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‘cross dressing’ stories

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Ivana Pushing Sissy's Limits

Wearing a dress to a Christmas Party wasn't enough.

by frezrevup in Transgender & Crossdressers 03/14/2013
4.06
102.6k
38
13
48
0

Sister and Brother Ch. 05

Sister brother and cousin continue their orgy.

by brothercd in Incest/Taboo 04/23/2008
4.41
97k
38
9
50

Missing Knickers

Missing knickers lead to her son.

by ukfunguy in Incest/Taboo 11/06/2008
4.17
181.7k
38
13
49
0

Camming Down the Rabbit Hole Ch. 06

New outfits and a trip to the shops with an unexpected bonus.

by Dani_does_Dallas in Transgender & Crossdressers 10/13/2021
H
4.82
19.5k
38
8
42

Stepmom and Me Ch. 04

Playing with my stepmom.

by JhMcKn in Fetish 04/18/2012
4.37
64.8k
37
0
43

Fair Is Fair Ch. 03

Husband finally gets what he deserves, or wants.

by bgdddy_2000 in Transgender & Crossdressers 12/23/2013
H
4.65
67.3k
37
3
42

Dressing up daddy

Dad gets dressed and his first cock.

by mosalan in Incest/Taboo 02/01/2007
4.4
135.3k
37
10
43
0

A Femboy's First Encounter Pt. 02

Femboy gets to spend a night with his new friend.

by Sissyfanboy in Anal 09/08/2021
H
4.58
39.1k
37
4
61

The Live-in Maid Ch. 01

Married man loses everything due to crossdressing.

by Quietoldie in Transgender & Crossdressers 01/07/2018
4.21
53.7k
37
11
61

Loving Wife Ch. 03

He accepts his submissive feminine role.

by Agena in Transgender & Crossdressers 10/25/2005
H
4.56
200.3k
37
17
43

A Fantasy about Learning & Growing

A couple goes on vacation and both of them grow up.

by TexasFarmBoy in Novels and Novellas 08/22/2015
4.47
39.9k
37
21
51
0

Bob Dresses for Halloween

With wife's blessing, Bob ventures into cross-dressing.

by LaffWithMe in Fetish 07/05/2001
H
4.61
113.9k
36
7
46
0

Bet Gone Wrong

Man has to dress as a woman after losing a bet.

by jackie_em in Transgender & Crossdressers 03/09/2023
4.49
22.1k
36
7
64
0

My Daugherter and Me Pt. 03

Fucking my daughter and family incest.

by JhMcKn in Incest/Taboo 05/25/2015
4.03
53.7k
36
1
47

Andy's Journey Ch. 02

Andy submits to a domineering mother.

by Borntolust in Incest/Taboo 03/21/2015
H
4.58
88.4k
36
5
62

Fraternity Pledge

I told my dad I’d do ANYTHING to get into his fraternity.

by kparc1212 in Transgender & Crossdressers 09/07/2022
H
4.51
24.8k
36
1
59
0

Dani Bambi Doll Pt. 01

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

by CindyCherie in Transgender & Crossdressers 03/20/2024
H
4.52
16.7k
36
3
64

What Goes Around

I married a whore and became one myself.

by eviltwin52 in Gay Male 06/14/2021
4.49
28.6k
36
5
54
0

Was He Becoming A Cross Dresser Ch. 01

Dressing as a woman in secret, how far would he go?

by Alpha2Bravo in Transgender & Crossdressers 05/02/2010
0
107.2k
35
10
44

Dan's Conditioning Ch. 06

Kendra helps Dan learn how to live as Danielle.

by headrush274 in Illustrated 09/24/2022
H
4.5
129.1k
35
17
51

Oh, Mr King! Pt. 03

Mr King begins Julian's transformation.

by exaucer in Transgender & Crossdressers 01/21/2018
H
4.73
35.9k
35
0
42

Fair Is Fair Ch. 02

Couple continue their sexual journey.

by bgdddy_2000 in Fetish 11/14/2013
H
4.69
61.3k
35
2
41

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

Her Tutu was Too Much

Mandy asks paul to stand in for his sister at the ballet.

by Devilsoctane in Transgender & Crossdressers 11/24/2023
H
4.62
12.9k
35
2
76

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
49.9k
35
0
48
0

Rent Relief Pt. 01

Landlord takes payment from desperate young twink.

by AshleyFinch in NonConsent/Reluctance 03/16/2021
3.77
29.7k
35
2
59
0

Oh, Mr King! Pt. 06

Mr King's deception continues.

by exaucer in Transgender & Crossdressers 04/10/2018
H
4.67
21.4k
35
0
40

When Joe Met Jane

This party, things worked out differently.

by mollycactus in Transgender & Crossdressers 10/11/2018
H
4.72
38.2k
35
11
52
0

Ray Finds a Partner

Mum helps panty boy son find family sex.

by Quietoldie in Transgender & Crossdressers 01/28/2015
4.28
86.1k
35
3
56
0

The Best Day of My Life

Harley's frat gets him a date, but it isn't what he expected.

by HarleyLongshanks in Transgender & Crossdressers 08/06/2020
4.36
25.8k
35
2
46

Halloween is a Night to Let Go

College guy & cross-dressed roommate seduce a coed.

by Mastur in Transgender & Crossdressers 02/19/2007
H
4.5
94.9k
35
0
44
0

The Suitcase Ch. 03

Georgina gets her body mods and a dark secret is revealed...

by SissyGeorgina in Transgender & Crossdressers 04/17/2016
4.42
77.8k
35
8
44

A Threesome Between Friends

Childhood friends reuite for a Menage-a-Trois.

by WhyNotUs in Transgender & Crossdressers 04/16/2024
H
4.75
9.2k
34
2
63
0

The Perfect Handjob

A loving couple deals with a husband's high sex-drive.

by Ricky_writes in Loving Wives 12/28/2005
3.76
280.5k
34
17
48
0

Birthday Present Pt. 05

The next step.

by donnaallure in Transgender & Crossdressers 10/05/2006
H
4.68
103.5k
34
7
44

Changes Ch. 09

Final chapter and the ultimate bondage and submission.

by sublocked in Transgender & Crossdressers 10/25/2015
4.37
55.8k
34
27
43

Dana-girl Ch. 01

Mamma's boy.

by betamale08 in Transgender & Crossdressers 01/04/2021
4.29
47.4k
34
3
75

Sister and Brother Ch. 04

Sis and her CD Brother continue adventures.

by brothercd in Incest/Taboo 04/22/2008
4.42
67.7k
34
3
42

Female Boss's Sexual Plaything

She forces him into bra & panties, then ties him to a desk.

by Gizmo86 in BDSM 07/19/2008
3.94
221.2k
34
12
65
0

Kidnapped (A One Week Chronicles)

Crystal may just have gone too far this time...

by Louise69 in Transgender & Crossdressers 09/26/2017
H
4.69
62.9k
34
8
55
0

Danielle's Transformation

He finds himself becoming the woman he wanted to be.

by daniellecdgurl in Transgender & Crossdressers 03/07/2014
3.93
83.7k
34
18
43

Proud To Be A Sissy Ch. 03

He finally learns to enjoy life and find his place.

by Kary_M in Transgender & Crossdressers 05/01/2008
H
4.6
89.7k
34
3
39

Chloe 01

The beginning.

by xDarkAngel0 in Transgender & Crossdressers 01/21/2022
H
4.64
31.9k
33
8
80

Games for Gamers

A lazy gamer gets ticked by his own loving girlfriend.

by LovekittenLK in Transgender & Crossdressers 11/19/2023
4.37
20.9k
33
8
70
0

And When I Return Ch. 14

The climax return of Jason to his wife Jenna.

by sublocked in Transgender & Crossdressers 02/27/2015
H
4.81
37.4k
33
25
35

Corset Club Adventures - New Member

Secret cross dressing sex club revealed.

by TheSexualDeviance in Transgender & Crossdressers 05/31/2020
H
4.69
17.3k
33
0
40
0

My VideoChat Error Ch 05

Denise Goes Deeper.

by NaughtyOne88 in NonConsent/Reluctance 06/01/2016
H
4.68
57.1k
33
8
50

Corrupting The Underwear Thief Pt. 01

I catch the young lad next door stealing my underwear.

by rocketskate in Transgender & Crossdressers 10/25/2022
H
4.72
19.8k
33
15
55
0

The Lingerie Party Guest of Honor

Hubby "dresses up" for wife's lingerie party.

by slipfreak46 in Fetish 01/17/2006
4.38
121.8k
33
11
46
0

Sweetness

An accident sends a man towards a new life and love.

by Tester86 in Transgender & Crossdressers 05/12/2021
H
4.63
30.5k
33
12
50
0

Crossing the Rubicon

Feminization of a man by his wife.

by sublocked in Transgender & Crossdressers 02/20/2012
4.12
154.9k
32
19
49
0

Down The Rabbit Hole

Follow Alex as he finally lives out his feminisation fantasy.

by TasksForSubs in Transgender & Crossdressers 01/20/2023
H
4.74
20.6k
32
9
61

Lost Suitcase Adventure - Pt. 02

The fun continues and Jesse makes a choice.

by WhyNotUs in Transgender & Crossdressers 01/21/2024
H
4.85
11.6k
32
5
46

It Could Be Worse Ch. 04

It couldn't be better.

by eviltwin52 in Gay Male 03/08/2016
H
4.52
29k
32
7
43

Proud To Be A Sissy Ch. 04

A young man finally learns to enjoy life and find his place.

by Kary_M in Transgender & Crossdressers 04/30/2008
H
4.63
71k
32
3
39

Pantyhose and Cum Fetish Pt. 01

Part 1.

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

The Trophy Bride

True love costs.

by skinnysailor in Transgender & Crossdressers 08/28/2018
4.28
56.5k
32
5
47
0

Sissy Bottom Has a Nite Out Ch. 03

More cross-dressing fun with buddy & wife.

by lostsoul1974 in Gay Male 10/08/2005
4.48
110k
32
7
39

First Time Bi

Going from bi-curious to bisexual.

by f_stop in Transgender & Crossdressers 08/31/2016
4.4
73.4k
32
8
44
0

The Exploits of Cockslut Kelly 03

Waiting for the weekend, Kelly is used in front of co-eds.

by CSK in Transgender & Crossdressers 10/09/2013
H
4.62
56.4k
32
6
37

Sissy Crissi Ch. 04

Crissi wonders what will happen next.

by sissycrissi in Transgender & Crossdressers 07/02/2007
H
4.7
95k
32
19
38

The Other Side of the Window Ch. 04

Continuing with my life.

by EaglesFlyte in Gay Male 05/29/2012
H
4.64
31.6k
31
12
43

Sissy Secret Exposed Ch. 01

Wife discovers his secret and suggests a course of action.

by LtBroccoli in Fetish 06/01/2018
4.17
46.6k
31
26
38
0

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

I Finally Go Clubbing While Dressed

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

by Arrowknee in Transgender & Crossdressers 11/24/2021
H
4.56
18.7k
31
7
44
0

Joey Finds a New App Ch. 15

Joey comes home to a few surprises.

by Daddy_0H in Incest/Taboo 12/28/2021
H
4.58
33k
31
4
51

Brought to My Niece

Secret crossdressing uncle discovered.

by TheDarkCloud in Incest/Taboo 12/03/2019
H
4.53
25.2k
31
7
47

Sissy Crissi Ch. 02

Crissi must now deal with her roommate, Erika.

by sissycrissi in Transgender & Crossdressers 04/18/2007
H
4.65
124.1k
31
11
39

It Could Be Worse Ch. 03

Things can't get any more worse.

by eviltwin52 in Gay Male 03/04/2016
4.32
39k
31
4
43

A Game of HORSE Pt. 03

Brandi takes charge.

by emelle78 in Transgender & Crossdressers 06/11/2021
H
4.74
21.3k
31
9
38

Deflowered Rosa

Sweet crossdressing sissy gets used.

by EmileXXX in Gay Male 11/26/2021
H
4.72
15.1k
31
4
40
0

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

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
41.8k
31
6
36

How I Became A Witches Foot Slave

Kidnapped by three women and turned into a foot slave.

by femdomwriter in Fetish 11/04/2012
4.02
86.4k
31
8
42
0

My Friend Phil's Big Cock

Straight husband seduced by his friend's huge cock.

by roxyblacksissy66 in First Time 10/27/2023
4.39
34.3k
31
5
61
0

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

Signature Required

My first encounter with Jake the delivery driver.

by Brian70 in Transgender & Crossdressers 05/22/2018
4.48
32.4k
30
3
43
0

Frustration of Small Cock

Suffering from a small cock James seeks relief.

by jamtby in Anal 10/13/2018
4.22
70.1k
30
6
45

Horny on Halloween Pt. 02

Chase & Travis can't help but see Ryan in a new light.

by ifiknewthen in Gay Male 01/10/2017
H
4.57
30.8k
30
4
38

Riding the Boss Another Day

Conflicted for our third time together.

by Brian70 in Transgender & Crossdressers 02/14/2018
4.47
37.4k
30
10
35

Cock Servant's Initiation

A young man's path into pleasing stronger men begins.

by nicebottom2007 in Gay Male 09/09/2013
4.45
62.6k
30
9
46
0

Boiling the Frog Ch. 01

A woman in black drags Scott into self-exploration.

by AutumnUnbound in Transgender & Crossdressers 02/06/2024
H
4.66
13.8k
30
9
56

Cum Eating Cocksucker

I learn to eat cum.

by GuyCD in Transgender & Crossdressers 11/20/2015
4.16
117.5k
30
8
46
0

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

How Adam Became a Sissy Fuck Toy

How Adam went from average straight male to sissy bitch.

by SlutFucker510 in Gay Male 11/15/2019
4.03
40.2k
30
5
43
0

A Freshman's Summer Class Ch. 02

College freshman continues learning a new trade for summer.

by CapnSteelBoy in Transgender & Crossdressers 04/28/2020
4.48
33.9k
30
5
36

Joey Finds a New App Ch. 07

Joey and his brother go for make-over!

by Daddy_0H in Transgender & Crossdressers 12/18/2021
H
4.51
27.6k
29
0
43

Cherry Pt. 02

Being neighborly gets me fucked.

by Cirkle7 in NonConsent/Reluctance 11/27/2019
H
4.52
31.6k
29
8
32

Jessica Loses Her Virginity

A crossdresser's coming of age.

by DCJessicaCD in Transgender & Crossdressers 04/16/2007
H
4.54
119.9k
29
13
32
0

I Told Him to Kiss My Ass Pt. 02

I embrace my role as a cock wife and more.

by eviltwin52 in Gay Male 05/23/2021
H
4.6
27.9k
29
5
42

Family Fun Ch. 03

Karen brings her daughter Kathy to heel.

by ElliottEden in Incest/Taboo 08/15/2021
H
4.63
27.1k
29
4
50

Subservient Ch. 03

Angie gets hubby to agree to the unthinkable.

by samuel69 in Fetish 06/14/2010
0
138.9k
29
7
42

Married for Money

Man pays a big price for cheating on his wealthy wife.

by jackie_em in Transgender & Crossdressers 07/23/2022
4.46
32.3k
29
9
59
0

My Little Slut

Sissy boy slut finally gets used by Mistress.

by Sweetblood03 in Fetish 07/26/2012
4.29
89.2k
29
3
36

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

Donna's Sissy

Mark's feminization.

by skinnysailor in Transgender & Crossdressers 01/17/2022
H
4.53
41.2k
29
6
57

Beth Ch. 01

Beth is born.

by ragal2 in Gay Male 01/14/2023
H
4.53
22.4k
29
10
49

Becoming My Sister Pt. 10

Aimee is taken to Jim’s bed…

by fantasy_writer_2023 in Transgender & Crossdressers 01/21/2024
H
4.77
7.6k
29
2
39

Consent Ch. 06

Jackie falls daily deeper into submission and the unknown.

by sublocked in Transgender & Crossdressers 03/07/2016
H
4.52
34.5k
29
2
37

The Sins of the Fathers Ch. 13

First date gets out-of-hand while father chaperones.

by Fatherlyneed in Incest/Taboo 09/03/2016
H
4.53
36.5k
28
8
41
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