SHEMALE • FIRST TIME 4,187 videos

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15:28 60%

Kenzie Taylor First Time With T-Girl Brittney Kade!

8 months ago

BeMyHole

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15:58

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3 years ago

xHamster

JOI, first time
16:30 76%

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1 month ago

PornHat

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23:54

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5 years ago

VideoSection

first time
32:30

Susie Vicentini - First Time On Camera

7 years ago

ShemaleZ

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06:02

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3 years ago

TrannyGem

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22:38

Tranny Shemale Fucks Straight Guy - First Time Transsexual Fucking

3 years ago

ShemaleZ

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2:28:19 50%

Auks-100 Shemale Lesbian Series Transwoman Virgin Fucks A Big-breasted Baby-faced Babe For The First Time - Masuda Yume, Yume Masuda And Horse Hung

9 months ago

ShemaleZ

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06:16

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8 years ago

AShemaleTube

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06:10

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1 year ago

XXXVogue

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14:10

TRANS TABOO - #Cacau Di Paula #Richard rock hard - first-ever Time With A Tranny And He likes Every Minute

1 year ago

ShemaleTaxi

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10:10

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3 years ago

ShemaleTaxi

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05:46

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2 years ago

ShemaleZ

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12:13

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2 years ago

Upornia

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09:14

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7 months ago

XXXVogue

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06:01

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4 years ago

TrannyOne

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07:10

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7 months ago

ShemaleMovie

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14:56

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

4 months ago

BeMyHole

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03:43

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11 years ago

AShemaleTube

first time
23:07 40%

First Time Shemale Sex Virgins

16 years ago

AShemaleTube

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17:53

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2 years ago

ShemaleMovie

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06:55

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2 years ago

KeekAss

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08:01

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4 years ago

TrannyOne

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07:23

Lesioni di musica, Maya and Luca point of view venture with Trans Kendall. full video on my OF Page.

4 months ago

ShemaleMovie

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06:51

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4 years ago

xHamster

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11:09

Shy lady-man Shows Her penis First Time

7 years ago

ShemaleZ

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17:21 80%

I Fuck A Tranny Girl For The First Time 4k

3 years ago

ShemaleZ

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08:45

Masked guy gets dominated by the kinky TS chick

5 years ago

BeMyHole

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06:02

Filipino femboy has first-ever time without a condom assfuck orgy on camera

5 years ago

TrannyGem

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39:11 79%

A nosey woman tries a shemales spunk-pump for the very first time

3 years ago

ShemaleTaxi

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25:17 71%

Vivien Valero First Time shelady Strokers ladyboy

6 years ago

ShemaleZ

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12:05

Cute Tgirl Tires a Magic Wand for the first Time / Hitachi

7 years ago

TrannyGem

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03:27

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4 years ago

TrannyGem

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10:30

KIRITO PLAYS WITH SLIT AND BACKSIDE IN GGO (SWORD ART ONLINE COSTUME PLAY) - TAYLOR RYDE

2 years ago

TrannyGem

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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

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05:09

First Time Hollow Plug For Anal Slut - Gape My Hole Please!

1 year ago

Upornia

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06:15

Asian Kimmy First Time Fucked By A Trans

2 years ago

ShemaleZ

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06:07

Nervous About My First Time Fucking A Thai Street Trans At Trannybizzare

8 months ago

ShemaleZ

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10:36

My first threesome!!!

2 years ago

XXXDan

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10:25 58%

MARRIED COUPLE TASTE FIRST TIME THREESOME WITH GIANT SHEMALE COCK

3 years ago

xHamster

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09:52

Suzie Slut Giving It To A Trans For The First Time

4 months ago

BeMyHole

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05:58

TGirl Sarah Oliveira first time banging some dudes ass

5 years ago

BeMyHole

first time
18:14 73%

Pure TABOO asian cherry Lulu Chu Gets ALIEN DICK DRAINED By Stepmom Penny Barber & Dr. Sophia Locke!

4 months ago

ShemaleMovie

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21:03

Girl cums in her dress

1 year ago

XXXDan

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44:37

First time having sex with a trans woman Linda

1 year ago

XXXVogue

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22:49

My First Time!

2 years ago

Upornia

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23:12

GORGEOUS BRUNETTE WITH WET PUSSY TASTE SHEMALE COCK FIRST TIME

3 years ago

xHamster

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10:55 69%

His very first Time Coming to the Gullet Supermarket

6 years ago

TrannyGem

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15:12

This is my first time as a crossdressing sissy

3 years ago

ShemaleTaxi

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11:40

Your first time should be with a Brazilian shemale

5 years ago

BeMyHole

first time
14:27

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2 years ago

ShemaleTaxi

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06:15

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5 months ago

ShemaleTaxi

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03:34

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4 years ago

KeekAss

mature, nurse, pump, first time
04:04 77%

Anal Fisting First Time

4 years ago

ShemaleZ

teen (18+), teen anal (18+), fisting, first time
06:33

Ladyboy for first time sex - KimCock

7 years ago

ShemaleZ

first time
05:18

Chap smaches shemales bootie

1 year ago

ShemaleMovie

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12:00

Sissy FIRST TIME ANAL fingering and cumshot on black socks

4 years ago

xHamster

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08:10 67%

Milf plumbs teen with wire on very first time Risky Birthday Capers

5 months ago

ShemaleTaxi

teen (18+), MILF, first time
08:00 58%

Dass-133 First Time Nh Lesbian Sex. Kanami Kashiwagi Yu

2 years ago

GetTranny

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12:49

She Made Me First Time Fucking Britney From Tantaly - Cum Twice And Emily Adaire

2 years ago

ShemaleZ

first time
15:41

First Time Sex with Strong Man

8 months ago

JizzBunker

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04:42

Eevees First Time Sucking Cock

3 years ago

Upornia

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02:04

Shemale cums first time with lovense

1 year ago

AShemaleTube

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07:32

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1 year ago

ShemaleMovie

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12:46

Tried the Strawberry Condom for the First Time

5 months ago

$$ FapHouse

shemale fucks guy, cum in mouth, first time
05:42

Big Dick Shemale Compilation first Time Hot Lesbians having Fuck fest at

6 years ago

HClips

lesbian, first time
06:31

First time with a Shemale MILF

8 years ago

AShemaleTube

MILF, vintage, first time
05:45

Tries Handling A Real Cock For The First Time With Marilyn Johnson And Claire Tenebrarum

4 years ago

Upornia

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04:30

Fisting for the first time

2 years ago

XXXDan

fisting, first time
25:10

Transsexual Ingrid girl pegs her enslaved for the first time.

4 months ago

ShemaleMovie

POV, teen anal (18+), BDSM, facial, pegging, first time, hardcore
14:00

TRANS TABOO - #Cacau Di Paula #Richard Rock-Hard - Very First Time With A She-Creature And He Likes Every Min

4 years ago

TrannyGem

first time
1:38:41

My Very First Time With A Trans (Total clothespins)

5 years ago

TrannyGem

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05:17

Trannys wazoo gets stuffed

1 year ago

ShemaleMovie

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16:39

Female dom transsexual Initiation: first Time Fuckers

5 years ago

ShemaleTaxi

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06:28

Michael Sucks Marissa Minxs Dick For The First Time Before He Drills Her Ass

2 years ago

GetTranny

first time
10:51

Stepbrother, I want to do my first anal invasion

1 year ago

HDSex

first time, cum in mouth
04:17

トロトロあなるに仕上がりました　ご覧ください

2 years ago

TrannyGem

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09:13

21yrs guy extreme getting off video first time ��

5 months ago

ShemaleMovie

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27:40

Spectacular latin redhead gets her first bisexual tranny penetrate

2 years ago

ShemaleTaxi

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05:17

Pretty transsexual is not against some strong culo penetrating

10 months ago

ShemaleMovie

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07:53

Very First Time

4 years ago

AShemaleTube

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20:45

First Time ass Penetration For t-girl Adria

7 years ago

ShemaleZ

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10:51

My STEPSISTER asks me to do ass-fuck for the first-ever TIME

2 years ago

ShemaleTaxi

first time
07:11

Fernandinha Fernandez - First Time With A Tranny (shemale) And We Enjoy Tasty Cock

5 years ago

HClips

first time
02:31

Her first time with a TS

10 years ago

xHamster

first time
27:30

Beautiful brazilian redhead gets her first bisexuel tranny fuck

4 years ago

xHamster

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06:06

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6 years ago

TrannyGem

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08:15

Slim trans teen Fany Menezes experiments with the machine for her first time

8 months ago

XXXVogue

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08:26

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6 years ago

AShemaleTube

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09:40

Fucking The Virgin Ass Of An 18 Year Old Boy For The First Time

2 years ago

ShemaleZ

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05:52

Trans Tori Easton Fucks Her Online Date So Hard

1 year ago

BeMyHole

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05:13

Plus-size t-girl Pinky Doggystyles Giant Dildo for very first Time

2 years ago

ShemaleMovie

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18:24

Sissy female used her bootie first-ever time

2 years ago

TrannyGem

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06:30

Tranny Cop First Time Latina Deepthroats On The Border 7 Min

4 years ago

Upornia

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09:16

(Part 1) first Time tasting My Own jizm And Drinking Piss, Cum On Food Fetish, Asian Transgender Trap Shemale

2 years ago

ShemaleTaxi

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55:15 65%

M584G01 stepson who has returned for the first time in 5 years is a transcendental transsexual?

2 years ago

xHamster

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19:12 83%

CD TRANSSEXUAL FIRST-EVER BIG BLACK COCK !! HE CAME INWARDS of Me TWO TIMES!!! WARM PUBLIC SISSY

4 years ago

TrannyGem

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13:11

My first-ever time being filmed! Solo playtime taunt

11 months ago

TrannyGem

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08:01

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4 years ago

TrannyOne

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07:34 71%

My very first Time in Winston-Salem, NC (TRANSSEXUAL PublicPrincess)

5 years ago

TrannyGem

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02:18

Pegging Assfucking Sissy Bi-Atch Tgirl From Behind

3 years ago

TrannyGem

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10:26

Bold inked transgender beauty Chelsea Marie takes it in the ass for the first time

7 months ago

XXXVogue

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02:37

Skylar and Breds First Time Preview

7 years ago

xHamster

first time
03:53

Slamming 95mm Crimson giant faux-cock for first-ever time

3 years ago

KeekAss

first time
16:00

Guy having his first time with Geneva and Gina Ryder

6 years ago

ShemaleZ

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18:28

Its time you tasted your very first transgirl trouser snake

5 years ago

TrannyGem

first time
05:01

Sissy Takes Cocks In Both Holes For The First Time And Licks Cum Off The Floor

2 years ago

ShemaleZ

first time
12:20

I persuade a sumptuous gal with yummy udders to ravage with me and the I realize that she is a transgend

1 year ago

TrannyGem

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08:06 67%

My First Time Have Sex With Black American Man

11 months ago

ShemaleZ

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03:42 67%

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7 months ago

TrannyGem

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05:58 67%

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4 years ago

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20:15

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6 years ago

ShemaleZ

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04:54

Kaite Sisy tries her fucking machine for the first time

6 years ago

ShemaleZ

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03:27

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4 years ago

xHamster

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08:06

Guy Fucks Ladyboy In The Ass For The First Time In A Swinger Club

8 months ago

ShemaleZ

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08:22

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1 year ago

ShemaleTaxi

first time
03:50

Tattooed Guy Enjoys His Very First Time Of Trans Transaction

2 years ago

GetTranny

first time
03:41

His very first time with a trans, I think he got addicted to my gullet and my arse

1 year ago

TrannyGem

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03:00

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2 years ago

AShemaleTube

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41:14

Big Tit Latina Anna Fucks Stranger in the Ass for the First Time and Squirts

7 months ago

$$ FapHouse

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