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‘sissy’ stories

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The Thorns Upon the Roses Ch. 10

The Long Weekend continues.

by SarahSal in Transgender & Crossdressers 09/28/2023
H
4.81
3.9k
7
4
9

Pretty Little Head

A boy becomes a subby bubble-brained wife (male)!

by dreadknots in Mind Control 09/28/2023
H
4.71
28.9k
72
7
130
0

A Surprise and an Impulse

Johnny came home early and fell asleep on the couch.

by GawknBalk in Transgender & Crossdressers 09/27/2023
H
4.62
10.9k
15
1
27
0

Summer Camp for Naughty Husbands Ch. 02

Gender transformation to be a better husband.

by BriannaGregWriter in Transgender & Crossdressers 09/27/2023
4.2
11.5k
13
5
17

The Origins of Pippa

The tale of how I discovered my kinky side.

by sissyslut_33 in Gay Male 09/26/2023
3.86
5.6k
4
5
9

The Sissy Cashier

I know em when I see em.

by Dis0rdered in Transgender & Crossdressers 09/26/2023
4.29
20.4k
21
10
31
0

A Helping Hand.. and Mouth

I walk in on my step-mom servicing dad, but I cant look away.

by GawknBalk in Incest/Taboo 09/24/2023
4.08
32.3k
40
7
63

The Crush Ch. 02

Sam goes deeper under Jackie's spell. Hallie joins in.

by Frankdrudge2 in Fetish 09/23/2023
4.42
8k
11
3
14

The Thorns Upon the Roses Ch. 08

A visit with Doc, a new plaything, and a night in the woods.

by SarahSal in Transgender & Crossdressers 09/23/2023
H
4.64
5.1k
7
4
8

Catfished by Mistress Zee Ch. 02

Couple take their kink relationship to a new level.

by shawnavinyltv in Transgender & Crossdressers 09/23/2023
H
4.77
9.1k
10
5
17

The Making of a Sissy Pt. 03

Sissy finally taking it to the next step with Opa.

by CharleneCross in Transgender & Crossdressers 09/22/2023
H
4.57
10.2k
12
0
20

Needing Leah Ch. 08

Evening in the school common room. Will punishment follow?

by SerraShades in Transgender & Crossdressers 09/22/2023
4.43
4.9k
6
4
7

A Dream Laid Before Me

Ever since first seeing it, this is all they wanted.

by GawknBalk in Transgender & Crossdressers 09/22/2023
H
4.6
7.5k
8
3
16
0

All Caged Up Pt. 01

Mike is introduced to chastity and temptation.

by JD8hrs in BDSM 09/22/2023
4.46
26k
13
5
46

Latex Sissy: Initiation

Rory's second adventure with a mysterious group.

by RoryRouge in Transgender & Crossdressers 09/22/2023
H
4.77
11k
20
1
41
0

A Birthday Treat, Pt. 03

Emma is shared by Daddy and his friends.

by Bi_Guy18 in Gay Male 09/21/2023
H
4.77
18.2k
23
6
39

Village Life Pt. 03

Getting ready for a night of serving at a swanky Manor house.

by Maidtoplease in Transgender & Crossdressers 09/21/2023
4.31
4k
2
2
6

The Family Pt. 01: Donna Ch. 06

Chris signs his wife away.

by fredStoner in Fetish 09/21/2023
4.31
6.4k
8
4
15

My Tormentor Pt. 01

Sissy cuckold learn to serve his wife's master.

by pervysub4u in Fetish 09/20/2023
4.06
10.7k
11
3
22
0

Life of a Dominant Futanari W2 Ch. 15

The Fifteenth Chapter of the second Week.

by Madjic in Fetish 09/19/2023
H
4.88
4k
4
0
13

Sissy Sammi Surrenders

Blackmailed Sub sissy.

by sissy171 in Transgender & Crossdressers 09/19/2023
H
4.55
25.1k
21
13
42

Cuckolds Regret Ch. 02

Husband regrets convincing his wife to cuckold him.

by drdick69 in Fetish 09/18/2023
4.31
36.4k
34
10
60

Jackson's New Man

Jackson finds a man with unusual taste.

by fun_bobby in Gay Male 09/17/2023
4.45
8.4k
3
0
11
0

Teacher's Pet

Bree runs afoul of the Head Mistress' dress code.

by breexdupuis in BDSM 09/17/2023
4.06
9.1k
7
0
15
0

Needing Leah Ch. 07

Day 2 of classes. A lot is troubling Leah. Can Ellie help?

by SerraShades in Transgender & Crossdressers 09/17/2023
H
4.61
5.8k
5
6
7

One Pair is Not Enough Ch. 02

The slow fade of a straight guy to a sissy has begun.

by jojustcallme in Transgender & Crossdressers 09/15/2023
4.39
25.7k
18
2
26

Predator and Prey Pt. 13

Kitten watches her mother get ass fucked, and sucks pussy!

by tawnysuede in Transgender & Crossdressers 09/15/2023
H
4.81
7.1k
11
22
16

The Making of a Sissy Pt. 02

The journey continues as Opa and C got closer.

by CharleneCross in Transgender & Crossdressers 09/15/2023
4.46
8.7k
9
2
14

Best Friend to Girlfriend Ch. 02

Evan and his best friend continue their naughty weekend.

by Bi_Guy18 in Gay Male 09/14/2023
H
4.75
18k
27
9
39

Mickie and Laurie Pt. 19

Mickie has a final surprise for Laurie, and Laurie gets news.

by SissyBoiLaurie in Transgender & Crossdressers 09/12/2023
H
4.57
4.1k
7
13
10

Mickie and Laurie Pt. 18

Laurie shows off her new hair at the club and to Jamal.

by SissyBoiLaurie in Transgender & Crossdressers 09/11/2023
H
4.74
3.2k
4
2
5

Megan's Rules Pt. 02

Megan continues to dominate, punish, and feminize.

by sososubby in Fetish 09/11/2023
H
4.65
25k
16
9
23

College Chronicles Ep. 18 Pt. 02

College Freshman Sami goes to a rock show.

by Smutwriter238 in Transgender & Crossdressers 09/09/2023
H
4.8
6.6k
17
12
22

Willing to do Anything Ch. 02

Nate is signing a contract to spend 1 year as a trans woman.

by LittlestSissy in Transgender & Crossdressers 09/08/2023
H
4.71
31.3k
52
7
67

Tammy Takes Control

Tammy begins to introduce Mike to pegging.

by JD8hrs in BDSM 09/08/2023
4.31
20.6k
6
3
22

My Girlfriend is Way Too Friendly Ch. 04

Lisa and Sam have a date night, So does Horse.

by Tosshhh_ in Fetish 09/08/2023
4.42
18.1k
19
4
39

Jim Wagner Pt. 02

Jim discovers more about his parents and angels.

by sensualcaring in Transgender & Crossdressers 09/08/2023
H
4.83
4.2k
14
10
16

From Mexico with Love

A conservative wife's desires unleashed while in Mexico.

by BeccaSpade in Fetish 09/08/2023
3.93
12.9k
13
2
34
0

Bound By Blackmail Ch. 17

After an eventful ride home, Dafni and Brady have words.

by Brady018 in NonConsent/Reluctance 09/08/2023
4.35
8.1k
0
9
6

Daddy's Experiment

Sissy submits to dark social experiment.

by Sjen451 in Transgender & Crossdressers 09/07/2023
4.22
14.6k
12
3
30
0

Village Life Pt. 02

A Shopping trip with a difference.

by Maidtoplease in Transgender & Crossdressers 09/07/2023
H
4.88
6.4k
4
2
10

Your New Shoulder Devil Pt. 02

Rose plots to corrupt Angelina, Domi plots to seduce Dolly.

by ErinMaura in Transgender & Crossdressers 09/07/2023
H
4.88
4.2k
4
4
8

A Key for a Discount

What a girl will do for a cute outfit!

by RoryRouge in Transgender & Crossdressers 09/06/2023
H
4.61
16.2k
24
8
47
0

Mickie and Laurie Pt. 17

A consequential appointment, and Mickie surprises Laurie.

by SissyBoiLaurie in Transgender & Crossdressers 09/06/2023
H
4.62
3k
5
2
8

The Perfect Storm

A conservative wife turned slut finds husbands cuckold porn.

by BeccaSpade in Loving Wives 09/06/2023
3.66
43.3k
59
2
126
0

From Soccer to Sucker Pt. 11

Jake's fall continues.

by Fibaro in Transgender & Crossdressers 09/05/2023
4.31
11.3k
13
4
18

Megan's Rules Pt. 01

A young man returns home and becomes a sub to his stepmother.

by sososubby in Fetish 09/05/2023
4.41
31.6k
50
8
86

Mickie and Laurie Pt. 16

Laurie has an exam, and finds out what Mickie was up to.

by SissyBoiLaurie in Transgender & Crossdressers 09/05/2023
H
4.58
3.4k
3
2
6

Mickie and Laurie Pt. 15

Laurie starts recovering from her attack.

by SissyBoiLaurie in Transgender & Crossdressers 09/03/2023
4.37
2.3k
3
5
4

Sander on a Summer Vacation Ch. 04

Humiliation only deepens, aunt finds out.

by shadow_83 in Transgender & Crossdressers 09/03/2023
4.36
12.4k
12
6
23

Sissy Sold in Thailand Pt. 02

Eric tried an escape with his new friend.

by SissyLovesWriting in Transgender & Crossdressers 09/03/2023
3.93
11.4k
7
4
10

Needing Leah Ch. 06

Classes begin for our girl in disguise. Trouble lies ahead.

by SerraShades in Transgender & Crossdressers 09/03/2023
4.49
7k
7
10
11

The Rise of Rachel Price T-Girl Pt. 41

Levant takes his revenge for Rachel's last infidelity.

by racheprice in Transgender & Crossdressers 09/02/2023
H
4.84
2.6k
4
10
6

Sander on a Summer Vacation Ch. 03

Hanna testing Sander's limits.

by shadow_83 in Transgender & Crossdressers 09/02/2023
H
4.59
12.6k
7
2
11

Sissy and the Dean

The story of a nancy boy at college.

by Whippet_Darling in Transgender & Crossdressers 09/02/2023
H
4.62
9.4k
12
0
16
0

Sensory Depravation

Sissy's world is silent and dark.

by skinnysailor in BDSM 09/02/2023
4.46
7.4k
1
1
6
0

Boi Finds Daddy - #4

Boi's story continues as he finds a black daddy.

by BoiBlackcinder in Gay Male 09/01/2023
H
4.51
15.2k
10
3
16

Exposed by My Own Hubris Pt. 02

Sissy goes to adult bookstore to meet her blackmailer.

by njcaptionlover in Transgender & Crossdressers 09/01/2023
4.31
10.9k
21
2
29

Festival Transformation

Elizabeth turns Dan into Dani while at a music festival.

by sissicherri in Transgender & Crossdressers 09/01/2023
H
4.72
35.4k
88
20
153
0

Mickie and Laurie Pt. 14

Laurie experiences an unfortunate encounter.

by SissyBoiLaurie in Transgender & Crossdressers 09/01/2023
4.07
3k
2
7
4

Life of a Dominant Futanari W2 Ch. 14

This is the Fourteenth Chapter of the Second week.

by Madjic in Fetish 09/01/2023
H
4.58
3.4k
1
1
6

Where Do I Begin? Ch. 01

Young man gets all his desires fulfilled with an older man.

by tarantula_type in Transgender & Crossdressers 08/31/2023
H
4.66
12.9k
34
8
44
0

Predator and Prey Pt. 12b

Luis takes Kitten for another makeover, and then a makeout!

by tawnysuede in Transgender & Crossdressers 08/30/2023
H
4.85
6.2k
14
12
19

Sissy Son Sucks Drunk Dad Ch. 05

Mom returns home and sees what I’ve become.

by Sjen451 in Incest/Taboo 08/30/2023
4.17
9.6k
19
1
26

White Boy Discovers BBC Ch. 04

Cole's time at college changes him.

by OverLookerKing in Gay Male 08/30/2023
H
4.71
20.1k
31
4
39

Mickie and Laurie Pt. 13

Laurie goes out in public as a woman, twice.

by SissyBoiLaurie in Transgender & Crossdressers 08/30/2023
H
4.74
3.5k
2
1
4

How Did He Know? Pt. 04

Under Trish's spell...until the boyz arrive.

by CDJamieFLA in Transgender & Crossdressers 08/28/2023
H
4.78
5.8k
13
4
18

Wrecking the Homewrecker Pt. 31

Jasmine gets ready for class.

by Fibaro in Transgender & Crossdressers 08/28/2023
4.37
6.7k
6
3
11

White Boy Discovers BBC Ch. 03

Cole's freshman year of college changes him.

by OverLookerKing in Gay Male 08/27/2023
H
4.66
21.3k
32
7
42

The Rise of Rachel Price T-Girl Pt. 40

Levant gets Rachel back with the perfect gift.

by racheprice in Transgender & Crossdressers 08/27/2023
H
4.69
2.6k
6
12
8

Willing to do anything

A debt costs a man his dignity.

by LittlestSissy in Transgender & Crossdressers 08/27/2023
H
4.55
55.8k
70
11
130

Secret Sissy - Ch. 01

Straight guy becomes a raging sissy.

by jojustcallme in Transgender & Crossdressers 08/27/2023
4.2
44.8k
26
15
72

Mickie and Laurie Pt. 11

Mickie and Laurie record a video.

by SissyBoiLaurie in Transgender & Crossdressers 08/25/2023
4.49
5.7k
7
1
10

Village Life Pt. 01

Events after we've left the farm.

by Maidtoplease in Transgender & Crossdressers 08/25/2023
4.13
6.5k
6
0
15

On-Call Relief Administrator Pt. 04

My men force my purpose up my ass and down my throat.

by eviltwin52 in Transgender & Crossdressers 08/25/2023
H
4.71
5.1k
7
1
15

Peter Goes Gay Sub for Daddy Ch. 06

A surprise development for sissy Petey.

by ibsentorvald in Fetish 08/24/2023
4.04
5.6k
6
2
9

Weekend of Submission Ch. 03

Boi is captured and abused by racist biker gang.

by BoiBlackcinder in Gay Male 08/24/2023
4.29
11.1k
10
3
12

A Sissy Success

A service to help sissies live a new life gets a new client.

by fantasycreation in Transgender & Crossdressers 08/23/2023
4.48
13.2k
18
2
30
0

How Did He Know? Pt. 02

I drive Marcus home.

by CDJamieFLA in Transgender & Crossdressers 08/23/2023
H
4.69
9.7k
21
5
24

Exposed by My Own Hubris Pt. 01

Young man is blackmailed into being a full-time sissy.

by njcaptionlover in Transgender & Crossdressers 08/22/2023
H
4.53
22k
28
6
55

Aditi Dominated

Aditi and her month of desperation leads her to a daddy.

by Pleasure_Provider in Mind Control 08/22/2023
3
19.8k
5
1
8
0

Needing Leah Ch. 05

Leah has decided to fight back... will it work?

by SerraShades in Transgender & Crossdressers 08/22/2023
H
4.69
6.5k
7
8
9

Dreams and Reality Intertwine

I open up to Mistress Kate and get a big surprise.

by FemBoyLew in Fetish 08/21/2023
4.37
7.3k
1
2
8
0

How Did He Know? Pt. 01

Closet sissy can't fool black man at the bar.

by CDJamieFLA in Transgender & Crossdressers 08/21/2023
4.48
13.9k
28
6
48

Cucked in Vegas Pt. 04

James takes over completely, we are helpless.

by Biaxial in Fetish 08/21/2023
3.98
7.3k
15
3
20

A Sissy Super Senior Pt. 03

Sebastian starts his sissified routine.

by sophielopes in Transgender & Crossdressers 08/21/2023
H
4.62
9.3k
17
9
21

Chastity Faggot

A chastity faggot that loves to suck cock and eat cum.

by Anal Slave in Fetish 08/19/2023
4.29
10.6k
19
4
37
0

Sander on a Summer Vacation Ch. 02

Sander is forced to be a girl.

by shadow_83 in Transgender & Crossdressers 08/19/2023
4.47
17.1k
10
4
16
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