‘sissy’ stories

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Active tags
sissy 

Category

Crossdresser's First Anal Orgasm

A cross dresser has their first sissygasm.

4.18
122.2k
59
5
86
0

The Sexy Cuckold Couple Pt. 12

Cuckold Couple Becomes an Owned Couple.

4.48
45.7k
24
1
33

The Sexy Cuckold Couple Pt. 11

Cuckold Couple Becomes an Owned Couple.

4.47
50.4k
25
3
36

The Prostate Exam Pt. 02

How a married guy is turned out as a sissy by his Doctor.

H
4.5
169.2k
95
2
133

The Sexy Cuckold Couple Pt. 09

Cuckold Couple Becomes an Owned Couple.

H
4.5
67.5k
47
5
72

Big Black Cock at the Beach

Writing for an erotic hypno, past induction phase.

4.48
49.7k
28
3
36
0

Unloading in Bristol Ch. 02: Davina

Cuckold sissy and wife continue to be used.

4.21
27.9k
13
2
13

The Therapist

Beta male learns to become a perfect submissive sissy boi.

H
4.56
78.2k
45
9
81
0

The Sexy Cuckold Couple Pt. 08

Cuckold Couple Becomes an Owned Couple.

4.44
48.8k
25
3
38

Unloading in Bristol

Trucker pays a visit to a cuckold sissy and his wife.

4.25
39.8k
33
4
40

The Sexy Cuckold Couple Pt. 07

Cuckold Couple Becomes an Owned Couple.

4.45
71.1k
36
9
62

The Hanky Code Pt. 18

The married guys final trial before his week of work.

4.41
35.5k
19
15
23

The Sexy Cuckold Couple Pt. 04

Cuckold Couple Becomes an Owned Couple.

H
4.5
88.6k
71
5
94

A Little Tied Up... Pt. 03

'Danielle' gets some company in her friend 'Ally'.

4.21
70.4k
11
4
17

The Prostate Exam Pt. 01

Married guy, outed as the anal slut he really is, by his Doc.

H
4.51
256.8k
313
16
481

My Fantasy Journey Pt. 01

A straight man's journey from CD to cum loving slut.

4.39
42.1k
23
6
30

How to Become a Sissy/Cuckold

For husbands wanting change in their marriage.

4.43
156.5k
85
33
125
0

The Sexy Cuckold Couple Pt. 02

Cuckold Couple Becomes an Owned Couple.

4.18
146.3k
100
10
135

Scene from a Dinner Party

A snapshot of the bliss of being a maid.

4.23
46k
15
4
23
0

The Settlement Pt. 02

Complying with the settlement Darlene becomes sissy maid.

4.47
36.1k
27
1
35

The Sexy Cuckold Couple Pt. 01

Cuckold couple becomes an owned couple.

4.32
301.4k
349
16
555

A Little Tied Up... Pt. 02

Mark has some more fun with 'Danielle'.

4.2
90.9k
20
3
28

Mistress Chantel, Tranny Dominatrix Ch. 14

Wedding plans, a guys Stag and a Gals Staggette.

4.67
8.7k
1
0
2

The Ex That Kept Me Pt. 03

What would have happened if your ex didn't let you go.

H
4.61
25.8k
20
1
28

Meating Terry

My first experience with a submissive sissy boy.

4.14
34.3k
16
5
20
0

After the Birthday Party

Kasey meets the woman of his dreams.

4.36
34.8k
24
2
32
0

The Hanky Code Pt. 16

The pig is whored out by his TS Mistress.

H
4.57
35.9k
17
6
21

Sara and Steve... Again

Sara and Steve find each other again...

H
4.6
21.2k
16
3
23
0

Jerkboy Life Ch. 08

Sarah makes him show his panties to a man.

4.43
33.5k
9
0
15

My Bully Owns My Family Ch. 03

Bully turns to Dad, completing ownership of my family.

4.3
228.1k
193
30
285

The Hanky Code Pt. 15

Married sub whored out as gay latex slut by TS Mistress.

H
4.61
46.4k
25
6
33

Mistress Chantel, Tranny Dominatrix Ch. 08

Kerri's first night Domming with me at our Studio.

4.38
8.6k
000

Girly Daddy

Sissy dad supports masculine son in every sense.

4.13
123.7k
107
4
165
0

The Man That Owns Me Ch. 02

A sissy 'girl' has a very good second 'date'.

H
4.54
58.7k
47
6
56

Mistress Chantel, Tranny Dominatrix Ch. 06

Kerri joins the business and we develop a relationship.

4.2
8.7k
4
2
4

Zoey's Basement Transformation Pt. 03

Zoey completes her transformation into an obedient sissy.

H
4.51
94.9k
54
11
78

Jerkboy Life Ch. 03

Facing the reality of fantasy.

4.37
62.1k
26
1
42

Zoey's Basement Transformation Pt. 01

A pathetic young man's transformation begins.

4.39
185.5k
93
7
187

Mistress Chantel, Tranny Dominatrix Ch. 05

Chantel & Kerri meet for the partnership & fun at dinner

4.13
9.3k
4
3
5

Meeting Mommy

A sorry sissy remembers the first time she met her Mommy.

H
4.61
228k
202
16
324
0

Jerkboy Life Ch. 01

Wife reveals husband's secret to her mom.

4.41
139.5k
101
15
174

Mistress Chantel, Tranny Dominatrix Ch. 04

Continuing story, Chantel meets Kerri's friends.

3.84
9.2k
4
0
4

Mistress Chantel, Tranny Dominatrix Ch. 03

Continuing, T-girl, Mistress journey, meets Kerri & more.

4.25
12.4k
8
0
11

Sara Shows Her New Man Self Love

Sara meets an admirer and fulfills his fantasy of watching.

4.46
19.1k
10
4
14
0

Becoming a Sissy Maid & Slut Vol. 14

More becoming a sissy maid & slut vol.14 ch.23

4.39
27.7k
11
5
15

Public Domination

Sissy wimp dominated by Two Dommes in Public.

4.15
48.5k
22
3
38
0

Mistress Chantel, Tranny Dominatrix Ch. 02

Journey of this Tranny Dominatrix and the men who visit.

4.32
23.7k
6
2
8

Becoming a Sissy Maid & Slut Vol. 13

More becoming a sissy maid & slut vol.13 chapter 22.

4.44
23.7k
18
0
20

Writing Erotica For The First Time

A twenty something trans girl decides to write erotica.

3.98
14.6k
6
5
9
0

Mistress Chantel, Tranny Dominatrix Ch. 01

The Journey of this Tranny Dominatrix and the men who visit.

4.02
42.4k
27
0
48

Blackmailed High School Sissy Ch. 02

When two bad girls find out about Max's sissy fetishes.

4.13
183.9k
53
14
78

My First Time Pt. 02

Jessica and Eric define and continue their relationship.

H
4.72
28.8k
33
8
40

Turned into a Sissy Slut Ch. 01

A customer pisses a wiccan off and the revenge is sweet.

4.08
89.3k
63
16
82
0

Drunk Friend to Sissy Slut

Game of Edward 40 Hands turns me into my true slutty self

H
4.58
175k
263
22
378
0

Sex, Drugs and My Neighbour Daddy

My hot neighbour blackmails me into being his little sissy.

4.35
159.4k
122
14
166
0

Cherry's Graduation Party

A sissy celebrates the completion of her training.

4.42
22.5k
17
1
21
0

My First Time

CD Jessica's neighbor becomes her FWB.

H
4.7
76k
77
26
103

Becoming a Sissy Maid & Slut Vol. 11

More becoming a sissy maid & slut, vol.11 Ch.18-19-20.

H
4.82
28.7k
13
4
18

The Birth of a Sissy Pt. 03

House Sitting for Big Daddy.

H
4.57
30.3k
20
2
26

Becoming a Sissy Maid & Slut Vol. 10

More, becoming a sissy maid & slut, vol.10 Chapter 17.

H
4.61
28.1k
14
5
22

One Step Too Far

A sissy is in trouble playing bondage in his sister's room.

H
4.56
69.7k
56
11
99
0

Melody the Maid

Sissy maid Melody gets a surprise from her wife.

3.98
53.4k
26
8
35
0

Dream Hotel Ch. 01

The start to a guy's new life as a sissy maid.

3.58
20.5k
3
1
7
0

Being My Roommate's Sissy Pt. 02

The submissive sissy's story takes a cuckolding turn.

4.39
107.2k
50
9
63

My Innocent Wife Pt. 01

I caught my wife cheating.

3.27
109.7k
50
22
75
0

A Girl And Her Sissy

A girl recounting the feminization of her boyfriend.

4.36
159k
107
13
150
0

Gay Whore Pt. 02

Donny has the night of his life being a whore.

4.11
52.7k
17
5
22

Blackmailed High School Sissy Ch. 01

When two bad girls find out about Max's sissy fetishes.

3.81
227.6k
73
5
161

Becoming a Sissy Maid & Slut Vol. 05

Becoming a Sissy Maid & Slut, Vol.5, Chapter 11.

4.49
33.3k
19
8
22

A Night at the Club Pt. 01

Keyshawn and Dani go to a hot interracial club.

H
4.63
68.5k
78
9
105

Dani's Night Out

A chastised sissy is sent out to satisfy a huge black man.

H
4.65
122.8k
165
10
217
0

Sara Flies the Friendly Skies

Sara becomes a sexy flight attendant and becomes a mile high.

H
4.62
28.2k
19
3
23
0

A New Lover

A wife informs her husband about her new lover.

3.71
102.9k
52
8
65
0

A Slut's Triangle Pt. 04

Ashleigh sucks Kryss’ cock and leaves upset.

4.2
14.8k
3
3
4

A Slut's Triangle Pt. 03

Ashleigh and Kimberly talk about guy problems over a drink.

4.08
16.6k
6
4
6

A Little Tied Up...

Daniel wakes up in an 'interesting' situation.

3.99
136.3k
33
6
59

My Transformation

A story of one person's feminisation.

4.12
94.1k
25
20
37
0

A New Life Ch. 05

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

4
43.4k
12
5
12

Sara's Amazing Night

Sara fulfills one fantasy and in turn fulfills one of hers.

4.46
35.8k
16
4
23
0

Surprise Femdom Next-door

Andy has a crush on his neighbour, but is she all she seems?

4.05
94.5k
46
10
79
0

Sissy BBC Cleaner Pt. 01

The beginnings of a depraved traps humiliation and ecstasy.

4.15
97.2k
58
10
78
0

A Gooner's Tale

The sissyfication and bimbofication of her lover.

3.44
51.3k
20
7
31
0

Turning into His Toy Ch.02

I meet daddy and he lets me choose my fate.

4.23
75.2k
26
7
30

Jamie's Descent Pt. 02

Jamie slips further under Vanessa's control.

H
4.63
45.7k
33
4
38

Turning into His Toy Ch.01

The beginning of how I went from man to a sissy slut.

4.32
111.2k
57
9
73

Black Cock Smoking Sissy Slut

A smoking sissy is on the hunt for black cock.

4.42
70.4k
78
11
94
0

The Diablo Masquerade Pt. 03

Kira gets punished for deceiving Rhonda.

4.36
6k
3
0
5

A Slut's Triangle Pt. 02

Ashleigh's bad luck with Kryss leads to meeting someone new.

4
17.7k
4
3
4

Living Next Door to a Closet Sissy

Peeping Tom turns into a sexy girl for his lesbian neighbor.

4.43
136.9k
52
20
92
0

The Birthday Party

A 30 year old loses his virginity to three men.

H
4.5
69.2k
63
8
80
0

A Slut's Triangle Pt. 01

Kryss fucks Ashleigh and leaves her wanting something more.

4.12
49.3k
35
19
51
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