1
A Hundred Dollars and a Plan

“Look, that’s insane,” I said, crossing my arms. School had just ended and we were hanging out in Shane’s living room when he asked me an inane question. “I am not doing that, go find an actual girlfriend”

“Bro, please,” my friend Shane said, begging me. He literally clasped his hands together and was on his knees. “Just pretend to be my girlfriend for a few hours, I swear it won’t be a big deal. All I need to do is get Hailey’s attention.”

“No, I refuse,” I said, shaking my head. “Can’t you rent one online? I heard some services offer that.”

“We live in the middle of buttfuck nowhere in Iowa, I don’t think there are any rental girlfriends here,” he said, sighing. He looked down at the floor for a few seconds before looking back up and staring at me dead in the eyes. “Look, I can give you one hundred dollars if you do this for me.”

“Now, that makes me actually think,” I said, pointing my finger at him. “If you said that in the first place, I might’ve agreed.”

“I was trying to save my money, alright,” Shane said. “Now, is it a deal? One hundred dollars and you’ll dress up as my girlfriend for Hailey’s party tonight.”

“Hmm, but first we need to see if I’ll even pass as a girl,” I said, rubbing my chin as I thought.

“Are you kidding me?” he asked, tossing his arms up into the air. “You get mistaken as a girl every day and that’s without any effort on your part. Toss in some makeup and you’ll easily pass as a girl.”

“Do you know how to do makeup, did you even think this out?” I asked, realizing that this very flimsy plan appeared even flimsier the more you thought about it. “Who’s going to do the makeup for me?”

“Umm,” he said, awkwardly scratching at his cheek. “I didn’t think of that.”

“Yeah, you didn’t think of shit,” I said, staring at him disappointedly. “What is your full plan anyway?”

“Okay, look,” he said, acting like he was about to dump a massive revelation on me. “Hailey sees me with a girl at her party and she gets jealous, right?”

“Yeah.”

“So then she’ll try and ask me about the girl, and then we can strike up some conversation,” Shane said. “After that, I’ll start giving her lots of compliments and tell her how amazing she is and then she’ll like me.”

“Seriously?” I asked, letting out a little laugh at how terrible of a plan that was. “But you can’t even find an actual girl to do this with?”

“Heh, I mean, what can you do right?” he asked, chuckling.

“Fine, then who’s going to do my makeup?” I asked, idly swinging my legs. “I’ll go along with it but only for the hundred dollars. Ugh, this is going to be embarrassing.”

“Okay, my older sister, I’m sure she’ll agree,” Shane said. “Come on, let’s go to her real quick. She’s just upstairs.”

***

“What the fuck?” Shane’s older sister said, squinting at us. Shane had just explained his plan to Claire, and she was as confused as one could be. “You want me to dress up Adam as a girl?”

“Look, Claire, please,” Shane begged again. He was doing a whole lot of begging today. “I seriously need a date for Hailey’s party. You’re not allowed to attend without one, and I can’t think of any girl who’d want to go out with me.”

“You seriously can’t find anyone to go out with you?” she asked, sniggering at Shane’s situation.

“Look, I’m a loser, okay, I get it,” Shane said, sighing deeply. “But can’t you just do this for me? Please?”

“You know what, fine,” she said, exasperated. “I’ll go along with this batshit plan of yours. But you definitely owe me one after this, alright?”

“Sure, I can do anything,” he replied.

“Anything?” she said, an evil grin forming on her face.

“Within reason,” Shane replied.

“Great, let’s get started then Adam,” she said to me. “Come here, we’re going to need to get rid of your body hair first. I don’t think you have any facial hair, so that won’t be a problem.”

“Yeah, puberty has been really light on me,” I said, awkwardly laughing as I was led to the bathroom. I was fifteen and was still only five feet and one inch tall. Body hair was just as prevalent as it would be on any fifteen-year-old boy though.

“Let’s see, you could shave, but I don’t really want you using my razor,” she said, picking up her razor and twirling it around her fingers like a pen. “Oh, I have the perfect solution.”

“That is?”

“Nair!” she said, picking up a bottle excitedly. “It’s perfect, it’ll remove all your body hair in just a few minutes.”

“Never heard of it,” I said, sitting down on the edge of the pearly white bathtub. “So, what do I have to do?”

”Just rub it around and wait a few minutes,” Claire said, shrugging. “It’s really simple. Just take off your shirt for me.”

“Woah, hold on a second,” I said, so surprised that I almost fell into the bathtub. “Can’t I do it on my own?”

“I don’t trust boys, you’ll probably spread it all unevenly,” she said, shaking her head. “You’ll have half of your leg hairy and half smooth.”

“I promise I’ll do it perfectly,” I said, trying to put on the most pleading face I could. “All you have to do is give it to me.”

“Just take off your shirt,” she said, not having much patience.

“Fine,” I said, a little scared by how authoritatively she said that. I took off my grey t-shirt and tossed it over the towel holder.

“Wow, are these pecs or boobs?” she asked, squeezing at my chest.

“Hey!” I said, quickly grabbing my shirt. I began to put it back on while Claire tried to stop me.

“Look, I’m sorry, your chest is just a lot fuller than I expected,” she said. “I won’t comment on your body anymore, come on.”

“Okay, fine,” I said, putting the t-shirt back onto the towel holder. “Don’t do that again, it’s embarrassing.”

“Sorry, sorry,” she said. “Okay, raise your arms now.”

I complied, raising up my arms. Claire squeezed some of the product out of the bottle and spread them over my armpits. She then moved on to my legs. After a minute or so, I was absolutely covered in the lotion.

“Great, now we just have to wait three minutes,” she said, setting a timer on her phone. We awkwardly stared at one another for about a minute before she opened her mouth. “So, why are you agreeing to do this for my stupid brother?”

“He said he’d give me a hundred dollars,” I said, imagining what I could do with that money. Maybe I could put it towards a new bike. Or buy some video games, I was getting bored of Call of Duty.

“And he’s not paying me?” she asked, sounding offended. “Makeup and Nair don’t come cheap, you know.”

“I guess you can just say it’s your sisterly duty?” I suggested, laughing at how ridiculous it sounded.

“Yeah, my sisterly duty is to dress up my little brother’s friend as a girl,” Claires said, laughing along with me. “I knew Shane couldn’t get a date but damn, having to get his friend to dress up as his date. That’s a new low for him, and I thought he couldn’t get any lower.”

“I’ve gone along with worse for less,” I said, shrugging. I cringed as I remembered the time he made me his wingman to ask out the most popular girl in school. It did not go well. That most popular girl at school also turned out to be Hailey, the girl whose party I’d be attending tonight. I was surprised Shane even managed to get invited.

“Yeah, you’re like, his bestie or something.”

“I guess we are best friends, yeah,” I said, thinking. “Although it’s mostly me following along with his stupid plans.”

“Yet here you are, following along with another stupid plan,” she said, giggling.

“I guess I am.”

“Also, how are you-” Claire stopped speaking when the alarm on her phone rang. “Oh hey, it’s been three minutes. Okay, time to wipe it off.”

“What were you about to say?” I asked, tilting my head.

“Oh nothing,” she said as she dampened a washcloth. “Here, let’s get all that Nair off.”

She wiped off the lotion with the cloth, and the little body hair I had was taken away by it. Considering I had no other body hair, I was officially all smooth. I rubbed my legs together, it felt a little weird but nice.

“I don’t even think I have to do any makeup, you look like a girl already,” Claire said, inspecting my face. She gently touched my face and frowned.

“Gee, thanks,” I said, looking down at my hairless legs. “Way to reinforce my masculinity.”

“Yeah, no problem,” she said nonchalantly. “Okay, put your shirt back on. We have to get your makeup done.”

I put on my shirt and headed outside where Shane was waiting. He looked at me, and then at my legs, and then back at me. He laughed. “No hair now, huh?”

“I expect those hundred dollars,” I promptly responded.

“Okay Shane, get out,” Claire said, opening the door for him.

“Why can’t I stay?” he asked, looking out the door and then back at Claire.

“You will witness the transformation when it is over,” Claire said, gently pushing Shane out the door and closing it. She turned the lock shut and then headed over to her vanity. She draped a green blanket over the mirror and then pulled out the chair. “Sit here, Adam.”

“Why did you cover the mirror?” I asked, taking a seat on the chair.

“I want you to look at yourself by the end and be all surprised, I think it’ll be funny,” she said, giving me a quick smile.

“I mean, what difference is makeup really going to make?” I asked, rolling my eyes. I think she was overestimating its effects.

“We’ll see.”

She took out some brushes, lipstick, and more items I didn’t know the name of from the vanity and lined them up on the table. She started immediately, and I just awkwardly sat there looking around the room. All I could notice was that Claire’s room was pretty messy, with a bunch of stuff strewn over her bed and floor. I looked back at the mirror that was covered and frowned. Would makeup really have that much of an effect on me? She applied a bunch of stuff on me and it felt weird, my face felt oddly heavy. I don’t know how girls did this every day, I would be exhausted. It took a few minutes of silence until Claire spoke up again.

“Now just don’t twitch your eye too much when I do this and you’ll be fine,” she said, pulling out a tube of eyeliner.

“I’ll do my best,” I said, opening my eyes as wide as I could.

“Geez, I told you to just not twitch it, not open them that wide,” Claire said, giggling. ”It’s okay, just keep it that way.”

She gently applied the eyeliner and I had to resist the urge to blink a bunch. It felt super weird.

“Great, we’re done with that,” she said, putting down the tube. She looked over my face with her hands on her hips. Her neutral expression slowly turned into a smile. “We’re all done then!”

“We’re done?” I asked, resisting the urge to touch my face. God this all felt so weird.

“Yeah, now it's time for the grand reveal,” Claire said. She did a quick drumroll on the vanity before ripping the blanket off the mirror. I saw a cute girl. A super fucking cute girl. Besides her blonde hair, which looked a bit like a rat’s nest, she was the definition of adorable. It took a few seconds to realize the girl in the mirror was me.

“Wait, wait, wait,” I said, needing a second to process everything. I could hardly recognize myself. Even the pimples I had grown to be so accustomed to had disappeared, being concealed by the makeup. “That’s me?”

“That’s you alright,” she said, smiling. “I did a pretty good job, huh?”

“I never thought I could look this good as a girl,” I said, awkwardly stroking at my hair. I never did take good care of it, and it kind of ruined my image. To have a girl so cute with such uncared-for hair was a little disappointing.

“Oh, your hair does look a little bad,” she said, rubbing her chin. “Let me see what I can do, I’m no hairstylist but I should be able to make it look at least a little cleaner.”

Claire went to work, using a hair straightener, hair rollers, and a scissor I’m pretty sure wasn’t meant to cut hair. It worked though, since by the end of her little session, my hair looked a lot better.

“Okay, are you ready to call in Shane?” she asked, putting her hand on the room’s doorknob.

“Yeah, sure,” I said, still admiring myself in the mirror. If I could date myself, I totally would.

“Shane, your girlfriend’s all ready!” Claire opened the door and yelled down the stairs. “Get off your dinky game and get up here.”

I heard some thumping up the stairs and before I knew it, Shane was at the door. I turned around to look at him and saw his eyes widen.

“Holy shit, is that you Adam?” he asked, walking into the room. He let out a loud laugh. “No way. There’s literally no way.”

“The one and only,” I said, smiling a little.

“Hailey’s going to go crazy when she sees how cute my date is,” Shane said, grinning. “Holy shit you’re cute. I knew you would be cute if you dressed up as a girl but wow, this is more than I expected.”

“Thanks, I guess,” I said, blushing a little. I didn’t get complimented too often, and being called cute felt nice.

“The only issue is, we can’t have Adam wear this to the party,” Shane said looking up and down at me.

“Oh shit,” Claire said, opening up her closet. “I’m so stupid, I didn’t get you any clothes to wear.”

“Uhh, can I just wear what I’m wearing right now?” I asked, looking down.

“Yeah, a nasty t-shirt and shorts, totally what a girl would wear to a party,” she said, rolling her eyes. “No, you can’t wear what you’re wearing right now.”

“Exactly,” Shane said after her. “I need you to look as good as possible to make Hailey jealous. That nasty shirt is not it.”

“My clothes aren’t nasty,” I murmured, looking down at my outfit. Did it look that bad?

“Uhh, my clothes are definitely too big to fit you,” she said, looking down at me. She stood a solid few inches taller than me, and her clothes would look oversized if I wore them.

“So, what are we going to do?” I asked, tilting my head.

“We’re going to have to head outside, of course,” Claire said. “To the mall, we go.”

“What?” I said, freezing up. “I can’t go outside like this!”

“You were meant to go to the party with me tonight, remember?” Shane said, frowning. “So you were going to go out today anyways.”

“Yeah, but I would just stand around at the party for an hour or two and leave, there wouldn’t be many people,” I said, suddenly getting very self-conscious about how I looked. “The mall is a different story.”

“Well, we have to get you some clothes somehow before seven,” she said, shrugging. “I’m invested in this now so I can drive us there. Otherwise, there’s no way this plan will work.”

“Fine,” I said, sighing and looking down at the floor. No one would recognize me, right? “I’ll go.”

“Shane, it looks like you’re going to have to spend some more money to get your pretty girlfriend some clothes,” Claire said, laughing.

“Shit,” Shane said, letting out a loud groan. “Fine, but nothing too expensive. You’re seriously breaking the bank, Adam.”

“Hey, you’re the one who needed someone for the party,” I said. “It's not my fault you can’t get a girlfriend.”

“Shut up, you weren’t even invited,” he said. Damn, that hurt more than I expected. I don’t think Hailey even knew I existed.

“Okay, stop arguing, let’s go now,” Claire said, rolling her eyes at our little argument.

“Fine,” I said. I looked at myself in the mirror one last time before heading out the door, ready to go out as a girl for the first time.

amaty

Welcome to The Trashiest Transfem Story of All Time! This is an attempt to write as trashy of a story as I can. If you're asking how I'm measuring the trashiness of this story, there was a trashy transfem fic bingo created in a server I'm in.  I'm trying to knock out all 25 of the boxes. The bingo and the number of boxes checked off this chapter are in my Discord because the image function isn't working for some reason.

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