‘crossdressing’ stories

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Active tags
crossdressing 

Category

Down The Rabbit Hole Pt. 02

Follow Alex as he finally lives out his feminisation fantasy.

H
4.75
8.8k
13
1
21

Sissy's Online Mistress Ch. 01

I fall deeper into an online feminization rabbit hole.

H
4.57
20.4k
34
7
70
0

An Evening in the Garden

My crossdressing journey continues in a neighbour's garden.

3.2
4.4k
3
0
5
0

The Second Day of Spring Break

Day two of our spring break adventure. A new development.

4.2
10.2k
5
1
11
0

The Chance Fantastic Pt. 05

Sissification turns a young man into a seductress.

H
4.8
6.1k
11
7
17

Afro Stress Relief Ch. 14

Whiteboy visits Beatrice in Las Vegas.

H
4.59
3.8k
8
6
11

S(m)ister Wife Pt. 02

Tourist is kidnapped to be a sister wife.

H
4.59
20.5k
15
8
23
0

A Model for the Night

A first night crossdressing for a man with a camera.

4.31
6.3k
7
3
16
0

Caught in Her Underwear

A husband succumbs to his lingerie urges.

H
4.69
17.8k
23
13
30
0

The New Flatmates Pt. 02

Kristy visits the flat meets the rest of the occupants.

H
4.61
4.7k
3
3
7

The Cabin Ch. 02

Two more travellers find solace and more within my refuge.

H
4.73
10.6k
15
4
25

I Encouraged My Wife to Date

Crossdresser shares his wife with another man.

4.12
11.8k
17
5
28
0

Groped at Anime Convention Pt. 02

Man meets molestor again and is forced to do more things.

H
4.62
21.7k
39
8
48

Easy Female Transition

Transition to female and then to loving wife.

H
4.56
18.8k
18
8
34
0

Meeting Mistress Mercy

My first time with my new Mistress.

H
4.76
26.9k
28
6
80
0

Full Engine

A shy boy falls for his busty coworker.

3.73
23.2k
13
2
33
0

Away from Home Fun

A crossdresser gets more than they bargain for in a hotel.

H
4.5
18.2k
18
3
33

The Cabin Ch. 01

I stumble upon a cabin containing more than I anticipated.

4.33
24.2k
30
10
56

Brix 01

I'm Brix, either way we meet.

2.88
1.3k
00
1
0

Cam 01

Cam loses a piece of his forbidden fruit.

3
1.5k
00
1
0

Snowed in with Aunt V Ch. 02

Aunt V catches Kelly in a dress.

H
4.55
27.1k
45
8
61

Marti 01

Marti works for a meal delivery service.

2.33
2k
000

Angel from the Ashes

Two long term friends discover they want to be more.

H
4.76
7.1k
18
12
29
0

Rory, the Reward

Rory has been many things, but never the reward itself!

4.41
9k
10
1
18
0

Binkie 01

Binkie needs things cleared up.

2.8
1.3k
1
0
2
0

Journey to Girlhood Ch. 01

Steve begins a journey after an encounter with a bully.

H
4.62
48.5k
91
12
169

Caught with My Stepsister's Clothes Pt. 03

My first all girls sleep over and my first cock cage.

4.48
22k
27
8
45

The Chance Fantastic Pt. 04

The action heats up as our sissy starts to get some attention.

H
4.64
3.1k
5
1
6

Lesley and Kerry Ch. 03

Lesley is seeing much more of Kari as they search for lovers.

H
4.82
7.1k
19
6
36

Mikki 02

Mikki's evening continues at Ironsides.

2.75
1k
1
0
1

Mikki 01

Mikki helps Jacob select an outfit to wear.

3.38
3.7k
1
0
3

Caught with My Stepsister's Clothes Pt. 02

Things progress to a new level with a new name & experience.

H
4.64
29k
30
5
48

Pantyhose Cuckold Pt. 01

Hubby's curiosity gets the worst of him.

H
4.53
32.2k
53
11
81

Groped at Anime Convention Pt. 01

Man goes to anime convention crossdressing and is molested.

4.31
29.8k
48
10
92

First Hotel Experience

Novice crossdresser ventures out into the world.

H
4.55
6.7k
9
7
13
0

A Mad Tea Party

A costume contest leads James to discover his femininity.

H
4.77
18.2k
28
13
56
0

Sissy in Vegas

What happens in vegas turns a sissy out of a femboy.

H
4.72
38.4k
87
22
144
0

Snapdragon 01

Snapdragon leads to his own first time.

2.78
1.7k
2
0
4
0

So Sue Me Pt. 03 - Final

Dave and Sue team up to give the whole family a happy ending.

4.28
5.8k
12
0
21
0

Trick Cee 01

Trick Cee is a themed based CD.

2.78
1.5k
1
0
2
0

So Sue Me Pt. 02

Dave has reconnected with his sister. But Josh objects.

4.45
4.7k
10
0
14

T-Bar

My roommate convinces me to go to a new bar.

H
4.85
38.6k
95
17
142
0

The Unlocked Door

A 20 year old is caught crossdressing by his mother - No sex.

4.38
10.1k
7
10
15
0

Homeless and Desperate

Femboy is homeless and forced to submit to a man for a bed.

H
4.52
43.7k
63
20
108
0

Donnie 01

Donnie trades chit chatting for yip and yapping.

1.88
2.4k
000

So Sue Me Pt. 01

A follow-up to Dave's Gay Experience.

4.29
7.2k
11
1
17

Afro Stress Relief Ch. 11

Whiteboy attends Harvey's barbecue.

4.44
4.4k
9
6
11

Jitter 01

Jitter's neighbor has a train wreck going on.

3
2.5k
0000

The Red Panties Test Pt. 05

Nikki makes a mess of her first day in makeup for Daddy.

H
4.79
8.6k
10
5
14

Andy Comes Home

Andy comes home to his Dad.

H
4.77
49.6k
56
13
107

Gordo 01

Gordo has a hidden treasure map.

2.67
1.7k
1
0
1
0

Dizzy 01

Dizzy pulls together a championship game watch party.

1.64
2.3k
0000

Lil Bit 02

Lil Bit has an after party and recreates a meme.

2.2
1.4k
1
0
1

Dragonfly 02

Well, the Devil's Den spot had caves, so.

2.83
985
2
0
2

Lil Bit 01

Lil Bit has a little bit of during a drive.

1.88
1.9k
1
0
1

Poochie 01

A sprain ankle is tended to.

2.33
2.5k
0
1
00

Dragonfly 01

Dragonfly wants to go to the Devil's Den spot.

2.5
1.2k
1
0
1

The Rise of Rachel Price T-Girl Pt. 03

Practice Run: Rachel must walk in the hotel by herself.

H
4.6
7.3k
11
4
17

Brownie 03

Brownie gets rescue, but in only four articles of clothing.

2.6
1.3k
000

The Chance Fantastic Pt. 03

Solo exploring leads to real life discoveries.

H
4.5
2.8k
6
0
6

Hallowiener Pt. 09

Dani's long night is not quite over yet.

H
4.72
8k
16
1
23

Brownie 02

Brownie gets caught in a selfie outfit.

3.25
1.8k
1
1
1

Brownie 01

Brownie net skims the pool next door.

2.71
3.5k
1
2
2

QT Rikki 01

QT Rikki's first trip up to the Witches Rocks Circle.

2.33
1.1k
1
0
2
0

Afro Stress Relief Ch. 10

Whiteboy meets Tammy's 'rough boys'.

H
4.62
3.8k
9
5
11

A Crossdresser and an Exhibitionist Ch. 02

Two new partners in crime form their alliance.

4.44
3.1k
4
0
8

Darla gets a Makeover and Pegging

Susie gives us a makeover and Watches Mistress Peg me.

4.44
9.9k
5
2
15
0

Dori-Dore 01

Dori-Dore prepares for the upcoming storm.

2
1.8k
0
1
1
0

T-Vie 01

T-Vie feeds the roomie, her boyfriend and Luke.

2.4
1.8k
1
0
1
0

Dilly 02

Oh, so there are still more college bowl games then?

1
1.3k
000

Crossdresser Needs Her Couch Moved

Crossdresser asks stranger to help move her couch.

H
4.59
13.3k
12
4
16
0

Afro Stress Relief Ch. 09

Whiteboy attends the Beer Bust.

H
4.83
4.5k
12
9
17

Caught with My Stepsister's Clothes

I was caught with my stepsister’s clothes and forced...

H
4.62
48.1k
80
12
148

Dilly 01

Dilly enjoys college football bowl season, a little too much.

3.22
2.3k
2
0
3

Doppelgänger

An exact double, crossdressing fantasy, and a sexy prank.

H
4.57
6.9k
7
2
13
0

The Restart Pt. 02

Becky finds out about Chrissy's other life.

H
4.72
7.8k
12
2
14

Coconut 02

Coconut hides out at the mall and runs into Zack and Juju.

3
1.1k
000

National Hall Pass Day

Teacher first time using his Hall Pass on a student.

4.42
10.4k
24
5
40

Coconut 01

Coconut didn't think of himself as just a tease, but maybe.

2.5
2.2k
000

Caught by My Boss Pt. 03

Andy gets more comfortable slipping into his role as Andi.

H
4.74
15.5k
27
4
38

The Rise of Rachel Price T-Girl Pt. 02

Charlie experiments and transforms Denver into new Rachel.

H
4.62
11.3k
17
7
22

Bait and Switch Ch. 01

Shrunken to 3 ft tall, wanting a giantess, owned by a giant.

3.79
9.3k
7
1
11

Dave's Gay Experience Pt. 01

Dave's nephew shows him the pleasures of same sex relations.

4.39
18.6k
22
2
43

The Process/Progress Pt. 03

Seduced brother is confronted by sister.

H
4.79
14.6k
22
13
32

Camila and the Halloween party

Camila convinces me to go to a Halloween party dressed up.

H
4.74
44.6k
57
6
103
0

Once a Bully, Always a Bully… Pt. 05

Preparing for anal is going well, but a mistake is made.

4.36
17.8k
12
3
17

Graduation Weekend 01

It was a graduation weekend on the coast at the resort.

4.22
4.1k
2
0
3
0
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Active tags
Active tags
crossdressing
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