"You’re a Girl Now?" Ch. 01-03

[All featured in this story are above the age of 18]

Chapter I:

It had been more than a year since Flint had left for the military. We were best friends since we were babies. Our mothers were high school friends and we only lived a few houses down from each other our entire lives.

Between the two of us, all eyes were on Flint. He was taller, with broad shoulders, with a chiseled face, and extremely physically fit. He was a swimmer all through high school and with his shirt off, he looked like a superhero. This was true even before he enlisted.

Even more so when he returned. He was more toned and lean. The shaggy dark brown hair he left with came back as a clean cut medium fade that left a few inches on the top. His face was clean shaven and it was a good look for him, considering he was always frustratingly handsome.

But the trait I admired most about him was that he is the kindest person I have ever met. Popularity and being a total jock didn't change him in the slightest. He would go to swimming or wrestling practice and then in the evening, complain about how sore he was in my living room while we played video games or watched anime together. Even as we grew more different as we aged, we never stopped being best friends.

I was the complete opposite with a short and slender frame. My voice was high pitched and I was always considered somewhat effeminate. When I tried to get into sports with Flint in high school, I just couldn't make the cut. He even tried to coach me through a rigorous diet and workout routine but it wasn't very successful. He was just... more manly... and I never came close. My family insisted I was a late bloomer but every year, the outlook seemed more and more bleak.

There was part of me that was jealous, of course. He was always so confident. When he posted photos on social media, he was never modest in showing off his abs, posing with a fish he speared in Okinawa, or even the occasional salacious grey sweatpants photo... which revealed yet another masculine arena where he had bested me.

But I was also happy for him. He was living an adventurous life and he was the kind of guy one would expect to become a senator or something. He was just so... perfect.

There was a point where I stopped trying. I was never really comfortable in my own skin like Flint. When we changed in the locker room in front of other boys, my face would turn red at the prospect of even taking my shirt off... God forbid taking a shower with my classmates. Pools were difficult for me because I could at least justify wearing a wetsuit at the beach. Even when I was all by myself, I had a hard time even looking at myself in the mirror. All my life was haunted by this strange feeling of vulnerability and uneasiness.

I understood why fairly early on but was afraid to share that part of myself with anybody, Flint included. Even though we lived in a somewhat open minded place on the West Coast, it is a lot. I was raised as a boy and the masculine ego is fragile. What little manliness I did have, I guarded jealously. The thought of coming out scared me.

With Flint gone after graduation, I sank into this deep loneliness. We still communicated frequently and sometimes played games together online when our schedules allowed. I missed him more than I ever thought I would.

But with him out of my immediate vicinity, I felt more emboldened to do things like grow my light brown hair out. I followed tutorials online to perfect the art of accenting my light blue eyes with cat-eye mascara. My wardrobe changed from baggy hoodies and skinny jeans to sundresses, short shorts and thigh high stockings. I "passed" even before I began hormone replacement therapy.

I cried a lot. Not just because I was depressed or the effect the hormones would have on me. But because the answer was right in front of me all my life. I didn't need to be like Flint. I was never meant to be.

Better yet, it was the first time in my life where I felt attractive. Comfortable. Right. I was actually good at something, even if it was so superficial as convincing people who never met me before I had been a girl all my life, it was a win. And it felt great.

However, I was still terrified of what Flint might think. Not once did I mention it to him during his time away. My already soft voice became even more feminized but he never really seemed to notice when we were playing games with voice chat. I evaded any discussions about my personal life and most of my social media presence was text-based.

After all, he was a bro- a military guy at that. Every now and again throughout our life, he would make a comment here and there how something was "gay" and was very protective of his heterosexuality. In fact, he often deflected that same accusation against me and told our classmates I was "slaying pussy" and that I was too much of a gentleman to kiss and tell.

I was riddled with anxiety about what he might think. When he did return, I texted him still but I dodged plans to hang out when he made the suggestion.

"Dude when are we going to hang out?" He texted me. By that time, he had been home for two days. "Is everything ok?"

"Sorry! Been busy with work!" I typed back. "I'm trying to find a needle in a haystack with this code." I hit send but cringed that I was only delaying the inevitable.

"Are you sure everything is ok?" He immediately replied. "We can at least do dinner or some shit. I'll pay. I'll pick you up in 30."

Fuck... what do I do? "Actually how about I meet you at Giacamo's? I'm feeling Italian." My hand trembled as it pressed the send button. There was no going back. I decided that it was better to get it over with than for him to think something was wrong or that I was upset with him.

"Mama mf mia bro. See you there." His message popped up on my screen with a bunch of pasta, chef, and tomato emojis.

The truth was that I was already at Giacamo's. I had gone alone and just sat down when he messaged me. "Actually, I'm waiting for a friend if that's ok? Maybe twenty-ish minutes? I'm sorry!" I told waiter but he waved it off.

"Don't worry about it bella, let me know when you're ready," said the waiter and my heart fluttered from how thoughtlessly he called me a pet name and then he said "you look like you're waiting for a boy. I can see it on your face. First date?"

"Oh no! Just a friend!" I clarified and blushed uncontrollably. The waiter shot me a smug look and nodded before tending to the other guests.

My phone vibrated on the table with another text. "Dude there's a cute girl here, want me to talk you up?" I looked around the restaurant and saw that there was nobody else who fit that description. Directly across from the booth, I saw him through the window chatting with the host. "Do you want a booth or a table bro?" He texted as I watched the host lead him to a table right next to mine.

I hid my face behind my hand and grit my teeth. My heart pounded and I began to feel dizzy. When I finally summed up the courage to look up, he was standing in front of my booth.

He was wearing an navy blue ugly knit Christmas sweater pattered with white snowflakes. His hair was neatly combed and dapper and with the slight stubble on his face, he looked classically handsome as ever.

"I'm waiting for a friend but I would regret it if I didn't talk to you before you left," he said. The way he looked at me with his kind hazel eyes made me melt in my seat.

"I... uhm..." I struggled to find any coherent thing to say. "Flint..?"

"Have we met before?" He raised an eyebrow and leaned closer to inspect me. As he did, he saw my phone lying face up on the table displaying a text from him.

"No way!" He said out loud. "That's why! He's busy hah!" Then he reached out his hand and took mine and shook it. "My name is Flint Greene. I'm a close friend of Sam's. Where is he? Why hasn't he told me?" He looked toward the restroom. "Can I wait here with you?"

"Flint... I..." I stammered and held my hand out and said "yeah... why don't you sit down?"

"Are you ok?" He asked and sat across the table from me.

"Flint, it's me," I said quickly and cringed. I braced myself for some dramatic outburst but it didn't come.

He was laughing. "That's great! So what is Sam hiding around the corner recording this or something?" He chuckled and craned his neck to search the bistro.

"It isn't a joke. It's me. Sam," I choked out. A chill washed over me and I looked down at my thighs which were shivering despite my stockings.

He squinted and leaned closer. "Really?" His voice was skeptical but I could see on his face that he was beginning to recognize me.

"You have a scar on your back from hopping the fence to the school pool," I blurted out. "You were taking Megan there in the middle of the night but you lied about it to everyone because Megan had a boyfriend at the time."

"Oh my God," he gasped before sitting back in his seat. His eyebrows furrowed and he just stared at me in awkward silence. After what felt like an eternity, he finally asked "you're a girl now?"

"Yeah... I have been for a long time, actually," I confessed and pulled the hem of my skirt further down my thighs. It was impossible for me to look directly at him and my eyes were getting so teary that I couldn't see.

"Dude..." he sighed and laced his fingers together behind his head. "Why didn't you tell me? I thought we were friends..."

"I was worried what you might think... I don't know..." I began to cry. "I just... didn't want to lose you as a friend. People in my own family don't talk to me anymore. I didn't want to lose you too."

"So you were just going to avoid hanging out in person forever? What if I didn't insist this evening? Would you have blown me off all Christmas?" His eyes were surprisingly glassy also. When he spoke, his voice was shaky and I was stunned by his reaction. I expected him to be upset. Disgusted. Angry, even. To call me names or disown me. But instead, he was hurt that I kept this secret from him. He continued "all these years br- Sam. All these years, I was that time we spent at the gym or trying to set you up... you were living a lie and I was making it worse? You didn't tell me! You're my best friend. This doesn't change that."

"I had a hard time just admitting this to myself," I said quietly. "Telling people who were in my life before... it's hard. Painful sometimes."

"It all makes sense now," he mumbled and looked off into the distance for a moment before looking back at me. "Are you happier now?"

"You have no idea. My only regret is not doing it sooner," I responded and when I saw his concerned expression I added "and not telling you sooner."

"I'm sorry I gave you the impression that you couldn't. It's not really my place to get mad at you about this. It's one of those things right? Like having a baby or something. You get to decide when to tell people," he said and looked down at his huge hands resting on the table. "And I'm sorry I sort of forced you to tell me before you were ready."

"It's not your fault," I told him. Inside me was a wild tempest of emotions. "Probably a good thing you did, anyway. Otherwise we might not have hung out."

"Yeah, now you're stuck with me until I have to go back," he laughed and then covered his face with his hands and groaned "I can't believe I was about to hit on you."

The chill that had overtaken me only a few minutes before quickly turned to heat. I felt my cheeks and ears burning. It was a weird feeling. Awkward. But also endearing. Reassuring.

"Have you two had a chance to look at the menu?" The waiter asked, causing both of us to jump.

We kept it casual over dinner and he told me tales of his new exciting career in the military. I told him about how I cheesed my way into a software design job. He asked about the fates of some doomed high school romances of our mutual friends. All the while, he avoided the subject of my transition but I didn't get the impression that it made him uncomfortable or that anything had changed between us really.

The evening turned into night and we left Giacamo's to walk off our food down the main street of our town. There were bare trees that lined the avenue in sidewalk planters that were strung with Christmas lights. It was cold enough to see our breath, but not so cold that it was unbearable.

He walked on the street side of the sidewalk with his hands in his pockets. "You know, it really suits you," he said after a while and then flashed me a weak smile. "I'm glad you can be... you, and all. And you can be whatever you want and that's ok. Look and dress however you want. But you know what, Sam?"

"What's that?"

"You're really beautiful."

Chapter II:

I was nervous to see Flint again. But this was a different kind of nervous. The emotional roller coaster that was coming out to him mellowed out by the next morning. It was an excited sort of nervous the next day.

Our town just opened a new ice skating rink and Flint had talked me into going with him. The problem was that where we lived in California, it never really snowed. Ice skating was a completely new thing for both of us and I had no clue what to expect.

I dressed the part with my grey pea coat over a maroon knit turtleneck sweater, a black, grey and red plaid skirt, a pair of black leggings and red socks pulled up to my knees. That day, I wore my shoulder length light brown hair down to show off the tips turning blonde. I went light on the make-up but I couldn't resist the cat-eye which I was proud to have perfected.

Flint dressed a lot more attractively as well. He wore a pair of blue jeans that fit him extremely well in all the right places, a black and grey flannel which he wore over a grey hoodie. I couldn't help but laugh when he insisted on wearing a Santa hat as we stepped out into the rink.

I pushed off and managed to keep my balance, much to my surprise. Flint, on the other hand, could hardly keep his feet under him and cling to the side rail for dear life.

When he did eventually try to push off, his feet slid back and forth like a cartoon character. "Jesus fucking Christ!" He yelled out, which solicited dirty looks from a family skating by. "Jesus! Happy birthday Jesus. Jesus Christ..." he corrected himself and held his hands out to try to balance and laughed. "No way this is your first time," he said when he saw me gliding slightly more gracefully past him.

"No, this is a first... I've rollerbladed before... kind of like that, but colder," I said and shuffled back toward him. He began to slip and he grabbed my hand and pulled me down with him. I landed on his chest and he found that very amusing. His chest was tight and warm. I could smell his cologne and wondered when he started wearing any scents at all.

"I have no clue how to get back up," he said and pat me on the back. "I need you to help me," he laughed. I scrambled to my feet and held both of his hands while he stumbled to a stand. Then he held the guard rail with one hand and mine in the other.

It was the first time I was better than him at something that didn't involve a microchip. But he didn't seem to feel the least bit ashamed at his clumsiness on the ice. All afternoon, he clung to me in one way or another.

First he held my hand. Then his arm was around my shoulder. There were even a few times he wrapped his arm around my waist and pulled me closer to him.

When I looked up at him every time he did this, I didn't get the impression that he even realized what he was doing. It seemed almost subconscious for him. Instinctual. He was never very physical with me before aside from the occasional rough housing. But this was different. He took every opportunity to get closer to me but I never once felt like it was deliberate. It all felt so natural.

While he left to turn in our skates, I went to get us both hot chocolate. The clerk behind the counter smiled a lot while we talked and he even cracked a few jokes. Flint returned and saw me laughing.

He put his arm around my shoulder and asked "did you order yet?" And then he looked at the clerk "I'll have a croissant too, please." He smiled and the clerk's mood seemed to deflate quickly in Flint's presence.

"So I meant to ask," he said as we found a table in the plaza near the rink. "Do you still go by Sam? Or do you have a different name now? I was reading last night that you're not supposed to call people by their old names?"

"Well officially, it is Samantha. Not much of a change but Sam still works," I explained and brushed my hair behind my ear. We had parted ways the previous night pretty late. He was reading up on this last night? Did he even sleep? "But if I had, like say, dude's name..."

"Like Dick," he suggested with a chuckle.

"Like Flint!" I retorted and stuck my tongue out at him and continued "Yeah I'd probably go by a different name."

He nodded and took a sip from his drink. "Hey, I hope it doesn't make you uncomfortable if I have questions. If it does, just tell me now and I'll drop it forever," he said with a suddenly sincere tone.

"Everyone has questions, I'm used to it. It's fine," I said and reached over and pat his hand. "Whatever you ask... I guarantee you I've probably been asked weirder questions already."

"Thanks, but I don't want it to be, like, you know... Intrusive," he replied and took my hand in his. It seemed so effortless for him. So much that he didn't even acknowledge how affectionate he was being with me.

"I want to share this part of my life with you. You're my best friend and honestly, it feels good to talk about it with someone who knows me," I said and gripped his hand tightly, but it still didn't fase him.

"That's the thing Sam. I want to know you," he told me and then scooted his chair next to mine and closed the distance between us. "I want to know the Sam who has been hiding out all these years. Yeah, I'm closer with you than I am with anybody else but it also feels like I'm meeting the real you for the first time. I want to know who she is."

"Flint, you can ask me anything. I want you to," I said and smiled back at him. "It's ok."

"Do you still like girls? Did you ever?"

"Yeah, I suppose. It does feel a little different now. I still find them attractive, sure. But I also like men, too," I answered and felt my cheeks burning again.

"Did you always like men?" He asked immediately after.

"Yeah. But definitely a lot more now. Like, a lot a lot more," I replied and leaned against him. Still, his reaction was simply to put his arm around me and I saw the clerk behind the counter staring daggers at him.

"So when I tried to set you up with chicks, you weren't just... going along with it. You liked them too?" He seemed concerned and followed up with "I hope I wasn't you know... making it worse." He stood up and took my hand.

When he pulled me up, he held is arm out for me and I locked my elbow in his. "Does this feel weird to you, Flint?" I finally asked. The mystery of where his thoughts were at was killing me.

"Why would it? This is how you walk with a girl, right?" He responded without skipping a beat. "I guess I lied a little bit when I said this doesn't change things. I'm not gonna treat you like a guy anymore. It would be more weird for me if I did, if I'm being honest."

"Well I'm sure your girlfriends might be jealous, then. That you're such good friends with another girl," I teased and leaned my head into his shoulder.

"I'm not really thinking about other girls," he said quietly. He led me to a footbridge that overlooked a small canal that cut through the city. The sky was cloudy and the air was cool and thick. A breeze picked up and even being bundled up, I still felt the chill wash through me.

"What are you thinking about?" I asked and stepped closer to him to shield me from the wind.