‘transvestite’ stories

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Active tags
transvestite 

Category

Wilma Ann & Friends - The Audition

A shy CD comes out of the closet with an experienced tranny.

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Emma's Stiletto Seduction Pt. 06

Emma finally gets her just desserts from David.

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Lady's Bottom – 01: An introduction

Life in an English village where women are in charge.

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Sissy Maid to Mom and Sister Pt. 03

Liz bonds with her mom before her sissy maid brother returns.

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Sissy Maid to Mom and Sister Pt. 01

Andy gets caught by his sister in her panties and it's fine.

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Rick Mallet Ch. 05-06

He "interrogates" a transvestite.

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Camming Down the Rabbit Hole Ch. 08

Going deeper into the warren has never been so much fun.

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Brian or Brianna? Pt. 01

Crossdresser gets caught and has to make a .

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A Day Out Goes Wrong

A day where things go wrong.

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Camming Down the Rabbit Hole Ch. 07

Technical trouble causes outage, but the show must go on.

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The Law Rises to the Occasion Pt. 02

Franko follows the dictates of duty (kind of).

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Sweet Pauly Purebred

Drag helps a tiny Asian teen find his (or her) true self.

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My New Lifestyle Pt. 02

Tom 'opens his eyes' by opening his mouth for black cock!

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All The Pretty Girls Ch. 02

Another girl is taken and Penelope works to solve the case.

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Emma's Stiletto Seduction Pt. 04

Trans Emma's coworker finds a new hole.

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Old and Gr(a)y

Old dog, new tricks.

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Emma's Stiletto Seduction Pt. 03

Sex outside leads to a sticky situation with voyeur…

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The Humiliation of Emma

Tranny drinks cum and piss.

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Crystal Becomes a Tranny Slut

My story of how I started crossdressing as Crystal.

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The Making of an Angel Pt. 08

Further adventures of a cock addicted slut.

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Almost Damsel Almost in Distress Ch. 04

Tgirl continues her adventures and slips into some latex.

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Plumbered

A guy renovating his house finds just the right plumber.

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What If - Scotty the Hottie Ch. 01

Phoenix stays late with a hook-up & ends up abusing her host.

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It’s Only Dinner - A TRANSformation Pt. 01

How far will Nick go to help his childhood friend?

4.49
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What If - Montreal Trip Ch. 02

Phoenix blows a man in the steam room at the airport hotel.

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Ginger and Jules Sissy Story Ch. 04

Couples have dinner, cock sucking ensues.

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The Blond Foreigner

Stranger mixes up male love relationships at Spanish café.

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The Island Ch. 02

Bobbie reveals his secret to the crew of the PT 991.

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Pizza Delivery with a Twist Ch. 06

My working solo weekend proposal requires approval.

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The Island Ch. 01

Four marooned sailors are joined by a stranger with a secret.

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Loss of Control Pt. 09

Diana and Tanya begin new lives separated from each other.

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Ginger and Jules Sissy Story

Two couples with cross dressing husbands start a friendship.

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The Lad in the Lingerie Shop Ch. 13

Last Chapter: How to have a sissy honeymoon and beyond.

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The Prince and the Fairy Pt. 07

A Transvestite, foils a terrorist plot, but at what cost?

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The Lad in the Lingerie Shop Ch. 12

Penultimate Chapter: Robert - the fiance in frillies.

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Of Course The Offer Still Stands

A sissy meets a special couple and gets her cherry popped.

4.39
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28
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Sissy Loni on the Big Island Ch. 05

Steve shares special intimacy with Loni as his secret spot.

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3.4k
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Jack's Offshore

New Orleans crossdresser/transvestite meets offshore worker.

4.15
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Sissy Loni on the Big Island Ch. 03

Loni makes it to Hawaii, meeting Steve at his place.

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The Sissy Department Store Ch. 05

The young lovers story comes to conclusion in full make-up.

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The Prince and the Fairy Pt. 03

A Transvestite, foils a terrorist plot, but at what cost?

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The Prince and the Fairy Pt. 02

A Transvestite, foils a terrorist plot, but at what cost?

4.46
3.3k
2
1
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The Prince and the Fairy Pt. 01

A Transvestite, foils a terrorist plot, but at what cost?

4.3
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7
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The Sissy Department Store Ch. 04

Some dressing and make-up and a three-way.

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The Sissy Department Store Ch. 03

Sissy gets some appropriate clothing and some pussy finally.

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The Sissy Department Store Ch. 02

The Women bond deeply, sissification begins.

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The Lad in the Lingerie Shop Ch. 08

Robert gets to wear his boss's panties.

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The Sissy Department Store Ch. 01

A young sissy is caught and turned out.

4.44
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CD Stacy's Birthday Surprise

Stacy's girlfriend takes her out for a birthday surprise.

4.46
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Outed as a Crossdresser

Another story of my life with Mistress Sharon.

4.24
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An Evening of Crossdressing

My Mistress and her girlfriend dress me as a girl.

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Jennifer's Big Night Out Ch. 04

Jenn's big night out with the girls continues.

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The Eromenos Pt. 02

Rahi finds herself in an unusual situation.

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Promise

Paths that cross will cross again.

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Failed Connections

Pro soccer player goes for fetish play in Denver and Chicago.

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Neville

Crossdresser gets corporal punishment.

4.24
9.1k
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A Holiday Worse Than Hell

You go on holiday to relax. This was anything but relaxing!

3.23
22.8k
2
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Gay Love in Bozeman

An older man finds romance with a young gay lover.

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One for the Team Ch. 08

Archie and Sandra piece together what happened to Charlotte.

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One for the Team Ch. 06

Charlotte & Wendy have grand designs to run a tranny brothel.

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How had I been volunteered?

Be careful when raising funds for a charity!

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22

One for the Team Ch. 01

Closet TV is sent to boarding school where she is found out.

4.49
26.3k
29
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Groomed to Depravity Ch. 03

The journey of feminization begins in earnest.

4.49
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47
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Amelia Jones Ch. 01

Wife is brought into husband's transsexual fantasy

4.47
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38
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Groomed to Depravity Ch. 01

A college boy's life goes awry on Halloween.

4.42
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295
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The Tree Man saw me!

Wife planned a visitor who caught me out as a sissy cuckold.

4.47
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27
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39
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The Women's Spa - Almost

I visit an all female spa with a little difference.

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33
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The Flaming Girls Ch. 05

Can Charlie and Robin have a meaningful relationship?

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The Flaming Girls Ch. 03

Charlie goes back to working the streets despite the Slasher.

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The Flaming Girls Ch. 02

Essex Slasher's backstory and Charlie's torment continues.

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The Flaming Girls Ch. 01

Charlie is a special girl & she's about to be a Flaming Girl.

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16.3k
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Jennifer's Big Night Out Ch. 02

Jennifer's night out with the girls continues.

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4.55
13.1k
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3
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Lumberyard Miracle

A tale of improbable love.

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4.83
32.5k
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Truth and Beauty in Buttermilk Falls

Sammy's new neighbor had his damn key!

3.91
9.2k
2
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Jerry becomes Jill Pt. 03: It Gets Serious

Female lead relationship and shopping for clothes...

4.48
25.4k
23
4
26

A Latex Crossdresser's Dream Pt. 06

A Latex Crossdressers Dream. Part 6. "The Dream continues."

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4.79
8k
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The Surrogate Ch. 04

Trans surrogate wife decides to become permanent TS.

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4.77
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21
13
30

The Surrogate Ch. 03

Mila is curious about her sexuality and seeks to remedy it.

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4.62
22.6k
17
5
24

The Surrogate Ch. 02

Man becomes his sister and marries brother-in-law for money.

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4.69
32.7k
24
6
37

The Surrogate Ch. 01

Twin brother stands in for sister for wifely duties.

H
4.59
56.9k
68
7
133
Active tags
Active tags
transvestite
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