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Time travelling to the future only to realise the world has ended and everyone (including your family) is dead is honestly not that great, but you’d be amazed by how resilient humans are and just how much they can get used to.
After a couple of days wandering around the ruined city, trying to find anything, literally anything that might help him; Five decides there's nothing here and he has to check out all the other major cities around the US. So, he packs a small cart full of all the necessities he’d need on his journey (and the torso of a mannequin) on his journey.
After a couple weeks Five begins to talk to the mannequin, he’s not proud of it but it's more that he needs to say his thoughts out loud so he can work through them better. Well, at first anyway. After a while, he begins to have more and more mundane and normal pretend conversations with the mannequin. Just small things like wondering out loud what he should have for dinner and imagining the mannequin saying, chocolate bar, back to him. Of course, as time goes on Five really just wants a friend, needs a friend, and the mannequin is the only one consistent human-shaped thing in his life so that’s what she becomes, his friend.
Grace had once said that if they had another female sibling she would have named her Dolores and so in honour of the only mother he had ever known, he named the mannequin Dolores.
Since Five was quite young he had always known there was something different about him then the rest of his male siblings. In a weird way, he’d always felt most similar and comfortable around Vanya, which made no sense to him since she was the ordinary one of his siblings and surely he should be relating to his superpowered siblings more, right? But seemingly, no, and it wasn’t that he just felt comfortable around her, he also sometimes got his ugly, dark, jealous feeling in the pit of his stomach around her. He didn’t understand it at all. He’d watch her long, brown hair swish around back as she ran down the stairs or her skirt ruffle in the wind and he feels jealous.
It wasn’t until he got to voice these feelings to Dolores that he realise that he wasn’t really a he.
Five and Dolores had made their way to Washington D.C. that they came across the wreckage of a department store, one quite like the one Dolores was from. But unlike the one Five had found her in the clothes in this store has been preserved much better. However it wasn’t all the clothes, it seemed to be only the clothes from the women's section.
For some reason though this fact that Five only had the women’s clothes to choose from made them happy, positively giddy in fact. The Umbrella Academy they had left in was in tatters and it was getting much too hot to wear in the blazing summer heat.
First Five found a new outfit for Dolores to wear, a loose, pink, shirt dress and sunglasses for her. And then for themselves, they found a long, white summer dress with a floral pattern, a big sun hat and brown, strappy sandals.
Fuck social norms, Five thought, it was the apocalypse and if you couldn’t wear whatever the hell you wanted in the apocalypse then when the hell else could you?
“Do you like it?” Five did a twirl and asked Dolores after changing into their new outfit.
“Really? Thank you so much, you look great too you know.” They told the mannequin, beaming at her.
As amazing as it felt to wear a dress for the first time it was also terrifying. Five had felt more like themselves putting on a piece of clothing then they had in their whole life, and that was scary. Five knew what that mean, back when they had been at the Academy they always had their nose buried in a book whenever they weren’t training. The library at the Academy was extensive and had books on pretty much anything you could ever want to learn about and of course, there had been a few books on LGBT+ people. At the time when Five had read those books, they tried to ignore the twisting feeling they got in their gut as they read about transgender people but now realised they couldn’t ignore it anymore.
Turning to Dolores, Five said with a waver in her voice, “Hey, do you think you could call me she from now on?”
The years went by and things got easier, well puberty kinda sucked but once she got through that from then on it was easier. She still had a lot of dysphoria but part of her was thankful for the fact that she was all alone (apart from Dolores of course), there was no one there to judge her and she could effectively do whatever she liked now.
And then The Handler comes along and fucks it all up.
Working for The Commission wasn’t that bad at first, in fact, it was pretty great and Five found out she was pretty amazing at killing people. The Commission also didn’t care about her being trans, they even got her HRT (and trust her, second puberty was very strange) and offered her any and all kinds of surgeries she could have wanted.
All of this was great but really all she wanted to do, all she had ever wanted to do since that fateful day she jumped forward in time was save her world from the apocalypse.
So she goes back.
She bursts through the time portal she made and fits the soft grass of The Academy garden and she feels… smaller? She looks down at herself and she’s not the fifty-eight-year-old women she's used to being, she’s back in her thirteen-year-old body. Unchanged and unmistakably male. Fuck.
She’s taken out of her thoughts as she hears someone say, “Why is he wearing a skirt?”
She looks up and realises the adult- very much alive versions of her siblings, sans Ben, are all standing in a semi-circle around her, staring at her.
“She,” Five corrects as she stands and brushes herself down, “Why is she wearing a skirt, is what you should have said.”
The rest of her siblings all give her the most confused looks, other than Klaus who grins. Ah, of course, he’s the only one who understands.
Five sighs, “I’m trans, I’m a woman and no you don’t get to ask any more questions about it.” Of course, her siblings only proceed to ask a million questions about it, completely ignoring her request.
God, she forgot how annoying they all are.