Karli's Second Chance

Author's Note: Hi everyone. Thanks for reading my first ever attempt at a stand alone story. This one takes some inspiration from some events from my real life. As always, I appreciate any constructive feedback! :)

My palms were sweaty. I laid in my bed staring at my phone screen with thoughts of doubt and indecision racing through my head.

My eyes wondered away from the screen momentarily as I pondered whether I should post the photo to Instagram or not.

"Fuck it," I thought to myself as I abruptly pressed the button, my freshly manicured red thumbnail clacking against the glass as my finger made contact with the screen.

I felt a sense of relief at first, but after a few moments, panic began to set in. It may seem strange to panic over posting a single Instagram post, something millions of people do every day, but this was my first post in over seven years. It was my first post as... me, the real me that is.

Most people who follow me on Instagram know me as Karl. I grew up in a pretty rural town in Florida before moving about five hours away to Orlando for college about seven years ago. I was pretty popular in high school, played multiple sports and was even on the Homecoming Court.

But nobody in that small town knew the secret I had kept since I was around 12 years old - I had always felt like a girl inside.

In middle school is when I first noticed it. I would see the girls in my class with their bright painted nails and I found myself having the urge to have them too. Almost every day I would use highlighters and color my toenails in secret every night before bed so I could secretly have "painted toes" all day at school the next day. It was my dirty little secret, and it gave me such a rush seeing my toes crudely painted with pink highlighter before I slid my socks on to hide them.

In high school is where my crossdressing really started. Even with my family home I would sneak off to the bathroom sometimes and find my moms lipstick and put it on. Even having it on for a mere 30 seconds or less and seeing myself in the mirror was enough to get me excited every time I did it.

When I was lucky enough to be home alone, I had a go to outfit I would always pick out from her wardrobe. It included a white strapless bra, a white tank top and a black mini skirt. Looking back now, I definitely looked like an absolute disaster, but it made me happy in the rare occasions I was able to do it.

College was the real game changer. As an independent adult, I was able to do as I pleased without anyone questioning it. Considering I lived alone and had moved several hours away from my home town, nobody had any idea who I was.

My collection of women's clothes started to build initially by online shopping. Forever 21 was my go to retailer at the time. I would buy numerous outfits at a time and just wear them at home alone. That was great and all, but I felt like I needed to up my game. I decided to buy makeup and a brown bob wig from Amazon to complete the full look. I was nervous the first night I put the entire look together. I didn't really know what the hell I was doing with makeup, but I followed a YouTube tutorial for a smoky eye look. Once I got the wig on and fully situated, I looked in the mirror and my heart skipped a beat.

"Is that really me?" I thought to myself.

I actually looked pretty good. I ran my fingers through my hair as femininely as possible to try and continue the illusion. My fire engine red nails I had just painted certainly helped add to the look. This was the exact moment I knew that this girl is who I really was.

I spent so many nights in college dressing up fully before laying in my bed and talking to random strangers on random text chat apps as my alter ego Karli. It was pretty well accepted that those kind of apps were just glorified sexting and nude swapping apps, but I was there for it.

I had so many good photos of myself at this point and I loved showing them off to people, even the lewd ones.

Most of these sessions ended with finding a session with a bisexual girl who was super into my whole gender bending persona. Often, we used each other to get off either through role play sexting or photo swapping.

To be honest, it really wasn't the girls I chatted with turning me on so much, it was more that they were turned on by me. On top of that, there was really something so alluring about seeing a hand with long Impress press-on nails that was my own stroking my cock as I chatted with them.

It may sound strange, but it was this chatting with random strangers that were always so accepting of who I was that was the final thing that gave me the courage to become the true me.

It was a slow and long process over the next few years with surgeries and hormones, but I'll always be thankful for that night that served as the catalyst for the woman I am today.

As I stared off into space, recollecting my past journeys that led me to where I am now, my phone made a ding. I looked down anxiously to see what was going on with my post.

It wasn't anything too crazy if you didn't have any context, it just looked like a normal dirty blonde haired girl in a cute dress with the caption saying "I'm back!". But one single scroll to the most recent picture before that would have anyone questioning what was going on as they would see my previous male self in the photo.

To my surprise, the notification on my phone wasn't from a comment or a like on my photo, it was from a DM.

My heart started racing as I wondered who it could be that messaged me so quickly. Who could it be from? Was it going to be a hate message? Was posting a mistake after all?

I finally got the courage to see what it was and clicked the messages button.

To my surprise it was from a girl named Cali, an ex-girlfriend of mine from high school. We dated for a few months when I was a senior and she was a sophomore, but broke up when I moved away for college. Funnily enough, she is actually the one I lost my virginity to two nights before my graduation.

"OMG girly! You are too fucking cute!" her message said as I read it with a sigh of relief.

"Thank you so much! That means a lot," I wrote back.

"How did you change so much? What the heck, girl!" she responded.

"Lots of money and time lol" I typed back.

"Well damn girl! I'm loving the new look. And that dress is killer," she replied.

I had to admit, the way she was instantly referring to me as "girl" and didn't question anything at all made me really feel good inside. I found myself smiling for our entire conversation.

"Thanks. And the makeup looks great, right?" I asked.

"Yeah, yeah. Totally. It really suits you. It's not caked on or anything like some of these girls are doing these days," she responded.

I was flattered by her compliment.

"I was actually really nervous about posting. But it feels so nice just letting go and putting the real me out there," I typed.

"Oh my God girl, don't even worry about that. You look amazing. Like I said, I love the new look. Plus you've got that body!" she typed back.

I couldn't believe my eyes. I had literally gone from almost having the biggest anxiety attack of my life a few minutes ago, and now I was laughing and blushing like a little girl over this exchange with Cali.

"I mean, thank you. But I'm no you! I saw your recent bikini photos from the trip you took a few weeks ago. Talk about an insane bod