Friendship in Transition


*Originally posted in Romance, moved here. Contains LGBTQ+ themes*

Hey everyone. My name is Dan, and this is a story about me and my best friend Jimmy.

Jimmy and I had been best friends our whole lives, ever since we were little kids. I was an only child and Jimmy had only a sister, so we saw each other almost like brothers growing up.

Jimmy was an awesome combination of being really spontaneous at times, to laser focused at others. We could be dying of laughter as he would just run around making weird noises, then half an hour later he could sit on the floor for hours taking apart his parent’s computer for the 100th time making it run just that little bit better so we could play the latest titles. He was always really successful in the things he did but never took his accomplishments or himself too seriously.

Our parents were also good friends and moved in the same social circles, which was how we met so young. Our families often went out to dinner together, and sometimes the seven of us would even cram into one minivan and go on vacations together. When we stayed overnight in a hotel the adults would share one room with two beds, and we kids would share another. Jimmy’s sister, Kayla, would get her own bed, while Jimmy and I would share the other. We enjoyed sharing a room like actual brothers. Even having Kayla there was ok, she wasn’t too annoying and it really felt like we were a family.

As we grew up and began to hit puberty and I found myself seeing girls differently than I used to, it also started to become clear to pretty much everyone, Jimmy included, that he was not interested in girls, but boys. Maybe the adults already knew even before that; in fact, looking back on it, I’m sure they did.

Jimmy always used to wear girls sneakers. He told everyone it was because they were the only ones that fit him correctly (he was always small for his age), but he also told me in secret it was because pink and sparkles were his two favorite colors. He also always wore his sun washed blond hair long, down to his shoulders at least. There were dozens of other signs that I’m sure anyone who’s witnessed a young person realize they’re not quite like everyone else would recognize.

This didn’t put any kind of strain on our friendship, if anything Jimmy coming out in early high school made our bond even closer. I wasn’t any older than Jimmy, but I felt a sort of big brother protectiveness over him. Jimmy was small, I was big. Jimmy was effeminate, I was masculine. We grew up attending a liberal suburban school in California so maybe the shit Jimmy had to take from bigoted idiots wasn’t as bad as it could have been, but there’s pretty much no escaping some level of high school harassment. I tried to always be there for Jimmy even if there wasn’t much I could do to protect him from idiot remarks.

Some time in maybe junior year or the summer after Jimmy confided to me that he felt like he was supposed to be a girl. He said he’d known it for some time, and that I was the first person outside his parents he’d ever told. I was actually really moved that Jimmy trusted me so much, and I tried to be as supportive as I could.

Jimmy told me that he’d actually already been taking something called puberty blockers, and soon was going to be moving to full fledged HRT therapy. He started going by Jamie, began wearing exclusively girls clothes, and wanted to be referred to with female pronouns. This caught me off guard.

As Jimmy started to become Jamie I knew that she was still my best friend who I’d grown up with all my life, who was like a brother to me, only now she was my sister. Nonetheless, there was a cognitive dissonance within me (I was too young and dumb to even consider how much worse this must have been for Jamie at the time). As Jimmy transitioned more deeply into being Jamie, and I remember thinking it seemed to happen much faster than I’d anticipated, I felt like I was losing Jimmy. It felt like Jamie was a new person and not quite Jimmy anymore.

I’m ashamed to even say this now looking back, but I began to resent Jamie for taking Jimmy from me. For just a little while, and for the first time ever since before either of us could remember, Jamie and I drifted apart. And it sucked.

For a few months, somewhere in the middle of senior year, Jamie and I rarely spoke. I saw her around school, but I found ways to avoid her. I knew it was childish, but I was a dumb teenager who felt like he was losing his best friend and brother. During this time Jamie started taking hormones to aid in her transition. She was never very masculine; even pre-transition she was petite, had no hair on her torso to speak of, and was only about five foot four. In the right clothes and with makeup she barely even needed hormones to look like a born girl.

I think this helped her dive headfirst into the female social circles at school. It seemed like almost no time had passed and Jimmy was just a memory to me, replaced by Jamie who had taken to her new identity as if it mardin escort had always been (which, of course, it had).

One evening, and it had maybe been a month since I’d said even one word to Jamie, my laptop was having issues. It kept overheating and powering down the moment I tried to run anything even slightly demanding on it despite the fans clearly pumping as hard as they could. My own nerdism tended toward the fantasy, literature, and RPG variety; I didn’t really know much about computers. I was worried my parents wouldn’t bother getting it fixed or replaced, and I didn’t have money enough of my own to have it taken care of. So I opened my phone (this was just as society was getting to a time when teenagers were starting to get flip phones or bricks of their own), pulled up my text messages, and looked at my conversation with Jamie, who was still listed as “Jimmy” in my phone.

The last four messages, from the previous few weeks, were all Jamie reaching out to me. She wasn’t saying anything mean or resentful, just normal stuff like “hey, wanna hang and play WoW tomorrow night?” And, asshole that I was, I’d just not responded.

I started to get choked up, there was a lump in my throat. My angsty hormonal emotions were running hard and I felt an awkward and terrible combination of anger at Jamie and shame with myself. I just stared at the conversation trying not to cry, trying to think of what to say, what I could possibly say after being such an aloof dick, contemplating if I even ever wanted to see or face Jamie again.

Finally I just sent her a message.

“My computer’s fucked. Can you fix it?”

The reply came within a minute while I was still looking at the message I’d sent at my phone.

“I’ll take a look at it man! Want me to come over?”


And that was it. My best friend was coming over for the first time in months, when throughout our lives to that point we had been with each other almost every day, or at least it felt like it.

Not ten minutes later I heard the familiar sound of Jamie’s mid ’90s Buick Century, a hand-me-down from her grandma or something, pulling up to the house. It had an exhaust leak and clicked like The Wheel of Fortune.

I heard the engine turn off and the door close with a clang. A few seconds later the doorbell rang. I was still feeling extremely emotional and now began to worry about Jamie seeing me like this. My dad opened the door and I heard him speaking, I don’t know what he said but from one floor down and my closed bedroom door he sounded like he was being overly friendly. And then there was a knock on my door, timid, not like Jimmy’s knock which was really just a formality as he opened the door at the same time.

I tried to say “come in.” but I couldn’t make my voice work without cracking, so I got up and opened the door. I looked at Jamie, she had a nervous smile on her face. She was clearly happy to see me but scared how I’d act. I hated myself for that. I was so happy to see her too, if only I could have gotten over my dumb anger and told her how much I’d missed her.

In her face I still saw mostly Jimmy behind the makeup, but her presence was now Jamie through and through. She was wearing womens jeans with silver embroideries along the pocket seams, and a “For the Horde” sweatshirt. Her bleached blonde hair was definitively styled in a trendy teen-girl fashion, and she was still wearing the makeup she’d probably done before school that day. I couldn’t help but notice she looked quite cute.

I quashed that thought as hard as I could.

“Come in.” I said in a whisper, not trusting my voice just yet.

Jamie came in, and I closed the door after her. I sat on my bed, and she sat on the desk chair in front of where my laptop was positioned, setting her big backpack down as she did so.

Jamie turned to me hesitantly, I know I wasn’t hiding my inner turmoil at all as I stared at the floor.

“I brought my shit to fix it, what’s wrong with the cranky old bitch?”

And there was my best friend. I heard her voice, a bit higher than I was used to it being, but it was the same voice. The same mannerisms. The same irreverent use of foul language.

And I broke down.

Tears filled my eyes immediately and I looked up at Jamie. I couldn’t speak, but I hoped the words “I’m sorry” were written on my face. I really hoped they were.

Jamie instantly moved over to sit on the bed next to me and wrapped her arms around me tightly.

“Dude, it’s ok.” she said, and she was crying too.

I hugger her back hard and buried my sobbing face into her shoulder. I couldn’t bring myself to say anything yet, I just let my emotions flow out through my tears and onto her black World of Warcraft sweatshirt.

“I’m sorry, Dan.” Jamie said through her own sobs. “I know shit’s been fucked up lately. I’m so fucking sorry what I’m doing has hurt you.”

And now I was angry enough to overcome my silence.

“Shut van escort the fuck up!” I said through ragged breaths, absolutely furious with myself. More mad at myself than I’d ever been at anyone, I could barely talk, stuttering the words out through a lump in my throat the size of a softball. “Shut the fuck up! Don’t ever be fucking sorry to me or anyone for being who you are. I’m a fucking asshole and I’m sorry. Don’t you be fucking sorry to me.”

And then for a long time there weren’t any words. We just hugged and cried together. The only other time we’d done that was when my old dog Peppers had died when we were about eleven.

When we’d finally cried it all out and wiped off our sobby faces we just started laughing at ourselves, it suddenly all felt so ridiculous.

“Can we just pretend this all never happened?” I asked with a sheepish smile.

“Done, bitch.” Answered Jamie, and we both laughed again.

Jamie then got to work fixing my computer. Turned out it was just all clogged up with cat hair on the inside, so about five minutes and some compressed air later and we were sitting in my room on our respective laptops playing video games together just like we always had, yelling obscenities at virtual enemies while drinking Mountain Dew.

We stayed up way too late for a school night, but I think my parents knew our friendship had been struggling lately and they gave us space to just relax and be friends again.

As Jamie finally packed up to go home I realized I was astonished at just how fast my brain switched over now to seeing her as a girl when before it had refused so stubbornly to accept my friend’s change. How she moved was feminine, how she looked was feminine. And then when she finally went home I watched her walk down the stairs to the front door, and I noticed her ass in those skinny girl jeans. God help me, she looked hot from behind; her tight butt bouncing coquettishly with each step down.

‘Noooooope’ my braid said to itself.

‘Yeeeeeep’ my cock said back.

I was tired, I went to bed, and I forced myself to simply go to sleep. As a horny teenager nightly wank sessions were pretty regular, but I knew where my thoughts would go if I tried right then, and I just wasn’t ready for that. Sleep was what I needed, and so that’s what I did.

For the last few months of high school my friendship with Jamie was as strong as it’d ever been, we were hanging out all the time. We heard the odd jibe from idiots here and there, comments about us being boyfriends or even girlfriends (morons don’t often make much sense). When earlier in our high school days I’d occasionally try to fight some motherfuckers over their homophobic comments, Jamie and I both found that we were paying less attention to the shitheads even as their numbers and comments seemed to diminish. We were all about to graduate and move on into the real world, and even in high school it seemed most people had matured beyond outwardly childish behavior.

Those last few months of school and the summer which followed it were great times. I still felt pretty responsibility free, and decided to spend most of my last summer before college fucking off.

Jamie, however, had decided not to go to college right away. She’d been promoted to being a manager at the tech store where she worked fixing computers and phones and stuff. She decided to work there and get some money while taking online computer cert and programming classes. My college was a few hours from my hometown, still in California but I wouldn’t be visiting back home very regularly. Jamie and I promised each other we’d stay in close contact online and through video games.

So I went to college, and Jamie stayed back home to work.

Jamie and I had never in our friendship discussed our romantic relationships much. I’d met a couple guys Jamie had dated when she was Jimmy, and she’d met a couple girls I’d dated. Neither of us had ever been in a serious relationship though. This is a trend I continued into college. I fooled around a bit, but really I found myself too busy with both school and extracurriculars (of the non-sexual variety) to find anything like a steady relationship.

Sometimes when we were chatting over text, or whatever, Jamie would mention her lack of a boyfriend. She said she was busy with work and the online classes she was taking, and also that she was still getting comfortable with her changing body and sometimes lacked confidence.

This was weird to me because she’d always been pretty confident. I tried to be supportive of her, though I didn’t really know how very well. That’s when I started to tell her how good I thought she looked.

“I’ve seen your photos on Facebook and shit, you’re looking really beautiful!” I’d say.

“You really think so?” She’d ask.

“Yea, definitely!” I’d reply.

And it was true, she was getting sexier in my eyes by the day. Her facial features were softening and her body looking more feminine. ankara escort It felt weird to accept that I was now starting to see Jamie in a sexual way, but I think being physically apart from each other made the shift in my perception of her easier somehow. I mostly just tried not to think about it too much. She was still Jamie, my best friend, but damn my best friend was looking hot these days.

Then one day she sent me a somewhat unusual message.

“Hey.” she’d written in the message. “If I send you something kinda weird will you promise not to be weirded out?”

“Hahaha, sure why not? Go for it.” I responded.

And what I received from her made my jaw drop.

“My first ever bikini!” She said, and attached a photo of herself in a red bikini.

I was flabbergasted. She had her long light blonde hair down and parted, slightly covering one side of her face seductively. The bikini was nothing crazy, but the body which wore it was… well, it was fucking sexy. Jamie had always struggled to tan even in the California sun, tending to burn readily. As such, she’d always worn a ton of sunscreen and been pretty pale.

Showing on the 90% of her body that wasn’t covered by red bikini was smooth alabaster skin over a lean body. Hinted at under the red fabric were a couple more very feminine things; on her chest Jamie was starting to show the hints of natural breasts forming small mounds under her top. The visible curve of them where the bikini top allowed for cleavage was utterly alluring.

And then there was what showed under the bikini bottoms. Hiding beneath the tight red cloth was clearly a small bulge. I found my eyes drawn down, and I felt my own bulge begin to expand.

What the fuck? Why was that so sexy to me? I didn’t know why her bulge seemed so naughty and attractive, but it did.

Then she sent a second picture.

“I have no idea how this tucking shit is supposed to work yet! Where the fuck is it supposed to tuck to!? *crying laughing emoji*” and with the message was a picture of her ass, the bikini showing the lower curves of her pale round cheeks.

Holy shit. I’d been trying to hide it from myself. I’d tried to put it out of my mind. I didn’t want to think about it, it almost seemed wrong somehow. But there was no denying it; I wanted to fuck Jamie. I wanted to strip off and rail my lifelong best friend.

Nevermind that I was still only 19 and pretty much wanted to rail everything, but there was no fighting the natural attraction which existed within me towards Jamie who was now an objectively hot chick.

“FUCK THE TUCK JUST LET IT ALL HANG OUT FOR HARAMBE!” I decided to say in response, trying to think of anything which would move the conversation in a direction that wasn’t focused on how my best friend was giving me a hardon, even if that direction was memey non sequiturs.

“DICKS OUT!” she replied back with an attached picture of the eponymous gorilla given the soft focus treatment.

From there our conversation reverted to the normal. That night, however, for the first of many times, I jacked off looking at pictures of Jamie. It felt like such a dark secret, I couldn’t bear it if she found out. It felt like betrayal. But those feelings didn’t stop me.

From that night on our conversations started having a noticeable hint of flirtation in them. Everyone’s been there:

After losing in some online game…

“Fuck you! Suck my cock!”

“You gonna make me?”

“Maybe I will.”

“You’d like that, wouldn’t you?”

Shit like that. We also started sending each other photos of ourselves more often. It felt like a game of who was going to say the next most sexually explicit thing, or who was going to send the next most provocative picture.

We’d send pictures after our respective workouts, me shirtless or her in a sports bra. Photos of us getting spruced up to go out with friends, her in tight shorts and me in college douche-bro regalia. Pictures after showers, wet and wearing only towels. Things that two best friends would probably never send each other unless, of course, they were developing a mutual sexual attraction.

But still the sexual tension wasn’t commented on directly by either of us. There’s no way it could possibly be explained away by ignorance at this point, it just felt like if we talked about it then things would have to change and I know, at least for my part, I didn’t want to risk losing my best friend like I almost did already.

And so we low-key flirted for several months until my first year of college was finally over and I would be traveling home for summer. I’d been home over winter break, but had a lot of family to be visiting and Jamie was always busy, so we hadn’t had a chance to meet up.

To tell the truth, I was nervous to see her again. I didn’t know what our digital flirting would translate to face to face. I was torn between wanting everything to just be normal between us, or possibly wanting to actually pursue something more. Even as I considered it the thought seemed crazy to me; was I really romantically interested in Jamie? How absurd! And yet, why not? We’d been best friends forever, that had to mean something. And now as she transitioned there was no denying that she was beautiful and I was absolutely attracted to her in a sexual way.

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