‘crossdressing’ stories

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Active tags
crossdressing 

Category

Crossdressed and Cucked

Caught crossdressing becomes wife's girlfriend and Cuckold.

NEWH
4.5
2.7k
4
4
10
0

The Wife Ch. 05

Linda comes back for more.

NEWH
4.77
1.8k
4
0
7

A Secret Change

Mark is dressing up behind his wife’s back.

NEW
4.27
2k
3
1
6
0

Masculinity Lost Ch. 24-25

Dani gets dressed for his date and meets up with Demarcus.

NEWH
4.79
4.4k
12
6
14

Backpacking Adventure Pt. 03

Ellie takes Bobbi to a Halloween party.

NEWH
4.71
2.8k
13
1
22

An Acquired Taste Ch. 07

Erin discovers his situation may not be so bad.

NEWH
4.64
2.2k
4
0
5

Chuckie 01

Chuckie gives Quinn a free pass.

NEW
2.33
860
00
2
0

Blitzen Blue 01

Blitzen Blue addresses having three suitors.

NEW
2.33
540
00
2
0

My Visit to His House

John visits Harold's place and has a memory making idea.

4.34
4.7k
4
1
10
0

Rileys Diary: Behind bars

Riley gets drunk and makes a mistake that leads to jail.

4.43
4.2k
6
2
11
0

Panty Boys Ch. 04: The Deflowering

Mark finds out what it truly feels like to be a real woman.

H
4.76
10.4k
27
9
36

Cookie 01

Cookie has quite a couple of days.

2.17
1.5k
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1
0

Donny Gets Caught

Donny gets caught by his step-sister!

H
4.5
14.8k
19
4
38
0

Lil Fry 02

Lil Fry has a TV switch out plan.

2.33
317
00
1

Lil Fry 01

Lil Fry is famous for writing raincheck tickets.

2.25
612
0
1
2

Beanbag 06

Beanbag plans a follow up Nerds vs Geeks mixer.

3
288
000

Unwitting Twins

If you try to make your own sissy, be careful you aren't one.

H
4.56
5.8k
7
2
23
0

Penny for Your Thoughts Pt. 01

There is an opening for subjects at a research facility.

H
4.61
9.7k
26
10
48

Beanbag 05

Huh, Beanbag's rep has never been so solid.

3.67
211
000

Robin and Mark Open New Vistas Ch. 01

straight Mark and transgender Robin explore new horizons.

H
4.56
3k
0
3
8

The Golden Cage

A man gets entrapped by two attractive sex store employees.

4.48
6k
12
5
29
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Beanbag 04

Is Beanbag's rep ruined or better?

3.67
231
000

Beanbag 03

Beanbag accepts the game night invite.

3.67
534
000

Beanbag 02

Let the rep ruining continue because it works in reverse.

3
391
000

A Sissy's Long Weekend in Fairyland

A sissy's weekend experience learning from a gay Fairy.

4.18
2.6k
1
3
7
0

That Craigslist Advert 01

How did I end up doing gay porn? Here's how.

H
4.79
5.7k
25
6
37
0

More Firsts for Mark: Part 6

Mark takes his cock-lust to new heights.

H
4.6
2.7k
2
2
7

Beanbag 01

Someone tries to ruin Beanbag's rep without much success

2
736
00
1

Sandy's Journey

A pair of panties changes Sandy's whole life.

H
4.83
11.8k
18
10
42
0

Sissy Sessions Ch. 01

"Your father works so hard" - Brittany says to her son.

H
4.55
11k
34
4
55

Deeper

Stella digs deeper into dominating Max!

4.14
3.7k
2
0
8
0

Artie 01

Artie is ready for a challenge and gets one.

3
1.3k
1
0
1
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Woody 02

Woody just wanted to know who of the three names.

3.33
565
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Woody 01

Woody had it pretty easy.

2.75
1.4k
00
2

California Dreamin' Pt. 08

Spend the holidays with the ones you love.

H
4.81
2.7k
8
5
10

Shared for the Weekend

Kidnapped by my wife and shared in a community of femdoms.

4.27
9.8k
11
1
31
0

Steven, His Mum and Ex Girlfriend

Sissy Steven, his mum and ex girlfriend enjoy a threesome.

4.15
12.3k
13
0
45
0

Dipper Ch. 01

Strawberries are Dipper's thing.

3.25
720
00
2
0

Slave for The Summer Ch. 06

Tina comes over for the sleepover and the girls turn on her.

4.36
9.6k
12
7
20

Maid Serviced - 750

Guy wears a maid costume to a party and lets loose.

4.42
9.7k
7
3
14
0

Under Everyday Clothes

Plain boyfriend on the outside, lace-wearing sub underneath.

H
4.74
8.3k
14
7
32
0

Can I be your French Maid? Ch. 06

A crossdresser becomes his wife's personal French maid.

H
4.66
3.2k
8
3
10

Lil Lennie 01

This is not just another "look at me now" revenge story.

1.25
1.2k
00
3
0

Roommates Still Snowed In

The snow stops, but the roommates continue their fun.

H
4.84
11.8k
28
0
41

Can I be your French Maid? Ch. 05

A crossdresser becomes his wife's personal French maid.

4.39
2.8k
5
1
7

Can I be your French Maid? Ch. 04

A crossdresser becomes his wife's personal French maid.

H
4.64
4.6k
7
2
13

Crossdressing a Life

My adult life as a crossdresser.

4.47
5.6k
7
2
11
0

Jac E Ch. 01

There's always a commotion at Jac E's apartment complex.

2
687
1
1
2
0

Ffion and the Experiment Pt. 03

Amy enjoys taking charge of the slave.

H
4.5
3.5k
1
1
4

Echo 01

Echo supports his runner sprinter friend.

2.33
684
0000

Sissy Maid Blackmail!

A young sissy maid gets blackmailed!

H
4.61
13.7k
24
5
44
0

Dungeons, Dragons, and Dresses

My new friend takes me on a cock exploring D&D adventure.

H
4.64
5.3k
13
2
36
0

Airborne - The Search

Rory takes a flight for the first time in girl mode!

H
4.66
3.8k
9
2
13
0

Mackie 03

Mackie's adventures continue.

2
485
0
1
0

Boiling the Frog Ch. 02

A look in a mirror reveals a face Scott's never seen before.

H
4.77
4.9k
14
6
21

Sex Shop Secrets Pt. 02

Part 2 of Sex Shop Secrets: The Sissy Olympics.

H
4.75
6.2k
15
1
29

Donnie Jaye 03

Donnie Jaye kicks off the fencing project.

1.67
440
000

An Evening Of sex and Debauchery

A 3 Way orgy with 2 women and an experienced transvestite.

4.31
2.1k
4
1
6
0

Hook up site meetup

Meeting a guy from hookup site.

4.45
4.2k
3
5
10
0

A Weekend with Samantha

A Crossdresser enjoys a weekend with a girlfriend.

H
4.57
8.8k
7
0
18
0

Donnie Jaye 02

Donnie Jaye relives the inventions of the modern world.

2.33
578
00
1

Playing with The Neighbors

Sex games lead to wife swapping and crossdressing.

3.99
14.4k
18
5
35
0

Donnie Jaye 01

Donnie Jaye starts out looking for trash talk revenge.

1.8
725
000

I Want You Inside Me Ch. 03

End of One Journey and just the beginning of another.

H
4.7
6k
6
1
8

Miggie 02

Miggie pedals pizza slices without pedaling.

1.67
460
00
1

My Sissy Awakening 03

My anal training intensifies, there's no going back now.

H
4.59
9.6k
18
3
22

Miggie 01

Miggie uses a bike for leg exercise.

2.33
1k
000

Lil Money 01

Lil Money wins a challenge, but loses innocence.

1.8
982
00
2
0

Mackie 02

Mackie has his trucks tires rotated at the Tire Shop

1
705
000

Q Tip Ch. 01

One bad hair day and you're Q Tip forever.

1.57
1.1k
0
1
1
0

Mackie 04

Mackie had nothing to do with the babysitters wait list.

1.8
552
000

Congi Que 04

Congi Mom's and a Congi night at the Goth club.

1.8
339
000

California Dreamin' Pt. 07

Jack goes home for Christmas.

H
4.8
5.6k
7
5
12

Congi Len 04

Congi Len still collects $10 bills at the goth club

1
276
000

The Hottie in the Mirror Pt. 02

Alex begins to lose his slippery grip on his masculinity.

H
4.84
18.4k
42
16
67

A Futas Guide to Sissification

A short guide to training the perfect little sissy.

4.24
19.6k
15
2
36
0

F-150 Pt. 02

I service BD and his buddy at remote cabin in the woods.

H
4.74
4.3k
17
3
20
0

Mackie 01

Mackie goes to a birthday party in a babysitter look.

2.6
2.5k
2
1
4

Simon and Samantha

A crossdresser finds his dream girl.

H
4.83
8.4k
26
7
42
0

Wife Takes Control He Takes It Back

Wife takes control of couples sex life and Husband responds.

4.1
10.5k
20
5
31
0

The One Night Stand Ch. 04

One year anniversary of Riley being trained.

H
4.74
9.3k
8
0
19

Congi Bar 04

Congi Bar needs a perfect date for a Congi Len pizza party.

2
377
1
0
1

Lingerie on a Hot Afternoon

Charlotte finds a thrilling scene when she comes home early.

H
4.75
17k
27
11
48
0

Bring out her Wild Side Ch. 02

Lori Beth continues her wild weekend.

3.24
7.5k
7
0
14

Congi Len 03

Congi Len is still gathering up $10 bills.

2.33
313
000

Here We Go Again

About to get another spanking.

4.27
4.3k
1
0
5
0

Boiling the Frog Ch. 01

A woman in black drags Scott into self-exploration.

H
4.65
12.5k
26
9
49

Slave for The Summer Ch. 05

Vicky torments Josh in public during their trip to the mall.

H
4.51
12.9k
13
9
30

Chocolate Box

His wife's Valentine's surprise is his forced feminization.

4.47
29.9k
47
21
89
0

California Dreamin' Pt. 06

Jack’s Halloween costume turns into something more.

H
4.95
6.7k
11
7
19

Mistress Cruel Love Ch. 05

Markus' feminization begins. He gives all and gets nothing.

H
4.53
6.9k
2
0
8

BBC University

A young white boy at the Big Black Cock University.

H
4.54
9.2k
22
2
40
0

Fishnets / French Maid - Proposal

Dakota kinda proposes during threesome (750 Word Challenge)

4.13
2.6k
6
2
16
0

Lil Joey 03

Just another Friday night on the Strip for Lil Joey.

2.75
431
00
1
Active tags
Active tags
crossdressing
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