‘cross dresser’ stories

Active tags
Active tags
cross dresser 

Category

My New Girlfriend

He finds a beautiful cross-dressing college boy.

4.4
103.4k
43
4
55
0

Straight to Raving Gay Sissy

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

4.39
88.6k
83
8
102
0

Another Naked Foot Day at the Beach

Foot fetish holds a Nude Day surprise at the beach.

4.39
49.5k
23
5
35
0

My Sexual Awakening - Best Friend

FANTASY is so much better than REALITY!

4.39
32.2k
27
2
52

Tales of Sub Asian Sissy Ch. 01

Jade learns a very difficult and very valuable lesson...

4.39
32.1k
37
12
49

Sisters Forever

Husband and wife becomes sisters.

0
112.4k
28
5
40

Public Cross Dressing Experience Ch. 01

Cross dresser tricked into public scenario.

4.38
117.6k
40
8
60

Highland Wedding

My best friend came out to me as being gay.

4.37
10.5k
3
0
5
0

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

Sheila and Penny

Sissies submit to their dominant wives.

4.35
83.5k
52
6
78
0

Jobe, Cross Dresser Extraordinaire

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

4.35
102.8k
22
7
28
0

The Storage Bin Ch. 02

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

4.35
35.8k
13
3
17

Str8 to Bitch Ch. 04

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

4.33
352.3k
209
55
262

Lost My Cherry To A Tranny

Tranny and Boyfriend Tag Team me.

4.32
69.5k
39
9
48
0

First Time Slut

Young man recalls his first time as a cum slut.

4.32
25.4k
23
6
47
0

Nympho Discovery, Love of Cocks

Young Man Debauched; Turns Sex Addict.

4.31
41.8k
36
5
41
0

Anal Sex with Stranger on a Train 05

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

4.29
51.3k
41
9
45

Summer Camp for Naughty Husbands Ch. 05

Stevie, the sex slave to his wife and mother in law expends.

4.28
5.3k
7
0
8

Anal Sex with Stranger on a Train 04

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

4.27
67.2k
60
2
65

Abused by a BBC

You never really know what to expect from your first BBC.

4.27
54.3k
40
4
60
0

Anneka Enjoys Cock and Fanny Ch. 03

Interludes, plus Anneka gets to fuck with Dean.

4.27
6.5k
4
2
6

A Man Has Needs

Sissy CD takes care of Sir's needs.

4.27
17.6k
11
2
16
0

Feminized at Thirty-Three

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

4.25
60k
31
8
38
0

Therapy Helps

Crossdresser exposed during therapy.

4.25
41.4k
12
5
17
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

Drawn Behind Curtains

Voyeur; Like mom, like son.

4.23
26.5k
15
0
18
0

You Got the Part!

Actor gets the role of a lifetime.

4.23
72.3k
28
8
37

The Visitor Ch. 02

A sissy subjected to domination.

4.22
52.2k
11
6
14

Hard Worker Ch. 09

Bisexual young male exhibitionist at work.

4.22
16.6k
00
1

Shylo Morra Ch. 18

Shylo learns more as a Sexual Therapist than Stripper.

4.22
2.6k
1
0
3

A Matter of Taste

Crossdressing with Barb.

4.21
94.9k
13
0
15

Twink in Sheer Cotton Underwear

Young man shares rent and learns to swallow cum.

4.21
64.4k
34
3
52
0

John D

My meeting with an assertive guy.

4.21
30.3k
6
2
6
0

Choose Your Costume Wisely

A hastily thrown together costume gets a surprise treat.

4.18
67k
9
2
15
0

The Glory Hole Surprise

Sex through a glory hole more than I planned!

4.17
136k
45
10
62
0

A Summer Storm

Two old friends get re-aquainted.

4.17
37.9k
8
3
10
0

The Applicant

Cross-dressing man gets job as female secretary.

4.16
68.2k
23
2
34
0

A Short History of Karla's Sex Life

Karla tells of her progress to sexual fulfilment.

4.15
91.7k
24
4
33
0

One Last Drag

CD gets a fresh start after breakup - 750 Word Challenge

4.15
2.8k
3
5
4
0

Hausfrau

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

4.15
56.4k
21
6
31
0

Paying Mommy’s Mortgage

Mom has to use son as mortgage payment.

4.15
445k
158
12
239
0

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

Second Thoughts

Wife helps her husband through a sex change.

4.14
195.4k
54
0
70
0

Cross Dressing for Valentine's Day

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

4.14
61.9k
12
9
18
0

Intern

Intern goes undercover as a cross dressing spy.

4.12
17k
13
0
23
0

Ensnared by a Corset

A closeted cross dresser is discovered and humiliated.

4.12
112.2k
35
9
41
0

Hard Worker Ch. 06

Young horny male exhibtionist showing off.

4.1
28.2k
1
2
2

A Good Shower

She calls and he gets ready.

4.1
71.2k
9
1
10
0

Jennifer Comes Out Pt. 01

David gets ready to go out as Jenny to look for a Dominant.

4.1
4k
3
0
7
0

Bathhouse Roles

Playing a new role at the sauna.

4.1
35.6k
16
4
16
0

Making of Alice

A make over from man to sissy.

4.09
25.2k
12
5
15
0

Waiting for My Sexy CD Slave

An afternoon with my crossdressing slave.

4.05
15.7k
6
3
11
0

Twink Role Plays Bacha Boy

Fraternity pledge coed cross dresser dances sexy for men.

4.03
15.1k
19
2
26
0

Cross Dresser Flashing for Nude Day

Flashing the sexy, pretty neighbor his pantyhose clad cock.

4.02
39.2k
11
6
13
0

Crazy Horny Obsession

Cute cross dresser waitress with enticing perfume whispers.

4.02
17.6k
13
0
15
0

College Boy Buys a Thong

This is my first time of buying thongs.

4.01
25.6k
13
0
19
0

The Maid and the Pizza Guy

Crossdressing maid and boss get a special delivery.

4.01
31.8k
10
5
17
0

Miss Rose Desperate to be Screwed

18th Century Murder, Mystery . . and Sex.

4
7k
4
1
7
0

Sex Slave on Death Row

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

3.96
27.4k
14
9
23
0

College Boy in Thong

College boy experience in girl's thongs.

3.95
24.6k
5
0
10
0

Fond Memories of My First Time

An older man fondly remembers his first man to man sex.

3.93
8.4k
6
3
8
0

My Accidental Orgy

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

3.93
24.9k
17
6
23
0

And Now I am Marcella?

Marsha forces me to do some very uncomfortable things.

3.93
44.6k
8
4
12
0

Dual Use Building Retail Strip

Hair stylists have a fetish to debauch married men.

3.92
25.8k
3
0
6
0

College Boy Cum Eater

I continue to tell of my college thong and sissy experiences.

3.91
23.1k
11
0
19
0

A Long Term Relationship

Email leads to a weekend of beautiful love.

3.91
24.5k
0000

Women's Sexual Confessions: Frances

Women talk candidly about their secret sex lives.

3.88
51.7k
10
0
13

A Strange Request...

Blackmailing my twin sister.

3.86
70.8k
47
5
74
0

Writing from Phoenix

Hot story about a cool business trip.

3.85
23.2k
4
0
6
0

Sam Meets Ms. D

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

3.84
68.5k
23
6
32
0

A New Adventure... Ch. 04

A little experimenting never hurt anyone.

3.81
10.6k
6
0
9

Fantasy Becomes Real

Cross-dresser's dream becomes real.

3.77
131.6k
8
6
9
0

The Transvestite Divorce Transcript

Likely transcript of our divorce proceedings.

3.75
14.4k
4
0
6
0

The New Whore Order

The world is starting to look a little dark.

3.73
39.2k
41
6
79
0

Anal Coed Suspended Slave

Frisky coed exhibitionist crossdresser gets first time anal.

3.7
21.8k
8
3
12
0

It's All About Sex

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

3.69
14k
3
6
3
0

Lesbian CD Sara

A CD lives with 2 lesbians.

3.56
14.9k
3
4
4
0

Online Male Crossdresser for Male

I met a crossdresser online.

3.52
7.5k
3
0
5
0

Happy New Year Ralph

Start the new year in a winter parking lot.

3.46
6.9k
1
0
6
0

Three Day Husband

Nightgown-clad husband spies on unfaithful wife.

3.2
96.2k
24
0
31
0

Using Halloween to Dress as a Queen

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

3.09
99.1k
20
11
35
0
12
Active tags
Active tags
cross dresser
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