‘crossdresser’ stories

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Active tags
crossdresser 

Category

Friends of Friends Pt. 02

Jack and Marcus finish up the night with Terry.

H
4.68
6k
3
1
7

The Robertson's Sissy Ch. 18

Matt takes last step to feminization.

H
4.76
17.4k
11
0
18

Lindsey and Louise Pt. 02

Louise finds delight in Thompson.

4.44
5k
4
1
6

Breakdown

How to fix a car with a pair of 5" heels and a short skirt.

4.44
15.2k
16
3
18
0

Jack's First Time

Jack's wife gives him permission to experiment.

4.36
33.5k
19
6
29
0

The Transition Ch. 03: Aftermath

Mark has to figure out where to go from here.

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4.71
13.5k
12
8
16

This is What I was Meant to Be

Jacob can't take it anymore! He needs to be dominated.

4.37
18.6k
23
2
28
0

Lulu's Lockdown Diary

White boy is stuck at home with two big black studs.

H
4.65
47.8k
109
4
152
0

The Businessman's Urge for Men

A stressed businessman deals in hot male ass.

4.45
10.1k
6
0
12
0

Halloween Hijinks

Halloween leads a man to try crossdressing and they love it!

H
4.65
33.9k
55
9
69
0

Hilton Hottie

CD has fun on a business trip.

H
4.59
16.4k
13
0
19
0

Hotel Gangbang Ch. 01

Part one of a CD/TV and admirer gangbang.

3.69
14k
11
2
14
0

The Transition Ch. 02: Jamie

Jamie has to decide if he will crossdress for sex.

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4.69
20.4k
21
2
30

Family secret Ch. 02

My cousin and I take things to the next level.

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4.54
16.6k
12
5
18

Magic Dress - Veronica

My Auntie's dress really helped me.

4.47
13.5k
4
1
13

The Transition Ch. 01

Man decides to create a transsexual GF.

4.33
30.1k
37
5
53

Helping a Roommate

Brandon walks in on his roommate dressed in women's lingerie.

4.42
34.2k
28
5
42
0

Sandy's First Time - Climax

Sandy and Chanel finish what they started!

H
4.63
7.3k
6
2
7

Barbie's BBC Beginning

A sissy husband gets roped into interracial sex by his wife.

H
4.64
163.2k
241
30
336
0

The Porn Chase Pt. 01

A lap dance with a laptop.

H
4.6
5.8k
4
2
9

Crossdresser Crosses Over for Good

Crossdresser's first time with a real man.

4.06
36.8k
6
6
9
0

Neville

Crossdresser gets corporal punishment.

4.24
9k
5
1
9
0

A Friendly Neighbour

Crossing dressing with a neighbour and more.

H
4.5
24.6k
19
4
25
0

One for the Team Ch. 09

End game... what really happened to Charlotte Ward?

H
4.7
8k
10
11
12

One for the Team Ch. 08

Archie and Sandra piece together what happened to Charlotte.

H
4.8
5.9k
6
5
7

One for the Team Ch. 06

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

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4.77
7.3k
6
3
6

Jasmine - Sissy Slut Transformation Pt. 01

A young man's transformation into a sissy whore.

4.32
76.2k
68
2
114

One for the Team Ch. 03

Robert wants Charlotte all for himself so he can defile her.

H
4.83
12.6k
17
5
19

First Time Sissy - The Bike Path

First time sissy decides to go for a walk.

4.38
24.4k
17
3
28
0

One for the Team Ch. 01

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

4.49
25.9k
30
4
60

The Man in the Red Dress

That one photo you forgot was on your dating profile.

4.5
2.8k
3
1
5
0

For Their Pleasure Pt. 04

A new client of Alexis has a familiar face.

H
4.77
10k
11
4
16

Expectations be Damned

A shy young man is in for a night of seductive surprises.

H
4.64
38.3k
56
7
85

Yeliza Awakens Pt. 02

Girlfriend mistress fucks her sissy silly.

H
4.51
14.7k
9
2
10

Forced to Dress

Girlfriend takes revenge on boyfriend for cheating on her.

H
4.7
64.3k
78
17
111
0

Womanly Pleasures Ch. 01

Two men live as women with pleasurable results.

4.37
18.5k
11
2
18
0

Forced To Have Sex As A Girl

Crossdresser Enjoys Intercourse As A Girl.

H
4.5
67k
26
7
40
0

Blue Diamond

The female Buffalo Soldier you never heard of.

4.34
5.9k
1
0
4
0

CD Asst. Secy. Ch. 05: 1 yr. Later

Follow up from last story with something before it.

4
4k
000

Amelia Jones Ch. 01

Wife is brought into husband's transsexual fantasy

4.48
25.5k
18
7
38
0

Newbie In Baseball Team

Newbie gets gangbanged by his teammates.

4.02
27.1k
16
0
29
0

Family secret

'Becky' reveals herself to her cousin.

4.47
31.7k
25
5
38

Magic Dress - Isis

A happy day for a feminine man.

4.41
9.1k
2
6
5

My Sweet Sissy

A mommy writes to her sissy.

4.19
17.4k
15
7
27
0

Jerry becomes Jill Pt. 05: July 4th

We go to the beauty parlor and to a party...

4.42
17.7k
14
7
20

Alexis' First Time Ch. 02

Meeting with a friend for some fun.

H
4.81
13.3k
16
3
17

First Shemale

Daddy finds his Shemale.

4.34
20.9k
16
0
17
0

Son Gets "Punished" by Mom

Mom finds out about her crossdressing son.

3.71
61.2k
45
8
90
0

Jerry becomes Jill Pt. 04a: Doctor

Jerry gets female hormones and a visit to the doctors...

H
4.51
19.8k
15
0
22

CD Asst. Secy. Ch. 01: End and Start

Internship ended and I officially became asst. secy.

3.83
10k
5
0
7

CD Internship Ch. 08 - Twists & Turn

Many twists with a sad turn but a happy end.

4.3
3k
0
1
0

My First Ladyboy

Straight alpha male falls for a sexy Filipino ladyboy.

4.41
38.2k
28
7
43
0

A Slut is Born

A young man is corrupted by porn and becomes a cock slut.

4.46
48.8k
36
4
59
0

CD Internship Ch. 05 - More Feminine

Increase in femininity before the storm.

3.21
5.3k
000

The Trap Ch. 05: A Proposal

Paula's old life crumbles and a new one opens up.

H
4.68
8.2k
12
8
13

Sir and Faggot

A May December romance.

4.31
11.7k
2
0
6
0

Birth of a Rose

Mature man is feminized and submits to a Mistress.

H
4.51
29.3k
32
4
45
0

Alexis' First Time Ch. 01

Shy crossdresser finally gets first time.

H
4.65
39.3k
41
16
68

Danny to Danielle - Beverly Awakened Pt. 02

Beverly accepts desires; Danny fears the worst is best.

H
4.66
10.5k
14
4
15

A Dream Come True - The Adult Theatre

A crossdresser's dream comes true at the adult theatre.

H
4.7
44.2k
47
11
68
0

Crossdressing, Piss and Sex

Blindfolded, pissed on and fucked by multiple men.

H
4.7
28k
25
11
50
0

Mistaken Identity Ch. 02 - the Second Cummin

More crossdressed sex after being forced earlier.

H
4.68
10.9k
14
2
21

Mistaken Identity Ch. 01

A crossdresser's fantasy comes true.

H
4.57
28.7k
28
3
41

Slut on Screen

Shemale is the star of a gangbang movie.

4.27
12.8k
12
4
13
0

My Promise to Squirt for Dan

Danny made me promise him something one night.

4.49
25k
13
0
17
0

Boredom Forces Me to Take a Chance

Crossdresser goes out in public and accidentally scores!

H
4.78
20.3k
29
9
43
0

The Tree Man saw me!

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

4.47
23.5k
28
7
39
0

Becoming a Girl for My Step Brother

Step brother has sex with step sister and learns her secret.

4.28
61.1k
34
4
66
0

My Doctor Helped Me Become a Girl

Taking hormones and becoming a wife.

4.46
52.4k
39
8
63
0

The Women's Spa - Almost

I visit an all female spa with a little difference.

4.46
23k
18
11
32
0

How a Wife Keeps Her Husband Happy

Crossdresser housewife wedding anniversary threesome.

4.42
39.2k
19
4
35
0

CD Internship Ch. 03

Becoming Leona and driver cum assistant secretary as well.

4.46
6.2k
2
0
2

Caught in Pink: A Sissy Story

A Sissy is caught and blackmailed by a mysterious co-worker.

4.49
40.5k
31
7
51
0

My Name is Raquel Ch. 07

Jessica's second surprise for Raquel.

H
4.69
8.2k
9
3
12

CD Internship Ch. 01 - Caught and Paraded

Getting caught in my skirt at work and the new beginning.

4.03
19.5k
13
2
18

Magic Dress - Clarrie

A man, a crime, a dress, a deep desire.

4.41
9.3k
3
1
11

A Biker Became My Daddy

A young sissy becomes the girl he has always wanted to be.

4.45
78.8k
107
9
155

Mike the Gang Bang Bitch

A quick hookup turns humiliating for Sissy Mike.

H
4.53
48.7k
42
3
64
0

A Sissy's Walk in the Park

A walk in the woods becomes a dream come true for a sissy.

H
4.68
38.3k
46
2
68
0

Crossdressing Days 03: Sendoff Day

Story of crossdressing in saree for the sendoff day.

4.08
7.9k
2
0
2

Delilah

An almost 750 word project entry.

4.04
10.1k
1
15
3
0

The Flaming Girls Ch. 02

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

H
4.66
5.9k
6
3
7

Crossdressing Days 01: Teachers' Day

Story of myself dressing in a saree on teachers' day.

4.25
21.7k
16
2
17

My Name is Raquel Ch. 05

Raquel's first "Girls' Night Out".

H
4.8
11.5k
11
10
15
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Active tags
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crossdresser
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