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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 (346)
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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
by
🌙
maninnylons
71
0
0
10
A widowed B&B owner hires a shy young man whose secret lace panties spark an unexpected connection.
by
aerojay72
5.0
70
0
1
5
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...
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💜
naima
70
0
0
6
A guy accepts a pool invite on a scorching day, but his friends surprise him with a women's string bikini as his only swimwear option.
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mikeg
69
0
0
4
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.
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sofiarossi
69
0
3
3
A thief fleeing the mob plummets between two high-rises, a wild series of cartoony accidents transforming him into a stunning blonde in white before landing in a mobster's arms.
by
💜
burneraccunt
67
0
1
2
Femboy Gets Worshipped by His Succubus Girlfriend
By futanarisekai
RedQuill
A femboy student returns from class to find his lingerie-model girlfriend waiting in the doorway—but she's a succubus who craves his worship, not his corruption.
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futanarisekai
67
0
0
5
A secret crossdressing college fan gets his poster signed by the Dallas Cowboy Cheerleaders, then wakes up in their locker room—as one of them.
by
ellen0866
5.0
67
0
0
33
Wife Catches Me in Her Dress
By steamylingerielover
RedQuill
Caught crossdressing in his wife's white evening gown, a husband is humiliated in the pool by her and her friends, then pegged in front of watching neighbors.
by
😈
steamylingerielover
3.7
66
0
0
6
A gay man takes makes a play for his straight best friend by wearing his ex-girlfriend's dress, and soon all their fantasies are laid bare.
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🍒
jrichard99
66
0
0
20
Closeted husband's secret fuck machine
By lopbunny
RedQuill
When his girlfriend leaves town, John secretly transforms into Becky, dons lingerie, and uses a new fuck machine to live out a solo spitroasting fantasy.
by
lopbunny
4.0
66
0
0
6
A swimmer’s routine is upended when a pink supplement trial stops his leg hair but regrows the top hair. The psych component makes him think all is normal
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mastacheata
65
0
0
13
A curious boyfriend, Chris, is caught in a compromising situation trying on his girlfriend Heather's panties. Heather, seizing the opportunity, forces Chris to wear a lace bra and panties to a family dinner, where she teases him relentlessly and ultimately exposes his secret to his parents in a shocking and humiliating display.
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💜
the_barber
65
0
0
16
Roughneck Gets Dressed Pretty in Losing Bet
By fraterbabs
RedQuill
A cruel dock worker bets his long-haired blond friend, a proud petty criminal, to dress in lingerie and heels after a lost football game, sparking a volatile battle for dominance.
by
✨
fraterbabs
63
0
1
2
Boss Transforms Intern into Sissy Top
By adez
RedQuill
A boss transforms his intern into a sissy top, sending him to a sex-positive stylist who renames him Chloe, dresses him in lace, and reveals Marcus prefers flat chests.
by
😈
adez
61
0
0
19
I’m writing a story about Ryouma, a male prostitution (gay), stripper, he has slender body and medium mulberry hair (shoulder), he like to crossdress. worklife scene, a character experiences from when he change into his erotic outfit (work unifrom usualy with fish net stocking, shorts that exposed too much leg (maybe just covering the asshole and crotch area), and a crop top that exposed his chest, thight fit body. ryouma personality on the club floor is entertaining and seductive, he's some ki...
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💦
akirahsn
5.0
60
0
2
15
Crossdressed Huey, Dewey and Louie gets pegged by the girls in a locked restroom stall while others fingers themselves and collects the cum-filled condoms.
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💜
thunderhead28
5.0
59
0
0
7
Femboy Incubus Fucks a Bimbo
By futanarisekai
RedQuill
A femboy incubus in a crop top catches a bimbo influencer's eye at the gym, leading to a shower stall hookup that matches their filthy, coordinated energy.
by
futanarisekai
4.0
59
0
0
2
Sorority Initiation: Sissy Slut
By dinomite7
RedQuill
A shy college guy becomes the sorority's entertainment, transformed into a sissy and subjected to humiliating anal games.
by
🍑
dinomite7
58
0
1
3
A bride poses as the hired escort to infiltrate her fiancé’s wild stag party, but they see her as a whore to use.
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💋
enjanss
58
0
2
2
A married businessman wears the lingerie and collar his wife packed, following her command to find a dominant stranger at a gay bar.
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polite_panda_
57
0
0
9
A stepson yields to years of subtle encouragement when his stepmother leaves a sheer lace bodysuit on her bed before stepping out.
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🍑
goneyy3
57
0
0
3
![[MTF] My Sketches Into Cosplay World](/_next/image?url=https%3A%2F%2Fredquill-image.nyc3.cdn.digitaloceanspaces.com%2Fstoryimages%2Ff16e1fbe-7cb4-4712-8eb5-2061b3b406db.jpg&w=3840&q=75)
Max Turner arrives at Metro Comic Con expecting another exhausting but lonely weekend hidden behind his small artist booth near the back of the convention hall. At twenty-seven, Max is talented enough to attract regular customers for his fantasy illustrations, yet painfully shy whenever conversations become personal. While the convention buzzes with loud music, flashing camera lights, and confident cosplayers posing dramatically for crowds, Max keeps himself buried behind sketchbooks and pri...
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purduerm
5.0
57
0
1
7
A lonely male prison guard is seduced by a trans inmate, then submits to her will—becoming her secret lover and, eventually, her pimped-out toy for the entire cell block.
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mikeg
56
0
0
3
A straight frat pledge loses a bet and is forced to wear a bodycon dress to a party, where his fraternity president watches as guys grind on him before pulling him upstairs for blow jobs and sex.
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🔥
mikeg
5.0
56
0
2
1
Caught in her lingerie, a brother becomes his sister's dark substitute for her boyfriend's anal cravings.
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bear_btm_sub
55
0
0
7
A humiliated Hindu husband's three-inch failure drives his wife to fantasize about her tall Muslim neighbor while punishing her submissive spouse in their bedroom.
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adhu31
5.0
52
0
2
11
Husband wear wife saree to superise on aniversary for fun and role reversal. Wife come to home but supersingly her friend also come today night. Both girls shocked and laugh, husband run away bedroom Change in make dress. Wife told why you changed my friend aware u like wearing saree and my clothes, even her husband wearing dresses. Go and wear good saree wear celebrate aniversary. Friend husband also come friend told his husband go take her wear you good saree. They both wearing jeans —the wive...
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nishacd
51
0
2
10
A housewife confesses her fantasy of another man to her husband—who reveals he’s a bisexual cross-dresser.
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urmila
5.0
49
0
0
3
A young man poses as his mother to save his sister from foster care, but the disguise leads to an unexpected date with his former principal
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😈
basiltothethird
48
0
0
9
Stranded in a monsoon, a man's pack and dignity are lost. His girlfriend laughs, strips off her soaked clothes, and hands him a bra and denim jumpsuit for the trek ahead.
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nishacd
48
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0
8
A dominant wife discovers her unemployed husband secretly dressed in a frilly maid outfit, leading to a possessive, electric confrontation.
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dilandau
47
0
0
1
Sissy Femboy Seduced by Cougar
By kittylove
RedQuill
A shy closet sissy browsing lingerie gets caught by a dominant Mommy shemale who bullies him into accepting his feminine side with brutal, primal submission.
by
💫
kittylove
46
0
0
1
His wife planted the hidden lingerie to trap him. She demands he model each piece, servicing her between changes, then reveals she wants to breed him while he's dressed up.
by
justin007
45
0
2
5
A 1986 job interview spirals when a CEO demands male candidates dress as women; one desperate applicant endures the process for a chance at the job.
by
🫦
sofiarossi
45
0
2
1
Kneeling before the sun princess, you confess your desire to serve her intimately. She claims you as her pet on the throne room floor.
by
😈
sashastripes
45
0
0
23
In 1916 Tbilisi, a hardened Bolshevik is stunned when a beautiful woman greets him at the safehouse—but she's actually his old schoolmate Alexi in disguise
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vixien
45
0
0
6
A shy man in a gender-flip auction is won by his best friend, leading to a passionate night of revelation and desire and possibly a future of opportunities
by
cdamandabeth
5.0
44
0
0
6
Света идет в салон красоты. И почти случайно соблазняет там мастера по маникюру.
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tesla_1998
44
0
0
5
When Derk's girlfriend dumps him, he blackmails flatmate Harry into a crossdressing makeover to pose as fake girlfriend Teena, sparking chaotic consequences.
by
💋
nishacd
43
0
0
9
Wife Transforms Husband Into Sultry Doll
By naughtytodd
RedQuill
A wife's drunken confession unlocks her husband's secret doll fantasy. Now she controls every detail: his outfits, makeup, when he cums, and the humiliating video evidence sent to her best friend for approval.
by
🍒
naughtytodd
5.0
43
0
0
15
12345678-11
By navi_oliveira_3
RedQuill
Enemies bound by a contract, a billionaire and a restaurateur engage in a brutal game of hate-sex where words cut deeper than touch.
by
🫦
navi_oliveira_3
43
0
1
8
A wife's day off turns risqué when she demands her husband serve as the naked bartender for her two curious friends, wearing only a tiny apron.
by
👀
piggyandbabs
42
0
0
8
Cross-dressing Jake gives Bill a lap dance in a miniskirt and wig, discovering Bill's huge erection. Turned on, he lets Bill's cock slip between his ass cheeks and slowly take it all.
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🔥
mikeg
42
0
1
1
A handsome hippie enlists to sabotage the military, but the induction haircut and seeing other men sheared arouses him
by
✨
chantalsaproblem
5.0
42
0
2
13
A straight man's sister convinces him to dress as her whore for Halloween, then pimps him out at the party.
by
🔥
mikeg
5.0
41
0
2
3
A man in a silk dress stops at a gas station. A stranger notices, asks to feel the fabric, and their curious touch ignites an unexpected, charged encounter.
by
🔥
mikeg
41
0
0
2
Submissive Sissy's First Time with Friend
By ashleyxcd
RedQuill
A crossdressing husband moves in with his gay best friend, then appears in lingerie and heels, shocking him into a long-awaited first encounter.
by
🍷
ashleyxcd
41
0
0
10
RedQuill