How Bad Can It Be?

Me and my big mouth. Really, the only person I can blame is myself and said big mouth. After all, it was me who said ‘what’s so bad about a few hours in a dress?’ when my sister Izzy was complaining about mom signing her up for a mother-daughter tea party.

Calling Izzy a tomboy is an understatement. Growing up, I sometimes thought I had a brother instead of a sister with how often she’d borrow my clothes over whatever pink, princessy things were in her dresser. She all but threw a fit when she had to wear a dress to Thanksgiving the year we were five and I got to wear a sweater and ‘nice pants’. The following year, she dressed much more similarly to me, but it was like a switch flipped in mom. Come hell or high water, she was determined to turn her daughter into a girl. So, three or so times a year, mom would find a suitably feminine activity and force Izzy along. It never took.

This mother-daughter garden party was the latest battle in the war and so far, it seemed like no one was a clear victor. Normally, I would just hide out in my room, all too aware that mom would sometimes turn on me about my grades or the chores I was neglecting. Today, however, I was there. Fatefully there.

“Izzy, I bought you a lovely new dress.”

“Well, you can return it. I’m not going to some frou-frou tea party.”

“It’s more about socializing.”

“Mom! It’s the twenty-first century, that’s what the internet is for.” I watched this exchange, not really sure why Izzy made such a big deal out of it. After all, it was a few hours, right? Mom went into the kitchen to get water and to prepare her next line of attack and that’s when it happened: I, naive as ever, opened my mouth.

“What’s so bad about a few hours in a dress, Izzy?” I asked innocently. She turned and glared at me as if she did not even realize I was there.

“Fine.” She said. “You can do it.” I scoffed. Me? In a dress? Sure, it would be weird, but what better way to prove my point.

“Sure.” I shrugged. “I’ll do it.” There was no way mom would agree. She wanted Izzy to be the perfect daughter, not me. Izzy seemed to think she had scored a great victory, almost bouncing as mom returned with her glass of water.

“And another thing, Iz”

“Vicky says he’ll do it!” Mom looked startled. I glared at Izzy for using my much hated nickname and was about to fire back with her full name when Mom spoke.

“Victor, is that true?”

“Sure. It’s only a few hours in a dress, right?” This was all a joke. Mom would use my casualness to convince Izzy to do it.

“It is.” Mom’s pensive tone made me nervous. “And you two are the same size.” My eyes widened as she nodded. “Alright, I’ll go get the dress. Victor, you’re trying it on.”

Convinced this was some strange strategy for getting Izzy to agree, I followed mom to her room and stripped to my underwear. Why did it have to be pink, I thought? No, I was proving a point to Izzy. It was just a dress. Basically a long shirt. A sleeveless, pink, frilly, girly long shirt. I shivered as mom zipped it up and it tightened around me.

“This part is called the bodice.” Mom explained. “Is it tight?”

“Yeah.”

“Well, it’s meant to be form-fitting and it looks like it is.” She nodded. “This just might work.” She murmured.

“Think Izzy will agree once she sees me like this?” My question went unanswered as mom led me back out to my waiting sister.

“Looking good!” Izzy said with a huge grin. Emboldened, I strutted forward and did a twirl. Both Izzy and mom laughed.

“Obviously he’ll wear panties.” Mom said. “And you’ll learn how to walk like a young lady.” My grin faded as what she had said sunk in.

“What do you mean?”

“Well, you said it yourself that you wouldn’t mind wearing a dress. And no one there has ever met my daughter.”

“Mom, you” I paused and thought about it. “You know what? Fine. I’ll do it. Just to prove to Izzy that it’s no big deal.” It was hard to tell who was more surprised: Izzy or myself.

For the next few days leading up to the tea party, I practiced doing things like a girl. There was something bizarre about wearing a t-shirt and baggy basketball shorts while learning how to sit and hold my hands in a ladylike fashion. Izzy loved it, but I was too determined to prove my point to let it get me down. The day arrived and I traded in my boxers for panties with far more lace than I expected on them. Did girls really wear panties like this all the time? I couldn’t imagine Izzy wearing them, but I had never actually thought about her underwear before.

“Oh, you look great.” Izzy said, sitting at the dining room table in a tank top and shorts as I walked in in my dress. I faked a smile. “No twirl this time? Don’t tell me you’ve got cold feet. Or is it just the panties and your feminine modesty?”

“Don’t make your brother change his mind.” Mom said. She also wore a dress, though it was far more mature, and much less poofy, than mine. “Sit down at the table and I’ll do your makeup.” Izzy snorted into her cereal as I smoothed my skirt beneath me. “Izzy.”

I tried to hold still as mom did my makeup. My nose twitched, but I fought back the urge to sneeze with those brushes so close to my eyes.

“For the day, you’ll be your sister.” Mom explained once again to me. “I promise no one’ll ever know you’re a boy, okay?”

“Sure thing.” I murmured. I felt nervous, what boy wouldn’t, but at the same time, I was bound and determined to prove to Izzy that wearing a dress was no big deal, even for a boy.

All the same, I did draw the line at nail polish. Mom wanted to cover my nails in this almost violently pink nail polish, but I put my foot down and, given everything else I was wearing, talked her down to white. I winced just a bit as she praised me.

“You’re right! White to match the accents on your dress! Good eye, Victor.” If I had known then that that would be the last time I would hear my own name for – no, it was just a few hours in a dress. How bad could it be?

With my nails done and me nearly gagging from the chemical smell of the nail polish, Mom stood up and stepped back to take a good look at me. I felt ridiculous, but she nodded approvingly.

“Alright, I think we’re good to go.” I stood up and grabbed my phone off of the table. “Oh, that reminds me.” Mom grabbed a white leather handbag. “Put your phone in here. It’s the little details that’ll help us sell you as a girl.”

“Sure looks like a girl to me!” Izzy said.

“Not helping.” Mom said before leading me out to the car, but I swear she gave Izzy – the real Izzy – the slightest nod of approval..

It took a moment to tame my skirt enough to buckle up, but before I knew it, we were on the road.

“Until we get home,” mom said. “You’re Isabella.”

“Izzy?”

“The invitation came to Isabella, so that’ll be the name they’ll use at the tea party.”

“Is that the real reason Izzy didn’t want to come?”

“I didn’t even get that far with her.” Mom laughed. “And you volunteering threw me for a loop.” She smiled at me. “But we’ll have fun.”


As I followed mom to our table, I looked around. I had assumed, even though it was mother-daughter tea that there would be one or two boys. I was the only boy in sight, as far as I knew. It was a veritable sea of women. And every one of them wore a dress. These weren’t just girls. They were Girls. No wonder Izzy wanted out of this, I thought, clutching my little handbag that held my phone. Did they all see me for what I was: a boy in a dress?

"Here we are, Isabella." Mom said. The place in front of me had a little cream-colored card with my sister's full name, my name for the day, on it.

I pushed myself to smile. "Isn't this lovely?" I said, trying my best to make this all seem like no big deal. I would show Izzy, and have some fun doing it.

"Sit up straight, Isabella." Mom said in my ear. I complied, laying my hands on my skirt in what I hoped was an elegant manner. Everyone around me had to have pegged me for a boy, right? Then again, why was I so worried about making people think I was a girl?

Sitting there with nothing to distract me other than the boring speeches from the women who did this monthly, I was constantly aware of the feel of my dress and what I wore underneath. Boy clothes, especially my underwear, faded to the back of your mind, but girl clothes insisted on themselves somehow. I could feel the lace frills against my butt even when I was sitting perfectly still and straight. I should have brought something to change into for the ride home, I thought only a couple hours too late. Still, I was proving that there was nothing difficult about wearing a dress. I was a boy. A real girl like Izzy could easily handle this!



"Alright, ladies. Let's divide up for the social hour." The last speaker said.

"Mothers go there, daughters go there." Mom whispered to me. I hadn't realized I would be left to fend for myself.

I timidly made my way over to the girls. The other girls, I supposed. What did girls even talk about? Boys? Makeup? I had only worn makeup for the first time – and only time – today.

With how slowly I walked over, they had already formed into small chattering groups. I approached the one closest to me, confident that the way my dress brushed against my legs somehow gave my true gender away. The group moved slightly to allow me to step in.

“I haven’t seen you here before.” One of the girls said. She wore a navy dress and had a purple streak in her hair that made me wonder if she was a tomboy like Izzy. “Hi, I’m Claire.”

“I’m… Isabella.” I wished I had practiced a girl voice. I nervously looked around the group, waiting for the inevitable ‘he’s a boy!’

“Nice to meet you, Isabella.” Claire said. “That’s a nice dress.”

“Thanks. My uh”

“Your mom picked it out?” One of the other girls said. “Welcome to the club!” They all laughed and I felt as if I was part of the group. I breathed a sigh of relief, once again returning to my old confidence. Even when the girls talked about boy bands, I had heard girls in my class talk enough about them that I was able to more or less hold my own.

Even involved as I was in conversation, it was difficult to forget who I really was: a boy in a dress. The way the girls moved seemed so effortless and I felt like a klutz trying to mimic them. I must have done pretty well though because no one ever figured out that ‘Isabella’ was really a boy. What had Izzy been so scared of? I was proving my point and then some!

The end of the event arrived and I had to join the ‘other girls’ in hugging and saying goodbyes.

“See you next month, Isabella!” A few of the girls said and I fought the urge to say I might be a different girl by then.

“Ready to go, Isabella?” I breathed a sigh of relief as I followed Mom out of the room, to the car, and back, I thought, to my own clothes. “All buckled?”

“Yep.”

“How'd it go?”

“I don't think anyone knew I was a boy.” Mom smiled.

“Good, good. So you enjoyed yourself?”

“I think I proved to Izzy that it's not so bad.” I laughed. “But I'm kind of eager to get out of this dress.” Mom nodded, her face hinting there was something I did not know.

“We're almost to the hotel.” She said after a moment of contemplation. My heart tried to stop and leap into my throat at the same time. Hotel?

"A hotel? Mom! What am I going to wear?" I tried to remain calm. After all, mom was not really going to make me stay in a dress for forever.

"We'll figure it out. Let's get to the hotel first, Isabella." I stared down at my skirt, nervous once again. What did I have to be nervous about though? There was no way mom would keep me in dresses for forever. I shifted slightly to try to calm myself down, but then I felt the lace frills of panties on my butt. Heck, I’d keep the dress on if I could at least get my boxers back. Every second we drove, we got farther and farther from my boxers– and my boyhood.

I stood behind mom as she checked us in, fidgeting with the dress. Suddenly, faced by this unknown, I felt conspicuous and uncomfortable in the dress. Mom had said we would figure it out. I tried to breathe.

We got into the elevator and it climbed to our floor. A man stood by us and was about to get out when he saw we needed that floor as well.

"Ladies first." He said, smiling at me. I murmured a thank you and followed my mom. She slipped the keycard into the door and we walked in. My jaw dropped as who did I see sitting on the bed but Izzy!

"Well, hi there! You look even prettier than when I saw you this morning."

"How?"

"Took the bus." She said with a grin. "Don't worry, I packed enough clothes for both of us!" I sighed in loud relief.

"Thank god! I can't wait to get jeans on again." To say nothing of proper underwear, I thought, even then feeling the lace frills on my butt and the lace tickling my thighs. Her smile changed slightly.

“Well, I brought jeans for me. I have other options for you."

"Options? I repeated, puzzled. She was the same size as me, that was the whole point of this whole strange ordeal. "Mom, Izzy's being weird!"

"Isabella, don't tattle. Izzy, be nice to your sister."

"Isabella? Sister? Mom, what's going on?"

"I meant I brought pajamas for you." Izzy explained. "You didn't bring them, right?" She smiled at the small handbag I was holding still.

"No." I admitted. Something seemed fishy.

"Thank you, Izzy. That was very responsible. Thank your sister, Isabella." I smirked at her out of habit, but realized she meant me.

"Mom! What is going on?"

"I told you in the car. You are Isabella until we get home. Now quit yelling, young lady, and thank your sister for bringing you pajamas. It's not ladylike to sleep in just your panties, even when it's just us girls." She frowned at me. "Now."

"Th-thank you, Izzy." This was all getting more and more confusing!

"Anything for my sister." Izzy said, clearly loving every minute of it.

"Are" I tried to think of some sneaky way that would not get mom–or Izzy–to start on another ridiculous comment about how I was a girl until we got home. "Are the pajamas like the ones I wore last night?" Izzy shrugged.

"I don't pay attention to your clothes." She grinned. "But I know you'll love them, Isabella."

"That's what I'm afraid of."

"Isabella, don't mumble at your sister. You were so pleasant and polite at tea, why slip into bad habits now?"

“I” I stammered. I had to get out of there, to breathe, to do something other than stand there dumbly. “I need to pee.” I hurried into the bathroom, locking the door behind me. What was I going to do? I jumped as I saw a girl in the mirror before realizing she was me. Here I was, standing in a hotel bathroom in a dress, hardly even able to recognize myself! The worst part was, I knew I had one thousand percent gotten myself into this.

"What's so bad about a few hours in a dress?" I asked my reflection mockingly. "How about a whole freaking day in a dress?" I sighed and, hiking up my dress in the most boyish fashion I could manage, peed. Even so, I knew I had to make sure my dress was just so before I could rejoin my mom and sister in their jeans. That’s right. While I was holed up in the bathroom, mom had changed, leaving me, the only boy, the only one in a dress! "Can I change?" I asked, already knowing and dreading the answer.

"No, Isabella, we have plans." Mom said.

"You look fine. You don't need to put on a different dress." Izzy added. There was not even a mention of my dumb comments that had gotten me into this. In their eyes, I had completely become Isabella, the girly one. Izzy smirked as she handed me the white handbag. It was only then that I remembered my phone was in it. I took it and she snickered. She could keep her phone in her jeans pocket, after all.

I tried to ask what plans they had made while I was hiding, but they told me it was a surprise. They stood on either side of me in the elevator as if they were my bodyguards. I could not believe how feminine I looked with them in their jeans and t-shirts beside me. I tried to find consolation in the fact that if I could barely see the boy I was, no one else could. Heck, I had even infiltrated a room of nothing but women, even girls my own age, and passed without a hitch. I almost felt like a secret agent until mom broke the silence.

“Isabella was a perfect lady today, Izzy.” Didn’t she realize how weird it was to have two daughters – yes, I’d accepted I was pretty much her daughter for the rest of the day – with the same name? Then again, wasn’t there that boxer who named all his kids the same name?

“That’s great. I hope that means you two will be invited back next month.” I glared at her.

“Come on, girls.” Mom gave me a smirk that showed Izzy wasn’t alone in how much fun she was having. “The salon’s just down here.”

If standing in the elevator in a dress while my sister and mom walked around freely in jeans was bad, the salon was worse. I had to sit right in between them as the three of us got our nails done. I thought my fresh paint job from that morning would suffice, but apparently not! Since I was in a dress, it felt to me like they paid me extra attention, making my nails especially shiny and feminine. In truth, it was probably because they had to do more work reshaping my boy nails into the ten pinnacles of femininity I stared at as mom paid the nail technicians.

“Smooth your dress out, Isabella.” Mom said. I did it without even thinking. Would I ever get back to being a boy? I knew I was being silly. After all, how much more could they have planned?

I feared that the next stop would be some dress shop or something else where they could force me to live life as a girl, but instead, we stopped at a tea shop and had a light snack. I even got to fish my phone out of my handbag and catch up on my old life, though learning to swipe the screen with shiny pink claws took a little getting used to.

“Should’ve gotten him fake nails.” Izzy mused. I glared at her, but how upset could I be? This was the first acknowledgement of my masculinity all day.

“Girls, put your hands in the middle of the table. I want to take a picture of our new nails.”

“What pretty daughters you have!” An older woman said.

“Thank you!”

“Isn’t it amazing how different sisters can be?” She smiled. “Would you like me to take your photo, ladies?”

“Oh, please!” Izzy said, already throwing her arm around my shoulder. I smiled, hoping we would go back to the hotel soon.

After tea, we walked around the park until my feet hurt. Even then, I had to hobble back to the hotel, but at least we got to sit down for dinner. Mom had a glass of wine and began to join more and more in giggling with Izzy every time the server called me Miss. Thankfully, the server did not seem to catch on. How could he, I thought as I eyed my reflection. A whole day and my makeup still looked flawless.

“Can I take this dress off now?” I asked the moment we were back in the hotel room.

“What’s wrong? Regretting opening your”

“This was a lot more than just a few hours in a dress!” I exploded. “I’ve been wearing this all day! There’s no way you would have put up with this” I brandished my nails at her. “And you know it.”

“Stop arguing.” Mom said. We were not arguing! “You agreed to be Isabella until we get home and we’re holding you to that.”

“But”

“But Izzy, you absolutely need to thank Isabella for letting you off the hook.”

“Uh, thanks.” I glared at her.

“Isabella, what do you say back?”

“Mom!” She had to know that I was not actually a girl. I’m her son!

“Now.”

“You’re welcome.”

“You can take off your dress, Isabella. Izzy, can you grab your sister her pajamas?” I snarled in frustration. Mom knew I had no choice but to play along. What new torment was Izzy about to pull out of the bag?

At first glance, they were the same as boy pajamas, only aggressively pink. It was a shirt and pants, but the shirt buttons were shaped like little white hearts. I even had to sleep like a girl. Still, pants were pants. Mom nodded in approval.

“Isabella, go put those on. Here, I’ll unzip you.” She reached over and I felt like I could breathe again. I had stopped noticing the tightness of the bodice, but now I realized in retrospect it had been squeezing me all day. “Come back out here and we’ll remove your makeup.” I could not believe I felt relief to be changing into pink and white pajamas, but it was what it was.

The pajamas were made of cotton, but they felt infinitely softer than any pajamas I had ever owned. Come to think of it, the p- underwear I wore was the same way. It only meant that even after the lights were off and I could no longer see the pink pajamas, I’d know I was wearing girl pajamas. I sighed.

“Pants are pants.” I said, even though these seemed to hug me in strange ways and flow a lot more down around my ankles. Flow femininely, I thought with distaste.

I emerged from the bathroom and could not decide which would be worse: if they had laughed or the fact that they didn’t. I forced a smile as mom patted the desk chair by her bed, positioned right in front of the mirror.

“Sit here, Isabella. I’ve got plenty of makeup wipes here.” I sat down and she handed me the peach colored package.

“Huh?”

“A girl your age should be able to handle it herself.” She said. I practically bit my tongue to keep from commenting on how far she was taking this. Izzy snickered from the bed and I could not help but notice she was wearing a pair of gray shorts and an old t-shirt that I was almost certain had once been mine..

“Izzy, why don’t you pick us a movie to watch?” Mom said as I opened the package of makeup wipes and set to work. Wiping off my makeup at least made me feel less like a girl. Did Izzy even wear makeup? I had no clue. Up until this morning, I had never even thought about that side of the world of girls.

Mom ended up coming over and helping me and soon enough, I sat on the bed with Izzy, watching some ridiculous romantic comedy. Mom and Izzy both seemed to love it, so I made due.

“Who do you like, Isabella?” Izzy asked during a commercial.

“Huh?”

“Beau or Ian?”

“I dunno.”

“Come on. You’re only a year younger than me. Surely you’ve started noticing boys!”

“I’m proving it’s not so bad wearing a dress, not that I want to be a girl!” I said. If I had not been sharing a bed with Izzy, I would have gone to bed right then and there, if only to get back to boy clothes that much quicker.

“Izzy, be nice to Isabella. And you, young lady, be nice to your sister.”

“Hasn’t this gone a little far, mom?”

“Just be happy I’m not taking pictures of my two beautiful daughters.”

“Mom!” Izzy and I said in unison, though we were objecting for very different reasons.


Morning came and I practically jumped out of bed. It was time! Back to boy clothes, to boxers and jeans and t-shirts and no pink whatsoever. Sure, I had one pair of boxers that were pink plaid, so maybe Izzy had brought those as a joke, but I’d take that over my pink pajamas and the lacey panties underneath! In a heartbeat.

Izzy refused to let me touch the suitcase and that was my first clue that this ordeal was not over yet. Ordeal? I had made it hours as a girl. Izzy would have no defense at all the next time mom tried to make her into a ‘proper young lady’. I had won.

All the same, I felt my stomach drop as she revealed the outfit she had brought me.

"I told you, sis." Izzy said as if she loved seeing me wince. "I packed the best clothes for you.”

"And she really did make a lovely choice, Isabella." Mom said. To their credit, the dress was not as bad as the one I had worn all day yesterday, but it was yellow. Not just yellow, but brilliantly so, all but guaranteed to make me stick out and draw the eye to my femininity. How had this been hanging in Izzy's closet?

"First things first," mom said. "Underwear." My brain had a brief disconnect between what it thought of as underwear and the panties mom handed me. By this point, I felt like an old pro at forcing a smile as I carried my outfit for the day into the bathroom to shower and get dressed.

Even something as everyday – well, theoretically everyday at least – as a shower brought new revelations. I did not have nails anymore, I had claws! Try as I might, I kept scratching myself as I tried to at least rinse off, refusing to use Izzy’s or mom’s – whoever’s! – body wash. I would take a proper shower, with my own stuff, at home!

I emerged from the shower with a single-minded purpose. No rest stops, no sightseeing, we were going straight home! I calmed down a bit as I dressed. After all, I had to consider the opportunity I had here. “I did twenty-four hours” or near enough. “In dresses, Izzy. It’s really not that bad.” I knew it was a lie, but maybe, if I just faked it for the trip home, it would help me prove my point.

Taking a deep, stabilizing breath, I walked out and even did a little twirl. Izzy snorted like she always did, but Mom seemed a little too pensive for my liking. Once Izzy had disappeared into the bathroom for her shower, practically flaunting the jeans she would be wearing while her brother wore a yellow dress, mom sat me down.

“I think we’ll go no makeup.” She said. “Unless you want.” It was a gauging question. I laughed.

“No way, mom! I’m counting the seconds until I can put my clothes back on.” She nodded.

“Well, I think we can all agree you proved your point to Izzy.”

“But seriously, mom!” I said, whining a bit. “Isn’t this all a bit much? I mean, I agreed to a few hours in a dress, but”

“It didn’t kill you. In fact, you got a lot of very nice compliments, Isabella.” I sighed.

“We are going straight home, right?” Mom nodded and I clung to that bit of hope. It was nearly over.

Sitting alone in the backseat as Mom and Izzy chatted up front, I practically expected us to make a stop. I even tried to think of what girly thing they would subject me to next, staring down at my glossy pink claws. I almost gasped in surprise when I saw our house and my sweet freedom.

My bedroom isn’t really what I would call super masculine, but it felt that way as I ran into it in a dress. With the door closed and wisely locked, I allowed myself to celebrate my release from a dress. It felt so good, so right, to finally step into a pair of boxers. Sure, my underwear from yesterday morning was right there atop my hamper, but that felt like a lifetime ago. Finally. Finally back in boy clothes. Boy underwear, a boy shirt, boy jeans. I looked at my hands. Those were not a boy’s hands. I headed downstairs.

“We had a lovely time, Victor.” Izzy said. “Shame you had to miss out. Maybe Isabella will tell you all about it.” I stuck my tongue out at her before getting down to business.
"Uh, mom? How do I get rid of this?"

"That was an expensive manicure. You're keeping them."

"They're just pretty nails." Izzy said with a smirk. "What's so bad about having pretty nails?"