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‘ladyboy’ stories

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Family Friendly Ch. 04

The weekend with aunt Chiharu continues.

by bleepblorper in Incest/Taboo 03/14/2018
H
4.67
19.1k
19
0
31

Family Friendly Ch. 03

An aunt with a special gift comes to visit.

by bleepblorper in Incest/Taboo 03/09/2018
H
4.62
27k
23
0
29

Craigslist Encounters Ch. 01: Craigslist Cumslut

Jake searches Craigslist and finds a ladyboy Mistress.

by xploring96 in Transgender & Crossdressers 01/20/2018
H
4.69
73.6k
102
11
149
0

Shemale Orgy

Ladyboy Mistress shares submissive with other shemale Doms.

by xploring96 in Transgender & Crossdressers 11/05/2017
H
4.59
108.4k
169
6
244
0

Lisa's Second Chance Pt. 08

Lisa has a busy two days.

by Lisa_Sweety in NonHuman 10/25/2017
H
4.62
22.9k
8
1
12

Lisa's Second Chance Pt. 06

Lisa helps out a newbie with a little secret.

by Lisa_Sweety in NonHuman 10/16/2017
4.48
20.3k
8
0
10

Cockatoo Pt. 37

Shane and Nin get together. Jamie gets ready for the party.

by nikkiesilk in Transgender & Crossdressers 09/23/2017
H
4.76
8.7k
8
2
8

Cockatoo Pt. 36

James gets ready to go to Kritsada's party as Jamie.

by nikkiesilk in Transgender & Crossdressers 09/14/2017
H
4.82
10.7k
7
4
7

Meat

A man takes home the waitress from his favorite steak house.

by xploring96 in Transgender & Crossdressers 08/31/2017
H
4.59
126.2k
162
12
217
0

Agnes Dourville Ch. 12

Anton and Antonia.

by ValoryG in Transgender & Crossdressers 07/01/2017
4.48
11.5k
4
6
7

I have a Confession to Make

After a fight with the wife, a man helps a college girl/boy.

by malid in Transgender & Crossdressers 06/09/2017
H
4.55
48.6k
57
6
68
0

The Training of a Ladyboy

Best friend makes me his personal Ladyboy.

by dreamweaver5539 in Gay Male 05/16/2017
H
4.57
65.4k
104
10
141
0

A Prisoner to the Middle Sex

One man in Bangkok, and his ladyboy prisoners.

by way2law in NonConsent/Reluctance 02/26/2017
4.37
59.1k
49
5
64
0

Addicted to Pream's Cream

A man's first TS encounter at a massage parlor.

by Vodka_Jim in Transgender & Crossdressers 01/27/2017
H
4.65
108.8k
183
20
237

The Misadventures of Amelia Pt. 02

Amelia goes to work with her new friend!

by astralprojection in Transgender & Crossdressers 10/02/2016
H
4.54
15.3k
8
2
10

My Treasure

My first time encounter with a ladyboy.

by Tetris07828 in Transgender & Crossdressers 05/14/2016
H
4.66
111.5k
74
4
89
0

Letter from Ravenswood Bluff

Mistress Jessamyn tells all.

by justincbenedict in BDSM 01/09/2016
4.2
9.8k
2
0
6
0

Letter from Dayton

From a Young Male Master of Naughty Boys!

by justincbenedict in BDSM 01/01/2016
3.45
13.7k
4
0
5
0

Cockatoo Pt. 17

James returns from Bangkok with news for Alex and Areeya.

by nikkiesilk in Transgender & Crossdressers 11/28/2015
H
4.76
17.2k
7
5
7

Futagear

A futa story.

by JSBloodwine in Sci-Fi & Fantasy 08/18/2015
4.48
66k
103
10
136

Cummy Panties

Erotic encounter at a bar.

by planplan in Transgender & Crossdressers 08/15/2015
4.38
64.6k
46
14
52
0

My First Thai Holliday

Young man gets fucked by horny shemales.

by happytraveler81 in Transgender & Crossdressers 08/08/2015
H
4.5
174.2k
173
6
218
0

Cockatoo Pt. 05

Naive Englishman gets more involved with old friend.

by nikkiesilk in Transgender & Crossdressers 04/10/2015
H
4.73
28.1k
15
8
19

Quinn

A young cross dresser transforms.

by 36FF_Tiki in Transgender & Crossdressers 04/09/2015
4.41
51.6k
52
6
65

That Helpless Moment

Story on how I found myself helpless against two Asian ladyboys.

by clex2313 in Transgender & Crossdressers 03/13/2015
4.47
76.1k
57
10
73
0

My Cleaner Ch. 03

Married man and ladyboy.

by gendidi in Transgender & Crossdressers 01/22/2015
4.18
36.9k
11
2
16

Wild Asian Adventure Ch. 05

Final chapter of a wild trip gets wilder.

by SubBiLover in Group Sex 01/20/2015
H
4.69
19.3k
11
0
15

Banker's First Encounter

Banker seduced by ladyboy customer.

by gendidi in Transgender & Crossdressers 01/19/2015
3.79
46.9k
14
2
16
0

My Sexy Changes Ch. 04.2

Make embraces his feminine side.

by TaraJaden in Transgender & Crossdressers 11/04/2014
4.03
42.4k
10
1
10

My Sexy Changes Ch. 04

Male discovers his female-self.

by TaraJaden in Transgender & Crossdressers 10/23/2014
4.26
49.4k
12
5
14

Catching Up with Susan

Lady-boy Susan confesses her top fantasy.

by aussie_101 in Transgender & Crossdressers 10/21/2014
H
4.68
50.3k
45
3
61
0

T-girl's Double Date

She used to be a boy but she's all woman now.

by SweetPrettyAss in Transgender & Crossdressers 08/15/2014
4.38
55.2k
33
1
41
0

My Cleaner Ch. 02

Married man seduced by ladyboy.

by gendidi in Transgender & Crossdressers 08/14/2014
4.05
47.8k
16
0
20

My Cleaner

Married man seduced by ladyboy.

by gendidi in Transgender & Crossdressers 07/07/2014
3.98
82.9k
32
4
42

Ts Tasha Jones Takes Huge Cock

An encounter when I was a stripper.

by tstashajones in Transgender & Crossdressers 04/12/2014
4.01
80.1k
33
4
46
0

Hero's Welcome

A soldier comes home to meet a new friend.

by CrimsonClown in Gay Male 12/12/2013
4.1
35.3k
17
0
26
0

My First Ladyboy

Looking for something new I meet with a my first ladyboy.

by 69plus1 in Transgender & Crossdressers 10/04/2013
H
4.6
118.9k
59
8
82

Ladyboy Maid

A seductive ladyboy changes a married man's life.

by HarlanPilate in Transgender & Crossdressers 09/24/2013
H
4.54
279.9k
300
29
362
0

Lin

A trip to Thailand for some forbidden fun.

by goldbloke in Fetish 07/24/2013
4.37
49.2k
21
0
29
0

The Club

They thought they were just going to watch...

by SweeetLee in Transgender & Crossdressers 07/15/2013
4.39
54.4k
36
4
48
0

In The Moment, Things Change

Who cares what she's working with - bring it on!

by mikeinto in Transgender & Crossdressers 07/01/2013
4.39
44.3k
25
6
29
0

The Vicar's Wife Ch. 25

A new outfit for Sarah.

by sarahloveitt in Group Sex 06/30/2013
H
4.65
28.9k
9
4
10

Girls Vegas-Style

Lonely man in Vegas hooks up with a fine looking "lady".

by snerpyloo in Transgender & Crossdressers 06/10/2013
4.31
87.8k
31
8
42
0

A Night to Remember

That unforgettable night, when he first met her...

by Master_and_Sex_Kitten in Transgender & Crossdressers 05/12/2013
H
4.53
58.4k
35
10
44

A Thrilla in Manila

My Affair With a Ladyboy.

by EARTHFORCE in Transgender & Crossdressers 02/20/2013
0
49.2k
8
0
10
0

Ladyboy DP for Thai Wife

Sexy Thai gf agrees to share her Ladyboy lover with hubby .

by StarfireMayo in Transgender & Crossdressers 08/31/2012
4.19
112.7k
41
0
58
0

What Happens in Bangkok

Two brothers and a Thai hooker.

by daddyslittlebitch in Incest/Taboo 08/26/2012
H
4.57
97.4k
94
5
118
0

Cindrellas Kiss Ch. 02

She gets more than just a kiss.

by maanmathan_playboy in Transgender & Crossdressers 07/26/2012
4.39
29.2k
9
0
10

Ladyboy for my Thai Wife

I enjoy watching my Thai wife have sex with a ladyboy.

by StarfireMayo in Transgender & Crossdressers 06/25/2012
4.17
133.3k
63
3
89
0

Danielle's First Time

Daniel, a straight man discovers that he's a transsexual.

by FellatiaViper in Transgender & Crossdressers 01/31/2012
4.38
111.7k
46
9
59

Brainwashing for Small Cocks Ch. 01

He's captured and mind-fucked into becoming gay.

by Ginatheslut in Mind Control 01/09/2012
4.29
327.9k
166
48
246
0

The Bottom Tier: Ari and Cato

A new pair of lovers in a broken world.

by Cruel2BKind in Gay Male 09/04/2011
H
4.8
26.5k
16
17
24
0

Five Ring Circus

An evil crime and extreme retribution for tranny fans.

by bb1212 in NonConsent/Reluctance 07/27/2011
4.39
57.6k
40
2
47
0

Recruited Ch. 01

A ladyboy scouted and recruited to service men in the army.

by Rstyusameg in Transgender & Crossdressers 06/01/2011
H
4.51
60.1k
38
6
49
0

The Neighborhood Ladyboy Ch. 02

Local Asian crossdresser gets invited to the neighborhood.

by Rstyusameg in Transgender & Crossdressers 05/30/2011
4.34
44k
25
4
26

The Neighborhood Ladyboy Ch. 01

Local asian crossdresser taken behind the supermarket.

by Rstyusameg in Transgender & Crossdressers 05/23/2011
4.22
88.6k
47
6
59

The Bottom Tier Revisited

An epilogue to the Bottom Tier.

by Cruel2BKind in Gay Male 04/22/2011
H
4.7
22.7k
8
10
11

My Experience So Far

It's just a blowjob.

by PeterBenjamin in Transgender & Crossdressers 04/12/2011
3.49
57k
7
3
9
0

The Bottom Tier

In a world divided unfairly, the victims find love.

by Cruel2BKind in Gay Male 03/22/2011
H
4.75
41.8k
30
12
42

NOT Waiting For Godot XXX

Thai Ladyboy edition, a porn parody.

by eneo in Humor & Satire 01/18/2011
0
10.6k
2
0
2
0

Another Day, Different Office

A night alone in Amsterdam.

by chelseabi in Transgender & Crossdressers 09/19/2010
4.12
31k
9
0
11
0

Tilted Kilt Ch. 04

Danika experiences a Japanese Encounter.

by call_me_dana in Transgender & Crossdressers 08/10/2010
H
4.73
32.6k
13
5
13

A Slut Awakens

Girly boy is found out by his Black neighbor.

by BrockFlair in Transgender & Crossdressers 02/23/2010
H
4.54
249k
130
11
173

Shemale First Time

Shemale male first time sex.

by Canine51 in Transgender & Crossdressers 02/16/2010
4.25
669.9k
66
6
91
0

Punish the Freak

Marie needs to be punished for what she is.

by Sean Renaud in Transgender & Crossdressers 02/09/2010
3.93
53.8k
9
1
11
0

Amethyst: a Story of Fulfilment

Amethyst finds he's - err, she's leading an ideal life.

by frillypanty in Transgender & Crossdressers 01/23/2009
H
4.5
20k
6
2
8
0

Sex with Shonda

Clint picks up a hot shemale from the local club.

by rawpump in Transgender & Crossdressers 10/19/2008
4.17
94.1k
24
3
32
0

Guilty Pleasures

A drag queen submits to her boyfriend's perverted urges.

by trevorm in Transgender & Crossdressers 07/24/2008
4.03
78.5k
5
2
9
0

Twisted

Dallas and Eve put on a live performance at a ladyboy bar.

by StiffClit in Transgender & Crossdressers 03/27/2008
H
4.72
50.5k
24
1
31
0

Exotic Escapades Ch. 03

Tammy's adventures with a ladyboy and two men.

by exroticdistant in Transgender & Crossdressers 01/18/2008
4.13
34.6k
5
0
6

Bangkok Bar Girl

Businesman gets a surprise in a Thai bar.

by Pussyrider in Transgender & Crossdressers 06/21/2007
4.3
170.7k
34
2
46
0

Tomeric: The Kiss

He discovers hidden talents through an accidental kiss.

by gobula in Transgender & Crossdressers 09/14/2006
3.93
30.6k
7
1
7
0

A Cyber-Awakening

Online chat with mysterious lady leads to unexpected desire.

by fyredreams in Transgender & Crossdressers 03/28/2005
H
4.51
106.6k
39
0
46
0
12
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