Kylar and Gabriel cosplaying Kaito and Hatsune Miku, posing for a picture. It mimics the meme format of two individuals on a sidewalk with the one on the left’s face mostly obscured by shadow, reading “why dis 🥷🏾 look so mad 😭😭😭”. Instead of the ninja emoji, the logo for V1 KAITO is used. The background is a photo I took at an anime con and edited out the cosplayer as well as individuals’ faces.

Kylar and Gabriel make it to an anime convention to couple cosplay! It takes a while for Kylar to get used to people taking Gabriel’s picture (even if he’s in it too)…
For #DoLtober theme “Photograph”!
#DoLtober2025 #DoL #OC #KylartheLoner

Adryen and Whitney in dog and devil costumes on a background that says, “Happy Halloween!” Whitney holds a yellow leash attached to Adryen’s collar and tugs it tightly while grinning. Adryen smiles and holds his hands up like paws, obedient and smitten.

🎃 It’s Halloween~! 🖤🧡💚💜
Which is also the final #DoLtober prompt, so here’s Adryen and Whitney celebrating in costume together!
Are these really costumes for them though..? 🐶😈
#DoLtober2025 #DoL #OC

Grezy and Robin standing beside each other, their arms linked as they laugh together while leading some of the younger orphans through town trick or treating. Grezy and Robin both wear witch costumes; Grezy has a purple dress while Robin has a blue one. This is based on Robin's halloween event in the game where the PC can encourage Robin to explore his budding desire to cross dress. The young orphans behind them are dressed in costumes: the two on the left are dressed as two of my vtuber friends who participated in doltober (Ursa and Rainy), and the two on the right are Kotaro-san from Zombie land saga and the last one is loosely based on my vtuber design). Their dialog from left to right is: "I'm a vtuber!/Me too!/Fran...choochoo ?"

DoLtober Day 31~ Halloween

I started this challenge with Robin so it seemed fitting I end the challenge with him as well <3

Happy Halloween from two seriously cute witches!
🎃💜💙🧙‍♀️

#dol #doltober #doltober2025

A close up shot of from the shoulders up of the Ivory Wraith in front of a blood moon. Their eyes are the same red as the blood moon.

DoLtober Day 30~ Blood Moon

You've got to be careful during the last night of every month...the moon turns red and a certain ghost may very well try and possess you...

#dol #doltober #doltober2025

Sirris touches his wedding ring alongside his late partner's before buttoning up his shirt while getting ready in the morning. His expression is neutral but leans towards somber. His nails are painted the color of Sydney's eyes. I headcanon that he does this, paint them a color that brings him joy, whenever he is feeling down. I see him switching between colors that remind him of his son and his partner.

DoLtober Day 29~ Ring

Just a man and his memories...

(I want to hug Sirris ;3; )

#dol #doltober #doltober2025

My DoL self insert Grezy, sits on top of Sydney, the latter of whom is a but scratched up and covered in a few stray leaves and flower petals. Moments earlier, he stummbled through a flowered bush in the temple's garden, hence the bits of nature in hair and on his robes. Grezy, while looking down at him, smiles and blushes as he asks if 'she will take care of him'; referring to his minor injuries as well as 'subtly' suggesting things as she sits on top of him. She says she will and asks if he wants her to look anywhere specific; fully aware he may need her in another way. He responds back flirtatious, saying she should check his lips. "I think they're scratched"; he says while looking forward to kissing her.

DoLtober Day 28~ Doctor

Who needs Dr. Harper!
Grezy is absolutely here for doctoring Sydney after his little fall in the Temple garden. ;3

#dol #doltober #doltober2025

Sketches of Gabriel as a full transformed harpy, largely resembling a swan. They are titled, “Noted on Gabriel (100% beast)” and signed by Kylar with his first initial. From left to right: sketch of His open beak revealing canines, the notes saying “fangs, canine(?), very pretty, I want Him to bite me”; profile sketch of Him laying down with notes, “usual feathers are bigger (cheek, chest, etc), pretty blue eyes as always, all gold, base shape is swan!, not swan flippers- talons (owl?)(so pretty); sketch of Him diving and looking angry with note “feathers ruffle (cute); sketch of Him facing more forward with a wing unfurled with notes “strong muscles (still), eyes face forward (predator)”; and lastly a sketch of Him walking away and looking over His shoulder with notes, “breathtaking as a beast too, I’m soooo lucky” with hearts drawn beside Him.

Kylar’s notes on Gabriel’s “100% beast” form! Harpy or humanoid, Kylar is smitten~
Since He’s mostly bird like this, I thought it’d be nice to draw Him for #DoLtober prompt “Flight”!
#DoLtober2025 #DoL #OC [Gabriel]

My dol oc Jay masturbating two dicks, one in each hand, as a third is aimed at his chest. All three climax onto his body via his shoulders and his chest. He blushes, looking stimulated as he thinks to himself, "if doing this makes me a slut, then hell yes I am" He is just having a good time uwu

DoLtober Day 27~ Slut

Jay is proud to be one; no shame in having fun!

#dol #doltober #doltober2025

Gabriel leans over Kylar’s bare back, carving into it with Kylar’s knife. He appears very moved, face red and eyes shimmering. Nonetheless, His hands are steady. Kylar’s face is turned away, but it’s clearly red as well, and he’s crying. He trembles lightly. Blood drips down from the symbol Gabriel is carving into him. They talk through the process, starting with Gabriel: “I’ve researched this very thoroughly. You’re in good hands.” “I know.” “I’ll look after your recovery just as thoroughly.” “I trust you.” “You’ll have my symbol carved into you forever.. right where your writing rests permanently on me.” “I love you s-so much…”

Kylar requests a scarification tattoo of Gabriel’s religious mark, made with his treasured knife. Naturally, Gabriel takes this very seriously- both in researching what’s needed and in processing the emotional weight of the request.
(For the #DoLtober prompt “Knife”)
#DoL #DoLtober2025 #OC

Sydney holds a photo album and looks at a picture of a younger teen Grezy and Robin, both of them sporting really short hair cuts. Syd is surprised, saying "Wait is that..." while Grezy cuts in and affirms it is indeed her. "Yup. Me.../ I hated that cut." This is based on story in my notes that deals with Syd being unsure about what to do regarding getting his hair cut and Grezy talks to him about her awkward hair cuts in an effort to show him that although she didn't like her hair being cut short, it grew back and she was able to fully realize just how much she preferred having long hair as a result.

DoLtober Day 26~ Photograph

Ah fun awkward hair memories.....

#dol #doltober #doltober2025

Three chibi drawings of Quinn with labels below them from left to right: Angel, Fallen, and Fox. Each depict him in his transformation at the time. The Angel transformation in spring with a black streak in his hair to suggest he’s dating Sydney, the Fallen Angel transformation in summer with an orange streak on the other side of his hair to show he’s dating Robin now too, and his Fox transformation in fall with his former halo and wings purged.

No pc of mine has gone through more transformations than Quinn, so for #DoLtober prompt “Transformation”, I chose to depict each of his! He’s been the happiest as a fox man~
#DoLtober2025 #DoL #OC

Avery stands tall with his hands in his pockets and eyes open while Adryen bends over to kiss him. Adryen holds his own hands, raised but kept to himself, as he sweats nervously. Both wear formal attire.

“Kiss” is but a silent order obeyed by Adryen after a date with Avery. While Adryen desperately hopes for more, Avery quietly considers if ‘more’ is good for his heart.

For #DoLtober #DoLtober2025 #DoL #OC #AverytheBusinessman

Gabriel and Kylar lay on their stomachs in Gabriel’s bed, light casting from the window out of frame as well as the mobile phone they both hover over on the mattress. As they look at the device, Gabriel says, “Olivine’s maid outfit is surprisingly tasteful.” Kylar agrees, “S-surprisingly…” Gabriel elaborates, “Even his priest attire is more scandalous!” This makes Kylar laugh, “Haha, it really is, huh?” Gabriel appears to be laughing too.

For the #DoLtober prompt “Priest”, it feels silly to draw characters react to a priest from a different game, but it’s exactly what I chose to do. I’ve drawn Kylar playing Nu:Carnival alone, but he plays with Gabriel too~
#DoL #DoLtober2025 #OC #KylartheLoner

Chibi, ink art of Gabriel as Princess Zelda holding close the hands of Kylar as Link. Gabriel shines as He smiles down at Kylar, and Kylar stares back up with a big smile himself.

💙 In every world. In every time. 💚

For #DoLtober prompt “Videogame”, I drew an AU where Gabriel and Kylar are Zelda and Link from Skyward Sword! They’d happily reunite across time for eternity~
#DoL #DoLtober2025 #OC #KylartheLoner

Grezy flies up high in the sky and floats up above the clouds, relaxing without her top on.

DoLtober Day 25~ Flight

When you got wings sometimes you just gotta fly up super high and take off societal shackles (aka your bra) and just breathe.

#dol #doltober #doltober2025

Kylar holding his knife, body trembling as he stares at his attacker with a frightened expression. His clothes and face are battered. A small bit of blood is seen on the corner of his mouth.

DoLtober Day 24~ Knife

This is somewhat based on the event when Whitney picks a fight with Kylar.

Kylar only grabs his knife at the end of the event, in a desperate attempt at protecting himself.

#doltober #doltober2025 #dol

Two panels featuring Kylar talking to Robin at the lockers and Gabriel talking to Sydney in the library. Robin asks Kylar, “Did you have a nice Valentine’s Day, Kylar?” Similarly, Sydney asks Gabriel, “How was your Valentine’s, Gabe?” Kylar and Gabriel have the same thoughts described as, “18+ CW Tags Include: Lingerie, Shibari, Aphrodisiacs, Oral, Cumming Untouched, Multiple Orgasms, Subspace, BDSM,” with a lot of the words being cropped off as they trail on. Kylar looks away with a red face, Gabriel closes His eyes in reflection, and both of them say, “It was really good,” though Kylar stutters a bit.

For #DoLtober prompt “Valentines” I wanted to draw the lingerie Gabriel wore for the day, but I know I’d spend too much time on it, so I went with something simpler: Kylar and Gabriel recalling it the day after!
#DoLtober2025 #DoL #OC
[Robin, Sydney]

My dol self isert Grezy, halo above her head, standing with her arms behind her back while smiling and showing off her pink hawk wings and smaller angel wings. DoL has animal and spiritual transformations and Grezy has the hawk and angel transformations.

DoLtober Day 23~ Transformation

I don't usually draw Grezy with her two sets of wings or halo, but she definitely has em!

#dol #doltober #doltober2025

Gabriel sits beside a pool talking to 3 people within it looking up at Him. He covers His body with His wings and long hair as He drinks from a beer bottle. Behind Him are 6 empty bottles neatly placed beside their caps. He appears very disoriented and flushed, clearly drunk. The people in the pool say, “Tell us more!” And chant “Yeah!” Gabriel answers through slurring, “Mmore? What greedy curiosity. Noneth’less, I’ll regale you with the time Kylar and I were in his,” and the story trails off. Kylar’s name is emphasized with a heart beside it. Empty bottles from others lay around the poolside as well.

The #DoLtober prompt “Drink” had me consider the time Gabriel got plastered to cope with attending a nude-only “pool party” for the sake of higher social standing. He (and His stories) got very popular after this night!
#DoLtober2025 #DoL #OC

My interpretation of Sydney from DoL standing with his hands on his hips while he is wearing the sexy priest costume. This is based on a potential fic I have in my notes where Sydney wears the outfit for Halloween, changing into it before he and Grezy go to the Halloween party at the lake. Behind him is a forest setting, fog around him and a full moon overhead.

DoLtober Day 21~ Priest

This is based on a fic I mused about in my notes, where Sydney joins the PC at the Forest lake for the Halloween Party!

I just want him to wear this outfit so much aaaaaa UwU

#dol #doltober #doltober2025

Grezy and Sydney lay in bed snuggled up together as they listen to music playing in the game she's playing (Undertale) She says "I love the music for this game. I could listen to it for hours" and Sydney says "So could I"

DoLtober Day 20~ Video Game

Grezy shares one of her favorite games with Sydney <3
Just a peaceful night spent with really good game

#doltober #doltober2025 #dol

My DoL OC Jay, gives my interpretation of Kylar from DoL a Valentine's card and a lil flower as a gift for Valentine's day. Kylar is blushing super hard and is holding his hands close to his chest. Hearts float above his head as he looks at the little gift. Jay considers Kylar a friend with benefits, however Kylar sees Jay as a lover.

DoLtober Day 19~ Valentine

I almost drew Syd for this (surprising no one) but I ended up going with Jay giving Kylar a gift because I thought it would be cute!
They may not necessarily be on the same page relationship wise, but I think they both are happy here.

#doltober #doltober2025

In the first panel, Gabriel lays in His bed, presses His mouth to a phallic toy, and makes eye contact with a live feed from the viewer pov. He says, “If you’re unavailable, I’ll have to settle for now…” In the last panel, Kylar leaps in from Gabriel’s bedroom window and smacks the toy out of Gabriel’s hand while pulling his shorts down with his other hand. He shouts, “It could never compare to what we have!” Gabriel is unfazed and incredibly pleased as He responds, “Don’t I know it~” Background elements include a large, framed portrait of Gabriel beside His bed (made by Kylar); the words “I love you -K” carved into His bedside table; a sticky note stuck to the table with a heart and their initials in it; the owl plush on the bedside table that the surveillance pov was from; a consent pillow that says “YES” that was on the windowsill but fell over when Kylar hopped in; and a One Piece skull and bones on Kylar’s t-shirt.

Combined my pieces for #DoLtober prompts “Toys” and “Jealousy”. Gabriel continues to thrive under Kylar’s red flags: surveillance, breaking in, jealousy- all embraced to His benefit✨🚩🚩🚩
#DoLtober2025 #DoL #KylartheLoner #OC #DegreesofLewdity

A younger Kylar sits on the edge of his bed, facing away with his legs off the side. He cries and holds his left thigh as he makes cuts into it with a knife. Words beside him repeat, “I’m not sick,” until they become simply, “I’m not.” His headboard is covered in trash and art supplies, and the only visible items on his bedside table are an alarm clock, a lamp, and an owl plush. He wears an oversized pajama top. The room is dark.

CW⚠️: self harm
For #DoLtober prompt “Nightmares”.
I imagine Kylar had a lot of them growing up after his parents ‘got sick’. I don’t imagine he knew how to cope with them well.
#DoLtober2025 #DoL #DegreesofLewdity #KylartheLoner

From left to right: Quinn, Robin, and Sydney, colored in red, orange, and black. The theee of them face a clothing rack with a variety of lingerie on hangers. Quinn looks at one with a chest bow and corset design with laced cups. He smiles wide with stars in his eyes, grabbing robins wrist as he says, “Robin, you’d look so hot in this!!!” Robin rubs his neck and points to himself timidly, breaking out in a sweat as he asks, “Me??? I… would?” Sydney taps his knuckles on Robin’s other arm and grins suggestively at him, offering, “If you want to try it on, we could take you to the storage room and lend a hand~l

Quinn and Sydney invite Robin to their workplace: the adult shop! They may end up abusing their staff privileges…
For #DoLtober prompt “Lingerie”! Someday I’ll color this proper- and maybe draw Robin in their find…

#DoLtober2025 #RobintheOrphan #SydneytheFallen #DoL #OC
#DegreesofLewdity [QRS]

My interpretation of Kylar from DoL staring straight ahead looking at the PC (in this case, Jay) looking jealous with red tinging his green eyes as tears bubble up. His thoughts depicted in red writing surrounds him; saying who is that?/..../why are you smiling?/stop laughing/please.../No No No

My interpretation of Kylar from DoL staring straight ahead looking at the PC (in this case, Jay) looking jealous with red tinging his green eyes as tears bubble up. '++ Jealousy' reads near his forehead.

DoLtober Day 17~ Jealousy

What I imagine goes through Kylar's mind when he sees the PC talking to anyone else.

#dol #doltober #doltober2025

My DoL self insert Grezy, wearing a purple babydoll dress from the game holds a riding crop in her hands as she walks towards Sydney telling him, "You turn, Syd". A look at Sydney shows he is very excited with hearts for eyes as he blushes and says, "Beloved~"

DoLtober Day 16~ Toys

Sydney's had this coming for a while now.

At least he's excited uwu

#dol #doltober #doltober2025

My interpretation of Sydney from DoL getting close to the viewer while purple tentacles appear around him. A fire burns in the background. This is based on the Sydney Nightmare event in the game.

DoLtober Day 15~ Nightmare

I dunno...I think this Nightmare could be fun...>3>

#dol #doltober #doltober2025

A sketch concept of what Sam the cafe owner from Degrees of Lewdity looks like in my playthrough. She’s drying a mug with a dish towel in her hands and eyeing the viewer as she greets them with a, “Hey, cutie!”

Belated #DoLtober prompt “Cafe” encouraged me to sketch a design for the cafe owner: Sam! I like to think she has colorful hair, but im just sketchin’ today, so I’ll choose exactly what colors another time~
☕️🌈

#DoLtober2025 #DoL #SamtheCafeOwner #DegreesofLewdity

Jay holds a bowl, smiling happily and blushing, dick out and hard, as he greets Avery home. He is wearing purple and blue lingerie in the hopes of turning Avery on.

DoLtober Day 14~ Lingerie

Jay really likes living with Avery <3

#dol #doltober #doltober2025