SHEMALE • FIRST TIME 3,997 videos

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22:39

Young Guy Fucks Blonde Latin Shemale Anal for the First Time

3 weeks ago

AShemaleTube

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10:13 64%

Real Transgender Gal Gets Ass-Fuck Smash

2 years ago

TrannyGem

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14:19

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5 years ago

ShemaleMovie

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05:58

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4 years ago

TrannyOne

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16:20

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3 years ago

ShemaleZ

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07:41

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13 years ago

AShemaleTube

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05:57

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9 years ago

DrTuber

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11:39

Stiff Times At Sequoia State Park Ep 8 - Very First Time Anal Invasion And She IDOLIZES It! by Foxie2K

7 months ago

TrannyGem

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27:19 44%

Fucking A T-girl For The First Time With Renata Barbosa And Fernandinha Fernandez

1 year ago

ShemaleZ

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03:01

FEMOUT GONZO: Lemmis Very First Time!

3 years ago

KeekAss

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15:46 67%

Turning My husband Into Tranny tart, lady first time with Tranny

1 year ago

ShemaleMovie

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10:03

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9 years ago

xHamster

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16:11

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5 years ago

TrannyGem

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10:43 40%

Huge cock pumps out an eighteen year old trans girls ass for the first-ever time

11 months ago

ShemaleMovie

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06:25

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5 years ago

HDSex

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05:10

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6 years ago

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10:45

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7 years ago

xHamster

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12:24

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8 years ago

ShemaleZ

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04:56

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2 years ago

ShemaleZ

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32:10

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3 months ago

ShemaleMovie

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17:19

Strikingly Stunning T-Girl is Providing me a Flawless Oral Pleasure

5 years ago

TrannyGem

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06:14

Ladyboy Jusmin First Time Anal

11 years ago

DrTuber

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06:10

Huge-Boobed Ash-Blonde TRANSSEXUAL Kayleigh Coxx first-ever time tearing up a fuckbox

6 years ago

TrannyGem

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04:21

Crossdresser Lea First Time Fucked In All Angles

3 years ago

ShemaleZ

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11:17

THE first TIME YOU NEVER leave behind

5 months ago

ShemaleTaxi

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38:26

Hammering Deep First Time In That Enormous Moist Pooper Of Blond Bombshell Aubrey

3 years ago

ShemaleZ

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08:14

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

3 months ago

XXXVogue

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25:36

Hellos First Time With fantastic lady-twink

7 years ago

ShemaleZ

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09:48

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4 months ago

ShemaleMovie

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11:32

Very First Time Educator of Magic and Alice Blitz ( part two )

4 years ago

TrannyGem

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13:25

First-Ever Time Tutor of Magic and Alice Blitz ( part 1 )

4 years ago

TrannyGem

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11:37

Korra And Spencer Run Inside To Have Steamy, Exploratory Sex With Strap-ons And Cocks Alike. Judging By Spencers Lovely Reactions, This Might Be The First Of Many Trans Encounters For Her.

1 year ago

BeMyHole

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06:07

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2 years ago

TrannyOne

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06:38

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9 months ago

ShemaleTaxi

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10:43 66%

Girl tries to fuck with trans first time

6 years ago

AShemaleTube

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22:07

FIRST-EVER TIME WITH MY FRESH FUCK-FEST MACHINE ASS FUCKING

1 year ago

TrannyGem

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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

6 months ago

ShemaleMovie

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36:43

Kendall Penny - Submits for the First Time

6 years ago

ShemaleZ

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12:17

You will never leave behind your very first time with she-creature babe Mel

6 years ago

HDSex

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04:58

Nice transsexual first-time fucked

4 years ago

AShemaleTube

first time
05:24

Gargle Her Meatpipe - Tgirl Manstick Fellating Encouragement - Imposed Bisexous

6 months ago

TrannyGem

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10:36

My Little Stepbrother Has His First Time With A Trans And I Help Him By Lending Him My Ass

1 year ago

ShemaleZ

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15:26 63%

ADULT TIME - Best First Date Ever! Casey Calvert Gobbles Up T-Girl Leilani Li Takes DEEP Creampie!

1 year ago

JizzBunker

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06:01

First Time Tranny Guest Anally Fucked In The House

5 years ago

BeMyHole

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06:29

Sissy crossdresser with father

2 months ago

TrannyGem

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04:29

Sexy brunette bangs her boyfriend's ass for the first time

4 years ago

AShemaleTube

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06:10

TGirl Melissa first time with latinos cock

7 years ago

AShemaleTube

first time
10:56

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2 years ago

ShemaleMovie

first time
33:17

His first time with a shemale

3 years ago

xHamster

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03:10

BOBSTGIRLS: Boom Boom - New Girl Lola Bloom

2 years ago

xHamster

cute, first time
05:55 89%

Premiere: Ashley Is Fucked By A Shemale And Swallows For The First Time Transsexual Sperm! 6 Min With Ashley Cumstar And Rosella Extrem

3 years ago

ShemaleZ

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05:27

First to Cum Challenge - Veronica Sanders

9 months ago

xHamster

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19:39

Lucimara Santos Pool teen First Time t-girl pound

7 years ago

ShemaleZ

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07:01

Teen facial compilation and brunette caught cheating first time Kayla

4 years ago

TrannyOne

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05:45

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

2 years ago

ShemaleZ

first time
06:38

Cool Trap from the club

7 months ago

ShemaleTaxi

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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
12:05 77%

Beauty Fucks For Her First Time With A Trans And Its With Spencer Bradley

2 years ago

ShemaleZ

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11:50

Torn Up for my ts gf for the very first time

2 years ago

KeekAss

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07:32

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

3 years ago

TXXX

first time
12:40

Is this your first-ever time with a brazilian shemale

7 years ago

HDSex

first time
05:07

Dude for the fist time has tranny up his arse

6 years ago

Analdin

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22:34

Fucked For The Very First Time

4 years ago

TXXX

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36:43 67%

Very first time with my Hismith machine

4 years ago

ShemaleTaxi

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05:50

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6 years ago

TXXX

first time, teen (18+)
05:00 80%

Post-Op Ladyboy Beauty Natty Fucked Bareback

2 years ago

BeMyHole

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06:46

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14 years ago

xHamster

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05:31

Sexy Thai ladyboy tries anal sex for the first time

6 years ago

ShemaleZ

first time
10:20

Claudia Clars First Time Cum

6 years ago

TXXX

first time
10:20

Fucking The Beautiful Adharas Tight Ass For The First Time

6 months ago

HClips

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30:27 82%

Skinny she-male gets insatiable anal fucked in the small ass

7 months ago

VideoSection

shemale, anal, asian, 18, ass, skinny, first time
12:10

First Time In Bed With A Transvestite

1 year ago

JizzBunker

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07:23

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

3 years ago

TXXX

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52:54 90%

Trans Vanessa Jhons welcome Gonzo first time double anal

5 years ago

TXXX

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06:01

Czech casting teen first time Analmal Training

4 years ago

TrannyOne

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06:39

Full Video : Bbc First Time With Trans Pussy

3 years ago

GetTranny

first time, ebony, interracial
10:57

MY FIRST TIME

12 years ago

AShemaleTube

first time
09:57

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

1 year ago

BeMyHole

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02:06

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4 years ago

AShemaleTube

first time
06:24

She-creature Jusmin first Time act

2 years ago

ShemaleTaxi

first time
12:46

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

4 years ago

ShemaleTaxi

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08:34

Straight First Time Explode in Sissy Mouth

8 years ago

xHamster

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05:24

Joanna Angel and shemale Aubrey Kate first time with ea

5 years ago

xHamster

first time
03:52

First time using a vibrator, I came SO much

2 years ago

xHamster

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11:54

My First Time Fucking A Woman!!

2 months ago

ShemaleZ

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06:15

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

4 years ago

xHamster

first time
05:46

Tranny Lovers Explore The Vaginal Experience First Time -spanish Subs 6 Min

1 year ago

TXXX

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07:01 64%

Shemale and arab girl first time No Money No Problem

4 years ago

TrannyOne

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12:56

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

5 months ago

ShemaleMovie

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20:31

Blonde for the first time

7 years ago

ShemaleZ

first time
09:40

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

8 years ago

JizzBunker

first time
15:58

I Will Make Your Very First Time With A transgirl Memorable

5 years ago

TrannyGem

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05:59

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

1 year ago

TXXX

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09:43

Transangels - Dominic Pacifico, Sharnell Dupree - First-Time Fantasy

5 years ago

BeMyHole

first time
10:40

First time taking the knott

4 months ago

AShemaleTube

crossdresser, first time
26:24

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

1 year ago

ShemaleTaxi

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05:39

The Toy Was Too Big For First Time

8 months ago

HClips

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06:31

This Guy Gets Fucked For The First Time By His Friend. Too Much Fun When Top Gets Penetrated For The First Time By Big Cock In Her Tight Little Ass 7 Min

2 years ago

TXXX

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05:01

Amateur homeless girl first time No Money, No Problem

4 years ago

TrannyOne

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03:06

Bobs TGirls - hard cock sex

2 months ago

PornHat

beauty, solo, feet, first time
04:04

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

3 months ago

Fuxxx

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25:49

Futanaria First Time Fuck Buddies

6 years ago

ShemaleZ

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06:09 67%

Casting Nubian TS Strokes her Fat Cock

7 years ago

TrannyGem

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14:49

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5 years ago

TrannyGem

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06:15

Small tits shemale Jade Downing analed

3 years ago

TrannyGem

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06:53

First-time Fantasy - Sharnell Dupree

3 years ago

ShemaleZ

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

3 months ago

BeMyHole

ebony, creampie, 18, ass to mouth, ass licking, cum in mouth, BBC
35:17 71%

The First Time Married To A Trans Girl

7 months ago

HClips

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13:11

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6 months ago

ShemaleMovie

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13:19

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

9 months ago

ShemaleTaxi

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08:12

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5 years ago

VideoSection

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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

ShemaleZ

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07:41

First Time For My Husband Fuck With Ladyboy

2 years ago

GetTranny

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06:10

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4 years ago

ShemaleTaxi

first time
08:28

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4 years ago

BeMyHole

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09:47 94%

MILF Stepmom Let Stepsons TS GF Fuck Her Asshole

2 months ago

BeMyHole

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05:11

RUBBERDOLL MONIQUE - As a bimbo doll at a parking lot

3 years ago

xHamster

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12:30

Is this your first time with a Brazilian shemale

7 years ago

xHamster

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20:04 93%

TGIRL POST-OP: Jenny Loves Her New Pussy Fucked

4 years ago

xHamster

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11:07 63%

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

5 years ago

HClips

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