‘transvestite’ stories

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Active tags
transvestite 

Category

The Babysitter

Babysitter guy becomes babysitter girl.

H
4.62
861.8k
914
63
1.2k
0

Dad's Dirty Boy

Sparks fly when father sees his college son in lingerie.

H
4.53
781.6k
712
52
882
0

My Initiation

One man's introduction to a new life.

HW
4.74
724k
204
132
255
0

My Wife Erica And Our Friend Jack

He's feminized by his wife and her boyfriend.

H
4.58
482.8k
207
21
313
0

One Week Ch. 01 Second Edition

Updated verison of One Week.

HW
4.74
457.4k
222
37
265

Paying Mommy’s Mortgage

Mom has to use son as mortgage payment.

4.15
443.6k
159
12
235
0

A Deal with Daddy

Gay incest! Dad lets son fuck mom, for a price.

3.84
434.4k
193
22
262
0

Hypnotized by Chelsea

He is hypnotized to think he's a girl.

4.11
383.7k
64
18
108
0

Michele and Buster: A Tranny Tale

Tranny Michele meets Buster for sexy fun.

4.06
381.5k
15
7
16
0

Mandingo Row

Man follows wife to see where all the white women go nightly.

3.02
381k
31
15
43

A Flash of Lace

His dark secret is discovered by his beautiful sister.

H
4.73
380k
196
57
244
0

Chastity with Ex as Keyholder

Ex discovers secret chastity fetish while dating new BF!

4.49
370.7k
322
21
476

Stepmom's Sex Shocker

Son dresses in stepmom's lingerie.

4.29
360.4k
123
4
182

A Sister's Revenge Ch. 01

Michael's decent into womanhood begins with a peek.

4.44
344.8k
159
24
224

Cum Sucker

Step-sister forces brother into sexual slavery.

4.25
332.6k
82
11
136
0

My Father-In-Law's New Bride Ch. 02

Father-in-law continues son-in-law's bridal training.

4.46
303.6k
87
9
95

So You Wanna Be A Pornstar

Grad School hipster is forced to play female porn lead.

4.25
298.4k
86
11
140
0

Epiphany

Young man experiences the ultimate feminine act.

H
4.58
293.5k
94
30
109
0

Jen turns Dad into a Sissy-slut

Daughter dresses her dad up & takes his anal cherry.

4.41
283.5k
118
22
166
0

Sister is My First

He's caught in sis's lingerie.

0
273.6k
103
27
128
0

Man Is Humiliated By Escort

Humiliated by escort, her clients and wife.

4
272.7k
71
12
91
0

My Strapon Fantasy

A girl helps her boyfriend live out his fantasy.

H
4.5
270.9k
143
24
205
0

Forced Entry

Transvestite caught in her hotel room is forced into sex.

H
4.52
255.4k
103
14
133
0

Mom's Nylons

He's dressed up like Mom.

4.14
249.8k
58
24
80

Popping Lisa's Cherry

Lisa goes all the way as a lady.

H
4.58
237.6k
32
14
35
0

First Time Being a Woman

Crossdresser experiences being a woman.

4.29
236.9k
40
19
54
0

Cross-dresser Drinks Cum

A cross-dresser and his girlfriend reveal secrets.

4.49
235.6k
72
23
95
0

Sexual Harassment Ch. 02

Alex's girlfriend continues his humiliation.

4.46
235k
46
15
62

Basement Treasures

Cleaning out dad's basement leads to family secrets.

4.3
234.8k
37
6
56
0

Cockwhore's Total Gangbang

Cross-dressing young man is gang-banged by 20 men.

H
4.51
234.4k
154
24
174
0

His Sissy Bitch Ch. 04

A man's sissy girl is to become his very public little bitch.

H
4.56
233.8k
104
11
110

A Wicked Halloween

Mom dresses up her son and friend.

4.13
232.6k
108
0
160
0

Been Caught Cheating

His girlfriend forces him to be fem.

4.21
232.1k
80
10
104

In My Place

Crossdresser is forced to go a lot further than he intended.

4.4
231k
76
16
93

Chastised, Feminized, Sodomized

submissive Asian man and a Dominant woman.

4.49
229.7k
172
46
238
0

Discovered by a Black Guy

Black guy with huge dick uses me as his chastity slut.

H
4.57
229.4k
267
27
347
0

Crossdressing Brother

Sister catches her brother dressed in her underwear.

4.41
226.5k
74
3
92

Devil in The Red Dress

Hung and well endowed Hermaphrodite lures a bedmate.

4.44
218.4k
126
12
145
0

Florida Vacation

Staying in a dive motel can be hazardous to one's ass.

4.37
213.6k
47
13
70
0

Randi Michelle's Sissy Subjugation

One sissy's fantasy of how she will be transformed.

3.99
209.6k
24
8
36
0

Cum Drinker

Sister fucks cross-dressing brother.

4.27
204k
48
0
76
0

A Sister's Revenge Ch. 02

Michael enjoys (?) many first-time experiences.

4.45
202.7k
53
9
62

Brotherly Love, Sisterly Love Ch. 02

The crossdressing twins enjoy a costume party.

H
4.68
201.7k
107
17
116

Taste of My Girlfriend's Dildo Ch. 02

Caught again - and made to crave it.

H
4.56
200.5k
82
10
93

Pool Boy Gets Dressed Up Ch. 02

Pool Boy turned Tranny by his mistress.

H
4.67
199.4k
106
18
137

My Father-In-Law's New Bride Ch. 04

Wife helps daddy with bride's new training.

4.44
196.8k
74
14
81

Groomed to Depravity Ch. 01

A college boy's life goes awry on Halloween.

4.41
196.3k
288
12
466

Crossdresser Fantasy Come True

Closet crossdresser finally has first experience with a hunk.

4.47
191.3k
43
24
47
0

Sissy Crissi Ch. 01

Chris Taylor takes his cross-dressing to the next level.

H
4.58
191.1k
88
23
112

New 'Girl' in the Office Ch. 01

Feminine guy becomes the boss's new PA.

4.23
190.2k
39
6
49

How I Became a CD SLUT Cum Junky

True to fact embelished origin of my CD life and cum craving.

H
4.67
183k
142
16
172

TV Blowjob Slut for Blacks

He goes to the wrong bar and forgets his wallet.

H
4.56
182.4k
139
21
158

Her New Girlfriend Ch. 02

Transition: the morning after.

4.47
180.1k
48
5
54

The Truth is Known

Wife discovers her transvestite hubby likes cocks.

4.06
179.6k
24
2
30
0

Just a Girl

Sissy-boy Frank & his girl both become David's girls.

3.97
177.7k
52
19
80
0

My New Sister

Cindy's shocking discovery about her twin.

4.1
174.6k
40
6
58

Lonely Man Becomes a Sissy

He becomes a sissy for an online mistress.

4.34
173k
59
7
79

The Part-Time Job

Young man gets more than he bargained for.

H
4.58
171.9k
120
20
159
0

Hot Wife at the Bar

My hot wife and I go to the bar where everything goes.

4.38
163.6k
65
6
96
0

Daddy's Transvestite Toilet Slave Ch. 01

Cross-dressing Son becomes his Father's Sissy Boy.

4.07
163.3k
85
11
110
0

Anastasia's Life

A crossdresser's awakening.

H
4.62
162.7k
35
5
48

TV Blowjob Slut for Blacks Ch. 02

Hubby becomes a blackman's steady blowjob slut.

H
4.58
156.3k
61
14
72

My First Black Cocks

Crossdresser goes out to find big dark meat.

4.29
155.9k
44
22
47
0

Our Steven, Our Stephanie Ch. 02

Diane chastises Steven for his silly notions.

4.27
154.8k
27
8
37

A Missy Affair

Closest crossdresser discovered and used.

4.33
153.5k
49
11
64

Chastity with Ex as Keyholder Ch. 02

Ex continues humiliating me with chastity.

4.3
153.5k
64
9
90

Daddy's Little Helper

Son discovers a secret about his father.

4.4
152.7k
63
20
73

Lonely Man Becomes a Sissy Ch. 02

Sissy wakes up to a new world with Mistress.

4.28
152.4k
33
11
40

Girl's Night Out

Showing a friend the joys of public femininity.

H
4.66
151.1k
63
20
83
0

New 'Girl' in the Office Ch. 02

Secrets are revealed, in a very horny way.

H
4.52
148.5k
26
15
30

Hotel Girl

Satisfying the customer.

H
4.54
147.2k
34
13
41
0

The Adventures of Lexi Ch. 01

Getting caught leads to the night of his life.

H
4.7
143.9k
141
11
184

A Sister's Revenge Ch. 04

Michael's new home, Michael's new name, Michael's new life.

H
4.64
138.3k
60
27
65

Poker Night Servant

Gen serves the men, on her knees!

4.11
138k
20
11
21
0

Magic Panties Ch. 02

Roy has sex, then realizes somethings up with the panties.

H
4.52
137.6k
42
4
49

Roommate

A grad student gets the best roommate of his life--and more.

4.4
137.2k
71
19
93
0

Lucy's Revenge Ch. 02

The Park Ranger continues Cynthia's humiliation.

H
4.63
137.1k
52
1
61

Working Hard for Her Job

A secretary learns what her boss expects of her.

4.48
136.9k
70
10
96

A Night Out To Remember

A change of clothes leads to a new life.

H
4.53
135.9k
46
6
61

Birthday Present Pt. 02

He becomes his wife's lovely lesbian lover.

H
4.71
134.8k
48
15
59

A Very Hard Working Girl

Sexy slut does what she does best, services men.

H
4.56
133k
67
5
79
0

Daddy Complex Ch. 01: Giving It Up

A strange request leads to one unforgettable night.

H
4.56
131.7k
155
17
252
0

Alexis

Young crossdresser begins the transformation to a slut.

4.43
130.1k
51
6
57

A Wife Comes Around

How a wife came around to her husband's pleasures.

4.45
129k
83
3
100

A Night to Remember

My first cock while dressed as a woman.

H
4.52
128.2k
42
18
51
0

Stockings and Heels in Public

Newbie CD tries out stockings & more in adult theater.

4.33
127.8k
42
18
52
0

The Bitch Bites Back

Attacker Mike is transformed into crossdressed whore Michele.

4.45
127.8k
46
9
59
0

More

Some games are more compelling than others.

4.42
127.7k
51
0
72
0

Walker Family Incest Ch. 04

Our family spends the day at the nude beach.

4.38
126.6k
41
2
59

Worshipping Wally's Prick

Learning to be a submissive cock lover.

4.37
126.4k
39
11
61
0

Remember / Forget

You wake up from a hypnotic trance bound & blindfolded.

3.89
125.5k
21
11
46
0

In My Place Ch. 02

His domination continues. What are his wife's plans for him?

4.39
125.3k
14
6
20

How I Became a CD SLUT Cum Junky Ch. 02

A Halloween party before the gang bang and I get too wild!

H
4.77
124.4k
85
12
91

Our Steven, Our Stephanie Ch. 04

Steven helps Diane with her school project.

4.39
123.9k
27
3
30
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Active tags
transvestite
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