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‘cross dress’ stories

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How I Became a Cheerleader

Guy changes schools, life and sex to fit in.

by DMaster_14 in Transgender & Crossdressers 10/10/2010
H
4.59
335.8k
476
24
617

Feminized by My Girlfriend

The start of how she changed my life.

by Trinni69 in Transgender & Crossdressers 09/21/2011
4.27
584.3k
309
0
440

Owned:Fantasy Becomes Reality

Married white man submits to big black dom boss.

by silkstockingslover in Gay Male 07/30/2011
H
4.64
369.3k
241
43
322
0

How I Became a CD SLUT Cum Junky

True to fact embelished origin of my CD life and cum craving.

by TonyaTV69 in Transgender & Crossdressers 10/11/2010
H
4.67
183.4k
143
16
173

A Beautiful Teacher

A cross dresser runs into his sexy teacher.

by PANTY_FAN in Transgender & Crossdressers 01/09/2019
H
4.67
86k
138
18
191
0

A Dream Cum True

A loving wife cuckolds husband.

by hardnpan in Loving Wives 02/13/2010
0
223.6k
112
33
132
0

His Sissy Bitch Ch. 04

A man's sissy girl is to become his very public little bitch.

by keptsissy in Transgender & Crossdressers 09/03/2011
H
4.57
234.6k
103
11
109

Cleaning the Garage

Helping a neighbor has never been such fun.

by forummj in Transgender & Crossdressers 06/13/2018
H
4.55
58.1k
101
7
116
0

How I Became a CD SLUT Cum Junky Ch. 02

A Halloween party before the gang bang and I get too wild!

by TonyaTV69 in Transgender & Crossdressers 10/12/2010
H
4.77
124.6k
86
12
94

Falling Under Mommy's Spell Pt. 01

A cross dresser and his mother discover their secret sides.

by LittlestSissy in Transgender & Crossdressers 02/21/2023
4.48
60.1k
80
12
180

My Summer as a Girl Pt. 01

College intern is forced to cross dress for grocery money.

by RightButSexy in Transgender & Crossdressers 06/04/2018
H
4.6
79.9k
77
8
109

My Father-In-Law's New Bride Ch. 04

Wife helps daddy with bride's new training.

by regina_allen55 in Transgender & Crossdressers 10/09/2005
4.44
197.3k
74
14
82

How I Became a Cheerleader Ch. 08

Guy changes schools, life and sex to fit in.

by DMaster_14 in Transgender & Crossdressers 03/26/2011
H
4.69
67k
72
18
78

How I Became a Cheerleader Ch. 09

Guy changes schools, life and sex to fit in.

by DMaster_14 in Transgender & Crossdressers 05/21/2011
H
4.69
62.8k
72
8
79

A Very Hard Working Girl

Sexy slut does what she does best, services men.

by keptsissy in Transgender & Crossdressers 02/23/2012
H
4.56
133.3k
67
5
78
0

The Perfect Age Ch. 04

Sissy 'girl' is a virgin no more.

by keptsissy in Transgender & Crossdressers 12/17/2013
H
4.58
109.9k
66
7
76

Hallowiener Pt. 03

When you've been caught red-handed, you just have to pay up.

by forummj in Gay Male 06/06/2018
H
4.72
36.9k
66
6
85

How I Became a Cheerleader Ch. 11

Guy changes schools, life and sex to fit in.

by DMaster_14 in Transgender & Crossdressers 08/28/2011
H
4.75
63.9k
66
5
72

A Favor for My Best Friend Ch. 03

I continue to let my friend use me as a sex toy to avoid dad.

by Verysecret93 in Gay Male 08/01/2013
H
4.52
97k
60
5
73

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
43.6k
56
6
99
0

Adam Loses a Bet Ch. 03

Amy was maid to do it.

by Amy_wants_more in Transgender & Crossdressers 11/06/2020
4.46
69.9k
56
8
70

Cheryl's Revenge

Cheating boyfriend sissified and left cold.

by grgy56 in Transgender & Crossdressers 04/01/2010
4.39
108.7k
54
5
64
0

A Game within a Game Ch. 01

A cross dresser is being set up, but takes revenge.

by doberinca in Transgender & Crossdressers 12/08/2011
H
4.57
81.2k
54
15
75

The Cuckold Husband

Blackmailed into sharing wife with a stranger.

by sexylilthing in Loving Wives 12/01/2020
3.77
54.6k
51
24
79
0

Caramel and Devin

Two Guys Become Girls.

by CaramelBlack in Transgender & Crossdressers 01/13/2018
H
4.65
33.4k
50
10
55

Falling Under Mommy's Spell Pt. 02

Mother decides some changes are in order.

by LittlestSissy in Transgender & Crossdressers 02/24/2023
H
4.61
43.2k
47
16
66

Hit the Button Pt. 01

Loving Couple - Wife helps Hubby live his dream.

by CindyTV in Transgender & Crossdressers 09/18/2022
H
4.68
40.9k
45
25
89

Falling Under Mommy's Spell Pt. 04

Matty gets a reward and Mommy can't stop herself.

by LittlestSissy in Transgender & Crossdressers 04/18/2023
H
4.71
31.1k
45
16
67

The Perfect Age Ch. 05

A girly-boy loses a dirty old man but gains a lover.

by keptsissy in Transgender & Crossdressers 12/28/2014
H
4.55
66.8k
44
5
52

The Perfect Age Ch. 06

A sissy 'girl' meets her first real lover.

by keptsissy in Transgender & Crossdressers 01/08/2015
H
4.66
74.4k
43
4
51

Falling Under Mommy's Spell Pt. 03

Matt's life changes under Mommy's control.

by LittlestSissy in Transgender & Crossdressers 02/28/2023
H
4.55
36.9k
42
17
60

Life with My Step-Daughter Ch. 03

Horny step-dad caught by daughter's friend.

by herdad in Incest/Taboo 11/20/2008
4
188.7k
37
0
45

What's Your Price?

Young man gets introduced to a new life.

by Checkmate215 in Transgender & Crossdressers 06/05/2013
H
4.5
146.1k
35
17
48
0

Consent Ch. 03-04

Jack struggles in vain to resist the pull of fantasy.

by sublocked in Transgender & Crossdressers 01/10/2016
H
4.63
42.2k
35
8
47

Tom Boy Tom Girl

Sissy takes anal cum first time.

by Alluring_Crimson_Shifter in Gay Male 05/14/2016
4.24
49.4k
35
3
44
0

Reunion Nightmare

Crossdressing past exposed to new wife at family reunion.

by CindyTV in Transgender & Crossdressers 03/17/2022
4.31
21.3k
33
32
57
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

Vicky Ch. 01

Victor gets a letter that changes his life.

by WritingMyOwnReality in Transgender & Crossdressers 08/27/2007
H
4.69
82.3k
32
7
37

Uncle Jacks Off

A young man finds out he likes to be used.

by SpoonThief in Transgender & Crossdressers 10/27/2011
4.42
61.1k
32
7
39
0

Crossdressing and the Delivery man

Chris takes a delivery of a different sort.

by whields in Transgender & Crossdressers 01/09/2022
H
4.56
18.6k
31
6
37
0

I Love My Breasts!

And how things developed.

by grgy56 in Transgender & Crossdressers 12/13/2018
4.4
39.5k
31
5
41

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
18.6k
31
7
44
0

The Sophomore Ch. 01

Adam has an unexpected Halloween.

by femenistika in Transgender & Crossdressers 07/14/2022
4.47
16.7k
29
8
45
0

Falling Under Mommy's Spell Pt. 05

It's mommy's world and Maddy is living in it.

by LittlestSissy in Transgender & Crossdressers 10/26/2023
H
4.63
18.6k
29
4
54

The Client

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

by Arrowknee in Transgender & Crossdressers 12/05/2021
H
4.58
18.8k
28
4
52

My New Pet

F/m- a recently switched sub gets what he really wanted

by whisperingsubmission in BDSM 06/17/2010
4.48
74.5k
28
2
39

The Princess Frog Ch. 01

It wasn't just a kiss that changed me.

by grgy56 in Transgender & Crossdressers 10/20/2021
H
4.6
14.7k
28
0
48

Love, Sex, Revenge Pt. 02

Kim explores Johnny's love of Pantyhose and CD.

by CindyTV in Transgender & Crossdressers 03/09/2022
4.08
22.5k
27
15
54

Learning to Crossdress Pt. 04

Seduced by a Beautiful Older Lady.

by crossdressme70 in Mature 11/05/2016
H
4.67
34.8k
27
7
29

Accommodating the Rugby Men Ch. 04

Dozens of Rugby hulks do a pansy boy in a mini.

by Cumfusion in Gay Male 12/30/2010
H
4.63
49.9k
26
5
32

Stuck at Home Ch. 01

Getting (p)antsy under quarantine.

by grgy56 in Transgender & Crossdressers 04/19/2020
H
4.52
26.2k
26
4
45

My Summer as a Girl Pt. 02

Meet my aunt's new producer for her internet shows.

by RightButSexy in Transgender & Crossdressers 06/12/2018
H
4.5
33.6k
25
4
29

Satin Blowjob

Caught in her satin lingerie, her hot cock gets pleasured.

by SilkySatinSex in Transgender & Crossdressers 12/21/2011
4.22
91.3k
25
3
28
0

Growing Up Male & Becoming a Girl

Dressing as a girl.

by TammyPanty in Transgender & Crossdressers 03/15/2019
4.4
40.3k
24
2
40
0

Too Late

When your Crossdressing leads to becoming her Cuckold.

by CindyTV in Transgender & Crossdressers 01/21/2022
3.78
21.3k
24
22
41
0

Dear Diary

A Hypnotist helps Joe with his work problems and more.

by MissYellowPanties in Transgender & Crossdressers 03/25/2019
H
4.69
22.5k
23
6
31
0

The Thorns Upon the Roses Ch. 04

Abby takes Jess down for a trip to the lake house...

by SarahSal in Transgender & Crossdressers 09/05/2022
H
4.78
10.3k
22
5
24

The Transition Ch. 02: Jamie

Jamie has to decide if he will crossdress for sex.

by Quantarx in Transgender & Crossdressers 06/08/2020
H
4.69
20.5k
21
2
30

One Sissy's Night

Cross dressing sissy gets the night of his/her life.

by Devient_Mind in Transgender & Crossdressers 10/10/2014
4.19
84.8k
20
10
27

The Beauty Therapists and the CD Ch. 01

Cross-dressing with my wife and her two friends.

by satinpaul in Transgender & Crossdressers 08/20/2010
4.19
63.6k
20
5
24

My Summer as a Girl Pt. 03

Aunt Janey and I star in our first big online show.

by RightButSexy in Transgender & Crossdressers 07/10/2018
H
4.56
27.5k
20
3
25

One Sissy's Night Ch. 02

Continuation of a sissy boy's night out.

by Devient_Mind in Transgender & Crossdressers 10/11/2014
4.36
48.3k
19
10
24

You Got the Part! Ch. 02

Riley takes over.

by Checkmate215 in Transgender & Crossdressers 06/17/2013
H
4.56
45.7k
19
1
20

Match of the Day

Dressed in nylons to be fucked by wife.

by trueorfalse in Transgender & Crossdressers 05/11/2010
4.37
116.6k
19
11
26
0

Away from Home Fun

A crossdresser gets more than they bargain for in a hotel.

by paige_silk in Transgender & Crossdressers 01/28/2023
4.49
17.9k
18
3
33

The Lady Share Cropper Ch. 02

Breaking in her new ponyboy our Lady makes new friends.

by gmikeisbad in NonConsent/Reluctance 10/06/2013
4.13
35.3k
18
1
22

Girly 'Boy' Loves His Man

Feminine guy sets the stage for a lover's romp.

by Clintdear in Transgender & Crossdressers 01/14/2007
4.28
121.2k
17
0
23
0

The Thorns Upon the Roses Ch. 02

Joshua's first day of classes is also his last...

by SarahSal in Transgender & Crossdressers 09/03/2022
H
4.6
12k
17
3
22

How I Became a Transvestite

A man's journey into crossdressing.

by RomeoDelta in Transgender & Crossdressers 06/15/2018
4.48
29.9k
17
2
21
0

Laundry Fun

Cross-dressing, strap-on fun with Maria.

by Rexman9 in Transgender & Crossdressers 11/14/2007
4.01
97.3k
17
2
18
0

My Summer as a Girl Pt. 04

Cross dresser has trouble back at school.

by RightButSexy in Transgender & Crossdressers 08/14/2018
H
4.61
20.9k
16
0
18

Becoming Mindy Ch. 06

The next morning helps Mindy make a decision.

by mindyrose in Transgender & Crossdressers 04/14/2015
H
4.68
27.9k
15
3
16

Little Black Dress

He finally got him to wear his little black dress.

by tommy22co1978 in Gay Male 12/02/2007
4.45
87.7k
15
4
21
0

My Summer as a Girl Pt. 06

Time for the big reveal.

by RightButSexy in Transgender & Crossdressers 11/13/2018
H
4.65
19.8k
14
1
18

The New Job

The new job has consequences.

by bobberjob in Transgender & Crossdressers 12/20/2023
4.44
13.5k
14
7
33

The Thorns Upon the Roses Ch. 03

Jess meets some new faces around campus...

by SarahSal in Transgender & Crossdressers 09/04/2022
H
4.63
10.2k
14
1
15

Conversation with Gabriella Ch. 01

Gabriella explores her sub while all share her wife.

by stacey_lynne in Transgender & Crossdressers 06/22/2006
H
4.51
63.5k
14
0
22

I'm Now Called Dee Ch. 03

First time going out presenting as my new persona.

by RomeoDelta in Transgender & Crossdressers 02/11/2018
H
4.51
23.2k
13
1
16

Doll Parts

Girl meets a boy in skirt.

by dekucat in Transgender & Crossdressers 04/12/2004
3.88
112.1k
13
2
13
0

Her Journey

She discovers the exciting world of men in sexy lingerie.

by noisymother in Transgender & Crossdressers 06/27/2008
4.36
69.9k
12
11
12
0

Freshman Year Ch. 02 - The First Assignment

A freshman boy continues his journey into submission.

by GoHot45 in Gay Male 02/18/2021
4.49
10.3k
12
2
15

Big Day for Sissy Pt. 01

Master introduces sissy to new adventures.

by KurtWaldman in Transgender & Crossdressers 09/03/2016
3.98
16.8k
11
3
11
0

First Contact

First time experiencing going female.

by bobberjob in Transgender & Crossdressers 06/08/2023
4.46
11.7k
11
8
14
0

Weekend Games Ch. 02

Andie & Tammy continue their fun.

by SissyAndi in Transgender & Crossdressers 02/15/2015
4.49
28k
11
3
13

Beau Peep

Both sheep and virtue are lost.

by grgy56 in Transgender & Crossdressers 10/06/2021
H
4.6
8.5k
10
1
17
0

The Perfect Sex Robot Ch. 03

Remote controlled for a public dress up session.

by gmikeisbad in Fetish 05/25/2011
3.63
61.7k
10
2
19

My Summer as a Girl Pt. 07

He comes home drunk and she wants to punish him.

by RightButSexy in BDSM 02/12/2019
H
4.64
13.2k
10
4
14

My Wife Is The Boss

Wife brings out the woman in her man!

by Laurasbitch in Loving Wives 09/13/2009
3.67
50.8k
10
18
15
0

A Charity Case

Can a Guy Dress for Success in an All Girls Hotel?

by pocketrocket in Novels and Novellas 12/03/2014
4.41
16.1k
10
2
16
0

The Princess Frog Ch. 03

The water gets hotter.

by grgy56 in Transgender & Crossdressers 03/25/2022
H
4.81
6.5k
10
1
12

My Ring Pt. 07

Denis and Laraine explore their bodies.

by LittlestSissy in Transgender & Crossdressers 06/12/2023
H
4.73
8.9k
8
5
15

My Ring Pt. 06

Laraine and Denis spend the evening together.

by LittlestSissy in Transgender & Crossdressers 05/25/2023
H
4.72
8.8k
8
1
13

The Best Double Dare

My first night as a sissy boy.

by JD8hrs in BDSM 08/27/2023
4.45
12k
8
2
23

A Game within a Game Ch. 03B

A kidnap - a healing

by doberinca in Transgender & Crossdressers 03/06/2012
H
4.67
19.7k
8
5
11
12
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