‘sissy’ stories

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Active tags
sissy 

Category

Trapped and Trained Ch. 01

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

4.44
1.11M
714
60
1k

Feminized By My Mother Ch. 01

Shemale mother makes son a sissy.

4.43
981.2k
699
45
1k

The Babysitter

Babysitter guy becomes babysitter girl.

H
4.62
869.4k
923
65
1.3k
0

Cuckolded By My Son

Sissy watches as his son screws his wife.

4.3
857.6k
582
54
873
0

Hypnosissy 01: Becoming a Cocksucker

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

H
4.76
818.9k
1.1k
209
1.6k

Wife Makes Me A Cuckold

Wife fullfills husbands desire to be a cuckold.

4.15
813.9k
499
73
751
0

Big Black Cock: A Sissy Surprise

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

H
4.57
798.4k
289
74
439
0

My Girlfriend Made Me a Sissy

A guy is transformed into a sissy slut.

4.33
792.8k
348
42
540

Making The Perfect Husband

Before his wedding, submissive desires overcome Mark.

H
4.63
767.8k
811
155
1.2k
0

Lesser of Two Evils

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

H
4.66
642.2k
646
61
959
0

Wimp Loses to Young Black Boss

A white husband is humiliated by his black boss.

3.59
605.7k
157
28
249

Like Mother, Like Sissy

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

4.39
597.2k
568
49
797
0

Sissy's BBC Submission

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

H
4.64
583.2k
508
36
698
0

A Wonderful Wife

Wife cuckolds husband after finding his stash of stories.

4.03
575.6k
431
52
684
0

"Sissified": 12 Days of Sissy-mas

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

H
4.76
575k
824
205
1.2k
0

Sissified by My Sister

I get turned into a sissy by my younger sister.

4.16
571.9k
193
32
308

I Am My Daughter's Bitch

Daughter turns her father into a kinky cock loving slut.

H
4.58
568.9k
364
40
472
0

Hedonism Island: A BBC Discovery

Wife discovers BBC; husband gets pegged.

H
4.55
567.3k
235
60
358
0

A Sissy's New Daddy

Billie is forced to be a sub-sissy.

4.41
530.6k
433
23
564

Slip-n-Slide Bride

Man gets front-row seat to his white wife's black honeymoon.

3.41
480.2k
37
11
63
0

The Making of a White Sissy Slut

Steven becomes transformed to Stacy.

4.26
467.7k
131
8
183
0

One Week Ch. 01 Second Edition

Updated verison of One Week.

HW
4.74
458.1k
222
37
267

A Natural Sissy

She turns him into her plaything.

4.05
442.4k
93
15
141

A Deal with Daddy

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

3.84
435.2k
194
22
266
0

My Neighbor the Cop

Neighbor turns a married man bi.

H
4.61
431.1k
521
45
654

My Bully Owns My Family Ch. 01

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

3.97
426.6k
368
26
625

Black Man's White Sissy

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

4.3
424.9k
194
23
251
0

Trapped and Trained Ch. 02

The ending of the first training session.

4.48
422.6k
181
34
235

Feminized By My Mother Ch. 02

Son deals with his urges and unwanted male attention.

H
4.62
414.1k
379
51
481

His First Taste of the Real Thing

She watches her boyfriend suck another man's cock.

4.48
411.3k
196
41
254
0

A College Sissy Ch. 01

Freshman is feminized, used by male roommate and girl.

4.43
407.8k
383
21
608

His Sissy Bitch Ch. 01

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

4.43
397.9k
271
20
368

Hypnosissy 02: Becoming a Cum Slut

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

H
4.77
397.6k
414
55
555

Wide Receiver

Cheerleader punks out quarterback boyfriend to black team.

3.03
392.5k
28
7
47
0

Step by Step Sissification Ch. 01

A detailed feminization of a sissy.

4.13
386.7k
77
22
135

Hypnotized by Chelsea

He is hypnotized to think he's a girl.

4.11
384.4k
64
18
109
0

A Harmless Favor

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

H
4.65
384k
558
141
839
0

Mandingo Row

Man follows wife to see where all the white women go nightly.

3.02
382k
31
15
45

Sissy Cuckold & The Old Bull Ch. 01

Husband watches wife get impregnated by old bull.

4.13
374.9k
203
43
318

Chastity with Ex as Keyholder

Ex discovers secret chastity fetish while dating new BF!

H
4.5
372.9k
333
21
497

Trapped and Trained Ch. 03

The slut in training falls deeper into the predicament.

4.49
372.6k
135
16
167

Job Interview

Secretarial candidate proves to have something extra special.

H
4.58
367.2k
187
31
233
0

Another Prison Story

White boy meets black man.

H
4.56
365.7k
244
31
314
0

Changing Room Prank

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

H
4.69
361.5k
654
51
839

New Job, New Life as as Sissy Slut

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

H
4.5
358.3k
270
42
326

Straight Crossdresser

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

H
4.65
358.1k
592
60
855
0

Sissy

Does cum really cure zits?

4.09
350.7k
39
10
54
0

Family Chastity Story Ch. 01

A mother keeps her son in chastity with monthly milkings.

3.63
350.6k
248
63
436

He Wears The Panties

Submissive husband becomes cuckold sissy.

4.22
349.3k
111
40
151
0

Truth or Dare Sissy

A high school party game of 'truth or dare' goes wrong.

4.18
343.7k
184
38
307
0

Renee's Training

Nathan is unwillingly trained to become a sissy slave.

0
336.3k
176
72
247
0

Pool Boy Gets Dressed Up Ch. 01

Pool boy gets seduced and turned into a tranny.

H
4.67
335.5k
311
29
443

Feminizing First Step Ch. 01

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

4.39
332.7k
366
29
641

Left Alone

Tommy plays dress-up and gets caught by his neighbor.

H
4.64
332.3k
185
27
242

Sissy Cuckold & The Old Bull Ch. 02

The Old Bull takes the husband by force.

4.38
330.8k
172
40
204

The Fantasy Twist

Seduced into feminized submission.

H
4.66
328k
192
18
276

Brainwashing for Small Cocks Ch. 01

He's captured and mind-fucked into becoming gay.

4.29
327.8k
166
48
246
0

Yes, Mommy

He and his Mistress and play our mommy/little sissy game.

4.05
324.9k
55
9
85

Truth or Dare with Sisters

He plays with his wife, her sister, and wife's BF.

3.8
323.6k
59
5
109
0

What Girls Really Want

Black only white woman turns boyfriend into sissy.

4.01
319.8k
117
11
166
0

In My Dad's Panties

Feminised by his dad's shemale mistress.

H
4.57
319.5k
309
22
399
0

Making a Cuckold

She dominates, sissifies & cuckolds her boyfriend.

4.35
319.1k
120
0
165
0

The Seduction

Sister seduces brother when he comes for a visit

4.17
318.9k
77
12
119
0

iWhore

Young white man force-feminized by black gang.

4.26
317.3k
120
4
187
0

My Stepmother's Surprise

Caught and used by my stepmother, I found out a surprise.

4.28
317.2k
147
12
192
0

Sissy Finds Black Cock Bliss

Terry's journey to accepting his submissive role.

H
4.68
317k
206
18
271
0

Punished by Mother, Sister and Wife Ch. 01

They find out what I've been doing.

H
4.57
316k
159
27
267

Prison Woman

A weak cuckold ends up in prison and becomes a woman.

4.07
315.2k
118
14
166
0

My Girlfriend Made Me a Sissy Ch. 03

Dressing up like this for Jess was one thing....

H
4.56
314.5k
183
39
244

The Roommate Pt. 01

A college freshman gets slowly transformed by his roommate.

4.34
313.8k
174
6
288

Reversing Rolls

He is forcefully transitioned by university sweetheart.

3.93
309.9k
27
10
40
0

Under Mommy's Direction Ch. 01

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

4.27
309.1k
308
38
501

How to Humiliate and Degrade

A guide to humiliation and degredation from a Dom wife.

4.42
306.3k
234
40
305
0

Taste of My Girlfriend's Dildo

My girlfriend catches me - and makes me love it.

H
4.52
304.1k
178
16
253

Humiliated Sissy Husband

A wimp of a husband is forced to be a sissy by his wife.

4.27
303.6k
186
24
284

My Girlfriend Made Me a Sissy Ch. 02

Second part. Jess pushes her control further.

4.49
302k
133
18
173

So You Wanna Be A Pornstar

Grad School hipster is forced to play female porn lead.

4.25
298.9k
87
11
142
0

My Girlfriend's Sex Slave Ch. 01

My girlfriend turns me into her personal pornstar.

4.08
298.3k
137
14
219

The Roommate Ch. 01

Man gets new roommate that dominates his life.

4.37
297.5k
120
22
187
0

The Sexy Cuckold Couple Pt. 01

Cuckold couple becomes an owned couple.

4.31
295.5k
340
16
527

The Toyboy Experiment

A young straight guy submits to an older man.

H
4.63
292.5k
381
26
499

Halloween Agreement

I agree to Her costume suggestion, and then much more...

4.44
288.3k
96
19
126
0

Sissy Boy Secretary

Dominant boss & secretary interact.

4.29
286.3k
55
10
77

Dominant Wife, Cuckold's Reward

A devoted submissive husband, a dominant wife.

4.23
285.4k
102
11
149
0

Sissy Housewife Learns to Eat Cum

Sissy Tiffany forced to eat her yummy cum by Miss Jennifer.

4.27
278.6k
111
11
160
0

Kinky Neighbors

Cheating wife cuckolds hubby with kinky neighbor.

4.05
278.2k
73
35
116
0

Feminized by My Girlfriend Ch. 02

Feminization taken to a whole new level.

4.4
277.8k
140
0
173

My Bully Owns My Family Ch. 02

Marcus asserts ownership of Mom and my sister.

4.25
274k
183
3
264

Caitlin and Mistress Vicky

A completely whipped husband is feminized by his wife.

4.34
273.7k
104
18
159

My Strapon Fantasy

A girl helps her boyfriend live out his fantasy.

H
4.5
271.5k
144
24
208
0

Punished by Mother, Sister and Wife Ch. 04

He's Teased and Humiliated by Mom and Sister.

H
4.52
269.5k
63
49
86

Domme-in-Law Ch. 02

Jim's Mother-in-Law continues his education.

0
269.1k
84
7
124

My Life as a Sissy Step-Son Ch. 01

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

4.34
269k
214
17
310
0

New Beginnings

Guy is feminized by mothers's assistant.

H
4.51
268.3k
155
18
214
0

Little Sex Toy Ch. 01

First experience with a forceful and seductive man.

4.49
267.7k
203
16
265

Sissified by My Sister Ch. 02

A couple weeks later, my sister brings a friend.

4.28
267.5k
89
19
127

Jasmine Fucks My Wife

He could never have imagined it.

4.02
267.1k
130
24
173
0

Craig's New Life

Forced to play for the other team.

4.48
265.5k
102
25
137
0

BoyTrainers, Inc.

A kidnapped 18 yr old boy is turned into a wiggling priss.

4.22
264.7k
131
16
176
0

Trapped and Trained Ch. 05

Candi comes back for the start of a long, long night.

4.47
263.2k
94
10
119
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