‘crossdressing’ stories

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Active tags
crossdressing 

Category

The Blue Dress

An unwilling crossdresser gets more than he expected.

4.46
46.5k
37
10
67
0

One Sexy Halloween Costume Pt. 01

I may have over committed to my girlfriend’s costume idea…

H
4.59
75.4k
74
23
150
0

Chloe 02

A return to the house of dreams.

H
4.69
8.6k
12
3
18

Dominant Big Beautiful Woman Pt. 02

Reluctant but wanting her. A perfect woman and sissy.

H
4.55
11.6k
10
6
14

Kinky Secretary Plays Poker

Secretary and friends play bondage poker.

4.1
5.3k
3
0
8

Annie Atwater Ch. 01

Annie tries to seduce Sid C, but runs into problems.

3.89
2.5k
1
0
3
0

A Job to Save His Family

A young man accepts a job at his mother's request.

4.25
55.7k
47
41
89
0

A New York Night

CD Friends enjoy sexual fantasies of all kinds.

4.67
6.5k
3
0
7
0

A Latex Trap Ch. 03

Gwyn and I open up to Amy and Steve

4.41
4.7k
5
1
9

The Wager

A coaxed feminisation story centering on a bet.

H
4.68
42.2k
86
17
140
0

I Love To Love You Baby

It's 1988 and a CD goes on vacation to lose her virginity.

H
4.51
8k
6
4
11
0

The Circle Ch. 01

A middle aged man discovers a voyeur.

4.07
5.4k
0
3
4
0

The Black Book Pt. 02

Allegra finds herself and enjoys it!

4.35
3.5k
5
2
6

Something New: Three's a Party

A double-booking turns into so much more fun.

H
4.57
7.9k
10
1
16

Nikki's Massage Therapy

Anxious gay male receives intimate massage therapy.

H
4.67
16.5k
8
3
22
0

You Are Going To Thank Me

Rory gives away her keys to a friend, who has her own agenda.

4.48
17.3k
23
6
46
0

Sissified Ch. 16

Roxie completes one year in chastity.

H
4.5
28.2k
25
5
40

Taken - Pt. 02

A tale of abduction, transformation, and unlikely salvation.

H
4.51
19.3k
22
2
36

Sissy Maid to Mom and Sister Pt. 04

Nadia (Andy) sets out to clean, but can't get to it.

H
4.64
19.8k
34
4
50

Quite An Evening Pt. 01

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

4.42
21.1k
21
2
34

Taken - Pt. 01

A tale of abduction, transformation, and strange attraction.

H
4.54
33.7k
37
2
77

Coming Home Ch. 01

A young man moves back home and becomes stepmom's sissy.

H
4.5
37k
65
15
97
0

The Acceptance of Cassie Ch. 01

Cassie remembers her first two dicks and thinks of Anna.

4.47
15.7k
25
2
44

Kelli Kneads 01

Rotating game nights has benefits

3.63
4k
2
1
4
0

Santa Rosa Slut

Young sub is femmed by older Dom bears.

4.48
25.5k
37
1
72

Kinky Secretary New Year's Eve

Kinky Secretary and Mistress celebrate New Year's Eve.

H
4.68
4.4k
3
0
8

The Mummy

A submissive gets mummified and fucked.

4.05
15.8k
3
2
18
0

Trapped Little Kitten

Rory finds herself trapped, and exposed more than she knows.

4.25
16.4k
13
6
28
0

Sissified Ch. 12

Sissy gets fucked by a real cock.

H
4.62
37.4k
25
5
39

Aunt Polly's Sister

CD discovers herself with help from her friends and family.

H
4.77
16.7k
21
15
41
0

Sissified Ch. 11

Mom tells Sissy about her trip.

H
4.7
26.9k
18
1
30

My New Gym Buddy Pt. 04

Nice people at the adult shop help me boost my confidence.

H
4.6
12.3k
23
1
36

Max the Maid

Max's master returns home.

4.31
14.3k
6
2
17

A Day on the Water

Mia is invited out for a boat ride by an older man.

H
4.73
25.5k
61
29
84

Sissified Ch. 10

Mom finds out about her sissy son.

H
4.63
35.6k
29
4
49

Sissified Ch. 09

Sissy does a lingerie photoshoot.

H
4.7
23.2k
27
2
41

Sissified Ch. 08

Sissy serves as a maid at mistress's party.

H
4.71
30.7k
25
1
45

My Goddess

Rory meets a woman who would change her life.

H
4.55
11.5k
14
5
34
0

Kinky Secretary in the Dungeon

Kinky Secretary and Mistress tour Linda's dungeon.

H
4.55
5.6k
2
0
5

Fifty-Fifty

A young CD entertains men at parties.

4.03
11.1k
6
0
9
0

Two Hundred Dollars

A therapist and his patient have sex.

H
4.53
12.1k
8
3
15
0

Under Mommy's Control: Enhanced

A Sissy finds a way to relax, and makes a terrible misstep.

H
4.66
48.2k
55
20
115
0

Becoming Chloe

Crossdressing leads to accidental Cuckold with wifey.

4.21
53.2k
68
25
114
0

Only Good thing to cum out in 2020

Girl rediscovers herself in lock down, and her new self.

H
4.62
8.4k
12
5
15
0

The Need

The need to be Rory grows stronger and stronger...

H
4.73
12.3k
10
1
21
0

Madonna: The Girlie Show

A review of Madonna’s naughty tour of 1993.

4.4
2.5k
0000

The Christmas Gaze

Surprise! A crossdresser has a wonderful Christmas Eve.

H
4.64
18.6k
19
13
29
0

Pain & Pleasure

Mistress tests Rory, pushing her further than ever before.

H
4.58
11.9k
14
1
23
0

Hallowiener Pt. 08

Dani finds out, shortcuts can be dangerous, but worth it.

H
4.74
7.7k
20
1
30

Kinky Secretary Christmas Party

Secretary and Mistress host a Christmas Party.

3.9
5.4k
2
0
5

The Black Book Pt. 01

A player gets a taste of his own medicine and loves it.

4.48
9.7k
14
1
22

Tennis Club Pt. 03

Stealing - is bad.

4
3.4k
00
1

Cuckold Hotel Pt. 02

Kylie heads for a humiliating evening.

4.49
31.4k
27
6
41

Tennis Club Pt. 02

Stealing - is bad.

4
5.3k
00
1

Sissy Maid to Mom and Sister Pt. 03

Liz bonds with her mom before her sissy maid brother returns.

H
4.67
32.3k
38
6
72

Blackmailed by Mr. B Ch. 03

Mr. B pulls "Candy" out of school for some filming.

H
4.69
48.5k
54
7
79

Hush

Rory's Mistress denies her with a simple word, over and over.

H
4.53
9k
12
5
23
0

New in New Delhi Ch. 01

A young closeted sissy moves in with two men as part of work.

4.34
8k
4
2
5
0

Pimped: What did I Get Myself Into

A desire of a sissy to be pimped becomes too real.

4.41
19.7k
14
5
22
0

Summer Reunion

An encounter with an old classmate takes an unexpected turn.

H
4.63
44.9k
91
12
166
0

What You Let Slip Pt. 03

Jen takes Steven to a lingerie shop and humiliation ensues.

H
4.68
25.6k
30
21
47

Domme Linda returns

Mistress and Kinky Secretary welcome Linda back.

4.41
6.3k
4
2
5
0

A Pink Christmas in Vermont

A crossdresser's life changes over the course of the holiday.

H
4.76
23.8k
25
14
51
0

Sissy Maid to Mom and Sister Pt. 01

Andy gets caught by his sister in her panties and it's fine.

H
4.58
55.7k
81
12
185

Transmogrification Ch. 02

My slut transition adventures continue.

H
4.6
11.5k
11
0
15

Kinky Secretary Bondage Interview

Mistress and Secretary host a zoom Q and A.

4.2
4.4k
3
0
8

A Weekend Away Ch. 04

Sissy's training continues and she has her first outing.

H
4.61
18.3k
16
8
24

The Client

As an escort, meeting a client leads to unexpected situation.

H
4.6
18.6k
28
4
48

The View From My Cage

An intense evening with my wife and her dominant lover.

H
4.56
34.7k
55
15
104
0

Mistress and Secretary -Therapists

Kinky Secretary and Mistress give relationship advice.

4.2
3.3k
2
1
4
0

My Wife's Fucked up Family Pt. 02: Ho Daddy

Charles serves his kinky sister-in-law and husband.

H
4.53
19.5k
17
5
27

Pushing the Limits Ch. 04 - Fortuity

Sexually Curious Wife meets Crossdressing Husband in Club.

H
4.68
6.9k
9
2
18

Tied Together

Rory is put through an intimate situation with a new friend.

H
4.63
19k
20
5
34
0

Magic Dress - Bryony

A man with no gender issues in a dress.

4.38
9.3k
5
0
13

Lewd Uncle Larry Pt. 02

Uncle Larry pimps Carlos out.

4.48
10.8k
11
0
22

Turnabout Pt. 05

Will their escalating game of “I dare you” go too far?

4.39
11.6k
7
7
15

Rebecca's Ch. 07

Another step in Diana's feminization.

H
4.78
21.6k
20
5
31

Pushing the Limits Ch. 02 - Mariaxx

Richard & his crossdressing brother in law both seeking fun.

4.39
18.6k
15
3
26

Two Weeks Just for You

A wife lets her CD spouse experience marriage to a man.

H
4.69
29.4k
38
23
62
0

The Perfect Holiday Gift

What do you get for the man who has everything?

4.37
26.5k
10
3
16
0

Jessi's Debut

John's first time out as Jessi to an adult book store party.

H
4.53
7.7k
10
7
17
0

Study Group Surprise Pt. 02

James embraces being a femboy.

H
4.78
46.7k
107
18
141

Kinky Secretary Foot Fetish

Kinky Crossdressed Secretary worships feet.

4.39
6.8k
2
1
8

The Test

Two nude men meet up, have sex.

3.97
9.3k
6
4
11
0

Rebecca's Ch. 06

Formerly Daniel, Diana accepts the path to femininity.

H
4.74
20.1k
16
4
26

The Morning

Rory wakes her Mistress after a night of fun.

4.31
5.8k
10
1
16
0

Permanent

Permanent chastity is exciting, but would Rory ask for it?

H
4.53
36.5k
67
11
113
0

The Agency Ch. 14

Michelle returns to the office after a very busy weekend.

H
4.8
11.5k
19
5
28

A Latex Trap Ch. 02: The Follow Up

Mistress Diana begins a new journey for Gwyn and I.

4.41
7.4k
6
1
13

I Finally Go Clubbing While Dressed

I decide to go clubbing as I finally go out while dressed.

H
4.56
18.4k
31
7
43
0

Journal of a Beginning Sissy

Journal entry of my first time shopping.

4.12
7.7k
2
7
6
0

My New Normal

A new cage for Rory, along with a few new rules...

H
4.63
12k
13
3
27
0

Mistress' Little Whore

Rory is readied by her Mistress, but for who?

4.46
7.8k
11
1
18
0
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crossdressing
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