A Tooth Fairy's Transformed Intern

Elizabeth here: this story contains MTF gender transformation. Enjoy!

~~~~~ ~~~~~

Cecil still had one baby tooth left at the age of twenty-five. It was a lower right canine tooth that refused to come out no matter what he did to it, and over the years, he had tried everything short of a pair of bulky pliers. He tried to accept that it wouldn't come out, but every now and then, he fantasized about how it would feel to have a normal sized tooth there, and about the ten bucks he'd get from the tooth fairy after putting the tooth under his pillow...

At least his pink themed suite on the tenth floor of a downtown apartment building was nice enough for him to forget about it most of the time. The previous tenant had painted all the walls pink. When he had moved in two years prior to get his publishing job in New York, he thought about painting them white again, as the landlord didn't really care what color the walls were, but something kept him from painting them, and he eventually grew fond of them. Weeks after he moved in, he started to buy furniture to go with it: a red microwave for the kitchen, a pastel pink couch for the small living room, and a pair of lovely pink bedsheets and red heart pillows.

When his friends were over, he just told them that he bought this particular furniture because it was super cheap, and they believed him. Though, when the pizza guy mistook him for a girl one time, an odd wave of comfort shot through him. He was short, and his light blonde hair did look a little feminine. And he liked to dress in cute pastel colors too, just because it fit with the aesthetic of his apartment. But he corrected the pizza guy and paid him. Though, it was embarrassing enough for him to try out local places instead of the Papa John's for the first time, and the local pizza was so good that he never ordered from a chain place again.

It was Friday evening. Cecil was on his laptop at seven in the afternoon, sitting in his rolling leather chair. His laptop had a little hole in the right side of the casing but other than that, it worked perfectly fine. Cecil was wearing his pastel yellow sweatpants and long pink shirt. It was cold outside, and he felt comfortable here while he caught up on his emails. He was absentmindedly prodding around his teeth with his tongue when he felt something unusual. That baby tooth wiggled when he poked at it. It didn't hurt, and there was no blood. But all of a sudden, it was loose.

This was what he had been dreaming of for years.

"Woohoo!" he quietly shouted. There were neighbours, but he felt the need to celebrate. He went to his fridge in the kitchen and rustled around the back until he found the Hello Kitty themed red soda that he bought on an overseas work trip one time and was saving for a special occasion. After making sure it was there, he put it in the door of his fridge so that he could grab it easily after the tooth was gone.

While on his computer, finishing the last few emails, he kept tugging and pulling and pushing at it; there was no blood and little pain, and it gradually became looser and looser, and he grew more and more excited.

When he was younger, teeth took a while to get loose enough to remove, but this one was getting loose much, much more quickly. In only an hour it was almost out; he could slip his tongue under the rear half of the tooth, where it had separated from his gum.

As he sat in his chair, eagerly wheeling it on the plastic chair mat on top of the light brown carpet, it grew looser and looser, and was soon barely hanging on to his gums.

Then he gripped it with two fingers, and tugged it gently. It barely budged. He pulled harder and harder, and finally, it popped out of his mouth with a cathartic sound and only minor, enjoyable pain. He did it! He probed the spot with his tongue: yes, there was an adult tooth coming in underneath it, which was probably why it was so easy to remove.

He went to his fridge to get out the red Hello Kitty soda, and brought it to his desk. He sat at his desk, opened the soda, and took a delicious swig. It was cherry flavor, and it was cold and bubbly. His gums around the missing tooth were sensitive, but he didn't care.

He knew he could put the tooth under his pillow and get ten free dollars. Although he briefly considered keeping the tooth as a memento, he decided against it, since giving it to a tooth fairy was just what you were supposed to do with teeth, and it symbolically represented growing up and whatnot.

Then he went to look for his tooth. It wasn't by his mousepad where he thought it was. Weird. He checked the other side of the desk. Not there either. Then under the keyboard, behind the monitor, and on the plastic chair mat.

Now he was panicking. Where was that tooth?

It wasn't on the desk. It wasn't on the floor. He checked his pockets, and it wasn't there either. Where was it? He went to the fridge. It wasn't there either.

He scanned his whole apartment and couldn't find the tooth. How did he lose it so quickly? Did he throw it away? He searched the trash too and found nothing.

It wasn't until eleven-thirty that he finally gave up the search. He was angry that he couldn't get rid of his tooth the way he was supposed to, and tried to think of a plan...

...maybe he could just use a fake tooth. Maybe it could symbolically stand in for his real one. And he did have clay, glaze, an oven, and some old tools left over from his pottery phase a year ago...

So, he spent the next hour and a half carefully sculpting a baby canine tooth using images online. He was desperate to symbolically send off this tooth that had plagued him for years, and was eager to see the process completed without a hitch.

Finally, at two-thirty in the morning, the tooth was glazed, fired in his oven, and ready. It was as close to a perfect imitation as he could get it. And tooth fairies were always in a hurry, so surely they wouldn't notice.

Still in the same pastel yellow sweatpants and pink shirt he was wearing earlier, he prepared for bed and slipped under his covers. He held the fake tooth in his hands one last time before putting it under his heart shaped pillow. Cecil turned off the lamp on his nightstand and slowly drifted off with faint city noises lulling him to sleep...

~~~~~ ~~~~~

Cecil woke up at seven the next morning and rolled his head off his pillow. There was a faint crinkle under his pillow, and he excitedly sat up, lifted the pillow, and saw a ten dollar bill next to a yellow note, written in pink ink and flowery handwriting:

Hi, Cecil! I'm Florian, the tooth fairy for your part of New York. I'm running late and can't write a whole lot, but thank you for the tooth! Twenty-five is better than never, isn't it? You have a full set of beautiful adult teeth now, and I'm proud of you! Have a happy life, and be sure to brush regularly, okay?

Warm regards, Florian

He was happy that it went off without a hitch. Although he had drank that Hello Kitty soda the night before, he thought that he'd buy himself something nice with that $10. So, he put on his jeans, got ready for the morning, and ran to the store to buy himself a $10 box of strawberry pocky. He didn;t usually usually buy pocky, but the soda he drank the night before reminded him of the delicious sticks.

He had nothing to do that day, so he returned home and celebrated by changing back into his sweatpants, laying in bed, eating pocky, and listening to ASMR videos with his pink headphones on. His headphones had fuzzy pink cat ears sticking out of the headband, and wearing them gave him an odd warm and fuzzy feeling inside. While listening to some head rubbing ASMR, he absentmindedly played with his pocky, sliding it in and out of his mouth, licking off the strawberry coating, chewing the stick itself, and moving on to the next.

He only heard the knock on his door after the third knock. He immediately pulled off his headphones and stood up to deal with it.

He opened the door and what he saw immediately sent dread through him; a tooth fairy stood there, clad in a white dress and pink stockings. Her pink hair went down to her shoulders, and she had four shiny pink dragonfly-like wings on her back. She was standing there with her arms folded, and she was scowling.

"Cecil, right?" she asked. "I'm Florian. It was dark when I came in here, but I think it's you."

He tried not to shake. "Yes," he said.

"I need to ask you something," she said as she reached into a pocket on the inside of her dress. "What is this?" she said, pulling out the fake tooth Cecil made.

"I, uh, I can explain," he said.

"Please don't scam tooth fairies from now on. Now, this isn't a big deal; we can forget all about it if you just give me the ten dollars back, okay?"

"I don't have it," he said. "I made a fake tooth because I lost the other one." He opened his mouth and showed her his missing tooth. "See? My missing tooth! I lost it and I made a fake one and---"

"---No matter the excuse, you shouldn't ever send in a fake tooth. Just give me the ten dollars and I'll be on my way, and when you find your lost tooth, I can give it back to you."

"I already spent it and I don't have any cash," Cecil said. "Can I just pay with a card? Do you have Stripe or Apple Pay or anything?"

"Of course not!" Florian said. "This is a cash only business. Big Tech and Big Magic don't mix."

"Well if you just let me go to the ATM, I can do a withdraw, and give you cash. Just let me check my balance on my phone real fast, and---"

"You'd better hurry," Florian said.

Cecil opened his bank's app; he always logged out after using it for security reasons, so he logged back in and looked at his checking account.

$6.53, his app read.

"Oh," Cecil said. "I get paid tomorrow," he said. "Can I pay you back then?"

"No," Florian said. "Do you really not have ten dollars?"

"I don't," Cecil said.

"Seriously? Well, there's only one thing I can do. Sorry about this, but it's our policy." Florian reached into her dress and pulled a small white wand out of it. The wand had a cartoony gold star on the end of it.

"I can pay you back tomorrow!" Cecil said as he backed up and held his palms out.

She pointed the wand at him, and a ray of pink light shot at him and struck him painlessly in the ribs.

A wave of hazy sleepiness spread out from his chest and reached his head before even a second had passed. The corners of his vision blacked, and he staggered as he tried to return to his bedroom. Just before he passed out, his body grew warm and fuzzy. Then, he finally fell to the floor and blacked out.

~~~~~ ~~~~~

Cecil woke up. As soon as he felt the fabric of his bed against his back, he was happy that it was all just a dream.

Then he felt something crinkly and insect wing shaped on his back, and realized that sunset light was peeking through the cracks in his red curtained window. And, the lights in his bedroom were on.

Cecil jolted upward, and felt odd weights on his back and his chest. He looked down. He was in a green dress with a tooth emblem on it, and... was that a bra underneath it? And why was his chest so heavy? And as he shifted in bed, something felt odd between his legs. He couldn't see his legs, because they were under the blanket, but they felt different. As he looked at himself, his long hair swished in front of his eyes. It was pink now.

A sigh came from the door to his left. Cecil looked up again and saw Florian standing in the doorway, leaning on the frame.

"If you can't do the time, don't do the crime," she said.

Cecil started to speak. "What happened to---" He was cut off as soon as he realized how girly he sounded. And there was a conspicuous absence of something between his legs.

"Since you can't pay back the tooth fairies, and I'm overworked, I'm recruiting you to be my intern for the night. You're a girl now, and you're a fairy now. I already dressed you in an old uniform."

Cecil looked down. An odd buzz surged through him as he processed what had just happened.

"Why?" Cecil said. "I would have been able to pay you back tomorrow!"

"Company policy!" Florian said. "It's easier than small claims court, and you agreed to the EULA when you put the tooth under your pillow. It's like in those TV shows where the characters have to scrub dishes at a restaurant after they realize that they can't pay their bill. Now get up. A hundred people in this area lost one or more teeth today, it's getting dark, and people will be falling asleep soon. Also, your name is Saffron for the night, because Cecil is no name for a tooth fairy."

Cecil sat still. Was this really happening? He slowly pulled the blanket off his legs. Yes, he was clad in nothing but a green dress with a short, frilly skirt, and there were thick pink thigh-high stockings on his hairless legs. He leaned forward, lifted his skirt, and peered between his legs. He was wearing a pair of white panties, and there was nothing bulging inside them; there was only the odd sensation of his brand new femininity.

He was about to peek under his panties when Florian spoke. "Saffron, stop gaping at your missing dong, it's not like you ever used it."

"Hey," Cecil said. He put his skirt back and got out of bed. His now large chest bounced ever so slightly with every step, as did the wings on his back.

"Come on," Florian said. "Your hair is a mess. You can stare at yourself in the mirror while we do your hair."

Florian led Cecil to his pink-tiled bathroom. As soon as she turned on the lights, Cecil saw himself in the mirror. He was beautiful. The pink and green went wonderfully together. Messy pink hair, piercing green eyes, a face cuter than anything he had ever dreamed of, a green dress covering his wonderful breasts and the tops of his smooth thighs, the wonderful, pink dragonfly wings sticking out of little gaps in the back of his dress, and those pink thigh-highs that made his soft legs so, so wonderful and gave him a warm, fuzzy feeling in his groin...

Florian tapped him on the shoulder and offered him a hair brush. Cecil snapped out of his trance and took the brush.

"Saffron, stop lusting over yourself. I need to get you ready for a night of tooth-collecting."

As Cecil brushed his hair and Florian taught him to put on lipstick and use makeup, and how to apply lotion to his fairy wings to make sure they shined as much as he needed, he began to get more and more into his Saffron persona. It was oddly appealing and weirdly comfortable. And his new clothes even matched his apartment's theme.

"So, here's what you'll do tonight," Florian said when they finished and Cecil was even more beautiful than before. "I have a list of twenty addresses and names, a small wallet with two hundred dollars in it, and a set of magic lockpicks for you, which will instantly unlock every lock they touch. They're on your kitchen table. I expect you to go into each of these homes, replace the tooth with a ten dollar bill and a little encouraging note while the client is sleeping, and leave unseen. By sunrise, I want you back in your apartment with twenty teeth and an empty wallet, and then your debt will be settled and I'll change you back to normal. Don't mess it up."

Cecil wanted to know what would happen if he did, but didn't dare ask. He thought of something else to say instead. "If I'm supposed to be unseen, why did I need to dress up?"

"Because that's just what we do," Florian said. "We have to look good, even if nobody sees it. Any questions?"

"When do I start?"

"The names on the address sheet will glow when they're asleep. As soon as a name glows, you can start your route through town. Oh, and also, don't forget, you have wings, so you can go in through people's windows. Flying is easy, you'll figure it out. Anything else?"

"I... I don't think so."

"Good! See you in twelve hours or so. Now, if you excuse me, I have to handle the bulk of the clients around here tonight, and I need to leave." She walked out of the room and towards Cecil's front door. "Farewell!" She opened it, darted through, and shut it behind her.

Cecil was alone in the apartment. He was still processing everything as he walked to the kitchen, and repeated a phrase in his head over and over. "I'm a fairy girl now," he gently muttered. It was oddly intoxicating to think about. It was supposed to be a punishment, yet something about it felt tingly and fun.

He decided that it was his clothes matching the room's decor; that had to be the source of his odd, tingly comfort. Pink and pastel green: it was cute and girly, just like his apartment. A perfect match. And the pink and white kitchen did look like the kind of place a tooth fairy would own.

On the pink and white striped dining table was a sheet of notebook paper with the list of names on it, a small, pink wallet, and a set of white, faintly glowing lockpicks. He checked the names; none of them were glowing.

Cecil wondered whether he counted as male or female. He was male most of the time, but right now, his body was that of a staggeringly hot fairy girl. Was it his original body or his current one that mattered? He couldn't figure it out.

Eventually, Cecil had enough of it, and thought he'd use the given name in his head and think of himself as female. He gently tapped his knuckles against his head. "My name's Saffron, just for tonight," he muttered. He kept muttering it until he got into the mindset and the name and gender stuck.

With that out of the way, Saffron had a little bit of time to kill. None of the names on the list were glowing. So, she decided to get more familiar with her new body, and went to her bedroom.

Of course, she could be called to action at any moment, and there might not be time for a deep dive. So, she sat on the end of her pink bed and kept the list on her nightstand where she could see it. The soft, cool sheets felt wonderful against the exposed parts of her thighs. She smiled in delight. She was curious about her body, and wanted to explore as much as she could given the time.

Her wings beckoned for her touch. They were just hanging on her back, bouncing with every step. And she didn't have any time to properly feel them up until now: Florian had been the one to lotion them. So, she reached behind her back. Her slender, smooth arms were flexible, and she lightly gripped the tips of her upper wings. They felt smooth, sleek, and thin, and wobbled when touched. And she could feel the touch in her wings. They were sensitive, like the skin on her soft neck, even though they were made of something completely different. Whatever the translucent, pink wings were made of, it was addicting for Saffron to run her hands across them.

When she was done fondling and bending her sensitive wings, she looked down at her chest, which had been teasing her in the mirror ever since she woke up. Of course she had to probe it too. What else was she to do after waking up as a girl? This was the mandatory part of every gender swapping fantasy; touching the sexy bits.

But her dress wasn't so easily removed. It had a grand total of seven holes: one for both of her legs, one for each arm, and one for each of her four wings. When she grasped the skirt of her dress and tried to pull it up, it got most of the way up her body before getting caught on her wings. Still, the very bottoms of her breasts were exposed, as was her smooth belly and hips, and the pink panties around her groin, so Saffron just kept it there. She reached up through the front of her dress and ran a hand over her pink bra. If she could have just removed the dress, she would have been in all pink. Pink hair, pink bra, pink panties, and pink thigh-highs, on a pink bed in a pink room... the thought of all this pink made her shudder.

Then she decided she had to get the dress off somehow, for the pure pink aesthetic. The green was spoiling it. After reaching back around to her wings, she discovered that they were quite flexible, and could be bent and folded however she liked, snapping back to their original shape. And it wasn't even painful to bend her wings, though she still couldn't figure out how to flap them. So, she painstakingly brought wing after wing through the holes in the dress, until the last one went through, finally freeing her from her dress.