SHEMALE • FIRST TIME 3,192 videos

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20:01 93%

Pretty young tgirl ass fucked by girl for the first time

4 years ago

PornHub

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14:56

Domme T: first-ever Time rope-On Virgin

2 weeks ago

ShemaleTaxi

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11:21 78%

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2 years ago

TrannyOne

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06:30 56%

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5 years ago

HDSex

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08:12

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3 months ago

JizzBunker

first time
10:36 68%

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10 months ago

BeMyHole

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12:00

Naughty Michael Delray fucks tranny for the first time

7 months ago

YourLust

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15:58

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3 years ago

PornHub

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15:00

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4 months ago

XoZilla

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15:00

Asian Tranny First-Time Fantasy part 1 - Sharnell Dupree

9 months ago

xHand

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14:29 74%

College Amateur Aubreys first Porn

5 years ago

TrannyGem

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06:54 71%

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1 year ago

TrannyOne

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01:28

Casting Guy First Time - Itzelxxx

6 months ago

TXXX

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08:23 56%

Straight Guy Fucked By Trans Woman For First Time

1 year ago

ShemaleZ

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08:00 56%

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5 years ago

IcePorn

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08:00

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8 months ago

GetTranny

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08:19 62%

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7 months ago

xHamster

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04:30 79%

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2 years ago

TrannyOne

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05:18

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4 years ago

VideoSection

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07:50 88%

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1 year ago

ShemaleMovie

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07:42

He Wears My Panties For The First Time Pov - Teaser Video

9 months ago

GetTranny

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32:17 82%

Helena Price - First Time With A Ladyboy Hd

2 years ago

ShemaleZ

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51:27 57%

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3 years ago

TXXX

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07:47

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2 weeks ago

VideoSection

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22:15

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3 weeks ago

ShemaleTaxi

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06:55

Joe Gets Female by First Time

6 years ago

ShemaleZ

first time
16:11

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2 years ago

TrannyOne

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31:37

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4 years ago

AShemaleTube

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03:20 59%

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7 months ago

TrannyGem

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10:00 74%

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12 years ago

xHamster

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06:20 58%

Teenager Trans and Beau very first Ravage

3 years ago

TrannyGem

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06:03

From Shy to Slay: Crossdresser Kitty's Personal Transformation Stories!

Today

xHamster

shemale
08:58 57%

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5 years ago

xHamster

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04:18

Mia Thorne Trains Cherry Tgirl Mate How to Have Hook-Up UTTER MOVIE ON FANSLY

2 weeks ago

TrannyGem

amateur, small cock, shemale, lesbian, asian, shemale and girl, small tits
12:08

My First Time With A Trans

1 year ago

BeMyHole

amateur, big tits, ass licking, first time, hardcore
28:10 73%

My Trans Girlfriend Fucks Me For The First Time. She I Love How She Fucks My Ass

5 months ago

ShemaleZ

amateur, redhead, girlfriend, first time
03:25

Teenie Ginger-Haired uses a String on for the First-Ever Time!(more Content Coming Shortly)

6 months ago

TrannyGem

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09:08 78%

Inked mans first-ever Time With a Trans Girl: Blows His Load and His Mind over a Smoking Blowjob

1 year ago

ShemaleTaxi

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10:42

Trans dame attempts to do anal first-ever first time

3 years ago

ShemaleTaxi

first time
23:22 80%

Fucked for the First Time

3 years ago

BeMyHole

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08:09 60%

My very first time

2 years ago

TrannyOne

first time
14:09 72%

Venus Lux Fucks First Time Bottom JakeD

4 months ago

IcePorn

first time
15:57

The first time

6 months ago

AShemaleTube

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06:15 88%

Getting Dominated And Sucking Cock For The First Time Like A Little Slut With Facial 7 Min

1 year ago

ShemaleZ

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16:00 77%

Femdom Ts Initiation: First Time Fuckers

3 years ago

ShemaleZ

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08:07

I try my transsexual friends cock for the first time

3 weeks ago

PornDr

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21:06 74%

Hot guy gets his ass plowed for the first time by a nasty shemale beauty

2 years ago

TrannyOne

first time
08:15

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4 years ago

VideoSection

first time
18:47

The Pill Episode 2 - Chris First Time

7 months ago

JizzBunker

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21:59 84%

Trans nailing a heterosexual stud for the first-ever time

5 months ago

TrannyGem

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05:58

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2 years ago

TrannyOne

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05:17

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3 years ago

AShemaleTube

first time
18:50

AUBREYS FIRST-EVER TIME

3 years ago

TrannyGem

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08:01

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2 years ago

TrannyOne

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10:43 74%

Girl tries to fuck with trans first time

4 years ago

AShemaleTube

first time
05:36

Confidence is Key: Embrace Your Unique Style with Crossdresser Kitty!

Today

xHamster

shemale, crossdresser, teen (18+)
07:01

Teen girl tricked guy into sex first time Border-hopping Latina bitch

2 years ago

TrannyOne

first time
08:27

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3 years ago

TrannyGem

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34:39 55%

Trans plowing 2 gals for the first time ~KimberlyGeorge~

1 year ago

VideoSection

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23:47 63%

Guys first Time with Tgirl

2 years ago

TrannyOne

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07:19

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3 years ago

ShemaleTaxi

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05:01

Tranny is trying Anal for the first time

5 years ago

AShemaleTube

first time
03:23

First Time Fucked by a Shemale

4 years ago

ShemaleZ

18, first time
18:51

Fucked by a man for the first time.

3 years ago

ShemaleZ

POV, first time
08:01

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2 years ago

TrannyOne

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08:44

Crossdressers First Time

2 years ago

TrannyOne

crossdresser, first time
05:13

Lena And A Married Males First Time

1 year ago

TXXX

amateur, POV, first time
05:30

My wife pummeled me in the butt for the first-ever time, but I even liked it

1 year ago

ShemaleTaxi

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17:35

Young dude screwed in the ass for the first time by a tranny

3 years ago

ShemaleMovie

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05:54

Bashful French sissy first-ever time to fellate

1 year ago

ShemaleTaxi

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02:28 53%

Sissy Lexie Adams Crossdresser First Time with Sex Machine

1 year ago

xHamster

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06:01

Inked homo plowed passionately for first time by Asian TS

2 years ago

TrannyOne

first time
08:01

Rough violent gangbang crying first time Sometimes it takes a stranger

2 years ago

TrannyOne

stranger, first time
31:51

First-ever time for youthfull hetero Latino to be fucked by transsexual Latina

1 year ago

ShemaleMovie

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16:43

Feels Like The First Time . . .

3 years ago

xHamster

first time
10:01

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9 years ago

MyLust

first time
44:37

Sex Tourist Bangs A Shemale For The First Time

2 years ago

HClips

threesome, first time, brunette
09:06

(Part 1) Very First Time Degustating My Own Spunk And Guzzling Urinate, Jizz On Food Fetish, Chinese Transgender Trap She-Creature

11 months ago

KeekAss

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14:51 74%

Sophie & Quinns Very First Time

2 years ago

KeekAss

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05:49

The First Time He Fucks With A Trans 6 Min

1 year ago

Upornia

first time
14:19

Is this really your first time with a t-girl

3 years ago

ShemaleMovie

first time
16:52

My first Time

2 years ago

TrannyOne

first time
1:40:20

My first time with a transexual Full Hd Version Directors Cut

3 months ago

JizzBunker

first time
17:52

Lady sextasy experiences transgender intense fucking for the first time also enjoys it

2 years ago

TrannyOne

first time, hardcore
25:45

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3 years ago

ShemaleZ

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05:17 53%

Cd and Str8 First time

5 years ago

TXXX

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08:00

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5 years ago

IcePorn

first time
14:09

This will be our very first time drilling a t-girl

4 years ago

VideoSection

first time
13:25

His very first time with a ladyboy

5 years ago

HDSex

asian, nylon, first time
07:07

Redhead shemale fucks her dates ass for the first time

2 months ago

TrannyGem

first time
21:45

Guy first time with blonde Tgirl

13 years ago

AShemaleTube

first time
03:01

His First Time with a Tgirl - Tyra Scott

9 years ago

xHamster

first time
11:30

Beauty Fucks For Her First Time With A Trans And Its Korra - Spencer Bradley And Korra Del Rio

1 year ago

TXXX

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03:48

Blonde gurls first time.

4 years ago

ShemaleZ

teen (18+), couple, blonde, first time
05:24

Fashion Forward: Styling Tips for the Modern Crossdresser!

Today

xHamster

shemale
26:23

Tranny fucks a little trans for the first time on the New Year

1 month ago

JizzBunker

small cock, tattoo, shemale, first time, beauty
03:41 60%

Anonymous Random Grindr Fuck - First Time With Trans

11 months ago

ShemaleZ

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06:20

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2 years ago

TrannyOne

teen (18+), first time
06:15

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1 year ago

TrannyOne

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15:37

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1 year ago

Upornia

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17:25

Young guy fucked in the ass for the first time by a tranny

3 years ago

xHamster

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03:01

Lemmis First Time!

1 year ago

HClips

first time
01:20

My first time as a CD

11 years ago

AShemaleTube

first time
10:10

Stepbro Analed Ts Stepsis For First Time

1 year ago

ShemaleZ

anal, first time
32:59

Helena Price 1st Time Transgender dame

4 months ago

ShemaleTaxi

shemale, first time
46:35

First Time With A Shemale

3 years ago

BeMyHole

first time
15:30

I arrived by surprise. It was his first time sucking a shemale

10 months ago

xHamster

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06:15

First time with a Shemale Escort

2 years ago

TrannyOne

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12:37

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3 years ago

VideoSection

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06:12

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3 years ago

AShemaleTube

first time
01:21 64%

Arab Femboy First Time Anal

3 years ago

AShemaleTube

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06:56

Irresistible SheBabe to be fuck for first time Part2

2 years ago

DrTuber

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06:00

Amateur Porn Ladyboy First Time On Cam Bareback Butt Sex

2 years ago

ShemaleZ

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05:32 54%

First time

4 years ago

xHamster

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05:01 58%

Old man eats teen ass first time Frannkie's a fast learner!

2 years ago

TrannyOne

teen (18+), old man, first time
11:33

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3 years ago

AShemaleTube

first time
07:49

Young Time Lady-boy... First Experience!!!!

6 days ago

BeMyHole

first time, 18, asian
15:54

SOMEONES SPUNKING

2 years ago

TrannyGem

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07:05

My First Time With A Trans. Part 2

7 months ago

ShemaleZ

teen (18+), 18, first time
08:00

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2 months ago

IcePorn

teen (18+), POV, first time

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