‘sissy’ stories

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Active tags
sissy 

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Hypnosissy 01: Becoming a Cocksucker

Straight guy watches porn tapes that are not what they seem.

H
4.77
809.5k
1.1k
208
1.5k

The Babysitter

Babysitter guy becomes babysitter girl.

H
4.62
861.5k
914
63
1.2k
0

"Sissified": 12 Days of Sissy-mas

Straight man is turned into a submissive sissy by...

H
4.76
568.1k
817
202
1.1k
0

Making The Perfect Husband

Before his wedding, submissive desires overcome Mark.

H
4.63
759.9k
792
155
1.1k
0

Trapped and Trained Ch. 01

Man is drugged, then dressed up and trained to be a slut.

4.44
1.1M
707
59
1k

Feminized By My Mother Ch. 01

Shemale mother makes son a sissy.

4.43
974.4k
694
45
1k

Changing Room Prank

Mark and Greg help me discover myself with a harmless prank.

H
4.69
359.4k
652
49
831

Lesser of Two Evils

A man's choices will transform him into a cum slut.

H
4.65
636.6k
638
60
939
0

The Seductive Seed of a Tranny MILF

One sip and you just might find yourself hooked like he did.

H
4.75
198k
616
39
843
0

Straight Crossdresser

Guy dresses as a girl on Halloween & ends up performing as one.

H
4.65
351.8k
589
59
848
0

Cuckolded By My Son

Sissy watches as his son screws his wife.

4.29
853.9k
573
52
828
0

Like Mother, Like Sissy

A sissy learns he is a princess . . . and a sperm whore.

4.39
592.6k
564
49
785
0

A Harmless Favor

A young wife assists her young husband to become a sissy.

H
4.66
377.2k
551
140
826
0

My Neighbor the Cop

Neighbor turns a married man bi.

H
4.61
428.9k
514
45
642

Sissy's BBC Submission

Young man entranced by BBC, is pushed to be a sissy.

H
4.64
579.2k
504
36
687
0

Wife Makes Me A Cuckold

Wife fullfills husbands desire to be a cuckold.

4.15
808.6k
496
72
737
0

Dorm Room Dick Down

A shy freshman’s big butt gets him into trouble.

H
4.7
146.1k
447
20
677
0

A Wonderful Wife

Wife cuckolds husband after finding his stash of stories.

4.03
572.5k
431
52
679
0

A Sissy's New Daddy

Billie is forced to be a sub-sissy.

4.41
527.5k
430
23
561

Hypnosissy 02: Becoming a Cum Slut

New teen cock sucker craves more big cock and loads of cum.

H
4.77
395k
411
54
551

A College Sissy Ch. 01

Freshman is feminized, used by male roommate and girl.

4.43
405.1k
380
21
599

The Toyboy Experiment

A young straight guy submits to an older man.

H
4.63
290k
380
26
491

Feminized By My Mother Ch. 02

Son deals with his urges and unwanted male attention.

H
4.62
412.3k
378
51
480

Roommate Dress-Up

Straight guy is feminized by female beauty.

H
4.7
231.6k
372
49
610
0

I Am My Daughter's Bitch

Daughter turns her father into a kinky cock loving slut.

H
4.58
567.4k
364
40
471
0

My Bully Owns My Family Ch. 01

Bully turns Mom, Dad, Sister, and I into BBC sluts.

3.97
423.2k
363
26
614

Feminizing First Step Ch. 01

A mother begins to feminize her son. First, a new swimsuit.

4.39
327.8k
363
29
634

BBC: Like Son, Like Father

Father catches son sucking BBC & gets very curious.

H
4.67
233k
360
60
506
0

My Girlfriend Made Me a Sissy

A guy is transformed into a sissy slut.

4.33
788.1k
346
42
530

Dream Girl Pt. 01

Get the girl... or become a girl for BBC.

H
4.7
184.6k
346
36
579

Sissification 101: Ch. 01

Straight guy is caught watching sissy porn and…

H
4.7
202.7k
339
42
604

The Sexy Cuckold Couple Pt. 01

Cuckold couple becomes an owned couple.

4.31
292.7k
337
16
511

Chastity with Ex as Keyholder

Ex discovers secret chastity fetish while dating new BF!

4.49
370.7k
322
21
476

Jake's New Mommy Ch. 01

18-year-old runaway Jake is 'rescued' by a mysterious woman.

H
4.66
119.3k
319
46
554
0

Pool Boy Gets Dressed Up Ch. 01

Pool boy gets seduced and turned into a tranny.

H
4.67
334.2k
310
29
440

In My Dad's Panties

Feminised by his dad's shemale mistress.

H
4.57
318.8k
307
22
395
0

The Prostate Exam Pt. 01

Married guy, outed as the anal slut he really is, by his Doc.

H
4.51
251.6k
304
15
450

Maid The Wrong Bet...

A French maid's outfit turns him into a sissy.

H
4.61
256.4k
303
24
385
0

Under Mommy's Direction Ch. 01

A Mother decides to sissify her Son for a better life.

4.27
306.1k
299
38
486

Sissy for Mommy's Nipple Cream Ch. 01

Mom uses breastfeeding to turn her son into a sissy cumslut.

4.44
210.9k
297
5
487

The Jock and the Sissy

Sissy offers Jock his lips after being saved from bullies.

H
4.62
131.6k
292
27
422
0

Big Black Cock: A Sissy Surprise

A wife joins her husband as a slut for a teen BBC.

H
4.57
792k
288
73
428
0

Groomed to Depravity Ch. 01

A college boy's life goes awry on Halloween.

4.41
196k
287
12
465

But I'm a Boy, Not a Cheerleader!

Accidentally a cheerleader at the basketball party!

H
4.67
125.7k
278
19
479

His Sissy Bitch Ch. 01

A man's employer uses him for more than an employee.

4.43
396.3k
271
20
366

Amanda

A boy comes under the control of a dominant girl.

4.42
219k
270
31
379
0

New Job, New Life as as Sissy Slut

Man gets a job cleaning a house, but gets much more!

H
4.5
357.6k
269
42
325

Feminized by BBC Friend Ch. 01

My BBC friend slowly feminize me.

4.42
192.1k
267
11
466

A Good Fucking Examination

Tyler receives a very special treatment from Doctor Kendra.

H
4.77
91.2k
263
49
431
0

The Society

He stumbles into a world dominated by women.

H
4.66
228.1k
258
32
351

The New Girls

Femboy gets turned into a sissy by the New Girls in school.

H
4.68
135.7k
257
62
428

Sissy, Hypnotized

A night out results in triggers unleashed for this sissy.

H
4.66
190.1k
256
29
381
0

Full Scholarship

Naive college kid tries to make ends meet, gets in deep.

H
4.72
98.8k
255
34
390
0

A Better Life through Chastity

A young man is forced into chastity by his loving girlfriend.

H
4.57
163.3k
253
29
437
0

Drunk Friend to Sissy Slut

Game of Edward 40 Hands turns me into my true slutty self

H
4.57
172k
253
22
363
0

Hypnosissy 04: Cum Cravings

Videos entrench his hunger for cock and cum.

H
4.77
202.9k
251
52
323

My Estranged Sister Eve

Merry Xmas/Incest - Wincest sissy w/ his transgender sister.

H
4.67
87.5k
250
22
362

Sissy Meets Daddy

A sissy loses her virginity.

H
4.56
180.9k
249
25
360
0

Family Chastity Story Ch. 01

A mother keeps her son in chastity with monthly milkings.

3.63
347.1k
246
63
429

The Man That Converted Me

A young man is snowed in & turned out on a mountain getaway.

H
4.75
76.8k
245
39
369

Another Prison Story

White boy meets black man.

H
4.57
364.4k
244
31
311
0

Barbie's BBC Beginning

A sissy husband gets roped into interracial sex by his wife.

H
4.64
163.1k
241
30
336
0

Hedonism Island: A BBC Discovery

Wife discovers BBC; husband gets pegged.

H
4.54
563.3k
234
59
348
0

How to Humiliate and Degrade

A guide to humiliation and degredation from a Dom wife.

4.41
304.9k
234
40
302
0

Bikini Boi

Brother's friends make me wear my Sister's Bikini...

H
4.54
178.8k
232
16
336
0

The Vixen

A young man is seduced and feminized by a red headed beauty.

H
4.72
139.5k
231
23
334
0

Entering and Breaking

An intruder humiliates a husband in front of his wife.

4.3
242.9k
231
51
310
0

Social Media Star

Boy becomes an unwilling lingerie model for online viewers.

H
4.55
118.3k
226
31
419

I Own You

A young man becomes his well endowed boss's personal bitch.

4.45
192.4k
225
30
351
0

My Aunt's Anniversary Cruise

Cruise leads to sissification and an interracial gangbang.

H
4.55
97.2k
225
23
292
0

Personally Trained

A not-so-straight guy gets turned out at the gym.

H
4.69
95.1k
224
20
350
0

One Week Ch. 01 Second Edition

Updated verison of One Week.

HW
4.74
457.4k
222
37
265

Becoming His Sissy Pt. 01

Straight guy discovers the pleasures of being a sissy.

H
4.8
86.7k
217
17
342

Epidemic

In a world without women, men must keep humanity alive.

4.44
174.7k
214
30
251
0

My Life as a Sissy Step-Son Ch. 01

Charles discovers his Step-Son's Secret, and makes a deal.

4.34
267.9k
214
17
306
0

The Whole Package

Femboy dreams about futa and receives more than he dreamed.

H
4.88
70.9k
213
47
368
0

Four Blessings Pt. 02

Aiden dives in deeper and so does his futa harem.

H
4.82
45k
207
68
259

Sissy Finds Black Cock Bliss

Terry's journey to accepting his submissive role.

H
4.69
316k
205
18
268
0

A Perverse Plan

Hot wife turns hubby into a crossdressing sissy.

H
4.56
225k
204
31
329
0

Worlds First Futa - Sissy Maid

Dominant Futa hires a sissy boy to be her maid.

H
4.64
64k
204
21
298
0

Finding a Perfect First Daddy Cock

A young college virgin's first time submitting to a daddy.

H
4.7
148.7k
203
16
315
0

How I Became a BBC Sissy Slut

A reluctant sissy finds herself addicted to BBC.

H
4.56
198.4k
201
24
272
0

The Looking Glass

The Birth of Addiction.

HW
4.84
144.5k
201
66
304
0

Little Sex Toy Ch. 01

First experience with a forceful and seductive man.

4.48
266.9k
201
16
262

Sissy Cuckold & The Old Bull Ch. 01

Husband watches wife get impregnated by old bull.

4.13
373.5k
201
43
314

Working the Holidays

Classic Christmas tale of blackmail and forced feminization.

H
4.58
145k
200
18
289

Hypnosissy 06: Educated to be Pegged

Cock sucker's training is advanced to hypno videos on anal.

H
4.77
116.1k
199
104
260

Rite of Passage Ch. 03

Jamie's corruption furthers with help from his crush, Kelly.

H
4.72
97.3k
198
25
234

Meeting Mommy

A sorry sissy remembers the first time she met her Mommy.

H
4.61
223k
197
16
300
0

Pool Day Takes a Turn

Randy forgot his bathing suit.

H
4.64
106.2k
197
26
311

Sissified Ch. 01

Young boy is helped by his hot tutor in his transformation.

4.36
185.5k
196
12
392

His First Taste of the Real Thing

She watches her boyfriend suck another man's cock.

4.49
410.4k
195
41
244
0

A Deal with Daddy

Gay incest! Dad lets son fuck mom, for a price.

3.84
434.4k
193
22
261
0

Sissified by My Sister

I get turned into a sissy by my younger sister.

4.16
569k
192
32
306

Black Man's White Sissy

A white punk learns to be feminine to his black master.

4.3
423.3k
190
23
244
0

The Fantasy Twist

Seduced into feminized submission.

H
4.66
327.2k
190
17
273

Sleepover

Two best friends explore in bed.

H
4.71
77.6k
189
21
289
0

White Dom Turned Sissy for BBC

Alpha white man learns his inferiority to BBC.

H
4.71
93.7k
189
20
316

Literally a Face Pussy

A pantyboy gets gangbanged by members of the football team.

H
4.54
96.6k
189
13
318
0

My New Daddy Ch. 01

A young man discovers joy in the arms of an older dom.

H
4.53
108.5k
187
9
271
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