#Jack Delroy selfship
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selfindulgentfandomstuff · 1 month ago
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“I feel kinda ridiculous..”
“Nonsense, doll, you look lovely!”
“Really?”
“Really. You’re so pretty I could look at you forever..”
“… you’re tipsy.”
“Eh, maybe. Still pretty~”
———
Blatantly obvious self insert wish fulfillment of me wanting to wear feminine clothing sometimes but feeling too ugly to do so without being mocked 😭
———
Esther ‘Essie’ Watkins (left): they/she
Jack D/elroy (right): he/him
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Proship + adjacent DNI
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Chocolate Whiskey and a Borrowed Bed - Leo Fiske/Jack Delroy
Warnings: Era-influenced homophobia, publicly closeted Leo, entirely closeted Jack, mutual pining, Leo really gets around, blowjobs, handjobs, anal sex, hopes for the future ;w;
Wordcount: 10074
Summary: It's been one year exactly since Night Owls was brought back from the dead, so Leo throws the crew and their friends a big party at his unlisted address so they can all celebrate properly away from prying eyes after the near disaster last year almost was, and maybe, a little party is all Jack needs to finally get some things off his chest.
Notes: I wrote this for my wonderful talented amazing friend @glamgoths for her birthday, love youuuu 🥰💗💗💗 she's a Jack/Leo truther to the point where it made me a Jack/Leo truther, Leo became so cool in my eyes that I not only have fun writing him in readers but it also overwrote my selfship jealousy in order to ship him with Jack, so I surprised her with this hehe
Halloween, 1978.
No one could explain what had happened last year no matter how they looked at it, their carefully planned show to get great ratings just in time for the start of Sweeps Week nearly ruined by a series of bad luck. Even he couldn’t figure it out, not with undeniable certainty, but it’d led to Christou getting some kind of food poisoning after his unknowingly staged communication with someone in their audience, then some carefully planned messages from some poor woman's son, and finally ending with him throwing up all over Haig after having to deal with his usual bullshit. 
It was funny if not shocking, but it had done the ratings good, something from his pre-show meal turning the contents in his stomach black, squid ink he'd said, which sounded disgusting when Leo had heard it, but damn if it hadn't worked in their favour.
Haig had kept his check in the end, and he'd flashed it in June's face when he'd been able to recreate the same kind of hypnosis as her, hell, it’d even gotten him a little backstage, but he’d never admit it. She'd stormed out when Jack tried to replay the footage of Lilly’s possession to then prove that she hadn’t faked anything, that'd been the last straw even with Lilly wanting to show Haig once and for all that he was wrong, and the show had ended with Cleo singing to a disappointed audience. But the ratings, the fight for that last scene that never came, they'd impressed Cavendish’s new vice president of marketing just like they’d wanted, and it'd brought the show back to life.
It was a year later, Halloween again, and this time Jack was determined to have Haig eat his words. He'd searched high and low for even better guests, found another illusionist like Haig had been but better, and the moment she’d walked out on stage it was clear that there was an air to her that Christou hadn’t held. She'd claimed to levitate as well as commune with the dead and read futures, and he'd almost paid - his presence was practically required after last year, to Jack's chagrin - but decidedly hadn't when she refused to tell him how it was done. The audience had been split, one half telling him to pay her while the other wanted to know how she did it when he did the same and he was perfectly fine with explaining it, and she'd ended up being consoled by Jack when she became overwhelmed on camera.
Leo didn't like that part of the show, just another June to replace Madeleine, and he'd downed a bit too much whiskey as the show continued on after the break. She didn't stay no matter how much Jack pleaded for her to, her bit was done in her eyes and Haig wouldn't let up even when the cameras were off, so Leo had to be the one to help her gather her stuff and make sure she reached her ride. He did it as calmly as possible even though the memory of Jack's arms around her made him light up a smoke while they waited by the busy street, despite her request that no one smoke around her; it was petty, but she'd live, a little smoke wouldn't kill her when it was very clear she'd only come on the show because she wanted to be near Jack, not because she believed in his mindset about the occult despite her career choice.
The show was wrapping up now, it felt like it'd lasted several hours this time instead of just one, and Leo had Jack's favourite ready for him with a spin, picked especially for tonight; it was a glass of Ballotin's new brand of chocolate whiskey, to keep in the spirit of Halloween and candy while also being perfect for a man surely stressed beyond belief because he needed to top last year, and as soon as the cameras cut and he handed over the glass, Jack downed it all before he even had a chance to open his mouth to congratulate him on how it’d went. It took him a moment to register the chocolate amidst the usual burn of the whiskey, his eyes going wide in surprise as Leo just smirked.
‘Thought you could use a taste of the party before we get there,’ he told him before blowing a light lungful of smoke towards the ceiling, Jack swirling the last drops around before taking a sniff.
‘So is this considered a trick, or a treat?’ he asked him, already starting to calm again now that it was over, and Leo liked the sight of that as he led him backstage to gather his own things as the crew cleaned up for the night. 
‘Depends on how much of a surprise it was,’ he figured as they reached the snack table, or what was left of it, it'd been picked clean between the crew and Jack sneaking the chocolatey treats to the Madame all night before her departure. Jack thought about it before considering it a treat apparently as he poured himself another glass, drank it back, and then left it to be cleaned up later. ‘You doing alright after Haig drove away your girlfriend again this year?’
‘You know I'm not seeing anyone, and I'm more concerned with how it all turned out, how were the phones this year?’
‘Ringing off the hook once she started floating and no one could find the strings, not even Haig,’ Leo told him, the two making their way out of their set room and into the hallway leading to the elevators. ‘Rang so much we had to borrow some phones, lots of questions about how we did it and if she'll be back with more, since she isn't performing live for a while.’
Jack did a little leap for joy as the elevator doors opened, his eyes wild with excitement over the news, he always got so youthful despite nearing his 50s the moment he learned that a show had done well; he was getting better with accepting he would never beat Carson, he'd been against the therapy at first, but seeing how much his fans and co-workers still cared for him had encouraged him to despite the stigma, and while he was still getting over Madeleine, at least he was okay with putting on a good show without also putting his entire self-worth on the line.
That was good, Leo liked to see him happy and wanting to be ready to knock ‘em dead again, he could worry about the numbers and the sponsors enough for the both of them from now on.
‘How late you gunna stay out tonight?’ he asked when they reached the ground floor, Jack thinking about it and pulling on his thick coat over top of his suit while they headed for the door leading to the staff parking lot.
‘Not long, trying to get better sleep, Bianca says that it'll help me focus better if I cut down on the late nights, try sleeping when the sun is down instead of working til it rises,’ he told him as they reached their cars, Leo holding his cigarette between cold fingers as he rested on the roof of his car.
‘Another woman in your life?’ he teased, but there was a bitterness in there, his eyes hidden by the dark as well as his sunglasses as Jack leaned against his own car.
‘Far from it, she's my therapist and she's married, for one,’ he chuckled almost nervously, Leo raising an eyebrow.
‘Hey, I won't tell her husband if you don't,’ he joked just to see if Jack liked her, the other man running what was definitely a nervous hand through his hair at that one.
‘For two, she isn't married to a man,’ he continued in a quieter voice than before, silence falling between them as Leo caught on instantly; they didn't talk about this sort of thing even though more of them were appearing in public. He was one of them, not that he'd ever tell, but she must trust Jack in order to tell him that, and the thought of why she'd trust him made him nearly crush his cigarette before he snuffed it out on the back of his hand really quick before tossing it away.
‘Ah, well, that'll put a stop to things,’ he agreed, Jack laughing again a little more easily now that he knew Leo wouldn't judge this random woman he knew. There was a flash of something in his eye, even from afar and in the dim lights he could see it from there, and he gave the car a tap to get Jack's attention when he started to unlock his door. ‘Hey, why don't I give you a ride to my place, save a bit on gas?’
‘You gunna drive me home later? I already told you I can't stay long this time,’ he reminded him, but he was already walking over, and Leo waved away his concern for his sleep schedule.
‘You know I've got plenty of room, just steal a bed when you've had enough, at least stay up to bob for some apples and watch a movie with us, I spent a lotta time setting all this shit up,’ Leo insisted, and Jack laughed even easier as he reached for the handle.
‘You mean you got your assistant to set it up?’
‘Fuck no, she only knows about the penthouse, not the house.’ They piled into his car and he turned on the heat as soon as the engine turned over for Jack's sake, and he had to admit it was a nice sight to have him sitting there in the passenger seat as he fiddled with its position and got warmed up. He didn't smoke anymore, he'd quit for good after last year, and Leo made sure not to light up on the way to the house; naturally there was a group of them gathered around his front door when they arrived, he'd banned it inside to avoid Jack giving in to any cravings and forcing him to restart again, and made a mental note to tell them to go out back next time. He shooed them aside as they approached even though Jack didn't need him to, everyone was already inside since those who knew about the place knew where the spare key was hidden, and they'd started everything while the show was finishing up.
He found out who'd gotten there first and went to thank them as Jack went through the motions of another successful show to those who didn't see him as often, the two separating as the party took them elsewhere for a while; he'd made sure to leave a note for the ones who arrived early, since it'd be a choice on their end seeing as they all knew that filming didn't finish til 1AM, and the living room and kitchen were filled with adult versions of the classic activities the kids around the city were surely also doing. There was a cheap tub filled with water and apples as promised, but there were also a bunch of hidden items in boxes the guests could touch and then guess at what was inside. There was a pin the skull on the skeleton taped to the wall as well as the tail on the werewolf for those who were feeling a little more childish on this fun night, and of course, the kitchen was filled with snacks and candy galore. 
He'd secretly spent a fortune on tonight because he knew this was Jack's favourite holiday, and because he needed to keep riding the high of good company and even better alcohol - he was still working on that - so he needed to make this as tempting as possible. On the outside he looked uninterested with it all, he was the adult here amidst this group of children, but on the inside he was glad everyone was enjoying themselves, small smiles escaping him when someone got too excited about placing the tail or skull correctly, by grabbing an apple on the first try. It took a while but Jack joined them after he met with what was probably every single person in the house - and even the ones outside - to continue marketing himself to them, making more connections, now that he was back, as he put it.
Leo let him mingle until he was done, and he had more Ballotin ready for him when he found him in the kitchen while he was going over the supplies for the remainder of the party. ‘No thanks, I've been trying to cut back, believe it or not.’
‘Jack Delroy, I can believe you when you say you've given up smoking, but drinking? What's gunna keep you running these late nights?’ Leo joked as he accepted the glass from himself instead, but this time Jack didn't laugh, in fact, the mood seemed to have dropped a bit. ‘You're serious?’
‘Yeah, Bianca helped me see I was relying too much on it after- after Minnie, so I've been cutting back, what you gave me earlier was the first drink I've had all week,’ he confessed in the emptiness of the kitchen while everyone else partied in the other rooms, and Leo felt a somberness he hadn't felt since he'd heard about Madeleine's diagnosis fall over him. Jack talked a lot about things, he had big dreams and never stopped at them no matter what tried to keep him down, it was the thing that drew Leo to him in the first place when he was looking for a producer to help get him into TV, and it was what made him fall in love, along with a long list of other things.
Yeah, he'd admit it sometimes, he'd fallen in love with Jack instead of just telling himself it was a crush that grown men shouldn't have on other men, but Jack was easy to love, always had been, even when Minnie had gotten there first and stolen his heart so completely that she never left, even after death.
He set the glass down on the counter and walked over to Jack where he was still picking through the assorted snacks for the specific ones he wanted, a small pile of chocolate-covered pretzels in his hand as Leo rounded the island and clapped a hand on his friend's shoulder. Jack stiffened, he'd probably meant to keep this one a secret since the smoking was shared by so many in the studio, and Leo squeezed to let him know that he'd respect that journey the same way he had the moment Jack had swore he'd quit for good when he'd been offered a smoke come November 1st last year.
Jack smiled and held Leo's hand over his shoulder, this was getting dangerous, but there was no one there to judge as Leo refused to pull away, just like he always did when Jack needed him to stand by his side. ‘You're a good friend, Leo, you've been there for me since the start, if you hadn't been with me when I lost her, I… I don't know what I would've done,’ Jack told him quietly, his energetic voice so soft the way it always was when he talked about Madeleine and almost quitting the business, and he knew he shouldn't, but he couldn't help but pull Jack into a tight hug. 
‘You're a good man, Jack, always been better than the rest of us, how could I let you crash and burn out there when there's still so much fire in you?’ he asked into his arm, because he couldn't face him, and he heard Jack let out a breath as he nuzzled into his neck in appreciation. He didn't get the shivers, his heart didn't skip a beat, his face didn't redden, but Leo felt like he could maybe admit he was in love twice in one night as Jack took all he could from the hug and finally pulled away. He looked a bit better, he must've been having a hard time restraining from everything when this time of the year was so hard to top, and instead of the whiskey, Leo grabbed two glasses and filled them with ice water instead.
This one Jack did accept, and they toasted over chocolate pretzels and candy corn while someone pinned something perfectly according to the yells from the next room. Jack drank it with a hiss through his teeth at the freeze instead of the burn, and he placed the glass on the counter and took his pretzels with a small shrug towards the stairs in the distance. ‘Gunna turn in for the night, you still got my room made up?’ he asked as he walked backwards towards it, and Leo tipped his glass towards him, of course he did, he always would. Jack nodded and helped himself to one of his pretzels before disappearing into the crowd, Leo watching him go before heading back out there himself, a smile plastered to his face as he greeted the night owls and other business casual friends, the late hours ticking away until they needed to either leave or crash on his couches. 
He made sure to clean up before retiring for the night as well, he'd hate himself come morning if he didn't no matter how much he wanted to put it on the ones currently taking up his couches, armchair, and even floor as well as the remaining rooms upstairs, and it was well into the AMs by the time everything in the kitchen at least was tidied so as to not disturb those already resting. He was dead tired as he scaled the stairs so he could finally get to his room, a symphony of snores coming from the spares lining the halls as they always did when he threw parties like this; it was the reason he bought the place, he'd always known people, even when he was young, thanks to his parents and who they in turn knew, so continuing that tradition and getting a place where he could gather everyone together and create this kind of environment for them in this unlisted home had always been second nature to him, always been who he knew he would be when he grew older.
He reached his room and turned the handle, everyone knowing to stay away because he did not lend this one to anyone if he was going to stay the night no matter who they were, and he was in the middle of taking off his sunglasses and rubbing his eyes when he noticed that the bed wasn't empty.
His eyes adjusted to the dark as he stared at the form under his blankets, someone had come in and snagged it while he was downstairs, and an annoyance like no other overtook him as he stormed over to kick them out, this room was off limits. He stopped when he saw it was Jack, his suit jacket ditched and the buttons on his shirt undone as he snored soundly away under the covers. The hair peeking over his undershirt made Leo stare even though he'd seen it before during emergency costume changes, or when Jack and Madeleine used to take over his pool. Now it felt like this was against some rule that'd never been spoken, this was intimate, a side of him he shouldn't be seeing, and he sighed before rubbing his eyes again and giving his friend a small shake.
‘C’mon, I wanna get some rest, go find your room,’ he told him softly, like he didn't want to wake him despite what he was both saying and doing, but when Jack understandably continued to sleep he steeled himself and pushed a little harder. ‘Jack, let's go, let me sleep.’
‘This is where I wanna be,’ Jack mumbled as he got even comfier, and Leo retracted his hand instantly as if he'd been burned.
‘This is my room, thought you asked about your usual?’ His voice just kept lowering even though he was actively fighting to speak loudly so as to keep Jack from falling back asleep, the latter glancing up at him through one barely opened eye before reaching for his hand and pulling it back to not his arm, but to his chest.
‘Let me stay…’ he whispered before his face softened again, he was just conscious enough to ask as he now actively tried not to fight off sleep so he wouldn’t have to leave, and Leo considered it before he frowned; he knew this couldn't be what he wanted, it was dangerous to be what he was and he couldn't have Jack following after him after working so hard to gain Cavendish's favour and sponsor and bringing Night Owls back from the dead.
‘Jack, stop this, get outta my bed,’ he demanded, his usual firmness back in place to protect himself, and this woke Jack up as he sat up with surprisingly clarity and stared him down.
‘I'm where I want to be,’ he repeated, and Leo's eyes trailed over his chest before he grabbed onto him, tried to pull him up.
‘You're too old to be playing games like this, you're a grown man for Christ's sake,’ he insisted as he tugged, Jack fighting him until he lost his balance; he fell forward, a knee shooting out to stop himself from crashing into the other man, and there was a moment where they stared at each other in the dark. He swallowed, this was too intimate, this was dangerous, if anyone heard and came to see what was wrong the both of them might lose everything even though nothing was even happening, he couldn’t do this to him, he’d nearly lost it all before.
He tried to shove him away, just let him have the bed, he’d find another room or join someone on the goddamn floor if he had to, but Jack was holding him so firmly, just like he did when he’d come to him about Madeleine’s sickness, and her passing. He was refusing to let go, and there was a sadness in his eyes underneath the desperation and fight to stay, there was something he was hiding from him just like he had about going sober. He tried to pull away again but Jack tightened his grip and used all his strength to attempt to bring Leo to his chest, and when that didn’t work he threw himself into his arms.
‘Jack, you don’t know what you’re doing,’ he warned, but his voice wasn't as harsh as before, and he felt Jack shake his head against his shoulder before turning to press his face into his neck. ‘Jack-’ He grabbed on but he couldn’t yank him off, he hadn’t drank much and that had been hours ago but he must be drunk, he knew the dangers too, there was no way this could happen no matter how the world was progressing, not for them.
‘Please, I’ll get you something to drink, you don’t even have to do anything with me, just let me pretend that it’s normal to feel this way, just for one night,’ Jack whispered into his skin, his unkempt hair disturbing Leo’s curls, and he froze and stopped trying to pull him away when he felt Jack tremble.
‘How long?’ he could only ask, and Jack didn’t pull away.
‘Since the Grove, being around the other men reminded me of what I’d forgotten.’
‘Fuck, no- how long have you wanted this from me?’ He paused when Jack didn’t answer. ‘Or am I just- the one you thought you could ask?’
It took him a while but he did answer, and Leo saw himself standing in the UBC lobby while Jack tried to make it past the receptionist all those years ago. All his big dreams to get into television instead of radio had made him turn on the charm with her, but when she couldn’t do anything because his low priority appointment had been canceled in favour of a high priority call and lunch date, he’d become desperate. Leo had watched as Jack had looked almost ready to give in and try again later, that fire in his eyes still there along with his frustration because he’d come so far, he had the experience and charisma, he just needed a chance.
Leo had been the one to give it to him, not because he’d fallen in love, because it’d taken a while for that to happen, but because he wanted to see what he could do.
‘Even before Minnie, I’ve… always wanted it from you,’ Jack confessed in the quiet of Leo’s bedroom like they were a couple of confused and experimenting teenagers again, just two kids who felt things that the world would never understand, come 30 years too late. Leo was definitely confused, he’d seen the way Jack loved Madeleine, that had been real, there were no lies or performances for the cameras between them, but for him to say this, to look like he truly meant it, maybe he knew less about the world than he thought. ‘Sorry, forget it, it’s the whiskey talking, I’m not actually a-’
‘You’re sober, you’ve been sober,’ Leo reminded him harshly, not wanting him to back out when it was reminding him too much of every single man he’d ever been with who told him the same the moment it was over, along with many utterings of it throughout whenever they asked him to fuck them. It hurt too much to see it come from Jack, the one man he actually wanted to be with, not just sleep with, and he let himself slip for just a moment as he pried his hands off of his arms so he could hold them instead. ‘You say it came back to you at the Grove? Have you been with anyone since you moved up here?’
‘No one, just Minnie,’ he replied like saying it was easing that weight, and Leo let his head fall forward until he was almost leaning on Jack’s shoulder; this was hard, if he let Jack know that he felt the same it would change everything, he could have what he wanted and be there for him in more ways than just as his producer. He could know how it felt to go home with him like tonight all the time, he could hold him in his bed without having to push him away or worry about those on the other side of his door, he could be the one Jack whispered and smiled at the same way he watched him do to Madeleine for years.
If he told him, he might just be the one Jack loved.
‘I just saw someone, the other week I think it was, right after the show,’ Leo told him, he hadn’t told anyone before, there was no one to tell. ‘We’ve been on and off for a few years, nothing actually serious, just casual fucking whenever we need it, cause I- shit, I never forgot, Jack.’
Jack swallowed as he looked at him in a new light, and it was like a weight had lifted off his own shoulders, but now a new weight was replacing it, because if Jack was like the others, if he did this with him now and then pretended like it’d never happened the next day, Leo would drink himself into a fucking oblivion.
‘So you’ve actually…?’ He couldn’t even say it, so Leo matched him by only nodding. ‘Yeah, me too, that thing they say about the rituals and the- the orgies, christ- it’s all- it’s all true, and once I was in, and they invited me to them, I couldn’t forget again.’ He looked almost ashamed, he might actually be like those other men, and Leo let go of his hands to grab him by the shoulders, he wouldn’t lose him to that shame over who he was now that he was saying it.
‘Jack, hey, listen to me,’ he urged as Jack actually looked away even though he’d been so ready for this, he’d planned on it by coming in here and getting into his bed, begging him to stay, he couldn’t back down now. ‘There’s nothing wrong with you, you hear me? Even if you had to find out again because of that, there’s nothing wrong with either of us, but it’s up to you whether you want to go forward with who you are, or to hide it again.’ Jack refused to look at him as he spoke, but he could see the gears turning, he was thinking, deciding on what his future would be now that they both knew about each other, and Leo was ready to give him all the time Jack needed to think when he suddenly leaned forward and kissed him.
His eyes went wide while Jack’s scrunched shut, this was so different from the way he held Madeleine, and he decided to give him time with this until Jack slowly pulled away; the gears were still turning, and Leo watched as he licked his lips, looked at his producer’s, and leaned in again. This time it was softer, more testing than just going for it, and he pretended like this hadn’t been what he’d been wanting for years as he eased his grip on Jack’s shoulders and let him figure it all out, he wouldn’t rush him.
It felt like he’d forgotten how to kiss, it’d been over a year since Madeleine had died already but he’d figured that he’d been at least hooking up once the guilt of having feelings for others had lessened, but with the way he was kissing him so carefully, like he was afraid to want more let alone touch him, he had to wonder if Jack had just been alone this whole time. It made him want to be patient even more despite his brain telling him to kiss him back already, and it wasn't until Jack rested his hand against Leo’s jaw and tried to deepen it that he allowed himself to. It came easier for Jack after that, like he was remembering it all, like he was getting comfortable in what he wanted, and Leo finally felt what Madeleine did when Jack let out a small sigh against his mouth and started to shift forward.
This was bad, this was exactly what he wanted and Leo didn’t know if he could stop as Jack got more into it, his unbuttoned shirt slipping off his shoulders before he was moving onto Leo’s. Jack was too big to slot himself onto Leo’s lap like the smaller men who wanted him to hold them down and treat them like girls, even like the men who’d never bottomed in their lives but wanted him to show them how, but damn if he wouldn’t try as he gave in and kissed him back with everything he had. He took off his own shirt thanks to Jack’s helpful hands, his own then sliding over Jack’s warm thighs to cup his ass.
He felt different than the others because he was Jack, this was a body he’d been beside every single day since he’d brought him upstairs to get his canceled appointment followed through, one so familiar to him in every way but still feeling so different under his palms and fingers. He knew each curve hidden under those pressed slacks, knew the exact angle his back naturally curved to when he hunched forward, knew how sharp his jawline was as he talked, but it was fresh and new to him as he reacquainted himself with each one. His thighs were full yet they held a slimness that allowed him to partially crawl onto his lap without any trouble. His ass was firm but also gave way in just the way he liked when he kneaded at it. His spine could just slightly be felt when his hand slipped under his undershirt for more, and his jaw worked in an almost devilish way as his clever tongue danced over Leo’s own.
It was all new, but in a way he’d always known all of this, and he groaned when Jack broke the kiss to mouth at his neck.
He shoved him back down onto the pillows, he didn’t know what Jack had done at the Grove and he wouldn’t ask, but for now he would show him how it felt to be loved by a man, not just fucked. It seemed to be exactly what Jack wanted, if he wasn't lying then he’d wanted this for maybe just as long as Leo had, and he returned the favour by leaving a trail of marks where they wouldn’t be seen by the cameras. Jack let out a noise that went straight to Leo’s dick as his hands tangled in his hair, wrapped in his curls and tugged in a way that drove him crazy, was he like this with the others, with Madeleine? 
He didn’t want to think about them now, not even her because he was with her husband, just like how he could never look her in the eye after every single night he got off imagining that the man underneath him was hers.
He lifted Jack’s undershirt over his head and moved down even further, it was clear that he either did really want this or he really hadn’t been with anyone since she got sick because Jack was so hard it looked like he could barely stand it. It made his mouth water at the sight, and he licked his lips before mouthing at his pants, his hands working on his belt. He didn’t give head that often, he preferred to receive it, because that way he could help himself to a cold glass full of dark liquid and guide their heads while he shut his eyes and pretended, but tonight he wanted to if it was going to be for him.
‘Leo…’ Jack moaned as he watched, and he wished he hadn’t taken off his sunglasses so soon because now Jack would know exactly where his eyes were while he did this. He tugged his pants down his hips a little, he was getting too old for this kind of foreplay this late at night with no sleep, but he was sure as hell going to try for as long as his back allowed if it meant getting to look up and see Jack looking back at him with that expression. He looked ready to burst, maybe it was the former and not the latter, and he hoped that it was true as he mouthed him through his briefs and started to palm him.
He waited until Jack was practically begging for it before pulling him out, and he mentally recited what had to be the first prayer he’d said since he was a child in Sunday school as he ran his palm dryly over the shaft just to feel his heat. He felt Jack pulse against his palm, a twitch following as Jack lifted his hips to try and fuck his loose fist, and Leo spit into his palm before stroking Jack more eagerly. His head fell back against the pillows, his legs already tensing as he was forced to look away, and Leo licked his lips again before taking the tip into his mouth and swirling his tongue over the leaking head.
Jack was already panting, a new but familiar desperation was overwhelming him more than he could handle after a year of abstinence, and Leo had to take his mouth away to hush him before continuing; if anyone woke up from their drunken stupors long enough to hear Jack’s voice coming from his room then it was all over, and he eased up just enough for Jack to catch his breath. He waited until he was quieter before taking the rest of him into his mouth as much as he could manage, and he savoured the taste of him and his lust like he would die the moment he forgot it.
Jack covered his mouth before grabbing Leo’s discarded shirt and biting down on it to muffle the noises when he couldn’t keep his hand in place, and Leo glanced up to see his friend bucking his hips and screwing his eyes shut tight as his teeth showed over the fabric. He moaned around him, Jack shaking his head at the feeling because that was too much, he couldn’t handle that, and Leo cocked an eyebrow at him before doing it again. Jack let go of the shirt and needed to cover his mouth again while his other hand found Leo’s hair, tried to get him to stop because it was going to make him come, and he just gripped his hips and bobbed his head a little faster in response.
He was lightly thrusting against his mattress so his moans came easier, he was never this vocal but it was driving Jack wild, and he was ready to be whatever he wanted him to be as the hand in his hair gave him a warning tug. He took him deeper, it was making him choke, he was definitely getting too old for this, but between Jack pulling his hair with both hands to get him off before the pleasure took him over and the growing sounds of his need he knew he’d risk that sore throat to finish this. He had to shut his own eyes when the sight of Jack fucking up into his mouth so he could come nearly pushed him over the edge, and he swallowed down every last drop as he felt his come shoot down his throat between punishing thrusts of the soft head hitting him where no man had been allowed before tonight.
He didn’t pull off until Jack was done, he’d needed that so badly that he’d gone limp the moment he was done, and Leo caught his breath and cleared his throat as he pushed himself back onto his knees; he never swallowed, he didn’t like the taste, but with Jack, like everything else, it was different, and he crawled up until he was practically straddling him. ‘Did anyone ever do that with you at the Grove?’ he rasped, Jack just shaking his head as he covered his eyes with his arm.
‘Always… made me take it… I… I liked it,’ he heaved, and Leo’s dick twitched so hard in his pants that he needed to get them off before he broke the old zipper. He didn’t take himself out, there was no way Jack would want to go again even if he was able to after coming that hard, and he gave himself a few tugs out of sight to ease the pressure before noticing that Jack was watching him again. He breathed a little heavier as he stroked himself again, Jack’s eyes trailing down until there was no denying what he was looking at, Leo doing it again, then again, until he couldn’t take it.
He rested on his heels as he jerked himself off, Jack eagerly watching like he wanted more before he sat up, slid his legs further under Leo’s body so he could get closer. He didn’t ask for permission again, just went for it as he palmed his friend and felt the way his hand moved under his pants, and Leo groaned again at his curious fingers then slipping in beside his own. Jack silently pushed aside his hand to stroke him instead, and his hand was smooth from years of easy labour even though he worked so hard. He braced himself on Jack’s shoulders and moved his hips, properly fucked his hand when Jack pulled him out so he could see him too, the two of them moving with each other in a way that Leo had never done with any of the others.
Jack loved gently, even though there was desire behind it he made love, Leo knew that just from the way he was being held. He pushed aside thoughts of him touching Madeleine just as gently, thoughts he’d kept coming back to when Jack had been a little too affectionate while they were in public, but no matter what they kept returning until Jack noticed his distress. He kissed his neck again, did it the way he liked to, and there were no desperate bites, no marks left behind by men who wanted to get off and go back out there like this wasn't who they were.
Jack kissed him like he loved him, and if Leo were an emotional guy that might’ve wrung something out of him, but it didn’t entirely as he just let his nails dig into his back and leave behind proof that this was happening. ‘I want you to fuck me, as soon as I felt that man inside me I knew I wanted to feel you too,’ Jack whispered to him, not in a way to turn him on more, but to left out this secret that he’d been holding onto for years.
‘You gotta stop touching me in order for that to happen,’ Leo reminded him, but neither made the move to disconnect as his pleasure built higher and higher. Right when he was about to come he grabbed Jack by the wrist and got him to stop, if he just had tonight then he wanted to fuck him too, he wouldn’t accept that Jack wouldn’t pretend like this was more than just longful sex once the sun rose, and he went to his nightstand to pull out his lube and condoms.
‘No, we all had to wear them at the Grove, I want to feel you,’ Jack insisted as he placed his hand over the condom, and Leo shook his head.
‘I’ve been with too many men, and it’s been a while since I was tested with how busy this month was, I won’t put you at risk.’ It wasn't a lie, but he also didn’t want to know how Jack felt around him like that, how warm and tight he’d be when he finally pushed inside.
‘Then stop seeing them,’ Jack blurted out seriously, his hand closing around the condom and wrenching it from Leo’s grip, ‘just stop, you won’t need them anymore if you have- if we-’
‘I won’t tie you down as some random fuck whenever either of us needs it,’ Leo frowned, and Jack shook his head again, his shoulders hunching as he thought about how to word this.
‘You don’t understand, I don’t just want a random fuck, Leo.’ Now Jack was frowning, but Leo wouldn’t believe it, he couldn’t after wanting this for so long, and Jack broke him out of it by kissing him again. He didn’t pull away until Leo was kissing him back, and he brushed his curls aside as he rested his forehead against him, their faces mere inches apart. ‘You know me, you know how much I care for the ones I love, I don’t want you to just be a random fuck,’ he continued in a whisper, they were so close again, and Leo felt his hands grip Jack even harder. ‘I’ve wanted you ever since you helped me get in, long before I saw Minnie.’
‘You chose her,’ Leo finally said, he’d been holding it in for so long, and Jack nodded this time.
‘I loved her more than I have any other woman, but I’ve always loved you, too, I just couldn’t have you, not out there,’ Jack confessed to him, and for once Leo let himself get sentimental as he hugged Jack tightly.
‘You won’t be able to have me out there even after this, they don’t understand people like us,’ he said softly, Jack nodding again, ‘I can live with it with those men, I don’t love any of them, but you-’
Jack froze as Leo realized what he’d said, he’d admitted it, he hadn’t wanted to but it’d just come out, but Jack didn’t look like he was going to back out now that he knew exactly what was going on here. ‘As long as we’re here, they’ll never find us,’ he murmured so softly it was almost below a whisper, said only for him, ‘we don’t need the penthouse or my place, we can just come here.’
‘They’ll find it eventually if we keep being seen together, we can only explain away so much to those vultures out there,’ Leo said bitterly, but Jack was soft, he was so soft as he was the one to hush him, this was how he loved.
‘I’ve always pushed the boundaries on Night Owls, it might skyrocket the ratings if they learned that Mr. Midnight was a homosexual, or whatever I am,’ he didn’t exactly joke, but Leo still coughed out a laugh all the same.
‘A widowed TV host and his homosexual producer revealing themselves to be getting together behind the scenes, the media will have a fucking frenzy with that one,’ he agreed, and Jack kissed him again before tossing the condom out of reach even though there were more in the nightstand.
‘Exactly, so why don’t you fuck me for tonight, and we’ll figure this out tomorrow, just like we always do?’ Jack suggested as he broke away to lean back against the headboard; Leo didn’t need to be convinced any more after that, and together they finished stripping each other like this was their first time and they couldn’t wait to get to the main event. Jack was already getting hard as they ditched their clothes and started kissing again, and Leo was about to touch him before thinking of something. He quickly got up and locked his door, no one would be able to come in no matter what they heard now, and it wasn't perfect but it would have to do as he rejoined Jack on the bed.
‘How do you want me to do this, old man?’ Leo teased now that Jack had finally passed the final threshold before he reached 50s as of this year, and he thought about it before getting on his hands and knees. ‘That’s a young man’s position, you think your knees can handle it?’
‘You think you can make me come again before your back acts up?’ Jack teased right back since they were only a few months apart, and he smirked and rubbed himself against his ass to get him to shut up; this felt right, this was how they’d always talked even though Jack was pushing back against his dick for just a little more until he could fuck him. If he’d just bit the bullet and asked back then, threw out some subtle hints that maybe he was interested, could they have had this all this time? Could he have been the one Jack came home to after every show instead of her? He didn’t know with how long it took either of them to say something, but he was glad he could have it now as he lubed himself up and started to stretch Jack out. ‘Don’t waste time, they never did, we can go slow the next time we’re here, I want to spend the whole night with you.’
Leo didn’t like the thought of who knew how many men treating Jack like that, but they could unpack all of that later, for now he really needed to get off now that it was coming back to him again. He teased Jack for just a moment before pushing in, and it was too tight but he didn’t seem to mind it, Leo would have to teach him about actual gay foreplay at this rate, but Jack was right, they could do it when they could spend the whole night together. It took him another moment to set a pace, Jack felt even better than he expected and he couldn’t get enough of the slow drag until the head was catching on his rim and making him keen, and he repeated the action a few times before getting to it.
He was used to the position, to the feeling and sounds of men under him like this, but he wanted to forget it all and learn it all again as he ran his hands over Jack’s back and started to thrust. Already it sounded like it was too much for him, like he was about to come if he kept this up, and he alternated between going fast and hard enough to nearly make him shout and slowing down until it almost felt like torture. He rolled his hips as he slowed, made Jack feel every inch of him as he did, and he could see his arms shaking in the dim light, he couldn’t hold himself up for long at this rate. He splayed his hand over his lower back and pushed as he traveled down to the base of his skull, and he guided Jack to rest on the pillows before trailing his hand over his jaw and to his mouth.
‘Suck.’
Jack obeyed, he must’ve been used to this command because he gave a wanton clench as he ran his tongue over Leo’s fingers, and he shuddered at the feeling before fucking him hard again. Jack moaned around his fingers as they both got what they wanted, two men who couldn’t even hold hands out there finding solace in fucking in silence, in the safety of his home that was currently compromised by the people he’d so willingly invited in. They couldn’t take this from him, when Jack had married Madeleine he’d thought that he’d have to let him go for good, but fate had allowed him just this one happiness that hadn’t been bought, hadn’t been given to him on a silver platter.
It was real, it was his, and he removed his fingers from Jack’s mouth so he could grip him by the hip and the shoulder as his orgasm started to build.
Sweat was dripping off the both of them from the exertion, the bed creaking with each thrust, Jack’s sounds muffled by the pillows as he hung on for dear life, Leo so expertly quiet after a lifetime of hiding that this was easy for him until Jack turned his head to the side. He looked back at him, eyes half lidded, mouth slightly agape with a smile, and in that expression Leo saw not lust but love, he really did love him, and he reached around to quickly jerk Jack off until he was coming just so he didn’t have to look at that expression any longer. He practically cried into the pillow at the feeling of Leo still going until the sensation was too much and he came too, and he’d never had sex without a condom before, but fuck if he didn’t like the feeling of coming inside the man he was resting his forehead against.
He didn’t pull out at first, he physically couldn’t, but eventually he had to, they needed to get cleaned up and one of them needed to find a different place to sleep before the others awoke and saw them leaving together. He was already thinking about the dawn but Jack was still a Night Owl, and when Leo pulled out and moved to get up Jack was quick to pull him right back down. They bounced on the mattress and it gave a concernedly loud creak that had them both freeze, but there were no bangs on the wall to shut up, no signs that anyone had heard them at all.
Leo lay with his back to his friend, or whatever he was now, before he couldn’t take it anymore and turned to face him, and he wasn't surprised to see how wet Jack’s cheeks were. Here it came, now that it was over he’d realize that he’d said a lot of things he didn’t mean like all the others still in hiding, he wasn't ready for a relationship in general, let alone one with a man, the end was coming before the sun rose. But Jack never said he regretted it, he was crying but it wasn't in sorrow this time, and Leo just laid there as Jack reached up to trace the shapes of his face, learned them more intimately than anyone else ever had before.
‘I nearly asked you to dinner that day, when we were in the elevator,’ he said vaguely, but Leo still knew he meant the day they’d met. ‘I was so scared being up here, thought for sure I was going to fail and that I’d have to go back to Chicago to beg for my job back, but you… you’d been the first to see me, you believed in me, how- how’s a guy not supposed to fall in love with that?’
Leo swallowed, he’d know those words anywhere no matter how they were changed, and he swore he wasn't sentimental, but he thought he might be as Jack looked up at him with a vulnerability he hadn’t seen since the funeral. ‘It’s a good thing you didn’t, I would've made you buy,’ he joked, but Jack was serious, and he didn’t say anything as the other man leaned in to kiss him again. He didn’t know what an afterglow was like, he was used to the others getting up and leaving while he had a smoke and got back to work, that was what worked best for him now that he’d gotten it out of his system and could go another week pretending that he was into all the pretty girls who tried to woo him to get onto the show, just for a little bit.
He turned them all down, he couldn’t fake an orgasm to save his life and any one of those girls could out him on that when he didn’t let them on the show after such a poor performance, but now-
Now he wouldn’t have to, they would never ask Jack himself after crying on live TV over his wife, and now Jack could come to him whenever one of the guests got a little too friendly, he didn’t have to watch him entertain them anymore. He chuckled to himself when they parted before rolling over to grab a smoke from the other nightstand, losing himself in the thought all the way up to flicking the ignitor, and he stopped with the cigarette in his mouth before remembering that Jack had quit. He quickly apologized but Jack just took it from him, lit it up, and enjoyed one single puff before handing it over.
‘I’m more concerned with the drinking, little late to cure more lung cancer if I’ve got it,’ he figured as Leo took his own puff, although that thought of that made him falter and hold it a bit too long.
‘Should we get that checked when I make sure I’m clean this weekend?’ he suggested, but Jack shook his head.
‘Already did, it skipped me, but if you want to…’ He trailed off, Leo exhaling again before putting it out, he could live with that much. ‘I don’t know what I’d do if I lost you to it too, to see you like that, I wouldn’t be able to come back to the studio knowing you weren’t there, it was hard enough going home to an empty house back then,’ he admitted, and Leo swore to himself that he’d quit too, cold turkey, if it meant he wouldn’t put the man beside him through that again.
‘We can do that, then,’ he decided, their first decision as a whatever they were, and Jack slightly smiled at him as another tear fell. ‘Christ, never thought I’d get clean because of anyone, let alone because I wanna do it for you,’ he muttered like he truly couldn’t believe it, but deep down he knew that he would’ve done it sooner had Jack asked, would’ve done it the moment Madeleine got diagnosed if he’d said those words to him. He knew it, and he could’ve sworn that Jack knew it too as he found his hand and held it. 
Jack was always a cuddler, he liked to be near those he loved and it made him inseparable from Madeleine until the end, and while Leo exactly wasn't the physical affection type, he never could keep his hands off Jack, and he let him curl up against him with a sigh that didn’t sound as forced as he’d wanted.
‘Y'know we can’t tell Gus about us, right?’ he said to the ceiling when Jack started to fall asleep again, and he came back to life at the sound of Leo’s voice. ‘He’s a God fearing man, he’s bound to have a sermon or two ready if either of us let it slip.’
‘Gus is fine, he seemed surprisingly interested when I casually pitched to him the possibility of having Bianca and her wife come on to talk about their lives, they’ve been talking about telling their family,’ Jack yawned, Leo raising an eyebrow at him again.
‘Pretty personal confession to a patient,’ he frowned, and Jack shook his head as the sleep started to take him again.
‘I told her about myself, which prompted her to tell me, it’s because of her that I wanted to do this tonight,’ he confessed, he was too tired to save this for when he was fully conscious, and Leo rubbed at his eyes again at the mental image of Jack coming out to some random woman only to come to the conclusion that he needed to finally confess after what was probably a very long session about the both of them, not just him.
‘Should’ve told me after how long we’ve known each other, but… I guess I get it,’ he figured, Jack nodding just slightly over his chest, he was almost gone. ‘So we get these lesbians on air, talk about therapy or something, and then you and I announce to the whole world that we’re now, what? Fucking, dating, living together?’ Jack mumbled out a confirmation, he had no idea what was going on on the other side of his eyelids. ‘It sounds nice, honestly, to imagine a world where we could do that and now lose the show, and the crew.’ No response, just light snoring. ‘It’s nearly the 80s now, dawn of a new decade coming up in just a couple years, maybe times will change before the next century, maybe one day you can talk to everyone about your own life, and I’ll be out there with you.’
He was talking too much only because he knew Jack couldn’t hear him, he was sentimental.
‘I think I want that for us, if we’re really doing this, fuck, 49 years of hiding and sleeping around with whoever I could find out there, I dunno how you did it for so long,’ he continued quietly, or maybe he was thinking it, sleep was starting to take him too now that he finally knew how warm an afterglow could be. Jack had pulled himself over his arm, and Leo fought to bend it until he could hold him back, the latter now even more on his chest to allow it. He looked down at him in the dark, he’d wanted this sight for so long that he still couldn’t believe he could have it, and he was definitely sentimental as he leaned over just enough to press a kiss to the top of Jack’s head.
He felt him grin against his bare chest before draping a leg over him, he must’ve smothered Madeleine all the time in their bed back in the day, and he shut his eyes and willed her from his mind for good. He apologized to her as she left, but Jack wasn't the only one who hadn’t let her go in all this time, and he prayed that she could finally rest as he ran his fingers through the short strands at the back of Jack’s neck, he’d take care of him for her, for the both of them, from now on.
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applemccartney · 8 months ago
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i have one (1) oc made for the purpose of selfshipping and his name is connor. him and jack delroy have freak sex
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selfindulgentfandomstuff · 1 month ago
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Ummm I like them. Be so niceys to me pls and thx 👍💗
(Btw for any other Jack D/elroy selfshippers/oc x canon shippers who might see this, I’m fine sharing him!/gen pls see my pinned for who I’m not comfortable sharing if you plan on interacting! I can’t force you to but I’d really appreciate it <3)
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selfindulgentfandomstuff · 29 days ago
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Of course I had to add Essie bc I’m a selfship blog first and foremost! (Their glasses are optional btw so that’s why you don’t see them in some art of her!)
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Jack Delroy (left): he/him
Esther ‘Essie’ Watkins (right): they/she
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Proship + adjacent DNI
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selfindulgentfandomstuff · 1 month ago
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Separate post for this because it’s goooood (not to pat myself on the back lol)
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selfindulgentfandomstuff · 1 month ago
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why do you associate the songs with them (id eleborate but chronic makes thinking hard)
WOOO HII no worries at all, this is great!/gen
OKAY SOOO
I’m just gonna go song by song and write a little blurb on each one! It won’t be long and detailed but you’ll get the gist of it haha!
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Short list of songs that are unbelievably Jack x Essie coded in one way or another
- “Goodbye Yellow Brick Road” by Elton John
Just. This song over all, peak representation of the way that Essie feels kind of tethered to Jack in a way and when she finally comes to the realization that he’s no good for her after the incident in the mental hospital, the way she is ultimately able to move on with her life .. ooughh/pos
- “Hermit the Frog” by MARINA
OH MY GODDD/pos so much abt this one, everything from, “I was the wrong damn girl in the wrong damn room” (Essie was never even supposed to be at that party she met Jack at to begin with) to the recurring mentions of ‘the devil’ with “I can’t help the devil likes to make my heart a double bed and I can’t help he sometimes likes to come and rest his little head” and “I went to the doctors believing the devil had control over me and I was finding it hard to breathe and finding it hard to fight the feeling” OOUUGHHH GOOD SHIT
- “Religion” by Lana Del Rey
The only partially requited devotion (Essie was on the giving end and Jack the taking) of having your lover be an idol of religion in your mind; the religious thematic tie in with the satanic themes of canon; the clear light that Jack brought into Esther’s life despite the fact that he was also bringing them down…
- “Haunted House” by Mckenna Grace
This ENTIRE song really, but particularly this bit:
“I get reminiscent
When somebody says your name
Almost glad I miss it
'Cause it's better than not feeling a single thing
Even after all the white lies, empty goodbyes
All the tears and all the times
You weren't there when I needed you to be
Hoping you're right where you wanna be
Even if it's not with me”
- “Favorite” by Isabel LaRosa
This is the origin of my ship tag for them, “darling can I be your favorite?” Of course, but also like. The implications of such a question.. can she be his favorite, ever? Will he ever love anyone the way he loved Minnie? No, probably not, she thinks.
- “Curses” by The Crane Wives
Idk man just listen to the song 😭 you’ll see what I mean
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selfindulgentfandomstuff · 1 month ago
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From soemthing bigger I’m working on that turned out really nice in its own right!!
Jack Delroy!!
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selfindulgentfandomstuff · 4 months ago
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Jack Delroy doodles in my English notebook lol these are kinda bad but I want to post stuff so here they are lmaooo
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selfindulgentfandomstuff · 30 days ago
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Jack Delroy, man that you are…
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Proship + adjacent DNI
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selfindulgentfandomstuff · 15 days ago
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I tried actually properly rendering digitally for the first time.
I dunno guys this was a loooot of work + time for a Not Very Good result 😭😭😭
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Proship + adjacent DNI
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selfindulgentfandomstuff · 3 days ago
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I lowkey hate this but idc I spent sooo long on it so y’all have to look at this lol
Sketch + og screenshot below
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selfindulgentfandomstuff · 4 days ago
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Sketch stage of a screenshot redraw I’m doing :3
I’m not like amazingly happy with this and I may redo parts of it when I finish it digitally but for now this is fine lol
Og screenshot under cut!
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selfindulgentfandomstuff · 5 days ago
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Some lighthearted AU offshoot where Jack’s relationship with Esther goes public and he eventually introduces her to the public so they’ll just stop speculating and freaking her out 😭
Is this made with that ask game I just reblogged in mind? Yes. Absolutely/lh
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Jack D/elroy (left): he/him
Esther ‘Essie’ Watkins (right): they/she
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Proship + adjacent + other Murdoc selfshippers/oc x canon shippers DNI
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selfindulgentfandomstuff · 1 month ago
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Some alternatively stylized Jack Delroy doodles!! Not suuuuper happy with these but I rather like the top one!
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selfindulgentfandomstuff · 1 month ago
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WOOOO ANGST MOMENT!!!!
My headcanon/self insert lore weaved into the canon events of LNWTD!!
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Esther ‘Essie’ Watkins (they/she) is a non-binary girl!
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Proship + adjacent DNI
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