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‘cross dressing’ stories

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Comforting Pete meets Trophy Wife

Characters from 2 stories meet in Vegas- Picks up from CP 4.

by WhyNotUs in Transgender & Crossdressers 07/23/2023
H
4.82
8.5k
18
2
31

Becoming My Sister Pt. 08

Aimee’s first public appearance.

by fantasy_writer_2023 in Transgender & Crossdressers 01/09/2024
H
4.8
9.2k
18
4
24

Little Sister Ch. 05

At a party, Jean goes down on Ralph.

by Da_Vida in Transgender & Crossdressers 03/14/2009
4.48
59.1k
18
3
19

Black Mistress-White Bitch Ch. 08

The white bitch becomes a white ho.

by lusty Vamp in BDSM 03/31/2008
H
4.63
97.8k
18
6
22

The Slave Traders Pt. 03

Humiliation and loss of Control to Freedom.

by jamtby in Transgender & Crossdressers 01/16/2019
4.1
37k
18
5
22

A New Perspective Ch. 01

A Halloween party provides new opportunities.

by mgrif024 in First Time 11/25/2022
H
4.5
15.6k
18
3
30

Becoming a Gal Friday Pt. 11

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

by Showoff888 in Gay Male 12/28/2014
H
4.57
28.9k
18
5
20

Wererock

A man finds a rock with the power to change everything.

by Tester86 in Fetish 06/10/2021
4.12
13.7k
18
11
44
0

Enticed and Humiliated Ch. 05

College boy explores cross dressing and maid service.

by FantasizeAndRealize in Transgender & Crossdressers 08/17/2015
4.25
54.6k
17
4
19

Jewel

An older woman.

by JhMcKn in Fetish 07/19/2015
4.39
33.2k
17
1
21

A Freshman's Summer Class Ch. 09

As summer ends, new opportunities open.

by CapnSteelBoy in Transgender & Crossdressers 06/13/2020
H
4.61
15k
17
6
24

The Weekend Ch. 01

A submissive works in a gloryhole.

by SubmittingSubmissive in BDSM 07/09/2016
4.24
36.2k
17
9
29

The Best Day of My Life Ch. 02

Harley's date isn't over, and he has another surprise.

by HarleyLongshanks in Transgender & Crossdressers 08/10/2020
H
4.57
13.2k
17
5
22

Call Me Teddy

Sexy lingerie with a twist.

by smithjon1919 in Anal 04/09/2009
4.39
56.5k
17
1
22
0

Tits Have Benefits Ch. 09

Is this the end for Andrea?

by hottchic in Transgender & Crossdressers 07/27/2011
H
4.61
28.8k
17
11
19

Chris' Adventures Ch. 02

Chris is caught in his wife's lingerie by the neighbor.

by curiousone43 in Fetish 02/22/2018
H
4.79
23.7k
17
1
24

The Bully Pt. 04

Lela forces me to accommodate John’s every need.

by RegularGuy2020 in NonConsent/Reluctance 11/24/2022
4.17
21.9k
17
0
31

Finding Fulfillment At Home Pt. 03

Tranny son and Bi Daddy find true love.

by Showoff888 in Incest/Taboo 08/24/2014
H
4.52
22.8k
17
0
20

Skipper and the Cabin Gurl

Lanna really rocks the Skipper's boat!

by LannaLace in Transgender & Crossdressers 02/05/2023
H
4.69
13.9k
17
5
34

A Bear Seduction, the Outfit

Kevin introduces me to cross dressing.

by wildrideagain in Gay Male 02/14/2015
H
4.51
35.3k
17
6
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
42.7k
17
4
21

Becoming My Sister Pt. 09

Aimee’s first public appearance continues…

by fantasy_writer_2023 in Transgender & Crossdressers 01/19/2024
H
4.83
5.5k
17
2
23

Jaimie's Birthday Party

James / Jaimie celebrates coming out with an orgy.

by jon.hayworth in Transgender & Crossdressers 06/14/2020
4.45
13k
17
1
22
0

Sissy Comes Clean

A loving wife helps husband accept his sissy tendencies.

by Cuckyboy3 in Fetish 10/02/2020
3.9
45.2k
17
9
40
0

Another Thing Cumming

He's got another thing cumming on a Hot Summer Night.

by theravenfox in Audio 09/01/2010
3.97
178.4k
17
10
24
0

Which Would You Like to Try?

Wife asks husband to tell her his five favourite fantasies.

by Nifrag in Fetish 04/26/2023
4.3
19.3k
17
3
46
0

Weekend Games Ch. 03

Andie and Tammy have a lesbian 3sum.

by SissyAndi in Transgender & Crossdressers 03/04/2015
4.49
22.8k
17
4
18

Finding the Perfect Fit Pt. 16

Jamie spreads his legs for Gen and she performs.

by Joshana in Transgender & Crossdressers 02/26/2020
H
4.82
10k
17
5
23

Matt's Change

Matt learns something when his sister moves in.

by Dark Scribe in Transgender & Crossdressers 04/05/2005
4.22
120.5k
17
5
24
0

House Mother's Toy

A young man becomes an older woman's toy.

by 0ra11yfix8ed in First Time 08/01/2015
3.96
60k
17
2
21
0

Lost Suitcase Adventure Pt. 03

Jessica's Plan - Jesse moves in - Worlds collide.

by WhyNotUs in Transgender & Crossdressers 01/30/2024
H
4.68
7.1k
17
2
23

My VideoChat Error Ch 28

Shaun(a) dances with and submits to forced BBC BF.

by NaughtyOne88 in NonConsent/Reluctance 07/12/2020
H
4.63
28k
17
30
35

For Her Pleasure

Two pantyboys put on a show.

by HConway in Transgender & Crossdressers 04/12/2017
H
4.57
36.5k
17
6
28
0

Caught by the Lodger Ch. 02

Rachel continues training Suzie with the help of a friend.

by SuzieR in Transgender & Crossdressers 02/03/2010
H
4.61
54.8k
17
1
21

A Highland Holiday Pt. 02

Fiona and Josie discover more of the highlands & themselves.

by MissYellowPanties in Transgender & Crossdressers 07/29/2017
H
4.61
13.2k
17
2
18

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

Public Cross Dressing Experience Ch. 02

Public cross dressing experience evolves to permanence.

by sublocked in Transgender & Crossdressers 05/29/2012
4.21
60k
17
9
20

Meg Saunders

A late 30s woman meets and seduces a transgirl.

by JohnMurray4173 in Transgender & Crossdressers 01/30/2023
4.46
12.1k
16
2
31
0

My Friend Becky

Giving her some peter and her loving it.

by JhMcKn in Erotic Couplings 12/27/2015
3.84
34.8k
16
6
19

Suzy and 'Mistress' Danielle

Suzy is spanked and filled by a cross dressing mistress.

by LucyCanyon in Transgender & Crossdressers 05/11/2017
4.47
11.3k
16
0
21
0

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

Fender Bender Ch. 05

Vicki rewards the Mechanics.

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

Trophy - The Preys Story

There are two sides to every story.

by MissYellowPanties in Transgender & Crossdressers 11/13/2017
4.44
15.8k
16
0
19
0

Something in the Water Ch. 02

Wife coaxes her bashful husband to be feminized.

by sublocked in Transgender & Crossdressers 03/22/2012
4.45
97.4k
16
5
18

The Rise of Rachel Price T-Girl Pt. 02

Charlie experiments and transforms Denver into new Rachel.

by racheprice in Transgender & Crossdressers 01/02/2023
H
4.61
11.1k
16
7
20

A Time for Giving and Discovering

Staying at a Spa for Christmas reignites a couples sex-life.

by Cristal_di_Canta in Transgender & Crossdressers 12/01/2023
H
4.86
14.2k
16
6
43
0

Trapped Teacher

This teacher ends up blackmailed.

by L R in Fetish 12/15/2001
4.12
133.1k
16
0
22
0

Joanna Goes For Training Ch. 02

Mike visits the house. Colleen attends a cuckold's group.

by Quietoldie in Fetish 05/19/2020
H
4.72
22k
16
11
29

Strange Feelings

Recent sissy discovers new cravings she can't ignore...

by ChrisLePaige in Transgender & Crossdressers 07/15/2017
4.35
27.9k
16
1
19
0

Bambi or Bust Pt. 02

I found out what Bambi's done to me in the last 2 days...

by SissyGeorgina in Transgender & Crossdressers 02/19/2024
H
4.62
10.9k
16
2
26

Aunt Judith Ch. 04

Aunt has a party.

by maudecardy in Incest/Taboo 06/26/2009
4.33
77k
16
7
19

Monsignor & Mommy Pt. 02

Partying, fucking, incest, oral sex, and alcohol, lingerie.

by JhMcKn in Incest/Taboo 02/18/2022
4.19
12.5k
16
1
23

A Day in the Life...

...of a Cuck Queen & her Mother.

by HottieOlwen in Fetish 08/06/2021
3.98
17k
16
3
37
0

Mistress Nurse Ch. 01: Golden Beginnings

Exotic Nurse and I begin our kinky medical fetish adventures.

by Fantasy_Doctor in Fetish 10/17/2021
4.42
23.8k
16
6
34

Joey Finds a New App Ch. 38

Joey has a wild inservice day at school.

by Daddy_0H in Interracial Love 01/30/2022
H
4.7
12.1k
16
3
29

The Agency Ch. 18

Custom clothes shopping for Michelle is an adventure.

by Ms_Allison in Transgender & Crossdressers 04/05/2022
H
4.78
9.1k
16
6
23

First Time Cuckold Ch. 04

Conclusion.

by Angelscuck in BDSM 09/29/2013
4.37
39.1k
16
1
18

A Hand in My Panties

A crossdressing bi virgin's 1st time.

by Ballen1111 in Transgender & Crossdressers 06/23/2019
4.4
35.5k
16
14
20

The Pelvic Exam Pt. 02

Allan is fucked literally and figuratively by Marika.

by Wonderer67 in NonConsent/Reluctance 01/29/2023
H
4.6
25.3k
16
8
39

Stuck at Home Ch. 02

Caught! Now what?

by grgy56 in Transgender & Crossdressers 05/24/2020
H
4.57
17.9k
16
3
23

Life on the Farm

Sexual transformation in a country bordello.

by Da_Vida in Transgender & Crossdressers 02/13/2009
4.32
74.6k
16
7
21
0

Forbidden Lovers

Private Taylor "Danish" Barrit loves femboy pilot.

by NotAGreatWriter in Transgender & Crossdressers 06/02/2016
4.26
20k
16
1
24
0

Inheritance (One Week Chronicles)

Gary is forever changed as Louise and Jade enter his life.

by Louise69 in Transgender & Crossdressers 06/23/2017
H
4.72
55.4k
16
5
24
0

Long Night Ch. 01

Wife shows husband what a real man can do.

by tieddown in Fetish 05/16/2010
3.86
130.8k
16
9
26

The Pool Pt. 04 - The Gathering

One slut, four cocks. that was the invitation...

by ChasBozwell30 in Gay Male 10/12/2021
H
4.68
12k
16
3
28

Pussy Slave: A Fantasy

A man becomes a Pussy Slave.

by redwolf555 in Fetish 02/08/2019
4.13
38.1k
16
5
29
0

Uncovering the Sissy Beneath Pt. 06

Tricia learns another lesson while in bondage.

by jefferyscott745 in Transgender & Crossdressers 07/30/2019
H
4.68
19.3k
15
1
19

Cody Becomes Chloe Pt. 01

A teen goes on Craigslist and meets Will.

by Southernstud97 in Transgender & Crossdressers 03/19/2015
3.54
41.6k
15
9
20
0

Courting Cheryl

He undergoes feminization to win a girl's affection.

by RonWCB in Humor & Satire 11/06/2006
4.22
51.9k
15
5
20
0

A Gurl in the Making Pt. 01

A young man discovers more than they bargained for.

by pantyboidoe in Transgender & Crossdressers 02/22/2024
H
4.5
14.6k
15
3
45

An Evening of Crossdressing

My Mistress and her girlfriend dress me as a girl.

by cockteezer in Transgender & Crossdressers 09/15/2020
4.44
19.7k
15
3
19
0

Could I Spank Another Guy?

Ad says guy wants a spanking. Was it gay to want do it?

by JRob in Gay Male 07/01/2017
4.43
21.4k
15
12
20
0

Shirley has An Adventure Ch. 02

Hubby dresses up and gives Charles a blow job.

by Quietoldie in Transgender & Crossdressers 06/27/2021
H
4.66
14.3k
15
6
18

Rosie and Julian tell their Story

Wife dominates hubby and fucks her boss reluctantly.

by Quietoldie in Fetish 11/29/2021
4.17
18.3k
15
9
38
0

Panties, Porn and Bi Pleasures Ch. 02

Second part of my Jack and Chris (+) story. ❤️ panties!

by Meo645 in Fetish 04/08/2022
H
4.62
9.5k
15
1
21

I Can See You

A man wears his wife's clothes, but who's watching the CCTV.

by simone77 in Transgender & Crossdressers 12/08/2018
H
4.52
19.9k
15
7
17
0

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
45.5k
15
5
19
0

Blackmailed into Submission

Blackmailed into submission by my neighbor.

by tzleaze123 in Transgender & Crossdressers 02/17/2019
4
49.7k
15
6
27

Little Sister Ch. 07

Denise teaches Jean about butt fucking.

by Da_Vida in Transgender & Crossdressers 03/16/2009
H
4.54
58.4k
15
3
16

The Office Party and a Dare

F/M / Bondage / Forced orgasm / Cross dressing.

by EGuzman in Erotic Couplings 11/23/2016
0
25.2k
15
0
19
0

The Descent Ch. 02 - A Slow Glide

His fall for the Madam accelerates.

by pantywriter in Transgender & Crossdressers 08/29/2020
H
4.79
12k
15
5
22

Lt. Gordon's Transformation Ch. 02

A transporter accident changes the direction of a man's life.

by DMaster_14 in Celebrities & Fan Fiction 02/14/2010
H
4.58
39.4k
15
4
20

Not So - New Experiences

Can't call it a new experience if you do it twice!

by writerfromoz in Gay Male 07/27/2017
H
4.75
20.1k
15
9
17
0

The Law of Attraction Ch. 03

Jamie's Story: Jamie gets fucked.

by hottchic in Transgender & Crossdressers 08/26/2011
H
4.71
41.1k
15
5
16

The Live-in Maid Ch. 03

Mistress farms me out, her mum visits & burglary turns sexy.

by Quietoldie in NonConsent/Reluctance 03/07/2018
4.49
26k
15
4
24

The Helmet Ch. 01

A consensual slave deals with realities of slavery.

by sublocked in NonConsent/Reluctance 04/10/2012
4.13
66.7k
15
6
28
0

Finding the Perfect Fit Pt. 13

A young couple make this night one to remember.

by Joshana in Transgender & Crossdressers 01/28/2020
H
4.79
11k
15
2
20

Joey Finds a New App Ch. 57

Joey starts another school week off with a bang.... or two.

by Daddy_0H in Incest/Taboo 01/06/2024
H
4.6
7.9k
15
0
18

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

Mistress Cruel Love Ch. 02

Darius falls farther down the rabbit hole.

by ChainedToAKeyboard in BDSM 09/12/2020
H
4.66
15.6k
15
0
38

The Agency Ch. 16

It's thenight of Michelle's graduation party.

by Ms_Allison in Transgender & Crossdressers 01/26/2022
H
4.82
10.6k
15
9
24

True Lies Ch. 01

Minds (M-F) Switched. Was it real or was it a dream?

by grgy56 in Loving Wives 03/23/2018
3.32
19.8k
15
9
26
0

Mother's Guest

An FLR Family.

by skinnysailor in Transgender & Crossdressers 04/13/2022
4.11
22.2k
15
0
35

Caught in the Laundry

Sub cross dressing husband caught dressing.

by kinkawon in Transgender & Crossdressers 11/28/2022
H
4.5
18.7k
15
7
31
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