SHEMALE • FIRST TIME 3,219 videos

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14:56

Domme T: first-ever Time rope-On Virgin

1 month ago

ShemaleTaxi

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11:21 78%

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2 years ago

TrannyOne

first time, hardcore
06:30 58%

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5 years ago

HDSex

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08:23 59%

Straight Guy Fucked By Trans Woman For First Time

1 year ago

ShemaleZ

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08:07

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1 month ago

PornDr

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10:01

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9 years ago

MyLust

first time
06:15

Jesse Pony first time having sex with a trans

11 months ago

UiPorn

first time
06:00

Young Thai transsexual Princess getting her ass fucked bareback for the first time tonight.

4 years ago

BravoTube

first time
08:12

My first time with a transsexual

3 months ago

JizzBunker

first time
06:54 72%

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1 year ago

TrannyOne

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14:29 76%

College Amateur Aubreys first Porn

5 years ago

TrannyGem

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01:28

Casting Guy First Time - Itzelxxx

6 months ago

TXXX

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04:30 79%

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2 years ago

TrannyOne

first time
08:00 56%

Christmas orgy first time Slumber Party

5 years ago

IcePorn

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08:00

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8 months ago

GetTranny

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08:19 65%

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7 months ago

xHamster

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10:36 68%

My First Time With My New Ejaculating Fantasy Dildo

10 months ago

BeMyHole

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05:18

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4 years ago

VideoSection

first time, hardcore
07:50 88%

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1 year ago

ShemaleMovie

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07:08

Beautiful STUDENT has HARD SEX FOR THE FIRST TIME and has multiple ORGASMS part 1

1 month ago

PornHub

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51:27 58%

Little ones first time - all 3 angles

4 years ago

TXXX

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32:17 83%

Helena Price - First Time With A Ladyboy Hd

2 years ago

ShemaleZ

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07:42

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

9 months ago

GetTranny

panties, first time
06:55

Joe Gets Female by First Time

6 years ago

ShemaleZ

first time
22:15

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1 month ago

ShemaleTaxi

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20:01 94%

Pretty young tgirl ass fucked by girl for the first time

5 years ago

PornHub

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06:20 58%

Teenager Trans and Beau very first Ravage

3 years ago

TrannyGem

teen anal (18+), first time
16:11

Is this your first time fucking a hot tranny

2 years ago

TrannyOne

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08:53

Crossdressers First Time

9 months ago

IcePorn

crossdresser, first time
07:47

Cutiepii33quinn ass screwed for first-ever time

1 month ago

VideoSection

anal, shemale, first time, couple
10:00 74%

Boy first time with tranny

12 years ago

xHamster

first time
12:00

Naughty Michael Delray fucks tranny for the first time

8 months ago

YourLust

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07:10

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1 month ago

ShemaleMovie

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08:58 57%

First Time swallowing cum

5 years ago

xHamster

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08:27

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3 years ago

TrannyGem

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12:08

My First Time With A Trans

1 year ago

BeMyHole

amateur, big tits, ass licking, first time, hardcore
10:42

Trans dame attempts to do anal first-ever first time

3 years ago

ShemaleTaxi

first time
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
31:37

Shy Couple first time shemale experience 2

4 years ago

AShemaleTube

couple, shy, first time
03:25

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

7 months ago

TrannyGem

amateur, femdom, teen (18+), deepthroat, first time, femboy
21:59 85%

Trans nailing a heterosexual stud for the first-ever time

6 months ago

TrannyGem

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08:09 60%

My very first time

2 years ago

TrannyOne

first time
15:58

Ladyboy fuck a white dude in ass

3 years ago

PornHub

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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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14:09 72%

Venus Lux Fucks First Time Bottom JakeD

5 months ago

IcePorn

first time
15:57

The first time

7 months ago

AShemaleTube

amateur, POV, first time
21:06 75%

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

2 years ago

TrannyOne

first time
23:22 80%

Fucked for the First Time

3 years ago

BeMyHole

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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

smoking, gagging, deepthroat, cum in mouth, taxi, first time
18:50

AUBREYS FIRST-EVER TIME

3 years ago

TrannyGem

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05:58

First time teen experience Janine smashing an older guy

2 years ago

TrannyOne

first time, teen (18+)
18:47

The Pill Episode 2 - Chris First Time

7 months ago

JizzBunker

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05:17

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3 years ago

AShemaleTube

first time
06:05 75%

Your First Time Getting Fucked By A Trans Girl: First Date Gfe Pov Femdom

10 months ago

ShemaleZ

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08:15

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4 years ago

VideoSection

first time
08:10

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2 weeks ago

ShemaleMovie

first time, teen (18+), strapon, shemale
04:18

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

1 month 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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10:43 74%

Girl tries to fuck with trans first time

4 years ago

AShemaleTube

first time
23:47 65%

Guys first Time with Tgirl

2 years ago

TrannyOne

69, first time
07:01

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

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
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
16:00 77%

Femdom Ts Initiation: First Time Fuckers

3 years ago

ShemaleZ

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07:19

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3 years ago

ShemaleTaxi

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08:01

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2 years ago

TrannyOne

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08:01

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2 years ago

TrannyOne

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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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05:01

Tranny is trying Anal for the first time

5 years ago

AShemaleTube

first time
08:44

Crossdressers First Time

2 years ago

TrannyOne

crossdresser, first time
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
05:13

Lena And A Married Males First Time

1 year ago

TXXX

amateur, POV, first time
06:01

Inked homo plowed passionately for first time by Asian TS

2 years ago

TrannyOne

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

wife, first time
08:00

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5 years ago

IcePorn

first time
05:54

Bashful French sissy first-ever time to fellate

1 year ago

ShemaleTaxi

french, taxi, sissy, first time
02:28 53%

Sissy Lexie Adams Crossdresser First Time with Sex Machine

1 year ago

xHamster

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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
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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14:19

Is this really your first time with a t-girl

3 years ago

ShemaleMovie

first time
14:51 74%

Sophie & Quinns Very First Time

2 years ago

KeekAss

shemale, lesbian, shemale and girl, first time
05:49

The First Time He Fucks With A Trans 6 Min

1 year ago

Upornia

first time
44:37

Sex Tourist Bangs A Shemale For The First Time

2 years ago

HClips

threesome, first time, brunette
25:45

FUTANARIA FIRST TIME FUCK BUDDIES

3 years ago

ShemaleZ

first time
06:02

BEST. Very hot cumshot handless and in a marvellous pose

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xHamster

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05:26

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5 days ago

xHamster

lingerie, crossdresser, first time
1:40:20

My first time with a transexual Full Hd Version Directors Cut

3 months ago

JizzBunker

first time
05:17 53%

Cd and Str8 First time

5 years ago

TXXX

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03:01

His First Time with a Tgirl - Tyra Scott

9 years ago

xHamster

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14:09

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

4 years ago

VideoSection

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03:48

Blonde gurls first time.

4 years ago

ShemaleZ

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13:25

His very first time with a ladyboy

5 years ago

HDSex

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46:35

First Time With A Shemale

3 years ago

BeMyHole

first time
16:52

My first Time

2 years ago

TrannyOne

first time
03:01

Lemmis First Time!

1 year ago

HClips

first time
10:10

Stepbro Analed Ts Stepsis For First Time

1 year ago

ShemaleZ

anal, first time
03:41 60%

Anonymous Random Grindr Fuck - First Time With Trans

11 months ago

ShemaleZ

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15:10

My first time as a sissy was so liberating

1 year ago

ShemaleTaxi

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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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06:20

Teen guy sucking tranny cock first time

2 years ago

TrannyOne

teen (18+), first time
17:25

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

3 years ago

xHamster

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06:15

We had a first time threesome with a tranny woman

1 year ago

TrannyOne

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01:20

My first time as a CD

11 years ago

AShemaleTube

first time
32:59

Helena Price 1st Time Transgender dame

5 months ago

ShemaleTaxi

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15:00

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5 months ago

XoZilla

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14:09

Femboy rides 7 inch dildo for first time

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PornHub

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06:15

First time with a Shemale Escort

2 years ago

TrannyOne

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07:07

Redhead shemale fucks her dates ass for the first time

2 months ago

TrannyGem

first time
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
05:32 54%

First time

4 years ago

xHamster

mature, amateur, mature anal, first time
01:21 64%

Arab Femboy First Time Anal

3 years ago

AShemaleTube

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12:37

Top trans model Arianna Jade fellating off Canadian jock in a hotel

3 years ago

VideoSection

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15:30

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11 months ago

xHamster

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11:33

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3 years ago

AShemaleTube

first time
06:56

Irresistible SheBabe to be fuck for first time Part2

2 years ago

DrTuber

first time
06:12

Busty teen sheshaft first time takes big cock

3 years ago

AShemaleTube

first time
07:49

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

3 weeks ago

BeMyHole

first time, 18, asian, uniform
03:53

Bot Having Sex For The First Time With Tranny

11 months ago

GetTranny

first time

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