mouth.

The cottage door flew open and Kal strode in, axe in hand. In one sweeping glance, he took in the bloody scene before resting on me, standing by the fire, hatchet still in hand. His face expressed surprise.

“…Red? Is that you?”

Shit. I’d forgotten I was wearing my other clothes. Still in shock from my granny’s gory end and having killed the wolf that ended her life, I straightened defiantly. “It is, and I’ll take no lip from you, Kal. I’m having a bad day.”

“I was tracking a wolf and here I am…too late, I see. Your grandmother is dead?”

“The wolf ate her.”

His eyes lingered on the cleavage I had created by stuffing shaped wool down my front.  “I…I…don’t know what to say.”

Shrugging, I reached out, grasped the remains of the wolf’s corpse, and dragged it out of the rocker, letting it fall to the floor. Sitting where the wolf had lately been, I said, “I could use a drink. Granny keeps brandy in the cupboard next to the sink.”

Kal  could take a hint. He fetched the bottle and two mugs and returned, filling them both before handing me one. We drank in silence, he poured again, and again we drank. The fire crackled as a log fell in the grate, sending up a shower of sparks. I had never felt more tired or alone in my life.

Pulling up a stool, Kal sat at my feet, laying the axe on the floor beside him. “What are you then, man or woman?”

Head swimming from the liquor, I slowly smiled at him. “What would you have me be?”

Blinking, he considered that. “You’re a pretty girl…I’ve always wanted to touch your hair.”

“Do it then.”

He reached up and trailed his fingers through my long locks. “Feels like silk.”

I pulled my skirt up and spread my legs. “Speaking of silk, I’m wearing it…”

His hand slid up one stocking-encased leg, gliding lightly over curves and angles until he dipped into the shadows under my skirt. His fingers slid across the silk underwear, making a whispery sound. My penis filled and lifted. I noticed a distinct bulge in Kal’s pants.

“What about Gwen?” I asked as he pressed his palm against my hardness.

“She’s a nitwit, but Father said it was time to take a wife.” He grinned, fingering me through lace. “Seems to me I could have everything I want if we were to get together.”

Heat poured through me. He wanted me? Could life really be so wonderful?  My granny had been taken from me, but in her place, I’d been given this fine man.

“After I tell Mother what happened and the rituals are observed, I will move into this cottage and live as I wish.” I leaned over and stroked his rough cheek. “Would you like to stay here with me?”

“I will,” he declared, “if you promise always to wear silk and long dresses and never cut your beautiful hair.”

And so it came to be, and they both lived happily ever after, being exactly who they wanted to be.

The End

About Fenraven

Fenraven happily lives in south Florida, where it is really hot most of the year. Find him on Twitter and Facebook by searching on 'fenraven'.
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