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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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In a feminist future, a bashful novice in silk tunic must yield to a poised mentor's first pegging, proving his surrender for total release.
by
✨
nero88
4.0
243
0
2
12
Teased Streamer's Surrender
By slinkymike88
RedQuill
A shy femboy crossdresses and does more and more depraved things on stream as the donations from his chat pile on. The femboy is forced to wear a chastity device and is ordered to swallow his own cum as part of a mandate. The femboy is then met by a mysterious man who is a keyholder to the chastity device and is forced to perform sexual acts on him. The femboy is trained and inspected by the keyholder and is forced to swallow the keyholder's cum as part of a mandate.
by
💋
slinkymike88
5.0
234
1
2
3
Hot roommate Sasha catches me dressing up in her underwear, and uses the opportunity to turn me into her sissy OF cash cow
by
🌙
snowy_slave
5.0
230
0
0
17
A sissy college student transforms into a hyper-feminine girl in a pink ruffled bikini, then locks herself out of her apartment for a daring nighttime walk of shame through the complex.
by
💦
chelseasubslut
3.5
228
0
1
11
A shy intern's accidental coffee spill traps him in a locked conference room with his stern mentor, who renames him Mei and transforms the humbled Asian sissy into a kneeling, popper-fueled deep throat worshipper.
by
throwtosavestuff
4.0
218
0
2
73
Teased Streamer's Surrender
By seqqqq1
RedQuill
A shy femboy crossdresses and does more and more depraved things on stream as the donations from his chat pile on. The femboy is forced to wear a chastity device and is ordered to swallow his own cum as part of a mandate. The femboy is then met by a mysterious man who is a keyholder to the chastity device and is forced to perform sexual acts on him. The femboy is trained and inspected by the keyholder and is forced to swallow the keyholder's cum as part of a mandate.
by
🍷
seqqqq1
217
0
1
2
It's a quiet Saturday night in the coed dorms, and Stephen is invited by some of the girls and one other guy to join then in there room for a few drinks, and they think it would be fun to play card game of strip poker. He should of knew something was off, because it was the girls suggesting that, and it normally you wouldn't hear an idea like that from college girls. It doesn't take long to realize Stephen and the other guy are just no match for the girls, and are reduced to no clothes at all....
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🫦
ellen0866
215
0
0
85
A man wakes disoriented in a stranger's body, mastering her makeup and lingerie before realizing the gorgeous reflection staring back is his K-pop idol Jennie.
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patch72
213
0
1
25
Dressed as her cousin for a night out, a nervous man lets his friend do his makeup—then a stranger’s intense gaze turns their innocent game into a slow, blurring seduction.
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daram
212
0
2
14
A crossdresser named Tess, dressed in a revealing red bodycon dress and sexy lingerie, visits a truck stop in search of adventure. She encounters Bryan, a muscular truck driver, and the two engage in a passionate encounter involving intense oral sex, anal penetration, and multiple orgasms. The narrative explores themes of crossdressing, truck stop encounters, and the dynamics of power and pleasure between a crossdresser and a rugged truck driver.
by
🌙
serenelove
5.0
206
0
1
1
Follow Leo on his journey to find his true self.
by
👀
pretend3r
201
0
0
35
A man reveals his secret crossdressing identity to his new girlfriend over a romantic dinner, leading her to request a transformation that ignites a new chapter of intimacy, acceptance, and kinky exploration.
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rachelmtg
5.0
198
0
0
13
His stepmother, a dominatrix, replaces his unemployment with maid training—sissification, rules, and submission that slowly becomes the only life he wants.
by
🍑
veronica_13
5.0
196
0
1
4
Karen, a male crossdresser, undergoes a full makeover at his favorite beauty salon, including a full body wax, makeup, and wig application. He then dresses in a sexy, short bodycon dress and goes to a gay sauna, servicing as many guys as he can at a gloryhole, all while his own hard cock strains in his silk panties under his tight dress.
After Karen's full makeover, he goes to the gay sauna Arrows at Rydalmere, where he services multiple men at a gloryhole, all while his own hard cock strains i...
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karencorset
192
1
0
5
¡The Crossdresser Rimuru!
By naounable
RedQuill
Rimuru, and androgynous boy try Crossdress! But he sometimes get's caught, anyway he tries to don't get caught too easily, but when he is aroused he does not think about consecuences.
by
🔥
naounable
184
0
1
5
A straight guy's secret kink leads him to make his gay roommate wear a girly outfit after losing a bet, igniting an erotic game of control and desire.
by
🍒
bottomofthewell
4.7
181
0
0
17
Stepdad Catches Femboy Streaming
By lickerboy
RedQuill
A femboy's secret page is exposed by his stepdad, who forces him into a gangbang, awakening a hidden, addictive hunger.
by
💜
lickerboy
4.0
173
0
1
18
A shy, feminine teen makes a risky bet with his muscular best friend: a five-round gaming contest where each loss means shedding another layer of his masculinity.
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roguedman
172
0
1
9
Black jock discovers white sissy cam boy's secret, becomes his daddy for their viral interracial sissy channel.
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roguedman
5.0
171
0
0
21
A man with feminine features is mistaken for a bride at a billionaire's selection ball and is transformed into a glamorous bride by his ex-girlfriend and her friend. The transformation includes elaborate clothing, breast forms, and high heels, leading to a mix of humiliation and arousal as he is prepared to be presented to the billionaire. The women's intimate touches and the sensation of the elaborate attire heighten his arousal, leading to a complex exploration of gender roles and sexual dynam...
by
🔥
stellatron38
166
0
0
9
A 24-year-old engineer on a India work trip is taken in hand by older women who dress him in feminine attire, reshaping him daily.
by
allie69x
3.0
163
0
1
5
![[MTF] The Weight of Expectations](/_next/image?url=https%3A%2F%2Fredquill-image.nyc3.cdn.digitaloceanspaces.com%2Fstoryimages%2Fbe7560ae-9db7-4b95-b4fa-a9e390c800f9.jpg&w=3840&q=75)
A software engineer invented a wife to stop his parents' pressure; his gay best friend transforms into her, blurring every line.
by
💋
purduerm
162
0
0
7
A young man's hyperspermia condition forces his young stepmother to milk him daily, discovering his softness fetish—she uses it to dominate and feminize him into her plush-loving submissive stepdaughter.
by
🍒
softnessfetishtales
5.0
159
0
0
1
After a single glance, she sends him to the bedroom where women's clothes are laid out. He sheds his male identity, dons her frilled panties, bra, and skirt. She inspects his transformation with hungry hands, then takes control.
by
✨
writervpa
5.0
159
0
1
1
A timid vegan guy with a humiliating past meets a stunning bombshell craving sensitivity, sparking an unlikely romance.
by
💫
abdlashley
5.0
155
0
1
16
A husband accepts a bet: wear a mini skirt for a month without flashing his boxers. If he fails, his wife will feminize him daily.
by
💋
nishacd
149
0
1
6
Frat Party Slut Used by Everyone
By jullius
RedQuill
A shy boy’s secret kink becomes his public shame when frat guys use him for a brutal, all-night gang-bang.
by
🍑
jullius
144
0
1
3
At a dead frat party, six seniors goad the slimmest brother into becoming their entertainment, then a mysterious girl transforms him from boy to beauty in a back room.
by
daram
140
0
2
20
At a wild frat party, a slim pledge is feminized by the chapter president and ordered to make three brothers cum to earn his place.
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lopbunny
140
0
0
12
Ross, a crossdresser, checks into a luxury hotel and decides to go out in public in a dress and makeup. He gets locked out of his room and is helped by a hotel manager who takes advantage of the situation and has unprotected anal sex with him. Ross enjoys the experience and invites the manager back to his room later that night and things go gonzo from there...
by
🫦
sonnycrockett
137
0
0
14
Ron is working with reputed company his short and fair, also very rude and joking on women clothes and body. His worked some women coworker, some women are very depressing and tried regular jokes on skirts and dresses as well as sexually harassment. After many complaints with HR and despite warning his behaviour not improve. They have no proof to show HR he is very bad person and treat women bad. One day one girl thinking finding something internet force feminization and sissification. She decid...
by
💋
nishacd
4.0
136
0
1
8
Michael, feeling the weight of his daily life, seeks a night of liberation through a complete male to female transformation at the House of Transformation.
Under the skilled hands of Arpi, Michael becomes Karen, a confident and alluring woman, complete with waxing, makeup, wig, lingerie, a sexy bodycon dress, and 4-inch heels.
Karen heads out to a local bar, where she catches the attention of two gentlemen, Joe and Rick, who offer to buy her a drink.
The night unfolds with Karen navigating th...
by
🔥
karencorset
5.0
136
0
0
11
A shy college boy shaves his chest, slicks on lipstick, and steps into a borrowed skirt for the first time, daring a frat party to discover the girl he’s becoming.
by
daram
129
0
0
8
A nervous crossdresser reveals his bikini to three friends at a private pool, sparking an intensely charged encounter.
by
🍑
goneyy3
128
0
1
10
A CEO discovers a hidden desire after his wife leaves him and he rummages through the clothes and lingerie she left behind. He goes on a journey of self discovery.
by
🌶️
angelsky
128
0
0
13
Becoming Clara
By justme2102
RedQuill
Becoming Clara follows the emotional and physical transformation of a trans woman struggling to shed the deeply ingrained, masculine habits of her past identity, Thomas. While she has begun crossdressing in secret, she finds herself trapped by years of muscle memory—her stride is too heavy and her posture too rigid, causing intense frustration. Seeking a fresh slate, Clara takes a monumental step forward by starting Hormone Replacement Therapy (HRT). However, because her anatomy remains a major ...
by
justme2102
5.0
125
0
0
10
Cam Boy Sam's Wet and Messy Dive Into Love (WIP)
By dlman90210
RedQuill
A 20 year old bisexual college student, Sam, has a secret life as a femboy cam performer, who makes money by masturbating on a cam site, and has a fetish for scat, piss, and diapers. His life turns upside down when he meets Alex, a charming, soft gentleman who appreciates Sam's proclivities.
by
😈
dlman90210
125
1
0
14
Two best friends transform Lee into their feminine doll before a frat party, hiding a secret beneath their sundress.
by
wolfox
5.0
124
0
0
10
A closeted teen lands a girl's role in the school play, starting a secret affair with the lead actor backstage.
by
daram
5.0
123
0
0
13
On his 19th birthday, a shy college student confesses a secret desire to his sister. She dresses him in lace and heels and Traci is born
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sonnycrockett
121
0
0
11
Luna's way into porno. Олег приезжает в отпуск из Канады в Москву и встречается с 18-летним кроссом. Кто бы мог подумать, чем все это дальше обернулось...
by
tesla_1998
116
0
1
36
Two straight roommates' bet goes sideways when the loser must wear a dress, do housework, and play girlfriend—until giving a handjob changes everything.
by
🔥
mikeg
115
0
3
4
After marrying a wealthy widow, a man submits to nightly cream rituals and teasing from her daughters, unaware the real trap is tightening around him.
by
🖤
lyttaren
5.0
110
0
0
11
Cuckolding Roommate Roulette
By yuanbl
RedQuill
After his girlfriend becomes student council president, a college guy's drunken roommate party leads to secret balcony sex with his buddy's dance-major girlfriend.
by
💫
yuanbl
109
0
7
1
Crossdresser Sarah has one hour to shed her male disguise before two weeks as her true self at a kinky adult-only resort with best friend Fiona.
by
sarah_maddison
108
0
0
86
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.
by
ellen0866
107
0
1
54
Marion Takes his Ass
By anonydd
RedQuill
A young man drops off a package for his mother and is pulled into a tour by a commanding neighbor, who makes him change into hidden panties and dance before revealing his massive cock.
by
🍒
anonydd
5.0
105
0
0
6
From Chat Seduction to Strap-On Ecstasy
By reeve
RedQuill
Reeve, a young man grappling with his gender identity and sexual preferences, finds himself drawn to the idea of experiencing sexual pleasure as a woman. He confides in his long-time friend Amber, who decides to help him explore this desire by taking on the role of a dominant partner, using a strap-on to fulfill Reeve's fantasy of being penetrated and dominated.
Amber guides Reeve through a series of intimate and explicit acts, from sensual kissing to oral stimulation, ultimately leading to the...
by
🔥
reeve
105
1
0
2
RedQuill