SHEMALE • FIRST TIME 4,626 videos

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12:54

Ladyboystar - Its an - I screw you, you plow me - kind of deal!

1 month ago

TrannyGem

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08:28

Ingrid moreira fucks hard guy in his first time!

5 years ago

BeMyHole

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14:49

I want to film my very first time with a she-male

6 years ago

TrannyGem

first time
22:34

Fucked For The Very First Time

5 years ago

TXXX

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06:46

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14 years ago

xHamster

first time
06:09 64%

Casting Nubian TS Strokes her Fat Cock

7 years ago

TrannyGem

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10:20

Fucking The Beautiful Adharas Tight Ass For The First Time

1 year ago

HClips

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05:50

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7 years ago

TXXX

first time, teen (18+)
07:59

Ubug-013 I Found An Exceptionally Beautiful Cross-dressing Boy Who Ejaculates 15 Times In His First Anal Debut

3 weeks ago

GetTranny

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19:54

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

11 months ago

ShemaleTaxi

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08:34

Straight First Time Explode in Sissy Mouth

9 years ago

xHamster

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03:52

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2 years ago

xHamster

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09:44 94%

Futanari doe visits Fira for a wild breeding lesson in Centaur Things

8 months ago

XXXVogue

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06:01

First Time Tranny Guest Anally Fucked In The House

5 years ago

BeMyHole

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04:56

First Time Crossdressing- New Heels!

3 years ago

ShemaleZ

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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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16:11

Your first-ever time with a ladyboy will be unbelievable

6 years ago

TrannyGem

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
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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18:05

Bunnie Hughes Gets Her Face Frosted For Her First Scene Ever

4 months ago

HogTV

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14:56

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

8 months ago

BeMyHole

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02:18

First-Ever Time Rapper Porks Transgender in V-Card

8 months ago

TrannyGem

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25:49

Futanaria First Time Fuck Buddies

6 years ago

ShemaleZ

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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
12:46

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

4 years ago

ShemaleTaxi

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05:29

Elegant transsexual gets fucked by a guy for the first time

12 years ago

AShemaleTube

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09:40

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

8 years ago

JizzBunker

first time
15:18 83%

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

4 years ago

TrannyGem

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11:50

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2 years ago

KeekAss

lesbian, first time
20:31

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8 years ago

ShemaleZ

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07:52

Pierce Pariss Made Desire in First Bliss

7 months ago

XoZilla

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05:21

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

3 months ago

VideoSection

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52:54 88%

Trans Vanessa Jhons welcome Gonzo first time double anal

5 years ago

TXXX

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14:00

My First Time With A Trans Was Incredible

7 months ago

BeMyHole

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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

3 years ago

TXXX

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11:00

Beautiful japanese femboy Kelly in her very first xxx video

4 months ago

HDSex

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06:24

She-creature Jusmin first Time act

2 years ago

ShemaleTaxi

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15:58

I Will Make Your Very First Time With A transgirl Memorable

6 years ago

TrannyGem

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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

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10:56

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2 years ago

ShemaleMovie

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09:16

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

2 years ago

BeMyHole

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10:00

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

4 months ago

TrannyGem

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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
11:07 63%

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

6 years ago

HClips

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12:30

Is this your first time with a Brazilian shemale

7 years ago

xHamster

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10:15 71%

Free-for-all Dorian Drake gets barebacked for the first-ever time by gigantic shaft from trans female

6 months ago

KeekAss

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16:29

Your first time with a tranny will be incredible

8 years ago

xHamster

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06:34

My First Time in Tights: Embracing My Crossdressing Journey!

2 years ago

xHamster

first time
07:07

She puts it back inwards her Asspussy cuz loves it wet - Onlyfans Veronica Sanders

9 months ago

ShemaleMovie

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06:14 50%

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

3 months ago

ShemaleMovie

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05:08

Guy fucks shemale, faphouse, teenager

1 month ago

XXXVogue

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06:18

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1 month ago

XXXVogue

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08:12

Transgender interchanges blowjob with big fuckpole first time bisexous

6 years ago

VideoSection

bisexual, first time
15:26 67%

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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22:37

TRANNY SHEMALE FUCKS STRAIGHT GUY - FIRST TIME TRANSSEXUAL FUCKING

3 years ago

xHamster

latina, first time, shemale fucks guy
07:32

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

3 years ago

TXXX

first time
09:12

HIS FIRST TIME WITH A WOMAN WITH A DICK

3 years ago

xHamster

first time
04:20 74%

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

7 years ago

TXXX

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04:26

First time for chubby crossdresser

4 years ago

TrannyOne

first time
06:53

First-time Fantasy - Sharnell Dupree

4 years ago

ShemaleZ

first time
06:57

My first time doing anal

8 years ago

ShemaleZ

teen anal (18+), first time
09:57

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

1 year ago

BeMyHole

first time, shemale
05:00 87%

Post-Op Ladyboy Beauty Natty Fucked Bareback

2 years ago

BeMyHole

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10:41

Sister in law, it should be you who gargles my penis, not me

4 months ago

TrannyGem

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08:08

My first time to try 15 inch King Cock with high speed fucking machine

1 year ago

xHamster

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07:41

First Time For My Husband Fuck With Ladyboy

3 years ago

GetTranny

teen anal (18+), husband, first time, teen (18+)
05:33

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5 years ago

VideoSection

beauty, first time
06:37

First Day in Sissy Academy embarks With personal Trainer Brooke

3 weeks ago

ShemaleTaxi

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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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13:36

First Time Fucking My Ass On Stream On Star Wars Day

3 years ago

ShemaleZ

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05:24

Joanna Angel and shemale Aubrey Kate first time with ea

5 years ago

xHamster

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05:45

Lena Moon - His First Time With A Tranny

3 years ago

ShemaleZ

first time
08:44

First Time Whipped

5 years ago

ShemaleZ

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03:08

Virgin Ass First Time Dildo It!

2 years ago

TXXX

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28:11

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

5 months ago

ShemaleZ

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05:27

First to Cum Challenge - Veronica Sanders

1 year ago

xHamster

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23:54

Xhamster.com 7786211 her first-ever time with a she-male 480p

6 years ago

VideoSection

first time
10:57 73%

LEGACY MESS : Filipino Slut With ginormous Cock for the first time in pornography messy Fucks deep hard in the Throat and Ass of her Partner

11 months ago

ShemaleMovie

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26:24

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

2 years ago

ShemaleTaxi

beauty, shemale, first time
12:56

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

1 year ago

ShemaleMovie

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20:11

Femboy Ben Tennyson Big Load Cumshot after First Time Pumping her Dick with Vacuum Milking Machine

3 weeks ago

AShemaleTube

femboy, crossdresser, cumshot, first time
06:14

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

3 months ago

ShemaleMovie

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06:38

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

7 years ago

HClips

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02:06

First time deepthroat blowjob on video

5 years ago

AShemaleTube

first time
07:06

Fantastic immense pipe TRANS tries pussy for the first time

1 year ago

ShemaleMovie

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09:48

Fucking the virgin donk of an legal yr old boy for the first time

11 months ago

ShemaleMovie

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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
07:00

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

8 years ago

IcePorn

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05:45

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

3 years ago

ShemaleZ

first time
05:32

Ladyboy Jusmin Fucked Bareback

2 years ago

BeMyHole

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16:30

Guy having his first time with Geneva and Gina Ryder

7 years ago

AShemaleTube

18, 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

1 year ago

ShemaleMovie

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06:38

Cool Trap from the club

1 year ago

ShemaleTaxi

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05:10

Mischievous teenager t-girl is happy to worship another huge man-meat

1 month ago

HDSex

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12:01

TRANSFIXED - CIS And Trans Mermaids Explore New Bodies In First Time Fuck! Jewelz Blu And Kasei Kei

3 years ago

TXXX

first time
05:01

Amateur homeless girl first time No Money, No Problem

4 years ago

TrannyOne

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06:29

Sissy crossdresser with father

9 months ago

TrannyGem

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13:11

My first time being filmed! Solo playtime taunt

1 year ago

ShemaleMovie

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13:06

Cosplay anal, prostate milking, sissygasm

1 month ago

XXXVogue

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4:12:46 71%

Oots-015 Sensitive Cosplayer Who Gets Her Anus Penetrated And Writhes In Agony. Anal Masturbation, Deep Throat, Sensitive, First Time Filming, Female Orgasm, Ahegao, Lesbian, Anal Sex, Lotion Play, Pov, Doujinshi, Cosplay, Cosplayer, Big Cock, 3p, Fa

1 year ago

ShemaleZ

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13:19

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

1 year ago

ShemaleTaxi

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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

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10:08 70%

First Time Revealing My Face. College Girl Beauty in Black Pantyhose Got so Naughty When She Tried Her New Costume and Anal Plug

5 months ago

$$ FapHouse

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07:23 40%

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

4 years ago

TXXX

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1:29:53

741m584-g02 My Son Who Came Back For The First Time In

3 years ago

ShemaleZ

first time
22:39

Young Guy Fucks Blonde Latin Shemale Anal for the First Time

7 months ago

AShemaleTube

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19:27

Gonzo User plows the very first time a trans

4 years ago

ShemaleMovie

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05:17

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

2 years ago

xHamster

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12:47 83%

Ladyboystar - Changing sex positions while buttfuck drilling a mind-blowing ladyboy

1 week ago

ShemaleTaxi

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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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36:47

Kendall Cent - Submits For The First-Ever Time

6 years ago

TrannyGem

first time
06:29

First Time Fembois with Thayane Beck for TrannyBizzare

2 years ago

xHamster

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03:02

Sucking Off Str8 Guy. Its his first time

7 years ago

TXXX

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04:04

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

10 months ago

Fuxxx

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02:10

First Time Rapper Fucks Trans Woman in Chastity

3 years ago

xHamster

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05:22

Hot Asian Trans Ys first time with huge

5 years ago

AShemaleTube

first time
05:43

First-time femboys experience multiple orgasms with sex toys

6 months ago

XXXVogue

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13:38

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

2 years ago

BeMyHole

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07:12 63%

Very first Time in Public

7 months ago

ShemaleMovie

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