A Forced Feminization Story: The Red Riding Hood Transformation

The Woes Begin

“Please, Robert, I need your help.” Things weren’t going well. They had been best friends forever and had shared many secrets. The rising cost of rent was making both of their part-time jobs not pay enough.

Talks of moving in together had happened before, but there was always some problem. Robert’s apartment wasn’t big enough for two people to live comfortably, and it was kind of a slum. Meanwhile, while Helene had a great deal on a two-bedroom apartment, it was exclusively for women.

Thinking that that was that, Robert had dropped the idea, but here Helene was bringing it back up. “You know we can’t both afford to break our lease. My lease is up soon, but you’re locked in for another year.”

“I don’t wanna break my lease, Robert,” Helene admitted.

“Then it is still a no-go. Your apartment only allows women.”

A Complicated Proposal

“Yeah, I’ve been thinking about that.” Previously, Helene had looked desperate for help, but now she looked embarrassed about asking for it. “I remembered that secret you shared with me. You know, the Halloween secret?”

Of course, Robert knew the Halloween secret. It was his most guarded secret. If it weren’t for getting drunk on one Halloween with Helene, he wouldn’t have ever told her. He gave a quick sideways glance at both sides of the coffee shop before leaning. “My stupid older sisters dressed me up as Little Red Riding Hood for Halloween in High School. That’s it.”

“That’s not it,” Helene whispered back, “you told me everything, remember?”

Robert took a long sip from his coffee. He wished they were having this conversation over beer instead. At least then he’d be drunk. “I liked it. I wanted to wear it more, but my parents found out and burned the costume.”

A warm smile came over Helene’s face, and she put a hand on his shoulder. It was a soft attempt at comforting him. “I know. Your parents are stuck in the mud. You had a chance for self-exploration, and they stopped you. That’s what this is now, though.”

The Offer

“What do you mean?”

Helene sighed. “You live with me. At my apartment. As a woman.”

Tightening his jaw, Robert almost spat out his coffee at her suggestion. He coughed and sputtered as he waved off some help from nearby customers. “No. No. No. Nooo. There’s no way your apartment complex won’t find out about that.”

“Of course. We don’t need to keep it a secret from them. We tell them straight up. They are super accepting of trans women nowadays.”

“I’m not trans Helene.” Robert’s gaze drifted down to his coffee cup, and he paused as he stared into the abyss of dark roast.

“How do you know? Remember the Red Riding Hood costume? The frills and the lace? The petticoat? I let you borrow my panties once to wear. I never got them back.”

Blushing, Robert came back to reality. He still had them, and he had even bought some more of his own to wear secretly. It was something fun, but it was also something secret. “I don’t know Helene.” Robert pushed his chair back and stood up. He pulled out some money and tossed some dollar bills onto the table. “I gotta go.”

“The offer is still open,” Helene called with a sigh as Robert left the coffee shop.

Thoughts and Doubts

He slumped against the window as he tried to gather his thoughts. Winter had already begun to bleed into the autumn air. He could go back to his apartment, but the offices controlled the building’s heat, and they hadn’t turned it on yet.

A walk would do well to clear his head anyway. Pulling his coat tighter, he strode off towards the mall. He’d do some laps around there while he thought.

Helene’s offer bounced around in his head. He had kind of erupted at her offer and run away from it. A large part of him was afraid, though, that he might’ve said ‘yes’ to it. It was a dumb idea. He knew Helene had longed to be a novelist. Dumb, eccentric ideas were kind of her favorite.

That was all a long-winded way of saying he wanted to, though. If she had asked again and again and talked more about that costume, he would’ve broken. But that was a dumb idea.

The thought wouldn’t leave his head even as he entered the mall. If it worked, he’d get to indulge in being feminine and save a ton of money while doing it. Not to mention leaving his rat-infested apartment. He could get a new coat. One that actually kept him warm.

With those thoughts, he wandered into the coat sections. Men’s on the left, women’s on the right. However, the women’s section stretched an extra couple of displays. He felt drawn to them. He knew he should’ve only checked out the men’s, but his thoughts kept drifting to the what-if.

What if he accepted Helene’s offer?

Temptation in the Mall

His hand ran along one of the women’s coats. It was a long red coat. Practically a dress that would come down to his knees. It had a slight flare halfway down that would give the illusion of hips even on his meager frame. A series of oversized black buttons ran down the center of the garment. These would keep it together against the harshest of winter winds.

Helene’s soothing voice chirped in his ear once more. “You could be Red Riding Hood again”. It was dumb. It was stupid.

It was exactly what he wanted.

Helene plopped down in her lazy chair. Her hands were shuffling through various bills. It would be tight, but she had made it through worse. While the bills demanded her attention, she struggled to focus on them. Her mind kept drifting to Robert at the coffee shop.

Had she pushed too hard? She was positive that there had been a want there. Ultimately, the fear had won out. She hoped that Robert would still be her friend at the end of the day.

The Unexpected Visit

Her doorbell scared the living daylights out of her. She jumped out of her seat and sent her bills sprawling. Was she expecting a visitor? No. Could it be the landlady? She was fairly certain she was caught up to this month, at least. Nonetheless, she didn’t want to keep whoever it was waiting.

She made it to the doorway quickly. Caught a sight of herself in the mirror and quickly straightened out her hair. On the other side of the door was a surprise.

Robert had come to her apartment. However, Helene wasn’t sure if that was quite right. Dressed in a long-sleeved white t-shirt with lace around the collar and a pair of skinny jeans. He had an extra few inches from the black pumps he wore. His face had make-up on it, although it wasn’t the best job.

On top of it was a gorgeous red coat. A cute flare to its hips, and the hood is done up with a fur lining. An uneasy question was on his lips as he spoke. His voice is a rough facsimile of that of a real woman’s: “Do you still need a roommate?”