SHEMALE • FIRST TIME 4,508 videos

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07:16

Big booty latina gets anal invaded in a wild session

9 months ago

XXXVogue

first time, amateur
09:46 90%

LIL Young Transgirl Sissy gets RODE by wall plaything for the VERY FIRST TIME

2 years ago

TrannyGem

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08:14 60%

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3 months ago

XXXVogue

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03:06 67%

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5 months ago

PornHat

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23:23

Fucked for the First Time

4 years ago

TrannyOne

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22:54

First Time Threeway with a Black Tranny Babe

16 years ago

AShemaleTube

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05:58

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4 years ago

TrannyOne

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06:20

Watch Busty Tgirl Her First Time Sex With Emma Rose

1 year ago

GetTranny

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12:24

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8 years ago

ShemaleZ

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06:17

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1 year ago

ShemaleMovie

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02:17

Melody's first time

11 years ago

xHamster

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07:07

Redhead shemale fucks her dates ass for the first time

2 years ago

TrannyGem

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05:10

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5 days ago

HDSex

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06:02 79%

Filipino Femboy Has First Time Bareback Anal Sex On Camera

5 years ago

ShemaleZ

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11:08

MY FIRST-EVER TIME WITH GOOD-SIZED T-GIRL ROD

5 years ago

TrannyGem

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09:47

Cute Lexi Lore Gets Fucked By TS For The First Time

2 years ago

BeMyHole

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19:39 83%

Horny Danish Boy - His First Time

5 months ago

BeMyHole

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07:41

German Crossdresser First Time in front of cam

13 years ago

AShemaleTube

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05:35

Usually i fuck first but now its your time

7 years ago

ShemaleZ

first time
03:01 83%

FEMOUT GONZO: Lemmis Very First Time!

4 years ago

KeekAss

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05:09

All Natural Beauties Nico Love & Claire Gemini in First Time Trans Threesome

1 month ago

AShemaleTube

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12:40

Sexy Thai ladyboy enjoys being rigorously banged from behind in POV

4 months ago

XXXVogue

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06:26 78%

Trans Lesbians first-ever Time Together

3 years ago

ShemaleTaxi

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07:55

First Time Eating Ass

3 years ago

GetTranny

first time
05:08

Dude For The First Time Gets Shemales Cock

4 years ago

ShemaleZ

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08:12

We Met for The First Time with This Married Handsome Man and We Both Went Beyond Borders

2 years ago

xHamster

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17:11

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1 month ago

XXXVogue

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12:53 75%

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

6 months ago

TrannyGem

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04:50 80%

Inexperienced Teen Fuck My Ass For The First Time, Did He Cum Quickly?

2 years ago

BeMyHole

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27:19 44%

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

2 years ago

ShemaleZ

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07:14

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5 months ago

VideoSection

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09:39 80%

My first time with a trans. Part 3. I fuck her nice ass

2 years ago

JizzBunker

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23:23

Shemale Porn Video Fucked for the First Time

1 year ago

TrannyOne

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16:49

Her black transgirl fuck-stick is so meaty and rock hard

4 years ago

TrannyGem

JOI, first time
30:27 86%

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

1 year ago

VideoSection

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05:16

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1 year ago

ShemaleMovie

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06:25

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5 years ago

HDSex

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05:39

The Toy Was Too Big For First Time

1 year ago

HClips

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05:10

Pierce Paris and Janelle Fennec first time anal scene sex in the bedroom

6 years ago

ShemaleZ

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13:59 79%

TRANSFIXED - Whitney Wright Helps Hot Redhead Erica Cherry Explore New Pleasures On Their First Date

2 years ago

xHamster

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13:38

Rookie lad gets his fat ass banged hard for the first time by the nasty TS chick

4 years ago

TrannyOne

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04:58

Nice transsexual first-time fucked

5 years ago

AShemaleTube

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08:12

Fucking the Beautiful Adhara's Tight Ass for the First Time

1 year ago

xHamster

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32:10

First-ever-Time smacking, Plus fleshy Anal for Pup

9 months ago

ShemaleMovie

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35:17 78%

The First Time Married To A Trans Girl

1 year ago

HClips

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08:00

The First Time Of The Incredible Raphaella Ferrari

1 year ago

GetTranny

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10:03

Your first time with a Brazilian shemale will be incredible

9 years ago

xHamster

first time
15:29

Its my first time letting a shemale rail my shaft

3 years ago

ShemaleTaxi

first time
06:43

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

2 years ago

GetTranny

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06:39

Full Video : Bbc First Time With Trans Pussy

4 years ago

GetTranny

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05:59

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5 years ago

HellPorno

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25:36

Hellos First Time With fantastic lady-twink

7 years ago

ShemaleZ

first time
05:24

Gargle Her Meatpipe - Tgirl Manstick Fellating Encouragement - Imposed Bisexous

11 months ago

TrannyGem

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07:41

Kathy Young Sexy Shemale First Time with Her Daddy Playing 69 in Bed

1 year ago

$$ FapHouse

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04:41

Young Tgirl Aspen in first time anal sex

6 years ago

ShemaleZ

first time
10:20

Claudia Clars First Time Cum

7 years ago

TXXX

first time
05:57

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10 years ago

DrTuber

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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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11:32

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

4 years ago

TrannyGem

first time
56:57 40%

First Time in a White Swimsuit...i Was Humiliated by Being Given a Lot of Instructions in a Limited Distribution

1 year ago

$$ FapHouse

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22:07

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

2 years ago

TrannyGem

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36:43

Kendall Penny - Submits for the First Time

6 years ago

ShemaleZ

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03:06 71%

FEMOUT XXX - Jaede First Time Solo Masturbation Reveals

1 year ago

AShemaleTube

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10:45

Me fuckn my asian CD for first time bronx

7 years ago

xHamster

first time
05:58

Shemale first time sex with a guy

5 years ago

BeMyHole

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08:39

First time this slave suck a cock

2 years ago

AShemaleTube

first time
10:14

Real Transgender nymph Gets assfuck screw

11 months ago

ShemaleMovie

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33:17

His first time with a shemale

4 years ago

xHamster

vintage, domination, first time
07:32 91%

Futanari stepdaughter has her first anal time with her horny mommy [Hentai Uncensored]

2 years ago

MyLust

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05:46

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

2 years ago

TXXX

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04:21

Crossdresser Lea First Time Fucked In All Angles

3 years ago

ShemaleZ

BDSM, crossdresser, first time
10:13 64%

Real Transgender Gal Gets Ass-Fuck Smash

3 years ago

TrannyGem

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28:11

Perverted Couple Hires A Shemale For The First Time For A Threesome

3 months ago

ShemaleZ

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38:26

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

4 years ago

ShemaleZ

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12:10

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6 years ago

ShemaleMovie

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05:07

Dude for the fist time has tranny up his arse

7 years ago

Analdin

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03:10 67%

BOBSTGIRLS: Boom Boom - New Girl Lola Bloom

3 years ago

xHamster

cute, first time
10:57

MY FIRST TIME

13 years ago

AShemaleTube

first time
07:59

Curious Guy Tries First Time Anal With A Tranny 10 Min - Very Beautiful, Victoria Di Prada And Victoria Carvalho

5 months ago

Fuxxx

first time
12:05 71%

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

3 years ago

ShemaleZ

amateur, beauty, shemale and girl, first time
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.

2 years ago

BeMyHole

strapon, ass licking, domination, first time, hardcore
14:19

Is this really your first time with a t-girl

6 years ago

ShemaleMovie

first time
06:07

Ladyboy first time fucking guy

3 years ago

TrannyOne

first time
14:56

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

7 months ago

BeMyHole

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08:14

Curious Guy Poax Lenehan determined to Have romp with Stunnking big-titted Sunburnt Shemale at First Time in His Life

1 year ago

ShemaleTaxi

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36:43 67%

Very first time with my Hismith machine

4 years ago

ShemaleTaxi

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08:06

Guy With Fat Cock Fucks In The Ass For The First Time On Vacation

7 months ago

ShemaleZ

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05:31

Sexy Thai ladyboy tries anal sex for the first time

6 years ago

ShemaleZ

first time
13:06

Cosplay anal, prostate milking, sissygasm

2 weeks ago

XXXVogue

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06:14

He Cheated on His wifey with His Transvestite sister-in-law

1 month ago

ShemaleMovie

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04:29

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

5 years ago

AShemaleTube

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10:20

Fucking The Beautiful Adharas Tight Ass For The First Time

1 year ago

HClips

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06:01

Czech casting teen first time Analmal Training

4 years ago

TrannyOne

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04:55

Straight Guy Sucks Dick For The First Time

4 years ago

ShemaleZ

first time
05:21

First-ever time leisurely penetrated by a fuck machine - Big cock wants in my bootie - Part 1

2 months ago

VideoSection

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16:20

My First Time With A Trans And The First With Agatha Lyra

3 years ago

ShemaleZ

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06:10

TGirl Melissa first time with latinos cock

7 years ago

AShemaleTube

first time
06:14

Small bony Ladyboy Gets Excellent Head From Chubby Man Then Destroys His Ass Bareback internal cumshot

2 months ago

ShemaleMovie

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11:00

Beautiful japanese femboy Kelly in her very first xxx video

3 months ago

HDSex

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06:10

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

7 years ago

TrannyGem

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19:39

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8 years ago

ShemaleZ

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20:54

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1 year ago

JizzBunker

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20:04 91%

TGIRL POST-OP: Jenny Loves Her New Pussy Fucked

4 years ago

xHamster

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07:01 63%

Shemale and arab girl first time No Money No Problem

4 years ago

TrannyOne

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12:40

Is this your first-ever time with a brazilian shemale

7 years ago

HDSex

first time
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

first time
10:00

My first-ever time slurping out a cis lady and my buddy enjoyed sensing my ample trans-gifted beef whistle.

2 months ago

TrannyGem

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14:49

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5 years ago

TrannyGem

first time
19:54

She-male Jessica Kate, the most desired transsexual in Spain, fucks a young and first-timer stud - FAKings

9 months ago

ShemaleTaxi

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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

1 year ago

TrannyGem

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02:18

First-Ever Time Rapper Porks Transgender in V-Card

6 months ago

TrannyGem

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22:34

Fucked For The Very First Time

5 years ago

TXXX

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04:56

First Time Crossdressing- New Heels!

3 years ago

ShemaleZ

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05:00 85%

Post-Op Ladyboy Beauty Natty Fucked Bareback

2 years ago

BeMyHole

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06:15

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

5 years ago

xHamster

first time
06:09 63%

Casting Nubian TS Strokes her Fat Cock

7 years ago

TrannyGem

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07:01

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4 years ago

TrannyOne

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06:01

First Time Tranny Guest Anally Fucked In The House

5 years ago

BeMyHole

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06:46

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14 years ago

xHamster

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