‘sissy’ stories

Active tags
Active tags
sissy 

Category

One of the Girls

Eric unwittingly takes a job as a shemale porn actor.

4.42
99.5k
117
10
154

A New Life Ch. 03

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

4.03
34.2k
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
14k
2
2
6

A Sissy Fairy Tale

A brave prince frees a sissy princess from a curse.

H
4.69
50.4k
67
11
90
0

Sissy Brainwashing

I had no idea sissy brainwashing was real!

4.28
192.7k
112
14
175

Hypnosissy 01: Becoming a Cocksucker

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

H
4.76
836.7k
1.1k
210
1.6k

Adult Arcade Sissy

A young man becomes a woman, AND a whore.

H
4.5
90.9k
82
8
102
0

My First Time as Sara... Pt. 05

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

H
4.68
30.6k
31
11
37

Turned into a Sissy

Pegging by girlfriend made me crave a real dick.

4.49
188.8k
139
24
205
0

My First Time as Sara... Pt. 04

I start to fulfill my own cravings and desires.

H
4.62
32.4k
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
15.9k
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
77.6k
43
5
59
0

It Could Be Worse Ch. 05

Leon takes control.

4.43
33.6k
28
7
39

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
4.65
54.1k
46
11
51

Letter From Hobson Bend

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

3
17.4k
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
97.4k
98
31
131

The Gynecomastia Kid Ch. 01

With help Nick becomes Nikki after hit by gynecomastia.

4.19
71.9k
32
7
55

Sissy Lauren Pt. 01

Sissy Lauren begins her prison journey.

4.36
74.4k
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
23.8k
7
1
14
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
10
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
8
0

Intruded and Blackmailed

Secret inexperienced sissy gets caught and blackmailed.

3.99
106.4k
20
7
35
0

Mummie's Chauffer

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

3.08
23.2k
2
3
7
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
32.4k
12
5
16

Doctor Knows Best Ch. 01

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

4.14
47.7k
14
5
23

Indulging His Fantasy

A wife decides her husband would make a good maid.

4.49
87.4k
60
22
90
0

Doll House - The Salon Pt. 01

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

4.36
131.7k
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.

4.33
231.6k
181
20
252
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
35.6k
5
0
8
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
50.9k
22
3
42
0

Teasing My Husband

She's unfaithful and quite cruel.

3.44
103.4k
19
6
37
0

Mistress Del!

She's a unique Goddess!

3.2
21.3k
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
18
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
105.4k
72
10
103

Mum's Adult Slave Son!

Mummie rules her adult slave kids!

3.35
79.3k
27
9
52
0

Marigold Tells the Truth

She is a Domme to Fear!

2.78
13.9k
1
6
5
0

Evilmommie's Little Sperm Eater

She is a dominant wife who knows how to do it!

3.7
50.8k
14
2
20
0

My Accidental Orgy

A Transwoman, hunting for a mate, stumbles into an orgy.

3.9
25k
17
6
23
0

Mistress Ivy

The best Keyholder Ever!

2.63
25.8k
5
2
18

Master's Boy

Master writes to slave's Mistress.

3.57
17.6k
1
3
8
0

Letter From Tacoma

A Submissive Ringmaster!

2.75
9k
1
0
3
0

Letter from Teehan Creek

A few words from Mistress Felicity.

4.33
9.7k
00
1
0

Julie's Triumph

She is happily chastizing a big shot.

3.83
22.8k
7
0
10
0

Dolly's Python

His Master became a Mistress-transgender wise!

4.41
22.7k
10
0
18
0

Trials of Timothy

Timothy is an unfortunate submissive!

3.73
32.8k
2
0
11
0

My Mistress is My Wife Ch. 02

A husband and wife dive deeper into their new found fun.

4.35
54.7k
22
4
30

Cruel Mistress Carnation

Carni is really the bee's knees as a Domme!

3.95
23.2k
8
0
14
0

Tremplin's Pain

Tremplin Duddingstone, wrists and ankles bound...

3.25
13k
2
0
5
0

Slave Chavis

He is ruled by Miss Hooks!

3.64
20.8k
2
0
7
0

The Chastity Cube

Mistress Santiva's happy family!

3.18
30.7k
7
1
20
0

More than just a Glory Hole Ch. 01

A man trying to get quick release is forced to submit.

4.41
129.3k
115
28
184
0

Black Femdom for Black Gentlemen

Black mistress makes black Bull fuck black sissy.

3.6
23.3k
11
2
17

Obedience Training

It's tough being locked up down there!

3.76
52.5k
10
2
22
0

Mistress Sage

She dominates all the men in the area!

3.44
20.6k
8
3
13

Kysia Thinks It Over

She is cruel but to be kind!

2.94
21.2k
2
1
10
0

A Day at the Beach

Danielle's day at the beach leads to "her" first time.

4.07
46.2k
11
10
15
0

It's not All About Her

Sissy is set up and sucks his first cock.

H
4.55
72.4k
56
13
76
0

Generations of Slaveboys

Sub males through out years!

3.27
22.4k
5
0
10
0

JoeBob, Submissive

Can he find the right Domme?

3.5
10.2k
1
1
6
0
1...4950515253...60
Active tags
Active tags
sissy
Separate tags with commas. More info in the FAQ