Your Best Life Ch. 01

I'd made more mistakes than I could even begin to count. I sat at the desk of my meager studio apartment, well over two thirds through a bottle of Jack. I tossed back two generous handfuls of Vicodin from my shoulder surgery a couple years ago and waited for darkness to take me. In the brief moments before unconsciousness, before my vision dimmed and my mind went hazy, I found myself thinking about the past. The time I'd wasted. The people I'd hurt. The ones I couldn't save. It took me a long time to figure out who I was, and what I wanted. The path to happiness was right there before me, but I was too damned blind. Maybe I didn't deserve it, maybe I didn't want it. Fuck. I felt tears openly stream down my cheeks. It was all too little, too late. There was no going back, no fixing the wrong I'd done. All that was left was to wait.

I awoke to sunbeams cascading through cheap floral pattern drapes. Those were oddly familiar. Was I dead? I leaned up, groggily grabbing my thick rimmed glasses from the end table and assessed my surroundings. If I was dead, then why was the afterlife my Grandma's old house circa 2005? Perhaps there was some sort of cosmic joke being had at my expense. I felt none of the effects of my whiskey and pill binge the night prior. In fact, I felt downright spry. I rolled my arm tentatively. It did not carry the usual stiffness and aches that it once had. I reached back, prodding with my fingers. No scar. I felt a chill run up my spine. This was all too weird; it couldn't be real right? Doing my best to remain calm, I headed to the full-length mirror that hung from the closet door.

I looked in disbelief and wonder, a reflection of my younger self staring wide eyed back at me. I had none of the wear and tear of life, the dark bags that often hung beneath my eyes were gone. I ran my hand along my jawline. Sparse patches of hair ran the length of my chin and neck. I grimaced, recalling how hard I had worked to get rid of that in the past. The future? Fuck it, this was all too weird. That's when I heard a familiar voice on the other side of the door. "Finley, get dressed there's someone here to see you." I felt a lump rise in my throat. My grandmother and grandfather were my caretakers throughout most of my adolescence. My mother died in child labor and my father was rarely present. They treated me well, and I had loved them with all my heart. A couple years back they both passed. I had a small family, and none of the rest of them were too keen on them. I attended and organized the funeral alone.

My father had dumped me with my mom's parents at a young age. My grandparents said it was because he was too busy or ill-equipped to raise a child. I think he couldn't stand to look at me. Everyone always said I had a remarkable resemblance to my mother. I had her jet-black hair, and bright blue eyes. I was a small kid, measuring at barely five foot six, with a rather slender build. I wasn't athletic or good at sports, I tended to prefer reading and writing in my spare time. When I was young, I had grand aspirations of being an author, though they quickly dissipated in my soul crushing corporate employment as an adult. Overall, I kept away from others, building sturdy walls to keep myself isolated and safe.

I rifled through my closet for clothes, though the selection was far from diverse. In my teenage years I wore almost exclusively band t-shirts and slim fit jeans. On my sixteenth birthday I had gotten my ears and lip pierced as well. I was a edgy little fucker. As I was changing, I felt a stinging pain against my hip. I tentatively reached down, my fingers brushing against raised lines of ink. On my eighteenth birthday I had gotten a tattoo of my mother's namesake, violets. Judging by the tenderness, it was only a few days after my birthday. At least that helped me narrow things down. I hurriedly dressed and headed for the door. I should have seen it coming, but nothing could have prepared me for who was on the other side.

As the door swung inwards, I found Jason towering over me. I could not begin to describe the torrent of emotion within me at that moment. I did not even notice as tears began to fill my eyes. I was too numb and overcome with shock to properly comprehend anything around me at that moment. I hadn't seen Jason in nearly fifteen years, not since he was buried shortly after our high school graduation. He died picking me up one night after I was out drinking too much. A car side blinded us in an intersection. I made it out with a few scars, both mental and physical. He did not. I threw my arms around him suddenly, openly sobbing against his chest. I did not know if anything around me was real, but at that point I didn't care. He put his arms around me, holding me against him. He looked down at me in a mix of confusion and concern. "Fin, are you alright?"

I nodded, unable to find my voice to respond. I caught my breath and managed to compose myself after a few more minutes. In the past Jason and I had a curious relationship. He was my neighbor growing up and had become like an older brother to me. I was also in love with him, and he knew it. I don't know when it happened, I felt strongly for him just about as far back as I could remember. He was the popular kid in class who everyone looked up to. He was tall, athletic, sociable, and everything I wasn't. I cannot imagine what my life would've been like growing up without him. Jason helped me make friends and protected me from others who found me an easy target. How could I not fall in love with him?

I was never taught about gender and sexuality. Up until high school, I had no idea that my feelings for him were considered socially taboo. When other kids started to tease me, I began distancing myself and burying my feelings. I was doing pretty well until I had drunkenly confessed to him one night on my birthday. My eighteenth birthday. Fuck. To me that night was a distant memory that occurred over a decade ago, but to him it would have just happened. I felt myself stiffen uncomfortably. Jason cleared his throat awkwardly. "Hey, uh, can we talk about the other day?" There it was.

"Yeah," I croaked weekly. Back in our teenage years I said I didn't remember what happened. I laughed it off and attributed it to my drunken state. I wasn't sure if this was an elaborate memory reel in the brief seconds before death, some twisted afterlife, or an honest to God second chance. Either way, I wasn't going to screw it up again. I knew where that road led.

"So, you remember then?"

"I remember," I confirmed meekly. "I meant what I said."

Jason wrung his hands, clearly as uncomfortable as I was. "I don't know-"

"It's fine," I assured him, afraid to hear the rest of his sentiment. "It doesn't have to change anything."

He sighed. "Fin, how can it not change anything?"

He had a point. If things went back to the way they were before, I might lose him all over again. Even if this reality was fake, I couldn't handle that. "I'm sorry," I responded, unsure of how to continue.

"I didn't know you were gay."

Right. There was still one more bombshell to drop. It was something I had not come to terms with until my twenties. "I-I'm not."

"Bi?"

I shook my head. Though I had an appreciation for the female form, it was more akin to envy rather than lust. "I'm transgender," I blurted out. Jason's mouth hung visibly agape as he processed my admission.

"You... What?"

"I like guys... I-I like you, but I'm not gay. I'm a girl."

Jason ran his hand through cleanly cropped light brown hair. His expression betrayed his bewilderment. I couldn't blame him; it was a lot to take in. We sat in silence for a while as he came to terms with my confessions. "I don't know what to say," he noted with a nervous chuckle.

"That's fair," I responded, my gaze sheepishly downcast.

Jason affectionately ruffled my hair. The sensation sent a goosebumps rippling across my arms. I never thought I'd feel that again. "Christ Fin, that's a lot to dump on a guy."

"I'm sorry," I mumbled.

"It's alright," he assured me with a deep sigh. "We'll figure this out." I leaned my head against his shoulder, feeling defeated and exhausted. Jason slipped his arm around me comfortingly.

We spent the rest of the afternoon together. Things were tense, but we mostly just hung out as normal. That night I dreaded going to bed. I feared that I would wake up alone in my apartment, or that I would not wake up at all. To my surprise, the following morning I was still in my childhood home. Did that mean I really went back? Was I staying for good? The whole situation was too bizarre to say for sure. For the moment, I decided to enjoy myself. I hopped in the shower, shaving head to toe and basking in the warm water. As I stepped out, I heard a buzz from the counter. I flipped my Razr phone open, smirking momentarily at the dated technology. It was a text from Jason, inviting me out for dinner.

I beamed enthusiastically. My heart fluttered in a way I had not experienced in years. I had a while before we were supposed to meet, so I decided to make a stop at the mall. I stopped at a local makeup chain, picking out a cheap kit that would suit my purposes. I also stopped by a women's clothing outlet. I exchanged my tattered old band tees for a nice form-fitting shallow maroon V-neck. I was also eager to be rid of my boxers, as over the years I had become accustomed to the tighter fit of panties. The checkout girl gave me a weird look, but it didn't bother me too much. I was too excited to care. I hurried home and got to work. My future experiences afforded me a measure of skill with cosmetics, for which I was grateful. Years of practice taught me to contour and highlight expertly. I grinned proudly as I observed my handiwork.

I showed up to the diner ten minutes early to give myself some time to calm my nerves. To my surprise, Jason was already there. The moment I saw him I felt giddy, like I was a kid again. I mean technically I was. Whatever. I grinned nervously as I took a seat across from him. Though he did not mention it, he gawked openly at my more polished appearance. He quickly composed himself as the waitress came over. The server eyed me judgingly. I wasn't particularly surprised. I grew up in a conservative town, where non-conforming expressions of gender was relatively unheard of. I certainly stuck out like a sore thumb, but I didn't give a shit anymore. I had endured the countless stares after coming as an adult. They no longer phased me.

I ordered a water, too nervous to have much of an appetite. "Hey Jason," I greeted him.

"Hey Fin. You look, erm, cute," he responded, fidgeting restlessly. My face flushed crimson. I felt slightly silly getting so flustered over a single compliment.

We exchanged tense small talk for a while as Jason finished his drink and food. After he finished, he invited me over to watch a movie. This wasn't anything particularly out of the ordinary, but I expected him to be more hesitant in being alone with me. He drove us over to his house, where we were greeted by his parents. I got along well with Jason's mom and dad. They were laid back and indulgent of the two of us and were happy to accommodate my frequent overnight visits. His mom welcomed us in heartily, though she gave me a curious look, likely due to my drastically different image. His dad was on the couch watching TV, so we were sent up to Jason's room to watch our movie.

Jason kicked back on his bed and grabbed the remote, crossing his legs casually. I yearned to join him at his side, any other day we would have. Before I came out, and spilled my guts to Jason, it would have been commonplace. On more than one occasion I had even laid on his shoulder or lap. I treasured those moments, even if he did not hold them in the same regard as I had. I sat at the chair next to his desk, a small smile creeping to my lips as I reminisced about the past. Of course, streaming services were not commonplace in the current time period, so we were left to peruse his DVD collection.

Jason was an avid fan of action movie fodder. He owned just about every disc in the genre known to man. I was always more into horror, a taste which he did not share. He had prided himself on not having a single horror film, up until a couple years back when I had given him a copy of John Carpenter's 'The Thing' for his birthday. He was furious, though he had never discarded it. To my surprise, that was the movie he suggested that evening. I gave him a skeptical sideways glance. Perhaps he was taking pity on me, but I wasn't about to pass up the opportunity. In my previous life we had never watched it together, and I hadn't watched it since.

I excitedly leapt into action, inserting the disk and starting the movie. I took my seat back at the desk. "Fin, c'mon," Jason noted in exasperation. I looked back at him in confusion. "I know things are different, but you're not watching the movie on that shitty IKEA disaster."

He wasn't wrong, the chair was an immense pain in the back. It was also tempting to sit on his bed and watch movies at his side again. I hesitantly joined him on the bed, though I made sure to sit as far apart as possible. I felt conflicted. On one hand, I had been dreaming about doing this again for the better part of a decade. On the other, I didn't want to screw things up between us in case I stayed in whatever reality this was. Jason rolled his eyes, clearly fed up with my trepidation. He placed his arm around my waist and pulled me in from the edge of the bed, eliciting a startled squeak. I looked up at him indignantly and he chuckled in response.

As we continued the movie, I could tell Jason was uncomfortable. He was a big guy, well over six foot with a muscular build. He was incredibly brave, to almost a foolhardy degree. Still, he had no stomach for horror. He blanched, looking as though he might be sick as the dog scene came on. "I don't know how you watch this shit," he grumbled. A fair assessment. I was admittedly a bit of a pussy. I cried at the drop of a hat and was terrified of just about anything. My addiction to horror games and movies was certainly an oddity. The night wore on, and as the movie was coming to a conclusion, I could hear the sound of raindrops against the glass pane of the nearby window. I grimaced bitterly. If there was one thing, I hated more than anything, it was rainstorms.

It was an aversion that formed in my later years, after the collision with Jason. I stared distantly as the images flooded into my mind. The car was overturned, the metal bent and twisted around us. The roof had buckled and shattered. I couldn't move my arm, shrapnel jutted from my shoulder. The sound of thunder, the flash of light illuminating Jason's motionless form. The shallow pool of water, slowly turning crimson. I had developed a pavlovian response to stormy weather. Even a light rain was enough to send me spiraling. A thunderous crack reverberated through the house, snapping me from my trance. I barely noticed the tears forming at the corner of my eyes. Jason must have noticed as he took me in his arms, soothingly stroking my head until I finally calmed down.

"Since when are you scared of storms?" Jason puzzled.

In the past we used to sit beneath the shelter of the porch, sharing a drink or smoke while the rain cascaded down around us. What used to be a regular pastime for us had become a nightmare in the time before I traveled back. I couldn't very well tell him the truth; I'd sound like a lunatic. "It's... complicated," I explained vaguely.

"Right," he responded with skepticism. "You changed a lot over the last couple days."

I simply nodded in agreement. Few things shape a person the way time and tragedy do. I was not the same rambunctious teenager he knew before. I laid in his embrace a while longer, reluctant to leave. Jason made no attempts to move me. He turned off the television and we sat in silence. At some point I drifted off in his arms. When I woke up, it was nearly midnight. At some point during the night, Jason's mother had left us a blanket at the side of the bed. On top of the blanket was a note, informing me that she had contacted my grandmother to let her know I'd be staying the night. It had been so long since I'd had a guardian to report to, the thought had barely crossed my mind.

I grabbed the blanket and headed to the door, intending to sleep on the downstairs couch. As my hand touched the knob, I heard Jason speak. "You don't have to go." His tone carried a note of concern.

"Jason... you know what I am, how I feel about you."

"I'm well aware," Jason responded resolutely.

I sighed, clutching the blanket firmly in my hands. "I don't think it's a good idea. It's fine that you don't see me the same way, but we can't keep doing stuff like this." As much as I wanted to take advantage of his presence, it seemed likely I was to stay in this bizarre reality. As it stood, I suspected our friendship would become unsustainable if we continued.

"I never said that."

"What?" I stared at him dumbfounded.

"This is all a little strange." He didn't know the half of it. Confessing my love and changing gender in the course of a week was one thing, being a fucking time traveler took it well beyond comprehension. "I won't pretend it's easy for me to understand, but I also never said that I wouldn't try."

"If it doesn't work out," I began, my voice shaking with uncertainty, "I-I can't lose you." Not again.

"I'm not going anywhere."

I hesitantly returned to the bed. "Even if you accept me, and even if you are willing to give this a shot, don't you think this is moving a little fast?"

"Harboring a secret crush since childhood is moving fast for you?" He teased. I punched his arm playfully.

"You know what I mean."

"I didn't expect it to be so hard to get you into my bed." He grinned impishly as my face flushed red. "Do you want to borrow a shirt to sleep in?"

I bit my lip. The offer was too tempting to pass up. "F-fine, but no peeking."

He offered me a baggy shirt from the dresser. He was over half foot taller than me, so the shirt fell just above my knees. I was grateful that I had taken the time to shave and pick out suitable underwear. I did not have the slight curves that hormones had provided in my later years, but in my current attire I still looked reasonably feminine. "The boyfriend shirt is a good look on you," he observed approvingly.

My face burned profusely. Even though I strived for his attention, it still came as a surprise when he looked at me with that lustful gaze. I felt a little ridiculous for getting so flustered. Though I was in a teenage body, I had lived long enough that such things shouldn't phase me. Unfortunately, my experiences with men were severely lacking, not to mention it was Jason of all people.

I climbed into bed, though I kept some space between us. The gap was quickly closed as Jason impatiently hooked his arm around me, pulling me in once more. I muffled a yelp, worried his parents might hear and come to investigate. I could hear his heart racing as he held me against his chest. At least it wasn't just me. Jason took shocking initiative as he began kissing tenderly at my neck. I gasped in surprise as his teeth dug in sharply, sending excited shivers rippling across my skin. I had not expected him to be so voracious, though I wasn't objecting by any means. It was around then that I felt something poke me from behind.

I moved my hips back, pressing up against him. His grip on my waist tightened. I wiggled my backside a little, causing him to groan as I giggled at his responsiveness. Below the covers his fingers traced along my legs. I squirmed at the sensation as his hand crept up my outer thigh and beneath the hem of the baggy shirt. He slipped his thumb beneath the waistband of my panties, snapping the fabric against my hips provocatively. He chuckled in satisfaction at my surprised squeak. I struggled to contain my excitement as the panties grew tight against my erection. His hand continued to wander, moving over to my growing bulge. I whimpered lasciviously as he took me in his covetous grip. I was never well endowed, but my sex felt particularly small when engulfed by his large hand. I was surprised at his willingness to go along with everything, and I certainly wasn't expecting him to touch me there.