‘crossdressing’ stories

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crossdressing 

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Mistress Rory

Rory earns her own sub, with a twist from her own Mistress.

4.43
5.9k
5
4
8
0

Dominant Big Beautiful Woman

Reluctantly starting a relationship with an open-minded BBW.

4.1
18.9k
11
3
27

KInky Secretary, Jane's Punishment

Kinky Crossdressed Secretary and Mistress punish Jane.

4.32
5.7k
2
0
8

Kidnapped

Rory dreams of servitude, but does it match reality?

4.32
15.4k
17
1
33
0

3 Days Being a Woman

Spending 72 straight hours as a woman.

4.08
17.8k
10
6
13
0

My Unexpected Journey Pt. 01

My journey into a life I didn't expect.

4.34
10.5k
8
1
15
0

Losing Control

A new girlfriend explores Rory, slowly gaining more control.

H
4.56
8.9k
9
1
18
0

Choices

Rory meets two Mistresses, controlling her with choices...

H
4.66
8.1k
15
3
23
0

Permission

A devious Mistress teases Rory, needing permission to cum.

H
4.77
6.4k
11
1
21
0

Rory's Glory

Mistress brings Rory to a bar, but it isn't exactly normal.

H
4.52
11.6k
16
6
32
0

One More Night

Rory finds a new Mistress, who asks for just a bit more.

H
4.69
4.9k
9
1
12
0

Happy Family

A couple and their daughter get to know themselves.

3.61
21k
14
7
27
0

The Roommate Pt. 02

Rory's relationship with her roommate deepens, and shifts.

H
4.81
21.1k
21
6
36

Kinky Secretary Bondage Lesson

Mistress and Secretary give a bondage lesson.

4.32
4.8k
2
1
6

The Lingerie Club

My first visit to The Lingerie Club.

H
4.83
40.9k
77
7
129
0

Mistress Watching

Mistress watches Rory intently, as she is used by a stranger.

H
4.54
9.2k
24
1
37
0

Eased In

Rory is a good girl, but can she handle this BIG surprise?

H
4.67
16.1k
17
5
26
0

The Roommate Pt. 01

Rory's new roommate takes on a new role.

H
4.53
31.9k
27
1
56

The Birthday Present

Rory's Mistress needs a birthday present for her husband...

H
4.63
8.7k
6
1
9
0

Rory, the Secretary

Rory finds a job as a secretary, with strict conditions.

H
4.57
24.6k
17
2
26
0

Rory's New Job

Rory's Mistress finds her a new job, with certain perks.

4.44
6.8k
6
1
9
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Coming Home

I prepare myself and await your return. F/m.

4.43
8.1k
3
1
4
0

The Fancy Dress Party Ch. 02

Dani's journey, from unwilling to party animal.

4.06
15.6k
22
22
35

Exposed

Rory is exposed, in more ways than one...

H
4.63
10.4k
11
1
15
0

I Listened

Rory is used by Mistress, but not how she expected...

4.17
5k
4
3
6
0

The Allure

One wrong turn leads to being married to the Mob.

H
4.53
10.8k
13
2
28
0

The Price of Shoes

Rory is given new shoes by her Dom, but at what cost?

H
4.59
6.8k
6
1
11
0

Kinky Secretary Kidnapped Again

Kinky Crossdressed Secretary is kidnapped again, Sort of.

H
4.6
4.3k
3
0
10

Devin Dee Ch. 01

Devin Dee goes to a hunting lodge to trick her old friends.

3.8
3.2k
0
1
2
0

A Bowsette Cosplay

Max's alter ego Roxy comes out of preparing for a Cosplay.

H
4.8
24.7k
54
7
90

Rebecca's Ch. 05

Daniel has to decide if he wants to expand his horizons.

H
4.71
17.7k
16
4
26

Camming Down the Rabbit Hole Ch. 08

Going deeper into the warren has never been so much fun.

H
4.84
19.4k
43
13
54

Kinky Secretary Date Night

Kinky Crossdressed Secretary and Mistress have a Date Night.

4.4
6k
4
0
10

Princess on the Balcony Pt. 03

New BF and job CD starts HRT it's not what she was expecting.

H
4.68
5.7k
8
4
14

Fateful Kiss Pt. 02

The lure of a woman and the lure of women's clothes.

H
4.78
8.8k
9
3
11

The Milking

Left caged for a month, Rory was going to cum. Sort of...

4.39
30.7k
25
5
55
0

Rory's Girlfriend

Rory takes over until she's unlocked. "If" she's unlocked.

H
4.58
13.4k
21
5
38
0

Maybe Next Time, Pet

Rory visits her Mistress for a night of being her good girl.

4.48
6.7k
6
0
12
0

How I Met My Husband Ch. 02

Continuation of the series, John becomes Joanie.

H
4.73
21.1k
25
13
33

Dan's a Crossdresser Pt. 08

This is the Finale, Dan becomes one of the girls.

H
4.64
16.6k
28
6
48

Natural

A male worker has anal sex with another.

3.57
10.8k
1
1
5
0

FLR Couple Introduce Cuckolding

FLR couple introduce cuckolding due to underperforming hubby.

4.01
43.3k
44
8
82
0

Kinky Secretary's Punishment Party

Kinky Crossdressed Secretary and Mistress have a party.

4.07
7k
2
0
5

Maid becomes a Slave to Betty Ch. 02

Betty phones the maid and she signs a six month contract.

4.17
15.7k
7
1
11

My New Life Ch. 03 - Dressing up Bliss

More dressing up and some pain from my new toys.

4.2
6.4k
7
1
9

The Exhibitionist Pt. 02 - Date Night

A date has unexpected consequences.

H
4.5
3.8k
4
1
7

Saturday Night is Date Night Ch. 02

Amy's date is more than she bargained for.

4.48
8.3k
8
2
13

Kinky Secretary Goes Out in Public

Kinky Crossdressed Secretary and Mistress go out on the town.

4.18
5.7k
2
0
3

Six-Month Anniversary

A Crossdresser gets a little sidetracked on her Anniversary.

H
4.55
10.6k
5
2
17
0

A Halloween Love Story Ch. 02

Has it all happened too fast, or will love prevail?

H
4.75
10.7k
23
9
30

Intimate Gifts from Strangers Pt. 01

Cum fetish taken to seedy and depraved new lows.

4.32
10.9k
9
5
24
0

Karnelia

A succubus is cornered on the Day of the Dead.

H
4.7
9.3k
8
4
29
0

Where We Left Off Ch. 10

Chapter 10 of 13. A young soul on a journey to find herself

H
4.6
3.7k
3
1
3

Magic Man - Hotel Encounter

A chance meeting on a business trip leads to new things.

4.25
9.8k
6
7
9
0

Honeymoon Weekend

Crossdresser's first intercourse with a male.

4.41
24.7k
26
6
47
0

Kinky Secretary turns Domme Ch. 02

Kinky Crossdressed Secretary turns Domme 2.

4.35
4.5k
1
0
8

An Unusual Gift Ch. 04

Abby borrows the collar to get revenge.

H
4.66
24.1k
30
7
50

Where We Left Off Ch. 08

Chapter 8 of 13. A young soul on a journey to find herself.

H
4.51
3.8k
3
0
5

Day Date

Brunch with the girls becomes a date with a man.

H
4.75
32.4k
38
18
66
0

Kinky Secretary turns Domme

KInky Secretary turns temporarily Dominant.

4.42
10.4k
2
1
10

A Halloween Love Story

Sam's had a bad week, but the weekend changes everything!

H
4.67
27.1k
38
9
61

Wanted: Maid (Male) Pt. 03

Mistress gets him into a maid uniform.

H
4.63
43.8k
37
3
56
0

The Fancy Dress Party

A husband and wife go to a fancy dress party.

4.13
39k
62
37
86

Hypnosissy 09

Brian begins his feminization journey.

H
4.75
75k
118
25
160

Transdimensional Earbuds Ch. 02

250 years in the future, a MILF was there for Peter.

4.36
3.6k
2
0
6

Incarnate Resorts Pt. 04

A salon makeover with Mia.

4.42
6.8k
7
1
13

Sisters Know Everything

My sister finds out my biggest secret.

H
4.56
86.4k
123
22
234
0

Caught By My Assistant Emily

My assistant finds out about my secret gay sissy CD life.

H
4.64
35k
57
37
99

Kinky Secretary on Vacation Ch. 05

Kinky Crossdressed Secretary and Mistress go home.

H
4.56
4.4k
1
0
3

A Threesome

Abe wants to protect his girlfriend from an ex lover.

4.46
12.8k
11
4
21
0

Hers

His girlfriend likes him feminine. He's hers.

H
4.56
96.3k
103
11
195
0

Peter the Neighbour

A young man and his older neighbour.

H
4.5
66.5k
55
11
78

Kinky Secretary on Vacation Ch. 04

Kinky Secretary and Mistress continue their vacation.

4.37
4.5k
1
0
4

The Junk Draw

2 CDs realize some things are better kept in the junk draw.

H
4.67
10.4k
11
11
15
0

Maid becomes a Slave to Betty Ch. 01

Man dresses as a maid and is sold in a charity auction.

4.31
17k
10
1
25

Fateful Kiss Pt. 01

Unexpectedly kissing a colleague has consequences...

H
4.64
20.7k
28
10
45

Wanted: Maid (Male) Pt. 02

A young man gets familiar with the lady of the house.

H
4.59
43.6k
50
10
69
0

Where We Left Off Ch. 05

Chapter 5 of 13. A young soul on a journey to find herself.

H
4.71
4.6k
6
1
6

Kinky Secretary on Vacation Ch. 03

Kinky Crossdressed Secretary and Mistress go on Vacation.

4.49
6k
3
1
4

Taking the Plunge Bk. 02 Pt. 11

Trisha & D discover new levels to their relationship.

H
4.63
2.8k
2
0
3

Kinky Secretary on Vacation Ch. 02

Kinky Crossdressed Secretary and Mistress go on Vacation.

4.17
6k
3
1
4

Wanted: Maid (Male)

Young man starts a job he isn't quite ready for.

H
4.52
69.2k
80
8
157
0

Charles in Charge Ch. 06

He tried to go straight... failing he dresses as a woman!

H
4.59
7k
10
0
13

A Bride for the Damned

A weekend retreat takes detour into horror.

4.3
12.4k
5
0
12
0

Charles in Charge Ch. 05

Dressed as his sister he seduces her boyfriend!

H
4.7
10.6k
10
1
14

The New Student Ch. 01

Amy is disciplined by her teacher.

4.23
17.1k
11
9
24
0

Cheerleaders and Linebackers

Caught in girlfriends clothes a CD has to show off at party.

H
4.7
30.6k
46
11
77
0

Kinky Secretary on Vacation

Kinky Crossdressed Secretary and Mistress go on Vacation.

4.34
12.5k
9
2
19

What You Let Slip Pt. 02

Jen clues in Steve on what else he might have let slip.

H
4.77
23.5k
29
9
44

Bad Magic Ch. 05

A spell misfires and turns a nerd into a hot babe.

H
4.68
11.1k
11
3
18

The Femboy in the Locker Room

A femboy cheerleader and a alpha football jock fuck.

4.26
55.7k
77
7
141
0
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