Crossdressing at a Renaissance Faire: How One Visit Changed Everything?

Ethan yawned and stretched as the first wave of the cheesy Renaissance Faire came over him. Its eclectic colors and boisterous music held little interest for the young man. He’d rather be home playing video games or watching sports, but after some cajoling from his friends. Here he was. 

He had chosen his outfit with care, not wanting to go the whole way to a full cosplay. But, he didn’t want to be a dude in slacks and a lame t-shirt either. So, he had grabbed himself a nice pair of worn, baggy brown pants. They had seen better days, mired with cuts and tears from long days. Then his shirt was white and puffy. The neck had a distinct ruffle that looked like it belonged in ye olden times.

He attended a few events, and none of them caught his interest enough. Most were boring. “No wonder these were left behind in time,” he groaned. Soon his stomach joined him in the chorus. Rumbling with a need.

The smell of the local food stalls only tempted him further. The legend of the oversized chicken legs had reached even his ears.

Yet, like the tantalizing smell, the not-so-tantalizing line came into view. It stretched back. It would be at least an hour of waiting through the lunch rush. He could either join now or kill a bit more time goofing off.

Ethan was one to procrastinate on his problems and wait.

Down the lane was a small purple tent. Eerie candles lit the outside even though it was still midday. A sign outside read “Madame Zara, Seer of Destinies.” It seemed like an amusing enough time-waster to Ethan.

Despite his disbelief in the magic of a fortune teller, he stepped inside. He also didn’t believe Renaissance Faires were worth going to. So, stepping outside his comfort zone seemed natural.

Madame Zara sat behind a velvet-covered table. She wore a colorful dress. It seemed to be a mix between Renaissance flair and TV show stylization. Her head lifted with that same dramatic flair. Her piercing green eyes peered over her crystal ball as she spoke. “Ah, young sir, you look like a man in need of some guidance.”

Her acting could use some work, but it wasn’t the worst in the Renaissance Faire.

Ethan amused himself by plopping down on the chair opposite her. He let a light chuckle escape his lips. “I’m here for fun,” he assured her. He pulled out a crumpled ten-dollar bill and placed it on the table. “But if you want to use your magic powers to tell me when the line for the chicken legs is shorter, I’d appreciate it.”

Her expression grew serious. She let her gaze drift over the room before landing on the crystal ball.  “I see your future. It is beyond your understanding,” she warned. She let her hands gesture over the crystal ball. “Great transformation awaits you this very day.”

“Yeah, right. The only thing I’ll transform into is a starving peasant.” He leaned back in his chair, not convinced by her vague premonition.

But as he shifted, his chair gave way beneath him. His pant leg caught on the table. It made a loud ripping noise as he tumbled backwards.  The sound of it ringing in his ears as he hit the dirt ground of the tent.

Madame Zara was up and circling Ethan in a second. Then she let out a playful gasp as she saw him.  “Ah, the fates are hasty today!” she exclaimed. Her serious expression was replaced with a playful grin.

The table tore his pants from mid-thigh down to the pant leg. Any fight they had gone with their seams. The waistband stretched with the tumble, and now they hung loosely from Ethan’s waist. They slumped, revealing Ethan’s boxers.

Still, Madame Zara was not a cruel mistress like Fate had been. She wandered to the side and gestured to the trunk she had stuffed in the corner. “I have my change of clothes for when I finish my shift in here. They may not be to your style, though.”

“More my style than walking around without pants.”

The fortune teller nodded with approval. They then opened the trunk and rummaged inside for a few minutes. Then they pulled out a skirt. Ethan’s jaw dropped at the sight of it. It was a soft fabric that seemed to glimmer. It was a deep blue. Silver threads were woven throughout it to mimic stars.

“You can’t be serious,” Ethan squeaked.

Madame Zara only smiled. “Take it or leave it,” she replied with a shrug, “But the chicken legs vendor has a strict, no pants, no service policy.”

Having never worn anything feminine in his life before, Ethan took it like it was radioactive. His hands shook as he felt the softness between his fingertips. The tent was too small. Not enough for a private changing room. So Zara had to be polite enough to turn away for Ethan to change. And Ethan had to be trusting enough that she wouldn’t peek.

The skirt was comfortable once he had managed to tie it around his waist. It almost felt like wearing nothing. It was so smooth and light. The breeze was threatening to twist up and expose his legs at the slightest provocation.

Still, he had a mission to do. The chicken leg awaited.

As soon as he stepped outside, he caught sight of something else. A group of giggling elves is dancing through the crowd. Baskets of vibrant flower crowns braced in each nook of the arm.

“For the lady!” One exclaimed, her voice rang with delighted laughter. Ethan had no time to protest. A flower crown was thrust into his hair. It nestled into his hair as the elves giggled and danced away.

Ethan sighed. It was his luck so far today, it seemed. His hands went up and tugged at it, trying to break it free, but instead it caught fast to his hair. Each tug sent waves of pain as it threatened to pull out what felt like not just his hair, but his whole scalp.

“Well, this is great,” he moaned with an angered stomp of his foot.

His stomach still rumbled with hunger as he drifted through the crowds. His thoughts drifted with him. The words of the fortune teller ringing in his ear, “Great transformation,” she had said.

Then he sighted it. A bar. A bar with a buxom barmaid with a hearty laugh as she attracted customers. Ethan cared little for the barmaid. He was more excited at the sight of the bar.

“A pint of your finest mead, if you please,” he said, trying to act up for the Faire himself. She gave him a curious look before shrugging. He figured his voice didn’t match his outfit. Either way, a glass of raspberry ale sat in front of him. He took one tentative sip, then downed it. The red berries coated his tongue and lips with their flavor.

Ethan let his lips smack with satisfaction from the drink. His reflection now showing in the emptied glass, he could see a peculiar stain on his mouth. There was some staining from the raspberry ale around his lips. He chuckled to himself.

The slight buzz of the ale made him think it almost looked like lipstick. The buzz eased his embarrassment while the ale pressured his bladder.

He needed the restroom.

He stood up and felt his legs wobble. He grabbed the bar for support. He wasn’t used to the skirt yet either. Felt like one wrong move would send him tripping over it. But that wasn’t to say it felt bad. He strode forward. 

He was about a half-stumble from entering the men’s room when a hand grabbed him. It was dainty, yet firm. “Oh, no, my dear,” a sweet voice said. “This way. You’re not going in there dressed like that.”

Ethan looked up to find a woman dressed as a knight in a homemade costume smiling down at him. Her armor was that of painted cardboard, and her sword was a wooden stick with aluminum foil wrapping. It was a sight to behold.

She didn’t say a word, but gave him a firm tug. A tug towards the women’s restroom. His own embarrassment at his garb kept him from speaking up about the confusion. He could play along for one potty break.

Once inside, he locked himself in a stall and took in his reflection in the mirror. The skirt looked good on him, cinching at his waist and flaring out right over his legs. The flower crown added a feminine touch to his hair. Making even his short hair look like a girl’s.

His cheek had a natural blush from the drink and embarrassment. His lips had the red tint of his drink still on them. He finished up there and left the bathroom.

The woman who had guided him to the restroom was waiting outside. She seemed amused by him. Amused enough to hook her arm around his at least. Then, with a bit more of her forwardness guided him over a nearby table. A few other women were sitting at the table sharing a meal.

His ‘rescuer’, the female knight, lifted his makeshift sword into the air. Then she declared with a booming voice, “Behold, I have rescued a fair maiden. Shall we journey on with my newfound companion!”

He found himself drawn into their merriment. They were roleplayers who did this at every Renaissance Faire. There was a wizened wizard, a farmer’s wife, and a poor peasant woman. The woman who had rescued him was a knight out to rescue her fair princess.

Ethan was happy to play that role.