‘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
1.1M
707
59
1k

Feminized By My Mother Ch. 01

Shemale mother makes son a sissy.

4.43
974.4k
694
45
1k

The Babysitter

Babysitter guy becomes babysitter girl.

H
4.62
861.4k
914
63
1.2k
0

Cuckolded By My Son

Sissy watches as his son screws his wife.

4.29
853.8k
573
52
828
0

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

Wife Makes Me A Cuckold

Wife fullfills husbands desire to be a cuckold.

4.15
808.6k
496
72
737
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

My Girlfriend Made Me a Sissy

A guy is transformed into a sissy slut.

4.33
788k
346
42
530

Making The Perfect Husband

Before his wedding, submissive desires overcome Mark.

H
4.63
759.9k
792
155
1.1k
0

Lesser of Two Evils

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

H
4.65
636.6k
638
60
939
0

Wimp Loses to Young Black Boss

A white husband is humiliated by his black boss.

3.59
603.7k
154
28
242

Like Mother, Like Sissy

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

4.39
592.6k
564
49
785
0

Sissy's BBC Submission

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

H
4.64
579.2k
504
36
687
0

A Wonderful Wife

Wife cuckolds husband after finding his stash of stories.

4.03
572.5k
431
52
679
0

Sissified by My Sister

I get turned into a sissy by my younger sister.

4.16
569k
192
32
306

"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

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

Hedonism Island: A BBC Discovery

Wife discovers BBC; husband gets pegged.

H
4.54
563.3k
234
59
348
0

A Sissy's New Daddy

Billie is forced to be a sub-sissy.

4.41
527.5k
430
23
561

Slip-n-Slide Bride

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

3.41
478.5k
37
11
60
0

The Making of a White Sissy Slut

Steven becomes transformed to Stacy.

4.26
466.4k
131
8
180
0

One Week Ch. 01 Second Edition

Updated verison of One Week.

HW
4.74
457.4k
222
37
265

A Natural Sissy

She turns him into her plaything.

4.05
441.4k
93
15
140

A Deal with Daddy

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

3.84
434.4k
193
22
261
0

My Neighbor the Cop

Neighbor turns a married man bi.

H
4.61
428.9k
514
45
642

Black Man's White Sissy

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

4.3
423.3k
190
23
244
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

Trapped and Trained Ch. 02

The ending of the first training session.

4.48
420.2k
179
33
231

Feminized By My Mother Ch. 02

Son deals with his urges and unwanted male attention.

H
4.62
412.3k
378
51
480

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 College Sissy Ch. 01

Freshman is feminized, used by male roommate and girl.

4.43
405k
380
21
599

His Sissy Bitch Ch. 01

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

4.43
396.3k
271
20
366

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

Wide Receiver

Cheerleader punks out quarterback boyfriend to black team.

3.03
391.1k
28
7
45
0

Step by Step Sissification Ch. 01

A detailed feminization of a sissy.

4.13
385.6k
77
22
133

Hypnotized by Chelsea

He is hypnotized to think he's a girl.

4.11
383.6k
64
18
108
0

Mandingo Row

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

3.02
381k
31
15
43

A Harmless Favor

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

H
4.66
377.2k
551
140
826
0

Sissy Cuckold & The Old Bull Ch. 01

Husband watches wife get impregnated by old bull.

4.13
373.5k
201
43
314

Trapped and Trained Ch. 03

The slut in training falls deeper into the predicament.

4.49
370.7k
135
16
166

Chastity with Ex as Keyholder

Ex discovers secret chastity fetish while dating new BF!

4.49
370.6k
322
21
476

Job Interview

Secretarial candidate proves to have something extra special.

H
4.58
366.6k
187
31
232
0

Another Prison Story

White boy meets black man.

H
4.57
364.4k
244
31
311
0

Changing Room Prank

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

H
4.69
359.4k
652
49
831

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

Straight Crossdresser

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

H
4.65
351.7k
589
59
848
0

Sissy

Does cum really cure zits?

4.09
350.4k
38
10
53
0

He Wears The Panties

Submissive husband becomes cuckold sissy.

4.22
347.9k
111
40
150
0

Family Chastity Story Ch. 01

A mother keeps her son in chastity with monthly milkings.

3.63
347.1k
246
63
429

Truth or Dare Sissy

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

4.18
341.9k
183
38
304
0

Renee's Training

Nathan is unwillingly trained to become a sissy slave.

0
335.5k
175
72
244
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

Left Alone

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

H
4.64
331.7k
185
27
242

Sissy Cuckold & The Old Bull Ch. 02

The Old Bull takes the husband by force.

4.37
329.5k
172
40
203

Feminizing First Step Ch. 01

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

4.39
327.8k
363
29
634

The Fantasy Twist

Seduced into feminized submission.

H
4.66
327.2k
190
17
273

Brainwashing for Small Cocks Ch. 01

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

4.29
326.7k
164
48
243
0

Yes, Mommy

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

4.05
324k
55
9
86

Truth or Dare with Sisters

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

3.79
322.8k
59
5
105
0

What Girls Really Want

Black only white woman turns boyfriend into sissy.

4.01
319.2k
116
11
164
0

In My Dad's Panties

Feminised by his dad's shemale mistress.

H
4.57
318.8k
307
22
395
0

Making a Cuckold

She dominates, sissifies & cuckolds her boyfriend.

4.35
318.6k
119
0
163
0

The Seduction

Sister seduces brother when he comes for a visit

4.17
318.5k
77
12
119
0

iWhore

Young white man force-feminized by black gang.

4.27
316.5k
120
4
186
0

My Stepmother's Surprise

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

4.28
316.4k
146
12
190
0

Sissy Finds Black Cock Bliss

Terry's journey to accepting his submissive role.

H
4.69
316k
205
18
268
0

Punished by Mother, Sister and Wife Ch. 01

They find out what I've been doing.

H
4.56
315.3k
158
27
262

Prison Woman

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

4.07
314.3k
119
14
166
0

My Girlfriend Made Me a Sissy Ch. 03

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

H
4.56
313.3k
182
38
237

The Roommate Pt. 01

A college freshman gets slowly transformed by his roommate.

4.34
312.2k
171
6
284

Reversing Rolls

He is forcefully transitioned by university sweetheart.

3.92
309.4k
27
10
39
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

How to Humiliate and Degrade

A guide to humiliation and degredation from a Dom wife.

4.41
304.9k
234
40
302
0

Taste of My Girlfriend's Dildo

My girlfriend catches me - and makes me love it.

H
4.52
303.4k
176
16
243

Humiliated Sissy Husband

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

4.27
300.8k
185
24
282

My Girlfriend Made Me a Sissy Ch. 02

Second part. Jess pushes her control further.

4.49
300.8k
130
18
168

So You Wanna Be A Pornstar

Grad School hipster is forced to play female porn lead.

4.25
298.3k
86
11
140
0

My Girlfriend's Sex Slave Ch. 01

My girlfriend turns me into her personal pornstar.

4.08
297.5k
136
14
215

The Roommate Ch. 01

Man gets new roommate that dominates his life.

4.37
296.5k
120
22
186
0

The Sexy Cuckold Couple Pt. 01

Cuckold couple becomes an owned couple.

4.31
292.7k
337
16
511

The Toyboy Experiment

A young straight guy submits to an older man.

H
4.63
290k
380
26
491

Halloween Agreement

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

4.43
287.7k
96
19
123
0

Sissy Boy Secretary

Dominant boss & secretary interact.

4.29
285.8k
55
10
76

Dominant Wife, Cuckold's Reward

A devoted submissive husband, a dominant wife.

4.22
284.2k
101
11
144
0

Sissy Housewife Learns to Eat Cum

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

4.27
277.9k
111
11
158
0

Kinky Neighbors

Cheating wife cuckolds hubby with kinky neighbor.

4.05
277.4k
72
35
113
0

Feminized by My Girlfriend Ch. 02

Feminization taken to a whole new level.

4.4
276.9k
138
0
170

Caitlin and Mistress Vicky

A completely whipped husband is feminized by his wife.

4.34
272.9k
104
18
158

My Bully Owns My Family Ch. 02

Marcus asserts ownership of Mom and my sister.

4.25
272.2k
180
3
261

My Strapon Fantasy

A girl helps her boyfriend live out his fantasy.

H
4.5
270.8k
143
24
205
0

Punished by Mother, Sister and Wife Ch. 04

He's Teased and Humiliated by Mom and Sister.

H
4.52
269.1k
62
49
85

Domme-in-Law Ch. 02

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

0
268.4k
84
7
121

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

New Beginnings

Guy is feminized by mothers's assistant.

H
4.51
267.6k
154
18
212
0

Little Sex Toy Ch. 01

First experience with a forceful and seductive man.

4.48
266.9k
201
16
262

Sissified by My Sister Ch. 02

A couple weeks later, my sister brings a friend.

4.29
266.5k
89
19
127

Jasmine Fucks My Wife

He could never have imagined it.

4.02
265.9k
131
23
171
0

Craig's New Life

Forced to play for the other team.

4.48
265.1k
101
25
135
0

BoyTrainers, Inc.

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

4.22
264.2k
131
16
175
0

Trapped and Trained Ch. 05

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

4.47
262k
94
9
119
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