‘ladyboy’ stories

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ladyboy 

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Filipina Pre and Post Op!

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

4.42
5.3k
6
1
8
0

My First Ladyboy

Straight alpha male falls for a sexy Filipino ladyboy.

4.41
38.8k
28
7
43
0

Quinn

A young cross dresser transforms.

4.41
51.6k
52
6
66

A Surprise in the Massage Parlour

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

4.41
12.1k
10
2
24
0

He Said, She Said Ch. 08

A surprise guest for the evening.

4.4
6.2k
2
3
3

Turned into a Sissy Pt. 01

How my ladyboy girlfriend turned me into a Sissy.

4.4
97.7k
103
20
209

The Club

They thought they were just going to watch...

4.39
54.5k
36
4
48
0

In The Moment, Things Change

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

4.39
44.3k
25
6
29
0

Five Ring Circus

An evil crime and extreme retribution for tranny fans.

4.39
57.7k
40
2
47
0

Closed for Business Ch. 01

Dara realizes she's fresh out of shaving cream.

4.39
7.6k
4
0
9

T-girl's Double Date

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

4.38
55.2k
33
1
41
0

Danielle's First Time

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

4.38
111.7k
46
9
59

Filipina Fun! Pt. 02

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

4.38
9.4k
5
1
6

A Prisoner to the Middle Sex

One man in Bangkok, and his ladyboy prisoners.

4.37
59.1k
49
5
64
0

Lin

A trip to Thailand for some forbidden fun.

4.37
49.3k
21
0
29
0

Tranny Babysitter: The Conclusion

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

4.37
22.8k
14
0
33
0

Cummy Panties

Erotic encounter at a bar.

4.37
64.7k
46
14
52
0

Makati Ch. 08

An American's adventure in Makati.

4.36
6.8k
00
1

My First Ladyboy Experience

How a massage opened more than my mind.

4.36
52.3k
23
3
42
0

The Neighborhood Ladyboy Ch. 02

Local Asian crossdresser gets invited to the neighborhood.

4.34
44.1k
25
4
26

Face Down Ass Up

Leslie takes control and lets me feel all of her.

4.33
39.7k
31
5
49
0

Eucalyptus Club

Exclusive sex club in the glens.

4.33
9.5k
4
2
11

Girls Vegas-Style

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

4.31
87.8k
31
8
42
0

Sissy's First Trip Out

A sissy excursion leads to an unexpected meeting.

4.29
25.7k
11
5
24
0

Bangkok Bar Girl

Businesman gets a surprise in a Thai bar.

4.29
170.8k
34
2
46
0

Brainwashing for Small Cocks Ch. 01

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

4.29
328.1k
166
48
246
0

Bottom Bitch Is Bred By His Dom Top

A bottom bitch experiences joy servicing his dominant top.

4.27
48.5k
23
6
45
0

My Transgender Love: Week 1

The first week of my vacation with my transgender girlfriend.

4.26
17k
12
4
17
0

My Sexy Changes Ch. 04

Male discovers his female-self.

4.26
49.4k
12
5
14

Shemale First Time

Shemale male first time sex.

4.25
670.3k
66
6
91
0

The Neighborhood Ladyboy Ch. 01

Local asian crossdresser taken behind the supermarket.

4.22
88.7k
47
6
59

Letter from Ravenswood Bluff

Mistress Jessamyn tells all.

4.2
9.8k
2
0
6
0

The Reunion Ch. 02: Thai Massage

Krissy relaxes with a massage with an unexpected ending.

4.19
26.1k
5
0
9

Ladyboy DP for Thai Wife

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

4.19
112.8k
41
0
58
0

Ladyboy for my Thai Wife

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

4.17
133.4k
63
3
89
0

Sissy Sold in Thailand

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

4.17
36.9k
29
8
69

Sex with Shonda

Clint picks up a hot shemale from the local club.

4.16
94.1k
24
3
32
0

Surprise Fuck with Niece's Friend

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

4.16
43.7k
19
1
35

A New Adventure... Ch. 02

A little experimenting never hurt anyone.

4.14
19k
11
0
14

Okaikei

Coming home after a business trip.

4.13
21.1k
7
0
7
0

A Sinful Family Ch. 01 - Moving In

A filthy rich family full of incest and intrigue.

4.12
97.9k
110
18
164

Exotic Escapades Ch. 03

Tammy's adventures with a ladyboy and two men.

4.11
34.6k
5
0
6

Hero's Welcome

A soldier comes home to meet a new friend.

4.1
35.3k
17
0
26
0

Filipina Fun! Pt. 03

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

4.09
4.9k
1
0
1

Lois Has to Stay After Class Ch. 01

A senior at school, relaxed sexual adventures.

4.07
14.3k
7
1
9
0

My Cleaner Ch. 02

Married man seduced by ladyboy.

4.05
47.9k
16
0
20

Guilty Pleasures

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

4.03
78.5k
5
2
9
0

My Sexy Changes Ch. 04.2

Make embraces his feminine side.

4.03
42.4k
10
1
10

Ts Tasha Jones Takes Huge Cock

An encounter when I was a stripper.

4.01
80.1k
33
4
46
0

Hot Ladyboy Meet

A young guy meets a hot Asian ladyboy.

4
32.1k
14
2
25
0

My Cleaner

Married man seduced by ladyboy.

3.98
83k
32
4
42

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
0

From John to Jenny

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

3.95
55.8k
18
3
36
0

Sissy Sold in Thailand Pt. 02

Eric tried an escape with his new friend.

3.93
11.5k
7
4
10

Tomeric: The Kiss

He discovers hidden talents through an accidental kiss.

3.93
30.6k
7
1
7
0

Punish the Freak

Marie needs to be punished for what she is.

3.93
53.9k
9
1
11
0

The Bamboo Ceiling Ch. 12

A sissy is trained at a brothel.

3.86
15.4k
11
12
18

Banker's First Encounter

Banker seduced by ladyboy customer.

3.79
46.9k
14
2
16
0

Lois and Veronica

The glamour girls visit the forest ranger.

3.75
11.6k
4
1
8
0

Letter from Dayton

From a Young Male Master of Naughty Boys!

3.45
13.7k
4
0
5
0

The Shemale Possession

A man possesses the body of a "woman".

0
22.7k
13
5
19
0

The Awakening

My first time with a ladyboy.

3.05
10.1k
4
6
6
0

Soup Style Bk. 07 - Hide or Not?

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

3
1.2k
00
1
0

Bangkok Ladyboy Voodoo Doll App!

One night of going FULL RETARD in BANGKOK!

2.13
7.6k
2
1
5
0

NOT Waiting For Godot XXX

Thai Ladyboy edition, a porn parody.

0
10.6k
2
0
2
0
12
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