Chapter 6 - Homework

Second Chances by Emily

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Synopsis: Tony/Christina has some "homework" to do before returning to school in the morning. He's going to need help if he's going to complete his mission.


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My mom hugged me and congratulated me as I showed her my new licence. I looked at the licence in my hand. It was very simple. Not like the more complex security-enhanced licences in the future. This was just a laminated piece of paper with my picture and personal information on it. Christina R. Demarco.  I wonder what the R stood for.  Brown eyes.  5’6”.  Corrective Lens.  Wait.  Tony’s 5’8”.  Did I feel 2 inches shorter?  I looked at the picture of me. I'm not facing the camera because looking straight ahead was reserved for 21 plus year old drivers.  I remembered that all underage drivers had to face 45 degrees from the camera. I am looking kinda cute in this picture. Wait.. where did that thought come from?

On the drive home. My mom and I made casual conversation. I figured out that we're having my birthday party on Sunday. My whole family was coming. Apparently I wasn't having a party for friends. None of that was surprising. I think the same events went down when I was Tony too.

When my mom and I weren't talking I was letting the guardian angel's words sink in. I was going to need a plan if I was to return to my life.

So I need to date more. I need to have fun. Maybe join something. But I also need to figure out my purpose here. I'm going to need to get to know more people. Maybe that's what the angel was getting at. If I made more friends, I can figure out what event I need to fix.

When we got home, my sister was eager to see my licence and congratulated me. "Can you drive me to school tomorrow?" She asked.

"Of course" I replied with a chuckle since I was already expecting that question, since that was my arrangement with Cindy back in my timeline.

I decided I needed to be alone with my thoughts. It would be the first time I was alone since I left for school this morning. "I'll be in my room!" I called out as I headed there. "Let me know what everyone decides on for dinner!"

I closed my door and fell onto my bed exhausted from my day. The evening light shone through my room. The shadows of the oak tree in front of the house danced on the walls. My room was quiet except for the rustling leaves of the calm September breeze outside my window. My clock read 5:30 PM. It's been about 12 hours since my world was turned upside down.

I scanned my room. It really was almost like my room except for the colors and dresser mirror. Christina had very much the same interests as Tony. I caught a glimpse of a framed photograph I recognized. It was me dressed in my Tae Kwon Do uniform doing a blocking pose in front of a cheesy starry backdrop. At first glanced it looked like me - 14 year old Tony. Except upon further inspection, it was a younger Christina with bangs and her hair pulled back in a ponytail. Pictures like this are reminding me that Christina is me. I have to keep reminding myself that Christina isn't another person who's going to come back and take her life back and yell at me for screwing it up. Her life is mine for at most the next 13 days - hopefully.

I took a deep breath, closed my eyes and let the calming breeze flow through me. Thank God I have thoughts to myself. I needed to think without interruption.

Now, how do I fix this? It's not like I didn't try to make friends the first time around. It's just that I had a hard time talking to people. I need to resolve to fix that. More friends will lead to dates, parties and such. Hopefully that will lead me to the thing I am actually supposed to do here to complete my mission.

I heard the phone ring off in the distance. After a few seconds Mom yelled down the hallway. "Chris, It's Dad on the phone."

I slid off the bed and went to the door and out to the kitchen. My mom handed me the corded phone. "Hello?" I said as my mother walked out of the kitchen to do something else.

"Hi honey" my Dad greeted me. It's so weird hearing my dad call me "honey". Where I came from, that term of endearment was reserved for Cindy. "How'd you do?"

"I did great! I got my licence!" I replied.

"That's great. Congratulations." he said "I knew you could do it. I'm not sure why you were so nervous the past week."

"Thanks Dad." I said, subconsciously playing with the telephone cord.

In my life as Tony, my father is the person I could always get advice from. I'd love to get his advice for my current situation. But how do I ask this version of my father without revealing I'm a gender bending time traveler from the future.

"Hey Dad," I started, "I need some advice"

"Go for it." he replied.

"I have this project that I'm doing. I gave it my best shot at first and completely failed. But the good news is I've been given a second chance. But now I realized that I'm really unqualified to be doing it in the first place. How do I proceed?"

"Wow, that's vague" he commented. "You're not giving me much information. But either way, I have a hard time believing that my daughter is unqualified at anything. Are you sure you gave it your best the first time around? I know you have a tendency to rush into things without thinking them through."

"Maybe I just coasted." I confessed.

"Well, there's your problem." He said. "Every project I've seen you succeed at, you've devoted all your passion to it. If you put half as much passion and energy into this project as your programming, then you'll do great at it."

"Thanks for the advice." I said. "I'll see you tonight. Bye."

"Bye honey" he said as we both hung up the phones.

I returned to my bedroom and sat on the edge of the bed. I had a thought forming. If this was a programming project. I would pour myself into it. I'd do the research. I'd talk to the experts. I'd design the end product. That's what I have to do here. I need to pour myself into Christina.

"OK." I told myself out loud. "So I'm going to need to go full Christina."

But what does that really mean? Christina is essentially Tony with boobs. I looked in the mirror again. I looked beyond the glasses. Beyond the bland t-shirt and jeans I picked out this morning. The same thought came back to me from looking at my new licence. Christina is cute. She is. I see it there. I see the opportunities. Christina is a blank slate to work with. The angel gave Christina enough background for me to work with.

I opened my closet to inspect everything closer. Mostly t-shirts. There were some fitted v-necks. Those are promising. There were some black skirts, and white button down shirts mostly for band concerts likely. A few flannel shirts. There were some floral dresses at the back. This essentially looked like the feminine version of Tony's high school closet I told myself. Mostly casual with the few formal and semi-formal options for special occasions.

Research. I reminded myself. I scanned my bookshelves. Right next to my USS Enterprise model was my Junior year, yearbook. I pulled it out and started scanning the pages. Lots of grunge. Lots of flannel over-shirts. Jeans and t-shirts were common. Some of the girls did the plaid and khakis thing. "Geez!" I thought to myself. "I don't remember the 90's being this plain."

"OK Tony" I steadied myself. "Let's not get frustrated and we can come back to that." How about this other problem that's been bugging me. "Amber."

So what do I do about Amber? She's an element that didn't exist in Tony's life, so no matter what I do, it'll be different. I have a choice. I confront her, or ignore her. What if I try to be her friend? "After all, you catch more flies with honey than vinegar, right?" I told myself.

It is weird, I told myself. That I don't seem to remember this Amber at all. I wonder if changing my gender switched a male bully in my life with a female bully.

Back to the original problem. I'm going to need help. My mom and sister seem to be logical choices. Since my sister offered this morning, I might as well go see them. The thought of going to my younger sister for fashion advice is kind of weird. Tony and Cindy didn't really get along in high school.

She was the popular one. Because she was in cheerleading she knew more upperclassmen than I did. It wasn't until we were both adults that our sibling rivalry vanished and we could really connect. She moved closer to me while she was in grad school. She became my link back to my family after my parents moved away down south. I brought her along to softball pick up games, and she joined me and other friends when we went out on the town. I certainly confided to her about my various attempts to find a date in the big city. Her and her future husband were the first in my family to meet the woman who would later become my wife. I mean ex-wife.

I ran downstairs to our family room. My sister was in front of the TV, watching a rerun of "Saved by the Bell' while talking on the cordless phone. Actually, I don't know if it was a re-run. It could've easily have been a brand new episode for all I knew. I stopped and watched a few minutes of it to check out the fashion choices of Kelly, Jesse and Lisa. People did not dress like that in my school.

I sat down on the couch next to her and turned to her. "I want to take you up on your offer." I stated, interrupting her phone call.

Her eyebrows raised as I could hear her best friend talking on the other end of the phone.  

I piqued her curiosity.  I continued.  "I need to learn to do my own makeup. I thought you could help."

Her eyes got wide and a big smile formed on her face. "Jill, I need to call you back. Bye!" She hung up the cordless phone and turned to me. "For real? You're not joking?"

"For real" I said.

"Great, let's go to the mall!" she said grabbing my hand and pulling me off the couch.

"Wait, why?" I said.

"Because I've seen your closet." she replied and turned to yell up-stairs. "Mom, let's go to the mall!  We’re giving Chris a makeover!"

I sighed. Oh no, what have I done.

"That's a great idea" my mom said walking down the steps. "Dad's going to be home late. We can eat out at one of the mall restaurants."

And that's how I found myself driving my mom and sister to the mall on a Tuesday evening. This day just keeps getting longer.

* * *

Of course I was driving. My mom took shotgun, and my sister was in the backseat. About halfway to the mall, my sister started a topic I didn't expect.

"I heard you and Amber go into it earlier." Cindy said.

"How'd you hear about that?" I asked.

"Duh, She told me." she replied. 

That’s right. Cindy and Amber are both cheerleaders. 

"She said, and I quote, that tomboy sister of yours got in my way so I had to take her down a notch"

"She really said that?" I inquired. I didn't expect Amber to bring me up to anyone. I was a nobody to her.

"Chris, you don't want to make an enemy of the head cheerleader. " my mom interjected.

"She's the head cheerleader?" I blurted out.

"Seriously, Chris.” Cindy said. “You should get your head out of the computer sometime and look up."

"Well, I'm looking up now. Maybe I should just talk to her."

"Ha." my sister laughed. "There's no talking to Amber. She's a total bitch to everyone who's not her friend. She treats us freshmen like crap. I'm told she's been like that ever since she became head cheerleader last year."

Ah, the old "power corrupts" story. Hearing that my sister has a problem with Amber too didn't make me feel better. It actually made me feel more protective. I will have to resist the urge to avoid Amber. I will just have to find a way to be her friend.

* * *

We entered the mall. This was totally a blast from the past. Stores that no longer existed. Radio Shack, Waldenbooks, KB Toys, Sam Goody.. The mall even looked different. More seating. No annoying kiosks in the middle of the walkways..

One store caught my eye to my left. It was an optometrist's office. This is actually perfect.

I didn't originally get contacts until I was a freshman in college. I looked at the optometrist office and decided, "Nothing says changing the timeline than doing something a year early."

"Mom, I need to do one thing." I said. "I want contacts"

"Now?" my mom asked, surprised.

"There's no time like the present!" I chuckled. "This won't take long. We have time"

"After dinner." she said. I conceded since I was hungry too.

After dinner I did my eye consultation. 17 year old Christina's eye sight is certainly better than 37 yr old Tony's eye sight. The optometrist gave me a sample pair to wear while my longer term contacts were ordered. I wowed the doctors, my mom and sister as I was able to put on the contacts first try. "Wow!" Cindy said. It took me an hour and lots of tears in order to get those in.

We left the store optometrists office.  Wow.  I can see again!  I stood in the center of the mail admiring my new 20/20 vision.  So crisp and so clear.  I hadn’t gone for an eye appointment for at least 10 years, so it’s likely that 37 year old Tony needed a new prescription too.

"Enough delaying" Cindy said as she pulled me to the nearest women's clothing store, leaving Mom to pay.

Over the next half hour, my mom and sister proceeded to pick out tops and skirts to try on.

I took a stack of clothing to the dressing room. I took off my jeans and pulled up the first skirt. It was a navy blue and white plaid skirt. It rested nicely on my hips. I kinda liked the feeling on my legs.

I turned to the mirror. I smiled at Christina. I then struck a pose. And another. I could feel the air conditioner on my legs and my bare thighs. I took off the t-shirt and put a light blue button down blouse on. The fabric felt great on my skin. The blouse was a nice fit cut. The top most button was low enough to make a nice v-neck. I turned my attention back to the mirror. I swayed my skirt back and forth. The breeze between my legs was a new experience. I tossed my hair a little bit. I dare say this is making me feel sexy. I never thought I'd say that when I woke up this morning.

"Are you going to show us?" My mom called.

I stepped out of the changing room to show my mom and sister.

My mom walked around me. "Oh Christina, so you're so gorgeous." she said. The compliment made me feel flush. Did I just blush?

The next item to try on was an orange sunflower print sundress with spaghetti straps. I put the dress over my head and checked myself in the mirror. This outfit is fun. I like the way these fabrics feel. Everything is so light.  It's like night and day from the way jeans feel.

I modeled this outfit for Mom and Cindy too.

"Oh honey." Mom said. "I don't know what has gotten into you or what you're planning. But whatever it is you're scheming - you'll knock 'em dead."

Scheming?  Did Christina seriously never dress girly?

After I put my original clothes back on, I put the skirt, blouse, and dress in the basket, trying to be cool and not show how excited I actually was. "I like these. Let's get them." My mom checked the sizes and went to find more clothes. My sister smiled and was giddy.

There’s one thing I will remember from this experience. Let it be known that in that mirror, in this clothing store, at the mall, was the first time I saw Christina smile.

* * *

When all was said and done, We had gotten several skirts in different patterns, a few different colored tops, that sundress and some new bras. When we returned home my Mom and sister sat me down and taught me how to put on makeup. Foundation, concealer, eye shadow, mascara, lip-gloss.

"Be careful how much you apply." my mom said. "If you can see it, it's too much."

After they did my make up. They showed me a hand mirror. Wow. Who is that girl? I was simply radiant.

My makeover lasted for 2 minutes. Then they forced me to wash my face and do it again myself as they watched.

I wasn't able to do it that well the first time. My hands were shaking too much. I used too much of.. something.

Of course. I remember what I told myself to do earlier in the evening. So I washed my face and tried again.

The second time was much better.  They wanted me to do it a third time, but I had homework to do.

I washed my face and thanked them for their help.

* * *

After the makeup session, I took out my contacts. My eyes were irritated and watery. This was the first time these eyes had contacts in, and they were tired. I retrieved my glasses and I sat down and did my homework. My dad came home after working late. I showed off my new licence and he gave me a hug and told me he was proud of me. I continued my homework. I read the next few chapters in Catcher in the Rye, and did a few Pre-calc exercises.  Doing homework was just as painful as I remember.

When all was said and done, It was now around 10 PM when I finally sat down at my computer in our den with my junior-year yearbook. I yawned as I turned on my PC. An old Dell tower with a CRT monitor. It took a few minutes to boot up. It's been well over 24 hours since I last checked my phone. It's an addiction I haven't kicked yet. Well, I guess I’m kicking it now, since I won’t have it for 2 weeks.

But my habit to check my email and messages was still there.  Now granted I wasn't expecting any messages from the future, but whatever. I was greeted with the Windows 95 login music. I clicked on "Open Dial-up Connection" and out of the computer's speakers came the familiar and unmistakable dial-tone and squeal of dial-up internet. 30 seconds later, AOL Instant Messenger popped up.

I double-clicked on the Outlook Express icon to check my email. Not really expecting what to find. No new emails. No spam. No messages from friends.

I found my computer's CD player and hit play. A Green Day album played. I turned the volume low and let it just play in the background.

I pushed the keyboard to the side and opened the yearbook. I started scanning my classmates, putting names with faces. I was flooded with a whole bunch of "I remember them!" Some of them were not bad. Maybe I was judging them incorrectly. I closed the yearbook.

I pulled open a browser. It was set to my "home page" on Geocities.

"Welcome to Christina's World" read the scrolling marquee. Cringe! I found the home page editor and immediately changed the scrolling marquee into a static header. The rest of the page was links to some of the projects I was working on. There of course were links to my marching band's homepage and my high school's home page. That's right. I think I volunteered to help them with their websites. A link to my sister’s webpage on

I still had my mall outing on my mind. I wonder if I could search results for outfit ideas. I instinctively typed "" into the address bar. I was greeted with a "Page cannot be found" error page. I laughed. Of course. I almost don't remember how I got by during this age of the internet.

"Too bad I only have 2 weeks." I whispered to myself. "Or else I'd totally create my own Google or Facebook."

I found a shortcut on the browser's toolbar for Yahoo!. Before I could click that I got an IM from Ron.

"How'd it go?"

"I passed!" I typed

"Awesome" he responded.

I started to feel tired and drained. My eyes, heavy. I decided that I've done all that I set out to do this evening.

"exhausted.  g2g. I can talk about it tomorrow. see you in the morning" I typed.

I shut off my computer and I walked back to my room. I pulled off my shirt and jeans. Walking around my room in just my bra and panties, I then picked out a random t-shirt and another pair of shorts. I need more time to get ready. I told myself as I changed my alarm clock to 5:00 AM. I unclipped my bra. Oh wow... That feels good after a long day.

"I think there's something you've been putting off" I told myself. I closed my eyes and I turned to the mirror, topless. I reopened my eyes.

I examined my breasts, slowly running my hands over them. First thing I noticed was that I had a fading bikini tan line. I must've been to the beach or pool a few weeks ago. The next thing I noticed was my pink areolas. Much bigger and prettier than Tony's. I turned to my body so I could see myself from different angles. On the top of my left breast closer to my armpit was the same birthmark that Tony had. "This is my body." I reminded myself.

I continued caressing my breast. Eventually I rubbed my thumb over a nipple and watched it become erect. I bit my lip. I'm tired, but this is exciting. Let me just lay down first.

I put my night shirt and shorts on, turned the lights off and crawled into bed. The moment my head hit the pillow I could feel the waves of sleep coming for me. I stuck my hand under my shirt and rubbed my breast a little more. That's nice. I could get used to this. Then I noticed a dampness down below.

My caressing got slower. I was fading. Today was just too long. I had every intention of continuing my exploration, but fell asleep with one hand under my shirt and the other hand with fingers under my panties’ elastic band.



Hi, I'm Emily and I'm writing Gender Transformation Fiction! This site is a place for my to keep all of my stories in one place. I'm also a software developer in the daytime, so this site will also be a proving ground of cool new features that pop into my head. Feel free to message me on Twitter or at my Discord Server! You can also find me on and

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