‘transvestite’ stories

Active tags
Active tags
transvestite 

Category

Femboy Hooters

A restaurant with an all-trans wait staff in sexy outfits.

H
4.8
19.5k
49
6
81
0

Christine Cuckolds Joel Pt. 02

Christine explains new rules and deviously tightens control.

3.77
4.7k
1
1
2

Christine Cuckolds Joel Pt. 01

Christine Cuckolds her Husband using Paul & Red Lipstick.

2.58
7.4k
3
2
8

The Feminine Psychology of Sissies

The Homosexual Psychology of Femme Sissies.

0
3.1k
5
5
10
0

My Therapists Solution

My therapist helps me find what I really wanted.

H
4.63
12.2k
19
0
40
0

When Annie made Me Lucy Pt. 10

Lucy's first day at work, a plug and a tied up fucking.

H
4.68
2k
5
2
8

Help Wanted

Working as a window model at an Adult Store.

H
4.69
8.5k
25
11
45
0

When Annie made Me Lucy Pt. 09

Annie's strapon feels real when Lucy sucks and is fucked.

H
4.81
3.7k
3
1
9

When Annie made Me Lucy Pt. 08

Lucy fucks Annie at a public event, licks her clean after.

H
4.79
2.6k
5
2
9

The Intimate Dinner Party

An intimate dinner party turns erotic.

H
4.53
13.9k
31
4
54
0

When Annie made Me Lucy Pt. 07

Relaxing and shopping as Lucy, preparing for a first date.

H
4.58
2.7k
5
5
7

When Annie made Me Lucy Pt. 06

Playing with our shemale maid and making her cum.

H
4.81
3.7k
5
1
9

The Rise of Rachel Price T-Girl Pt. 40

Levant gets Rachel back with the perfect gift.

H
4.71
2.5k
6
12
8

The Rise of Rachel Price T-Girl Pt. 39

Post op Rachel adjusts to her new reality and makes a bet.

H
4.65
2.4k
6
9
7

The Rise of Rachel Price T-Girl Pt. 38

Recovering Levant completes Rachel's metamorphosis.

H
4.67
2.9k
4
16
5

Hung Alessia's MILF Adventure

Alessia meets Mature MILF Canadian for sun & sex in Greece.

H
4.68
7.7k
14
4
21

The Rise of Rachel Price T-Girl Pt. 36

Levant's medical problem becomes Rachel's emotional one.

H
4.79
2.3k
8
7
9

The Rise of Rachel Price T-Girl Pt. 35

Rachel discovers the truth and lets Levant nails her ass.

H
4.77
3.4k
6
11
8

Sindy’s Skinema

Sindy finds herself in her own erotic cinema story.

4.38
3.6k
3
1
8
0

Game, Set and Match

Alessia plays with her tennis coach!

H
4.57
4.3k
3
1
7
0

The Rise of Rachel Price T-Girl Pt. 31

Rachel encounters her grandfather as her self for first time.

H
4.67
3.2k
9
12
11

The Rise of Rachel Price T-Girl Pt. 30

Levant goes public on Governor.Lesbian Samantha frigs Rachel.

H
4.82
2.7k
8
5
9

The Rise of Rachel Price T-Girl Pt. 29

Rachel hopes Levant's mother will save her from him.

H
4.77
3.1k
8
10
9

How I Became a Sissy Ch. 01

The story about how I became a sissy.

4.49
37.3k
35
13
62
0

The Rise of Rachel Price T-Girl Pt. 28

Rachel surrenders and receives more from Levant in England.

H
4.72
2.9k
8
7
9

The European Way Pt. 02

Hans and I tour Europe tasting so many men.

H
4.52
4.4k
14
4
20

The Rise of Rachel Price T-Girl Pt. 25

Rachel negotiates a new stricter contract with Levant.

H
4.77
3.2k
9
7
11

The Rise of Rachel Price T-Girl Pt. 24

In Venice, Rachel is seduced by the city and the body guard.

H
4.75
2.9k
11
14
13

First Contact

First time experiencing going female.

4.47
11.3k
11
8
14
0

The Rise of Rachel Price T-Girl Pt. 20

Rachel forced to have her first breast implants in Paris.

H
4.76
5.9k
10
15
15

The Rise of Rachel Price T-Girl Pt. 19

Rachel must pass as female when attending high class ball.

H
4.77
4.6k
8
12
11

The Rise of Rachel Price T-Girl Pt. 18

Rachel starts her HRT while exploring his new super mansion.

H
4.74
4.2k
11
12
12

The Rise of Rachel Price T-Girl Pt. 17

Denver signs a contract to be Rachel full time for a year.

H
4.76
3.9k
10
15
12

The Rise of Rachel Price T-Girl Pt. 16

Rachel breaks up with Levant to be Denver,quickly regrets it.

H
4.72
3.1k
9
8
10

The Rise of Rachel Price T-Girl Pt. 15

Charlie's gay conversion therapy of Denver->Rachel climaxes.

H
4.73
3.8k
9
10
10

The Rise of Rachel Price T-Girl Pt. 14

Denver flys to Vegas and is Rachel for the entire weekend.

H
4.85
3.9k
10
7
12

The Rise of Rachel Price T-Girl Pt. 13

Denver lured to clubs as Rachel, meets dressmaker Samantha.

H
4.75
3.4k
10
7
12

Filling Station Surprise

Surprise hookup for attendant at gas station brothel

4.43
7.8k
5
0
15
0

Fan Male Ch. 04

Chapter Four: In and Out of the Grasp.

H
4.75
1.9k
00
1

Fan Male Ch. 03

Chapter Three: Closing in but not fast enough.

H
4.68
1.7k
1
0
6

Fan Male Ch. 02

Chapter Two: Monkey See . . .

H
4.55
2.1k
3
0
4

Fan Male Ch. 01

D.C. vice cop Hardesty hunts Net writer stalker.

H
4.65
3.1k
5
3
16

A New Life, A new Girl Ch. 01

A guy with bad dating and hookup experience meets a new girl.

H
4.68
18.8k
39
6
80

The Client

A young man gets to live out his mohair fetish fantasies.

H
4.84
3k
1
3
2
0

Arctic Heat Ch. 03

The crossdressing husband sucks both the escorts cocks.

H
4.69
6.8k
3
0
6

Almost Damsel Almost in Distress Ch. 06

Tgirl parties after the club and then works the streets.

H
4.73
5.1k
15
3
19

Neighbor's Secret

Daniel finds out about his neighbors secret.

4.18
15.3k
14
8
24

Kelly and Alessia's First Encounter

Kelly recounts her first meeting with TV model Alessia.

H
4.73
2.9k
5
1
5
0

Fantasies of a Bisexual Shy Couple #18

On this fantasy we are introduced to BDSM by her boss.

3.92
4.5k
4
2
4

Fantasies of a Bisexual Shy Couple #17

On this fantasy we play with her boss, our lover and shemale.

4.15
4.5k
5
0
6

Jitter 01

Jitter's neighbor has a train wreck going on.

3
2.4k
0000

Alessia and I Shock Our Guest!

Surprise guest gets more entertainment she she bargained for.

H
4.59
5.9k
7
2
13
0

Doppelgänger

An exact double, crossdressing fantasy, and a sexy prank.

H
4.56
6.5k
7
2
13
0

Fantasies of a Bisexual Shy Couple #09

On this fantasy we met our BBC lover and transvestite.

4
3.3k
3
1
4

Andrew Becomes Andrea for the Night

Andy becomes a tranny for the evening ending in a threesome.

H
4.57
8.1k
10
3
19
0

The Baller Pt. 02

Ex Football Player, Sissy Submission. TILF soccer mom.

4.48
3.6k
1
0
3

Corrupting The Underwear Thief Pt. 01

I catch the young lad next door stealing my underwear.

H
4.72
19.3k
33
15
54
0

Total Submission

Str8 girl turn lesbian and bf converted to sissy slut.

4.28
22.1k
17
13
25
0

The Baller Pt. 01

Ex Football Player, Sissy Submission.

4.27
5.3k
4
0
8

Bi Bitch

The tale of a morning of pure filthy debauchery.

H
4.51
11k
6
3
20
0

A Latex Crossdresser's Dream Pt. 09.5

The continued exploits of a latex crossdresser.

H
4.81
5.5k
10
2
17

Camera Shy

Crossdresser seduces reluctant cameraman.

4.35
8.1k
5
2
10
0

Almost Damsel Almost in Distress Ch. 05

Tgirl continues her adventures as a ponygirl and at the club.

H
4.85
7.3k
10
2
14

Margot's Contract Ch. 02

Spanked and put in chastity and bloomers.

H
4.67
24k
19
8
32

Love Story between Two Old Men

I became my best friend's woman helping overcome depression.

H
4.67
8.1k
3
4
7
0

Emma's Stiletto Seduction Pt. 12

Trans Emma is shared with an older mechanic.

H
4.69
4.5k
1
1
4

Emma's Stiletto Seduction Pt. 11

David introduces trans Emma to an old work colleague.

H
4.68
3.1k
2
0
7

Duncan’s Gift Pt. 02

Duncan's power of suggestion helps Gary.

3.73
10.4k
4
0
8

Camming Down the Rabbit Hole Ch. 12

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

H
4.89
37.6k
64
76
75

First Experience

Weekend in KC with my Girlfriend.

4.08
9k
3
3
5
0

Camming Down the Rabbit Hole Ch. 11

A decision needs to be made for our cam gurl.

H
4.9
33.5k
48
26
57

Laci & Johnathon's Story Ch. 02

A continuation of a budding sexual relationship.

4.45
2.3k
000

Laci & Johnathon's Story Ch. 01

Laci and Johnathon wind up with a Sunday Night fling.

4.19
16.6k
6
1
10

Big Black Transvestite Mistress Ch. 02

Back again to serve my mistress...and her friend!

H
4.76
16.3k
37
3
60

Tricked by a Tranny

Tricked and bribed by a tranny in the middle of nowhere.

H
4.64
44.2k
73
10
124
0

Big Black Transvestite Mistress

Submission to a Big Black Transvestite Mistress.

H
4.74
35k
81
12
125

The Education of Tami

Meeting with Mistress does not go as planned.

4.26
5.9k
3
0
4
0

Tami's Descent Pt. 01

Night of Picture Taking Goes Awry.

H
4.64
8.7k
12
0
19

Emma's Stiletto Seduction Pt. 08

Tranny Emma gets wet, messy and more from David.

H
4.56
4.5k
3
0
5

Emma's Stiletto Seduction Pt. 07

David is woken with a blowjob from trans Emma.

H
4.75
4.3k
4
2
8

Wilma Ann & Friends - The Audition

A shy CD comes out of the closet with an experienced tranny.

H
4.61
8.7k
12
4
15
0

Emma's Stiletto Seduction Pt. 06

Emma finally gets her just desserts from David.

H
4.53
4.1k
2
1
3

Lady's Bottom – 01: An introduction

Life in an English village where women are in charge.

4.18
12k
9
4
16
0

Sissy Maid to Mom and Sister Pt. 03

Liz bonds with her mom before her sissy maid brother returns.

H
4.67
32.1k
38
6
71

Sissy Maid to Mom and Sister Pt. 01

Andy gets caught by his sister in her panties and it's fine.

H
4.58
55.4k
81
12
184

Rick Mallet Ch. 05-06

He "interrogates" a transvestite.

4.36
1.9k
1
0
3

Camming Down the Rabbit Hole Ch. 08

Going deeper into the warren has never been so much fun.

H
4.84
19.3k
43
13
54

Brian or Brianna? Pt. 01

Crossdresser gets caught and has to make a .

4.36
22.1k
11
5
19
0
Active tags
Active tags
transvestite
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