1 - 20 of 114 Bookmarked Items in Sinsmas Holiday (Helluva Boss)

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  1. 35

    Underneath The Mistletoe by

    Fandoms: Hazbin Hotel (Cartoon)  

    23 Dec 2024

    Tags
    Summary

    Wanting the Radio Demon but not knowing how to broach the topic with him, Lucifer decides to hang up mistletoe around the hotel for the holiday season. And it would've been a great idea, too, if Alastor hadn't gone around taking it all back down again like it had personally insulted him. Needing to find out why, the Devil is pleasantly surprised at why the demon was doing so.

    Anything to make those two idiots kiss...

    Language:
    English
    Words:
    1,890
    Chapters:
    1/1
    Comments:
    14
    Kudos:
    214
    Bookmarks:
    35
    Hits:
    1,232

  2. 34

    Vicious Delicious. by

    Fandoms: Hazbin Hotel (Cartoon)  

    06 Dec 2025

    Tags
    Summary

    Angel didn’t know what to expect when Valentino lost his soul over to the gambling demon. He just knew he wanted to get out of it.

    Hiyaa! This is a re-write of one of my old fics ‘please stop hurting me’ as I HEAVILY dislike it! So I hope you enjoy this one🤭♥️

    Updated once a week!

    Language:
    English
    Words:
    32,109
    Chapters:
    7/20
    Comments:
    56
    Kudos:
    118
    Bookmarks:
    34
    Hits:
    2,356

  3. 2

    A Very Charlastor Christmas by

    Fandoms: Hazbin Hotel (Cartoon)  

    06 Dec 2025

    Tags
    Summary

    Charlie and Alastor enjoy a magical winter together.

    A Secret Santa Gift Exchange fic!

    Language:
    English
    Words:
    5,324
    Chapters:
    1/1
    Comments:
    1
    Kudos:
    10
    Bookmarks:
    2
    Hits:
    76

  4. *

    Heavenly Choir by

    Fandoms: Hazbin Hotel (Cartoon)  

    27 Dec 2024

    Tags
    Summary

    His connection to the Heavenly Choir was yet another thing Lucifer had lost in his Fall.

    And yet, every year around Sinsmas, no matter how much it hurts, he plays his part of the Song anyway. Maybe one year they will realise that he is still there, still hears the melody of the universe itself. Maybe they will play with him again. They won't. Stop deluding yourself.

    Hearing the incomplete Song fills Alastor with so much wrath, he decides it is high time someone forces some angelic hands. Good thing audio broadcasts are his speciality.

    Series
    Language:
    English
    Words:
    8,916
    Chapters:
    2/2
    Comments:
    102
    Kudos:
    753
    Bookmarks:
    149
    Hits:
    6,838

  5. 8

    Kiss Me At Midnight by

    Fandoms: Hazbin Hotel (Cartoon)  

    31 Dec 2024

    Tags
    Language:
    English
    Words:
    3,711
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    55
    Bookmarks:
    8
    Hits:
    359

  6. 44

    Yaoi!!! On Ice by

    Fandoms: Hazbin Hotel (Cartoon)  

    25 Dec 2024

    Tags
    Summary

    On the day Hell froze over, the first thing the Hazbin Hotel gang sees is a giant frozen lake. Naturally, it must be used for ice-skating! Unfortunately, Lucifer finds himself partnered up with Alastor for this endeavor, and he's happy to tell anyone how horrible of an idea that is. Then again, there's something strangely magical about the ice... and the man teaching him what it means to truly be free.

    Language:
    English
    Words:
    18,557
    Chapters:
    1/1
    Collections:
    1
    Comments:
    30
    Kudos:
    184
    Bookmarks:
    44
    Hits:
    2,031

  7. 21

    A Hellish Little Sinsmas by

    Fandoms: Hazbin Hotel (Cartoon)  

    04 Dec 2025

    Tags
    Summary

    Charlie Morningstar is determined to bring back the Helliday traditions of her childhood — Hellsgiving dinner, the Twelve Days of Sinsmas, over-the-top decorations, family activities, and her favorite part: Father Sinsmas himself.
    And she ropes the entire hotel into celebrating… especially her dad.

    But reviving the season comes with an unexpected side effect. Lucifer and Alastor keep getting thrown together. A lot.

    From shared kitchen disasters to cursed mistletoe incidents, hellish competitive nights, suspiciously sentimental gifts, a holiday dance, and one very ill-timed karaoke duet, the two demons find themselves circling something neither is prepared to name.

    Charlie notices. Angel definitely notices. Everyone notices… except Lucifer and Alastor themselves.

    A cozy, comedic, canon-divergent Sinsmas romance featuring a found family, holiday chaos, mutual pining, soft moments neither of them meant to have, and a Sinsmas Eve that changes everything.

    Series
    Language:
    English
    Words:
    13,922
    Chapters:
    4/?
    Comments:
    26
    Kudos:
    89
    Bookmarks:
    21
    Hits:
    1,174

  8. 3

    Sinsmas- Millie's News by

    Fandoms: Helluva Boss (Web Series)  

    04 Dec 2025

    Tags
    Summary

    What happened after the Sinsmas episode??? Welp!! Here is my little take on it! A quick, cute, fluff, oneshot !

    Language:
    English
    Words:
    1,219
    Chapters:
    1/1
    Kudos:
    17
    Bookmarks:
    3
    Hits:
    186

  9. *

    Heavenly Choir (+ Encore) by

    Fandom: Hazbin Hotel (Cartoon), Helluva Boss (Web Series)

    15 Feb 2025

    Words:
    38,428
    Works:
    3
    Bookmarks:
    198

  10. 52

    One Big Happy Family(?) by

    Fandoms: Hazbin Hotel (Cartoon), Helluva Boss (Web Series)  

    10 May 2024

    Tags
    Summary

    They fight a lot. They argue and insult each other all the time. Their meetings never actually get anything done. But they do care about each other, even if they will never admit to it. Ever. The Sins are just one large dysfunctional family. Honestly, it's a surprise they haven't actually killed each other yet.

    There's one thing though, only they can insult each other. Hurt one of them, you'll have 6 others after you. And don't even DARE think to hurt their precious niece, Charlie.

    Language:
    English
    Words:
    6,272
    Chapters:
    4/?
    Comments:
    49
    Kudos:
    210
    Bookmarks:
    52
    Hits:
    5,203

  11. 14

    I Wonder Why I Didn’t See it There Before? by

    Fandoms: Hazbin Hotel (Cartoon)  

    01 Dec 2025

    Tags
    Summary

    It’s the season of Sinsmas and Lucifer is sure Alastor is planning on giving him hell by bonding with his daughter in front of him. Boy, is he wrong.

    Language:
    English
    Words:
    2,537
    Chapters:
    1/?
    Comments:
    1
    Kudos:
    65
    Bookmarks:
    14
    Hits:
    550

  12. 2

    Christmas (Sinsmas) Chaos by

    Fandoms: Hazbin Hotel (Cartoon)  

    04 Dec 2025

    Tags
    Summary

    Chaos, cookies, and twinkling lights. A messy, magical Sinsmas at the Hazbin Hotel with everyone!

    Language:
    English
    Words:
    1,961
    Chapters:
    1/?
    Kudos:
    8
    Bookmarks:
    2
    Hits:
    136

  13. 20

    A sinful Christmas present by

    Fandoms: Hazbin Hotel (Cartoon)  

    25 Dec 2024

    Tags
    Summary

    Vaggie disappeared to make do of a bet she lost while others open their presents. Charlie wanders off to find her, but not how she expected.

    Or

    Vaggie is a present

    Language:
    English
    Words:
    2,482
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    114
    Bookmarks:
    20
    Hits:
    1,974

  14. 33

    Sinsmas: Secret Santa by

    Fandoms: Hazbin Hotel (Web Series)  

    26 Nov 2023

    Tags
    Summary

    In order to get everyone to bond as co-workers and potential new friends, Charlie decides to host a secret Santa event for everyone at the hotel.

    Language:
    English
    Words:
    3,176
    Chapters:
    1/1
    Comments:
    12
    Kudos:
    228
    Bookmarks:
    33
    Hits:
    1,751

  15. 39

    Human Lovers AU by

    Fandom: Hazbin Hotel (Cartoon), Hazbin Hotel (Web Series), Helluva Boss (Web Series)

    24 Dec 2024

    Words:
    29,599
    Works:
    8
    Bookmarks:
    39

  16. 20

    Sinsmas: Holiday with the Morningstars by

    Fandoms: Hazbin Hotel (Web Series), Helluva Boss (Web Series)  

    31 Dec 2023

    Tags
    Summary

    Charlie's been feeling nervous about getting ready for the holidays, especially with the Sins coming over. Now that she's old enough to actually spend time with them, she's unsure if she is ready to meet the rest of her father's friends.

    Series
    Language:
    English
    Words:
    8,757
    Chapters:
    4/4
    Comments:
    78
    Kudos:
    164
    Bookmarks:
    20
    Hits:
    4,874

  17. 1

    Sinsmas Song by

    Fandoms: Hazbin Hotel (Cartoon)  

    02 Dec 2025

    Tags
    Summary

    Tis the Sinsmas season and of course the songs get stuck in your head. Lucifer was an unwilling victim of one such song and sadly he had a meeting he had to attend to.

    Series
    Language:
    English
    Words:
    370
    Chapters:
    1/1
    Comments:
    2
    Kudos:
    22
    Bookmarks:
    1
    Hits:
    197

  18. 2

    Sinsmas Shenanigins by

    Fandom: Hazbin Hotel (Cartoon)

    04 Dec 2025

    Words:
    13,922
    Works:
    1
    Bookmarks:
    2

  19. 13

    Octavia's Ascend by

    Fandom: Helluva Boss (Web Series)

    06 Dec 2025

    Summary

    Octavia gives in and listens to the voice whispering to her from the dark, but will she come to regret it?
    Is the voice helping her as she claims, or is it a trap?
    Will she come to regret the choices she made out of love?

    Words:
    116,165
    Works:
    5
    Bookmarks:
    13

  20. 17

    Three's Company by

    Fandom: Helluva Boss (Web Series)

    29 Jan 2025

    Summary

    You didn't fall in love. Love scared you, so you stayed far away from it due to your very broken past.
    And yet, despite yourself, you start falling in love with not one, but two people: Asmodeus and his boyfriend Fizzarolli.

    Words:
    20,049
    Works:
    11
    Bookmarks:
    17

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