Fairytail Crossdressers (Commissioned Story)

Fairy Tail Crossdressers

Wendy tenderly shuts the door behind them and moves slowly back into Erza’s view. Erza avoids looking directly at her. Erza could feel the nervous energy radiating from Wendy’s worried body language.

“Wendy….?” Erza mutters as Wendy comes to a stop in front of her. “What was it you wanted to talk about?”

Standing awkwardly on the spot, Wendy rubs her arm and swivels a single tiptoed foot from side to side.

“Not sure how to approach this,” Wendy admits, as she looks anxiously around the room. “I need your help and I’m worried you’re going to get upset with me for asking.”

Raising a single eyebrow, Erza shrugs off her comment and leans towards Wendy with a comforting smile.

“Hey…,” Erza says with a comforting soft voice. “I know you’re new around here, but you can ask me anything you want.”

Running a finger through one of her long pigtails, Wendy looks down at her feet.

“I know you’re a….,” Wendy pauses and then looks up at Ezra with a meek smile. “You’re a crossdresser, aren’t you?”

Turning bright red, Ezra instantly looks away. Her confidence stance quickly becomes nervous and uncomfortable.

“Urm…..,” Erza mutters. “I’m not a….”

“Don’t worry!” Wendy interrupts and grabs one of Erza’s shaking hands. “I’m a crossdresser too!”

Shocked, Erza stares down at the petite-looking girl holding her hand tightly.

“Sorry…..what!?” Ezra questions. “Are you really a crossdresser?”

Reluctantly letting go of Ezra’s trembling hand, Wendy takes both of her hands and places them gently on her flat chest. She looks up at Ezra’s face and gives her a small nod.

“Yeah,” she smiles. “I’m sure! I’m also really sure you’re one too. Don’t worry, your secret is safe with me.”

Dropping her head and letting out a sigh, Erza feels a sense of relief wash over her. The secret she’s been holding for years, she can finally talk about it with someone. She can finally talk about her struggles.

“H-how did you know?” Erza asks as she looks at Wendy’s beaming smile.

Still holding her hands against her flat chest, Wendy looks down at her body and huffs in frustration.

“I just knew,” Wendy comments. Then with a look of determination in her eyes, she continues. “I need your help. I want to look as stunning and as convincing as you do!”

“Wendy…..,” Ezra remarks with jubilation. “That’s such a nice thing for you to say! I really do try my best to look at feminine as I can.

With a smile on her face, Erza then looks Wendy up and down. The beautiful young girl she see’s in front of her causes Erza to pull a bewildered expression.

“I don’t get it,” Erza says confused. “I mean, you’re such a little cutie! I would have never have guessed you’re a guy. So, why is it you need my help?”

Wendy stamps her foot and puffs out her cheeks in frustration.

“That’s exactly it!” Wendy whines. “I’m 19 and you all treat me like I’m a schoolgirl. I hate it!”

Wanting to comfort her, Ezra places a hand on her shoulder. Looking deep into her eyes, Erza gives her an understanding nod.

“So you want me to help you look more your age?” Ezra asks gently.

Wiping a tear from her eye, Wendy looks up at Ezra and smirks.

“It’s not just that,” Wendy replies quietly then points directly at Erza’s curves. “I want to look sexy….just like you!”

Stunned, Erza takes a step back and goes bright red. She does her best to hide her blushing face, by looking away.

“Y-you think I’m s-sexy?” Ezra asks in discomfort.

Stepping back into Erza’s vision, Wendy gives her a sour look and taps her gently on her armor.

“Stop looking for compliments!” Wendy growls. “I’ve seen how you enjoy all the male attention. You know you make an attractive woman, that’s why I’ve come to you for help.”

Erza smirks and playfully rolls her eyes.

“Please help me!” Wendy pleas. “It was great at first when people started treating me like a girl. I loved that feeling but now I’m fed up with being treated like a little girl. Please help me become the woman I’ve always dreamt of being since I was a little boy!”

Tenderly moving a single, hand to hold up one of Wendy’s pigtails, Erza gives her a reassuring smile.

“I’m more than happy to help you,” Erza says grinning. “I’m just so happy I’m not the only one. You don’t know how difficult it was being me at first. I had no idea how to dress or act feminine.”

Allowing Erza time to examine her hair, Wendy just listens to Erza talk about struggles she is all too familiar with. Her mind wanders back to the first time she ventured out as the girl she’d eventually become today. The memories of first time she wore a dress, the first time she was called wendy, and the first time she did her hair in her favorite style.

“I think,” Ezra explains, snapping Wendy from her daydream. “We should do something different with your hair. Maybe you should try wearing your hair with bangs?”

Excited by the prospect of finally being seen as a sexy woman, Wendy bounces gently on her tiptoes. As she does, Ezra takes a small pink bow from her pocket and places it on Wendy’s head.

A moment later the room fills with a brilliant bright golden light, thats emanating all over Wendy’s hair.

“Transformation magic?” Wendy asks as she shields her eyes.

Awaiting an answer, Wendy looks up at Ezra’s smiling face and finds her sight slightly impeded by unexpected hair cascading down her face.

With both hands, she grasps at the bangs now framing her face. Then with a flick of her head, long hair dances behind her and tickles shoulders.

“H-how does it look…?” she asks nervously, as playfully flicks her hair once more.

Taking a second to look at all the angles of Wendy’s new hairstyle, Ezra smiles.

“I like it,” Ezra cheers. “You’ve instantly started looking more like a young sexy woman. Do you like how it feels?”

Shaking her head from side to side, allowing her hair to playfully tickle her bareback, Wendy happily claps her hands together.

“I love it!” she cheers. “Just being able to flick my hair, like a sassy woman, makes me feel so girly!”

With a wide eye grin, Ezra claps her hands together.

“When I was a young boy,” Ezra starts explaining. “I couldn’t wait to have hair like that. I dreamt of the day I could put my hair into a ponytail, or have it down and sexy.”

“ME TOO!” Wendy instantly replies. “I remember telling my Mom that I wanted to grow my hair out. She wouldn't let me, so I hid so many different wigs in my room. Whenever I got the chance, I’d sit in my room brushing my wigs straight. Then I’d style them! My favorite was pigtails, but I’m totally coming around to having bangs though!

“Have you…..,” Erza pauses and looks down at her full feminine chest. “Have you ever considered making your chest a bit more feminine?”

Blushing, Wendy holds her bangs away from her eyes and looks down at her petite but plain-looking body.

“I can’t say I have…,” Wendy replies. “I’ve always had a very small body. I’ve always been very feminine, with narrow shoulders, big tighs, and a skinny physique.”

Allowing her bangs to droop and cover her face, Wendy runs her hands down her dress.

“I guess when people started calling me a little cutie, I loved the attention I was getting. It made me feel like an actual girl. I guess now I’m getting older, a proper female body would have more curves….?”

Not waiting for Ezra to answer, Wendy blows the bangs from her face and pouts with a huff.

“Ok, maybe we should try a different style,” she complains. “I love the feeling of this hairdo, but the bangs are annoying me. How do girls deal with all the hair in their faces?”

Laughing, Ezra enacts her transformation once more. The room fills with the same bright, brilliant golden light as before.

Wendy’s bangs lift and merge back into her hair. Before the light starts fading, a single ponytail forms just of the side of her head. Single thin strands of hair continue to frame her face and a sweeping fringe covers her forehead.

“Yeah!” Erza cheers and brings her hands together. “The Lucy look really suits you!”

A little surprised, Wendy runs a hand through her long ponytail and gives Erza a devious look.

“The Lucy look…?” Wendy enquires. “Have you made my hair looks like hers!?”

Giving a cheeky wink, Ezra nods.

“Do you like it?” Ezra asks. “I just love giving myself her hairstyle. She’s like a role model to me. She’s so feminine and beautiful, I wish I could be more like her!”

Swishing her ponytail from side to side, enjoying the feeling of having Lucy’s hairstyle, Wendy looks up at Ezra. With a confused expression, Wendy leans in towards her.

“Lucy’s a role model…?” Wendy questions with a whisper. “She’s so feminine…?”

Ezra’s happy expression quickly drops, as she wonders what Wendy is getting at.

“Yeah…..she’s stunning!” Ezra answers a little confused.

“Yeah…,” Wendy says with a devious wink and smile. “I guess he really is very stunning. He’s a real role model to me too! I’m assuming you don’t know that Lucy’s a crossdresser as well….?”

“What!?” Ezra asks stunned. “Lucy’s a……”

“Yup!” Wendy answers interrupting. “Keep it down though! I don’t think anyone else knows. I don’t think she’s told, anyone!”

“Oh….ok!” Ezra nods. “We should go talk with her. She will deffo help with your look. She’d probably let you borrow a bra so you can get a feminine shape like hers.”

Bouncing with excitement, Wendy claps her hands together.

“I didn’t think of that!” She smiles. “Let's go talk with her now!”

“Sure!” Erza nods and moves to open the door. “I can’t wait to see you with breasts like hers!”

Stopping just at the door as Ezra holds it open, Wendy gives her a shocked look.

“We can do that?” Wendy questions with pure excitement. “Does your transformation magic allow for me to have ful; breasts like that?”

Nodding, Erza gives a wink.

“Sure,” she says with a huge smile. “Still, if what you are saying about Lucy is true, she’d probably let your borrow her breasts forms anyways!”

“Oh yeah!” Wendy grins and walks through the door. “I can’t wait to show her my hair like this!”

Following Wendy back into the main hall, Erza can’t help but smile from ear to ear. Catching up with Wendy, she leans down to whisper in her ear.”

“Thank you for telling me!” she says quietly. “I’m so happy that I’m not the only one now. I can’t wait to help you look sexier! The boys aren’t going to know what to do!”

Wendy looks up and squeezes her eyes closed with joy.

“I’m excited to!” she cheers.