A Well-Planned Christmas Vacation

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December 2021 Christmas Holidays Story Contest Entry

Thanks to Malady and sangreall for corrections and valuable input for this story.

A Well-Planned Christmas Vacation

by MonicaS

Christmas was always the time for a family gathering for as long as I could remember, and this year was no exception. So early on Christmas Eve, we drove the four hours to my grandparents' farm. I sat in the back of our car next to my 17-year-old sister, Olivia. I was 16 years old and named Daniel, but everybody called me Dan. In front of us sat our parents, Paul and Linda.

Olivia was dressed for the occasion in a sweater, a short skirt, pantyhose, and boots. I couldn't understand how she always preferred beauty over comfort. I wore a hoody and my well-used sweatpants and planned to change into the mandatory nice clothes once we arrived.

We would be staying for 5 days, so I packed my game console to play games with my cousin John once the main event was over. We could even play some ball as the weather was supposed to be good enough. I liked to hang out with him and avoid the girls. The girly stuff just wasn't my thing. All in all, I had nice plans for my Christmas vacation.

Just before noon, we arrived at the farm. I helped Dad with unloading our luggage.

"Where is my suitcase?" I asked when I noticed it was missing.

"Huh? All 4 suitcases are here," he replied.

"None of them are mine."

"Then who's suitcase is this?"

"That's mine," Olivia answered.

"We are only here for a few days, and you brought 2 suitcases?" Dad asked.

"I couldn't decide what to take with me. And there's enough space in the car," my sister responded.

"Hmm, okay. Well, I took all the suitcases in the living room, and there were only 4. So Dan, where did you put your suitcase?" Dad then asked me.

"I ... I must have left it in my room," I answered dejectedly.

"That puts you into quite a predicament. What will you wear?"

I realized that driving home to fetch my suitcase wasn't possible. Going shopping that day wouldn't be feasible either, so I replied, "Um, I could just wear what I have on and buy stuff after the holidays."

"Hmpf, you're not wearing that for the holidays!" Mom exclaimed.

"I could borrow something from my cousins," I said.

"That wouldn't work. Ben and Henry are much bigger than you, and John is smaller," Mom responded. "But Olivia is about your size. And as she has packed generously, she won't mind lending you something, I'm sure."

"But Mom, I can't wear Olivia's clothes. I would be a laughingstock."

"The family will understand. And it's time that you learned to be more responsible and that actions have consequences," Mom insisted.

I might have forgotten something or left something unattended before, but the consequences were minor until now.

Olivia smirked and said, "Aren't you lucky that you aren't bulky, have a cute face, and can't grow a beard? With a bit of makeup and a wig, you should make a convincing girl."

"That's decided then," Dad announced.

I stood there with my mouth open. I couldn't believe my family wanted to turn me into a girl. I expected them to start laughing at any moment and to declare it a hoax. But that didn't happen. Instead, Dad said, "Come on, let's go into the house. We don't have that much time before lunch, and you'll probably need ages to get ready."

* * *

We were the first guests to arrive at the farm. So we greeted the residents, my grandparents James and Maria, Uncle Jason, Aunt Maria, and their 3 children, Henry, Ben, and Cynthia.

"I don't understand the youth today," Grandma scolded me after the greetings, "In my time, we wouldn't dare slouch like that."

"Don't worry, Maria," Mom replied, "He'll change. Actually, he'll change a lot as he forgot his suitcase and has to borrow Olivia's clothes."

"Ohh, how precious, another one," Grandma replied.

"What do you mean, another one?" I asked.

"Oh, nothing," she replied, "I'm curious how you'll turn out as a girl. You could be quite pretty."

I wondered why everybody wanted to see me as a girl. "I don't have to become a girl just because I wear Olivia's clothes."

"That would be quite incongruous," Grandma said and frowned. "Seeing a boy in a dress might be a bit jarring."

"But I am a boy," I exclaimed.

"Sure, but you don't have to look like a boy. Actually, I insist that you'll try to look the best you can. It's Christmas after all, and everybody will put effort into their appearance."

"Is there no other option?" I asked.

"None of the men is your size, and I won't tolerate your sloppy clothes," Grandma replied.

"What will the others think?"

"That you're a good sport and make the best out of a lapse. We're all family after all," Grandma said.

Grandma could be quite stubborn, and it was hard not to do as she wished. It didn't seem like I could avoid getting girlified. It wouldn't be the end of the world, just some clothes and stuff. I sighed, "Okay, I guess."

"Ohh, I didn't play dress-up with somebody since I was little," Cynthia chimed in. "We'll have so much fun. Let's get you ready."

There went my plan to avoid the girls. And my game console was in my suitcase too, of course. Fortunately, my presents were in a separate bag.

* * *

Olivia and I followed Cynthia into her room. She was the same age as me and had a typical girl's room with white furniture and pastel-colored decorations. In one corner was a makeup table with a mirror and a lot of brushes, tubes, and color palettes. I dreaded being at the receiving end of them.

"Let's see what we have to work with. Can you strip to your underwear?" Cynthia asked.

I hesitated. My sister had seen me in underwear often, but it was different with my cousin.

"Oh, come on. I have 2 brothers. I have seen it all," she said to encourage me.

Reluctantly I stripped to my boxers and tank top.

"Okay, not very bulky or hairy. The leg hair should be okay with pantyhose. Let me clean up the chest," Cynthia declared, and before I could really react, she plucked a hair with tweezers.

"Ouch, that hurt!" I exclaimed

"Oh, don't be a wuss. Beauty knows no pain," Cynthia replied and quickly plucked 2 more hairs. "There, now a low neckline is okay."

"Who said I want a low neckline?" I asked.

"You have more choice now," my cousin replied. "Olivia, can I see what you brought? Perhaps I have something too."

In the next few minutes, many clothes were held against me and either rejected or put on the 'maybe' pile. I was actually asked for an opinion too. All the pants were too tight for me, so only dresses and skirts were left. Then it was time to try something on. I selected a long-sleeved sweater dress and pulled it over my head. It fit well as it was stretchy.

"I think I could wear this," I said.

"Hmm, it's a bit shapeless, but we can add a belt and create some fake breasts," Olivia replied.

"Mom has a waist cincher that should work. I'll fetch it," Cynthia announced.

I removed the dress again after my sister told me so. Then she put a bra on me and filled it with socks. It was a strange feeling, both physically with the straps quite noticeable and emotionally. While the dress could be seen as a very long sweater, I crossed a border with this very feminine item. This is a costume, just like a Santa costume would be, I told myself. No matter what I wear, I'll still be a boy underneath.

Olivia came back with an elastic waist cincher and a wig. I put the cincher on and removed perhaps 2 inches from my waist. Then I put the dress on again, and my sister added a belt. I looked at myself in the mirror on Cynthia's closet, and if I ignored my head, I actually looked like a woman.

"Not bad," Olivia declared, "but you have a slight bulge where it doesn't belong. You should be able to get that under control with some tight panties."

She gave me a pair of plain panties, and I contemplated what it meant. When I thought about getting into a girl's panties before, it definitively wasn't about wearing them. It's just a costume, I told myself again and went into the bathroom to change into the panties. I adjusted my parts so that the tight fabric indeed prevented the bulge.

Once I was back, my sister gave me a pair of opaque black pantyhose and showed me how to put them on. My black sneakers were unisex enough to wear with the dress. That completed my outfit.

"Now it's time for the makeup," Cynthia said.

"I'll only go along with it if it looks good," I stated adamantly, "otherwise, it all comes off again. I don't want to look like a clown."

"Don't worry," my sister replied, "I know about looking like a clown. I have to cringe when I look at some of my old photos. I now go by less is more."

So I sat on the stool in front of the makeup table, and Olivia and Cynthia went to work. They actually explained a lot and let me choose between options. For example, I could use mascara like Olivia or fake eyelashes like Cynthia and decided on the fake eyelashes.

I could watch the whole process in the mirror and saw how my male face was feminized a bit with each step. After Cynthia added the wig, I definitively saw a girl's face looking back at me. A pretty girl's face even.

"What do we call you now?" my sister asked me. "We can hardly call you Dan now."

I hadn't thought about that, but it seemed reasonable.

"You could just feminize your name to Dana," my cousin suggested.

"Hmm, yes," I decided. "That's nice and simple."

I stood in front of the large closet mirror again to take in the complete look. It was an odd feeling to see me as a girl. I hadn't expected such a convincing result. I even struck some poses which made the girls laugh.

"You might need to practice that a bit," my sister said and gave me some tips.

After a while, my cousin said, "I can understand that you love looking at your new self, but I think it's time to face the family."

I blushed at that.

* * *

The remaining parts of the family had arrived while I was getting feminized and were sitting around the huge dining table. The newcomers were Aunt Ruth and her husband Willam with their son John and Uncle Edward with his new girlfriend, Angela, and her 2 children.

"Hello everybody, let me present you my new sister, Dana," Olivia introduced me.

"Oh, I didn't know you were transgender," Uncle Edward said.

"I'm not transgender," I replied. "I just forgot my suitcase and had to borrow some clothes, and only skirts and dresses fit. So it seemed prudent that I go the whole way. Olivia made a joke that I'm her sister, I'm still a boy. But you can call me Dana if you want."

"You are very pretty, Dana," Angela said. "I wouldn't have guessed that you were a boy. I'm Angela, and these are my children, Stacey and Kim."

Stacy looked very androgynous with short hair and no makeup but quite a soft face. The clothes were unisex too, so I was unsure if Stacy was a boy or a girl. On the other hand, Kim was a stereotypical girl with long hair, makeup, and a red dress. Both looked to be about my age.

While I made my round shaking hands, I noticed John eying me conspicuously. Well, it was understandable. He was 2 years younger than me, and we always hung out together at family gatherings. Our other male cousins, Ben and Henry, were 18 and 20 years old already. And the girls were, well, girls. And now it seemed like I joined their rank, and he might end up with the adults.

After Uncle William shook my hand with disdain in his face, he commented, "I don't understand you. How could you let yourself get dolled up like that? Don't you have any self-respect?"

I never liked Uncle William. He was too stuck up and conservative, didn't really fit into our family. I goaded him even more with, "I think the girls did a good job. Don't you think I look pretty?"

He was aghast and responded with "Pervert."

"Yeah, I like you too," I replied and went on to shake hands with Aunt Ruth. She looked shocked about her husband's outburst and apologized for him.

I finally arrived at John and sat down next to him. "Don't worry," I told him, "I won't abandon you. We boys have to stick together, don't we?"

"It's not that," he replied.

"Yeah, I get it. I don't look like a boy. But it's just a costume. It doesn't bother you, does it?" I asked.

"No, you look fine. Actually, I ... I," John started but then stopped.

The awkward situation was saved by the announcement of lunch.

* * *

"Do you want to join us in my room?" Cynthia asked me after lunch. "It's much cozier there."

"I don't want to leave John alone," I replied.

"Could I perhaps join too?" John asked. I was a bit surprised as he never seemed to be interested in girly stuff.

"Sure," Cynthia answered, "the more, the merrier."

So all the adolescents moved towards Cynthia's room.

"Stacy, I still don't know if you're a boy or a girl," I said after we were settled in.

"Is it that important?" Stacy asked back.

"Um, no, I guess not," I replied. "It's just that in most cases, you can see at first glance if somebody is male or female. And you're an exception to that rule."

"Did you look into a mirror lately?" Kim asked and smirked.

I blushed and answered, "Okay, you got me there. But even though I'm a boy, I'd rather look like a girl than in-between."

"Well, I guess we're different then," Stacey said. "Okay, I'll tell you my situation. I was born and raised as a girl and was generally fine with it. But lately, I've felt a lot of pressure to conform to society's norms for teenage girls. Especially boys constantly asking me out, having to look pretty, and other sexist bullshit. I'm trying to escape it by looking androgynous, and it's working mostly. I don't feel that I'm a boy, so I don't think I'm transgender. But I don't feel like a typical girl either. So I'm perhaps non-binary, somewhere in-between. I'm somewhat testing it out by using they/them pronouns on the net."

This started a discussion about pronouns, non-binary, transgender, and gender stereotypes. I learned quite a bit.

I noticed that John asked some questions about transgender treatment and that Kim was quite knowledgeable there. Additionally, I caught him looking intently at me a few times.

"John, what is it? Is something wrong?" I asked.

"Um, nothing," he replied.

"Come on, get it out," I demanded.

"It's so unfair."

"What's unfair?"

"You are so pretty and don't even want it," John exclaimed.

"Huh?" I was confused.

"John, do you want to be a girl?" Kim asked.

"Yes," he answered after a pause.

"Oh," was all I could say.

The others weren't as flabbergasted and bombarded John with questions. He visually shrank back.

"Girls, stop it," Kim demanded, "we're scaring him. John, don't worry. We mean no harm. Just tell us what you want to, don't feel pressured."

All eyes were on John, and nobody said anything for a while. "I don't know," he eventually got out. "I always felt that I should have been born a girl, but when Dad caught me in Mom's clothes, he made it clear that's not acceptable. So I tried to suppress it."

"But you always played ball with me. I never had an inkling that you wanted to play with dolls," I said.

"Well, I never had a doll. Perhaps I would have liked playing with them. On the other hand, I like to play ball. Girls can play ball too," John replied.

"What do you want to do now? We could help you dress up as a girl like Dana," Cynthia suggested.

"I think I would like that, but I'm afraid of what Dad will do then. He already complains a lot about my long hair," John said.

"Yeah, he didn't react well on me dressing up," I agreed.

"But we will all support you," Cynthia said. "And you could start with something subtle, a bit of makeup perhaps. I know boys who wear makeup."

"They are probably gay," I retorted.

"So what? What's bad about being gay? And you are wearing makeup too. Does that mean you're gay?" Cynthia countered.

"Um, no, I'm not gay. But Uncle William might think John is gay if he wears makeup," I replied.

"Or he might think we just goofed around," Cynthia argued.

"Okay," John said suddenly. "But only a little bit, nothing glamorous."

"Don't worry," Cynthia reassured him, "I can do an everyday look."

So my cousin started on John's face, first using concealer to hide a few blemishes. His skin was fair enough that Cynthia didn't need foundation. She then worked on the eyebrows, followed by subtle eyeshadow and mascara. Cynthia finished with nude lipstick. To complete the look, she styled John's hair in a more feminine way.

Each part of the makeup was very subtle, but the combined effect shifted the appearance from boy to girl. John smiled when he saw the result in the mirror.

"I don't see a boy with makeup," Kim stated. "Do you have a female name? I think it would be more fitting."

"Um, Emily," John replied.

"Would it be okay if we call you Emily?" Kim asked.

"Only among us girls. I don't think I'm ready to come out to Dad. Let's pretend you just goofed around."

"Welcome to the girls' club, Emily," Kim announced and hugged her. "Only Stacy is left now. Do you want to stand out, Stacy, or will you embrace your feminine side for a while?"

"Hmm, okay, I guess it's only family and no boys to fend off. Cynthia, do your worst."

So Cynthia gave Stacey a glamorous makeover. Gone was the ambiguity. She was a beautiful young woman, appearing to be quite a lot older than before. This completed our girls' club, something I never planned to be a part of.

We continued with other stuff. I sometimes watched Emily. I had made a mental switch and saw her as a girl now. It wasn't only the face. I noticed feminine mannerisms and speech patterns too. Her clothes were quite unisex, so that didn't destroy the impression of a girl either.

* * *

Eventually, it was time for dinner.

"Do you want to keep the makeup, or should we remove it?" Cynthia asked Emily.

"Um, I want to keep it," she replied. "But remember to call me John."

We returned to the dining room, where everybody smiled when they saw us parade into the room except for Emily's father.

"What's this now? Did they corrupt you too?" Uncle William asked his child.

"We were just having some innocent fun," Kim replied, "and we didn't want John to feel left out."

"I can't condone this! This isn't natural," my uncle retorted.

"Calm down, William. Don't destroy the festive mood. It's just some makeup," Grandma admonished him.

Thankfully he kept quiet after that, and we had a pleasant meal. Emily started a bit shy among the adults but eventually warmed up and chatted and laughed like any girl.

* * *

After dinner, we stayed with the adults until it was time to go to bed.

Grandma explained the sleeping arrangements, "The 3 girls sleep in Cynthia's bedroom, the 3 boys sleep in Ben's room, while Ben and Henry sleep in Henry's room."

3 boys? I wondered if she was confused and thought Stacy was a boy. I looked at the others and noticed Kim roll her eyes and shrug.

I borrowed some pajamas and toiletry from Olivia and went to Ben's room. I was surprised when Kim was there with Emily.

"Kim? What are you doing here?" I asked.

"Well, I was born a boy, so I assume your grandmother wants me to sleep here," Kim answered.

"You were born a boy?" I was flabbergasted. She was perhaps the girliest of us all.

"Yeah. Actually, I still go to school as a boy. But I spend a lot of time as a girl. I use the label genderfluid or bigender," she explained.

"Why didn't you say that when we were discussing transgender stuff?" I asked.

"I didn't think it was important. I usually don't mention it as it makes it easier to be perceived as just a girl," Kim replied.

"Well, you're certainly a beautiful girl. I still can't imagine you as a boy," I stated.

"Me neither," Emily agreed, "You are soo pretty. And your voice is feminine too."

"Thanks," Kim said. "I guess I'm still young enough that I can pull this off. I'm worried about puberty, though."

"Huh? You should be through most of puberty", I said. "I had my voice change two years ago already, for example."

"I'm only 14," Kim replied. "I had some changes, but nothing drastic yet."

"Oh, I thought you were 16 like me."

"Yeah, that's actually my goal. I mostly hang out with Stacey's age group, so I adjusted my style. Many thought we were twins before she started the androgynous style."

"I guess makeup has quite an effect. I saw it with Stacey," I said.

"Yes, I'm quite proud of my skills there. I got into some trouble because boys thought I was older, but that is a story for another time," Kim said. "It's time to get ready for bed, I think."

So we all went to remove our makeup and change into nightwear. Even without makeup, Kim was all girl in my eyes. The nightgown and long hair probably were partly responsible. Emily still remained on the girl side of the gender divide, too, helped by the borrowed nightgown and the feminine hairstyle. Perhaps it was more than just how they looked. I was definitively a boy, though, even in women's pajamas.

* * *

The next morning we gathered in Cynthia's room before breakfast.

"So, how did you like wearing makeup yesterday?" Olivia asked Emily.

"It was nice. It felt right to look like a girl and to be seen as a girl too," she replied.

"If it just wasn't for your Dad," I remarked.

"Screw him. This is my life," Emily stated adamantly. "Actually, I'd like to try the complete look, full makeup and a dress. Just like Dana did yesterday."

"We can do that," Cynthia said. "Does that mean you want to live as a girl now? We'll support you no matter what you do. You could live with us if needed."

"Thanks, that means a lot to me," Emily said, reassured. "And yes, I think I am a girl, and I want to live as one."

We all agreed to help her to come out to the rest of the family.

So we got ready for the day. It was sometimes a bit cramped with 6 girls simultaneously trying to look the best for Christmas Day. As Cynthia and Olivia were busy helping Emily find something to wear among Cynthia's old clothes, I tried to do my own makeup. It didn't turn out so well, so I was glad when Kim offered to help me. In the end, we were all in skirts or dresses and glamorous makeup, even Stacy, when we were called for a late breakfast.

Wearing a dress and makeup didn't bother me that much anymore. The family's reaction except for Uncle William had been good, and I wasn't the only physical boy in a dress. The last day gave me some insight into a girl's life, and I didn't regret spending time with the girls. Actually, Stacy seemed to be more uncomfortable.

As expected, Uncle William wasn't pleased when he saw Emily.

"This goes too far! No son of mine is parading around in women's clothes! Go change immediately and remove all that gunk, too," he demanded.

Emily shrank back at that outburst.

Cynthia came to her rescue. "Well, then it's good that you don't have a son, but a daughter, Uncle William," she retorted. "So she has no need to change."

"What is this idiocracy? Of course, I have a son," my uncle replied.

"What she means is that John is transgender," Kim explained. "that John may have a boy's body but feels like a girl on the inside."

"Actually, it's now she and her name is Emily," Olivia added.

"John, is that true?" Aunt Ruth asked.

"Yes, Mom," Emily replied.

"Oh Honey, I never noticed. Why didn't you say anything before?" Emily's mother continued.

"I was afraid. But yesterday it all came together, with Dana dressing as a girl and talking about gender and wearing makeup," Emily answered.

"This is all wrong," Emily's father exclaimed. "You've corrupted my son. John, I'll show you what it means to be a boy, to grow into a man. We'll leave this mess behind and go home right now."

"No, we're not leaving," Aunt Ruth countered. "John, I mean, Emily? That is what you want to be called? I don't know much about being transgender, but no matter what, I will always love you, and we'll go through this together."

"We'll support you too, Emily, won't we?" Grandma added and looked at the rest of the family for confirmation.

"Of course," multiple people said at once.

"Welcome to womanhood," announced Angela. "I happen to know a bit about being transgender, thanks to my children. So if you have any questions, you can ask me."

"You're all in this together!" Uncle William shouted. "You liberals don't let boys be boys but turn them into effeminate wimps!"

I was shocked. My opinion of Uncle William was low anyway, but this? "I'm everything but not a wimp," I replied, "and Emily isn't either. Do you know how much courage is needed to stand up against a tyrannical man like you? And we liberals don't turn anybody into anything. We just let them live the way they want to live."

"Says the boy who got put into a dress. This just isn't natural. I'm through with all of you. Ruth, you either come home with me now, or you don't need to come home at all," my uncle said.

"Fine, I'm staying," Aunt Ruth replied, seemingly shocked too.

"Okay, that's it then. My parents were right. I should never have married you," Uncle Willam said and stormed off.

We were all speechless, perhaps hoping that Uncle William would reconsider, but it wasn't long before the front door closed with a bang and we heard a car leave.

"Oh Ruth, I'm so sorry," Grandma tried to console her daughter and hugged her. "You know my opinion about William, but even I didn't expect this. I never wanted your marriage to end like this."

"It's all my fault," Emily said while weeping. "I should have kept this to myself. Now, Dad is gone because of me."

"No, Honey, this is only your father's fault. You didn't do anything wrong," her mother replied and went over to her new daughter to hug her. "It's probably for the better. I might have ignored our problems for too long. If he really loved us, he wouldn't issue an ultimatum and then just leave."

"What will we do now?" Emily asked.

"Don't worry, we'll manage," Aunt Ruth reassured her daughter. "Mom, can we stay a bit longer to sort the mess?"

"Of course," Grandma answered. "I'd love to have my daughter back at home and to get to know my new granddaughter. You can stay as long as you want."

Just then, my stomach thought it was an appropriate time to complain about being empty with a loud grumble.

"We'll work something out, but it seems we have more pressing needs," Grandma said. "Let's start breakfast."

* * *

There was a subdued mood at first, but eventually, it cleared up. Nobody in the family really liked Uncle William. We were only sorry for Emily and her mother.

Aunt Ruth was actually quite composed. She even took part when we announced mostly light-hearted reasons why she's better off without Uncle William.

We girls were more concerned about Emily, though.

"Hey, we can have soo much fun together," Cynthia tried to cheer her up. "I can teach you how to do your makeup. We can go shopping together. I can tell you all the gossip. And I can introduce you to the important people if you go to school here."

"Changing schools gives you a chance to start fresh," Olivia added. "So everybody would only know you as Emily."

"You don't have to be afraid of your father anymore," I pointed out.

"My Mom and I researched a lot about transgender treatment, so we can help you there," Kim contributed. "As I said yesterday, you can stop puberty, so you won't grow into a man. With female hormones, you can instead grow into a woman."

"And if being girly ever is too much for you, I can show you alternative ways to live," Stacy said. "You don't have to do any of the things Kim told you about."

"But if you do want to be girly, I have a lot of old clothes that should fit you, so you have a headstart," Cynthia concluded.

"Okay, okay, I get it. It's not that bad." Emily conceded.

"Hmm, don't you like it to be a pretty girl in a pretty dress and to be accepted as a girl?" Kim asked.

"Yes, but ...," Emily started.

"No buts. Just enjoy that for now. It's Christmas, after all. The start of a new life. Enjoy your first day as a girl," Kim continued.

"Okay, I'll try," Emily said and even smiled a little when she looked down at her dress.

* * *

After breakfast, we sat around the Christmas tree in all its glory with the presents under it and sang some Christmas carols. Emily was a bit reluctant at first but eventually sang along. I had some trouble singing with the girls because my voice didn't reach high enough. But it didn't really matter as we all were in a festive mood.

Then it was time to open the presents. I got the usual boy stuff, a game for the console I wanted to take with me, for example. But I also got a thin necklace with a dolphin pendant from Cynthia.

"Thank you, it's pretty," I said, "but I don't think I'll get much use out of it."

"You can wear it now, and who knows when you'll have an opportunity again," she replied and winked.

I didn't plan to repeat my foray into girlhood, but my plans didn't work out that well lately. It was a nice necklace, so I put it on as suggested.

There had to be some last-minute changes with the presents for Emily. She got quite some items more appropriate for girls while some gifts for the other girls were a bit odd, probably originally meant for John. Emily got very emotional about it and thanked the gift-givers profusely. I thought it was very nice of them to show their acceptance of Emily in that way. Unfortunately, I didn't think of that as my gift for Emily was an official soccer ball from the last championship.

"I'm sorry that it isn't appropriate anymore," I said when she opened the packaging.

"You doofus. Just because I'm a girl doesn't mean I won't play soccer anymore. So thank you for the ball. We might have to wait until we are out of these dresses before we use it, though."

I blushed because of my faux pas. But at least one part of my plans could still work out.

Opening the presents made everybody happy, and we almost forgot Uncle William except when the presents for him were left over at the end.

"What do we do with them?" Mom asked.

"According to me, you can burn them," Aunt Ruth answered.

"It would be a shame to destroy something that's totally good," Grandma replied. "But I don't see William appreciating the gifts if we ship them to him. So I suggest to open them and to distribute them among us."

We agreed, and I got a pair of socks out of it. Too bad I'm not a house-elf, then I would be free.

* * *

The presents occupied us until it was time for a light lunch. After that, the girls' club convened in Cynthia's room again. Cynthia offered all her old clothes to Emily, and our task was to get them from the attic and go through them to see what could be used by her. Emily chose from those items what she liked and even tried some on. It took some time, but in the end, she had a base of clothes to build upon.

"I still can't believe this is real," Emily said. "Just yesterday, I had this big secret and didn't know what to do about it, and now I have a path to become the girl I was meant to be. Thank you all for your support."

Later we had dinner followed by some more singing. We stayed with the adults until it was time for bed. The sleeping arrangements were the same as the day before.

Soon I was lying in bed, pondering the day. Except for the hiccup before breakfast, we all had a nice Christmas Day.

Emily seemed to enjoy life in her new role. She was quite talkative and laughed with the other girls while she didn't say much and rarely laughed as John. This "being born in the wrong body" must have been quite hard on her. Wearing makeup and girls' clothes together with an outlook on a future as a girl was like a switch had been turned.

I contemplated my situation in comparison. I spent the last 2 days in the wrong gender role, just like Emily did all the years before. But I didn't have a problem with it. I knew it was only temporary, just a costume. It was actually a bit fun to play a role and look the part. I shuddered at the thought of doing this long-term, though.

* * *

The next day started with girlifying Emily and me again, but with casual clothes and simple makeup. Stacy had enough of presenting as a girl and was back in her androgynous look, so she was the odd one out.

We had spent most of the day in Cynthia's room when the sun came out in the afternoon.

"We should get out and enjoy the nice weather," Olivia suggested.

"What do you want to do, take a walk through the fields?" I asked.

"We could test my new soccer ball," Emily replied.

"Sure, but what about our clothes? They're not really appropriate for playing ball, and we might get dirty. And what about the other girls?" I asked.

"We can play soccer too," Cynthia retorted. "I have some training clothes, and if something gets dirty, we can wash it."

The others agreed, and so we changed. I put on my only male clothes, the hoody and sweatpants I wore on the drive to the farm. I removed my wig but didn't bother with my makeup. That put me into a state between girl and boy, just like Stacy. I wouldn't like to meet other people like that, but we'd only be on the lawn behind the house.

The girls were much more competitive than I expected, and I had to make an effort to gain an advantage. All went fine until I slipped and fell onto the lawn. I wasn't hurt, but my aging sweatpants ripped open. We had played for quite some time, so we called it a day.

In the evening, Emily sat down with her mother to plan their future. They decided to take the offer to stay with the family and that Emily would not return to presenting as a boy. With the current laws, she should be able to attend school as a girl. It was a big change, but after spending 3 days as a girl, Emily was adamant that it was the right way.

* * *

The following day started like the day before, until the girls wanted to go shopping. With my male pants destroyed, I only had the choice to stay behind or to go as Dana.

"I don't think I can go shopping dressed as a girl," I said. "It's one thing with only family present, but I'm afraid what others will do when they recognize that I'm a boy."

"You look very convincing," Kim argued. "Just keep your voice down, and nobody should notice. And even if somebody thinks you're a boy, why should they do anything?"

"And if somebody tries anything, we'll protect you, little sister," Olivia added.

After a bit more prodding, I gave in and agreed to accompany the girls.

* * *

My fears turned out to be unfounded. I only noticed questioning looks directed towards Stacy, and that was it. Nobody said anything.

The main reason for the shopping trip was to complete Emily's wardrobe, so we spent all the time in the women's sections of the shops. At first, I was only watching, but then I looked for items suitable for Emily, too.

"What do you think about this?" I asked when I showed her a tartan skirt. "I think it's cute."

"I got something similar from Cynthia already," Emily replied. "Besides, it looks too large for me, but it should fit you. Since you like it, you should try it."

Before I could say anything, I was escorted to the changing booths. Well, I was dressed as a girl already, so what harm could it do?

The skirt actually fit, and it looked good on me. It was on sale, so the girls convinced me to buy it. And as I couldn't wear just a skirt, a top and some underwear were added to my pile. I wouldn't need any of the items after the next day when we'd go home, but the shopping bug must have bitten me. And it wasn't much money.

A bit later, we were in a shoe store. Besides sensible shoes, Emily also tried some heels.

"How do you manage to walk with those spindly heels?" I asked.

"You can try for yourself," Olivia replied. "Let's find you a pair."

There was no way to stop my sister, and she got me a pair of shoes with 3-inch stiletto heels in my size. They fit well, and after standing up, I balanced in them well enough. Walking was a different thing, and I was a bit wobbly. Not really elegant, but at least I didn't break my ankle.

"You need some practice, but you seem to manage fine," Olivia commented. "You can start when we get back."

In for a penny, in for a pound.

* * *

True to her word, Olivia made me change into my new heels when we arrived back at the farm. She gave me some tips and made me walk up and down the room. When I had enough of that, the girls had me fetch some items throughout the day to get me to walk some more. It worked, as I was a lot more stable by the end of the day.

The next day I wore my new clothes together with the heels. It was strange how quickly I got used to female attire, even managing my own makeup, but that day was my last day as a girl. It certainly was an unusual experience. With Emily, Kim, and Stacy also bending the gender rules, I never felt alone. Actually, I felt much closer to my sister and cousins than before. Also, my crossdressing prompted Emily to say something so that she got out of her misery. That alone was worth it.

When it was time to go home, I noticed that I had forgotten to get new pants. So I had no choice but to stay in my attire. I remembered how I thought about Olivia wearing a skirt and pantyhose on the way to the farm. Now I wore the same on our way back home. Yeah, the Christmas vacation went just as planned.

The End

* * *

Cast:

  1. MC's family:
    • Dan: 16, MC
    • Olivia: 17
    • Paul & Linda: parents
  2. John's family:
    • John/Emily: 14
    • William & Ruth: parents
  3. Kim&Stacy's family:
    • Kim: 14
    • Stacy: 16
    • Edward (stepfather-to-be) & Angela (mother)
  4. Cynthia's family:
    • Cynthia: 16
    • Ben: 18
    • Henry: 20
    • Jason & Madison: parents
    • Maria: grandmother
    • James: grandfather
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Comments

With the title of a well

With the title of a well planned christmas it makes me wonder did Dan forget to bring his suitcase down or did Olivie substitute it with her extra one.

That would be very mean,

MonicaS's picture

and it's Christmas. I don't have siblings who would do such things, so I never thought in that direction.

Greetings,
Monica

What a Fun Story

I never had that much fun with my cousins :-(

Janice

You need some luck

MonicaS's picture

You need the right people and the right circumstances. This all wouldn't have happened if Dan hadn't forgotten his suitcase.

You've got my vote

Iolanthe Portmanteaux's picture

... for the Christmas story contest. It's nice to see everything work out.

- io

Thank you

MonicaS's picture

I'm happy that you like it.

MonicaS

The softer side

It was great that Dan got to experience the female side, it will make him a better person for it. And what he also learned is to plan ahead and make sure his stuff makes it into the car, on the plane, whatever. Oh, just realized this story is "Lost Luggage" all over again except told from a teenager's point of view. Good story.

>>> Kay