‘crossdressing’ stories

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Active tags
crossdressing 

Category

Bradi 01

Bradi usually maxes out until.

2.33
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Sissy for Sister Ch. 06

Things move fast when James comes to stay.

4.37
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Becoming My Sister Pt. 04

A boy’s obsession with his sister changes his life forever.

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4.64
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Ffion the Christmas Elf Pt. 04

Ffion is taken by a witch with murderous lusts.

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Sissy for Sister Ch. 04

Sienna takes 'Rose' shopping.

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4.51
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Sissy for Sister Ch. 03

Myles and Sienna's relationship changes forever.

4.29
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The Devil is in the Details Ch. 01

A mature woman makes a demonic deal to live her fantasy.

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4.63
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If Ivy Could Untangle Ch. 02

Avery and Jessica make the next move away from the Doc.

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Sissy for Sister Ch. 02

'Rose Gold' arranges a date.

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Howard is Ours Ch. 02

Howard reflects on how it all began, and joins the party.

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The Family

Family tale of incest, crossdressing and FLR.

3.96
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Lynx Ch. 01

Lynx works the food angle on game day.

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The Sissy

An unexpected orgy with odd changes.

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Becoming My Sister Pt. 03

A boy's obsession with his sister changes his life forever.

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Kinky Day with Stephanie

Nikki and Stephanie Venture out to lunch with Grace.

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Becoming My Sister Pt. 02

A boy’s obsession with his sister changes his life forever.

H
4.6
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Wearing a Skirt and Jerking Off

After a rough day at work I need some stress relief.

4.44
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The Warehouse

A warehouse filled with abandoned belongings.

3.97
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Tobi 01

Tobi works backstage at a traveling TV event.

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Becoming My Sister Pt. 01

A boy's obsession with his sister changes his life forever.

H
4.62
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Well, She Finally Asked Me... Ch. 02

..I told her I had sucked cock. now what?

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Feathering The Nest

John's shooting blanks so Francesca turns to her brother.

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In Over My Head - Supplement

Supplement to the Over My Head series - an aside really.

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The Weekend Sissy

A weekend of free-use, with an alluring demand...

H
4.78
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Caught on Nanny Cam Pt. 02

Johnny gets caught on nanny cam in a french maid dress again.

H
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Stiff Dicks Hiding in Panties Pt. 04

Jennifer becomes my Mistress and pushes me to come out to my.

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At the Mercy of Mrs. Letchworth Ch. 01

I am introduced to Auntie's warped household.

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Caught on Nanny Cam

Johnny caught on nanny cam dressed in French maid costume.

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The Making of a Sissy Pt. 07

Charlene and John set sail for the weekend.

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Remembering Mom

A Yearly Arrangement Between Father and Son.

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Girlfriends Ch. 02

Cheri visits Hunter's house - kinkiness ensues.

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Little Bo Peep - The Eight Outing

Jan and Tiger spend their last day in Japan doing what they.

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Nikki Madison Meets Her Future Wife

Nikki Moves Back East. She meets Ashley a dinner party.

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Teeny Jaye 01

Teeny Jaye works the wood pile at the bonfire.

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Howard is Ours Ch. 01

Howard's bi/crossdressing relationship with John is exposed.

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How I Became Gay

The story of how my girlfriend turned me gay.

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A Developing Fetish Ch. 05

Jaclyn goes out on her own while Melanie enjoys Jesse.

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The Next Doll Pt. 02

Meaghan takes David for her first test drive.

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4.78
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A Night Out

A new dress, a strong Mistress, and a night out on the town!

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4.66
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Stiff Dicks Hiding in Panties Pt. 03

Things at home change as Belle and I have alone time.

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4.78
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Dewy 01

Dewy went all porcelain doll one evening.

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A Night at Trained Strangers Ch. 02

Micah gets the gangbang he's so anxiously been awaiting.

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A Night at Trained Strangers Ch. 01

Micah goes through the interview process.

H
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The Making of a Sissy Pt. 06

Opa got Charlene ready for the yacht cruise ahead.

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Nyx 01

Nyx worms his way into everything.

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My Cross-Dressing Secretary

What happens in the pool stays in the pool.

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Alex 01

Alex didn't plan to have a party, but that's the way it went.

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Bigger Ch. 01

I go in for a procedure to make me bigger.

4.46
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Dusty 01

Dusty volunteers to support the Moon Dial Festival.

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Nail Polish Pt. 03

The makeup arrives and our narrator goes all the way.

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Telling Her Pt. 02

After I tell her we dress together and make plans.

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Becoming Katie Pt. 03: Real Life?

Katie’s midnight walk takes an unexpected turn.

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Room 100

Private time away turns into new life for wife and I.

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Coby Pt. 03

Adventurous suburban teen brings girlfriend to meet uncle.

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The Wife Ch. 04

Linda meets a new man with a particular taste.

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The Town Sissy Pt. 05

The town hosts its annual festival, with Rory at its center!

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4.55
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House of Seduction Ch. 04

Adam awakes with a transformed new body and mindset.

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In Over My Head Ch. 01

I was looking for a little feminine company. Who knew.

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Becoming Katie Pt. 02: Going Live

As Katie grows more confident she decides to show off online.

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The Maid Husband Ch. 02

Karuthamma marries Akhil and welcomes him to the tribe.

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Becoming Katie Pt. 01: Wardrobe

Lee discovers Katie and may never look back.

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Jennifer Nicole Goes Shopping

Jamie's sisters take Jennie shopping.

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In Love with my Roommate Ch. 02

Pierre reacts to Alexa's transitioning body.

H
4.8
5.8k
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Kinky Travels - Jessica Joins Us

Clare Invited Jessica to Play, Nikki departs the next day!

H
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Hysteria

The need we all feel inside of us, and what it drives us to.

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7k
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19
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Ch. 04 - Chastity Begins

Emerging sissy begins chastity and cum worship.

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Girlfriends Ch. 01

Post-breakup encounter in a bar - surprised by a woman.

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4.74
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Unexpected Pleasures

Trying to lose his virginity brings unexpected experiences.

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Being Sister's Dolly

Older sister helps brother live as a girl.

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Kinky Travel - Hotel Staff

Nikki Hooks Up with Jason and Clare.

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Kinky Adventures - Encore with Brian

Brian Returns for an Encore with a Friend.

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4.71
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The Making of a Sissy Pt. 05

The perfect weekend ended but there's more to come!

H
4.52
6.8k
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Neighbor: Caught in Panty Drawer

Neighbor punishes me for going through her drawers.

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28
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Jennifer Nicole Evolves

Former Girlfriend Joins Jamie's Coming Out Celebration.

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20
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Good Girl Ch. 04: Spa Day

A good girl steps out into the world for the first time.

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4.74
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Good Girl Ch. 05: The Consult

Jasmine learns where her journey leads as Summer ends.

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Needing Leah Ch. 10

It's time Leah told Ellie the truth...

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4.77
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Thorn 01

Thorn might be a pain in the butt, but he works.

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Tranned Out - The Beginning

A favor for a friend brings lucrid and lascivious surprises.

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4.71
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A Friend in Need

A friend in need is a pain in Rory's ass...

H
4.71
13.7k
27
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50
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Wingnut 01

Wingnut learns about fly fishing.

3
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Tammy Pegs Mike

After weeks of buildup Tammy pegs Mike.

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7
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21

The Evolution of Jennifer Nicole

Her sisters Melissa, Megan and Mandy Discover Nikki.

H
4.6
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16
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30
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What are the Odds?

2 wives with CD hubby's. A chance meeting.

H
4.69
13.6k
19
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42
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Lil Nicky Ch. 01

Lil Nicky is talking to you. No you, you.

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Compulsion, Control and Corruption

Dominant Daddy marks a young married man as his slut.

H
4.59
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36
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64
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Caught by the Drawer Pt. 03

The finish line might not be the end for Meaghan.

H
4.87
6k
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Sex with Married Guys Ch. 03

A married guy wears a bikini while taking cock.

4.41
6.2k
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13

Good Girl Ch. 01: Discovery

Sissy discovers herself with unexpected help from a friend.

H
4.65
26.4k
30
3
64
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crossdressing
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