‘ladyboy’ stories

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ladyboy 

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Angie's Date Night

Ladyboy set up on a blind date has the time of her life.

NEWH
4.7
4.5k
10
2
19
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A Ladyboy Syndrome

Was he turned? Or wasn't he?

4.45
5.4k
3
1
8

Debauchery - Ch. 19

Jeff begins the rest of his life.

H
4.64
1.6k
3
2
5

Surprise!

A beautiful girl with a surprise!

4.41
9.6k
18
3
32
0

My Roommate Angie 01

Learning my roommate had a penis leads to more discoveries.

H
4.72
15.9k
46
10
74

Surprise Fuck with Niece's Friend

Ass fucking my niece's friend who has a little surprise!

4.15
42.7k
18
1
34

Turned into a Sissy Pt. 18

Another level added, trying gogo dancing and being tied up.

H
4.81
7k
8
2
10

The Gender Benders Reloaded

Couple discovers sexual secret at heart of the relationship.

4.43
5k
7
0
12
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Soup Style Bk. 07 - Hide or Not?

To Hide or Not to Hide, whether 'tis nobler to be unknown?

3
1.2k
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1
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Sissy Sold in Thailand Pt. 02

Eric tried an escape with his new friend.

3.94
11.3k
7
4
10

A Surprise in the Massage Parlour

A young man discovers his dark side in a massage parlour.

4.41
11.9k
10
2
24
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Kathoey

The life of a beautiful Thai woman with a difference.

H
4.67
12.2k
19
4
45
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The Awakening

My first time with a ladyboy.

3.05
9.9k
4
6
6
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My First Trans Woman

My first encounter - a beautiful Thai ladyboy.

H
4.65
20.9k
17
12
34
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Sissy Sold in Thailand

Eric leaves for vacation, but he may never return the same.

4.17
36.5k
29
8
69

Closed for Business Ch. 01

Dara realizes she's fresh out of shaving cream.

4.39
7.5k
4
0
9

The Bamboo Ceiling Ch. 12

A sissy is trained at a brothel.

3.87
15.2k
11
12
18

Turned into a Sissy Pt. 17

A weekend in Pattaya - A Sissy learns about her inner Slut.

H
4.76
9.3k
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20

Turned into a Sissy Pt. 16

A Weekend in Pattaya, Saturday - beach, gogo bar and a girl.

H
4.59
7.1k
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13

Turned into a Sissy Pt. 15

A Weekend in Pattaya - the first evening.

H
4.67
7.1k
5
4
12

Turned into a Sissy Pt. 14

A Glimpse of Everyday Sissy Life.

H
4.53
9.2k
8
3
16

From Stephen to Stevie Ch. 02

I get to see Stevie's changed body and we have a holiday.

H
4.65
6.3k
4
3
7

From Stephen to Stevie Ch. 01

A gradual transformation from boy to woman.

H
4.59
15.1k
15
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26

Tom's Journey into Submission Pt. 03

Tom finds his future. Amelia submits.

H
4.62
5k
6
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A Different Asian Threesome Pt. 01

I meet an air stewardess and her ladyboy friend.

H
4.58
16.3k
25
2
46

Derek Bradley Gets a Surprise

A young virgin discovers his sexuality & surprises his boss.

H
4.58
12.4k
15
0
29
0

Lois Has to Stay After Class Ch. 01

A senior at school, relaxed sexual adventures.

4.07
14.3k
7
1
9
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Lois and Veronica

The glamour girls visit the forest ranger.

3.75
11.5k
4
1
8
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The (not so) Wicked Witch of the East

Travelling to the exotic east, I meet a Goddess.

H
4.65
10.7k
8
3
19
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Turned into a Sissy Pt. 13

The punishment on the following day.

H
4.82
13.8k
13
6
22

Tranny Babysitter: The Conclusion

John's subjugation is complete. Is there a way out?

4.37
22.7k
13
0
31
0

Backstage with a Bangkok Ladyboy

A stage manager lives out his fantasy with one of the cast.

H
4.66
16.7k
18
1
32
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Turned into a Sissy Pt. 12

Dinner with friends and my first creampie.

H
4.55
16.3k
15
8
28

Tranny Babysitter: Force Femme

John is forced further into degradation and humiliation.

H
4.5
40.6k
19
4
50
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My New Girlfriend Pt. 03

Part 3 of 4 Our relationship develops.

H
4.88
49.2k
65
17
94

Becoming Hannah Pt. 01

October 1973, two men come together in a war torn world.

H
4.75
5.7k
3
9
10
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Turned into a Sissy Pt. 09

The birthday party continues.

H
4.59
16.8k
10
5
22

Turned into a Sissy Pt. 08

First time called a sissy and serving at a party.

H
4.54
18.8k
14
6
24

Thai Massage

Man has a suprise at the Thai massage.

4.45
71.4k
66
5
115

Turned into a Sissy Pt. 07

Shopping continues and I have my first anal orgasm.

H
4.66
31.8k
21
9
34

Like Daddy. Joy's Tale. Pt. 06

Joy and Daddy Submit to a new mistress.

H
4.76
6.8k
4
0
6

Turned into a Sissy Pt. 06

An interesting dinner and my first threesome.

H
4.62
24.8k
19
6
28

Turned into a Sissy Pt. 05

Our shopping spree continues and more.

4.49
26.6k
20
8
31

Turned into a Sissy Pt. 04

The shopping spree begins and humiliation continues.

H
4.53
27.6k
25
7
37

Turned into a Sissy Pt. 03

My journey continues with first humilation and more.

H
4.59
38.6k
31
6
46

Turned into a Sissy Pt. 02

The journey continues, now it is time for the cage.

H
4.53
49.7k
40
13
55

Turned into a Sissy Pt. 01

How my ladyboy girlfriend turned me into a Sissy.

4.4
96.9k
102
20
209

Thai Massage Surprise

Multiple surprises for a couple during a Thai massage.

H
4.51
62.1k
93
9
127
0

Cebu Hotel Sexy Threesome Pt. 02

I meet Alice, another member of the 'family'.

H
4.8
6.6k
4
6
7

Cebu Hotel Sexy Threesome

Totally unexpected but memorable evening with 2 girls!

H
4.76
16.1k
26
5
41

Filipina Fun! Pt. 03

Day 3, Sheila tries pussy, this girl is insatiable....

4.09
4.8k
1
0
1

Filipina Fun! Pt. 02

It's day two and i discover how hot she is...

4.38
9.3k
5
1
6

Filipina Pre and Post Op!

I meet Luci for the first of a series of adventures...

4.42
5.3k
6
1
8
0

Like Daddy. Joy's Tale. Pt. 04

Joy controls daddy. Kim takes a caning. Daddy tells a story.

H
4.64
5.9k
5
0
5

Bursting Ash's Bubble... Butt

Ash takes dick in the ass from nerds and spin instructor.

H
4.61
93.3k
84
15
155
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What If - Scotty the Hottie Ch. 01

Phoenix stays late with a hook-up & ends up abusing her host.

3.95
6.5k
5
0
12
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Eucalyptus Club

Exclusive sex club in the glens.

4.33
9.5k
4
2
11

Hot Ladyboy Meet

A young guy meets a hot Asian ladyboy.

4
32k
14
2
25
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Bangkok Ladyboy Voodoo Doll App!

One night of going FULL RETARD in BANGKOK!

2.13
7.6k
2
1
5
0

Makati Ch. 10

An American's adventure in Makati.

H
4.53
8.1k
3
1
4

Makati Ch. 09

An American's adventure in Makati.

4.47
7.2k
5
1
6

Makati Ch. 08

An American's adventure in Makati.

4.36
6.7k
00
1

Makati Ch. 05

An American's adventure in Makati.

H
4.61
9.5k
3
1
5

The Reunion Ch. 02: Thai Massage

Krissy relaxes with a massage with an unexpected ending.

4.17
26.1k
5
0
9

Bottom Bitch Is Bred By His Dom Top

A bottom bitch experiences joy servicing his dominant top.

4.27
48.3k
22
6
44
0

Pon and I Become One

Pon and I joined as one in pleasure.

H
4.55
18.8k
15
3
21
0

A Trans Top and Her Bottom Bitch

A cishet man finds joy in being a trans woman's bottom bitch.

4.48
56.8k
64
4
107
0

Face Down Ass Up

Leslie takes control and lets me feel all of her.

4.33
39.5k
31
5
49
0

He Said, She Said Ch. 08

A surprise guest for the evening.

4.4
6.2k
2
3
3

My First Ladyboy Experience

How a massage opened more than my mind.

4.36
52k
23
3
42
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My Thai Ladyboy

My next amazing adventure with a ladyboy.

4.47
42k
21
2
35
0

From John to Jenny

John blossoms into Jenny...against his own will...

3.95
55.7k
18
3
36
0

My First Ladyboy

Straight alpha male falls for a sexy Filipino ladyboy.

4.42
38.6k
28
7
43
0

My Transgender Love: Week 1

The first week of my vacation with my transgender girlfriend.

4.26
16.9k
12
4
17
0

Alone In Pattaya

My first visit in Pattaya.

4.47
31.1k
23
2
27
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Sissy's First Trip Out

A sissy excursion leads to an unexpected meeting.

4.28
25.7k
11
5
24
0

At the Kit-Kat Club Ch. 03

Part 3 of a 3 part story about life in the Kit-Kat club.

H
4.68
11.7k
9
3
12

A Sinful Family Ch. 01 - Moving In

A filthy rich family full of incest and intrigue.

4.12
97.8k
110
18
164

Okaikei

Coming home after a business trip.

4.13
21.1k
7
0
7
0

Lisa's Second Chance Pt. 16

It's all work hard and play hard at Dominica's place.

H
4.64
9k
7
1
11

Her First Chance at Love

What begins as an affair becomes so much more.

H
4.75
29.4k
39
6
60
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The Shemale Possession

A man possesses the body of a "woman".

0
22.7k
13
5
19
0

Cockatoo Pt. 42

Scarlett goes to meet Aki again.

H
4.84
7.9k
9
9
9

A New Adventure... Ch. 02

A little experimenting never hurt anyone.

4.15
18.9k
11
0
14

Lisa's Second Chance Pt. 13

Lisa makes a name for herself.

H
4.73
14.1k
7
2
11

Craigslist Bottom Bitch

Jake and Candy get ready and experience their next encounter.

H
4.73
67.4k
61
3
99
0
12
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Active tags
ladyboy
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