Countdown to Confidence

Countdown to Confidence
by Peregrine

Copyright © 2023 Peregrine
All rights reserved.
This is a work of fiction. Names, characters, businesses, places, events and incidents are either the products of the author’s imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental.

Karla walked into the apartment she shared with her brother. Hanging up her coat in the closet next to the door, she turned, looking over the island separating the two rooms as her brother put on an apron.

“You’re making dinner? What are you going to make?” she asked.

“I was thinking I’d make spaghetti and meatballs.”

“Hey, is that my good skirt you’re wearing?” she asked. Her brother looked down at the skirt.

“Don’t worry. I’m wearing an apron. You said I could raid your closet whenever I wanted to.”

“I said you could wear anything on the right side.”

“This was really close to the right.”

“Come here. Let’s have a look. Do a spin.”

Her brother took a step into the room and did as she requested. Ray had a petite build and stood at a height of five foot four, matching his sister. He was wearing a pink shirt tail sweater with a pink raglan skirt coming right above his knees. He sported three inch black wedge booties with thigh-high black stockings encasing his legs.

“You look good in that outfit. I’m not feeling spaghetti. How about we go out for dinner? You’re dressed for it.”

“Funny. I’ll go change,” he said, as he took off the apron.

“Wait. I’m getting a picture of you. It’s a shame to waste how you look by staying in,” she said as she took a picture.

“I don’t have the confidence to go out.”

“You wouldn’t have to worry if you learned how to do your makeup.”

“I’m a closet cross-dresser. I’m content with dressing in the house.”

“How do you know you’re content if you’ve never been out dressed?”

“I prefer to stay in the closet.”

“Suit yourself. Go change so we can leave.”


Brother and sister were sitting in a booth having dessert after dinner.

“I have good news. I got the cruise ship job.”

“That’s great. Were you the only one who volunteered?”

“Oh, you’re funny. I hope I live up to their faith in me.”

“You’re a fantastic photographer. You’ll have fun taking pictures of people and events on the cruise ship. When do you start?”

“The job starts in January and I won’t be home until late December.”

“You’ll be gone for almost a year?”

“Yeah. Don’t worry. I’ll make sure you get the rent money.”

“I’m not worried. You only have a couple of weeks to get ready.”


As they got home, Karla’s phone vibrated, and she saw it was her friend Ashley.

“Hey, Ash. Tomorrow? Sure. After we can have lunch. Ray? I’ll ask him. See you tomorrow.”

“What did Ash want?”

“We’re going to a New Year’s Eve party. She wants us to get new outfits tomorrow. She told me to ask you to come with us. You always know what looks good on us.”

“You two will do fine without me.”

“So, what are you doing for New Year's Eve?”

“Staying home and watching the ball drop on TV.”

“Boring,” said Karla.

“I enjoy watching everyone being cold while I’m warm on the couch. Besides, I have nothing to wear,” Ray said with a laugh.


Karla and Ashley came back from shopping, carrying what seemed like a dozen bags. They found Ray wearing a tight light-blue long sleeve top that showed off his stuffed bra. He wore a denim mini-skirt with running shoes matching the top.

“Hey, Ray. Looking nice,” said Ashley.

“Thanks. You look good, as usual.”

“You won’t believe what we found,” said Karla. She unboxed a pair of three-inch, glittery silver sandals. “Aren’t they adorable?”

“They are very cute.”

“They go perfectly with my dress.” She pulled out a black, sequined, V-neck, short-sleeved party dress. “I even found the perfect clutch for the outfit,” she said, showing off the sequined silver clutch.

“What did you find, Ashley?”

“Have a look.” She pulled out a sleeveless dress and matching shoes.

“Really nice,” said Ray. “You guys did great!”

“And everything was on sale.”

“That’s even better!”

“Are you sure you won’t come with us to the New Year’s Eve party?”

“I’m not confident enough that I can pass. Besides, I have nothing to wear. Staying at home suits me fine. There are enough snacks if you want to join me.”

“And not show off my new outfit?” said Ashley. “Not a chance.”

“You mentioned you had nothing to wear. Would you go if you did?” said Karla.

“If I did what?” said Ray.

“Have something to wear.”

“What are you talking about?”

Karla pulled out a red, long-sleeved, mock neck, mini party dress, with all over sequin embellishments, then unboxed red sparkly three-inch pumps and a red clutch. “I bought these for you. Come with us. I don’t want you to be alone on New Year's Eve.”

Ray looked at the outfit and imagined how he would look in it. The outfit was almost too tempting for him to refuse. “Thanks, sis. You make it hard to say no. I’m not confident enough to go out yet.”

“You said yet. That means there’s hope.”

“Maybe, but not this year.”

“Then make it your New Year’s resolution!”

“You mean make a resolution for me to go out next New Year’s Eve in that outfit? I couldn’t...”

“Why not? You could work on it all year. By next New Year’s Eve, you could be ready.”


“I think you should, Ray,” said Ashley.


“I’m not taking no for an answer. The dress and shoes are going into your closet. Make it your New Year’s resolution. You’re going to do this.”

“Alright,” said Ray. “I’ll work on the resolutions.”


While Ray didn’t have the same enthusiasm as his sister and Ashley, he thought it would be interesting to accomplish the goal. He started making a list. He thought about what he would do first to get started. If he was going to spend an entire night dressed as a woman, maybe he should start getting use to wearing women’s clothes more often. He only wore his sister's clothes in the apartment once or twice a week. He started his list.

My New Year Resolutions
Wear lingerie every day.
‘I guess I should also wear women’s clothes more often when at home,’ he thought.

Wear women’s clothes at home more often.

‘If I’m going to wear women’s clothes more often, I’m going to need additional outfits. Using what Karla is lending me will get old quickly. Getting my own wardrobe would be good,’ he reasoned. ‘That’s something I can do online.’

Purchase Women’s clothing.

Ray thought about the one thing that has kept him from going out dressed; he doesn’t look like a girl. While he didn’t have rugged features, he thought he looked too much like a guy. He wrote another resolution.

Watch online videos on how to apply makeup.

Ray read the list. This was good. If he got used to wearing women’s clothes and had his own wardrobe and could use makeup to be passable, he might feel confident enough to go to a New Year’s Eve party. He wondered if this could work.


Ray did not cross-dress on New Year’s day. His sister woke up as the parades on TV were ending.

“How was the party?”

“It was great. You would have enjoyed it. I wish you had come.”

“I was making my resolutions.”

“Speaking of that, let’s see what you came up with?”

“Here, I printed it out.” He handed Karla his list, and she began reading the list.

I resolve to:
Wear lingerie every day.
Wear women’s clothes at home more often.
Purchase women’s clothing.
Watch online videos on how to apply makeup.

“This is good for a start.”

“A start? I thought I was done.”

“The first one is fine, and I agree you need to purchase your own wardrobe,” she said. “But I’m changing it.”

“To what?”

“Purchase them in person. Knowing you, you were planning on online shopping.”


“Now for the makeup one.”

“Another change?”

“You need to take a class in person.”

“Really? You’re serious.”

“And there’s more.”


“Well, you need to remove the hair from your body. Then, as it gets closer to the New Year, go to a salon for your hair.”

“Anything else?”

“While you’re at the salon, get mani-pedi and finally go to a New Year's Eve party.”

“I can’t believe I forgot to add going to the party. “

“This is a good list. You should be ready to go to a party in that dress. I’m going to be gone for most of the year. You have all year to complete your list. You’ve got this. Don’t let me down.”

“I won’t.”


Ray was putting the last of Karla’s luggage into the cab. “That’s the last of it,” he said. The siblings shared a hug. “Have a safe trip and don’t forget to enjoy yourself.”

“That’s the plan,” she said. “Oh, here.” She handed Ray a printout of the picture she had taken of him dressed up. “I used my insane graphics skills to give you makeup.”

Ray looked at the photo and almost didn’t recognize himself. “Nice job. It must have been hard to make me look this good.”

“Not at all. All I did was use the computer to apply the makeup. I didn’t do any sculpting. That’s you with full makeup. This is to show you how good you will look when you learn to do your makeup.” Karla got into the cab. “I’ve asked Ashley to make sure you’re not stuck in the apartment, so expect her to call. I’ll call to check up on you. Bye.”


Ray was left to handle the list alone after Karla left for the cruise. Wearing the lingerie at home was not a problem. However, Ray could not yet walk into a store and buy women’s clothes, so he went online to add to his wardrobe. Karla wouldn’t know. He tried watching makeup videos, but the results were less than he wanted. His efforts never made him look like the picture his sister gave him. By the time July rolled around, he had given up on his resolutions.


“Jim and Alicia moved out last week,” said Ray on a call with his sister.

“What? I liked them. Did you find out where they were going?”

“He got a job in Delaware, so as soon as the lease was up, they left. They found an apartment there, and he had been living in it. That explained why I hadn’t seen him that much.”

“I hope whoever moves in is as nice as they were. What other changes will I find when I get home? Speaking of changes, how are things going with the resolutions?”

“Um… they’re going good. I’m taking it slow. I’m wearing things at home and slowing buying things.”

“You’re going to the stores, right?”

“Of course,” lied Ray. ‘At least I’m going to the store’s website,’ he thought. “I’m still looking for someone to give me makeup lessons.”

“Ask Ashley.”

“You told Ashley about the resolutions?”

“Of course. She knows about your, um, hobby and will help you if you ask. She has a friend who owns a salon. I’ll bet her friend will give you lessons.”

“That’s an idea. I’ll ask her about it.”

“Hey, I have to go. I’ll call next week. Bye,”

Ray sat there after the call. “I hope she’s not too disappointed,” he said to no one.


Mid-November came, and Ray was far from completing his resolutions. Even though he had told Karla he would, he had not asked Ashley for help. Karla would be home not much before Christmas. He didn’t want to let his sister down, but he didn't feel prepared to dress up and attend a New Year's Eve party. Sighing, he thought he would be another person who doesn’t complete their resolutions. He finished remotely fixing a network problem when his phone vibrated and he saw it was Ashley.

“Ray, is there a chance you can come over? I’ve got an important meeting I need to attend and my computer is giving me all kinds of screen problems. It’s a second interview for that job I’ve been after. Please say you’ll come and help.”

“Calm down Ashley. Of course I’ll come. I’ll bring my laptop. You can use my laptop to make the meeting while check your laptop. Let me grab it and I’ll be right over.”

“You’re a lifesaver. I’ll treat you to dinner if I get the job.”


At Ashley’s apartment, Ray set up his laptop so Ashley could join the meeting. While she was being interviewed, Ray determined the video driver had been corrupted. The virus program he ran was finishing as an obviously happy Ashley came into the room.

“I got the job! Thank you, Ray.” She hugged him and kissed him on the cheek. “How’s my machine?”

“It’s a bad video driver,” he said, recovering from the hug and kiss. “There are no viruses, so all I have to do is download the driver and install it. It’ll take less than fifteen minutes.”

“Great, then we can go to an early dinner.”

“You don’t have to take me to dinner, Ash.”

“I promised. It’ll be like a date. Let me freshen up and we can go when that’s finished.”

Ashley went to change while Ray installed the driver. ‘She said like a date,’ he thought. ‘Why would a girl like her want to date me? I like her, but she can have any guy she wants. A cross-dresser like me doesn’t stand a chance with someone like her. Still, we’re going to dinner and I can enjoy being with her.’

Ashley came back as the install was completing. Ray checked it was successful. “There you go. Good as new. You should keep up with the updates, you know.”

“It’s too much trouble. Now that I got the job, I can hire you to keep me up to date. You’ll give me a good rate, right?”

Ray laughed. “Of course.”

“Great. Let’s get to dinner.” She took his arm and led him out the door.


Ray and Ashley were finishing their dinner with a coffee.

“So, Ray, I haven’t been asking, but I’m dying to know, how have you been doing with your resolutions?”

Ray looked down at his coffee cup. “To tell you the truth, I’ve been letting them go.”

“You mean you’re not wearing…” Ashley looked around and saw no one with ear shot. “…lingerie?”

“No, and I have been buying clothes online. The makeup videos I watched didn’t help much. I can’t see me going to the salon for my hair or nails. I won’t be ready by New Year's Eve. The worst part is I feel I let Karla down. She wanted me to go out in that outfit. I feel awful.”

“You said Karla wants you to go out in the outfit. I haven’t heard you want to go out dressed up, do you?”

“I’ve been a closet cross-dresser since I was twelve and seldom felt the urge to go out dressed. Now, I kind of want to just to see what it’s like to get ready to go out, get dressed, get my hair and nails done, and do my makeup. Did Karla show you the picture she took of me last December?”

“She did. She’s amazing editing pictures.”

“Karla told me all she did was add the makeup, nothing else. If I could apply makeup correctly, I should look like the picture. I don’t even come close when I try.”

“You don’t want to let your sister down and it sounds like you would like to go out dressed, so let me help you.”

“Karla mentioned you knew someone who could give me makeup lessons.”

“I do, but I mean let me help you with the whole thing, all the resolutions. You’ve got about a month before your sister comes home. Let me help you work on your list.”

“I can’t ask you to do that.”

“Ray, you just helped me get a job I’ve been after. Let me help you feel confident enough to go out on New Year’s Eve.”

“I guess I could use someone to answer to.”

“It’s settled. We start tomorrow. Tomorrow evening, I’ll come over to see your list and we’ll make a plan.”


Ray answered the door the next day. “I hope you’re hungry. I made a chicken casserole,” he said as Ashley walked in carrying a large shopping bag.

“You didn’t have to make dinner.”

“I wanted to. My resolution list is on the table. Look at it while I take dinner out of the oven.”

Ashley sat down and examined the list. “This is good. There’s not too much to accomplish. I have some ideas we can talk about after dinner.”

They cleaned up after dinner and sat on the couch to go over the list. “I am going to assume you are wearing lingerie.”

“Yes, every day until New Year’s Day.”

“Let me see your drawer.”

“My drawer?”

“Yes, the drawer you keep you under things in.”

Ray lead the way and opened the drawer. Ashley opened the shopping bag she was carrying and began putting Ray’s male underwear in it.

“What are you doing?”

“I’m keeping these until after the new year. You won’t be needing them. Let’s see what is left.” Ashley went to Ray’s closet. “The second item on the list is to wear women’s clothes more often. Since we don’t have a lot of time, I suggest you wear them every day. Can you do that or do I have to take what’s in here too?”

“That won’t be necessary.”

“Good. This is a good start. But you need more clothes. Dress in something easy to take off on Saturday. We go shopping at eleven.”


Not having any male underwear made it easy for Ray to handle the first item on his list. He complied with Ashley’s request by dressing in his female clothing each morning. On Saturday, a nervous Ray sat waiting for Ashley wearing a pullover top, a pair of yoga pants and sneakers.

“You look nice,” said Ashley as she entered the apartment. “That’s great for shopping. Get your stuff and let’s get ready to go.” Ray left and came back carrying his wallet in his hand. Ashley sighed and muttered, "Oh, for goodness' sake." “Don’t you have a bag?”

“A shopping bag?”

“A handbag, a purse, a bag.”

“Oh. No. I’ve never gone out while dressed, so I never needed one.”

“Let’s see what your sister has.” They went into Karla’s closet and found a beige crossover bag. “This will do. Put your wallet in it.” Ray did as instructed. “Now let me fix your hair a bit and apply some makeup. I should be able to make you passable enough to go shopping.”

With hair and makeup done, Ray didn’t look like the picture his sister had manipulated, but he felt he was passable. They left for the stores.


Shopping was not as bad as Ray had expected. The lingerie section of the store was overwhelming. He was glad Ashley was with him. In the women’s section, Ashley told Ray she’d be back and Ray looked through skirts, tops and dresses by himself. He made his selections but waited for Ashley to come back before trying anything on. Ray was a little self conscious while looking for makeup, especially when the consultant asked him if it was his first time buying makeup. The consultant was professional and helped Ray get the right shades for his skin tone. She made a good commission with the sale. By the time they were looking for shoes, Ray was as much at ease as he could be. They put the purchases in the car and went to get lunch.

“Now that wasn’t too bad, was it?” said Ashley as they waited for their salads.

“No, it wasn’t. I thought I would die when the makeup consultant realized I was a man.”

“You had nothing to worry about. She wasn’t going to lose a good commission. Your homework is to go shopping during the week and pick up another bra and six more panties. You need to do it without me.”

“I should be able to do that. The makeup consultant showed me a couple of things to do. I should be able to at least look like this.”

“Makeup is next on the list. Next Saturday, we see my friend and get you in-person lessons.”


“I’m sorry Ray, I won’t be home until after Christmas. I feel so bad about missing Christmas with you,”
said Karla.

“We’ll celebrate Christmas when you get back. You’ll be back for the New Year’s Eve party, won’t you? Ashley and I have already bought tickets.”

“Wait! Does that mean you’re going?”

“I’m planning to go.”

“That’ll be the best Christmas present ever.”


Ashley took Ray to see her friend Sandy at her salon. Ray was nervous about going inside. Ashley made the introductions. Sandy walked around Ray as he sat in the chair.

“With the right shading and highlighting, I’ll make him more than passable,” said Sandy. “Here’s the plan. I will show you three distinct looks. The first will be your everyday look. The next is an evening look. It will be the look you use for a quick night out. The last will be for that special occasion when you want to look your absolute best. Then we’ll take a break and I’ll color and style your hair. Ashley, leave him with me and come back at closing.”

Sandy was still working with Ray when Ashley came back. Ray’s hair had been highlighted and styled into a feminine style that suited his face. His face was done in the special occasion makeup.

In the mirror, Ray saw Ashley arrive. Sandy turned the chair to face Ashley. “What do you think, Ash?”

Ashley was speechless. “You look amazing! Sandy, you’re a magician!”

“Have him here tomorrow. We’ll have the salon to ourselves and he can show me what he’s learned and after, I’ll do his nails and pierce his ears.”

By the time Ray was done the next day, he was confident he could create each of the three looks. He left the salon and went to dinner with Ashley, very confident he would go to the New Year’s Eve party in the dress Karla had bought him.


“I’m home!” yelled Karla as she walked into the apartment.

“Why didn’t you call for me to pick you up?” said Ray as the two siblings hugged.

“I wanted to surprise you. Oh, My God! I hardly recognize you. Look at you.” Karla held her brother at arm's length. “Your hair is so cute and did you do your makeup?”


“Is that a new top and skirt?”

“Yes. Do you like them?”

“Absolutely. You bought them at a store, right?”

“Yes, I did, in person.”

“I’m happy you stuck with it.”

“I have Ashley to thank. She helped me so much. Come on, your Christmas present is under the tree.”

“I have yours in my carry-on case. Let me get it.”


Ray opened the door as Ashley arrived on New Year’s Eve. “Ray, you look amazing! Are they new earrings?”

“Yes, my Christmas gift from Karla. You look great too,” said Ray.

Karla came into the room. “You look fantastic also,” said Ashley.

“Thanks,” said Karla

“We should get going. I rented a limo, and it’s waiting for us.”


Nervous at first, Ray soon began to enjoy the party. With minutes left until the new year, Ray found himself alone with Ashley.

“I need to thank you for helping me make my resolution come true.”

“I just gave you the nudge you needed. It’s me who should be thanking you for helping me fulfill mine.”

“Me? Why?...”

“Three… two… one… HAPPY NEW YEAR!” Suddenly, Ashley pulled him close and gave Ray a long, furious, hard kiss. Taken aback, a startled Ray looked questioningly at Ashley.

“You are so beautiful,” said Ashley, before kissing him again.

“I don’t understand,” Ray finally managed to say.

“Silly boy,” said Ashley, still with her arms around his neck. “Going out with you and taking you to this party was my resolution.”


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