Punk to Princess

Hello patrons! You chose "Punk to Princess!"

I'm sorry this is late, but the story just ran the hell away from me, and then I decided that the only way I could hope to tell it was by creating the images...

...and so here we are at very, very early in the morning / late at night.

😂

I hope you like it!

P.S. The images are really big, so I made them attachments in case you'd like to download.

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I’d always been drawn to the punk lifestyle. It was all about anarchy, freedom, and having fun. I loved the music, the style, and—most of all—the attitude. “Fuck you” wasn't just my favorite insult; it was practically my entire life philosophy. 

The world was fucked, I decided, and I would be part of making things even worse. I had no respect for authority. That included the police, the government, and any other bastard in a position of power, and my goal was to make their lives a living hell. 

At least, that was the plan...

But the system has a way of finding your weak spot and fucking you raw and hard. For me, that was my mom. She got sick. Real sick. It started with a cough, the type you expect from a smoker. Only she didn't smoke. Turned out she had lung cancer, and it had spread throughout her body like wildfire. The medical bills skyrocketed. She lost her job since when she wasn't in chemotherapy, she was too sick to work. So I did what I had to do: I got a job. I might’ve been a punk, but I wasn’t an asshole.

I was hired by the Renaissance Fair, where local nerds dressed up as knights and ladies and pretended the Middle Ages weren't a fucking dark time of ignorance and violence. I still had no respect for the authority figures there, but at least they weren't cops or politicians. I played the role of a lowly peasant. The job paid shit, and they worked me like a slave, but there were perks. For one thing, the girls were cute and easy. For another, I could sneak drinks while no one was looking.

One day, I was working at the beer tent, serving over-priced lager to the upper-class wannabes, when I saw her: Monica. She had long auburn hair, a gorgeous face, and a killer body. She played “Princess Jane,” the Fair’s pretend ruler. But from the moment I saw her, I’d known she was one of “those” girls. The kind who’d fuck a guy like me just to piss off her parents. 

I decided to make my move. I stole some cheap booze from the tent and made my way over to her. She was standing by the jousting arena with a large crowd, watching as two men in armor rode horses at each other and tried to stab each other with pointy sticks.

“Hey,” I said, leaning against the metal railing and looking down at her.

“Oh, hey, Jon,” she said, then narrowed her eyes at me. “Wait, what's your size?”

“My what?” 

“Your size. You know, for clothes.”

“Oh,” I said, totally thrown. “A...medium.”

Monica gives you a face. “Liar. You're a small, aren't you?”

“I meant my dick is a medium,” I said, then winced. Shit, that hadn't sounded good at all.

But Monica laughed. “Okay, look, I have a favor to ask you. It may sound crazy, but hear me out. You know I play the princess, right? Well, look, my boyfriend has the day off today, and we want to go fuck. So, uh, would you stand in for me?”

I raised an eyebrow. “Stand in...? You mean, like, dress like a fucking princess?”

Monica nodded. “Yeah. Look, I’ll pay you five hundred bucks, and all you have to do is walk around and look pretty.”

“Five hundred bucks?” I did some quick math in my head. Five hundred bucks would cover the rent for the house for the month. “I don't know,” I said. “I'll look ridiculous in drag. Hell, Mr. Eddie might fire me.”

Monica shook her head. “With the right wig and makeup, you'd make a really pretty girl.”

“Why don’t you ask one of the other chicks?”

“I did! They all said no. C’mon, it’ll just be silly. Everyone here is drunk anyway. You game?”

I sighed. It was punk to fuck with gender, right? “Okay,” I said. “I'm game.”

Monica clapped in delight and led me off to the changing tent where she handed me “Princess Jane’s” dress. I changed in the tent, then came out to model my new outfit for Monica and some other guy, who looked like a reject from a vampire movie.

“Perfect,” Monica said. “But you have to take out all of your piercings, then I'll do your makeup. I'm telling you, Jon, I don't think anyone will know you're a guy when I'm through with you.”

I shrugged and plucked out my piercings and handed the jewelry to Monica, who put it in her purse.

“Perfect,” she said. “Do you mind if I pluck your eyebrows? I know that's asking a lot, but it'll help.”

“I, uh…”

“Great!” she said, then sat me down on a stool and applied foundation, powder, blush, eyeliner, and mascara. It took a while, but soon enough, she stepped back to admire her work. “Amazing,” she said. “I told you you'd make a cute girl.”

She held up a mirror and, damn, I had to admit, I looked pretty good. If someone hadn't known me, they might never suspect I was really a guy. “Thanks,” I said, unsure if I should really thank her for emasculating me. After all, I still wanted to screw her!

“No problem,” she said. “Now, just stand over there and wait for your big debut.”

I did as I was told and stood around while the crowd milled around the fairgrounds. Soon, the vampire-looking dude announced that “Princess Jane” was about to tour the Fair, then nodded at me. I took a deep breath and headed out.

I walked through the crowd, feeling really weird. I got a mixture of reactions; it seemed like some people could tell I was a dude, but others weren't sure. When I reached the end of the crowd, I turned around to walk back through. I was sweating bullets and quickly decided the only way to get through this was to ham it up and entertain the crowd. That way, they wouldn’t care if I was a dude in a dress.

So that’s what I did. I flitted around and waved to people. They laughed and cheered. And, amazingly, I actually started to enjoy myself. For the rest of the day, I had to strut around the fair, stopping every so often for a photo opportunity. I kept hamming it up as much as I could, and by the end of the day, I was totally exhausted but also totally satisfied. 

I returned to the tent and changed out of the dress and into my regular clothes. As I was leaving, Mr. Eddie approached with a smile on his face.

“Jon, Jon, Jon,” he said. “That was some of the best entertainment I've seen here all summer! You really brought a whole new element to the Fair!”

“You mean you're not mad?” I asked.

“Mad? Why would I be mad? That was brilliant! In fact, what would you say to a permanent position? I'm sure the fans would love for you to be the permanent Princess Jane!”

I was shocked. Work as the princess permanently? “But what about Monica?”

“Hey, she bailed,” Eddie said. “As far as I'm concerned, the position is yours. And I'll pay you a thousand dollars a week instead of her five hundred. You were working way harder than she ever did.”

“But,” you say. “I'm not a girl.”

Eddie laughed. “Hey, no princess is perfect. So what do you say, Jon?”

A thousand a week to goof off in a dress all day? That was a lot of money, and mom and I were drowning in bills. “I’ll…I’ll do it.”

“Fantastic!” Mr. Eddie cried. “You’ll be great.”

And I was. I was Princess Jane for the summer, and, I had to admit, it was a lot of fun, and I got a lot of attention. Little by little, I became an expert on my character. I learned to move a different way, speak in a different tone. I learned how to sit, how to stand, and—most important —how to turn heads and get the crowd's attention. Soon, I began to be featured on the billboards advertising the Renaissance Fair! 

“Princess Jane: The face that launched a thousand dreams!” the billboards read. 

I was so popular, in fact, that Mr. Eddie wanted to extend my contract for another three years and double my salary. There was only one huge catch: Eddie wanted me to take female hormones. He reasoned that it would help immerse me in character. Sure, I’d still be living as a man outside of work, but I’d be spending practically all of my waking hours as a woman. It was a lame excuse. He just wanted me to grow tits. I knew it, and he knew that I knew, but the money was just too good. I agreed.

“I guess I'm just going to have to get used to this,” I told myself in the mirror, looking at the slight swellings on my chest. The hormones were working. Soon, I wouldn't be able to recognize myself.

When the next summer rolled around, and it was time to go back to work, I was ready. Well, more specifically, my body was ready. It had taken to the estrogen like a fish to water. The “swellings” on my chest had blossomed into a pair of C-cup breasts, and my ass had gotten wide. My face had slimmed as well, eliminating my square jawline for a heart-shaped one. I was, without a doubt, the most beautiful woman at the fair. 

As time wore on, I got used to being called “princess” by everyone almost all the time. The money was excellent, and the job was a lot of fun. Since we didn’t have to stress about money, mom could focus on healing. She’s been in remission for six months!

My only regret? I never did get to fuck Monica. And now, thanks to the estrogen and the fact that my “medium” dick has shrunk to whatever is under “small,” it looked like you never would.

Then again, Connor the Blacksmith has been giving me the eye lately...