1 - 20 of 3,290 Works in Crossdressing Kink
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Summary
This is an archive of a quest I ran on /trash/ sometimes. All art made for the quest is from anons in the thread.
I now run the quest here. Suggestions for the next chapter can be made in the comments.
Updates are currently to be released almost every Wednesday.Tags contain the kinks of the main cast, since they are the most likely to show up recurrently. Individual chapters may contain other content. Rape and non-con elements are not a central theme, but may occur or be witnessed at the hands of antagonists.
Series
- Part 1 of Quest Archives
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Summary
Тихий шелест одежды вперемешку с безудержным дыханием разбавлял тишину комнаты. Шуршание атласного платья, облегающего подтянутую фигуру, непрерывно звучало при соприкосновении с холодными подушечками пальцев. Изумлённый владелец руки не смел позволить себе большего. Ему хотелось поскорее завершить трепетные поглаживания, совсем не свойственные зарождающимся в голове мыслям; глодало желание поскорее обхватить мужское тело, со всей силы прижимая к себе, потереться об него, вызывая сладострастные звуки, ощупать целиком, разглаживая собирающиеся складки ткани, провести руками по грациозным изгибам.
Чужое лицо было гладко выбрито, но насыщено изобилием ярких оттенков косметики, среди которых беспроигрышно в тон к платью выделялся красный. Подчёркнутые жидкой подводкой глаза, наблюдавшие за завороженными действиями напротив, игриво сверкнули, ещё больше разжигая потаённый огонь, а алые губы тотчас изогнулись в озорной улыбке.
— Ну что, Мэттью, поиграем?
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The Only Girl I'll Ever Love Is John In Drag by n3lli3l
Fandoms: The Beatles (Band), Midsummer Night's Dream - Shakespeare
08 Oct 2025
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Against established stereotypes in the band, John gets the role of Thisbe in the Beatles' spoof performance of Midsummer's Night Dream. In turn, Paul has to face unexpected attraction towards John in drag.
Inspired by the song Andrew In Drag by The Magnetic Fields
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Kinktober-Swapping/Sharing Clothes by thatguywiththefaceOG
Fandoms: Steven Universe (Cartoon)
07 Oct 2025
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Steven and Connie swap outfits for their date night
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A Russian underground fighter, Valetin Abramovich is a stone-faced, claws-gripped on tight kind of lover, who has more blood on his hands externally than internal, meets his organisation's biggest share holder and accidentally grips his claws in tight.
Brynn Davenport is a obsess-now-and-love-later kinda guy who takes it upon himself to learn everything about his new infatuation.
He unveils secrets that should have never left the dark.They have their own thing going on, they don't need labels
Series
- Part 3 of The Mr. Davenport Series
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the average & irresistible mita-san by somethingsecret
Fandoms: プロジェクトセカイ カラフルステージ！| Project SEKAI COLORFUL STAGE! (Video Game)
06 Oct 2025
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i have turned koutaro mita into a bisexual harem protagonist go get him guys
[originally called "cishet-kun's adventures as a gay slut" but then girls got added]
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Weary deeds of the flesh by byany_other_name for venndaai
Fandoms: Lymond Chronicles - Dorothy Dunnett
06 Oct 2025
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Summary
Carefully, Lymond drew away from his grip and stood up. “My lord… I receive your gifts, because you take pleasure in giving, but I do not serve you for possessions. I serve you for friendship… and until that day comes when I cannot defeat you at chess, and you will no longer ask me to play with you.”
Ivan Vasilievich laughed again, a long, ringing shout that echoed across the close room. He leaned forward and gripped Lymond’s arms at her sides with all the force of his powerful hands, and dragged her toward him. “You will not leave me,” he said.
“No,” Lymond replied. His hand moved from her arm and slid, inexorably, towards her sternum, fingertips pushing beneath the wet fabric which clung to her skin.
“And if I tell you to serve me as a woman should a man…”
“Then I will endeavor to learn as you wish me to.”
One of Lymond's meetings for chess with Ivan goes sideways.
Set in my genderbent AU; a sequel to Designed for her pleasure, which isn't necessary to read for this fic but will help in understanding it.
Series
- Language:
- English
- Words:
- 4,276
- Chapters:
- 1/1
- Kudos:
- 2
- Hits:
- 6
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You and your close friend Umkei leave the Butterfly Mansion after being out of commission for three months, you're sent off to kill a group of demons - but little do you know that another threat lies close...
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Till reluctantly allows the cheerleading team to shove him into one of their spare uniforms and give him a makeover in exchange for them not telling Ivan about Till's giant crush on him. But when Ivan finds him, he's very interested in Till's new look, and Till realizes he might actually be interested in crossdressing.
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Modern AU:
The Hidden world is one of the most elusive and exclusive club ever to be invited to, drinks, sex, booze, drugs, and all types of debauchery appear within its walls. Many failed attempts to shut it down by both the Police and the FBI, but whenever they raid the building, the entire thing is abandoned, nothing inside, as if it were left desolate for years.
Hiccup Horrendus Haddock the 3rd is the son of the Mayor of Berk, Stoick, who has taken up the Mission of ridding his town of the club. Hiccup sometimes gets caught in his father's Ire, or blatantly ignored. One day, his cousin Snotlout somehow got invited to the club, and seeing it as a way to win his uncle's favor, he tells Stoick of its location, right after dragging Hiccup into the Bar to get some Blackmail photos of his cousin. What neither realized was that this trip to the club would be the Last time either of them would see one another for a long, long time. -
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Buck tries out a new style, Eddie is in love with it. They fuck about it and confess in public..!
Kinktober day 2 Buck/Eddie - Coming Untouched
Series
- Part 2 of Kinktober 2025!!
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“Mr Molloy,” Armand addresses him, setting down a small bag on the bedside table and opening it. “You made this appointment to discuss your… sexual difficulties, is that right?”
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My First Kinktober (2025) by BobandFred15
Fandoms: モブサイコ100 | Mob Psycho 100, ジョジョの奇妙な冒険 | JoJo no Kimyou na Bouken | JoJo's Bizarre Adventure, 僕のヒーローアカデミア | Boku no Hero Academia | My Hero Academia (Anime & Manga), Dandy's World (Roblox), Ouran High School Host Club - All Media Types
04 Oct 2025
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Characters included:
Reigen Arataka
Serizawa Katsuya
R.E.O Speedwagon
Bakugou Katsuki
Uraraka Ochako
Denki Kaminari
Hanazawa Teruki
Tome Kurata
Jonathan Joestar
Dio Brando
Vee
Sprout
Tamaki Suoh
Dimple (Mob Psycho 100) -
can't hold back (not in the slightest) by cuetheviolins
Fandoms: SHINee, 방탄소년단 | Bangtan Boys | BTS
04 Oct 2025
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"You look really good in this, hyung," Jimin says softly.
Taemin hums in the back of his throat. "Thank you. I hoped you would like it." There's a moment of hesitation before he adds, "Could you call me noona?"
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The Alpha's Obsession by Spookypetrine
Fandoms: My Chemical Romance, Avenged Sevenfold (Band)
04 Oct 2025
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Gerard is a 26-year-old omega who spends more time in mafia romance novels than in real life. He dreams of dangerous men, brutal love, and the kind of possessive alpha who would burn the world down just to keep him. One night, a trip to a notorious Jersey nightclub—owned by the Iero crime family—turns fantasy into reality.
Frank Iero, the mafia prince with blood on his hands and a reputation as terrifying as his father’s, takes one look at Gerard and decides he’s his. What begins as a chance encounter spirals into obsession, possession, and a love story as dark as it is inevitable.
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King in Floral Pink by qyvisitor
Fandoms: 异人之下 | I Am Nobody (TV 2023), 一人之下 The Outcast | Hitori no Shita: The Outcast (Anime), 一人之下 - 动漫堂 | The OutCast - Dongmantang (Webcomic)
04 Oct 2025
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Zhuge Qing stepped once closer as he started rummaging into his pants to find his wallet which held all his black cards and spare cash that he usually gave away as tips to the show girls after each session.
Wang Ye laughed in disbelief at what the other was doing before reaching an arm over to stop the other,
"Haven't you already paid for me anyway… we still have," He glanced at the wall to the analog clock that hung loosely on the wall, "Hm about 50 minutes?"
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My TCC NSFW(porn, suggestive, guro, gore) artwork. by EthanHugs (JerJerSignal)
Fandoms: 20th Century CE RPF, 21st Century CE RPF
04 Oct 2025
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do not interact if your born 2011 or later.
[perps I've done: Arthur Achleitner, Artem Iskhakov, Robbie Hawkins, Adam Lanza, Seung-Hui Cho, Eric Harris]
Series
- Part 1 of My art!
- Part 1 of Guro? So like teacher!.....right?
- Part 2 of I have a fucking piss kink. I fucking love piss.
- Part 2 of Crying makes me feel better.
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Jayce always told Viktor that it was important that people *saw* them. Rich people don't care about ideas, they wanted what looks best.
Viktor finally agrees to come to a gala, Jayce is so happy!Jayce underestimated Viktor. Because Viktor knew sex sells. Jayce couldn't keep himself in check.
Series
- Part 2 of Smutober 2025
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frappel0ver13 and sekurit’s 2025 Kinktober by frappel0ver13, sekurit
Fandoms: 僕のヒーローアカデミア | Boku no Hero Academia | My Hero Academia (Anime & Manga), 呪術廻戦 | Jujutsu Kaisen (Manga), 呪術廻戦 | Jujutsu Kaisen (Anime), Death Note (Anime & Manga), Shingeki no Kyojin | Attack on Titan, Real Person Fiction, Political RPF - US 21st c.
03 Oct 2025
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Hello everyone, and welcome to frappel0ver13 and sekurit’s conjoined 2025 Kinktober: a collection of oneshot fanfictions and drabbles written by us in the last couple of months, each one featuring a different kink. These fics will mostly be written by me, frappel0ver13, although sekurit will be writing some days.
Each week will be a different fandom, and you will be able to recommend ships or kinks so long as there are blank spots on the list. The list is in the first chapter.
Thank you, and let’s have a great Kinktober 2025!!
-frappel0ver13 and sekurit
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He’s used to watching from a distance, but actually being in the distance is more nerve-racking than he initially thought.
Oh, little Akira, you got in way over your head - tut, tut.
Stealing the good stuff from Kashiwagi’s office had been easy; he keeps all the good stuff in his bottom drawers in the hopes the littles will find them and want to play dress-up. On second thought, maybe coming into Kazama's office with a black lace bra and a pair of crotchless panties had been a tad bit too precocious.