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‘crossdress’ stories

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Awkward Boner Ch. 02

The girls give him a present, and teach him to like anal.

by FemFreak in Transgender & Crossdressers 05/10/2021
H
4.57
34.8k
45
1
69

Adam Loses a Bet Ch. 06

Nothing but an apron🍑

by Amy_wants_more in Transgender & Crossdressers 01/29/2021
H
4.57
38.8k
28
2
45

Jacki's Journey into Sissyhood

A crossdresser's journey into be a full-fledged sissy.

by jacki697 in Transgender & Crossdressers 12/17/2014
H
4.57
115.4k
84
6
124

Tango on the Razor's Edge Ch. 03

A Sissy Cuckold Shopping Spree.

by sinisterout in Transgender & Crossdressers 12/23/2020
H
4.57
19.6k
14
1
20

Trapped! Ch. 04

A convincing young CD prepares herself for Halloween...

by EffieMeow in Transgender & Crossdressers 06/20/2019
H
4.57
13.9k
11
0
14

Sissy/Cock Sucker Dictionary

A list to understand the nature of sissies/cocksuckers.

by silkstockingslover in Reviews & Essays 06/10/2019
H
4.57
71.7k
137
45
188
0

Downsizing Ch. 09

Dani decides on Augmentation.

by My5InchFMHeels in Transgender & Crossdressers 09/27/2016
H
4.57
17k
15
7
16

The Ten Game Pt. 04

Sam and Marina's training comes to a climax.

by THEGREATDANE99 in BDSM 03/27/2018
H
4.57
17.5k
18
6
23

Agnes Dourville Ch. 16

A lark after dark.

by ValoryG in Transgender & Crossdressers 12/13/2017
H
4.57
7.7k
3
0
6

My Twin

Toni replaces his twin sister when she dumps her boyfriend.

by CoenaElixa in Transgender & Crossdressers 07/02/2023
H
4.57
21k
42
6
83
0

Sweet Treat Ch. 02

Some surprises await crossdressing Stefania at the party.

by SaucyMasquerade in Transgender & Crossdressers 03/27/2023
H
4.57
7.6k
4
4
9

I Need to Tell My Story Pt. 03

Jackie nee Froggie tests the waters.

by ValoryG in Transgender & Crossdressers 11/11/2023
H
4.57
1.9k
2
1
3

A College Whore Pt. 03

Sean (Now named Candy) is blackmailed into modeling!

by sophielopes in Transgender & Crossdressers 03/28/2024
H
4.57
10.4k
14
2
24
0

Our Sissy Slave Ch. 02

You adventures at the hands and dildo of your girlfriend.

by purekink in Transgender & Crossdressers 05/27/2009
H
4.57
181.8k
76
20
93

MiRI Ch. 03

Mom helps me with my changes.

by grgy56 in Transgender & Crossdressers 09/07/2022
H
4.57
13.7k
26
1
29

Kinky Boating Fun

Wife dominates her sissy husband when new friends join them.

by Christy76 in Fetish 03/30/2024
H
4.57
13.9k
16
6
45

MiRI

Treatment side effects.

by grgy56 in Transgender & Crossdressers 08/25/2022
H
4.57
23.4k
49
4
90

Torment Ch. 05

Sasha takes Barbara out for her first shopping trip en femme.

by BJGoodhead in Transgender & Crossdressers 02/28/2022
H
4.57
9k
6
4
12

She Dad Ch. 02

Darla entertains the pastor father of his son's girlfriend.

by FirstTimer69 in Transgender & Crossdressers 01/15/2012
H
4.57
65.8k
37
11
44

The Next Day with Dennis

Janice and Dennis try anal sex for the first time.

by CDBec60 in Transgender & Crossdressers 09/22/2023
H
4.57
5.9k
5
5
6
0

A Bend in the Road

A straight man transitions into a gay relationship.

by Writer_FM in Gay Male 08/15/2018
H
4.56
35.1k
45
10
59

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

Trapped! Ch. 02

A convincing, young crossdresser hooks up with her neighbor.

by EffieMeow in Transgender & Crossdressers 06/04/2019
H
4.56
33.2k
22
1
30

Thief's Got a Pleasant Surprise

2 Thief's had some fun with a surprise crossdresser.

by sammysamson4 in Transgender & Crossdressers 11/17/2020
H
4.56
14.9k
19
5
30
0

Deckhand Adventures 02 - Alexa

Our adventurous deckhand has a secret, eventually shared...

by Lingeringinthecorners in Transgender & Crossdressers 08/11/2020
H
4.56
7.4k
4
0
7

Taking the Plunge Bk. 01 Pt. 05

T & D decide to stay the night and see where it takes them.

by trishasissysub in Transgender & Crossdressers 02/10/2021
H
4.56
8k
9
3
13

Abducted and Turned Out Ch. 04

Another chapter in the continuing saga of a t-gurl whore.

by dawnib66 in Transgender & Crossdressers 04/05/2013
H
4.56
43.4k
29
2
33

Caught Cross-Dressed & Dominated

James is caught dressing in bondage by sexy neighbor.

by bondage_philosopher in Fetish 07/24/2002
H
4.56
257.9k
97
0
123
0

Magic Panties Ch. 04

The Metamorphasis completes.

by nolfon1 in Transgender & Crossdressers 01/27/2011
H
4.56
78.6k
17
2
21

Betrayed Ch. 02

Shop 'til you pop; then, dress for dinner.

by AngelCherysse in Transgender & Crossdressers 06/21/2005
H
4.56
111.8k
24
4
32

Taking the Plunge Bk. 01 Pt. 10

T & D shower and get ready for bed, maybe...

by trishasissysub in Transgender & Crossdressers 02/22/2021
H
4.55
6.6k
4
1
4

Lingerie in the Basement 01

A man discovers his desire for lingerie and steals.

by Lingerieexcitement in Transgender & Crossdressers 02/02/2023
H
4.55
12.1k
24
3
38

Trained to Have Transvestic Fetish

Husband trained to have a severe fetish.

by Everyday2 in Fetish 09/14/2012
H
4.55
124.9k
84
20
109
0

My Story of Degradation Ch. 02

I go to Mistress's house for an interview.

by Philippasubmaid in Transgender & Crossdressers 08/29/2018
H
4.55
17.4k
10
2
14

How I was Trained Pt. 03

Miss Baxter took me to a church where I meet Tony.

by LisasStories in Transgender & Crossdressers 05/25/2023
H
4.55
12.1k
22
9
28

Intensity Ch. 03

Preparing my ass for Friday.

by larrkap in Transgender & Crossdressers 03/31/2022
H
4.55
4.4k
2
0
5

A Femboy's '21st Birthday in Vegas Ch. 02

My bf gets me to go wear a bikini in public and rewards me.

by summerlove91 in Gay Male 08/06/2022
H
4.55
12.2k
10
1
18

Feminized by Girlfriend

A curious boyfriend gets feminized by his girlfriend.

by ThisIsTheRealMeBby in Transgender & Crossdressers 06/24/2023
H
4.55
99.4k
125
48
252

What My Wife Doesn't Know

Cheating / wearing lingerie / submission, then dominance.

by married_but_curious in Transgender & Crossdressers 07/22/2022
H
4.55
27.9k
52
5
89

Barbie Jo Adventures Ch. 01

Barbie Jo gets her cherry popped.

by barbie_jo_69 in Transgender & Crossdressers 12/20/2007
H
4.55
112.9k
41
10
51

First Meet with My Master

A crossdresser meets their master for the first time.

by paige_silk in Transgender & Crossdressers 02/09/2023
H
4.55
8.9k
17
1
35

Shiny Pebbles Pt. 02

The perfect life, interrupted.

by ValoryG in Transgender & Crossdressers 05/17/2019
H
4.55
7.4k
4
2
4

Four Play Ch. 03

Things change when hubbie comes back home.

by grgy56 in Transgender & Crossdressers 09/03/2018
H
4.55
15.2k
12
1
18

The Making of Meaghan Ch. 03

Brian takes time away to sort things out.

by ms_599 in Transgender & Crossdressers 04/01/2018
H
4.55
39.7k
32
5
44

The Gift Ch. 01

An intriguing offer leads to new experiences.

by SecretsOfStevie in Transgender & Crossdressers 03/23/2023
H
4.55
10.8k
11
10
22

Sexy Lingerie Leads to DP

Sexy lingerie leads to cocks in each hole.

by Silk_Panties in Gay Male 01/10/2023
H
4.54
16.7k
13
5
23
0

The Devil You Know Ch. 01

Closet crossdresser caught by boss is blackmailed for sex.

by MicheleNylons in Transgender & Crossdressers 07/15/2009
H
4.54
114k
40
4
54

The Punishment

Fantasy football punishment leads to feminization, gangbang.

by nat_rose in Transgender & Crossdressers 09/09/2018
H
4.54
79.9k
90
13
142
0

Lady In The House Ch. 10

The finale, what will happen to our transvestite prostitue?

by MicheleNylons in Transgender & Crossdressers 12/07/2005
H
4.54
56.8k
18
2
18

My Father-In-Law's New Bride Ch. 03

Father-in-Law continues his training.

by regina_allen55 in Transgender & Crossdressers 10/08/2005
H
4.54
187.5k
59
9
66

Alex for Her and Alexa for Him Pt. 03

Alexa is caught and has a new experience with Josh.

by AlexaFawns in Transgender & Crossdressers 11/02/2022
H
4.54
4.4k
4
0
5

Prom? Ch. 05

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

by New_Girl_ in Transgender & Crossdressers 08/05/2017
H
4.54
36.7k
41
21
51

Lady In The House Ch. 14

Transvestite prison prostitute is forced to sell herself.

by MicheleNylons in Transgender & Crossdressers 01/20/2008
H
4.54
43.8k
13
1
13

Willing to do anything

A debt costs a man his dignity.

by LittlestSissy in Transgender & Crossdressers 08/27/2023
H
4.54
56.1k
70
11
130

I Need to Tell My Story Pt. 02

Venturing out, good vibrations, and meeting Carlos.

by ValoryG in Transgender & Crossdressers 10/13/2023
H
4.54
2.9k
2
2
3

Going Home with my Girlfriend

Secrets are revealed while visiting his mom with his gf.

by fantaseeboy in Transgender & Crossdressers 03/15/2020
H
4.54
111.1k
176
23
286
0

Out On the Prowl

Terri gets a date and takes him home.

by BakersfieldCdTerri in Transgender & Crossdressers 01/17/2015
H
4.54
33.2k
9
2
14
0

For The Money Ch. 02

He gets an opportunity in a play.

by SexyPenelope in Transgender & Crossdressers 02/26/2014
H
4.54
58.5k
41
8
42

When Andy became Andi Ch. 02

My time in the sauna was just the beginning.

by Anditv in Transgender & Crossdressers 01/31/2021
H
4.54
13.7k
15
4
19

Friday Night Crossdressing Fun

When you just want to relax but there's fun to be had.

by LisasStories in Transgender & Crossdressers 07/26/2023
H
4.54
10k
13
8
24

Taking a Break

The start of a holiday takes an unexpected turn.

by Claudia_TylerMae in Transgender & Crossdressers 09/29/2023
H
4.54
13k
20
5
36
0

Made Up

A budding crossdresser meets with an experienced trans woman.

by ChewToySub in Transgender & Crossdressers 08/08/2015
H
4.54
38.4k
28
8
35
0

Embracing the Unfamiliar

Aaron's surprise discovery in girl's clothes.

by AdorablyAmy in Transgender & Crossdressers 05/30/2023
H
4.53
13.5k
24
5
35
0

My Day

CD Jessica has an afternoon with her lover.

by sexyctcd in Transgender & Crossdressers 10/08/2017
H
4.53
25.6k
30
4
39
0

Telling Her

When a guy tells his girlfriend he likes to crossdress.

by lacychristine in Transgender & Crossdressers 10/03/2023
0
7.8k
15
7
32

Ilka's Place Pt. 04

Even better vibrations.

by ValoryG in Transgender & Crossdressers 04/18/2023
H
4.53
2.6k
1
1
2

Caught Messaging Master Pt. 13

Lucy gets her ultimate revenge on Katie.

by Sissykatie93 in Transgender & Crossdressers 09/23/2022
H
4.53
5.3k
6
3
7

My Ruined Alone Time

Female classmate discovers my fetish. And hers...

by LizardGummy in Transgender & Crossdressers 07/02/2023
H
4.53
28.4k
49
18
106
0

The Making of SweaterTV Ch. 02

The story continues...

by sweatertv in Transgender & Crossdressers 02/03/2016
H
4.53
8.8k
5
1
5

Walk of Shame

He's made to dress as a slut and walk through the ghetto.

by lululuvsblack in Transgender & Crossdressers 07/18/2015
H
4.53
63k
97
21
122
0

Outing Ch. 02

Sweetie's CD outing adventures continue.

by grgy56 in Transgender & Crossdressers 04/30/2015
H
4.53
21.3k
20
5
23

A Routine Traffic Stop

You know, sexy cop fantasies.

by Angelpenpal in Transgender & Crossdressers 02/23/2021
H
4.53
28.6k
50
2
88
0

The 5-Day Plan

A naughty headmaster ensnares a delicate pupil.

by sissy11 in Gay Male 03/04/2021
H
4.53
51.2k
111
7
201
0

Vickie's New Girl Jennifer

Caught by wife & accepted. Anger to Love.

by CindyTV in Transgender & Crossdressers 01/24/2022
H
4.53
31.5k
42
46
67
0

Jennifer and Patrice Pt. 02

Jen and Patty attend a fancy bondage party.

by BrendaD in Transgender & Crossdressers 07/31/2022
H
4.53
6.7k
12
5
16

Sissy Downfall

My journey from sissy to transformed slut slave.

by davine in Transgender & Crossdressers 07/04/2013
H
4.52
189.1k
102
7
158

Kyle - My First Public Date

Leigh’s first public date.

by Leigh_216 in Transgender & Crossdressers 04/05/2018
H
4.52
17.3k
13
5
18
0

Forced Entry

Transvestite caught in her hotel room is forced into sex.

by MicheleNylons in Transgender & Crossdressers 02/13/2009
H
4.52
255.9k
103
14
137
0

A Night to Remember

My first cock while dressed as a woman.

by VickieTGirl in Transgender & Crossdressers 08/15/2010
H
4.52
128.4k
43
18
52
0

Evening Out with My Master

A crossdresser enjoys a night out with their master.

by paige_silk in Transgender & Crossdressers 10/11/2023
H
4.52
7.3k
8
1
15

It's Only Temporary Pt. 01

Susan helps John become the women he's always dreamed of.

by ChangeYourPassword in Transgender & Crossdressers 12/14/2019
H
4.52
87.7k
75
18
134

Agnes Dourville Ch. 18

From RN to MS.

by ValoryG in Transgender & Crossdressers 12/15/2017
H
4.52
9.9k
4
6
6
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