‘crossdresser’ stories

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Active tags
crossdresser 

Category

Seducing Eric

Revealing my final secret to a friend who becomes more.

4.26
51.9k
21
5
24
0

My Master & My Wife Ch. 03

Liz finds out about everything and Greg has to pay for it!

H
4.63
49.4k
36
8
40

Tantalising Tanya Ch. 03

Her boyfriend is out, but his father is home.

H
4.61
62.4k
57
9
64

New Mother, New Life Pt. 01

Crossdresser re-unites with birth mother.

H
4.6
67.5k
65
4
84

Smoking With Friends Ch. 01

Young closet crossdresser smokes with his friends as a girl.

4.17
76.9k
27
4
36
0

My Master & My Wife Ch. 02

Greg's Redezvous with His Master & His Wife's Explorations

H
4.68
46.1k
37
10
42

One of the Girls

So you want to join the girls for a night on the town?

H
4.66
132.4k
97
21
151
0

The Colonel and His Aide

The Colonel's loving transgender aide saves him.

H
4.79
28.6k
37
4
47

Ensnared by a Corset

A closeted cross dresser is discovered and humiliated.

4.12
112.1k
35
9
41
0

Lingerie Night at the Sauna

Crossdresser Night is a whole lot of fun.

4.31
47.8k
12
9
17
0

Couples Counseling Ch. 02

Dr. Kim helps Rick and Gary solve their problems.

H
4.61
31.8k
28
2
34

Husband to Wife

A story about sweet romance.

3.46
88.6k
10
4
12
0

That's What Friends Are For Ch. 03

All dressed up and finally must choose between 2 suitors

H
4.56
70k
41
8
56

Just the Three of Us Ch. 03

A couple share their love with a unique and beautiful woman.

H
4.58
25k
14
3
16

A Hard Days Shopping

Therapy fun after retail therapy.

4.29
27.7k
5
2
6
0

Just the Three of Us Ch. 02

A couple share their love with a unique and beautiful woman.

4.38
25.6k
15
2
19

A Wife Comes Around Ch. 03

A wife helps out with his fantasy.

H
4.61
110.5k
65
16
75

Spring Rain

Mistress treats him to a wet afternoon.

3.61
34.4k
7
5
10
0

Hot Potato

Girl who'd rather be a boy meets boy who'd rather be a girl

4.43
50.2k
39
15
51
0

My Dream Solution Ch. 01

How to make a gay marriage work in Arkansas.

H
4.51
22.4k
7
5
12
0

My Senior Year of College Ch. 01

A transgendered girl has her first man.

4.49
61.7k
21
7
22

A Cross Dressers First Time

A middle aged cross dresser has sex with a man.

4.39
120.8k
31
13
36
0

Long Hair & Lace Panties

A fling with his boss may be just the beginning.

4.41
48.2k
19
0
24
0

Driving Her Home

A babysitter gains the upper hand on the drive home.

3.98
74.8k
8
7
13
0

Crossdresser In Picnic Area

Crossdresser gets fucked in public picnic area.

4.47
105.1k
36
14
44
0

Parking Area 2 Miles

A rest stop to pee turns into ankles in the air.

4.29
64.1k
14
7
16
0

Dress Me and Use Me

When my wife's ex returns to town, my fantasies start.

H
4.5
100.5k
92
16
124
0

Laurie's Nightclub Adventure

Laurie gets more than he/she expected at a nightclub.

4.33
39.3k
13
4
17
0

Silver Cloud

A Rolls-Royce, a broken date, and a guy dressed as a girl.

H
4.56
30.6k
30
3
37
0

Mikey and Bobby Ch. 02

Mikey wants to have some of the fun too.

4.33
26.2k
14
1
14

My Second Time

Crossdresser's second time fucked by another man.

3.82
85.3k
11
11
13
0

A Great Day Off Work

Another Craigslist hookup on a day off from work.

3.97
36.8k
8
2
10
0

Friends, Roommates, and Lovers

Jamie meets his dream girl, only to find out it was him.

H
4.62
75.7k
99
21
125
0

Being a Sissy for Viv Ch. 03

Waking up in a satin nightie.

H
4.54
91.5k
43
10
54

My First Time CD Sex

My very first time getting sex from a man.

4.04
170.4k
16
22
22
0

Candy Gets Found Out

TV's first sexual experience goes wrong and then right!

4.22
37.3k
7
3
9
0

Brotherly Desires

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

H
4.51
69.9k
56
7
72
0

Their Drinking Leads to My Pleasure

Riding the cock of passed out cousin.

3.72
69k
18
2
29
0

Lady In The House - Reprised Ch. 18

Transvestite prison prostitute Michele continues her saga.

H
4.66
38.1k
18
2
20

The Mother I Never Knew Ch. 02

Family and friends with benefits comes together.

H
4.69
135.8k
156
22
193

Not That Kind of Girl

She's not the kind of girl he was expecting.

4.22
73.5k
41
19
61
0

A New Life

A young man leaves home because he wants to be a girl.

4.49
63.4k
23
14
27
0

Seducing Jay at a House Party

My gay encounter with a crossdresser.

4.3
47.3k
21
5
23
0

Payback's a Bitch

George likes sluts...but then becomes one.

4.26
97.3k
55
11
65
0

Chantal Nights

My first time with a transvestite.

H
4.57
54.6k
47
9
54
0

A New Life

Crossdresser wearing hijab and abaya finds a lover.

4.34
37.7k
13
6
20
0

A Summer Camp Adventure

A 19 your old male goes to cheerleader camp.

4.47
123k
80
10
101

Tantalising Tanya Ch. 01

Fun with her boyfriend's brother.

H
4.59
99.4k
77
7
104

Rayne Falls Ch. 02

Overcast: A night on the town.

3.29
6.2k
000

2053: Submission

In the future a young man submits to a gang leader for work.

3.98
44.7k
33
0
38
0

Track and Field Encounter

18-year-old t-girl meets her ideal man at the track meet.

4.41
44k
52
1
65
0

You Got the Part!

Actor gets the role of a lifetime.

4.22
72.3k
28
8
37

Need More Therapy

Follow up to Therapy Helps (Jasmine & Ava).

4.44
27.8k
7
4
8
0

Jeff Crossdresses More & More

Jeff is encouraged to dress more in the run-up to Halloween

H
4.58
144.9k
93
16
121
0

A Rough Afternoon

A closet crossdresser treated rough.

4.19
66.5k
39
4
46
0

While You Were Away Ch. 03

Left to settle into the new role while Sam's out...

4.2
23k
6
1
7

Dancing on My Cocks Tunes 01

Realizing my true self, becoming a woman.

3.85
52.4k
8
1
12
0

Kelly Ch. 02

Jim and Kelly consecrate their newfound relationship.

H
4.53
36.1k
27
9
28

Panty Fantasy-Hurricane Kate Ch. 03

A little glimpse into Lin's point of view.

4.14
37k
6
11
6

Fat Indian Crossdresser Slut Gangbang

A hot story of a sissy and fat crossdresser getting gangbang.

3.98
60.9k
14
5
21
0

Hotel Heaven or Nightmare

Crossdresser's cosy evening is brought abruptly to a halt.

4.17
33.4k
10
4
11
0

A Confession of Mine

Letting out a secret part of myself.

3.79
11.2k
1
2
1
0

Meet Miss Brown

A young woman discovers a man's feminine side.

H
4.66
55.5k
19
13
24
0

Being a Sissy for Viv Ch. 01

Pretty panties is all it takes.

4.49
221.9k
166
33
233

The Landlord

College student gets more than he bargained for with room.

H
4.62
109.7k
71
7
94
0

Cross-Dresser Fucked by Hot Sissy

Anal and oral fun between to hot sissy cross-dressing sluts.

4.25
127.8k
40
17
48
0

Story of Heather Ch. 01

How I became Heather throughout the years.

4.23
47.5k
14
7
18
0

Changing Room Prank Ch. 02

Alice can't stop thinking about the night before.

H
4.53
94.1k
100
14
115

Wife Substitute

Forced to serve married men as a wife substitute.

3.32
215.8k
54
10
85
0

Young Chrissy Dresses and Sucks

I dress as a girl and meet a guy from Craigslist.

4.19
100.3k
18
12
25
0

Just a Game Ch. 01

A "harmless" game changes Stan's life forever.

4.31
81.3k
37
7
40
0

A Christmas (Bondage) Story

Santa's Elf leaves a gift for his Mistress.

4.33
60.9k
14
9
19
0

Her Surprise

You meet a cute punk in a magic sex toy shop, then surprises.

3.41
32.1k
6
1
11
0

Feminine Enough Ch. 03

Dustin comes home unexpectedly.

H
4.6
50.6k
18
7
18

The Awakening Ch. 04

Michele's memory returns and she wants to fuck!

4.41
29.1k
8
3
9

A Missy Affair

Closest crossdresser discovered and used.

4.33
153.8k
49
11
65

Allyson the Sissy Whore Ch. 01

'Allyson' lives out her sucking fantasy.

4.06
93.9k
33
8
44

From Heels Fetish to Cock-Sucking

A crossdresser's meeting with online chat buddy.

4.11
82.4k
27
10
37
0

Mommy I Feel Like A Girl Ch. 09

Sunbathing when Dan shows up unexpectedly.

H
4.65
52.4k
25
2
28

That's What Friends Are For Ch. 02

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

H
4.59
129.3k
55
11
70

Robin and Mia

Rob is forced to become Robin.

4.45
103.4k
50
12
64
0

That's What Friends Are For Ch. 01

Alex is teased into putting on panties for David.

H
4.53
206.8k
117
17
173

A Bet is Maid

I lose a bet that ends me up on the other side.

H
4.51
200.4k
129
8
154
0

The First Meeting

Laura and David meet for the first time.

H
4.56
34.8k
6
5
6
0

Fringe Benefits

Airport custodian bangs faggot asses.

4.28
65.3k
38
4
49

The Delivery

Christina enjoys internet shopping in particular.

H
4.51
28.6k
8
3
8
0

Cheaters

Black man cheats on tranny girlfried with a pussyboi.

4.36
56.7k
50
2
56
0

The Emergence of Sarah Ch. 02

Continuation of the night that would change his/her life.

H
4.69
23k
9
9
9

Brought to Heel Ch. 02

Chloe discovers that someone was watching her.

H
4.67
26.6k
6
2
6

Brought to Heel

Chloe shops for shoes and gets more than she expected.

H
4.61
77.3k
28
7
30
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crossdresser
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