Try the free LITEROTICA WEBCAMS!

‘cross dressing’ stories

Active tags
Active tags
cross dressing 

Category

Sort by:
ViewsRatingFavoriteNewest
7 Days30 DaysAll Time

First Time Cuckold Ch. 05

Oscar's humiliation continues.

by Angelscuck in Fetish 12/13/2013
4.19
51.1k
14
1
20

Changes Ch. 05

First time En femme in public with Sarah.

by sublocked in Transgender & Crossdressers 10/03/2015
H
4.69
51k
23
10
29

More Exhibition Fun

Cross-dressing fun.

by beck1306 in Transgender & Crossdressers 09/10/2006
4.06
50.9k
3
1
5
0

A Wife's Surprise

Wife surprises cross dressing husband.

by Aprilsdays in Transgender & Crossdressers 06/26/2019
4.36
50.6k
29
15
38
0

Fender Bender Ch. 05

Vicki rewards the Mechanics.

by SissyAndi in Transgender & Crossdressers 06/12/2010
H
4.59
50.6k
16
7
16

Was He Becoming A Cross Dresser Ch. 06

FINAL: dressing as a woman in secret, how far would he go?

by Alpha2Bravo in Transgender & Crossdressers 08/26/2011
0
50.5k
25
3
26

Putting Myself Through College Ch. 08

18-year-old escort works - this time in a dress.

by RobXXX in Gay Male 09/17/2007
4.27
50.5k
6
5
10

Little Sister Ch. 10

Ralph butt fucks Jean.

by Da_Vida in Transgender & Crossdressers 03/19/2009
H
4.6
50.4k
13
1
15

Alice's New Life Pt. 02

Tessa makes some changes to further create Alice.

by SissyDemi99 in NonConsent/Reluctance 09/11/2020
4.43
50.3k
51
0
68

My Wife's Loving Torture Pt. 01

My wife decides to have fun and push some boundaries.

by Captainskullery in Loving Wives 06/13/2020
3.79
50k
35
0
48
0

Blackmailed into Submission

Blackmailed into submission by my neighbor.

by tzleaze123 in Transgender & Crossdressers 02/17/2019
4.01
49.9k
15
6
27

Jayne's Sexy Skirt Ch. 02

Jayne continues to tease her man.

by Helen_CD_UK in Loving Wives 11/13/2010
4.29
49.9k
7
8
10

Rooming With an Alpha Pt. 02

I become further vulnerable to the whim of a superior roomie.

by nicebottom2007 in Gay Male 09/01/2019
H
4.57
49.7k
73
7
94

Fun With Friends Ch. 05

Davina goes shopping and is humiliated again.

by HighHeeledHoney in Transgender & Crossdressers 11/05/2011
4.49
49.4k
17
3
24

Abbie and Todd

Sister shares a brother's secret and then more.

by storieslou in Incest/Taboo 02/19/2022
0
49.2k
61
0
112

Vacation Suitcase Mixup

Kelly's suitcase is missing and he has to wear girl clothes.

by jackie_em in Transgender & Crossdressers 08/30/2021
H
4.63
49.1k
52
14
79
0

Aunt Em's Legacy

Twins spank each other and masturbate.

by merf68 in Incest/Taboo 08/07/2017
4.26
49.1k
21
2
40
0

Riding the Boss Again

The second time I met the boss dressed as Brianne.

by Brian70 in Transgender & Crossdressers 11/12/2017
H
4.54
49k
27
6
32

Sissy Step-Dad Pt. 01

A step-daughter gets her revenge.

by bmp5708 in NonConsent/Reluctance 01/29/2021
4.21
48.9k
38
3
71

Finding Her Secret Emails Ch. 02

Hubby gets spanked & reads more emails.

by Quietoldie in Transgender & Crossdressers 04/03/2017
4.47
48.6k
20
12
23

Quarter on the Pinball Machine

A Loving Wives tale way beyond sissy.

by JessicaMandella in Loving Wives 09/20/2017
3.83
48.6k
8
31
20
0

Transformations Ch. 03

Joey reverts to his old self.

by zoejoey in Transgender & Crossdressers 03/25/2014
H
4.57
48.4k
46
15
53

A Witch's Love

A witch transforms her husband for love.

by Borntolust in Sci-Fi & Fantasy 11/20/2015
4.36
48.1k
51
6
69
0

The Captain

Wife has sex with ship's captain. His wife controls hubby.

by Quietoldie in Fetish 07/05/2014
4.18
47.9k
22
7
34
0

Sam's Panties Ch. 02

Sam suggests a way for Jean to cuckold her sissy more often.

by Quietoldie in Transgender & Crossdressers 07/25/2017
4.46
47.7k
27
7
36

Nicky Takes Charge Ch. 03

Nicky pushes the bisex and femdom to the next level

by gomorrah in Fetish 04/01/2014
4.47
47.6k
35
5
38

Son Becomes My Gurl Ch. 02

Crossdressing Son Becomes My Special Gurl

by MichiganCuck in Incest/Taboo 03/21/2016
0
47.6k
30
0
42

Discovering Amber Ch. 04

Amber goes on a work trip then returns for a big surprise!

by Ms_Allison in Transgender & Crossdressers 10/05/2018
H
4.68
47.6k
39
10
48

Happy Family Ch. 05

Tiffany finds out more about Andy.

by brooke in Incest/Taboo 10/19/2010
4.46
46.9k
12
0
14

Plaything 01

Jim enters the realm of the slut boy.

by trenchantone in BDSM 02/12/2010
4.48
46.8k
16
3
22
0

March Madness Ch. 08

Stephanie decides if she wants more punishment.

by jbirdman in Transgender & Crossdressers 03/22/2009
H
4.62
46.7k
11
0
14

Sissy Secret Exposed Ch. 01

Wife discovers his secret and suggests a course of action.

by LtBroccoli in Fetish 06/01/2018
4.17
46.7k
31
26
38
0

Perfect Little Slut

CD's fantasy comes true with the help of a trusted friend.

by MindTrip412 in Transgender & Crossdressers 01/27/2018
4.38
46.5k
39
6
55
0

Maid for her Pleasure

But the maid messes up.

by grgy56 in BDSM 12/25/2008
4.08
46.4k
6
1
8
0

Becoming Chrissy

How a dominant Hot Wife transformed her sissy husband.

by HottieOlwen in Fetish 09/02/2021
4.07
46.3k
20
1
61
0

Stepmom and Me Ch. 06

Stepmommy, Daddy, and friends doing sexy things.

by JhMcKn in Incest/Taboo 08/08/2013
4.19
46.3k
40
0
50

Hose and a Hard-On Ch. 02

Alex' threesome with Adam and Lori gets Hot!

by TaraJean in Fetish 03/27/2011
H
4.75
46.3k
31
13
32

Cum On Inn Ch. 01

A traditional bed and breakfast gets a transformation.

by CheriSM in Fetish 06/17/2010
4.32
46.2k
8
2
10

My VideoChat Error Ch 18

Party pt II Shaun(a) is forced to service more men and Emma.

by NaughtyOne88 in NonConsent/Reluctance 01/09/2018
H
4.64
46.1k
23
16
38

The Sissy Department Store Ch. 01

A young sissy is caught and turned out.

by sis_porner in Transgender & Crossdressers 11/02/2020
4.44
46.1k
56
10
90

Little Sister Ch. 06

Denise reveals she is a porn star.

by Da_Vida in Transgender & Crossdressers 03/15/2009
H
4.51
46.1k
19
1
20

A Lingerie Fetish

He puts on a lingerie 'cam show', for his visitors.

by Longfellow in Exhibitionist & Voyeur 09/19/2003
3.38
45.9k
3
1
8
0

The Slave Traders

Couple is forced into sexual slavery.

by jamtby in Transgender & Crossdressers 01/10/2019
4.2
45.8k
45
9
52

Drinking From The Fountain Of Youth

I'm dressed up for a girls' night in, and find a new pee pal.

by conh in Fetish 07/10/2013
4.47
45.6k
15
5
20
0

Promise Not to Judge

What were her daughter and her nephew up to?

by HermesMendoza in Incest/Taboo 01/03/2020
4.18
45.5k
22
3
41
0

Adult Sex Theater

Bisexual father & son find each other.

by oneminute2 in Incest/Taboo 08/12/2021
3.59
45.5k
19
7
52
0

Secret Sissy - Ch. 01

Straight guy becomes a raging sissy.

by jojustcallme in Transgender & Crossdressers 08/27/2023
4.21
45.5k
26
15
71

Sissy Comes Clean

A loving wife helps husband accept his sissy tendencies.

by Cuckyboy3 in Fetish 10/02/2020
3.91
45.4k
17
9
40
0

Lessons in Love

A wife's anniversary surprise.

by Nabla in Erotic Couplings 06/15/2012
4.01
45.4k
6
0
14
0

The Begining

A decent into femdom control.

by Copycat88 in Loving Wives 01/07/2016
4.01
45k
20
47
29
0

The Office Ch. 04

Tom's transformation is almost complete.

by EasilyConfused in Transgender & Crossdressers 01/10/2018
H
4.58
44.8k
22
3
27

Becoming a Gal Friday Pt. 04

Young straight guy becomes a fem servant for two gay bosses.

by Showoff888 in Gay Male 09/14/2014
H
4.57
44.7k
21
2
26

Holiday, Time to Play

Wife & sissy husband make new friends.

by Inspired_life in Loving Wives 01/07/2021
4.39
44.5k
28
0
47
0

The Vicar's Temptation Ch. 01

The Consequences of the Vicar’s Temptation.

by Misslexia in Fetish 12/23/2008
4.2
44.4k
10
0
11

March Madness Ch. 09b

Easter surprises for Stephanie with Miss Robin.

by jbirdman in Transgender & Crossdressers 04/11/2009
H
4.69
44.4k
13
0
17

One Friday Night

Jill's coming out party.

by skinnysailor in Transgender & Crossdressers 07/28/2018
4.48
44.3k
11
5
17

Becoming Brenda's Slave Ch. 02

Brenda gives me an assignment to test my loyalty.

by lorihole in BDSM 08/19/2016
4.22
44.3k
12
1
19

The Club of Fools Ch. 01

A man's hooker's experience gets more costly.

by sublocked in NonConsent/Reluctance 03/20/2015
4.4
44.1k
38
2
57

Consent Ch. 05

Jack starts his slavery "employment" as a trannie model.

by sublocked in Transgender & Crossdressers 01/19/2016
H
4.62
44.1k
31
8
37

Camila and the Halloween party

Camila convinces me to go to a Halloween party dressed up.

by Arrowknee in Transgender & Crossdressers 12/31/2022
H
4.73
43.9k
56
6
99
0

Not a Man Ch. 03

Henry and Tess go shopping.

by rarmons in Transgender & Crossdressers 06/11/2016
H
4.52
43.9k
11
5
14

Panty Moments

How I become a wearer of women’s underwear and love it.

by london_james2010 in Fetish 11/24/2013
4.35
43.7k
11
9
15
0

Doctor's Orders

An intervention changes me from cuckold to a complete sissy.

by eviltwin52 in Gay Male 06/27/2021
4.25
43.6k
42
11
90
0

Being Good in the Bedroom

Jenny discovers Rod's secret passion for lingerie.

by MsTrina in Fetish 01/19/2017
4.41
43.5k
7
3
13
0

Pantyhose and Cum Fetish Pt. 01

Part 1.

by OnTheKinkySide in Fetish 03/26/2019
H
4.55
43.3k
32
13
39
0

Prom? Ch. 03

Anna, Natalie and Mike go to a bar. The tension rises.

by New_Girl_ in Transgender & Crossdressers 07/01/2017
H
4.68
43.3k
56
7
66

Get Lucky & Score On Your Way Home

A twisted essay of twisted logic - except for the maths.

by neonlyte in How To 05/19/2006
0
43.3k
1
16
2
0

Vacation at His Aunt's

His suitcase is lost and he has to dress as a girl.

by jackie_em in Transgender & Crossdressers 05/30/2023
H
4.68
43.3k
55
8
112
0

The Office Ch. 03

Tom begins to adapt to his changes.

by EasilyConfused in Transgender & Crossdressers 09/25/2017
H
4.58
43k
20
1
22

Learning to Crossdress Pt. 03

Seduced by a Beautiful Older Lady.

by crossdressme70 in Transgender & Crossdressers 11/02/2016
H
4.63
42.9k
28
3
36

Not a Man Ch. 02

Tess finds out about Jay's plan.

by rarmons in Transgender & Crossdressers 06/04/2016
H
4.52
42.9k
18
5
23

The Club of Fools Ch. 02

Jason is used as a male prostitute, but dressed as a woman.

by sublocked in Transgender & Crossdressers 04/08/2015
H
4.5
42.8k
17
4
21

The Suitcase Ch. 02

A sissy is given to a new Daddy...

by SissyGeorgina in Transgender & Crossdressers 04/13/2016
4.43
42.8k
24
4
29

Eric Lacroix Ch. 02

Lacroix expands his operation, gang-war ensues.

by markydaysaid in NonConsent/Reluctance 04/14/2014
4.23
42.6k
47
7
56

Summer Job Pt. 02

18 year old virgin's first job as a sex toy.

by Showoff888 in Gay Male 01/06/2016
H
4.61
42.5k
31
5
39

The Perfect Scene

Perfection in Self Bondage can sometimes be Too Perfect.

by sublocked in BDSM 12/03/2014
3.5
42.4k
8
4
25
0

I Feel Like a Woman Ch. 01

What the woman wants.

by grgy56 in Transgender & Crossdressers 01/12/2018
4.44
42.3k
25
4
42

Living Doll Ch. 01

Andrew’s desperate times equals taking desperate measures.

by grgy56 in Transgender & Crossdressers 07/10/2017
4.39
42.2k
40
2
64

Becoming a Gal Friday Pt. 05-06

Young straight guy becomes a fem servant for two gay bosses.

by Showoff888 in Gay Male 10/03/2014
H
4.53
42.2k
13
4
16

Francis Meets a Black Stud Ch. 04

Even more unintended consequences.

by FrancisAlba in Transgender & Crossdressers 11/23/2010
H
4.69
42k
15
2
15

Couples Only: Glory Hole Night Ch. 03

The guys tell their neighbor how their lives changed.

by married40scouple in Transgender & Crossdressers 03/31/2012
H
4.67
41.9k
31
6
36

Submissive Fuck Pig Finds a Dom

A filthy fuck pig finds what it's looking for!

by Cumpup39 in Gay Male 06/17/2021
H
4.63
41.8k
45
4
84

The Lawn Rangers Ch. 13

Halloween party leads to a freaky foursome.

by texaswade in Group Sex 08/14/2010
H
4.63
41.7k
7
6
19

Cody Becomes Chloe Pt. 01

A teen goes on Craigslist and meets Will.

by Southernstud97 in Transgender & Crossdressers 03/19/2015
3.54
41.7k
16
9
21
0

A Merry Christmas Lock In

A close knit group of friends get trapped in Mall...

by Louise69 in Transgender & Crossdressers 12/19/2017
H
4.7
41.6k
68
11
81
0

Vivian's Best Kind of Girlfriend

Cross dresser meets a woman online.

by Eroticalover1968 in Transgender & Crossdressers 05/09/2014
4.42
41.6k
10
5
14

The Body's Abyss Ch. 00

Young sister teaches older brother a thing or two.

by Cassava in Incest/Taboo 09/27/2013
3.32
41.5k
3
4
11

Black Cock Party Ch. 15

Vinny makes me his gal and then gives me a golden shower.

by MarkLazer in Gay Male 06/28/2015
H
4.59
41.4k
42
3
49

Counselling Changed Our Marriage Ch. 03

Locals see me dressed & my training continues.

by Quietoldie in Fetish 12/15/2017
4.41
41.4k
24
12
32

Wedding Day's Coming

Shy male helps sexy dress maker.

by Eroticalover1968 in Transgender & Crossdressers 04/02/2014
4.08
41.3k
10
5
10
0

Joey Finds a New App Ch. 06

Joey starts the weekend with his changed family.

by Daddy_0H in Incest/Taboo 12/17/2021
H
4.67
41.1k
46
2
69

A Sailor's Surprise Ch. 01

A Sailor's Story.

by DianeTG in Transgender & Crossdressers 08/23/2018
4.4
41k
28
5
40

Fender Bender Ch. 07

Vicki and Gary get close.

by SissyAndi in Transgender & Crossdressers 08/31/2010
H
4.67
41k
13
4
13

Comforting Pete

Consoling friend reluctantly agrees to help in other ways.

by WhyNotUs in Transgender & Crossdressers 07/07/2023
H
4.83
40.7k
136
16
211

A Changing Dynamic

Bisexual cuckolding of a feminised man by his girlfriend.

by DingoSphingo in BDSM 01/29/2020
H
4.57
40.6k
43
2
78
0

Little Sister Ch. 11

Denise views Jean's film, then comes home and fucks him.

by Da_Vida in Transgender & Crossdressers 03/20/2009
H
4.69
40.3k
15
4
16
Active tags
Active tags
cross dressing
Separate tags with commas. More info in the FAQ
Related Tags
Show More