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Sissy Stories
Read stories about the liberating journey of embracing femininity and submission through sissy transformation! Sissy play involves men exploring their feminine side through cross-dressing, behavior modification, and often submission to dominant partners.
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Stories (270)
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Popular (All Time)
A husband's perfect life unravels when a bullied classmate returns to convince his bombshell wife he's secretly a sissy.
by
💫
barbieboy2323
255
0
2
9
A submissive sissy is caught riding a dildo in a skirt and cock ring harness by his roommate's girlfriend, who leads him by his small cock to his roommate for a raw, dominating threesome where he is used and humiliated.
by
writer7212
5.0
248
0
4
1
Dressed as his bratty bimbo girlfriend, a guy goes too far with her lip plumper, transforming into her perfect clone with lasting consequences.
by
🖤
basilllllll
5.0
243
0
1
37
Unlocked
By bisissy420666
RedQuill
A crossdressing husband is initiated into a month-long training regimen by his BBW wife, who locks him in delicate lingerie and restrictive chastity, gradually introducing him to an expanding arsenal of toys designed to probe and expand his ass in daily sessions.
The husband's training includes spontaneous, intimate urination rituals and culminates in sessions where he is guided to swallow his own eruptions, building layers of devotion and surrender in their deepening power dynamic.
by
🌶️
bisissy420666
239
1
0
45
Theatrical Submission
By wilddaisy85
RedQuill
A crossdresser meets a couple at a sex theater, where he is feminized and forced to perform sexual acts on the husband and other men. The wife enjoys being pleasured by other sissies and watches as her husband fucks the crossdresser, who is then passed around for anal sex and eventually has a sissygasm.
by
❤️🔥
wilddaisy85
238
0
1
3
Auntie Beatrice, a retired dominatrix, discovers her nephew's hidden sissy desires when she walks in on him changing into pink satin panties in the bathroom.
She takes it upon herself to transform him into her perfect sissy maid, using a combination of strict discipline, humiliation, and erotic punishment.
His training involves a variety of sissy maid duties, including dusting, polishing silver, and vacuuming, with Auntie meticulously correcting his every mistake with her paddle.
As his train...
by
💜
bitchslave1981
233
0
1
13
On his eighteenth birthday, Wavie receives a wardrobe of feminine clothing from his parents, who encourage him to embrace his desire to be a sissy faggot cocksucker.
Wavie's first day of school in his new attire is met with ridicule and humiliation, but also a thrilling sense of liberation.
He meets Brad, a senior linebacker, who initiates him into a world of rough, degrading sex, where Wavie finds his true pleasure in being used as a cocksucker.
by
waviethesissy
231
0
3
1
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
During a crazy frat party henry being the slimmest and least muscular in the house is forced into being the entertainment since the real women would not come. He is forced into the girliest and frilliest outfits for the amusement of the others. forced feminization, realistic crossdressing,@Knotting @Public humiliation punishment @Collar and leash control @Begging for degradation @Cum-stuffed panties
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🌙
trishasissy
230
0
1
19
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
Wavie, a delicate and effeminate young man, keeps a secret cache of girl's clothes and a journal filled with his deepest fantasies. When his mother discovers his hidden life, she invites a series of men, including Wavie's best friend and an old family friend, to help him explore his desires. The men introduce Wavie to a world of rough, dominant sex, teaching him to embrace his role as a submissive sissy. Wavie's journey involves intense physical experiences, including being used for oral sex and...
by
waviethesissy
225
0
2
4
The Sorority's Furry Surrender to Desire
By affagato
RedQuill
River, a dominant figure, uses her hypnotic cock to ensnare three unsuspecting sorority sisters, transforming them into submissive, cock-worshipping sissies.
The sisters, initially resistant, are gradually brainwashed through a combination of sensual touch, luxurious fabrics, and River's commanding presence.
They are outfitted in UGG boots and fur coats, which serve as symbols of their new servitude and heighten their arousal.
The sisters are trained to serve River and her minions, Regina and...
by
💦
affagato
223
3
1
4
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
Uncle's Hypnotized Sissy Slut
By cockhound1967
RedQuill
An orphaned nephew is reshaped into a perfect sissy by his dominant uncle, who guides him to discover his true, submissive nature with men.
by
🖤
cockhound1967
206
0
0
5
A newly confident trans woman's friends position her for a charged encounter with a provocateur who tests her soft strength.
by
writer7212
193
0
0
10
Caged Sissy's Withering Seed Submission
By hannahcumbucket
RedQuill
Jeanette, a rebellious sissy, is locked into a self-castrating chastity device by Mistress Elara, designed to remove her ability to produce seed and turn her into a compliant, aroused clitty.
The device, equipped with fine needles, injects a painkiller to numb any sensation of the internal severance, leaving Jeanette with a perfect, leaky clitty.
Elara uses Jeanette's new state to assert her dominance, grinding against the cage and achieving orgasm, while Jeanette experiences a profound, inter...
by
❤️🔥
hannahcumbucket
193
0
0
7
A sissy bride, his wife, and their dominatrix daughter orchestrate his humiliating, cum-filled fake wedding where he must serve every groomsman.
by
🍷
shawnthebull
189
0
0
7
¡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.
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🔥
naounable
184
0
1
5
Cindy's Sissy Husband's Wild Submission
By secretsissyjamie
RedQuill
A wife seeks to humiliate her husband by transforming him into a sissy for a wild Halloween party, where he is paraded and shared with dominant men.
She dresses him in a revealing dress, complete with a wig and makeup, and equips him with a high-tech butt plug that she controls. At the party, Jamie is subjected to constant flirting and advances from the dominant men, who eventually gangbang him while Cindy watches and controls his pleasure.
by
🔥
secretsissyjamie
180
0
1
2
A conservative bully forces a liberal sissy to worship him in a steamy locker room.
by
❤️🔥
frankenteen
5.0
179
0
2
8
From Corporate Error to Intimate Surrender
By mrplains
RedQuill
A new employee at a prestigious law firm makes a costly accounting error and is given an ultimatum by the Futa CEO: become her sissy slave for the company's relaxation or be fired.
The employee chooses to serve, submitting to the CEO's every whim, including performing oral sex and being used for sexual pleasure in a variety of ways.
The employee's role evolves from a professional position to a sexual resource for the CEO and other executives, experiencing both humiliation and unexpected pleasu...
by
💋
mrplains
179
1
9
1
A cheerleader discovers her pole vaulter boyfriend's secret submissive sissy porn history and secretly begins training him to be her happy sissy sub.
by
lil_femboy
5.0
177
0
1
8
The Pumped Sissy's Public Reward
By hannahcumbucket
RedQuill
In a world where sissies are legally required to expose and use their intimate parts in public, Vanessa is subjected to a humiliating and arousing inspection. Her body is pumped and filled, leading to a powerful orgasm that results in self-feeding, followed by a post-orgasm creampie continuation. The narrative explores themes of public exposure, verbal degradation, and breeding focus, as Vanessa is used and praised for her submission.
by
❤️🔥
hannahcumbucket
176
0
0
2
Wardrobe Malfunctions Ignite Sissy's Thrill
By smut4me
RedQuill
A young exhibitionist, Pepper, seeks thrills at the beach, only to find herself in a series of wardrobe malfunctions that expose more than she intended.
Her fantasies are fueled by the sight of stunning women in revealing swimwear, leading her to a state of intense arousal and public self-pleasure.
A chance encounter with a woman who accidentally exposes herself pushes Pepper over the edge, leading to a risky and exhilarating climax.
by
💫
smut4me
172
0
1
3
Black jock discovers white sissy cam boy's secret, becomes his daddy for their viral interracial sissy channel.
by
roguedman
5.0
171
0
0
21
A shy fresher investigates park bushes and is captured by slimy tentacles that mistake his petite, feminine body for a girl's.
by
throwtosavestuff
170
0
0
12
A desperate friend begs his dominant buddy to feminize him, offering total submission in exchange for transformative release.
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glassjoe37
170
0
0
2
Sissy's Overflowing Cravings Filled Deeply
By hannahcumbucket
RedQuill
Hannah, a sissy under the 2023 Sissy Mandate, is publicly used and filled multiple times during a trip to the shops, leaving her dripping and craving more.
Upon returning home, she encounters her neighbor, Mr. Evans, who offers to help her with her "overflow problem," leading to a raw, intense breeding session in his apartment.
The encounter involves verbal degradation, praise for her role as a communal whore, and the use of a plug to keep her filled with multiple loads of semen, culminating i...
by
❤️🔥
hannahcumbucket
167
0
4
1
A shy man confesses his spanking fantasy, surprising his girlfriend who then claims dominance.
by
🍒
mrmycroft
166
0
0
20
A man hides his girlfriend's identity from his family as her insatiable, urgent hunger for him takes over his old bedroom the moment they arrive.
by
writer7212
5.0
160
0
1
1
My Threesome Videos for Cuckold Boyfriend
By don3617
RedQuill
A shy rich girl secretly films her taboo affair with a middle-aged couple to gift the videos to her cuckold boyfriend.
by
✨
don3617
159
0
0
4
Sissy's Night of Submission
By onnees
RedQuill
A neighbor catches a man in a compromising position and blackmails him into submitting to her and her feminized husband, beginning a journey of submissive training that includes oral servitude and more.
The man's initial humiliation and shame quickly give way to a twisted excitement as he is ordered to perform intimate acts, exploring themes of dominance and submission, and the blurring of gender roles.
His training involves being forced to suck his neighbor's husband's cock, and later, he is ...
by
✨
onnees
155
1
2
2
A Sissy's Awakening
By lopbunny
RedQuill
A man's deepest fantasy of sissification comes to life as his wife transforms him into the woman of his dreams, complete with satin panties, wigs, and makeup. He is introduced to a dominant alpha male who takes him for a deep anal fucking after a humiliating cock sucking session, all while being reminded of his new sissy beta role and the true nature of his desires.
by
lopbunny
153
0
0
13
Three straight guys exploring a legendary sex bunker are forced to take gender-swap pills, then get claimed by the resident Black dommes for a night of sissy training and submission.
by
morgasmthegreat
4.0
153
0
3
10
A cash-strapped honeymoon turns treacherous when the bride's father demands a night with her, witnessed by her powerless husband.
by
🔥
zarek
5.0
151
1
0
24
Aunt Cassandra's Forbidden Lingerie Fisting Feast
By skin05
RedQuill
A young man, Leo, is caught by his aunt Cassandra while dressing in her sexy lingerie. The encounter leads to a dominant and intimate experience where Leo is feminized, fisted, and pushed to his limits in a thrilling exploration of power dynamics and taboo desires.
by
🌙
skin05
146
1
0
3
A powerful wife takes control after her husband is sued for sexual misconduct, forcing him into a humiliating feminization as a means to save their reputation. Through a series of degrading lessons, she dominates him, exploring themes of power exchange, forced feminization, and public humiliation.
by
🍷
bdub
145
0
0
11
Surrendering to Cindy's Feminine Spell
By secretsissyjamie
RedQuill
Cindy uses hypnotic influence to transform Jeremy into a submissive sissy named Jamie, dressing him in feminine attire and painting his nails.
She then invites her dominant gay friends, Quincy and Chris, to join them without Jamie's knowledge, setting the stage for a night of intense exploration and submission.
The men take control, pushing Jamie's boundaries and guiding him through a transformative experience that challenges his perceptions of self and desire.
Jamie's journey involves deep e...
by
🔥
secretsissyjamie
142
0
4
1
A man from Earth is summoned to a world where men are forced to be sissies. The goddess who summons him gives him big boobs and a desire to be fucked to activate his magical powers. He is sent to a world where men are not allowed to have sex unless their owners allow it. The women that own him will jerk him off to use his cum for positions due to its magical abilities. Jerking him off causes him to be super submissive. Each time someone cums in his ass he can summon a dragon to do his bidd...
by
😈
thank31
141
0
0
15
The Party slut
By lol615378
RedQuill
(All of this is consntual, all characters are 18+)
You are Luke, a human ranger traveling with an adventuring party.
Your mates are Sylvana, an elven priestess, Tryss, a drow sorceress with a cruel streak and Frieda, a dominierend Futanari Amazon. Tryss and Frieda always make fun of you for being weak and feminine, but Sylvana seems nice. After some time, you developed a crush on her.
Using your crush on Sylvana as a bait, Tryss made you wear more feminine and tight clothes, telling you that Sy...
by
🍒
lol615378
130
0
1
7
A small-town girl, Ria, is lured into a seductive trap by her dominant boss, Shreya, who harbors a secret identity and a desperate desire for a child.
Shreya, a powerful executive, reveals herself to be a shemale, intent on impregnating Ria, who is initially resistant but ultimately succumbs to Shreya's commanding presence and erotic manipulation.
The narrative delves into themes of submission, dominance, and the erotic allure of forbidden desires, culminating in a night of intense, multi-posi...
by
🔥
riasingh
129
0
0
6
A Sissy's Awakening
By sissy_lizzy
RedQuill
A man's deepest fantasy of sissification comes to life as his wife transforms him into the woman of his dreams, complete with satin panties, wigs, and makeup. He is introduced to a dominant alpha male who takes him for a deep anal fucking after a humiliating cock sucking session, all while being reminded of his new sissy beta role and the true nature of his desires.
by
🌶️
sissy_lizzy
5.0
128
0
4
1
Keyholder forces sissy’s first ruined sissygasm
By justme2102
RedQuill
Under pink lights, caged sissy Alex rides a prostate toy to a ruined sissygasm — his keyholder's reward for three months of denial.
by
justme2102
117
0
0
3
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
Whispered Sissy Desires
By autobots
RedQuill
An 18-year-old Bengali Hindu teen, Krish, discovers a new world of crossdressing and trans porn during lockdown, finding similarities between himself and the sissies in the videos, leading to a fixation on dominant, hairy, muscular older men.
Krish's journey begins with sissy hypno training videos, leading him to mimic the acts he sees on screen, including crossdressing and self-pleasure, ultimately driving him to seek out sissy clothing to further his transformation.
by
❤️🔥
autobots
115
0
4
12
The Sissy Maid's Enchanting Estate Surrender
By karencorset
RedQuill
A crossdresser answers a job advertisement for a live-in sissy maid position, finding herself in a luxurious estate with a distinguished older man.
The maid's uniform is short, pink, and frilly, and the employer is immediately appreciative of her appearance.
The employer, Jo, is kind and gentle, and the two share a passionate kiss in the foyer.
Jo leads the maid to his bedroom, where he admires her body and teases her with his touch.
by
🔥
karencorset
112
0
3
1
A wife secretly enrolls her unsuspecting husband at a kinky institute, then separates him from her on arrival to be transformed into an obedient sissy.
by
lil_femboy
111
0
0
15
Transforming into a bimbo, Doug desperately hides his infection from his mother before she discovers he’s meant to be a collared slave.
by
👀
amanda_vallentine
110
0
0
15
RedQuill