‘cross dressing’ stories

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Active tags
cross dressing 

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The Schoolgirl Outfit Pt. 01

A lonely college kid, a thicc daddy, and a schoolgirl skirt.

NEWH
4.72
10.3k
42
4
60
0

My Female Boss Takes Control Ch. 05

Goddess grants some humiliating relief from my cock cage.

NEWH
4.6
9.2k
11
3
20

Live in Vegas Ch. 07

Emilia fulfills bukkake fantasies of Japanese team.

H
4.62
1.2k
2
1
5

Matchmaker

A college freshman gets a much needed paradigm shift.

H
4.85
9.6k
29
10
52
0

Changing My Sex Attitudes

I discover that my preconceived notions about sex are wrong.

4.06
4.9k
4
7
11
0

My Female Boss Takes Control Ch. 03

Punishment and some new clothes.

H
4.54
12.8k
18
5
36

My First Dominant Girlfriend Ch. 17

John is given an ultimatum and chooses servitude.

H
4.58
9.2k
10
5
21

My First Dominant Girlfriend Ch. 14

John explores more of his feminine side.

H
4.68
7.6k
8
3
14

SimSissy Pt. 10

Sim Sissy is making a forest shoot.

H
4.58
1.5k
1
1
3

Sexual Conundrum

I get help when questioning my sexual identity.

H
4.76
12.4k
25
8
56

Generational Whores Pt. 02

Patti and Linda get their cunts tended to.

4.49
5.1k
3
0
5

The Corruption of David McGuire

David's stay with his mother's widowed friend opens his eyes.

4.39
4.9k
5
0
14
0

Humiliated in Bangkok Ch. 03

Humiliated by an Escort--the humiliation continues, at home.

4.33
9.4k
11
0
17

My First Time in Panties Pt. 02

James gets caught by his sister and becomes a cheerleader.

H
4.74
18.2k
37
7
63

My First Time in Panties Pt. 01

My first time trying on my mom’s panties…more to come!

H
4.68
21.9k
58
7
99

My Robby wanted to be a cuckold

Wife finds out he husband wants to be a cuck.

4.49
20.5k
35
4
65
0

Hotel "Sissy Whores Inn"

Daddy tracks down his runaway son in Sissy Whores hotels.

4.06
3.7k
1
0
6
0

The Captive of a Cougar!

An older woman punishes a young man for staring at her.

4.15
13.2k
16
3
43
0

A Ladyboy Syndrome Ch. 04

He has been turned surely? What a joy.

H
4.76
3.8k
3
0
3

A Ladyboy Syndrome Ch. 03

Yes, he's been turned alright.

4.48
5.1k
4
1
5

Macleish's Biscuits Co. Ch. 02

Between Master and Mistress.

H
4.57
1.3k
1
0
1

Wife Finds the Sissy in me

Wife sets me up with her best friends gay work colleague.

H
4.56
24.2k
72
25
94
0

The Players

Sparks fly when cross-dresser Keith buys a pretty new dress.

4.31
2.7k
3
0
4
0

A Threesome Between Friends

Childhood friends reuite for a Menage-a-Trois.

H
4.74
11.8k
41
2
80
0

A Ladyboy Syndrome Ch. 02

He was turned, wasn't he?

4.27
5k
9
0
13

Julie Goes to a Wedding Pt. 05

Both the Dommes and slaves are publicaly humiliated.

4.47
2.8k
4
4
7

Julie Goes to a Wedding Pt. 03

A sissy dresses "pretty" for the first time.

4.48
4.4k
3
0
5

Bellhop

Bellhop - at your service.

H
4.57
4.5k
4
1
13
0

Gardening Wild Ch. 07

Wife become desperate for sex and gets more than she expects.

H
4.67
4.3k
2
0
3

Miss Alyssa's World Ch. 01

My life changes forever after meeting Miss Alyssa.

H
4.68
22.9k
41
10
97

Gardening Wild Ch. 06

The story continues with Ben becoming Betty. Lisa also finds.

H
4.73
2.9k
2
0
4

Dani Bambi Doll Pt. 01

Dani's begins his transformation into Bambi Doll...

4.47
20.5k
40
3
76

Bambi or Bust Pt. 03

Bambi explores the city and introduces me to Master M.

H
4.75
7.4k
10
3
15

Lisbeth Moon

Lisbeth Moon joins ASS - Agency For Sexual Satisfaction.

H
4.86
4.9k
7
2
25
0

A Simple Life Ch. 72-83

An interesting breakfast and a much needed recharge.

H
4.92
3.4k
12
1
19

Jane's Unusual Second Marriage Ch. 01

I agree to become Jane's slave. She spanks and teases.

H
4.54
7.7k
9
4
30

Gardening Wild Ch. 05

Lisa turns Ben into sex slave with her friend’s help.

H
4.6
4.8k
2
3
3

Taken by a Bear

Cross dresser James gets what he has longed for.

H
4.58
9.8k
9
5
24

Gardening Wild Ch. 04

The story continues with Ben becoming Betty. Lisa also finds.

H
4.81
3.9k
3
0
7

A Queer Formality

A clash of culture at the playhouse. 750 Word Challenge

4
1.1k
2
3
4
0

Meeting Jim

A memory of the first time I met Jim in person.

H
4.57
5.3k
4
3
11
0

My Housekeeper

Roles of house owner and housekeeper are reversed.

H
4.54
9.6k
18
2
33
0

One Last Drag

CD gets a fresh start after breakup - 750 Word Challenge

4.14
3.1k
3
5
4
0

Snowed In Roommates

During a blizzard my roommate discovers my secret.

H
4.74
26.2k
69
4
127

Gardening Wild Ch. 03

Wife enlists help to improve her husband's cleaning.

H
4.52
7.4k
3
0
9

A Gurl in the Making Pt. 01

A young man discovers more than they bargained for.

4.47
16.3k
17
3
47

Boiling the Frog Ch. 02

A look in a mirror reveals a face Scott's never seen before.

H
4.81
6.1k
16
8
24

Bambi or Bust Pt. 02

I found out what Bambi's done to me in the last 2 days...

H
4.66
13.1k
18
2
29

Ken

Mum's boy toy.

4.2
5.4k
5
1
14
0

A New Perspective Ch. 03

Pegging leads to clarity and insight for Leslie.

4.42
6.8k
1
3
6

Bambi or Bust Pt. 01

Hypnotised & bankrupt, how will my alter ego and I survive?

4.48
19.5k
32
4
68

A Reminder

A teacher performs remotely for Mistress in public bathroom.

H
4.5
4.1k
3
1
13
0

Ron and Nadine Ch. 06

Ronni's change is complete.

H
4.67
3.6k
4
0
7

Boiling the Frog Ch. 01

A woman in black drags Scott into self-exploration.

H
4.66
14.4k
30
9
64

Gardening Wild Ch. 02

Husband learns how to become his neighbour's cleaner.

4.39
8k
6
2
10

The 39 Year Old Virgin

A promise to lose my virginity on my bday has a catch.

H
4.73
10k
25
5
39
0

Life in a Whorehouse Pt. 10

Julie demonstrates her cock sucking skills.

4
3.1k
4
0
9

My Judge Fantasy

Judge helps a man explore his feminine side.

4.25
6.9k
3
0
11
0

Lost Suitcase Adventure Pt. 03

Jessica's Plan - Jesse moves in - Worlds collide.

H
4.7
9.7k
20
3
38

After 13 Years of Marriage

Wife dominates husband to save marriage.

3.78
22.7k
28
18
68
0

Lost Suitcase Adventure - Pt. 02

The fun continues and Jesse makes a choice.

H
4.82
14.8k
39
6
66

A Simple Life Ch. 60-71

Fun and games with friends followed by some fun for two.

H
4.94
4.1k
7
6
14

Becoming My Sister Pt. 09

Aimee’s first public appearance continues…

H
4.77
6.5k
19
2
27

Lost Suitcase Adventure

Lost bag & friend's clothes fit better than her husband's.

H
4.84
38.6k
118
16
196

Well, She Finally Asked Me... Ch. 03

..my wife knows, how'd I get so gay?

H
4.74
10.3k
16
9
30

Deep

Stella digs deep to dominate her bff Max.

4.25
9.2k
3
0
13
0

Sissy Whores Inn Pt. 02

Mistress shows daddy who his son really is... Sissy Whore!

H
4.63
14.8k
25
6
43

Dinner Parties with a Difference

Smashing a set of plates leads to sexual slavery.

4.22
5.6k
1
2
9
0

Joey Finds a New App Ch. 57

Joey starts another school week off with a bang.... or two.

H
4.59
8.5k
17
0
23

Becoming My Sister Pt. 07

Aimee prepares for her first public appearance.

H
4.58
10.5k
23
8
33

Sissy Whores Inn

Daddy tracks down his runaway son in sissy whores hotels.

H
4.55
22.3k
51
8
83

Jamie's Journey Ch. 02

The thrill of becoming Vicki … where will this lead … ?

H
4.76
4.1k
7
1
7

Life in a Whorehouse Pt. 06

A woman wants her "granddaughter" to be trained as a sissy.

H
4.52
5.4k
4
5
13

My First Blowjob, But I'm not Gay Ch. 11

Wife outs Stevie to girlfriends, dresses him and drops him.

H
4.51
8.6k
12
5
19

Halloween Weekend 2023 Pt. 03

Gina finally finishes her slutty weekend!

H
4.59
8.2k
4
2
12

Becoming My Sister Pt. 06

‘Aimee’ goes further down the rabbit hole...

H
4.75
13.7k
27
3
37

Fire shows the way

Fire shows the way to a new existence.

4.32
2.9k
0
1
3
0

Christmas Party, Don't Try Too Hard

Too much effort in a project can have its share of problems.

4.14
4.9k
4
1
9
0

Becoming My Sister Pt. 05

Things take an unexpected turn for ‘Aimee’…

H
4.74
16.7k
30
6
46

Big Cock Boss Pt. 02 - Intern

Prequel - Alex's virginity is taken by a sexy crossdresser.

H
4.63
11k
28
2
51
Active tags
Active tags
cross dressing
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