‘sissy’ stories

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sissy 

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Wife and I Get a Roommate Ch. 02

Man takes on his first real cock.

H
4.68
249.4k
179
26
228

New Year Cuckold Ch. 02

Sissy gets a brutal surprise.

3.91
74.8k
31
7
35

Feeling Bossy Pt. 04

Making you my sissy.

4.41
181.9k
37
13
61

Monster Breed Ch. 03

Finally some sex going on!

3.99
33.4k
13
8
19

Fantasy to Reality Ch. 02

A sissy's fantasy becomes a reality.

4.45
87.5k
26
9
33

Asian Bimbo Sissy Slut Ch. 01

Curiosity comes out of the closet.

3.49
76.3k
18
3
23
0

Shattered

A terrifying, hot based-on-a-true-story of how I was outed.

4.27
86.3k
30
11
38
0

Fantasy to Reality

A sissy's fantasy becomes a reality.

4.24
163k
47
14
74

Thank You For My Life

A sissy maid describes a day in her life.

4.32
78.8k
43
11
59
0

Wife: A Typical Saturday Morning

Hot wife encourages hub's gender bender fantasies.

4.19
80.5k
22
2
28
0

Chastity with Ex as Keyholder Ch. 04

Ex. continues enforced chastity and oversees cleaning.

4.44
142.5k
56
11
82

Sissy Takes It Rough

Crossdressing sissy has black men get rough with her.

4.01
141.7k
57
7
76
0

The Honeymoon Is Over

Newly married wife and mother-in'law dominate husband.

4.36
194.3k
75
36
122
0

Mistress Jaz's Sissy Slut

My first training session with a Beautiful Black Goddess.

3.78
75.2k
7
3
12
0

Fifi's Long Wait

Fifi the maid needs to cum so badly.

H
4.65
112.7k
61
7
89
0

Wife in Control Ch. 04

A husband endures further humiliation for lack of control.

4.16
143.7k
21
5
31

A Game within a Game Ch. 02D

New games - but not at all funny.

H
4.59
26.1k
7
4
9

A Game within a Game Ch. 02C

Dr. Cathy - a visit to a psychiatrist.

H
4.51
26.9k
7
3
9

A Very Hard Working Girl

Sexy slut does what she does best, services men.

H
4.56
133.3k
67
5
78
0

Church Nerd Humiliation Junkie

A nerd's masochistic fantasies take him to orgasm.

3.56
45.7k
10
1
18
0

The Lodger Ch. 02

Menage a trois with the black lodger develops.

4.17
92k
68
14
76

A Perfect Cuckoldress Wife

A cuckolded sissy husband is happy watching her.

4.37
182.2k
70
10
89
0

Internet Meeting Ch. 03

Preparing for Charles.

4.29
14k
1
0
3

Sissy Maids & Sex Slaves Ch. 01

A mistress meets her sissy maid and more.

4.45
68.6k
16
3
25
0

Internet Meeting Ch. 02

Debasing myself for Charles.

4.43
21.3k
2
3
5

The Ffitch Nortons Ch. 02

And How I Became a Bisexual Slut

H
4.71
47.2k
8
4
13

Internet Meeting

What I did for Charles.

4.4
31k
6
1
12

The Journey Ch. 02

Sissy's continued journey to submission.

4.28
27.6k
8
3
10

Another Submissive Slut - Ms Shawna

Ms Shawna takes her sissy for a taxi ride.

4.35
37.6k
10
1
13

Caitlin and Mistress Vicky Ch. 03

Caitlin has to be on his best behavior when Chad arrives.

H
4.5
111.9k
41
19
58

Brainwashing for Small Cocks Ch. 01

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

4.29
328.3k
167
48
247
0

I Love My Wife Completely Ch. 02

Continuation of my slut wife cuckolding me.

3.72
141.9k
47
16
74

Birthday Treats Ch. 02

A party means more special treats from more family.

H
4.54
162k
128
12
202

I Love My Wife Completely

Being a slut has both advantages and disadvantages.

4.14
160.5k
106
16
168

Feminized by My Girlfriend Ch. 02

Feminization taken to a whole new level.

4.4
278.3k
140
0
174

Elizabeth: Beginnings of a Sissy

An almost true story of a sissy caught pantied by a sister.

4.32
189k
59
16
86
0

A Sissy's New Daddy

Billie is forced to be a sub-sissy.

4.41
532.4k
434
23
568

A Mistress, a Sissy, and a Slave Ch. 01

Jessica makes Adam and Hailey learn to be sissy and slave.

4.17
103.1k
25
5
48
0

Sophie. Black Master's Pet

Bound to a frame, a Sissy schoolgirl is owned.

4.23
114.9k
43
8
52
0

Hotel Cum Sissy

Closet sissy gets a surprise from bar patron.

4.18
103.3k
27
17
33
0

Black Man One Ch. 16

Demoralized white wimp faces the humiliating truth.

3.83
88.2k
29
16
33

The Session

A visit to a Mistress with a twist.

4.33
35.8k
6
0
8
0

The Journey

Submissive sissy's journey to submission.

4.03
52.5k
9
5
12

Discovering Mistress Sarah's World Pt. 07

More feminization. Joe faces a life changing decision.

H
4.53
63.4k
22
6
33

Magic Panties Ch. 06

The end of the saga, Rachel completes her transformation.

H
4.61
77.1k
25
13
30

Chastity with Ex as Keyholder Ch. 03

Orgasms denied and controlled by ex GF continue.

4.47
160.1k
67
10
95

Alex Keeps Paying His Debts

Alex, after being caught cheating, is punished again...

4.11
80.7k
29
13
41
0

Night One

A recount of my first slut adventure alone.

3.92
75.7k
8
3
10
0

A Downtown Moment

Greg finds an old friend willing to allow him to be Georgia.

H
4.64
81.4k
37
11
45
0

A Visit To The Booths

I visit the booths under direction of my Mistress.

4.24
70.7k
14
8
17
0

Cyber Sissy Ch. 05

The final chapter! Our sissy and his lady face a challenge.

H
4.73
68.3k
33
15
42

Cyber Sissy Ch. 04

She Finally uses her strapon to make him a girl.

H
4.69
104k
38
7
54

Cyber Sissy Ch. 03

Megan prepares her sissy for his deflowering.

H
4.62
94.1k
30
6
39

Cyber Sissy Ch. 02

Sissy is used by his wife while bound.

H
4.53
135.9k
39
17
55

Cyber Sissy Ch. 01

A sissy's wife discovers his penchant for feminization.

4.47
191.7k
134
23
202

Chastity with Ex as Keyholder Ch. 02

Ex continues humiliating me with chastity.

4.31
154.5k
65
9
93
3.94
71.5k
11
1
14

The T-Mobile Dress

A sissy craves the pink satin dress from the T-Mobile Ads.

4.36
28.6k
8
5
13
0

Cindy's Humble Servant Ch. 09

He earns his right to be slave to a proud Chinese woman.

4.45
30.5k
7
4
9

Cindy's Humble Servant Ch. 08

He earns his right to be slave to a proud Chinese woman.

4.35
31.2k
4
1
4

Cindy's Humble Servant Ch. 07

He earns his right to be slave to a proud Chinese woman.

4
21.5k
2
0
2

Cindy's Humble Servant Ch. 06

He earns his right to be slave to a proud Chinese woman.

3.93
20.8k
2
0
2

Cindy's Humble Servant Ch. 05

He earns his right to be slave to a proud Chinese woman.

3.96
21.7k
2
0
3

Cindy's Humble Servant Ch. 04

He earns his right to be slave to a proud Chinese woman.

4.21
21.8k
2
0
7

A Tale of Two Bitches

If it seems too good to be true, it probably is.

3.94
29.1k
3
1
6
0

Cindy's Humble Servant Ch. 03

He earns his right to be slave to a proud Chinese woman.

3.67
25.1k
4
0
5

Caitlin and Mistress Vicky Ch. 02

Poor Caitlin has to deal with the idea of his wife's lover.

H
4.5
115.5k
35
11
49

Cindy's Humble Servant Ch. 02

He earns his right to be slave to a proud Chinese woman.

4.2
41.3k
4
2
5

Sissy's New Toy Ch. 02

A sissy and his girlfriend take panty-time to a new level.

H
4.52
57k
26
10
32

Caitlin and Mistress Vicky

A completely whipped husband is feminized by his wife.

4.34
274.1k
104
18
159

Renee's Training

Nathan is unwillingly trained to become a sissy slave.

0
336.8k
177
72
249
0

My Girlfriend Made Me a Sissy Ch. 03

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

H
4.56
315.2k
183
39
246

Chastity with Ex as Keyholder

Ex discovers secret chastity fetish while dating new BF!

H
4.5
374.2k
333
21
498

Discovering Mistress Sarah's World Pt. 06

Josie experiences his first night out as a 'girl'.

H
4.62
73.6k
17
3
24

Party with Wife and Her Lover

Conned into gay encounter.

4.2
136.5k
83
13
101
0

Another Prison Story

White boy meets black man.

H
4.56
366.4k
243
31
314
0

My Girlfriend Made Me a Sissy Ch. 02

Second part. Jess pushes her control further.

4.49
302.8k
133
18
173

His Sissy Bitch Ch. 02

A boss uses his employee for the job he's truly skilled at.

H
4.6
251k
136
16
148

His Sissy Bitch Ch. 01

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

4.43
398.7k
271
20
367

Robin and Jimmy Olsen - Sissies Ch. 01

Former sidekicks out on dates with hunky superheroes.

4.27
34.7k
26
2
32

My Girlfriend Made Me a Sissy

A guy is transformed into a sissy slut.

4.33
795.5k
349
42
542

We Need a Man in the House

Girlfriend brings a real man home.

4.38
180.3k
126
14
171
0

The Seven Dressing Sins: Pride

My girlfriend's fantasy humbles me.

4.49
96.4k
53
8
61

Sissification

The Vix makes an appearance at a local bar.

4.42
53.7k
23
7
28
0

Trapped and Trained Ch. 18

Candi heads to the Shady Ranch for her new job.

H
4.53
204.4k
92
111
109

My Strapon Fantasy

A girl helps her boyfriend live out his fantasy.

H
4.5
271.8k
144
24
208
0

Black Sissy For White Mistress

White woman strapons sissy black male maid.

3.27
29.3k
3
0
6
0

Black Sissy For White Goddess

White woman strapons black male sissy maid.

2.78
23.5k
1
0
3
0

Black Sissy For White Queen

Black male sissy maid rides white woman strapon.

3.44
25.9k
9
1
11
0

A Panty Boy Confession Ch. 01

Learning she likes guys who dress spurs confession.

4.42
43.5k
11
11
17
0

Selection Day

In a femdom utopia/dystopia, a male's fate is determined.

4.1
63.4k
40
8
59
0

A Sissy's Reward

Pleasing a real man, being a perfect sissy.

4.41
200.4k
78
7
96
0
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