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Crossdressing Stories
Read Crossdressing stories. Caught crossdressing stories: a husband in his wife's lingerie drawer when the door opens, a roommate who finds the stockings, a girlfriend who decides she likes him better in a skirt.
Stories (334)
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A guy in a mini skirt, g-string, and wig gives his friend Bill a lap dance in gray sweatpants, then lets Bill's massive cock slip inside his ass until he takes it all.
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🔥
mikeg
3.0
100
0
0
2
Blacked Moving Day
By anonydd
RedQuill
@Massive cum Silas is an 18 year old virgin small pale And hairless with a small cock. He lives with his mom who happens to be out of town and they are getting ready to move so his mother tells him that she sent movers and these are corporate movers. They're gonna go in and pack up the entire house put it on a truck and then move everyone and then Silas will fly out to where his mother is now. The movers are three big black man one muscular one a little bit heavy set and then one truly fat he'...
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🍒
anonydd
4.0
98
0
0
8
A young man surrenders to a forbidden ritual, dressing in his absent mother's lace and silk while grappling with the shame and arousal that have defined his secret life.
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ellen0866
97
0
1
54
Humbled husband Scott loses a bet, so his wife Kim dresses him in a diaper and lavender dress to shop as proof of her superiority.
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sub4ever
96
0
5
3
A shy "girl" experiences mysterious arousal during class, then discovers a hidden erection that forces her to confront her true body.
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👀
sissy_aeryn
95
0
1
12
A male adventurer descends into a cursed dungeon where mysterious gear transforms his body into a girlish form, each equipping step pushing him deeper toward a goddess's erotic trap.
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burneraccunt
5.0
94
0
1
5
A witch's spell backfires, forcing four housemates to physically transform into the clothes they wore, unleashing five nights of erotic chaos.
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arrow6231
94
0
0
12
![[MTF] The Gulf Disguise](/_next/image?url=https%3A%2F%2Fredquill-image.nyc3.cdn.digitaloceanspaces.com%2Fstoryimages%2Fee750521-b9d6-4d1a-9769-bdf631ccc7bb.jpg&w=3840&q=75)
A disgraced consultant flees Gulf authorities disguised as a veiled woman, then discovers his transformation unlocks possessive desire and erotic submissio
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purduerm
93
0
1
2
A domme dresses her sub in lingerie, doses him with MDMA and a plug-ring, then alternates between his pounding her g-spot and her pegging him to orgasms.
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lil_femboy
92
0
0
3
4 men & 1 girl trapped in a haunted haveli. A ghost demands virginity. A priest reveals the only escape: lose it to anyone, even each other.
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desapax605
5.0
86
0
0
1
A lonely divorcee rents a quiet annexe, unaware his silver-haired landlord plans to feminize him one silk-clad step at a time.
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🖤
nylonslave
86
0
0
8
A locked sissy risks everything at an underground strip club audition, where cage checks are mandatory and the manager's expectations go far beyond makeup and heels.
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👀
amanda_vallentine
86
0
0
25
A billionaire makes his assistant wear a maid's uniform for a gala, but the young man's shy obedience and hidden appeal in the short skirt make his stern boss crave more than just service.
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arejay
85
0
1
2
Closet Secrets and Slumber Surrender
By sonnycrockett
RedQuill
Tom is an 18 year old man who is caught peeping on his stepsister's slumber party. She makes him join the party!
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sonnycrockett
84
0
4
4
A wife secretly replaces her husband’s briefs with silk panties, then spends a year using quiet coercion to feminize him, until a stranger hits on him at a bar while she watches.
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😈
meghan4now
3.0
84
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0
39
A closeted trans, guided by an online DaddyDom, risks a swingers club's T-girl afternoon to shed her false marriage and finally become her true self.
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storyjade
5.0
82
0
0
10
Desperate fiancé Robert risks a mysterious modeling shoot for $20K to save his relationship, but the agency's erotic demands test his limits.
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barbieboy2323
82
0
0
15
Three Daddies own me
By anonydd
RedQuill
A terrified virgin in secret lingerie is cornered by three predatory men who drug and restrain him, driving him toward a night of twisted submission.
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🍒
anonydd
5.0
81
0
2
5
A crossdresser cruises a dangerous park after dark, posing as a woman until a john forcibly takes him, using his mouth and then his ass.
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🔥
mikeg
81
0
1
3
A bet on the Super Bowl becomes a contract. Jake loses and must submit to his wife Krystal’s strap-on, her hidden fantasy now unleashed, as she secretly plots his feminization using experimental drugs.
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clitbunny
81
0
0
14
He was invited but didn't know for what... Девушки пригласили на девичник парня. Он думал воспользоваться ситуацией, но воспользовались им. Перевод в конце
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tesla_1998
81
0
0
6
A husband bets his wife he can handle her wardrobe for a day, but her shapewear and heels awaken a hidden, desperate pleasure in being bound and dressed.
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🖤
slate
80
0
0
6
Roommates up the stakes in strip poker
By littlemissexulansis
RedQuill
Five college friends turn strip poker into a high-stakes game where losers either strip bare or don the winner’s lewd pick, with sexual acts on the table.
Husband's Secret Crossdressing Rituals
By ji4490398
RedQuill
A respectable married salesman hides a secret crossdressing life，indulging in forbidden fantasies when home alone.
by
✨
ji4490398
80
0
1
45
A dainty tutor's confession to his cheerleader crush backfires when she confronts him in the locker room, revealing a devastating truth.
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cuck7890
80
0
1
24
Jock to Sissy
By missygurl1
RedQuill
Homophobic jock Jay is blackmailed by girlfriend's sissy best friend Riley.
by
✨
missygurl1
79
0
1
8
A closeted cross-dresser's secret life is discovered by his coworker, leading to a series of intimate conversations and a date that blurs the lines between Michael and his alter ego Karen.
Rick's curiosity and acceptance allow Michael to explore his feminine side openly, culminating in a passionate encounter where Karen's true desires are revealed and fulfilled.
The narrative delves into themes of identity, acceptance, and the erotic tension between a man and his alter ego, with explicit scene...
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karencorset
79
0
0
5
When Kayla's maid of honor tries to seduce her fiancé, she kicks her out—then convinces her old friend Rich to become Rachel and take the bridesmaid's place.
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rachelmtg
78
0
0
10
A disguise artist transforms into his client's college ex-girlfriend with hyper-realistic prosthetics, to fulfill an impossible fantasy.
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💦
buffy_gel
78
0
1
5
An effeminate convict's prison haircut unleashes his brutal masculinity, attracting the desperate affections of effeminate prisoners
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✨
chantalsaproblem
5.0
77
0
3
10
Caught by his buddies, the old joke becomes real: "When did you start wearing pantyhose?" "When my wife found them in my car"
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gradist
77
0
3
1
Рок-группе позарез нужна солистка. А кто ищет, тот всегда найдет. Шоу начинается...
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tesla_1998
76
0
0
8
College student Brad's stepsister can't make her wedding, so he must fill in as the bride wearing her fitted gown.
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sonnycrockett
76
0
0
18
After his father's will leaves Ivan sole heir, his furious stepmother Mrs. Shen plots with her lawyer to legally break the terms that disinherit her.
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nishacd
76
0
1
8
A man, Ben, is captured and bound by a seductive, older woman, Samantha, who has a unique and painful fetish. She subjects him to a full leg waxing and a complete pedicure, culminating in the humiliation of wearing high-heeled shoes.
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sofiarossi
76
0
0
8
A witch's enchanted shapewear transforms Bruce's body in his sleep, plumping his curves into soft feminine fullness.
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💫
arrow6231
75
0
0
17
After a decade of marriage, Donna’s casual curiosity about having a cock sparks Jim to present her with a realistic strap-on, launching a power play that shifts their relationship into uncharted submission.
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polite_panda_
74
0
0
24
Tsubaki Host Club
By amia
RedQuill
Tsubasa was always called a 'Boy' since her childhood but after a fight in her old school, she was sent to a private school but got misgender
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amia
74
0
0
41
A disgraced noblewoman, branded a thief, must survive the brutal hierarchy of a 1786 Paris prison.
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dilandau
5.0
74
0
0
9
A rude customer insults a vintage boutique. The owner and her assistants teach him a lesson by forcing him into the frilliest dress, panties, stockings, and makeup—unlocking a secret submissive desire he can’t resist.
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sofiarossi
73
0
2
1
A man confesses his darkest fantasies to a therapist who weaponizes them, turning his secret need for smoking and feminization into an inescapable addiction she controls.
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alogrette
5.0
73
0
0
9
A high-powered wife returns from closing a mega deal, drugs her husband's scotch for endless orgasms, and spends the weekend using her sissy.
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lil_femboy
72
0
0
3
Crossdressing by night, he cruises a dangerous park as a fake woman—until a real John takes him by force for mouth and ass.
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🔥
mikeg
5.0
71
0
0
4
When her unemployed husband turns lazy, a wealthy wife trades marriage for a contract making him her submissive sissy maid.
by
🖤
slate
70
0
0
12
CEO Wife and Bratty Uke
By zakilla
RedQuill
An omega diplomat's past escapades ignite his alpha CEO wife's possessive jealousy, sparking raw confrontations and erotic reclamation.
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🍑
zakilla
69
0
0
63
A lonely divorcee's secret crossdressing unlocks a bold new identity, leading him to a transformative night at an exclusive club where he embraces his deep
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🌙
maninnylons
69
0
0
10
A Timid Man's Transformation
By naima
RedQuill
In the lively chaos of Bangkok's night market, a reserved Western man named Ethan encounters a captivating Thai ladyboy named Mira who seduces him with her dominant presence and alluring charm.
Ethan's journey begins as a timid exploration of a vibrant, exotic setting and evolves into a profound experience of self-discovery and acceptance.
Mira guides Ethan through his fears, encouraging him to let go of his inhibitions and embrace his desires. Their encounter delves into themes of dominance a...
by
💜
naima
69
0
0
6
In 1987, a desperate job candidate at a ruthless CEO's interview is led to a private office, stripped, feminized into a silk blouse, heels, and makeup, then aroused and serviced before facing his new boss.
by
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sofiarossi
68
0
3
3
RedQuill