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Should I take a Leap?

Summary:

Some days, the feeling of his trousers makes his skin crawl in a way he’d always try to ignore. Whenever someone refers to him as anything slightly masculine, he wishes he could hide in Charles’ backpack forever. The way his hair frustrates him to the point where he wants to rip it out; it just feels so undeniably masculine. On those days, Edwin couldn't stand being in his own skin.

During those days, before Hell, Edwin had gone to his older sister’s room and Florence would look at him with a knowing smile. She’d gather the dress and the undergarments that they’d learned suited him best and she’d let him change into those. Edwin would spend most of the day in the dress, feeling more comfortable and content than if he hadn’t worn the dress. Edwin still couldn’t recall the entire days, but he knew the moments. Little things he held dear to his heart.

Notes:

Genderfluid Edwin has been on my minddddd. I could not escape it so here.

This fic is in the same universe as my other fic Where Have you Buried all Your Children but you don't need to read that one to understand this one!

Hope you enjoy!

(See the end of the work for more notes.)

Work Text:

It was on a case when Edwin started to think about it. 

 

Edwin had just been sparing a glance to the world around him. A flash of colour alerting him. 

 

The pale blue had caught his eye in a way many things didn't. He was used to skimming over countless items that were irrelevant to the case. His focus was usually set towards the details that mattered, yet every so often, something would break through the noise- the mundane- and command his attention. 

 

In the shop window was a dress. 

 

He knew that dress.

 

It was a pale blue, delicately adorned with lace that danced on the edges of cuffs. Edwin got lost looking at the fabric, recalling how it had been paired with crisp white leather gloves and dainty, pearly shoes- footwear favoured by the women of his era. The very sight of it triggered a flood of memories, the sound of his older sister’s laughter and the cheering of his little siblings. 

 

He remembered the perfect harmony with which each accessory was chosen, a symphony of colour and style, performed by his sister. Each detail had mattered- the parasol that matched the gloves and shoes. He could almost hear the soft rustle of the fabric as it fanned out when Edwin would twirl. The feel of the lace was soft and smooth, becoming more and more comfortable each time it was worn. He thought of how the collar stood up, rigid and in perfect place. 



Edwin knew that beneath the dress was a white chemise, and he knew the weird feeling of the ‘s’-shaped corset that moulded the desired silhouette. Every element of what went into the dress was there in his mind. It reminded him of chasing Daphne, always catching the young girl before being able to brush her hair. Of spinning in front of Florence’s mirror while she twisted to look at every angel of his clothes on her. 

 

Edwin knew that dress well, to him it was a tapestry woven with memories of a time he could barely recall. He'd worn that dress before. Many times, to have the feel of it and the undergarments ingrained into his mind. 

 

Edwin had lost so many memories of his life to Hell. Erased like words on a chalkboard. 

 

This dress, this particular memory, seemed to come back to him, vivid and bright. He gazed down and took in the sight of the pale blue dress. It felt like a piece of his past plucked straight from his being. Ghosts were made from memory, this was one he cherished. 

 

He twisted his hips playfully, feeling the skirt swirl around him, embracing the old feeling. He couldn't help but grin, child-like and carefree. Pure joy that stemmed from very few moments in his childhood that had been buried under the weight of Hell.

 

 For now, he was back in Florence’s bedroom, holding Jacobs hands and teaching him how to dance, while Daphne yelled scores from the sidelines. Right now, he was running through their part of the manor, skirt billowing behind him, slipping on corners as he was chased in a game of ‘It’. 

 

But that dreamlike state could not last. It was shattered when he heard the sounds of birds chirping in the background. Then the rumble of a car passing on the road, its noise harsh and jarring. 

 

And just like that, the fairytale was over. 

 

He found himself back in his school clothes, his trousers now suffocating. The pale blue dress, with its memories of innocence and joy, had vanished without a trace. All that remained was the mannequin, a stark reminder of what once was. It stood there, holding the dress, mocking and taunting him with a past he could never quite have. 

 

“Edwin?” 

 

Charles had called and Edwin had turned back to the present, heading towards the case with his past left behind him. 



It wasn’t until later when he started to really think about it. 

 

Some days, the feeling of his trousers makes his skin crawl in a way he’d always try to ignore. Whenever someone refers to him as anything slightly masculine, he wishes he could hide in Charles’ backpack forever. The way his hair frustrates him to the point where he wants to rip it out; it just feels so undeniably masculine. On those days, Edwin couldn't stand being in his own skin. 

 

During those days, before Hell, Edwin had gone to his older sister’s room and Florence would look at him with a knowing smile. She’d gather the dress and the undergarments that they’d learned suited him best and she’d let him change into those. Edwin would spend most of the day in the dress, feeling more comfortable and content than if he hadn’t worn the dress. Edwin still couldn’t recall the entire days, but he knew the moments. Little things he held dear to his heart. 

 

There were also the other days, where he felt too masculine but when wearing the dress it felt like too much. It was stressful those days, though few and not often. But they drove him insane much like the way his clothes feel to him currently. 

 

He longed for Niko’s presence. This was not the first time, and it wouldn’t be the last, that he found himself wishing she were still around. Niko understood things in a way Edwin couldn't express. Niko held an insight on these things that Edwin never had words for, and for the few things he didn't, they weren't very pleasant words. 

 

Referring to himself as well ‘himself’ even caused an ache in his chest that always seemed to vanish before he could study and figure out the feelings eating away at it. What was this? Why has wearing that dress brought all of this up? 

 

Edwin’s mind turned to when Niko first reacted to his disguise. The question of ‘Are you always a woman?’ spinning around in his head while his answer of ‘Yes’ trailed after it. He and Charles never really discussed him being a woman as his disguise, they'd just figured it would be easier to pose as a married couple and a hetrosexual white couple was so common it was easy to be looked over. 

 

He thought of his days wearing the pale blue dress and the comfort he’d find when he got to be seen as a woman. 

 

It was just nice . It was nice to be seen as a woman on those days, to have people refer to Edwin as Miss and not Mr. It was just nice. It didn't create this sickening feeling in his stomach he’d been blocking out for over a century. The memories of Charles referring to Edwin with ‘she’ and ‘her’ made something like happiness well up inside of him. 

 

Was that allowed? Was Edwin allowed to sometimes be a woman? Be a girl on the days it felt right to be and be a boy on the days that was right. Was that okay? 

 

Edwin didn't know. 



Edwin waited for Charles and Crystal to go out, they’d been planning on going to a concert in London. After Charles gave his goodbye, a kiss on the cheek, forehead and lips, Edwin stood from the chair and focused on what he was wearing. 

 

He thought of the dress, the fabric, the weight and the colour. Let the memories of it flow back into him like a river. Allowed it to shape his appearance and smiled at the sight of the skirt swishing at his ankles. 

 

He then thought of Daphne’s hair, the length, the weight and the feel. How it would feel attached to his own head and then it was there, brushing against his cheeks. 

 

Edwin just wished she had a mirror. She instead focused on pulling her hair back, keeping part of it down while using a blue ribbon to secure the rest of it up and out of her face. 

 

Once she was done she did a twirl. Then sat down at her desk and opened the book she’d been wanting to re-read. She felt good in her skin and she wanted to sit in that peace and contentment for a bit longer before thinking too much. 




It was even later when Edwin started thinking about how Charles would react. 

 

She’d been sitting peacefully, happy in her skin and the itchiness that had followed when she wore her regular trousers replaced with the gentle feeling of her skirt draping over her legs. She’d let her mind wander to Charles. 

 

Charles, the light of her life, Edwin’s wonderfully kind boyfriend. She didn't think about how he might react until now. Thinking of how he could walk in and see her dressed like this. 

 

Would he accept it? Allow her to exist as she does just sometimes as his girlfriend? (and god doesn't that word feel good?) Would he think she is sick in the head? Would he want to break up with her now that she was different? Would he be disgusted? 

What happened if he couldn’t love her now she was like this? 



Wait a tick. 



This was Charles . Charles, who looked at Edwin as if she was the sole reason every star shined in the sky. Charles, who looked at Edwin with deep love, trust and genuine care. This was Charles, her Charles , who went to literal Hell for Edwin. It was Charles who’d encouraged Edwin to be herself, with all her different mannerisms. It was Charles who grinned at practically anything interesting Edwin did. It was Charles, who was very much bisexual and would still be attracted to Edwin when she presented as feminine.  

 

It was Charles Rowland she was thinking about and there was no need to worry about how he would see this. Charles loved her, more than anything in the world. 

 

Still, as it got close to 3 am Edwin made her appearance go to her regular one, trying to ignore how it felt like being tied up and locked in a cage. 



It wasn’t until a week later that Edwin actually talked to Charles. 

 

They’d been curled up together, bare under the blanket on their new sofa. Charles was flat on his back while Edwin rested on his chest, drawing patterns into his skin while Charles trailed a hand up and down Edwin’s back. They shared soft, lazy kisses as they lay in complete peace. Enjoying each other's presence and the feel of skin on skin contact they'd both ached for. 

 

“I have something I wish to discuss with you.” Edwin finally gathered enough confidence to say. 

 

“Yeah, love?” Charles replied, pressing a soft kiss to the top of his head, the action making Edwin smile. 

 

“I’ve come to a realisation of sorts about myself,” He explained softly. He felt comfortable in his own skin today, happy with his short hair and somewhat confident in his body. “I-I- well- Do you remember-” Edwin cut himself off with a groan of frustration. 

 

“Hey, love, breathe for a tick.” Charles ordered softly, a hand coming to hold Edwin’s. “You know you can tell me anything, Love, anything at all.” 

 

“I know, it's just difficult to admit out loud. I know perfectly well you won’t ever judge me but it has some tethers to my… life,” 

 

“You’re life?” Charles asked, knowing Edwin hardly remembers much from it, and talked even less about what he did. 

 

“Happy memories of my life are difficult to come by. This new… thing is rooted in some of my happiest memories.” Edwin squeezed Charles’ hand tightly, trying to not worry. 

 

“Okay.” 

 

“I-Well, you know how my disguise is a woman?” Edwin started. 

 

“Considering I make them, I do indeed.” Charles teased to try and diffuse some of the tension. 

 

“Hush. When I was alive, sometimes I’d go to Florence’s room and I’d put on a dress she ended up setting aside for me. On those days I’d feel happy and free. It was nice. I saw the dress again, in some vintage shop, not the exact one I’d worn but made by the same tailor. I realised that those days I couldn’t stand being masculine, that I preferred wearing my disguise at certain times and being perceived as a woman.” 

 

“Okay,” Charles gave a squeeze to his hand as a reassurance. 

 

“I believe that sometimes I prefer to be seen and present as- as a woman while other times I prefer to be seen as a man, if that makes sense?” 

 

“So sometimes I have a boyfriend and other times you’re my girlfriend, yeah?” Charles dragged out ‘girlfriend’ as he spoke as if he was unsure of it. 

 

“Yes, exactly.” Edwin confirmed. 

 

“Hey, look at me for a tick, Love?” Charles requested. Edwin turned and moved to be more sitting up to stare into Charles' loving brown eyes. 

 

Charles' hand came up to cup Edwin’s check and he couldn’t help but lean into the pressure, feeling completely secure and loved just from a simple but genuine gesture. 

 

“I love you, no matter what you present or show yourself as. I don’t care as long as I’ve got you , okay?” Charles waited for Edwin’s nod of confirmation before continuing. “Now, what are you right now?” 

 

“Male, everything fits right now.” Edwin said softly. 

 

“Good. So when you are a girl, you want to be like ‘she’ and ‘miss’ and all that?” Charles asked. 

 

“If you wouldn’t mind.” Edwin replied nervously, slightly tucking himself away from Charles. 

 

“Hey, Hey, don’t shy away from me, Edwin, I’ve got you. I love you. I might ask some questions, most of them will definitely be stupid but I wanna make sure I get this right, don’t I?” Charles smiled brightly in a way that just made Edwin feel so seen and loved. 

 

“I love you too.” Edwin mumbled, pressing a kiss to the palm of Charles’ hand. 

 

“Good.” Charles brought Edwin’s face closer until their lips were pressing together in a soft kiss and Edwin slowly allowed himself to move back into laying down at Charles’ side, feeling completely and utterly loved and cherished. 

 

Right now he was happy, safe in Charles’ arms. 



Telling Crystal had been much easier. 

 

With Charles’ encouragement and love behind him, Edwin was confident he could do anything. He was sure Crystal would make some sort of comment but wouldn't mention it after. She was modern so Edwin hoped she wouldn't have anything bad to say about it. 

 

“I wanted to tell you something.” Edwin started carefully. It was just them in the office, Charles being on a supply run. 

 

Crystal was currently spread over the sofa, with one leg swung over the back and focused on her phone. 

 

“Okay.” She replied slowly. Moving to sit up and face Edwin nervously. 

 

“I recently came to a realisation about myself that I wanted to tell you to make you aware.” Edwin explained 

 

“Okay, go ahead.” 

 

“I have figured out that sometimes, some days I prefer to be seen as a woman rather than a man and I would like you to refer to me as such.” He rushed out, looking anywhere but Crystal's face. 

 

As much as he hated to admit it. He cared about Crystal's opinion. He cared about what she had to say about him and how she viewed him. She had managed to worm herself into the small circle of people Edwin cared about. The similarity she shared with his little sister, Daphne, also helped. 

 

The idea of Crystal, someone he was starting to value as much as his own siblings, of not accepting him or thinking he was a freak or wrong was horrifying. Even with the knowledge that Charles would set her right. 

 

“So you're genderfluid?” Crystal broke him out of his spiral and he looked at her with a mixture of shock and confusion. 

 

“What?” He asked. He had no idea what that word meant. 

 

“Fuck, right you wouldn't know that. It basically means what you told me. Genderfluid, that sometimes you want to be seen as a girl and other times a boy,” she shrugged. “It's a thing nowadays.” 

 

“I-I did not know there was a name for it.” Edwin confessed.  

 

“Yeah, it's okay to be like that, Edwin.” Crystal replied rather awkwardly. 

 

“Thank you, Crystal.” He said quietly. 




She was planning on presenting as a woman today but they had clients coming in today so she couldn't possibly wear the regular dress she'd choose. That dress was for day trips, made for the spring and summer not made for walking around London. 

 

So here she was, trying desperately to think of an outfit to wear. 

 

She knew she wanted it to be blue, a blue similar in colour to her regular sweater vest. She also knew she needed to be aware of her lack of pockets now and would need something to hold her notebook and pen. 



She was going through memories while waiting for Crystal to arrive when she landed on a dress she's pretty sure belonged to Daphne. 

 

She remembered the lace collar, the way the sleeves fit over her arms. The way the second shirt piece fitted and puffed out. The way the skirt would fall. She also thought about Mrs Cunningham, the housekeeper who'd worn a chatelaine clipped to her skirt, with all her necessary items attached and ready to be used. 



She breathed and focused on the memory, pulling the pieces and weaving them together to create an outfit suitable for her, something respectable but also comfortable. She already had placed the correct undergarments on so her shape would from correctly to fit the clothes she wanted. 

 

She breathed and it was done. She looked down and saw the blue skirt and the blouse she was wearing. Comfortable and good. She looked down at her chatelaine and went through each item she'd put together, a pen knife, a small bookcase, a pair of scissors, her regular Notebook with its unlimited pages as well as a letter opener and a little lantern charm. 

 

She smiled. 

 

She walked out of the spare room, turned into a bedroom for Charles and Edwin, and saw Charles and Crystal waiting patiently and talking about things. 

 

“Would one of you be able to help me with this?” Edwin asked, holding up the blue ribbon. 

 

Crystal and Charles turned to her both with near matching faces of shock. Edwin watched with a pleased smile as Charles' cheeks began to flush red while his mouth hung open. 

 

“You look good,” Crystal commented, slightly astonished. “Where have you been hiding that waist,” That comment muttered slightly. 

 

While Charles seemed stuck in his stupor, mouth still hung open that Edwin wouldn't be shocked if he started drooling at this point. Crystal walked over and took the ribbon from Edwin's hands and gestured to her to go sit down at the chair. 

 

“How do you want it?” She asked. 

 

“Just part of it away from my face, similar to yours if you could,” Edwin requested. 

 

“Got it.” 

 

Edwin couldn't really feel Crystal's hands moving through her hair and tying it up gently but the fact that Crystal was doing this for her felt like acceptance more than any words could. Crystal moved to the front of her face and gently and carefully pulled a few hairs to frame her face delicately. Before smiling kindly and moving away. 

 

“I think Charles is about to fall through the floor.” She muttered to him with a huff of laughter. 

 

Edwin looked over to see Charles, still gawking at her appearance. She walked over, noting that she was a decent bit taller because of the heels she now wore, and gently closed his mouth. 

 

“You-you look great- just well fit- I mean you're beautiful!” Charles stuttered and stumbled his way through words, clearly flustered. 

 

Edwin smiled, amused. “Thank you, Darling.” And pressed a soft kiss to Charles’ check. 

 

Distantly she could hear Crystal's poor attempts at muffling her laughter at Charles’ reaction. 




(“Crystal, I’m so bi. I think she might kill me.” 

 

“You looked like a goldfish for a solid 5 minutes. I'm surprised I didn't kill you.” 

 

“Crystal, she is so fit. I told her that to her face! Why would I tell her that?” 

 

“It was funny though.” 

 

“Not helping!” 

 

“Listen, I think you just have a thing for strong independent women and Edwin in general.” 

 

“Crystal, I want Edwin to crush me.”

 

“Ew.”) 




“Crystal, I need your help!” 



It wasn't normal for Edwin to barge into Crystal's flat. Typically one to wait for her at the Agency rather than go to her. But Edwin was panicking and she didn't know what to do

 

“Jesus fucking Christ!” Crystal nearly jumped out of her own skin, the remote in her hand going flying across the room and landing with a loud thud. 

 

The noise made both Crystal and Edwin wince and Crystal fixed a glare onto her in response. 

 

“My apologies.” She stiffly said before moving on. “Charles wants to take me out on a date but I simply do not know what to wear!” 

 

“And you're coming to me?” Crystal asked. 

 

“You're the only other person I know aside from Charles! And Charles thinks I look incredible in everything.” She explained. 

 

“Wonderful. Okay so where are you going?” Crystal asked, looking slightly interested at the chance of getting to dress Edwin up like a personal Barbie doll. 

 

“I'm not sure. He said to wear something ‘fancy’” Edwin nervously tapped her fingers on the back of her other hand. 

 

“Okay I can do that. Come sit, we are going to make this boy bi panic so hard he falls through the floor and into your bed because I don't want to hear any more poetry about your eyes.” Crystal pulled her laptop from somewhere as Edwin went to sit down next to her. 

 

“So how much skin do you think you can show?” 




Crystal had let Charles know to come collect Edwin for their date at her place so here Charles was. 



Charles was expecting to get blown away by whatever Edwin wore, he thinks Edwin looks mint in anything. Especially that green waist coat he'd worn for their date to a panto last month. 

 

Charles held some flowers, forget-me-nots, roses and hyacinths. Ready to be faced with a beautiful date. 

 

Nothing could have prepared him for what he saw. 

 

Edwin's back was to the mirror, her very very pale and bare back. Green silk hung against her skin, wrapped around her neck and draping down. There was a Cape-like part of the green silk thrown over her  shoulder. Her shoulders were bare and there were matching green gloves slid up her arms all the way to her biceps. 

 

The dress was clung a bit to Edwin’s body, hugging her figure a bit and making her just look incredible. 

 

It was modern, very modern. Not something Charles expected at all. The forest green colour stood out against Edwin's pale skin, making the expense of her pale, naked back even more tantalisingly and Charles wanted nothing more than to run his hands down it and feel her shiver. 

 

Her hair was up, kept neat and tidy in a plait going across the top of her head like a crown with little pearls spotted on top. 

 

She'd looked at Charles, head turning so he could see her side profile and Charles was gone

 

Distantly, he mourned the fact that Edwin was no longer in his line of sight and that he was now in fact a few floors down in Crystal's apartment complex. 

 

He very much needed to see more of Edwin so he scrambled to get up and dashed out the wall until he made it back to Crystal's floor and then her flat, running straight through the wall and breathing heavily. 



Crystal was bent over, hands on her knees and cackling like a bloody witch, the absolute traitor. While Edwin was standing there looking pretty, staring at the spot Charles had been. 

 

Charles rushed through to them, chest heaving with breathes he didn't need but god if he didn't he's sure he might suffocate because how does she look so good

 

“You look bloody brilliant. Like God please step on me- I mean you're stunning, mate, I mean Love!” Charles sputtered. 

 

“Thank you, dearest, you look quite lovely, yourself.” Edwin had a teasing smile on her face. 

 

Charles walked forward, taking Edwin's hand and staring her dead in the eyes as he placed a gentle kiss on her knuckles.

 

“Absolutely stunning, Love,” 

 

Charles ignored Crystal's wheezing breaths and went over to pick up the flowers that had not been able to follow him through the floor and passed them over to Edwin. 

 

She took them with a smile. “Thank you, Charles.” Then pressing a kiss to Charles cheek. 

 

“Alright, we'll be off. You can stop your giggling now,” Charles spoke to Crystal now. 

 

“Now you finally notice me!” She snorted. “Okay have fun, don't be late, try to not make out in public.” 

 

They both thanked Crystal with an eye roll from Edwin and were off. 

 

 And if Charles kept his hand on the small of Edwin's back for the entire night, no one was there but Edwin to notice it. 



Charles loved Edwin in any shape or from. Whether he was dressed in that very handsome emerald waistcoat or if she was dressed in a stunning forest green dress. Edwin was so incredibly happy and content that he’d be able to feel comfortable in his own skin without fear of rejection. He wished Niko could see him now, he’d grown so much and simply wished she was here to see his progress.  

 

But there was no more itchiness or ache in his chest. 




And maybe somewhere in England a young girl unearthed a box from over a century ago with a journal and a lovely, perfectly preserved blue dress. 

Notes:

I was listening to green green dress when writing the date part so I was very much influenced.

Also feel free to check out my tumblr , @thepearlyalbatross, as I have art of Genderfluid Edwin on there currentlyy

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