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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)
Femboys Secret Prison Submission Awakening
By oritcohen130
RedQuill
A delicate hacker serves his sentence in a violent prison, his revealing clothes catching the eye of a dominant cellmate.
by
🖤
oritcohen130
110
0
0
26
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
A college athlete, Walter, develops a deep crush on Laine, a confident and skilled cheerleader, after watching her practice from afar. Their first meeting at a party leads to a slow-burning connection, culminating in a nervous yet tender first kiss that hints at a loving and gentle dynamic, where Laine takes the lead with a subtle yet commanding presence.
by
lil_femboy
102
0
0
41
A feminine boyfriend, encouraged by his girlfriend, steps into the world of cross-dressing, experiencing a slow burn of self-discovery and arousal. His journey includes learning the art of makeup application, submitting to her strap-on, and ultimately finding pleasure in a pegging session filled with intense eye contact and whispered praise.
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😈
blackmagicruby
101
0
0
5
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
99
0
0
8
Her Enduring Ache
By justme2102
RedQuill
Mistress Victoria brings her locked sissy home from the club, then pegs her into a rolling sisygasm of denied, worshipful ecstasy.
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💦
justme2102
98
0
0
10
An 18-year-old named Nick, who is struggling with his sexuality and a newfound interest in crossdressing, seeks guidance from Bob, a kind and understanding counselor in his 50s at the Salvation Army.
Bob encourages Nick to explore his curiosity by dressing in women's clothing, leading to a seductive and transformative experience that challenges Nick's understanding of his own desires.
The narrative delves into themes of self-discovery, sexual awakening, and the complexities of consent and mani...
by
🌙
maninnylons
98
0
1
19
Sissy Roommate's Surprise Welcome
By noobking
RedQuill
A college bottom transforms into a sissy to surprise his roommate, sparking a night of jealous passion and desperate submission.
by
❤️🔥
noobking
95
1
1
6
The Sorority's Furry Surrender to Desire
By lutheran
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
🖤
lutheran
95
2
1
2
@fs21-minimal Jane comes home to her cum loving "roommate with benefits", Ed. Ed knows Jane is into witchy magic stuff but doesn't place much faith in that. What Ed loves is Jane allows him to eat creampies Jane's lovers have left in her lovely pussy. Ed knows it is embarrassing, but it has always been his kink. Tonight Jane has returned to the apartment with just such a cum-filled treat. Bob laps it up eagerly as Jane encourages him. Ed's tongue drives her to orgasm. As the chapter comes to a c...
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💦
femslut21
94
0
0
14
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.
by
👀
amanda_vallentine
92
0
0
25
Inspected Sissy's Rewired Ecstasy Training
By cucumber
RedQuill
A slave, Leo, undergoes a thorough and dehumanizing medical inspection, where he is subjected to a series of invasive and humiliating examinations.
His body is meticulously assessed for its service capabilities, with a particular focus on his anal aperture and prostate stimulation.
The inspection culminates in a forced sissy training session, where Leo is made to experience intense, internal orgasms using a vibrator, ultimately certifying him as ready for ownership.
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🫦
cucumber
92
0
0
11
A powerful male boss's secret fascination with sissy porn is exposed by his assistant, who uses this information to blackmail him into performing increasingly feminized acts. The assistant, posing as a mysterious mistress, manipulates the boss into wearing lingerie under his work clothes and then reveals his desires to a spa technician, forcing him to undergo a full transformation into a girly, sissy princess.
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🍷
jizzelle187
91
1
0
7
A dainty tutor's confession to his cheerleader crush backfires when she confronts him in the locker room, revealing a devastating truth.
by
💋
cuck7890
88
0
1
24
Mark's Ass Fucked While He Sucks His Own Cock
By dudeindenver
RedQuill
A straight husband, Mark, harbors a secret fantasy of sucking cock, which his wife, Sarah, helps him explore. Through a series of intimate and explicit acts, Sarah guides Mark to suck his own cock while she stimulates his prostate with a dildo, leading them both to a climax of shared intimacy and mutual satisfaction.
The couple engages in a variety of sexual activities, including anal play and oral sex, as they explore Mark’s hidden desires and Sarah’s dominant role in their relationship. They ...
by
💫
dudeindenver
88
2
1
5
Mistress Demands Sissy Service Truck Stop Gloryhole
By robininthebush
RedQuill
Futa mistress live-streams her sissy's truck-stop parade in corset and cage, remote plug humiliates, then fucks his face and ass at glory hole.
by
💜
robininthebush
87
0
3
36
Sister Catches Me Jerking Off
By strapondirk
RedQuill
A brother is caught in a private moment by his sister, whose forbidden curiosity turns shock into a dangerous new intimacy.
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🍒
strapondirk
87
0
1
41
Alpha Wolf Claims Bunny Sissy
By kittylove
RedQuill
A disciplined athlete's experimental serum surges him into a petite bunny Sissyfur, his heat-scent driving the lab's Alpha Rut security wolf to claim him w
by
💫
kittylove
86
0
1
1
The Sissy's New Obedience
By onnees
RedQuill
A submissive man is caught masturbating to sissy hypno videos and is blackmailed by his neighbor into servicing her feminized husband, leading to a degrading and humiliating experience. The themes of forced feminization, verbal degradation, and praise kink are explored in detail as the man is trained to be a submissive cocksucker, with the promise of more to come.
by
✨
onnees
85
0
0
3
Desperate fiancé Robert risks a mysterious modeling shoot for $20K to save his relationship, but the agency's erotic demands test his limits.
by
💫
barbieboy2323
84
0
0
15
Girlfriend Catches Sissy Panty-Sniffer
By pilkypilky
RedQuill
My girlfriend discovers my lingerie secret and forces me into servitude for her and her bratty friends in the ultimate sissy humiliation makeover.
by
🌶️
pilkypilky
84
0
0
5
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
83
0
0
10
Jock to Sissy
By missygurl1
RedQuill
Homophobic jock Jay is blackmailed by girlfriend's sissy best friend Riley.
by
✨
missygurl1
81
0
1
8
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
79
0
1
8
Рок-группе позарез нужна солистка. А кто ищет, тот всегда найдет. Шоу начинается...
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tesla_1998
78
0
0
10
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_
76
0
0
24
Harry's Sissy adventures
By cjnkjcn
RedQuill
Shy groom Harry submits when witch bride Daphne reveals her dominant nature on their wedding night, redefining their roles.
by
🔥
cjnkjcn
76
0
2
2
Burgundy Silk and Forbidden Desires
By ayoo
RedQuill
A gay man, Crane, playfully steals his lover's silky panties and prepares for a night of seduction, meticulously cleaning himself in the shower and donning the delicate lingerie. He awaits his lover, Elias, who returns from his shower, naked and aroused, and is captivated by Crane's daring attire. The two engage in a passionate encounter, with Elias praising Crane's beauty and initiating a night of intense pleasure.
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😈
ayoo
74
0
0
4
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
73
0
0
3
Neighbor Catches Husband in Wife's Lingerie
By pilkypilky
RedQuill
A neighbor catches a sissy husband masturbating in wife's panties, blackmails him into pink satin maid uniform and filmed foot worship.
by
🌶️
pilkypilky
73
0
0
12
A college guy's quiet Sunday becomes self-discovery as he secretly tries on panties and makeup, chasing the thrill of being Sasha for his first date.
by
daram
72
0
0
7
Feminine 18-year-old Cameron’s new stepbrother and father move in, immediately teasing his masculinity and parading their dominance—starting his sissy tran
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roguedman
72
0
0
16
A retro superheroine's costume malfunctions lead to obscene public victories, witnessed by her oblivious son on live TV.
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🔥
e806659
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 humiliated lawyer now his wife's obedient housewife kneels beneath her desk, tasting her arousal while she closes a deal on a video call.
by
🖤
lyttaren
67
0
0
10
A tall, muscular, black man with an impressive physique returns home to find a feminized sissy, Jamie, waiting on his porch, a gift from his sister. Jamie, locked in a chastity cage and ready to be dominated, is taken inside and used by Derrick, who explores Jamie's deep-seated desires for BBC worship, anal gaping, and submission, ultimately claiming Jamie as his own.
by
🍒
exoticfun
67
0
0
7
A bored middle-aged manager discovers a magical board game at his stunning young co-worker's apartment—and his first move transforms his boxers into blue satin panties, awakening desires he'd buried for years.
by
🍒
dicejp
66
0
0
12
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.
by
💜
the_barber
65
0
0
16
Jagan, a man with a small cock and deep insecurities, embarks on a transformative journey during a work trip to a bustling city. He explores his secret desires by purchasing and wearing girly clothes, finding excitement and empowerment in the process. He delves into the world of sissy porn and online dating, ultimately leading to a thrilling encounter in a hotel restroom where he sucks off a stranger, embracing his newfound identity and desires.
by
🫦
gayatri23
65
0
1
13
A wife introduces her husband to pegging and hypnosis, unlocking his hidden submissive desires.
by
daddysaysso
5.0
63
0
0
8
John's Secret Jiggle
By mxaaa
RedQuill
John, an 18-year-old with a secret fascination for the sensation of wearing water-filled balloons as breasts and hips, finds himself caught off guard when his sister Emily discovers his unusual hobby. Instead of judgment, Emily shows curiosity and support, leading to a deeper exploration of John's desires and a newfound sense of acceptance and confidence. Emily introduces John to more realistic silicone forms, guiding him through a journey of self-discovery and sensual experimentation, ultimatel...
by
🫦
mxaaa
63
0
1
5
Tanya's secret cross-dressing life is exposed by his girlfriend, who seizes control of his keys—and his feminized desires.
by
redfist
62
0
1
8
A sissy is auctioned to a wealthy dominatrix and forced through a week of public humiliations, filmed for a secret panel.
by
🌶️
chubsissy87
5.0
61
0
0
47
A porky pantyboy is teased, humiliated, and bullied by a petite domme at a party in front of her giggling girlfriends.
The domme makes fun of his ridiculous pink frilly sissy panties and teases him for being a chubby tinker.
She makes him hump a pillow in front of her and oink like a pig.
She takes her panties off and dangles them in front of his face, letting him sniff them.
The domme forbids him to look above her waist.
The domme ends the session by recording him oinking for future blackm...
by
💦
ultrapulp
60
0
0
3
New stepdad and his dominant son move in, targeting feminine Cameron for sissification and submission.
by
roguedman
59
0
0
13
Submissive Sissy Bunny Fucks Dragon Shemale
By kittylove
RedQuill
A towering shemale claims a timid sissy at a bar, ruthlessly educating him in total submission to become her perfect plaything.
by
💫
kittylove
5.0
58
0
0
3
A humorous comic book story about Sissy Fist (The Fist of Justice!) as she fights to protect Psalport. 🍬 (upd. 07/09/26)
by
thedentedpen
5.0
57
0
0
11
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.
by
🔥
mikeg
56
0
0
3
RedQuill