‘crossdresser’ stories

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Active tags
crossdresser 

Category

A Shemale Vacation Ch. 02

Now it's him that has to be the whore.

H
4.58
128.6k
67
7
77

Finishing School For Ladies Ch. 01

Transvestite hides in ladies finishing school, sex ensues.

H
4.54
44.5k
66
8
99

A Favor from a Friend

I ask my best friend to let me give him a blowjob.

H
4.66
33.1k
66
18
92
0

A Weekend Away Ch. 01

A very special b-day present for sissy, from her wife.

4.39
59.3k
66
8
107

A Sissy Gets Hooked

A Sissy gets deeper and deeper into her hooker fantasy.

H
4.74
27k
65
11
102
0

Crossdressing Son and Dad Pt. 03

Dad finally finds out the truth.

H
4.69
51.5k
65
5
99

Camming Down the Rabbit Hole Ch. 12

It’s getting very messy, but it's all building to a finale.

H
4.89
38.8k
65
78
76

A Wife Comes Around Ch. 03

A wife helps out with his fantasy.

H
4.61
110.4k
65
16
75

College Sissy's First Time

A drunken college sissy gets what she was craving.

H
4.75
53.5k
65
8
120
0

Trapped and Trained Ch. 12

Candi learns how to be a real slut.

H
4.61
215.4k
64
6
81

New Mother, New Life Pt. 01

Crossdresser re-unites with birth mother.

H
4.6
67.4k
64
4
83

Micheal Finds Jamie

Straight guy finds his buddy all dolled up and gets some.

H
4.54
43.5k
64
8
74
0

Pillow Talk Ch. 01

Cop is forced to go undercover as a transvestite hooker.

H
4.5
44.4k
64
5
92

Eric Becomes Erica Ch. 01

Robert catches his son, Eric, watching transsexual videos.

H
4.53
43.4k
64
7
85

The Birthday Party

A 30 year old loses his virginity to three men.

H
4.5
68.9k
63
8
79
0

Keeping a Secret

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

H
4.84
16k
63
8
97
0

A Christmas Surprise

My wife finds my secret and embraces it for the holidays.

H
4.59
55.4k
63
11
81
0

Janie's Got a Dildo

Sister abuses her cross-dressing step-brother.

4.19
207.8k
63
5
100
0

I Need to Lose More Bets

Husband enjoys first time as crossdresser after losing wager.

H
4.54
75.1k
63
14
80
0

Lost Luggage

When your luggage goes missing, you wear a dress.

H
4.56
181.8k
63
21
82
0

Queen of Paradise

Couple checks in seashore resort and get lots of surprises.

H
4.61
48.3k
62
8
79

Sissy's Subservience to Wife Ch. 01

Hotwife transformed me into a sissy cuckold.

4.32
100.3k
62
14
93
0

I Got Caught in Girls Underclothes Ch. 02

Sis torments me with the one thing I couldn't get for myself

H
4.54
92.5k
62
6
74

Once Upon a Laundry Ch. 01

A crossdresser is caught with panties in the laundry room.

H
4.56
49k
62
14
83

Prison Sissy Cuckboy Ch. 01

Beta bitch joins a gang as a sissy cuckboy.

H
4.53
34.3k
62
7
109
0

Her First Halloween Ch. 02

David goes further than he thought he could.

H
4.61
74.4k
62
7
88

Prom? Ch. 04

Prom night! Blackmail, blowjobs, and more for Anna!

H
4.74
60.8k
62
9
74

A Day on the Water

Mia is invited out for a boat ride by an older man.

H
4.72
25.7k
62
29
86

Storage Unit Discovery

I learn the pleasures of lingerie from a storage unit.

H
4.66
28.8k
61
12
85
0

After Hours Apologies

Catching his boss at work turns into unique leverage.

H
4.79
22.3k
61
13
101
0

My Roommate's Maid Pt. 02

Maid serves three masters and is assigned new tasks.

H
4.78
28.1k
61
9
78

Dress like Mia when She's Gone Pt. 01

I coped with my wife's 7 month deployment by becoming her.

4.38
44.3k
61
5
80

All Girled Out

Sabrina's wife sets her up on a date with her boss.

H
4.69
45.5k
61
25
96
0

Soul Sisters

Jan becomes a sister to his wife and her lover. (novella)

H
4.58
75.9k
61
5
74
0

The Book of Dreams

A teenage CD home alone on Halloween night... or is she?

H
4.64
62.4k
61
10
72
0

Fifi's Long Wait

Fifi the maid needs to cum so badly.

H
4.65
112.7k
61
7
89
0

Get Ahead, Give Ahead

His intern dresses like a sexy slut to get ahead in business.

H
4.55
80.6k
60
9
69
0

Prom? Ch. 02

Natalie helps Anna shop for a prom dress.

H
4.6
54.3k
60
10
73

Caught Wearing Panties

Caught but given opportunity to suck my 1st dick.

H
4.5
102.9k
60
17
81
0

Pre-Op Roommate Ch. 02

Dan & Marcie's relationship gets deeper.

H
4.66
127.4k
60
14
63

Hypnotized, Maybe?

A young man is hypnotized. Or is he?

4.45
95.1k
60
7
74
0

Britany Cums Alive

Man is turned into a BBC slut by his step daughter.

H
4.5
45.8k
59
5
98
0

Sorority Switch Pt. 01

College boy must take his sister's place in sorority rush.

4.27
56.5k
59
8
91
0

Must Be My Lucky Day

He prefers to see his daughter’s boyfriend in a dress.

H
4.51
52.8k
59
6
75
0

Caught In Lingerie Ch. 02

Sissy boy used again...and loves it!

H
4.66
63.5k
59
6
75

Mom's Nylons

He's dressed up like Mom.

4.14
250.7k
58
24
79

First Time En Femme with a Lady Top

A trans top in her thirties helps me explore sex en femme.

H
4.68
28.7k
58
10
88
0

Keeping My Sissy Secret

A young sissy fails to keep his secret from an older man.

4.43
65.8k
58
7
82
0

My BBC Neighbor

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

H
4.65
21.7k
58
6
92
0

Training My Sissy Body

Lucy finds a new man to train her as a sissy.

H
4.74
26.6k
57
6
93

Sissy BBC Cleaner Pt. 01

The beginnings of a depraved traps humiliation and ecstasy.

4.16
96.5k
57
10
76
0

Tantalising Tanya Ch. 03

Her boyfriend is out, but his father is home.

H
4.61
62.4k
57
9
64

The Making of Ana

Straight man blackmailed into becoming a sissy escort.

H
4.53
30.9k
57
9
93
0

Playing Pregnant

Sissy uses and enema to feel pregnant and girly.

4.29
111k
57
12
69
0

Theatre Sissy

Being fucked as a girl onstage wasn't the plan.

H
4.5
33.9k
57
14
82
0

How I was Trained Pt. 01

This is a story of how I was trained to be a sissy.

H
4.59
48.5k
57
20
126

Expectations be Damned

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

H
4.64
38.5k
56
7
86

A Friend Catches Me

Caught by a friend dressed in lingerie.

4.41
99.4k
56
5
75

Prom? Ch. 03

Anna, Natalie and Mike go to a bar. The tension rises.

H
4.68
43.2k
56
7
66

Halloween Hijinks

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

H
4.66
34.1k
56
9
70
0

Fine Tuning

Wife's cross-dressing game with husband opens new frontiers.

0
66.9k
56
0
73

First Time

Very close to the truth about first trans experience.

H
4.66
58.4k
56
7
69
0

Sissy College Slut Pt. 01

Alex and his black roommate gets to know each other better.

4.34
52k
56
5
124

That's What Friends Are For Ch. 02

Alex dresses up as Allison and catches the eye of an admirer.

H
4.59
129.1k
55
11
70

Payback's a Bitch

George likes sluts...but then becomes one.

4.26
97.2k
55
11
65
0

CD Stacy's First Adventure

Crossdresser Stacy embraces her sexual awakening.

H
4.72
38.2k
55
24
58
0

Just Look at Me Now Ch. 01

Nick's femdom journey begins gently, but that won't last.

H
4.51
70.7k
55
7
110

There's Something about Sarah Ch. 01

Adopted son is transformed into a sissy and lives as a girl.

4.27
61.9k
55
8
83

Brotherly Desires

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

H
4.51
69.9k
55
7
71
0

The Guy in the Leather Skirt

Hubby tricked into sissy cuckold lifestyle

H
4.73
28.3k
55
17
85
0

Easy to Imagine

He wears a dress for a customer with a good imagination.

4.37
46.3k
55
13
73
0

Leah, Locked

Two caged sissies manage to have fun together.

H
4.66
35.5k
54
5
108

The Agency Ch. 02

Mike returns to start his new job and faces new challenges.

H
4.6
42.4k
54
8
76

Wife Substitute

Forced to serve married men as a wife substitute.

3.32
215.6k
54
10
85
0

Sissy Cuckolded by Girlfriend Ch. 01

A sissy slut gets cuckolded by his girlfriend.

4.13
128.6k
54
16
94
0

This Cock Tastes Like My Wife Ch. 04

His cuckold wishes are taking shape, but not how he expected.

4.35
116.7k
54
19
66

A Geisha Used and Claimed

Feminine Asian attends a rowdy Halloween frat party.

H
4.69
27.2k
54
2
87
0

Katelyn's New Sissy Pt. 01

Learning to be a sissy and liking it.

4.48
63.9k
54
5
79
0

A Bitch is Made

Woman turns her male friend into a bitch for her boyfriend.

H
4.55
41.4k
54
5
103
0

The Sissy Models

A Daddy-Son modelling weekend and a couple of studs.

H
4.6
35.3k
54
4
74

A Beautiful Me at Honeysuckle Lake

A crossdresser opens up to his mom's best friend.

H
4.55
31.2k
53
14
71

Caught

Caught crossdressing and blackmailed into submission.

4.39
72.8k
53
6
71
0

Sissy Fantasy to Nightmare Ch. 02

The nightmare continues as John is offered an ultimatum.

H
4.76
29.9k
53
13
63

Basketball Crossdresser

His wife finds phonesex bill, makes him do it with pool guy.

H
4.55
218.5k
53
12
71
0

A Shemale Vacation Ch. 03

Tom must be Tamsyn once more to cross the border.

H
4.63
68.7k
53
14
61

First Time With A Guy

He dresses as a girl, then meets a guy

H
4.59
296.5k
53
9
81

Watching the Detectives

TG Detective tries to find out who is attacking London TGs.

H
4.84
31.2k
53
13
62
0

Brittany's First Time Out

A sissy's evening drive leads to a life changing encounter.

H
4.65
41.8k
53
5
73
0
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crossdresser
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