‘sissy’ stories

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sissy 

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Never Bet with Your Ego Ch. 02

Paul's day of reckoning comes.

3.66
48.8k
23
24
31

Truth and Lies

A Daddy confronts a neighbor with a truth.

4.43
41.1k
28
8
35
0

The Sissy Grade

A college professor and a student...a student with a secret.

4.32
43.5k
23
1
30
0

Being My Roommate's Sissy Pt. 01

A sissy has a failed first date and gets humiliated.

4.22
155.8k
104
6
164

The Good Samaritan

A friendly gesture leads to more for a horny Daddy...

4.47
28.5k
17
0
20
0

Helping Jess Pt. 05

Getting to know Jess better and the 1st checkup.

4.46
39.2k
16
2
23

Sisters and Brothers

A Daddy finds out that her Brother is her sister as well...

4.44
27k
24
1
29
0

Fetish Club

Rachel takes timid John to a Fetish Club for the first time.

4.33
30.8k
23
9
29
0

Hypnosissy 02: Becoming a Cum Slut

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

H
4.77
404k
421
55
577

The Birth of a Sissy

How a graduation present turned into a lifelong gift.

H
4.55
93k
79
7
108

Pam's Home

She is the devil...he knows it.

3.37
35.4k
6
8
12
0

How I Became a Crossdresser

Straight married man turned into cock loving slut.

4.34
105k
60
19
76
0

Powerless

A sissy cuckold story.

3.98
134.5k
30
10
53
0

A Cuckold Earns His Horns Pt. 02

Madame, Marc, and Molly take things further.

4.32
45.9k
23
5
27

The Metamorphous Ch. 02

A chance for redemption.

4.49
15.6k
14
5
17

Story of Sissy Blackmail Ch. 01

Actual Story of how I was first discovered and used...

H
4.6
155.3k
136
24
180
0

3 AM: She Finally Comes Home

A sissy's wife returns from her date.

3.88
139.5k
41
19
69
0

A New Life Ch. 04

A sissy's life is rearranged at the whim of his owner.

4.39
45.5k
17
1
18

Helen, my Wife and Cuckoldress

Wife goes Black and feminizes her pathetic hubby.

3.98
125.1k
48
33
73
0

First Time Sissy at the Gloryhole

I wanted to be seen in my frilly things, but I got more.

4.14
113k
37
14
60
0

It Happened in the Panty Aisle

A chance encounter turns him into a cock worshipping sissy.

4.49
157.7k
139
52
183
0

A Cuckold Earns His Horns Pt. 01

Submissive sissy cuckold and wife enjoy a hot bull's talents.

4.29
119.9k
71
20
105

College Loser Ch. 05

Locked in chastity and tormented.

3.29
63.1k
8
12
16

When Paul Met Jane

Jay turns in Jane and Paul finds out.

4.47
22.9k
18
4
21
0

I am Number Four

New sissy finds his calling.

H
4.73
77.8k
147
22
190
0

An Evening Stroll

Guy pushes his kinky limits and gets taken much further.

4.46
50k
24
5
28
0

Sissy Lauren Pt. 02

Sissy Lauren continues her journey and trains a new sissy.

H
4.56
39.6k
28
2
36

Sara becomes The Bride

One of my admirers makes my wedding night dreams come true.

4.46
65.3k
38
11
54
0

One of the Girls

Eric unwittingly takes a job as a shemale porn actor.

4.42
99.6k
118
10
155

A New Life Ch. 03

Part Three of a look back at a sissy's life and missteps.

4.03
34.3k
14
0
15

Doll House - The Salon Pt. 02

Sami's initial transformation is completed at the Salon!

H
4.56
86.2k
41
17
52

Andre Finds Love Pt. 03

The mystery of Joanie's death is solved.

4.06
14.1k
2
2
7

A Sissy Fairy Tale

A brave prince frees a sissy princess from a curse.

H
4.69
50.4k
68
11
91
0

Sissy Brainwashing

I had no idea sissy brainwashing was real!

4.28
193k
112
14
174

Hypnosissy 01: Becoming a Cocksucker

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

H
4.76
839.8k
1.1k
210
1.7k

Adult Arcade Sissy

A young man becomes a woman, AND a whore.

H
4.5
91k
82
8
102
0

My First Time as Sara... Pt. 05

Sara takes her first steps to becoming the coquette she is.

H
4.67
30.7k
31
11
37

Turned into a Sissy

Pegging by girlfriend made me crave a real dick.

4.49
189.1k
139
24
205
0

My First Time as Sara... Pt. 04

I start to fulfill my own cravings and desires.

H
4.62
32.5k
26
6
29

So You Want to be a Nurse? Ch. 08

Transvestite nurse is forced to suck and fuck.

H
4.67
28.8k
19
4
23

Letters from my Mistress 01

My Mistress describes our next encounter...

H
4.53
16k
2
4
7
0

My First Time as Sara... Pt. 03

Sara and Steve make a fateful decision.

H
4.69
37k
25
13
31

Letter from Toledo

He let his wife find him a Chastity Keyholder!

3.81
32.7k
11
2
19
0

Cell Block Sissy

A young married inmate go all the way to the wild side.

4.07
77.7k
43
5
59
0

It Could Be Worse Ch. 05

Leon takes control.

4.43
33.6k
28
7
40

A New Life Ch. 02

Part Two of a story about Cinnamon's new life as a toy.

4.18
54.2k
16
1
17

James' Story Ch. 01

Follow James on his story from average loser to sissy god.

3.96
40.3k
24
6
31
0

Turning Points: The First Spanking

A small man and a Dominant Woman.

4.22
29.3k
14
4
18
0

Observations of Buttermilk Falls

Cy, the slaveboy and his dommes!

2.8
15.9k
4
0
7
0

My First Time as Sara... Pt. 02

Steve takes me for the first time and I find out who I am.

H
4.66
54.2k
46
11
51

Letter From Hobson Bend

Can Lionel take being stapled to the floor by his dick?

3
17.5k
3
2
10
0

Celeste's Chuckles

Allowing an orgasm can be tricky for the slave!

3.52
26.3k
8
2
13
0

My First Time as Sara... Pt. 01

This is the story of how I became the girl Sara.

H
4.61
97.6k
98
31
131

The Gynecomastia Kid Ch. 01

With help Nick becomes Nikki after hit by gynecomastia.

4.19
72k
32
7
55

Sissy Lauren Pt. 01

Sissy Lauren begins her prison journey.

4.37
74.5k
52
6
71

The Chaste Crusader

A superhero is in chastity to a super-villainess!

4
22.8k
11
3
18
0

Break Down

A Sissy repays a Good Samaritan.

4.29
30.8k
14
4
18
0

For Their Pleasure Pt. 02

Mr. Grant explains all and makes his move on Alexis.

H
4.65
41.9k
33
6
35

Celeste's Great Adventure

Taking your submissive hubby and your BF to the beach!

4.07
41.1k
16
2
27
0

Celeste's Little Game

She ups things in Ted's training!

3.95
23.9k
7
1
15
0

The Pincushion

A dominant wife gets evil ideas!

3.31
49.9k
6
0
16
0

Letter from Turkey Thicket

Husband training in the Heartlands!

3.59
18.7k
2
3
5
0

Adversity in Buttermilk Falls

Slaveboy Blume is mystified by his dominant wife!

3.97
32k
4
0
11
0

Stan to Stella Pt. 01

Like any story, the beginning for Stella formerly Stan...

4.45
29.2k
18
5
25
0

EE EDGER

EE edges when he can't go to a dominatrix!

3.5
20.4k
5
2
9
0

The Humiliation

Birdie realizes college girls are terrifying!

2.16
34.5k
3
1
9
0

Intruded and Blackmailed

Secret inexperienced sissy gets caught and blackmailed.

3.99
106.5k
20
7
35
0

Mummie's Chauffer

the characters from "Mummie's Hair" and more femdom!

3.08
23.2k
2
3
8
0

Spalding and The Cheerleader

Poor College boy, dommed by Mom!

3.32
47.1k
14
3
27
0

Adventures in Buttermilk Falls

Isaiah gets a new chance with Mistress Bootsie!

2.83
15.6k
3
0
7
0

Doctor Knows Best Ch. 02

Boi gets in deep with his therapy...

4.18
32.5k
12
5
16

Doctor Knows Best Ch. 01

Recluse gets a new therapist... and so it begins.

4.14
47.8k
14
5
23

Indulging His Fantasy

A wife decides her husband would make a good maid.

4.49
87.5k
60
22
90
0

Doll House - The Salon Pt. 01

Sam begins his transformation to fit his new position...

4.36
131.8k
58
13
87

Pillow Fight

An all Sissy slumber party is interrupted by 5 men.

4.14
33.3k
29
6
32
0

Decisions in Buttermilk Falls

He didn't know what he'd get with Miss Thelma!

3.75
14.8k
6
0
8
0

Feminized by a Black Thug

Closeted sissy gets turned out.

4.34
232.1k
181
20
251
0

A Quiet Dinner in Buttermilk Falls

Dinner with your dominant wife can be tricky in a restaurant.

4
29.3k
6
4
14
0

A Weekend with Master Hans

Master Hans loves those recalcitrant husbands!

3.61
43.7k
8
4
12
0

Visions in Buttermilk Falls

Turning an unsuspecting graduate student into a slave-pig!

3.67
35.7k
5
0
9
0

Meditations in Buttermilk Falls

He turned his life over to Mistress Blythe!

3.29
11.5k
0
1
2
0

The Support Group

Men in chastity have a discussion!

3.72
19.7k
3
1
9
0

Happy Days in Buttermilk Falls!

It's always good to have a support group...

3.57
11.9k
2
0
9
0

Living Large in Buttermilk Falls!

Mistress Bootsie knows how to train her husband!

3.92
22.8k
3
0
7
0

Slave Spalding

When he turned 19, he became Mom's slave!

3.73
51k
22
3
43
0

Teasing My Husband

She's unfaithful and quite cruel.

3.44
103.5k
20
6
38
0

Mistress Del!

She's a unique Goddess!

3.2
21.4k
3
1
9

Jocko Trains Colin

Male Master, submissive husband, happy wife!

3.45
32.7k
8
0
11
0

Dominant Housekeeper

Miss Spargrove keeps her couple in line!

4.05
56.1k
19
3
30
0

Ask Medusa

Medusa is the guru of the dominant wife!

3.48
15.7k
3
0
6
0

Gideon's Drama

Gideon at sixty, is still his sister's submissive!

3.96
15.2k
3
2
8
0

The Amazon

She loves her little slaveboy.

3.5
29.4k
12
1
19
0

The Hairdresser

Breezy lives it up!

4
12.5k
00
4
0

Alan And The Doctor Ch. 01

Doctor finds solution to Alan's sexual problems with wife.

4.44
105.5k
72
10
103

Mum's Adult Slave Son!

Mummie rules her adult slave kids!

3.35
79.4k
28
9
53
0

Marigold Tells the Truth

She is a Domme to Fear!

2.78
13.9k
1
6
6
0
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