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‘sissy maid’ stories

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Wife Turns Slut For Husband

He begs his wife to cuckold him.

by Dirty Slut in Loving Wives 10/06/2003
4.47
617.2k
231
9
306

Trapped and Trained Ch. 07

Candi's time as the party maid ends with a demonstration.

by SissyIndy in Transgender & Crossdressers 10/26/2010
H
4.5
239.5k
76
4
99

From a Husband to a Dutiful Sissy Ch. 01

How I went from a loving husband and to a sissy for my wife.

by Sissy_Chantel in Transgender & Crossdressers 06/14/2017
4.41
204k
148
25
241

Finding My Place

He becomes a maid and sex-slave for a dominant couple.

by econut in BDSM 09/01/2014
H
4.63
154.6k
167
17
268

Becoming a Sissy Maid & Slut Vol. 01

How I became a sissy maid & slut to a Master, vol. 1 Ch. 1-3.

by Sissy_Chantel in Transgender & Crossdressers 07/13/2016
4.4
150.8k
126
12
189

From a Husband to a Dutiful Sissy Ch. 02

Chapter 2 of this Mistress wife, sissy husband, lifestyle.

by Sissy_Chantel in Transgender & Crossdressers 06/18/2017
4.3
150.2k
69
22
86

My Sissy Life

This sissy's life. Non-fiction.

by apple2023101 in Transgender & Crossdressers 10/20/2017
3.99
139.4k
50
7
73
0

Mistress's Party Entertainment

Sissy slut used for guests' entertainment.

by sissyapril in Transgender & Crossdressers 10/29/2010
4.14
125.8k
21
11
30
0

Sissy Maid to Be... Ch. 01

Married sissy in for the experience of her life.

by missjennymaid in Transgender & Crossdressers 08/24/2018
4.47
117.4k
79
13
138

Lessons: First Time

Domme gives him more than he bargained for, but just what he needed.

by InYo in Fetish 06/20/2001
4.03
114.8k
10
0
15
0

Collette's Property

Transexual BDSM FFM.

by jencampbell in Transgender & Crossdressers 06/10/2011
4.4
107.9k
33
11
44
0

Sissy Maid Son Pt. 01

A son is forced to become his mother's own sissy maid.

by Robyn228 in Transgender & Crossdressers 07/10/2018
4.28
107.4k
69
5
115

A Houseboy for Mali Ch. 01

A good deed gets an unexpected reward.

by gmikeisbad in Transgender & Crossdressers 07/17/2011
4.17
105.9k
23
3
41

Nikki Goes to College

Nick started college in a school of his mother's choosing.

by Latexsissy69 in Transgender & Crossdressers 01/29/2013
H
4.6
103k
97
16
125

Allyson's First Blowjob

Allyson gives her first blowjob, the first of many.

by sissymaidallyson in Transgender & Crossdressers 01/09/2015
4.01
97.9k
49
9
60
0

Finding My Place Ch. 02

My submission to a dominant couple continues.

by econut in BDSM 10/18/2014
H
4.65
96.2k
69
4
109

Sissy's Decline into a Slut Pt. 01

A journey into sissy slut play then sissy lifestyle.

by Sissy_Chantel in Transgender & Crossdressers 05/14/2017
4.39
94.8k
75
4
112

A Sissy Maid is Born Ch. 01

Storm realises his destiny is Mistress Arrabella.

by catalina_francisco in BDSM 03/09/2005
3.94
87.6k
5
6
9
0

From a Husband to a Dutiful Sissy Ch. 03

My new sissy life to my Mistress wife grow more entrenched.

by Sissy_Chantel in Transgender & Crossdressers 06/23/2017
H
4.51
85k
41
8
55

Mandy's Reward

A sissy maid gets her reward.

by sissymaidrose in Transgender & Crossdressers 08/15/2012
4.4
78k
24
5
42
0

The Entertainment Ch. 01

A sissy maid prepares to entertain his owners' guests.

by econut in Fetish 01/11/2015
4.43
76.8k
54
2
109

The Teamviewer Mature Files

Wimp sissified, blackmailed & transformed for black masters.

by jothesmo in Transgender & Crossdressers 04/19/2019
3.95
76.8k
88
11
135
0

Sissy Gets Punished

Bad sissy learns her lesson.

by MsMorrigan in BDSM 11/19/2015
3.88
75.8k
20
1
26
0

Sissy Maid Son Pt. 02

The sissy maid is getting prepared for her first day.

by Robyn228 in Transgender & Crossdressers 07/14/2018
4.34
74k
31
6
51

From a Husband to a Dutiful Sissy Ch. 04

Chantel moves deeper in life as a sissy including slut work.

by Sissy_Chantel in Transgender & Crossdressers 06/30/2017
H
4.65
72.3k
51
10
62

Becoming a Sissy Maid & Slut Vol. 02

To become a sissy maid and slut to a Master, Vol. 2 Ch. 4-6.

by Sissy_Chantel in Transgender & Crossdressers 07/14/2016
H
4.57
69.8k
44
3
56

Threshold of Desire Ch. 4

Maid service.

by Cuthbert in Fetish 02/09/2002
H
4.5
69.5k
6
1
8

Sissy Chantel, New Reality Ch. 01

Chantel finds sissy fantasy will become her sissy reality.

by Sissy_Chantel in Transgender & Crossdressers 10/14/2016
4.45
64.8k
57
6
79

The Entertainment Ch. 02

Sissy gets used by the inexperienced guests.

by econut in Fetish 01/12/2015
H
4.69
59k
37
4
58

Recruiting of a Sissy Maid Ch. 01

The beginning of of a sissy's recruitment.

by Sissy_Chantel in Transgender & Crossdressers 09/18/2017
4.4
57.9k
46
6
77

Sharing Ch. 02

Domina moves forward in plan to take a lover.

by thetoy in Fetish 03/08/2007
4.29
56.1k
9
3
12

Tasha, My Teenage Mistress Ch. 01

Middle age subs fantasy girl becomes an extreme reality.

by beta_sissy in BDSM 05/06/2021
4.16
54.9k
34
11
75

From a Husband to a Dutiful Sissy Ch. 05

I begin my career in sissy pornography.

by Sissy_Chantel in Transgender & Crossdressers 07/10/2017
H
4.57
54.4k
34
6
44

The Party

Wife's sexual frustration leads to her taking control.

by Quietoldie in Fetish 01/15/2019
4.03
54.3k
38
15
59

The Maid

A bad servant gets humiliated.

by skinnysailor in BDSM 07/12/2017
4.08
54.1k
5
0
14
0

Sissy Maid to Be... Ch. 03

Sissy Jenny discovers Mistress Lizzy's for her.

by missjennymaid in Transgender & Crossdressers 04/04/2019
H
4.57
53.6k
34
16
48

Sissy Maid to Be... Ch. 02

Jenny continues to prepare with Mistress's help.

by missjennymaid in Transgender & Crossdressers 08/30/2018
H
4.61
53.3k
35
10
56

Melody the Maid

Sissy maid Melody gets a surprise from her wife.

by nohbdy88 in Transgender & Crossdressers 08/02/2016
3.99
53k
26
8
36
0

Sissy Maid Son Pt. 03

The sissy maid serves her mother's dinner guests.

by Robyn228 in Transgender & Crossdressers 10/11/2019
4.37
52.9k
31
3
56

Replaced Ch. 04

Maid gets to watch.

by chas19839 in Fetish 05/21/2018
4.33
51.2k
47
21
57

Sissy Awakening Ch. 02

Sissy gets put in chastity and turned into a house maid.

by Torbjornson in Transgender & Crossdressers 10/14/2020
H
4.56
48.2k
27
6
54

Sam's Panties Ch. 02

Sam suggests a way for Jean to cuckold her sissy more often.

by Quietoldie in Transgender & Crossdressers 07/25/2017
4.46
47.5k
27
7
36

Training Her Husband Pt. 02

He's in chastity. Will she expose him.

by trngpet77 in Fetish 07/24/2022
H
4.6
47.4k
31
10
51

Becoming a Sissy Maid & Slut Vol. 03

To become a sissy maid & slut to a Master Vol. 3, Ch. 7-9.

by Sissy_Chantel in Transgender & Crossdressers 07/16/2016
H
4.59
45.8k
27
1
33

Sissy's Decline into a Slut Pt. 02

Part 2 of Sissy Chantel's decline into a sissy lifestyle.

by Sissy_Chantel in Transgender & Crossdressers 05/18/2017
H
4.59
43k
28
2
35

Sissy Awakening Ch. 03

Sissy gets fucked by Sarah's bull and learns about pain.

by Torbjornson in Transgender & Crossdressers 10/15/2020
4.45
43k
24
6
38

Sissy's Decline into a Slut Pt. 04

Part four of Sissy Chantel's decline into a sluts life.

by Sissy_Chantel in Transgender & Crossdressers 05/28/2017
H
4.58
42.9k
15
3
20

Training Her Husband Pt. 06

They've moved quickly. How far will they go.

by trngpet77 in Fetish 10/22/2022
H
4.63
41.7k
38
23
61

Sissy's Decline into a Slut Pt. 03

Part Three of Sissy Chantel's decline into a slut.

by Sissy_Chantel in Transgender & Crossdressers 05/25/2017
4.48
38.1k
25
4
31

Judy's Turn

She picks this week's game.

by skinnysailor in BDSM 10/31/2017
4.1
38k
13
6
27
0

Goddess Monica's Beta Bitches h. 01

She treats her humiliation-hungry beta bitches...

by DonGarciaWallaceIII in BDSM 03/25/2014
2.89
37.7k
8
2
19
0

The Sissy and The Gardener

The Gardener surprises The Sissy.

by snorn in Transgender & Crossdressers 03/28/2017
4.27
36.6k
31
2
43
0

The Replacement

Baroness Maria has many slaves. None are irreplaceable.

by ChristopherDB in BDSM 05/19/2014
4.22
36k
10
0
17
0

Becoming a Sissy Maid & Slut Vol. 05

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

by Sissy_Chantel in Transgender & Crossdressers 07/23/2016
4.48
33k
19
8
22

The Fraternity

Initiation turns out to be more than Andrew expected!

by Dangerdaze in Transgender & Crossdressers 02/11/2022
4.25
32.9k
34
7
61

Sissy Chantel, New Reality Ch. 02

Sissy Chantel serves and services two Dominant men.

by Sissy_Chantel in Transgender & Crossdressers 10/21/2016
4.39
32.7k
14
3
17

Sissy's Decline into a Slut Pt. 05

Continuation of Sissy Chantel's decline into a slut's life.

by Sissy_Chantel in Transgender & Crossdressers 06/02/2017
H
4.58
31.6k
17
2
21

From a Husband to a Dutiful Sissy Ch. 06

Chantel moves on to contracted out maids work.

by Sissy_Chantel in Transgender & Crossdressers 07/18/2017
H
4.61
30.9k
20
5
24

My Father, The Maid Ch. 02

Oliver's father's humiliation continues.

by SissyOona in Transgender & Crossdressers 10/26/2018
H
4.6
30.1k
18
8
23

A Misunderstanding Ch. 01

Mom takes advantage of her son's keyholder mix-up.

by pursuedsub in Incest/Taboo 03/16/2024
4.22
29.9k
47
7
105

House Slave

Maid for Mistress.

by sissy171 in Fetish 08/02/2022
4.48
29k
20
5
40

My New Maitresse Ch. 01

Tom caught cheating on wife. May not like wife’s solution.

by Cagedcompliance14 in BDSM 07/03/2020
4.36
28.9k
15
4
36

The Dominatrix Order Pt. 02 Ch. 02 - Cuckold

Sissy Slut cuckold. CBT for Blondie.

by Jwwsmith in Transgender & Crossdressers 01/25/2019
4.19
28.9k
7
0
18

Unexpected Mistress Ch. 02

Debroah finally agrees to dominate her husband.

by Scottt in Fetish 08/29/2020
H
4.51
28.8k
22
10
33

Becoming a Sissy Maid & Slut Vol. 04

More on my sissy journey, this is vol. 4 and will be Ch.10.

by Sissy_Chantel in Transgender & Crossdressers 07/18/2016
H
4.5
28.2k
20
4
21

Becoming a Sissy Maid & Slut Vol. 10

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

by Sissy_Chantel in Transgender & Crossdressers 08/04/2016
H
4.6
27.8k
14
5
22

Sissy's Decline into a Slut Pt. 06

Part 6 of Sissy Chantel's journey into becoming a slut.

by Sissy_Chantel in Transgender & Crossdressers 06/06/2017
H
4.58
27.7k
12
6
16

Becoming a Sissy Maid & Slut Vol. 14

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

by Sissy_Chantel in Transgender & Crossdressers 08/26/2016
4.39
27.5k
11
5
15

Lace and Love Ch. 02

Sissy Alice prepares for her master's return home.

by vaultdweller111 in Transgender & Crossdressers 05/23/2016
4.23
26.8k
10
1
12

And When I Return Ch. 10

Anna gets second chance. Is stripped and "reborn".

by sublocked in Transgender & Crossdressers 02/01/2015
4.49
26.5k
14
2
17

Sissy Chantel, New Reality Ch. 03

Sucking cock, public humiliation and a good butt fuck.

by Sissy_Chantel in Transgender & Crossdressers 10/24/2016
H
4.59
26.1k
14
0
17

Becoming a Sissy Maid & Slut Vol. 06

Becoming a sissy maid & slut, vol. 6, Chapter 12.

by Sissy_Chantel in Transgender & Crossdressers 07/27/2016
4.46
26k
18
1
25

The Fraternity Pt. 02

Andrews first day as house sissy!

by Dangerdaze in Transgender & Crossdressers 02/12/2022
4.32
25.2k
22
2
35

Becoming a Sissy Maid & Slut Vol. 07

More becoming a sissy maid & slut, vol. 7 Chapter 13.

by Sissy_Chantel in Transgender & Crossdressers 07/29/2016
H
4.54
25.2k
14
1
18

Lace and Love Ch. 03

Jake returns home and is greeted by Sissy Alice.

by vaultdweller111 in Transgender & Crossdressers 05/25/2016
4.21
24.5k
9
1
12

My Father, The Maid Ch. 03

Oliver's father has some fun before work.

by SissyOona in Transgender & Crossdressers 12/02/2018
4.48
23.6k
12
13
14

Becoming a Sissy Maid & Slut Vol. 13

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

by Sissy_Chantel in Transgender & Crossdressers 08/17/2016
4.44
23.5k
17
0
19

Mistress Chantel, Tranny Dominatrix Ch. 02

Journey of this Tranny Dominatrix and the men who visit.

by Sissy_Chantel in Transgender & Crossdressers 08/21/2016
4.32
23.5k
6
2
8

Becoming a Sissy Maid & Slut Vol. 08

More becoming a sissy maid & slut, vol. 8 Chapter 14.

by Sissy_Chantel in Transgender & Crossdressers 07/30/2016
H
4.6
23.3k
12
3
17

Recruiting of a Sissy Maid Ch. 02

Chantel, begins her orientation and training.

by Sissy_Chantel in Transgender & Crossdressers 09/20/2017
H
4.58
22.8k
7
3
10

From a Husband to a Dutiful Sissy Ch. 08

Chantel, Helen & Alan Celebrate her role as a transsexual.

by Sissy_Chantel in Transgender & Crossdressers 07/25/2017
H
4.66
22.3k
16
2
23

The Fraternity Pt. 03

House sissy starts to take her role seriously!

by Dangerdaze in Transgender & Crossdressers 02/15/2022
H
4.53
22.1k
25
8
35

Sissy and Missy

A sissy maid and apprentice dominatrix are punished.

by ChristopherDB in BDSM 01/29/2019
4.11
21.8k
9
1
16

Quite An Evening Pt. 01

A cuckolding couple try it for the first time at home.

by sissy_ash_xxx in Transgender & Crossdressers 01/09/2022
4.43
21.5k
21
2
34

Becoming a Sissy Maid & Slut Vol. 12

More becoming a sissy maid and slut Vol. 12 Ch. 21 bonus.

by Sissy_Chantel in Transgender & Crossdressers 08/10/2016
H
4.67
21k
6
0
7

Sissy Chantel, New Reality Ch. 07

My New Start To My Sissy Life.

by Sissy_Chantel in Transgender & Crossdressers 11/22/2016
4.45
20.3k
7
1
11

Dream Hotel Ch. 01

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

by gsdog1 in Novels and Novellas 07/28/2016
3.58
20.3k
3
1
6
0

From a Husband to a Dutiful Sissy Ch. 17

The Wedding and a very Special Night of Love Making.

by Sissy_Chantel in Transgender & Crossdressers 08/22/2017
4.17
19.9k
11
2
14

From a Husband to a Dutiful Sissy Ch. 16

Chantel has her big surgery, true love is shown.

by Sissy_Chantel in Transgender & Crossdressers 08/22/2017
4.16
19.5k
10
3
13

The Sissy Exchange Program Ch. 11

Vikki becomes a full-time sissy.

by wsxzaq110 in Transgender & Crossdressers 11/03/2022
H
4.56
18.8k
15
4
27

From a Husband to a Dutiful Sissy Ch. 09

Chantel, works as a classy t-girl escort now, lots of fun.

by Sissy_Chantel in Transgender & Crossdressers 07/26/2017
H
4.63
18.8k
15
3
18

Becoming a Sissy Maid & Slut Vol. 09

More becoming a sissy maid & slut, vol. 9, Ch. 15 & 16.

by Sissy_Chantel in Transgender & Crossdressers 08/03/2016
H
4.53
18.6k
9
0
11

Recruiting of a Sissy Maid Ch. 03

Chantel arrives at The Jade Maid Club.

by Sissy_Chantel in Transgender & Crossdressers 09/21/2017
H
4.59
18.1k
12
0
18

From a Husband to a Dutiful Sissy Ch. 18

A hot Hawaii Honeymoon and a future together.

by Sissy_Chantel in Transgender & Crossdressers 09/11/2017
4.33
17.9k
15
1
19

Becoming an FLR Servant Ch. 16

Mistress introduces her new sissy maid to the Master.

by FLRServant in BDSM 05/06/2022
H
4.57
17.5k
6
4
15

A Femdom Cuckold's Weekend Pt. 03

Part 3: Mistress Play Date.

by wsxzaq110 in Transgender & Crossdressers 03/14/2022
4.39
17.2k
10
1
29

Becoming an FLR Servant Ch. 12

High Heels, Butt Plug & New Schedule For Sissy.

by FLRServant in BDSM 01/16/2022
H
4.57
17k
7
1
8

The Sissy Department Store Ch. 04

Some dressing and make-up and a three-way.

by sis_porner in Transgender & Crossdressers 11/12/2020
H
4.67
16.9k
15
6
21
12
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