‘cross dresser’ stories

Active tags
Active tags
cross dresser 

Category

A New Adventure... Ch. 03

A little experimenting never hurt anyone.

4.14
16.3k
9
0
10

A New Adventure... Ch. 02

A little experimenting never hurt anyone.

4.14
19k
11
0
14

A New Adventure...

A little experimenting never hurt anyone.

3.58
54.7k
20
4
29

Sex Slave on Death Row

Sex slave on death row--my prison blue balls.

3.96
27.4k
14
9
23
0

A Photo Session, My First

A sissy 'girl' gets put on display, for offer to others.

H
4.53
85.7k
63
4
91
0

Hausfrau

Gerrig wakes up with his penis on a leash, he's a housewife.

4.15
56.4k
21
6
31
0

Nympho Discovery, Love of Cocks

Young Man Debauched; Turns Sex Addict.

4.32
41.8k
37
5
42
0

Bullding a Greater Family

A different look at building a successful family.

H
4.72
48.1k
56
10
71
0

Sissy Blane's Liquid Assets

A sissy must work off his debt to a sex clinic.

4.24
30.7k
14
2
21
0

Straight to Raving Gay Sissy

Married man role plays at adult rave party; swallows cum.

4.38
88.3k
81
8
99
0

Names Can Be Deceiving

A handyman gets it wrong when things get steamy with Jamie.

4.47
28.3k
17
2
19
0

Drawn Behind Curtains

Voyeur; Like mom, like son.

4.23
26.5k
15
0
18
0

Lost My Cherry To A Tranny

Tranny and Boyfriend Tag Team me.

4.3
69.5k
38
9
47
0

Twink in Sheer Cotton Underwear

Young man shares rent and learns to swallow cum.

4.21
64.3k
34
3
52
0

My Accidental Orgy

A Transwoman, hunting for a mate, stumbles into an orgy.

3.93
24.9k
17
6
23
0

Lesbian CD Sara

A CD lives with 2 lesbians.

3.56
14.9k
3
4
4
0

Sheila and Penny

Sissies submit to their dominant wives.

4.36
83.4k
53
6
78
0

Feminized at Thirty-Three

A man in his thirties realizes the power of his inner woman.

4.25
59.9k
31
8
39
0

Quinn Ch. 03

Quinn gets a scare before some alone time with Josh.

H
4.67
21.2k
14
5
16

Becoming Mindy Ch. 03

Mindy starts taking some big steps on her path to ...

H
4.56
36.2k
18
5
19

The Visitor Ch. 02

A sissy subjected to domination.

4.21
52.2k
11
6
14

Bathhouse Roles

Playing a new role at the sauna.

4.1
35.6k
16
4
16
0

Sam Meets Ms. D

Sam finds a job opening online. Learns a hard lesson.

3.84
68.5k
23
6
32
0

Danielle's Transformation Ch. 02

Danielle finds she's getting more than she bargained for.

H
4.51
59.2k
32
10
37

Ensnared by a Corset

A closeted cross dresser is discovered and humiliated.

4.12
112k
35
9
41
0

Pitching a Tent for Three

Friend joins couple on a romatic camping getaway.

4.42
79.5k
46
5
66
0

The Glory Hole Surprise

Sex through a glory hole more than I planned!

4.17
135.6k
45
10
62
0

Anal Sex with Stranger on a Train 05

Peter officially meets Roberta again, the love of his life.

4.28
51.3k
41
9
45

Anal Sex with Stranger on a Train 04

Peter calls Robert for anal sex to finish what he started.

4.27
67.1k
60
2
65

Anal Sex with Stranger on a Train 03

A man has anal sex on a train with a stranger.

4.18
157.7k
79
13
87

Choose Your Costume Wisely

A hastily thrown together costume gets a surprise treat.

4.18
66.9k
9
2
15
0

Brotherly Desires

A visit from the neighbour leads to fun for two brothers,

H
4.51
69.9k
55
7
71
0

You Got the Part!

Actor gets the role of a lifetime.

4.22
72.2k
28
8
37

Therapy Helps

Crossdresser exposed during therapy.

4.25
41.4k
12
5
17
0

John D

My meeting with an assertive guy.

4.21
30.3k
6
2
6
0

The Maid and the Pizza Guy

Crossdressing maid and boss get a special delivery.

4.01
31.8k
10
5
17
0

Robin and Mia

Rob is forced to become Robin.

4.45
103.3k
50
12
64
0

Cross Dresser Dominated Ch. 01

Internet ad leads to fantasy realized.

3.66
31k
5
4
6
0

Another Naked Foot Day at the Beach

Foot fetish holds a Nude Day surprise at the beach.

4.39
49.4k
23
5
35
0

The Law of Attraction Ch. 07

Ashley's Story: Let the healing begin.

H
4.79
15.2k
7
2
8

Fantasy to Reality Ch. 02

A sissy's fantasy becomes a reality.

4.45
87.5k
26
9
33

Public Cross Dressing Experience Ch. 01

Cross dresser tricked into public scenario.

4.38
117.4k
38
8
57

A Summer Storm

Two old friends get re-aquainted.

4.19
37.9k
8
3
10
0

Desiree and Big John

The hot to trot transvestite gets her first real man fuck.

4.46
42.8k
20
5
24
0

His Sissy Boy

A very dominant man uses his sissy 'wife'.

4.4
373.3k
165
21
207
0

Cross Dresser Flashing for Nude Day

Flashing the sexy, pretty neighbor his pantyhose clad cock.

4.02
39.2k
11
6
12
0

Surprise!

Surprising my straight hubby with a bi guy in drag.

H
4.55
106k
62
15
70
0

The Office Halloween Party Ch. 01

A joke costume goes a little too far, or not far enough.

H
4.55
205.8k
184
25
240
0

Hard Worker Ch. 09

Bisexual young male exhibitionist at work.

4.22
16.6k
00
1

Cross Dressing for Valentine's Day

Man attends his first cross dressing Valentine's Day party.

4.14
61.8k
12
9
18
0

Sisters Forever

Husband and wife becomes sisters.

0
112.3k
28
5
40

Using Halloween to Dress as a Queen

Jerry uses Halloween as his excuse to dress as a woman.

3.11
99k
20
11
35
0

Sabbatical or Continuous Gang Bang? Ch. 02

Rick and I spend the rest of the day on into the night alone.

H
4.72
58.5k
51
2
55

Sabbatical or Continuous Gang Bang?

I took some time off from college to dress up and get wild!

H
4.69
116.9k
111
6
128

Hard Worker Ch. 06

Young horny male exhibtionist showing off.

4.09
28.2k
1
2
2

Str8 to Bitch Ch. 04

Drew thinks he's escaped Mark, Drew is wrong.

4.33
352k
208
55
261

Was He Becoming A Cross Dresser Ch. 04

Dressing as a woman in secret, how far would he go?

0
48.4k
10
5
10

It's All About Sex

Everything in life is about sex. Isn't it?

3.69
14k
3
6
3
0

Women's Sexual Confessions: Frances

Women talk candidly about their secret sex lives.

3.88
51.7k
10
0
13

Secret Life of a Slut!

How one man changed from straight to a cock slut.

4.41
116.5k
46
12
52
0

Writing from Phoenix

Hot story about a cool business trip.

3.85
23.2k
4
0
6
0

Paying Mommy’s Mortgage

Mom has to use son as mortgage payment.

4.15
444.5k
159
12
237
0

Stud Bitch Ch. 02

A guy in pretty lingerie does his first BJ.

H
4.53
75.5k
13
6
16

Mandy Has Fun With Eddie

Bi transvestite has fun with hunky Eddie.

4.38
38.8k
6
5
9
0

My New Girlfriend

He finds a beautiful cross-dressing college boy.

4.4
103.3k
43
4
55
0

The Applicant

Cross-dressing man gets job as female secretary.

4.16
68.1k
23
2
34
0

Her New Girlfriend Ch. 02

Transition: the morning after.

4.47
180.4k
47
5
53

The Storage Bin Ch. 02

Weekly dress-up game turns into a hot encounter: continued.

4.35
35.8k
13
3
16

Chrissy Grows Bolder

Crossdresser goes out dressed to meet a man.

H
4.62
65.8k
18
8
18
0

A Cross Dressing Suck Off Fantasy...

Man on business meets sexy cross dresser.

4.42
158.8k
19
10
24
0

A Short History of Karla's Sex Life

Karla tells of her progress to sexual fulfilment.

4.15
91.6k
24
4
33
0

Second Thoughts

Wife helps her husband through a sex change.

4.15
195.3k
54
0
69
0

Fantasy Becomes Real

Cross-dresser's dream becomes real.

3.77
131.5k
8
6
9
0

Sniffer and the Hotel

submissive cd slut meet with two bisexual guys.

4.48
69.9k
4
4
6
0

How I Became Sissy Willow Ch. 01

Married cross-dresser's fantasy is to dress & serve.

4.42
203.3k
65
17
77

Jobe, Cross Dresser Extraordinaire

To get dream dyke, he pretends to be a she.

4.36
102.7k
21
7
27
0

A Long Term Relationship

Email leads to a weekend of beautiful love.

3.91
24.5k
0000

A Matter of Taste

Crossdressing with Barb.

4.21
94.9k
13
0
15

Marilyn's Sexual Paradise

Marilyn & Kat go off on a Hawaii honeymoon.

H
4.79
50.4k
12
1
15

Marilyn's Family Reunion

Marilyn gets reunited with her lover, possibly forever.

H
4.55
41.9k
12
0
12

Three Day Husband

Nightgown-clad husband spies on unfaithful wife.

3.2
96.2k
24
0
31
0
12
Active tags
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cross dresser
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