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Life in the city

Author: 

  • Punk Job

Organizational: 

  • Title Page

Audience Rating: 

  • General Audience (pg)

Life in the city


By Punk Job

TG Themes: 

  • Accidental
  • Androgyny
  • Real World

TG Elements: 

  • Shopping
  • Slice of Life

Life in the city - Chapter 1

Author: 

  • Punk Job

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Accidental
  • Androgyny
  • Real World

TG Elements: 

  • Shopping
  • Slice of Life

Permission: 

  • Posted by author(s)

It was my first week in the city, I had just turned 17, and since I wanted to go to college in the city, my family thought it was best for me to start getting used to living there a year ahead and I enrolled in an online high school program for my last year, it wasn’t a big deal for me since I didn’t have more than 1 close friend, Eliza, who I knew since we were 5, and pretty much didn’t care about anyone else in my school. They arranged for me to rent a room in the house of my mother’s friend Carla who lived there, she was just divorced and her daughter Leah was already living on her own so there was plenty of space for me to stay. It was my lifelong dream to leave the little town and come to live in the city so I was in a state of pure excitement that whole week, if not the month.

Carla picked me up at the airport, and as we drove to the house she gave me the basic house rules of the house.

“I don’t want to be a pain to you Dan, and I don’t want you to be a pain for me, so I won’t be intruding much with what you do, as long as you follow some basic house rules: No loud music, tv or anything loud while I’m in the house, you have to clean your dishes, if you arrive late, don’t make noise, and please try to not arrive drunk, never leave the house unlocked and please don’t lose your key, if you arrive late and don’t bring your key you’ll sleep on the street because I won’t wake up to open the door for you, I know some rules may sound too obvious but I have already dealt with teenagers and I know that the obvious slips right through you at this age, If you follow rules I may allow for a party whenever I have to travel out, also I have a cleaning lady coming twice a week, she can do your laundry, just leave it in the basket that I left in your bedroom”.

I just smiled and promised I was going to follow rules, and that probably I would never need to throw a party since I’m not the party kind of guy.

The house was pretty big for the city that was mostly filled with apartment buildings, it had 2 floors, 3 bedrooms, and a backgarden, it was on a quiet street just 4 blocks away of the main avenue of the area, so it was a pretty neat accomodation for a guy that was in love with the city. Carla showed me my bedroom, it was the one they normally used for visitors, then she showed me her daughter’s bedroom which was connected to mine through the shared bathroom, since Lucia, her daughter wasn’t living there anymore that wasn’t going to be an issue unless there were visitors, Carla said.

“It’s that really all you luggage?” Carla asked amazed while looking at my small suitcase.

“Yes, my dad said it was better for me to buy new stuff here, because of the weather difference, so I just brought a change of clothes, some books and small stuff”.

“Oh my god, I’m so not used to that “boys” mentality anymore, if it were me or my daughter we would have packed the entire house” She said laughing “I hope, you do get to buying new stuff, because I don’t want to be smelling you after wearing the same outfit after a week or more”.

We both had a laugh, she seemed to be easygoing, wich made me feel relaxed. She then just left to work, gave me some advices about the public transportation and nearby parks, malls and places to hang out, it was a full month before I would begin the online classes, so there was plenty time for me to enjoy the city at full, so I decided to relax at first and lay on bed, I started scrolling through instagram and facebook, seeing what my friend and everyone else back in town where doing.

Flash forward two days later, I had barely left the house, and those few times was to go across the street to look for snacks, I wasn’t aware that I could actually miss town, but I did and I couldn’t stop scrolling through photos and posts of everyone I knew, I spoke a while with Eliza, we both missed each other, I lied a bit to her, saying I had already been everywhere and met some cool people, when reality was that I had only met Carla’s daughter once, and Sandra the cleaning lady this morning.

Suddenly out of nowhere came Leah marching through my door, she made direct eye contact and exclaimed “You’re getting up, and I’m going to take you to the store so you get your new clothes and actually see real people”.

I was paralyzed, I had barely talked to her when Carla introduced us, and since she was older (26) and way too hot, I really didn’t think we were going to bond in any way.

“My mom says that you haven’t left the house and Sandra just told me you’re wearing the same thing you arrived in, so you better get up and come with me, or I’ll never give you a chance again to hang with the coolest girl in the city” she added while getting closer to the bed.

I just nodded, which made her crack laughing.

“You got a long way to guy Dan, if you plan to make it in the city, you can’t be the shy town boy anymore”.

“I won’t” I finally replied, and got up in a jump.

“That’s the attitude!” she said and took me by the arm, almost crawling me through the house, to the street, the day was super sunny without any cloud, and since I had spent all day inside I immediately squinted my eyes.

“Put these on, you’ll look cool” Leah said as she put a pair of sunglasses on my face.

image3.jpg

We got in her car and she started driving.

“So you’re missing your friends?”.

“Not really, well not in plural, i just have one friend”.

And so we started talking about my town, and she told me all the stories her mother had told her about my mom when they were young, and how she had always envied her mother about having such a great girlfriend when she was younger, while Leah never had a close girlfriend.

“I do have my girl gang, you know, but it’s nothing like what our moms had, they were almost like sisters, then our fathers came, then job, then your family moved and rest is history, so now you and I must get along, I’ll give up on getting a close girlfriend as long as you come up to be a good guy to hang out”.

“I’ll be a good guy” I just laughed.

“Ok, then I might introduce you to some pretty girls” she said and turned to wink at me.

Leah was really cool and outgoing, I was thankful she took me out of bed, and made such an effort to make me have a good time and forget about my town. We spent all day together, she took me for brunch to a hipster place, then she took me for clothes, I was too shy to try stuff in front of her, so I just rushed picking up stuff and paid”.

“Really?” she said “That’s why you don’t have any style you just took the first things up and didn’t even took a real look at the store”.

“I just want the basics, that’s all”.

She rolled her eyes, and then we moved on to a ice cream shop, we walked along the avenue eating our ice creams and talking about life, she had just got out of college adn was an intern at a fashion magazine, her dream job actually was more serious journalism, but that was all that she could find, and it was with help of her mom’s business partners that she got that job, so she was trying to make the most out of it, I told her about how I wanted to be a scriptwriter and/or novelist, and she encouraged me to follow my dream, we talked about the city, and how I imagined it would be, she told me that all that was true, but it also wasn’t as great as I made it out to be, she promised to take time later in the week to take me out and show me more of the city and meet new people.

“Ok Dan, so here’s your stop, see you later, you’re a nice guy don’t hide on that bedroom”.

She said as we reached her mother’s house.

I came to my bedroom with my bag of new clothes and threw them on the bed, to finally try them on, I started with a white button shirt.

image4.jpg
It seemed alright

Then, a pair of jeans, these ones took a while to come up, a black t shirt.

image1.jpg
Ok, this ones are way too tight for me

They didn’t come out easily, so I just left them on, while I tried another white shirt, I hadn’t noticed it was a V neck, and for my taste it was way too long a V neck.

image2.jpg

Then hit it me, these were women’s clothes.

Life in the city - Chapter 2

Author: 

  • Punk Job

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Character Age: 

  • Teenage or High School

TG Themes: 

  • Androgyny
  • Tricked / Outsmarted
  • Voluntary

TG Elements: 

  • High heels / Shoes / Boots / Feet
  • Shopping

Permission: 

  • Posted by author(s)

I wanted to die, it was all my fault for rushing through the store without taking a better look, I went through all I the clothes trying to find which ones where the most manly of the bunch, if Eliza were here she would be laughing so hard at me, these are the kind of dumb things that always happen to me when I try to act cool, it always somehow comes back at me, making me look like like a fool, I was at least glad that Leah hadn’t found out or she probably would also had laughed at me, in her mind I was still cool, or that’s what I wanted to believe.

I picked up the clothes that looked more androgynous, thinking I could pull off wearing them until I went to buy new ones, I was in the middle of doing this when Carla came to my room.

“Heard that someone finally got out of this room” she said as she came in.

Fuck, I thought. I was still wearing the V neck shirt, hope she doesn’t notice it.

“And you got new clothes it seems” she said checking me out “It’s not what I thought your look was, I hope Leah didn’t push you into buying something you didn’t want”.

I’m pretty sure she thinks these are boy’s clothes.

“Not at all, it was all me, I just picked up the first things that I found on the store” I replied confident that it was androgynous enough to pull it off

“Well they look nice, I guess that’s how the kids your age are dressing now” she said taking a closer look “I’m out of touch with your generation”.

I laughed “Nah, I’m sure you’re more in touch with my generation than my parents are”.

That comment made her laugh.

“Well I’m glad you finally got out, I hope it becomes a habit” She said. “Goodnight Dan”

She left the room. I was almost sweating in nervousness, I wasn’t really sure if she really thought these were boy clothes or if she has just assumed I was into girl’s clothes.

I arranged all the new clothes and got to bed, hoping the next day I could make a trip to the store and return at least some of them.

Knock, knock

I was barely awake as I heard the knocks on my bedroom door.

“Come in” I said, thinking it was Sandra coming for my clothes.

I was wrong, Leah came in with two coffees in her hand, she came to sit on the border of my bed and gave me one of the coffees.

“What time is it?” I asked, still sleepy and confused.

“Time to wake up Dani” She said as she insisted with her arm for me to take the coffee.

I sat, and took the coffee, it was too early for me, mostly since I had gotten used to staying asleep longer than it would be normal. I sipped the coffee.

“So, I got an intersting call from my mom last night, and since I didn’t have much to do this morning I decided to come here and see for myself what was she talking about” Leah finally said.

I almost fainted, wishing it was still a dream, or more accurate a nightmare.

“And what are you referring to?” I said trying to act cool.

“Ok Dani, if you’re going to act cool about it then I’m going to assume that you didn’t made a mistake and that you actually like wearing women’s clothes, is that what you want me to think?” Leah said going directly to the point.

“It was a mistake!” I said way too loud.

She chuckled, and then came up to my closet.

“And you tried to act cool in front of my mother, while wearing women’s clothes” She said as she inspected the new clothes.

“I did” I shyly replied. “I kinda thought some might actually be for both boys or girls” I added, one more time trying to be cool about it.

“Some of them yes, I think” She said while holding out the jeans her mom caught me wearing.

“Put these on” she said as she handed them to me.

15 minutes later I was showing her how I was dressed when her mom came in last night. We both laughed about it.

“Damn, Dani, you really can pull off the androgynous look, I’m starting to think you should actually keep some of these” Leah said while sipping her coffee.

“I don’t think so Leah” I said while staring at the mirror.

I noticed a smirk on her face

“Dani?” she said. “What is your shoe size?”

I was confused about why would she ask that, or mostly I was too dumb and naive.

“I’m not sure, whichever size it’s around 9 inches” I said

“We’re the same size!” she said as she stripped of her heels. “Please try them on” she said almost in a purr.

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5 minutes later, of course, I was wearing the outfit with her heels.

Life in the city - Chapter 3

Author: 

  • Punk Job

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Androgyny
  • Tricked / Outsmarted
  • Voluntary

TG Elements: 

  • High heels / Shoes / Boots / Feet

Permission: 

  • Posted by author(s)

Leah was having a blast watching me change outfits, which made me enjoy doing it, It never felt like she was making fun of me or something like that, it was more like a bonding brother and sister thing for me, so I kept showing her how all fitted me. We were having a fun time.

“Dani, you really can pull off that androgynous look” Leah said at some point, “I work in fashion and I can tell you that it’s one of the most popular trends right now”.

“Really?” I asked amused.

“Yes, androgyny is coming up big this year” Leah said. “Maybe you should keep the clothes and go for that kind of look, you know? It will probably make you look more interesting to the girls in that hipster college you want to attend”.

I laughed at the comment about the college.

“I don’t know, I don’t think I’ll be comfortable wearing such skinny jeans, and women’s blouses, and I’m not really a fashion forward kind of guy” I answered.

“Well, you could be if you want to, I mean it’s not like you’re wearing a dress or skirt” she said while shrugging.

I turned to look at her, “I’m wearing heels!” I said while pointing at my feet.

She cracked laughing.

“And you really have turned out to be good with them” She said almost impressed “When I first wore heels I could barely stand up, you’re a natural kid”.

“Shut up!” I said as I sat on the bed to take them off.

“Oh come on!” she said putting her arm around me and making eye contact with me.

I had began to notice that she was very good at making me pay attention and feel comfortable when she made eye contact.

“Can I do one more small thing before you take them off?” Leah asked kindly.

“What is it?” I said, sure that I was about to say yes to anything she said.

“Let me put makeup on you” Leah said with a smirk.

It was hard to say no to her, I had been in the city only 4 days, and she was the closest thing I had to a friend, even with the almost 10 years gap between us she was the closest person to my age I had met here, and she was actually cool I really enjoyed being with her, it was like an instant connection, as if we were meant to be friends from the start, some weird connection that was passed from our mothers to us.

“Ok, whatever” I said.

Once again trying to act as cool as possible about it, as if didn’t actually care, and now that I think about it, I really didn’t care, she made me feel confident.

She smiled instantly and hugged me, then she took a couple of thing from her purse and started by putting a band on my head to keep away my hair.

“Since we’re not the same skin tone, I’m only doing a little bit to your eyes and a touch of color to your lips, something that pops out, natural yet feminine”.

I laughed and shook my head at the feminine comment. She came close to my face and started doing my eyes.

“This is mascara, it will make your lashes look darker, and longer, this helps to make your eyes look bigger, you notice it in mine?” She said as she blinked twice for me to notice her lashes.

Then she took a little thinking as she looked inside her purse.

“Mmmh I don’t know” She said almost to herself.

Then she looked back at me and pursed her lips.

“What is it?” I asked.

“I’m unsure about your lips, I don’t my lipstick suits you”.

She was wearing light matte pink lips. Suddenly she seemed to figure it out.

“I know, wait here, I should have a better one in my old room” She said as she ran across my bathroom to her old room.

I was intrigued as to what she wanted to do, or even why, but in the end I was actually having a good time and it didn’t seem as a big deal at the moment, it was all in the sake of having a little fun. She returned with a small box full of products.

“These is some of my old makeup” she said “I used to wear more when I was younger, now I have toned down my look a bit, but I think you’ll skin tone goes perfect with red lips”.

And as she said that she took out a pencil.

“This one is perfect, now open your mouth a bit” she said as she did with her lips the open mouth expression she expected me to do.

I followed her instructions and she began applying the lipstick, it had a creamy texture, my lips suddenly felt smoother somehow.

“Oh my Dani! You look so cute” she said.

She grew a huge smile, she looked as if she was watching the most cute puppy you could imagine.

“Haha, stop it, and let me see” I said.

I’m sure I was flushing because of the attention.

“Here come to the mirror” she said.

I followed her to the mirror, and I was amazed, it was still me for the most of it, but I actually looked kind of cute, she was right red suited me.

“So what do you think” Leah asked.

“I love it” I said without giving it even a thought.

Screen Shot 2018-09-19 at 16.16.38.png

“Haha, you’re so cute Dani” She said as she watched me, perplexed to how comfortable I seemed to be with the whole situation.

There it was, she finally seemed to have the perfect girlfriend and little sister she had always wanted.

Life in the city - Chapter 4

Author: 

  • Punk Job

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School
  • College / Twenties

TG Themes: 

  • Identity Crisis
  • Real World
  • Voluntary

Permission: 

  • Posted by author(s)

That day Leah took me to buy a few more clothes, guy clothes, but convinced me to keep some of the women’s clothes, the ones she said looked more genderless. In the end I didn’t mind that much about it, she was making me feel as if I was way too cool for not being too apprehensive about letting her put makeup on me or wearing her heels, that I ended up feeling more confident and actually being cool about it.

The weeks passed and I got used to go out more often, I would walk to a park that was close to the house, sometimes I would bring a book and just sit down to read, I had a reflex camera so sometimes I would walk around taking pictures of city sights. At first Leah would come around the house once or twice a week, and she would take me out to some cool restaurant or café, she took me to a couple art galleries, and a couple of times we just stayed at home watching a movie and talked about her internship, the goals we had for our careers and life.

“It’s funny, I think I have such an easy life, and yet I don’t make the most of it” Leah said.

“What do you mean?” I asked back.

“Well, since my parents divorced, my father has done everything to over compensate, I could ask for almost anything I would have it” she said “My car, my apartment, everything that’s in it, and I don’t pay for a thing, so I can work an internship and not worry about money”.

She shook her head, and threw herself back to my bed.

“That’s why I can’t do more serious stuff, I don’t struggle” she said with her eyes closed.

“You seem to be struggling right now” I said, trying to help.

“Yes! My daddy’s girl problems” she said irritated “Ugh I sound so dumb”.

I couldn’t help but laugh, which provoked her to throw a pillow at me, hitting me right on the face.

She came up quickly

“I’m sorry, I threw it a little too strong”

I just laid my hand on my cheek which hurt a little.

“Nah, don’t mind, it’s nothing” I said

She stood and came up to me and hugged me.

“I’m really sorry” she said as she batted her eyes next to my face, and started to put pressure on the hug.

She had started getting used to treating me as a little puppie or something like that, she sometimes said I was her little baby bro or sister, she switched it on occasions, I actually liked to be treated like that so I didn’t complain, it was nice also to have her as a somewhat older sister or brother, I mean she sometimes was a bit rowdy so that could count as brotherish behavior, but mostly she was cool, kind, and too funny to even complain about anything. We certainly bonded quickly.

“You know what?!” she said excited “We should go out tonight”.

“What?” I asked a bit excited.

“Yes, to a club” she said “Some girls from the magazine are going tonight to a new club that sounds cool”.

“But I’m underage” I said shyly.

“It doesn’t matter, I have been going to clubs since I was 16” she said “With just a bit of makeup all girls can do the trick”.

As she said this she was already going across the bathroom to her old bedroom, I started following her, a bit nervous and confused, but also kinda getting more excited, it was a weird feeling forming inside of me, it was taking over me. Leah went directly to the closet and started looking for outfits, she took a couple of dresses out, she took a look at herself at the mirror holding one of the dresses in front of her, then she took me to the mirror and did the same thing with the other dress.

“What do you think?” Leah said.

The feeling had taken over me, I was too confused about it, my stomach felt weird and I felt kinda dizzy, I wanted to play along but I was scared, my head was cloudy, it felt like adrenaline but in a bad way, suddenly a glimpse of memories came around, from when I was younger, a day when my dad was mad at my mom because she let me buy a doll at the toy store, then a day at my friend Eliza’s house, we were too young, like 7 or 8, her older sister painted Eliza’s nails, and I asked her to paint mine too, her older sister laughed at me saying that was gay, then the day that Eliza was having a sleepover for her 13th birthday and I wasn’t invited because I was a boy, I remember that I cried that night and that my parents got in a fight because something I said about it, there were several flashes, random memories of moments I had forgotten and that still seemed somehow cloudy.

“I’m a boy Leah” I said quietly.

Suddenly I was hyperventilating, It seemed as if I was about to cry, I probably was about to cry actually. Leah looked at me scared, I was having a breakdown and she could tell, she hugged me, as I froze there, she was warm, she seemed worried.

“We can do something else” Leah said quietly while stroking my hair.

I just stared at the mirror, at the dress Leah had just dropped to the floor. Where did all this came from?, I had completely forgotten about that stuff, It didn’t came back that last time Leah made me wear women’s clothes and makeup, it was as if it was triggered by the dress, the moment, or something else I wasn’t aware of.

“It’s ok” Leah said quietly “It’s all ok, Dani”.

She stroke my hair, with one hand and hold me to her body with the other hand. My mind was getting more calm as I took a few deep breaths. Leah could feel I was getting better.

“Are you alright, Dani?” Leah asked.

I was coming back to the moment, to the excitement, to the reality and getting rid of the memories again, yet I was confused about this feeling, it all came out of nowhere.

“Yeah, I’m alright I think” I finally said “Don’t know what came over me”.

“Your face went pale, you scared me!” Leah said.

“I’m sorry” I said a bit ashamed.

“Are you feeling alright? Was it my fault?” She said still hugging me “Did the dress overwhelmed you?”.

“Yes, I’m ok, I guess I haven’t eaten right or something” I said lying a bit.

I didn’t want to make obvious that my sudden breakdown was the fault of the dress and the excitement I felt, I didn’t want to accept what I was feeling, once again I wanted to be cool about it.

“Are you sure?” She said “We can do anything else you want”

“No, let’s go out” I said, a bit too confidently.

I looked at the dresses and turned back at Leah

“Just not on a dress” I said laughing

Leah started laughing with me, and hugged me closer to her

“That’s ok Dani” she said “Well go casual today”

She said this and took out a white oversized white t shirt of her closet and threw it at me, then she took an old red turtleneck shirt and went to the bathroom to get changed, I changed into the white t shirt she gave me, I tucked it a bit into my jeans as it was too oversized, It ended up looking a bit trendy, as a retro look, I could notice all this time spent with Leah had made me a bit more aware of my fashion sense, this got me thinking again about how I ended up not wearing the dress. The bathroom door opened, and Leah was already changed.

“Just let me touch up my makeup and we’ll get going” She said as she opened the door.

“That shirt looks good on you “ she said.

“Thanks I guess” I said.

I entered the bathroom and stood next to her, watching her do her makeup, she was doing eyeliner, she was actually very good at it, I was hypnotized, as she finished she turned to me and smiled, then she left the liner on the countertop, and took her nude lipstick, she looked at me in the reflection.

“Do I look good?” She asked holding her lipstick.

“I would look better” I said jokingly.

It was certain, I had no control of myself or what I said, It was as if I was actually asking for it, it seemed like my clumsy way of pretending disinterest while at the same time actually looking very interested.

“I bet!” She said with a smirk

She was the best, she had already gave up on her anxiety to also try and make me feel relaxed, she finished her makeup and looked at me firmly.

“Want some?” She said holding her makeup bag to me and smiling.

I freezed a moment. She laughed.

“I’m kidding, we don’t want another panic attack” She said as she was turning to leave.

“Just a bit” I said shyly.

She turned back smiling.

It ended up being a fun night, she made me forget about the world surrounding me, so I didn’t notice if anyone stared at me or something, I just had a good time without thinking much about how my face was made up as a girl.

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Life in the city - Chapter 5

Author: 

  • Punk Job

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Sisters
  • Sweet / Sentimental
  • Voluntary

TG Elements: 

  • Long Fingernails / Manicures

Permission: 

  • Posted by author(s)

A week had passed and my online classes had started, so I spent bit more time glued to the computer, Carla was bit more at ease now because she knew I would go out from time to time, either by myself or with Leah, she was really happy to see that Leah and I had become so close to each other. Leah would come and lay on bed talking non stop about her job, the gossip and trends of the fashion industry and whatever issue has making her feel bad that day, I enjoyed it as I never saw it as a distraction I could easily concentrate on whatever I was reading on the screen and she wouldn’t mind if I didn’t talked back.

In the days after my little breakdown I kept thinking about it, I was intrigued by my feelings, I kept going back to watching my reflection wearing makeup on the past to occasions it had happened, I was at the same time more scared of the women’s clothes we had kept, yet I sometimes would picture me in different kind of dresses and makeup looks, it was somewhat exciting to picture me as a girl, and at the same time a weird nervous feeling would take over me.

Leah stopped pushing me to wear anything after that time, and that would make me more anxious, I kinda wanted her to push me to wear a dress or do my makeup, so I ended up being the one who made it happen, like a time she was trying a new lip gloss on the shared bathroom and I saw her, wanting her to make me wear it I said “It looks so pretty”.

“It does, doesn’t it?” She said as she turned smiling at me.

Then she just put it back on her bag and went back to my room, I was shocked she hadn’t said something like do you want to try it as she would have normally reacted before the last time, so I had to push a bit further.

“Yes, it does” I said quickly “I will have to try it sometime”.

“Sure, whenever you want” She said as she went directly to the bed.

Again, not even a single push for me to do it at the moment. She was killing me.

“Uhmm can I try it now?” I said finally.

“Of course, Dan, it’s on my purse” she said not even looking at me.

I was in panic somehow, I thought I was actually acting cool and that she would think I was just being funny without an actual interest in wearing it, while at the same time I was dying to try the lip gloss and the rest of her makeup, end up in heels and a dress, yet none of it was going to happen, and I didn’t wanted to make it too obvious, so I just stood up, took the gloss from the purse and went to try it in front of the mirror, my hand was shaking, she looked at me when I came back and laughed.

“You’re so silly” She said and then came back to ignoring me and looking at her phone.

Similar scenes repeated, she wasn’t mean or anything, she just didn’t made a deal out of me wearing makeup as she would have normally done, we could talk about lots of stuff but if I would mention anything to push her to make me look girlish, she would smoothly change subject or just don’t make a big deal out of it.

So this particular day, Carla came into the room while I was in the computer and Leah on my bed.

“My God, Daniel!” she said as she saw me “Your hair is out of control, you really need a haircut as soon as possible sweetie”.

“Let the kid be” Leah said.

“Yeah sure, if we let him be he’ll end up with longer hair than us, already with the clothes he wears he looks almost like a girl” Carla said.

I froze as she said that, already turning at her.

“Don’t look at me like that” Carla said “It’s not like I’m going to ground you, but I worry what your mother would think if she saw you like this”.

“Uhmm” I began “Ok?”.

“If you don’t want to, you don’t have to do it” Leah said.

“Let the kid alone Leah” Carla said “Haven’t I been telling you to let Daniel be a boy and stop trying to turn him into you”

I was now more shocked, they had talked about me, I thought Carla wasn’t actually aware of my little adventures with femininity.

“It’s ok” I said out of nowhere “I have also asked for it”.

That was a weird confession to make, yet it came out of me naturally, Leah giggled as I said it, and Carla was bit shocked.

“Well, then that’s up to you Daniel” Carla said.

“You see, you’re the one trying to control him” Leah said in a joking way to her mother.

Carla rolled her eyes at her daughter.

“You can do what you want Daniel, just don’t let this crazy daughter of mine put ideas in your head” Carla said “If you want to cut your hair I can make an appointment at my best friends salon, just let me know”.

Carla left and then I was alone with Leah and my thoughts, but now Leah was non stop talking to me about what just happened.

“Dani, you know I have grown to love you like a sibling” Leah began “And since my mom told me to stop treating you as a girl I’ve tried to not push you into anything”

“But how did she knew” I said

She laughed

“Kid, she knows everything that happens in this house” Leah said “The thing in the end is that you’re a boy and that I’ve been actually pushing you to be more like a little sister, and we think that you go through with it because you don’t know anyone else and you want to please me as your only friend here”

Wow, they had really talked about me I thought

“So if you don’t want to do something just say it” Leah said “And if you want to let your hair grow as Rapunzel’s or maybe Samson, let it grow, also if you want to cut it let me know, you’re free to be yourself, don’t just go with the flow”

I felt so weird, Leah and Carla had really taken me as family in this month and were I thought worried about me somehow, this was something I wasn’t too used to, in my house my parents weren’t affectionate, my dad was a serious guy and wanted me to be like him.

My eyes got watery and Leah came to hug me, I hugged her back.

“I don’t know why I’m crying” I said in a cracked laugh as tears came through my face.

Leah just laughed and hugged me stronger.

“We care about you, Dani” Leah said.

“Thanks, Leah” I said breaking the hug “I just got emotional, I’m not used to talk about feelings”.

“I’m all about them Dani, feel free” Leah said with a smile.

“So you want to cut your hair?” Leah added.

“I’ll think about it” I said “I actually like it long”.

“I like it too Dani, lot’s of men have long hair, and few pull it off as good as you” Leah said.

I was feeling so numb in feelings that I went full with the moment.

“Leah?” I began “Do you think it’s weird that I actually like wearing makeup”

She was a bit shocked by the question.

“Well some boys wear make up” She said.

“But not red lipstick” I said blushing.

“It’s because they can’t pull it off like you” Leah said.

“I think it’s weird” I said “But I liked it, wearing makeup and girls clothes”

I was shocked to hear me say it, I had thought it before, but it was way too different saying it outloud. Leah who is mostly cool, seemed shocked.

“Had you done it before?” Leah asked.

“Not really” I said “But I remember asking my friends sister to paint my nails”
I was almost whispering I feel, it was becoming too personal and to weird of a subject to talk about, minutes ago we were in a totally different mood. Leah grew a huge smile

“Don’t laugh” I said

I was so embarrassed, I started shaking.

“Hey, I’m not laughing at you” Leah said as she put her hand on my waist. “I’m just glad you trust me with this”

She hugged me again.

“Please don’t tell your mom anything about what I just told you” I said.

“I won’t” She said still hugging me.

Silence fell as we hugged, I felt calm in between my nervousness, I felt I could trust her.

“Do you want me to do your nails?” Leah said suddenly breaking the silence.

Blue toes and jogging pants.jpg

Life in the city - Chapter 6

Author: 

  • Punk Job

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Real World
  • School or College Life
  • Voluntary

TG Elements: 

  • Girls' School / School Girl
  • Shopping

Permission: 

  • Posted by author(s)

Leah had promised to keep a secret that I liked wearing girl clothes and makeup when I was with her, we were hiding it from her mom so that she wouldn’t make any weird ideas in her head or tell my parents, which was the thing that worried me the most. I was already 3 months in my online classes and I was killing it, I could arrange my study schedules and just take the exams, which I was managing to do just fine.

I loved having Leah as friend now more than ever, even though we were seeing less because of her work, it was becoming more demanding, which according to her was a sign that she was being taken more serious and that she probably would land a permanent job in the magazine. In the few occasions she had free time we would see each other, it wasn’t always dress up time, but from time to time she would practice makeup looks on me, and I enjoyed every bit of it, still I liked to pretend it was all something I liked doing mostly as a silly playful thing, trying to hide the fact that I was somehow discovering a side of me I hadn’t had the chance to be before.

“You’re an addict” Leah said.

I was reaching for the lip balm she kept on her glovebox as soon as I got in the car. I laughed.

“I’m not, my lips are chapped!” I said.

“Yeah right”.

I applied it watching my reflection on the visor mirror, it always gave me a rush to apply makeup, it made me smile.

“That one is very colorful, Dani, people are going to notice” Leah said.

She policed my makeup use, trying to help me hide my likeness for wearing it from her mother and people we frequented.

“Do you think so?” I said, still looking at my reflection, then turning to see her

She turned back to look at me

“Well maybe it doesn’t show that much” She said as she looked at me “Anyways it is up to you, I don’t mind”

She used that kind of phrases to make me notice she could actually be right and it would be up to me if I wanted people to notice it. She was driving me to a french class I was going to take, her mother pushed me to do something were I would meet people my age, so after a bit of convincing from Carla and Leah, I decided for a french class, at the embassy, Carla knew people there so it wouldn’t cost anything.

“Isn’t this too snobbish?” I said as Leah drove “To be the kind of person that learns french”.

“Well haven’t you met mother?” Leah replied laughing, “She’s the definition of a snob, and by adherence we, her little pets are pushed to become like her”.

We laughed, I really loved to have been accepted into their lives as one of them, I still spoke from time to time with my parents, but Carla and Leah were rapidly becoming a second family, and it seemed the feeling was both ways.

“Ok, Dani, here we are” Leah said as she pulled over

“Ugh!” I said as I reached to the backseat for my things.

Leah had lended me a little backpack to put my notebook and pencil case.

“Isn’t the backpack too girly?” I said.

“I would be more worried about your tinted lips and pretty eyelashes” She said with a smirk as she payed attention to my face.

“Oh shut up!” I said as I jumped off the car. “Does it really show much?”

“Not that much, but if anyone pays attention they could probably tell” Leah said

I frowned and wiped my lips with a tissue as I stood with the door open looking at her,she then reached for the lip balm, and handed it to me

“Here, take it, so you can re apply it if you want” Leah said smiling at me.

“Aw thanks sis” I said.

I was beginning to call her sis more often.

“Love you, sis” Leah replied

My heart melted and my face blushed, which made her giggle.

“Love you too I said as I closed the door”.

So I went inside and looked for the classroom, I still had around 10 minutes until the class started, when I found the room there were only 2 girls inside, they turned to look at me.

“Is this the A1 Level?” I asked them as I stood at the door.

“Yes, you’re in the right place” One of them replied.

“Thanks”.

They both were seated in next to the wall in the middle of the classroom, one behind the other. As I usually do, I went directly to the back of the room and sat in the corner bench.

I still had the lip balm on my hand, and was about to put it inside the backpack.

“I have the same one! Don’t you love that Benefit line?” One of the girls said.

They both were looking at me, I froze a second, as if by not moving they would forget I was there.

“Uhm I” I said trying to find what to say. “I wouldn’t know, it’s my sister’s”

I thought I was safe, it seemed as a reasonable answer to make it clear I wasn’t a boy who knew about make up, which being honest was true, I hadn’t even paid attention to the brand or knew there was a line of those lip balms.

“You should keep it, it’s a great one” She said jokingly. “I’m Jenn”.

“Hi Jenn and uhm hi” I said while looking at the other girl.

“I’m Anna, hi Daniel!” Anna said, “Is your name Daniel like french Danielle?”

“Uhm, I don’t know, it’s more like Spanish pronounced Daniel, but I guess it sounds the same”

“Oh cool” Jenn said “You speak Spanish?”

“A little yes, but I never use it” I said

“That’s nice, I never learned a thing in Spanish class” Jenn said

“Yes, that’s cool that you already speak two languages and now you’re learning a third” Anna said.

I laughed.

“I guess it is, though most people would probably say I’m actually a nerd for it” I said.

“I’m a nerd too, don’t worry” Anna said.
“I’m not” Jenn said “I’m only doing this to please my father, but I guess it is kinda cool”

By the time the class was about to begin, around 12 more girls were in the classroom, I actually didn’t noticed it was all girl but me until later.

“Bonjour!” said the teacher as she came to the classroom.

Everyone was silent, she smiled and went to the desk at the front.

“Je m’appelle Clarie et e vais être ton professeur”.

Dead silence from everyone in the classroom. Claire laughed.

“My name is Claire, and I’m going to be your teacher” she said.

She began with teaching us to introduce ourselves -Je m’appelle to My name is- and then to introduce one another -Elle est blah - She is-.

“Elle est Danielle” Laura, another classmate said pointing at me

Me without noticing that in what she had just said, it was implied I was a girl, continued with the introductions

“Elle est Laura” I said.

The 2 hour long class had a little break, where some of the girls chatted, this is when I finally came to notice that I was the only boy in the class, something that, in a way, was going to be addressed later in class. By the time the class ended I was more confused with french than at the beginning but I was glad I took it because I was enjoying it, and Jenn and Anne were cool so in the end Carla was right in saying that meeting new people my age would be good for me.

“Alright, I’m just going to make sure everyone on the list is here, and the class is over” Claire said.

She took a look at the list with all the student names.

“Well yes, it seems you girls are the whole class” Claire said “Commonly we have a boy or two, and they always drop out, so since it is only girls this time I hope to see you all finish the full course”.

Oh I thought, she didn’t even notice I was a guy, even without makeup, it had happened before, I guess I do have a few feminine features and probably the long hair isn’t any help, but in the end people always figured I was a boy. I was surprised that no one else seemed to notice I was there, but then Anna turned to look at me and made a puzzled face.

Everyone was leaving and so did I, still confused as to why no one noticed I was a guy, I stood outside the building looking for the bus route on my phone.

“Hey!”

Anna was walking towards me waving her hands.

“Oh, Hi Anna” I said

“Hi! Hey I wanted to ask you uhm” she began

“Well I guess the right way to do it is” she made another pause

“What pronouns do you prefer?” Anna finally asked

I was now even more confused, back in town no one would ever ask a question like that.

“Uhm I… I’m a guy?” I said awkwardly.

“Are you asking me? I thought I was asking you” Anna said laughing.

“I’m a guy, uhm.. He… male pronouns” I continued with my awkwardness.

“Oh, I was right” She said blushing.

“I’m glad” I said.

“Everyone thinks you’re trans, uhm like a trans woman, oh but...” she said “are you a trans guy?, I’m sorry if i’m intruding much, it’s something I tend to do, you don’t have to answer”.

What? - I thought - Is this girl crazy.

“I’m not trans, I’m just a guy” I said now blushing.

“Oh, it’s just that your hair and you do have feminine features, and your backpack and the lipstick” Anna said.

“That’s why the teacher said it was just girls?” I said.

“I guess” Anna said “But the girls were talking about it inside”.

As she said this we saw some of the girls from the class come out.

“I need to cut my hair” I said thinking out loud.

“You don’t it looks pretty if you ask me” Anna said

Anna and I walked to the bus together, her house was close to mine so were going to take the same route. We passed in front of a fashion boutique with mannequins on the window, one of the dresses caught my eye.

“That red dress is pretty” I said.

“It is” Anna said “But you know that saying that doesn’t help your case, right?”.

“What? Can’t a guy just say that a dress looks pretty?”.

“I think you can, but it’s not that common, at least not in the guys who I know” Anna said.

We were standing outside the boutique, looking at the window.

“It really is pretty” Anna said while staring at it.

“You want to go in?” I said.

“Do you?” Anna asked puzzled.

“I don’t mind”.

We went in. Anna asked one of the girls at the store to see that dress, she gave it to us, and as we were watching it, she looked at me and how I was looking at the dress.

“You want to try it huh?” She said.

I blushed and looked at her, I did want too, how did she figured me out so fast?.

I nodded.

She handed me the dress and then said.

“So, you say you’re not trans?”

7385307600_2_2_1.jpg


Author's note: I hope there wasn't much confusion with the name pronunciation, in the end the thing is that we hadn't adressed this before, but Daniel comes from a latin background, and his name is spanish Daniel which sounds different from english Daniel and sounds more like Danielle, which in spanish would be Daniela.

Life in the city - Chapter 7

Author: 

  • Punk Job

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender
  • Crossdressing
  • Transitioning

Character Age: 

  • Teenage or High School

TG Themes: 

  • Identity Crisis
  • Real World
  • Sweet / Sentimental

TG Elements: 

  • Shopping

Permission: 

  • Posted by author(s)

“You did what?!” Leah said.

“It just happened, it was something silly”.

“It isn’t something silly anymore Dani”.

Leah came to sit next to me in bed.

“Have you thought about it? About how you feel? What this actions may reflect about you?”.

I didn’t want to answer, mostly because I really didn’t have an answer. It all just happened, and I enjoyed it, it was something I had just discovered and didn’t put much thought to it, when I did my mind got foggy and I got anxious.

“I… no… I haven’t” I said turning my head to the floor.

Leah pulled my face to her, holding it with her hand, looking me straight in the eyes with a puzzled look.

“Do you like girls?” Leah said.

“Yes”.

“But like, do they turn you on?”.

“I think so”.

“Does wearing women's clothes turn you on?”.

“No… not really”.

She took a deep breath, still her hand on my face, pulled me closer to her and then out of nowhere planted a kiss on my lips, it was a sweet short kiss, I had never felt something like that and my body reflected it immediately.

“What the…” I said.

“You do like girls” She said with a smirk and then pointed at the bulge on my pants.

I quickly grabbed a pillow and covered my pants with it.

“Why did you do that?”.

“I wanted to find out, I feel you’re afraid of letting your true feelings out, so maybe I have to help you bring them out Dani”.

I was so confused, what a sweet kiss, now I wanted more, my body wanted more, it was like a sudden rush, blood pumping through my body, was I in love with Leah?, so many feelings.

“Do you feel the same way when you wear makeup and women’s clothes?”.

“Uhm no, definitely not at all”.

“Ok well, that tells us something, it’s not a kink, uhm have you ever watched gay porn?”.

“What?!”.

What the hell was going on, she was out of her mind.

“Well, maybe that way you can figure out if you’re turned on by guys”.

“I haven’t, no, do you think…”.

“Yes, I think you should try it, it’s only normal to watch porn”.

She had a weird smile on her face, and suddenly I could concentrate on anything else than her lips, I still had the feeling on them on mine, and as this thoughts came over me, I started to feel my body reacting again.

“Uhm... right now?”.

“No!l I don’t want to see you jerk off!”

“I won’t jerk off”

“Well we don’t know that Dani, you might get a strong urge and I don’t want to see that”

“Stop it! First you kiss me, then you tell me to watch gay porn, it’s all too much”.

“Well no, first you got yourself women’s clothes, and then you got obsessed with wearing my makeup, and then you go out and buy a dress with a girl you just met in french class, so don’t make it as if I’m the one coming with the weird stuff, I’m just trying to help you out”.

I feel my heart going fast, she was right, it was all to weir, she was probably doing the right thing by helping me figure this shit out, but I didn’t want to, I didn’t want to be weird, to be not normal, I wanted things to stay the same, the same where she would help me look like a girl and and nothing bad would happen, and no one would judge me, I looked at her, lost in my head, looking for some comfort.

“Everyone at french class thought I was a trans girl”.

She brought her arm around me and pulled me close to her in a hug, my eyes were teary.

“Are you worried they might be right?”.

I took a deep breath.

“I don’t know, I just want to be normal”.

I was crying already, like I hadn’t cried since I was probably a baby, I was overwhelmed with everything.

“No one is normal Dani, I am not normal and certainly you’re not normal either, but that doesn’t change anything, you have to find yourself to be happy, maybe you’re trans, maybe you’re not, but you have to figure out who you are, I’m just trying to help you, I don’t want you to be hurt”.

“Thanks” I manage to say in between my sadness.

“And if you’re going to go around buying girl clothes with strangers, we have to make sure you’re safe Dani, I don’t want anyone to hurt you in any way, that’s why I’m pushing you, because you have already went out of your way to do crazy things, and that’s ok, but let’s just make sure we figure you out, before you do it again, so we can build an armor and shield around you before someone tries to harm you”

She was stroking my hair, she was right, she was so sweet. I was already getting more calm.

“So, should we watch gay porn” Leah said, and we both started laughing.


Author's note: Just a tiny chapter following the ending of the last one, and getting us prepared to the discovery journey that Daniel is going to take


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