SHEMALE • FIRST TIME 4,346 videos

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06:15

You looks like a virgin! - Donte Thick and TS Roxxie Moth

5 years ago

xHamster

first time
12:46

Pounding my Trans gf Cassie with a Mr Hankeys faux-cock

4 years ago

ShemaleTaxi

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10:56

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2 years ago

ShemaleMovie

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06:01

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4 years ago

TrannyOne

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05:12

Trans Ultra-Cuties First-Ever Time Humping Another Trans Gal - Emma Rose + Jasmine Lotus

2 years ago

TrannyGem

first time
09:40

Get back to you for the first time with a genuine transvestite

8 years ago

JizzBunker

first time
06:24

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2 years ago

ShemaleTaxi

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13:36

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3 years ago

ShemaleZ

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05:08

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3 weeks ago

ShemaleMovie

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05:26

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2 years ago

xHamster

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08:14 50%

First-time at the porn cinema followed by a hookup with a transgender princess

7 months ago

XXXVogue

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15:58

I Will Make Your Very First Time With A transgirl Memorable

5 years ago

TrannyGem

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07:32

Teen Masseuses First Time With Trans Client With Spencer Bradley And Jenna Gargles

3 years ago

TXXX

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12:30

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7 years ago

xHamster

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15:18 82%

BEGINNER TRANSE ZUM ERSTEN MAL IN DEN ARSCH GEFICKT UND BESAMT ASS JOB

4 years ago

TrannyGem

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03:08

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2 years ago

TXXX

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08:08

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1 year ago

xHamster

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08:12

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6 years ago

VideoSection

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09:57

The First Time The Doll Fucked A Pussy, Was It A Lesbo?

1 year ago

BeMyHole

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12:10

First Time In Bed With A Transvestite

2 years ago

JizzBunker

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06:00 57%

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

6 years ago

BravoTube

first time
06:15

Small tits shemale Jade Downing analed

3 years ago

TrannyGem

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05:24

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5 years ago

xHamster

first time
05:27

First to Cum Challenge - Veronica Sanders

1 year ago

xHamster

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04:20 72%

Old man partners daughter and tranny first time Alyssa Gets Her Way With

7 years ago

TXXX

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06:53

First-time Fantasy - Sharnell Dupree

4 years ago

ShemaleZ

first time
04:26

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4 years ago

TrannyOne

first time
05:13

Hot 18 year old young man tries his hottest friends cock for the first-ever time when there is no one in his mansion

10 months ago

ShemaleMovie

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16:29

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8 years ago

xHamster

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06:38

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1 year ago

ShemaleTaxi

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12:56

She made me spunk twice! first-ever time pummeling Britney from Tantaly - Emily Adaire

9 months ago

ShemaleMovie

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11:07 63%

First Time Teacher of Magic and Alice Blitz ( part 2 )

6 years ago

HClips

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05:29

Elegant transsexual gets fucked by a guy for the first time

12 years ago

AShemaleTube

amateur, first time
09:48

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8 months ago

ShemaleMovie

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06:38

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11 months ago

ShemaleTaxi

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07:41

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3 years ago

GetTranny

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22:37

TRANNY SHEMALE FUCKS STRAIGHT GUY - FIRST TIME TRANSSEXUAL FUCKING

3 years ago

xHamster

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02:06

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4 years ago

AShemaleTube

first time
2:36:25 60%

Yui Hatano And Hibiki Otsuki - Dass-133 First Time Nh Lesbian Sex. Kanami Kashiwagi Yu

2 years ago

ShemaleZ

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06:29

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6 months ago

TrannyGem

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08:28

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5 years ago

BeMyHole

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26:24

Ladyboy nails Petite transgirl for the first time in the New year

2 years ago

ShemaleTaxi

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05:33

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5 years ago

VideoSection

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05:45

Kasey Kei - Tattooed Guy Enjoys His Very First Time Of Trans Transaction

3 years ago

ShemaleZ

first time
20:31

Blonde for the first time

8 years ago

ShemaleZ

first time
05:45

Lena Moon - His First Time With A Tranny

3 years ago

ShemaleZ

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07:12 63%

Very first Time in Public

5 months ago

ShemaleMovie

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35:43

Ultra-Cute Transgender Princess first-ever Time Audition Call with Ebony Dom

6 years ago

KeekAss

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05:01

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4 years ago

TrannyOne

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22:53

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2 weeks ago

ShemaleMovie

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08:14

Killer Colombian

3 weeks ago

ShemaleMovie

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07:23

Lesbian Roomate Fucks Her Trans Girlfriend In Anal! Transgender First Time Fucks With A Roomate

4 years ago

TXXX

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07:06

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1 year ago

ShemaleMovie

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07:59

Big Tit Tranny Kawane Fucks Guy In Tight Asshole For The First Time

1 month ago

GetTranny

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13:11

My first time being filmed! Solo playtime taunt

10 months ago

ShemaleMovie

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05:43

First-time femboys experience multiple orgasms with sex toys

3 months ago

XXXVogue

femboy, first time
16:11 67%

FtM Youngster Wants Ass Fucking

5 months ago

TrannyGem

amateur, teen (18+), POV, teen anal (18+), orgasm, british, ass
08:00

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

2 years ago

GetTranny

first time, amateur
06:38

Z Fucks My Ass with a Strapon (his first time!)

6 years ago

HClips

strapon, first time
13:19

Satans TGIRLS - beautiful Marilyn Johnson accomplished Sex With A Trans Girl For The First Time

1 year ago

ShemaleTaxi

blowjob, shemale and girl, first time
12:53 82%

She made me spunk two times! Very First time fuckin Britney from Tantaly - Emily Adaire

5 months ago

TrannyGem

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06:26

Fiona wooing Me To Not poke Her junior Teenager Roommate Girl On The Way to Beach

1 month ago

ShemaleMovie

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12:35

Ladyboystar - I boned and inhaled this super-fucking-hot tranny in POINT OF VIEW fashion

1 month ago

TrannyGem

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10:06 71%

Dorian Drake gets barebacked for the first time by big cock from trans girl pv

3 months ago

AShemaleTube

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12:53

I am sexually aroused about my very first time with a she-creature

7 years ago

HDSex

bisexual, first time
05:32

Ladyboy Jusmin Fucked Bareback

1 year ago

BeMyHole

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05:17

White Shemale Sissy Crossdresser Girl Body Mini Skirt Hot Slut Blonde Kitty

1 year ago

xHamster

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07:00

Young girl big tits fucking old man first time Old clever ge

7 years ago

IcePorn

old man, old and young (18+), first time
06:34

My First Time in Tights: Embracing My Crossdressing Journey!

2 years ago

xHamster

first time
10:19

Meets Her Stepbro For The First Time And In No Time Gets His Cock Out To Suck - Trans - Angel S, Izzy Wilde And Sage Roux

2 years ago

ShemaleZ

outdoor, first time
14:48 75%

My internet buddy has intercourse for the first-ever TIME with a trans girl and his femboy friend gets all his CUM in his face

1 month ago

ShemaleMovie

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06:57

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8 years ago

ShemaleZ

teen anal (18+), first time
05:51

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2 years ago

xHamster

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04:04

Honey Trans In First Time Teen 18+ Tgirl Uses Toy Machine And Strokes Cock

7 months ago

Fuxxx

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28:31

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

2 years ago

ShemaleZ

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05:59

Real Straight Fucked Bareback By 2 Latinas Shemales For The First Time - ShemaleVideos

2 years ago

TXXX

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19:27

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3 years ago

ShemaleMovie

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06:29

First Time Fembois with Thayane Beck for TrannyBizzare

1 year ago

xHamster

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03:52

First time using a vibrator, I came SO much

2 years ago

xHamster

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23:43

First Time Double Penetration After 25 Days Without Touching Myself. I Cant Get Enough! Stoner Fav

3 years ago

ShemaleZ

fetish, first time, double penetration
09:16

My First Time With A Trans. Part 3. I Fuck Her Rich Ass

2 years ago

BeMyHole

teen anal (18+), latina, ass licking, first time, teen (18+)
06:25

Holy hell, what a super-hot three-way with mummy Dee Williams. This is the first time that Ellas met Dr. Williams and they are understandably a bit nervous. Dr. Williams do everything she can to put Ella at ease

4 years ago

ShemaleMovie

teen (18+), threesome, teen anal (18+), first time
02:10

First Time Rapper Fucks Trans Woman in Chastity

3 years ago

xHamster

BDSM, first time, chastity
09:12

HIS FIRST TIME WITH A WOMAN WITH A DICK

3 years ago

xHamster

first time
36:47

Kendall Cent - Submits For The First-Ever Time

5 years ago

TrannyGem

first time
13:38

Eveline Moura - Sexy Shemale Has Her First Time With New Boyfriend

1 year ago

BeMyHole

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10:40

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8 months ago

AShemaleTube

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35:27

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2 weeks ago

XXXVogue

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05:18

Voluptuous ladyboy ditzy loses her mind of xxx anal

1 year ago

ShemaleMovie

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06:15

Pretty lady Cadence sucks a tranny cock for the first time

4 years ago

XXXDan

first time
05:09

Warm Tranny Khloe Hart rectal nails Dutch her first-ever time topping and gets dual jizz shot activity

3 weeks ago

TrannyGem

hardcore, first time, ladyboy, anal, dutch
06:40 67%

Lady with a rock hard lollipop rides step daddy

11 months ago

ShemaleTaxi

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11:15 71%

Fuck stick in the bum, onanism and jizm first-ever time using a fucktoy, its joy. My femboy booty was highly open

2 years ago

TrannyGem

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05:22

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4 years ago

AShemaleTube

first time
10:49

I WENT TO VISIT MY TRANS FRIEND AND WE HAD SEX FOR THE FIRST TIME I GAVE HER MY ASS AND TOOK CUM IN MY MOUTH

7 months ago

BeMyHole

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16:19

First time

8 years ago

ShemaleZ

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39:51

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2 years ago

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44:47

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2 years ago

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06:10

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7 years ago

DrTuber

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15:02 69%

Rail with a stunning and super-sexy trans Isabella Salvatore

1 month ago

TrannyGem

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12:10

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2 years ago

ShemaleTaxi

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05:11

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3 years ago

xHamster

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05:01

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4 years ago

TrannyOne

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20:45

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4 years ago

TrannyGem

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06:01

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4 years ago

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33:14 43%

My Hot Online Asian Girlfriend! Were Meeting For The First Time And She Forgot To Tell Me She Has A Cock!

1 year ago

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24:39

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2 years ago

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03:47

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5 months ago

AShemaleTube

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03:02

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6 years ago

TXXX

first time
06:40

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10 months ago

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3 years ago

xHamster

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23:54

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5 years ago

VideoSection

first time
20:26 40%

I Record While I Fuck For The First Time With My Transsexual Girlfriend 20 Min

2 years ago

ShemaleZ

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11:54

My First Time Fucking A Woman!!

6 months ago

ShemaleZ

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08:14

We Did an Interracial Threesome for the first Time with My finest buddy BBC

2 months ago

ShemaleTaxi

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05:31 50%

Jessica Having anal fuckfest With 18 Plus Max

3 months ago

ShemaleTaxi

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05:12 50%

My Trans Step mother swallows My cum Medicine Methodically

2 months ago

ShemaleTaxi

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03:11

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2 years ago

xHamster

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08:01

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4 years ago

TrannyOne

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07:05

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4 years ago

AShemaleTube

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