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‘sissy maid’ stories

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From a Husband to a Dutiful Sissy Ch. 15

Chantel lovingly tells Mikel what she wants.

by Sissy_Chantel in Transgender & Crossdressers 08/11/2017
4.06
12.4k
11
0
14

Lawyer2Maid Ch. 01

Brutal cuckolding of arrogant lawyer turned maid.

by ChivalrousCuck in Fetish 05/07/2024
3.63
8.2k
11
0
21

Mrs. McGregor's Tawse Ch. 02

Stuart meets the tawse.

by MarkKane in Novels and Novellas 01/06/2022
4.49
12.2k
11
5
15

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
27.6k
11
5
15

From a Husband to a Dutiful Sissy Ch. 10

Chantel meets Jack and things are great between them.

by Sissy_Chantel in Transgender & Crossdressers 07/31/2017
4.44
14.6k
11
1
14

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
20k
11
2
14

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
114.9k
10
0
15
0

Lace and Love Ch. 02

Sissy Alice prepares for her master's return home.

by vaultdweller111 in Transgender & Crossdressers 05/23/2016
4.23
26.9k
10
1
12

Sissy Chantel, New Reality Ch. 04

Another Hookup with Master, Chantel's life begins to change.

by Sissy_Chantel in Transgender & Crossdressers 11/01/2016
H
4.55
15.6k
10
1
12

A Femdom Cuckold's Weekend Pt. 03

Part 3: Mistress Play Date.

by wsxzaq110 in Transgender & Crossdressers 03/14/2022
4.4
17.4k
10
1
29

The Replacement

Baroness Maria has many slaves. None are irreplaceable.

by ChristopherDB in BDSM 05/19/2014
4.22
36.1k
10
0
17
0

The Birth of a Mistress Ch. 04

Nicole and Jamie bring it all to a new level!

by Scottt in Fetish 05/23/2021
H
4.57
16.1k
10
3
17

Mistress Jennifer Ch. 03

Mistress Jennifer's control deepens with a friend's help.

by dangletron in Mind Control 08/18/2023
4
12.5k
9
2
23

Sharing Ch. 02

Domina moves forward in plan to take a lover.

by thetoy in Fetish 03/08/2007
4.29
56.2k
9
3
12

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
4.54
18.7k
9
0
11

Sissy Chantel, New Reality Ch. 08

Moving on with my life at 'The Agency'.

by Sissy_Chantel in Transgender & Crossdressers 11/27/2016
4.39
11.4k
9
2
10

Sissy and Missy

A sissy maid and apprentice dominatrix are punished.

by ChristopherDB in BDSM 01/29/2019
4.13
21.9k
9
1
16

Lace and Love Ch. 03

Jake returns home and is greeted by Sissy Alice.

by vaultdweller111 in Transgender & Crossdressers 05/25/2016
4.21
24.6k
9
1
12

Str8 Turn Out Ch. 10: Sissymaid to Bride

Chrissy works as a sissy maid & dreams of her wedding day.

by Humiliater in Transgender & Crossdressers 06/17/2023
H
4.64
13k
9
3
12

Goddess Monica's Beta Bitches h. 01

She treats her humiliation-hungry beta bitches...

by DonGarciaWallaceIII in BDSM 03/25/2014
2.89
37.8k
8
2
19
0

Recruiting of a Sissy Maid Ch. 02

Chantel, begins her orientation and training.

by Sissy_Chantel in Transgender & Crossdressers 09/20/2017
H
4.57
23k
7
3
10

Recruiting of a Sissy Maid Ch. 04

Continuing with Chantel's first day at The Jade Maid Club.

by Sissy_Chantel in Transgender & Crossdressers 09/26/2017
4.48
14.3k
7
1
9

Becoming an FLR Servant Ch. 12

High Heels, Butt Plug & New Schedule For Sissy.

by FLRServant in BDSM 01/16/2022
H
4.57
17.3k
7
1
9

Becoming an FLR Servant Ch. 11

Mistress buys Richard high heels & a butt plug

by FLRServant in BDSM 01/15/2022
4.43
14.9k
7
0
13

Making of Bambi Ch. 08

Bambi gets a new job.

by asiansissysub in Transgender & Crossdressers 02/25/2024
H
4.75
8.8k
7
4
14

The Question

Pain or pleasure? What will Dave choose?

by ChasteFantasist in BDSM 06/03/2021
4.19
12.7k
6
0
23
0

Threshold of Desire Ch. 4

Maid service.

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

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

Mrs. McGregor's Tawse Ch. 22

The Wedding. Branded. The sissy slave maid.

by MarkKane in Novels and Novellas 02/05/2022
4.27
7.5k
6
3
8

Becoming an FLR Servant Ch. 16

Mistress introduces her new sissy maid to the Master.

by FLRServant in BDSM 05/06/2022
H
4.58
17.7k
6
4
16

Intervention Ch. 02 - Party Games

Luke and Julie become Lucy and Juicy for Magda's coven.

by KrisCherita in Mind Control 09/01/2023
4.4
6.9k
6
1
10

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
23.6k
6
2
8

The Maid

A bad servant gets humiliated.

by skinnysailor in BDSM 07/12/2017
4.08
54.3k
5
0
14
0

The Dinner Party Pt. 02

The first guests are about to arrive.

by Stephaniethemaid in Fetish 07/13/2023
4.42
8.8k
5
1
8

Linda's Wife

She controls Linda's problems.

by skinnysailor in BDSM 03/20/2023
4.26
11.8k
5
0
12
0

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

Becoming an FLR Servant Ch. 13

Richard is given his new schedule as Mistress' sissy maid.

by FLRServant in BDSM 01/30/2022
H
4.55
13.6k
5
1
9

S(m)ister Wife Pt. 03

Tourist is kidnapped to be a Sister Wife and maid.

by leeanna19 in Transgender & Crossdressers 02/14/2023
H
4.51
14.5k
4
3
9
0

Mistress Chantel, Tranny Dominatrix Ch. 05

Chantel & Kerri meet for the partnership & fun at dinner

by Sissy_Chantel in Transgender & Crossdressers 09/04/2016
4.13
9.2k
4
3
5

Recruiting of a Sissy Maid Ch. 11

Chantel plays sexy like with staff and with her love Carl.

by Sissy_Chantel in Transgender & Crossdressers 11/07/2017
H
4.61
8.6k
4
0
6

Home Truths

How sissification saves a marriage.

by angelusirae in BDSM 11/14/2022
3.95
15k
4
3
15
0

The Dominatrix Order Pt. 05 Ch. 04

Conclusion Book 5

by Jwwsmith in Fetish 05/29/2019
4.37
11.2k
3
3
5

Recruiting of a Sissy Maid Ch. 14

A wonderful night in Hollywood ends very special.

by Sissy_Chantel in Transgender & Crossdressers 11/30/2017
H
4.55
7.9k
3
1
5

Becoming an FLR Servant Ch. 08

Orgasms and Bath Ritual For Mistress.

by FLRServant in BDSM 12/06/2021
4.29
17k
3
2
5

Sehnsucht Ch. 07: Horace

The disturbed man-boy gets into things he shouldn't.

by ladythisbe in Novels and Novellas 05/10/2018
H
4.53
5.1k
3
0
4

Lawyer2Maid Ch. 02

Brutal cuckolding of arrogant lawyer turned maid.

by ChivalrousCuck in Fetish 05/12/2024
NEW
4
5.8k
3
1
9

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
20.4k
3
1
6
0

The Dinner Party Pt. 01

A sissy maid discovers that he must cook & serve at a party.

by Stephaniethemaid in Novels and Novellas 07/08/2023
3.88
7k
2
0
5

Recruiting of a Sissy Maid Ch. 12

Chantel's first night as the club's new t-girl Dominarix.

by Sissy_Chantel in Transgender & Crossdressers 11/16/2017
H
4.54
10.2k
2
1
4

Chivalry is on Life Support Ch. 33

Cuckolding and emasculation of Medieval Lit professor.

by ChivalrousCuck in BDSM 05/10/2024
3.42
1.6k
2
4
2

Weekend service Ch. 01

First you break it.

by skinnysailor in BDSM 07/30/2023
4.13
7.3k
2
0
8

Sehnsucht Ch. 12: The Party

An unforgettable private party for the Mistress is held.

by ladythisbe in Novels and Novellas 11/09/2018
4
5.7k
1
0
1

Sensory Depravation

Sissy's world is silent and dark.

by skinnysailor in BDSM 09/02/2023
4.46
7.6k
1
1
7
0

Sissy and Missy Pt. 02

A sissy maid plots revenge against a dominatrix in training.

by ChristopherDB in BDSM 07/15/2020
4.44
7.6k
1
4
5

Mistress Chantel, Tranny Dominatrix Ch. 14

Wedding plans, a guys Stag and a Gals Staggette.

by Sissy_Chantel in Transgender & Crossdressers 10/11/2016
4.67
8.7k
1
0
2

Mrs. McGregor's Tawse Ch. 20

Suzanne's training continues.

by MarkKane in Novels and Novellas 02/03/2022
4.38
4.3k
1
0
3

Mrs. McGregor's Tawse Ch. 21

Aunt Mo finishes with Suzanne. A visit to the Nunnery. Home.

by MarkKane in Novels and Novellas 02/04/2022
4.33
3.9k
0
2
0

Meow!

Legislation hasn't kept up with technology late 21st century.

by skinnysailor in Sci-Fi & Fantasy 06/19/2023
4
3k
00
4
0
12
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