‘crossdresser’ stories

Active tags
Active tags
crossdresser 

Category

A College Whore Pt. 03

Sean (Now named Candy) is blackmailed into modeling!

NEWH
4.64
1.4k
7
0
12
0

Keeping a Secret

After a discovery, should he keep their secret or not?

NEWH
4.85
10k
41
4
65
0

Daddy Party

A young CD accompanies his Daddy to a naughty get together.

NEWH
4.84
6.9k
25
4
40
0

Masculinity Lost Ch. 24-25

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

NEWH
4.79
4.9k
13
7
15

My BBC Neighbor

An anonymous hook-up leads to a pleasant surprise for sissy.

H
4.63
13.8k
44
5
70
0

Book Store Visit Pt. 03

Caught in the moment…No mercy!

H
4.52
4.5k
7
1
14

Mark to Maria: A coming out

MArk discovers his true self in college.

H
4.6
6.8k
10
5
23
0

Life Seems to Suck Sometimes

A Crossdresser becomes a woman with help from her friends.

H
4.63
10.2k
9
16
28
0

My Sensitive Nipples

My Longtime Enjoyment From Nipple Play.

H
4.67
2.1k
1
2
4
0

Taken Completely by Surprise

A locked, plugged, crossdressed sub confronted by cum.

4.34
5.7k
7
0
16
0

Sandy's Journey

A pair of panties changes Sandy's whole life.

H
4.83
11.9k
18
10
42
0

Tranford Tales - Carol

My husband had a bit of a turn.

4.22
1.3k
1
3
3

One Last Drag

CD gets a fresh start after breakup - 750 Word Challenge

4.07
2.4k
3
5
3
0

The Queens Secret Ch. 01

The Queen returns after a victory.

4.43
9.1k
13
1
32
0

A Gurl in the Making Pt. 01

A young man discovers more than they bargained for.

4.49
13.4k
15
2
41

Ffion and the Experiment Pt. 03

Amy enjoys taking charge of the slave.

H
4.5
3.6k
2
1
5

Babysitter's Secret...

Middle-age man hires a babysitter with a surprise...

H
4.75
15.7k
39
8
61
0

The Finder

An indecent business proposal leads to wild sex.

H
4.51
9.3k
12
2
29
0

A New Mom Pt. 02-03

A new start, a new life and a new mom.

H
4.66
18.4k
27
15
51

Passing Exams Pt. 03

Earning that 'A' with my first professor.

H
4.68
8k
11
2
20
0

Boiling the Frog Ch. 02

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

H
4.77
5k
14
6
21

Sissy Friends Forever Ch. 03

Two sissies get married and explore pleasure together.

H
4.77
3.6k
9
0
13

A New Mom

A son learns his dad is a cross dresser.

4.43
22.5k
30
14
69

Mom's Panties, Daddy's Dick

Stepdad suspects stepson wants some cock.

4.17
10.5k
8
1
30
0

Delivery Day

Young sissy girl gets more than she bargained for.

H
4.68
17.2k
31
8
52
0

The Ladyboys and Couple

Transgender ladyboys and a couple story.

4.27
4.4k
10
0
22
0

Simon and Samantha

A crossdresser finds his dream girl.

H
4.83
8.5k
26
7
42
0

Boiling the Frog Ch. 01

A woman in black drags Scott into self-exploration.

H
4.65
12.6k
26
9
49

Two Sides of the Coin

A crossdresser learns of her past, while perched on a rock.

H
4.81
5.1k
4
8
20
0

Husband Turned Sissy Pt. 01

Monica turns her husband into a panty wearing sissy slut.

H
4.58
37.6k
69
0
124
0

Lunch Break Quicky

A stranger fucks Kristy's ass on his lunch break.

H
4.57
5.7k
10
8
19
0

Playing with the Thief

Opportunity comes knocking at my door thanks to a thief.

H
4.62
10.8k
22
3
37
0

Ffion and the Experiment Pt. 02

Plans continue a pace preparing for the experiment.

4.86
1.4k
2
0
3

The Feminine Psychology of Sissies

The Homosexual Psychology of Femme Sissies.

0
3.3k
6
5
11
0

Sweet Treat Ch. 06

Crossdressing husband Stefany's first porn to camera.

H
4.5
3.3k
6
0
8

Trying It On

Nika guides her best friend, Billy, down a feminized path.

0
18.6k
33
9
66
0

Sissy Friends Forever Ch. 02

Two sissies in love work on wedding plans and having fun.

H
4.9
4.8k
12
1
17

Me From the Past

I met someone making the same mistakes as me.

H
4.68
5.4k
11
2
30
0

Sought After

An older sissy replies to an invitation to submit.

H
4.67
5.2k
10
7
19
0

Craigslist Bi TV Looking for Same

My first time dressed playing with another CD.

H
4.67
5.6k
10
1
17
0

Lucy's First Blowjob

True story of my first hook up while dressed.

H
4.51
8.2k
13
2
21
0

The Stepmother Ch. 02: Mommy's BFF

My Stepmother invites an old (famous) friend over.

4.08
7.7k
10
2
26

Frat Boy Turned - Origins

The beginning of my story discovering my submissive side.

H
4.52
26.5k
40
12
92

Sasha's First Time

A man meets CD Sasha & partner Charlotte in a bar.

H
4.87
8.4k
25
6
46
0

A Morning's Service Ch. 04

Continuing story of my new Dom and my cuckolding.

4.29
3.2k
6
1
8

Nylon Covered Thunder Cum

Crossdresser gets "caught" in the park during a storm.

H
4.7
6.2k
10
7
19
0

A College Whore Pt. 02

James takes further control of Sean!

H
4.73
11.7k
17
5
25

Taking Helen's Panties

Was it possible she knew what I did with her panties?

4.21
7.4k
6
1
15
0

Lexi's Rabbit Hole Ch. 04

Lexi’s feminization continues with first times.

H
4.79
8.6k
11
4
22

Prom Night

Three friends hope to lose their cherries on prom night.

H
4.74
23.7k
71
18
104
0

Stiletto Assassin

Black ops operative betrayed, goes deep cover for revenge.

H
4.77
6.2k
18
9
29
0

Explaining to Mommy

Crossdresser tells mother he wants to be a girl.

H
4.53
11.5k
27
4
44
0

Ffion the Christmas Elf Pt. 05

Festive Ffion fuels the fun at Christmas.

4.67
920
1
2
2

Sissy Friends Forever

Two sissies become close friends and encourage each other.

H
4.76
19.1k
38
9
74

Crossdressers First Sexual Experience

Young Crossdresser fucked by a Mature Stud.

4.36
9.4k
8
1
17
0

Careful What You Wish For - Pt. 02

The first training session.

H
4.5
14.7k
10
2
21

Big Cock Boss Pt. 02 - Intern

Prequel - Alex's virginity is taken by a sexy crossdresser.

H
4.66
8.9k
24
2
38

A Sister 'til Christmas

A T-Girl gets a surprise from her wife at Christmas.

H
4.63
14.6k
15
13
39
0

House of Seduction Ch. 14

Adam is taught by Lace how to act like a proper sissy girl!!

4.13
3.3k
00
4

Sissy In Law Pt. 02

Brian gets a taste while Hank finds a way to free himself.

H
4.56
9.9k
17
4
31

House of Seduction Ch. 13

Lace focuses on the little details Adam needs to be a sissy!

H
4.5
3k
1
0
1

Owned

An older man takes full ownership of a young crossdressser.

4.43
13.6k
22
3
36
0

Caught in the Act Ch. 02

Taking things back to his place.

H
4.78
8.3k
17
6
24

Lexi's Rabbit Hole Ch. 02

Lexi finds inspiration, dreams wet, and dresses again.

H
4.63
6.1k
12
4
16

The Intimate Dinner Party

An intimate dinner party turns erotic.

H
4.53
14.2k
31
4
55
0

The Making of a Sissy Pt. 07

Charlene and John set sail for the weekend.

H
4.56
5.7k
6
5
8
0

Absinthe and the Schoolgirl

Transgirl enjoys Girltime, a party and a little deception.

H
4.7
8.1k
5
16
18
0

The Making of a Sissy Pt. 06

Opa got Charlene ready for the yacht cruise ahead.

H
4.65
7.8k
5
1
9

The Food Court Bathroom

Saw a cockslut at the mall, and knew exactly what he was.

H
4.53
21.1k
19
3
35
0

The Twist Ch. 02

Both guys meet the lovely ladies again date 2.

4.32
3k
1
1
6

Thanks Stepmom Pt. 02 - GF?

After I learned what I am my childhood friend finds out...

H
4.67
13.3k
24
2
32

The Making of Ana

Straight man blackmailed into becoming a sissy escort.

H
4.54
29.3k
56
9
91
0

Unexpected Pleasures

Trying to lose his virginity brings unexpected experiences.

4.4
12.5k
12
4
26
0

The Making of a Sissy Pt. 05

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

H
4.55
6.9k
6
0
10

CD Transition to subwife Pt. 01

A CD is guided into full time subwife role.

H
4.58
13.8k
17
5
34

Needing Leah Ch. 10

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

H
4.77
4.6k
11
8
11

Leah, Locked Ch. 04

Leah takes the plunge with Miss Olivia and Amanda.

H
4.88
4.3k
6
1
13
Active tags
Active tags
crossdresser
Separate tags with commas. More info in the FAQ