‘crossdresser’ stories

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Active tags
crossdresser 

Category

Laurie's Nightclub Adventure

Laurie gets more than he/she expected at a nightclub.

4.33
39.4k
13
4
17
0

Camming Down the Rabbit Hole Ch. 12

It’s getting very messy, but it's all building to a finale.

H
4.89
39.3k
65
79
76

Transnational

Transvestite is blackmailed by MI6 to do dirty work.

H
4.5
39.2k
20
10
28
0

Morning Glory

A great way to greet the morning.

H
4.59
39.2k
37
4
43
0

The Slut Inside Me

Alex is seduced by his younger brother's friend: a gamer bro.

4.44
39.1k
48
5
61
0

My First Ladyboy

Straight alpha male falls for a sexy Filipino ladyboy.

4.41
39k
28
7
43
0

Skipping Practice

Skipping practice leads to fun in panties.

H
4.69
38.9k
42
11
69
0

A Sissy's Walk in the Park

A walk in the woods becomes a dream come true for a sissy.

H
4.68
38.8k
48
2
70
0

Pretty Chris-tine Ch. 03

Couple go out in public with husband dressed en femme.

H
4.63
38.7k
31
5
37

Expectations be Damned

A shy young man is in for a night of seductive surprises.

H
4.64
38.6k
56
7
87

Wife's Surprise Return with Sexy Guy

Wife unexpectedly returns home to find slutty husband.

4.23
38.6k
30
7
40
0

Made Up

A budding crossdresser meets with an experienced trans woman.

H
4.54
38.4k
28
8
35
0

Holly on the Clock Ch. 02

Holly's still working the Party.

H
4.51
38.4k
8
0
9

Made to Obey Ch. 04

Carl's humiliation continues.

4.39
38.3k
21
9
27

CD Stacy's First Adventure

Crossdresser Stacy embraces her sexual awakening.

H
4.72
38.2k
55
24
58
0

Lady In The House - Reprised Ch. 18

Transvestite prison prostitute Michele continues her saga.

H
4.66
38.1k
18
2
20

A Taste for Bikinis

What feels better than silk? Sharing your secrets.

4.39
38k
23
12
29
0

Daddy's Girl Pt. 01

Becoming a private secretary - and more.

4.37
38k
25
2
44

T-Bar

My roommate convinces me to go to a new bar.

H
4.85
37.8k
95
17
142
0

A New Life

Crossdresser wearing hijab and abaya finds a lover.

4.34
37.7k
13
6
20
0

The Missing Clothes

A voyeuristic view of a crossdresser.

3.79
37.6k
7
1
9
0

Marion Turns Me Round Ch. 06

Loving Femdom: the rode dress traveled.

H
4.73
37.6k
19
11
20

Street Walking Sissy Boy!

A man pimps his homosexual.

4.23
37.5k
15
3
24
0

Important Business Comes Up Ch. 03

Jason lands a big account and gets closer to Dana.

H
4.64
37.5k
10
2
11

Just a Normal Couple

A story of just a 'normal' couple.

H
4.58
37.5k
32
7
46
0

Benny's Secret

A Midwest boy's journey to womanhood and back.

H
4.52
37.4k
9
5
11
0

Crossdresser Crosses Over for Good

Crossdresser's first time with a real man.

4.06
37.4k
7
6
10
0

Candy Gets Found Out

TV's first sexual experience goes wrong and then right!

4.22
37.4k
7
3
9
0

My First Time

My First time having sex as a crossdresser.

4.22
37.3k
15
1
19
0

The Photographer's Trap Ch. 01

The female photographer blackmails a femboy clothes thief.

H
4.54
37.3k
72
16
110

The Acceptance of Cassie Ch. 00 - Prologue

Andy begins to accept his sissy side when he meets Anna.

H
4.68
37.3k
40
11
101

Sissy Sold in Thailand

Eric leaves for vacation, but he may never return the same.

4.17
37.3k
29
8
68

Wifey's Work Becomes Play Pt. 02

Wifey enjoys a Real Man in front of femme cuck hubby.

3.86
37.2k
14
14
18

Mary Becomes a Whore

A tale about making of an crossdresser.

4.23
37.2k
18
5
26
0

It Started As A First Date

A buxom lady ends up being a bondage model.

2.9
37.2k
3
1
6
0

Greengages Ch. 04

The surprises keep on coming.

4.38
37.2k
3
4
6

The Secret

He discovers that a co-worker is a crossdresser.

H
4.55
37.1k
48
26
59
0

Evolution Ch. 02

The first master; my first enslavement.

4.32
37k
11
7
11

Panty Fantasy-Hurricane Kate Ch. 03

A little glimpse into Lin's point of view.

4.14
37k
7
11
7

Caught Fishing in Bra & Panties

Mark finds he likes sucking dick more than fishing.

H
4.6
37k
43
6
49
0

The Car Girl

Bumping into a new friend and a new experience for him.

4.28
36.9k
18
0
23
0

Dan's a Crossdresser Pt. 01

Dan gets a divorce and falls into crossdressing.

4.32
36.9k
43
4
75

Hubby's Sissy Training Day!! 02

Told wife I craved cock, didn't expect this!

4.46
36.9k
30
3
40

Teacher gets Taught Ch. 02

Wife discovers husbands secret.

4.36
36.9k
48
6
73

Daddies Panty Boi Pt. 01

My first panty boi encounter with sexy Daddy...

4.47
36.9k
31
5
46

My First Time as Sara... Pt. 03

Sara and Steve make a fateful decision.

H
4.69
36.8k
25
13
31

A Great Day Off Work

Another Craigslist hookup on a day off from work.

3.97
36.8k
8
2
10
0

Prom? Ch. 05

The fallout from prom, and an encounter with a stranger.

H
4.54
36.7k
41
21
51

Tina And Trucker Bill

A transexual threesome with a trucker.

4.15
36.7k
6
4
9
0

Exotic Escapades Ch. 01

Will Tammy's sexcapades truly make her happy?

3.77
36.7k
6
0
8

Hair Banger's Ball

Wife uses a costume party to dress her husband in drag.

H
4.7
36.6k
76
26
120
0

Boss's New Wife

A crossdresser becomes the boss's new play thing.

H
4.53
36.6k
37
14
74
0

Just a Summer Job Pt. 01

Girls at work have some fun with the new guy.

4.19
36.6k
26
8
34
0

My Valentine

CD Jessica celebrates Valentine's Day.

H
4.68
36.6k
32
14
43
0

Maid to Order

You are given the chance to relax at a special maid cafe!

H
4.59
36.6k
38
4
59
0

The Deal Ch. 01

Shy crossdresser has a laundry room adventure.

4.39
36.4k
35
9
51

Toni in the Park... Again

Sexy Cd likes it rough with two strangers.

4.26
36.4k
5
2
10
0

Nobody Knew

A CD goes out for the first time.

4.22
36.4k
6
10
9
0

Straight to Gay Ch. 04

Nick loses all control for bbc.

H
4.74
36.3k
38
11
67

Rear Naked Choke

A crossdressing sissy boi gets a rough fucking in a booth.

4.38
36.1k
18
3
29
0

The House Sitter

House sitting just took an interesting turn for Francis.

4.27
36.1k
36
11
39
0

Kelly Ch. 02

Jim and Kelly consecrate their newfound relationship.

H
4.53
36.1k
27
9
28

The New Teacher in Town Ch. 01

There's a new English teacher in town.

3.89
36.1k
7
4
7
0

The Locksmith

Fantasy night goes awry, sexual awakening begins.

4.42
36k
48
8
66

A Girls Night with My Wife

I dress to pleasure my wife as her girlfriend.

4.31
35.9k
18
3
28
0

Jolene's Momma Pt. 01

More than one thing to worship.

4.19
35.9k
18
4
44

This that go Bump in the Night

Unwanted intruder takes the Tv in more ways than one.

4.26
35.8k
4
2
9
0

Leah, Locked

Two caged sissies manage to have fun together.

H
4.66
35.8k
54
5
109

Son Becomes Daughter Ch. 01

Son is caught by his mother who turns him into her daughter.

4.36
35.7k
48
16
70

My Favorite Orange Bikini

Sissy getting caught in a bikini.

4.06
35.7k
13
3
21
0

Sissy Sex Dungeon Pt. 01

My weekend as a man's personal sex slave.

H
4.66
35.7k
43
5
81

Backwards in High Heels

The most romantic evening of my life, as man or woman.

4.29
35.6k
15
4
21
0

Horny Sissy Goes to "Heaven!"

A crossdressing sissy finds a new place to do "her" thing!

4.37
35.6k
13
4
21
0

Irish Twins

A Crossdresser becomes his Sister for his Brother-In-law.

H
4.71
35.6k
48
6
81
0

Saturday Night Fun

How I spent a recent Saturday night.

3.62
35.6k
3
3
3
0

So You Want to be a Nurse? Ch. 02

Polly visits Michele to help her dress, sexy evening follows.

H
4.62
35.6k
29
4
30

The Sissy Models

A Daddy-Son modelling weekend and a couple of studs.

H
4.6
35.5k
55
4
74

Inaugural Crossdress Sexfight

The first match in a new kind of league.

4.38
35.5k
22
8
26

Hot Summer Night at Jacques

Young man, closet dresser, hooks up with Veronica at Jacques

H
4.53
35.4k
11
6
15
0

Important Business Comes Up Ch. 04

Jason and Dana's work place heats up and changes.

H
4.61
35.4k
7
4
10

Dave Helps Jason become Jenny

Crossdressing for a college party leads to new experiences.

H
4.81
35.2k
89
9
128
0

A Gender Swap Roleplaying Game

A young couple tries to spice things up with role play games.

H
4.74
35.2k
78
23
137
0
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Active tags
crossdresser
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