Chapter 1 - Hello My name Is Tony

Second Chances by Emily

Posted on 8 Views / 660 Hits Word Count: 2731 (12 minutes)


Next Chapter 

Did you ever look back at your youth and fantasize about redoing it a second time with all of your future knowledge and experiences? What would you do if given a second chance? Would you take the path you didn’t take the first time?

That’s where my story starts. Or ends, depending on your point of view. Time travel gets confusing like that.

Friday, April 6, 2018

My name is Anthony Demarco. Friends and family call me Tony. You can call me Tony too since you’re reading this. I’m 37 years old, and as of this afternoon, I’m a divorced man.

My wife and I split as amicably as possible. After having been married for almost 3 years we both mutually came to the conclusion that we were no longer the right fit for each other. She claimed I never really loved her and I only settled down with her out of obligation.  While all of her friends were complaining that their boyfriends were taking too long to propose - I did.  I truly loved her, despite that crazy idea she had.  Maybe I didn’t show it enough.  Either way, I denied that accusation until the end. But a part of me - a very small part - wondered if she was right. Months after the wedding, the excitement started to fade and we realized we were different people heading in different directions. After the constant fights, there was a point where I stopped trying and the romance faded.

I mean, we’ve been separated for a while and I knew this was coming, but it still hurts.

I’ve always been more interested in my career. I’m a web designer for a local consulting company building applications for various non-tech companies. I actually love what I do. It’s been my hobby since I was a teenager. My only regret is that I work for someone else instead of myself. As such, I’m overworked and underpaid, and I’ve certainly been passed over for more than one promotion because I’m not out kissing up to upper management. There is a “game” to be played in “Corporate America”, and I refuse to play it.

When my marriage started crumbling, I buried my head into my work, which only made it crumble even faster. Today I signed the divorce papers.

I walked into my quiet house, threw down my keys and unopened mail, and fell down on the sole sofa in the living room. The house is quiet except for the hum of the heat. Pulling out my cell phone from my back pocket, I start to check my missed voicemails from the day.

“Hi Tony, it’s mom. I’m just calling to see how you’re doing. With all that is going on maybe you should take some time off to come visit. Me and Dad haven’t seen you in a long time.”

- Next Message -

“Hey man, It’s Ron. Just checking up on you. Why don’t we get together for drinks. Just us guys. Give me a call back. ”

- End of Messages -

I didn’t feel like calling either back right now. I was not looking forward to the inevitable guilt trip my mom is going to put on me. I already know the failed marriage is my fault. I didn't need her rubbing it in. I'm a grown-ass man. I don't need to run back to my parents when my social life crashes and burns. As for Ron, my best friend, I didn’t feel like driving the 40 minutes to his house right now. I wanted to wallow in my own self-pity. I reached over to check the mail. Bill, Junk, Bill, Circular. I got up to the kitchen and deposited them in the trash.

I turned to the fridge to fish out a beer. My fridge was practically empty. My wife hasn't lived here here in 3 months, so I wasn’t expecting a full fridge. I hadn’t been to the store in at least a week. I thought there was some leftover pizza in there. I guess I ate that last night. I was out of leftovers; out of beer. “Wonderful” I mumbled to myself, closing the fridge door.

When I closed the fridge door, a piece of card-stock fell down from the top of the fridge. It must’ve been moved off the front of the fridge during my wife’s move and shoved up top. It was a postcard invitation to my high school reunion. It was adorned with a red and black picture of my High School Mascot – the Bull.

“It’s Reunion Time!” the fancy text read. “The Class of 1998 officially invites you to our 20th High School Reunion.” The date read “Saturday, April 7th, 2018”. That’s tomorrow!

I recalled actually RSVPing to this months ago. Before my separation with my wife. I was actually looking forward to going to this with my wife in tow. “Well, there goes those plans!” I mumbled to myself.

Aside from my younger sister Cindy, the only person from High School I really kept in touch with was Ron. Everyone else I could care less about. I wasn’t very popular in high school. I was very much an introvert with one or two friends. Granted I was in the marching band, and Ron had peer pressured me into playing JV Tennis, but that was it. I never went to parties. I never had a girlfriend. Never dated. I barely went to the prom - and I remembered it was awkward and I didn’t enjoy it.

Despite not caring what those people from 20 years ago thought about me, there was a part of me that wanted to show up with a great job and a loving wife to show all of those losers that I turned out pretty cool. Well I certainly wasn’t going to go stag now.

"OK." I told myself. "Dinner Time. I could either order pizza for the 2nd time this week and Netflix and chill with myself, or I could go out to the pub and try to redeem my Friday night." I chose the latter. Only because I was out of beer too.

* * *

I walked into the local pub. It was a small hole in the wall I started coming to with my wife when we first moved here. They served pretty good burgers and some nights had live entertainment. Tonight I was just looking for dinner and a drink.

I took an open seat at the bar far away from everyone else. I looked around, and there were definitely people at tables eating and enjoying each other's company. Near the front right where I walked in, there were a few high school looking guys testing musical equipment. Great. I must’ve come during teen-night or something. A couple of bangs on a drum and some strums of the guitars to test the volume. Maybe this was a bad idea.

I flagged the bartender. A 20 something woman with green hair and green lipstick walked over. "What can I do for you?" She asked.

"I'll have that IPA on tap. And a shot of whiskey.", I responded. "Plus I was going to get a bacon cheese burger, lettuce tomatoes, Cooked Medium."

"Sure thing" she replied.

As she walked away to put my order in, a group of teenagers walked into the restaurant. A mix of guys and girls gathered around the 2 guys setting up. High-fives and fist bumps. Clearly they knew each other.

The TVs were tuned to ESPN and CNN. I wasn't interested in any spring sports, and CNN was talking politics. 

My beer and shot arrived at that moment. I picked up the shot glass, tapped the bar-top with the glass and downed it.

The band started to play a cover of a Chainsmokers song and the teens in the front cheered. I ate the burger and while glancing up at the TV on the wall seeing if there’s anything new up there.

ESPN was talking about the up and coming NFL draft in a few weeks and the various college prospects. Having been raised in New Jersey, I was a New York Giants fan, so I had my favorites on who they should pick. The experts had differing opinions.

I washed the burger down with my beer.

I glanced back to the teens. They were nothing but smiles. There was one couple holding hands as if this was their date night. One guy was playing on his phone. Another guy was using his phone to video record the performance. One girl was just staring at the lead singer lost in her own world. The lead singer was definitely staring back at her as if he was singing directly to her.

I made eye contact with the bartender who was delivering a tray of sodas to the teens. I made a scribble motion on my hand to indicate I wanted the check. She came by shortly with the bill and I handed her my credit card.

“I didn't expect it to be teen night.” I said to the bartender.

"Yeah", she said, "Typically we'd have them in here during the week, but the schedule got a little messed up. They seem to be behaving themselves. This seems to be one of the better bands anyway."

"Well, at least they're having more fun than I am." I stated.

"Whoa" she said, "Was my service that bad?"

Realizing I had just insulted her, I back tracked. "Oh no. That's not what I mean at all. I'm just having a bad day. Was hoping for just a little quiet time."

"I see." she said, about to turn away.

I felt stupid as if I had to explain myself and I continued. "I mean look at them. Not a care in the world. The girl and the singer are clearly eye fucking in public!"

She turned back towards me with her eyebrow raised. Clearly I just spewed word vomit. Maybe this is why I have a hard time talking to people.

“Envious?” she stated.

“Pardon?” I replied.

"You’re stuck in a rut" she continued, "and you’re envious of that group over there having fun. Didn't you do the same thing when you were their age?”

“Well I was in a rut then too. Just seeing them brings back some memories of when I was them. It was a frustrating time for me”

"Well, teenagers are horny and in a perpetual state of frustration. What made you any different?"

"I was an introvert. I wanted to socialize. I just couldn't. I was paralyzed from saying the right thing and putting myself out there. I rarely took risks. I settled on what was comfortable. I was comfortable staying on the sidelines."

She didn't say anything and let me continue.

"Maybe if I did things differently I wouldn’t be in such a rut today. Man, if I could do it all over again - with the last 20 years of experience - things would be different."

"Oh really?" She was intrigued. "What would you do differently?"

"Oh I'd be more outgoing."

"You actually seem outgoing to me right now" She said. "You're clearly lacking confidence from whatever bad day you had. Are you sure you're as introverted as you're saying?"

"Well, I slowly started coming out of my shell during and after college. I found a group of friends that pushed me out of my shell. I got a job, and money. I was pressured into joining my company softball team. That’s where I met my wife – I mean ex-wife. I really didn't date anyone until I met her a few years ago. I was just too introverted and too concerned with how people viewed me to take risks."

"So Mr. Outgoing" she said, moving closer to me. "If you had to do it all over again, what would you do differently?"

It took me a moment to think. But I knew the answer. "I wanted to date more. Join more things. Go to parties. Put myself out there. Enjoy my youth. Somewhere inside me there's a 17 year old screaming that he missed out on.. something..." I let my voice trail off and I glanced back at the teens.

There was silence for a few moments, and the bartender walked away with a smile.

"Dammit Tony," I thought to myself. "You just spilled your guts to a woman you just met. Can you be any less awkward?"

The bartender came back with another shot. This shot glass has a neon pink drink in it. "This one is on the house." she offered.

I moved my head closer to the glass and stared at the liquid. "What is it?"

"Just a little pick me up for times like these. My own recipe" she stated and walked away.

I turned back to the shot, and picked it up. "Cheers!" I said as I downed it. It was fruity. It reminded me of a tropical drink, but I couldn't quite place what drink it was. I hope it wasn't tequila.

The bartender returned with my credit card and receipt without saying any more words. I scribbled my signature and left her a good tip as well. I walked out of the restaurant the same way I came, passing the group of teenagers and the band members who were laughing and smiling and jamming out to a new song.

I didn't know what was in that shot, but by time I walked through the front door of my house, I was woozy. I started disrobing my clothes and crawled into bed with just my boxer shorts on. It didn't take but a few minutes to completely pass out.

* * *

My alarm was buzzing.

Wait, that's not right. My cell phone's alarm isn't a buzzer.

The buzzing is coming from my left side, so I roll over and see what it is. I slowly open my eyes a little bit, and I see red LED lights displaying "5:45". I kick my feet out of bed to reach it and turn it off. After fiddling with the clock and pressing a few buttons, I find the one that silences the alarm.

Now that the buzzing is over I sit back on the edge of the bed for a moment and try to catch my bearings. There's a hair in my mouth. I blow it out and wipe my face.

The room is dark except for faint street lights coming from the window behind me. I see the slight outline of the room.

This is wrong. But familiar. I reach back under the pillow for my cellphone to shine the flashlight but I feel nothing under the pillow.

This almost resembles my childhood bedroom back home. But that's impossible. I got out of bed and walked to where I believed the light switch to be near the door.

The light is blinding. As my eyes adjust I look around to inspect my surroundings.

This does look like my childhood room. Almost. The placement of the bed and night stand. The closet. The model of the USS Enterprise on the shelf. But the walls are purple instead of blue. Instead of a tall dresser in the corner, is a wide dresser with an attached mirror. The disheveled comforter on the bed is a grey and purple pattern. The rug is a newer pastel blue instead of the worn green shag carpet that my parents never replaced for me.

This can’t be my parent’s house. My parents moved away 15 years ago.  Why does this look like a girl’s room?

"This isn’t right. Where am I?" I mumble to myself. "I have to get out of here." I say as I walk around the room to see if I can find my clothes. I know I left them on the floor last night. I get on my hands and knees and notice something else.

What am I wearing?

Speaking of clothes. I clearly remember going to sleep in boxers, yet I'm wearing a t-shirt. I look down to examine it. Instantly I noticed two bumps protruding out my gray t-shirt.

I grabbed them and I realized this is indeed my chest.


I rushed to that dresser mirror and looked in it. Staring back at me was a teenage girl with a shocked expression.

Next Chapter 


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

Leave a Comment

You need to logged-in to leave a comment. Register | Log in

More Series from Emily