SHEMALE • FIRST TIME 4,063 videos

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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

outdoor, first time
12:24

Blonde shemale first time with a guy

8 years ago

ShemaleZ

first time
17:19

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

5 years ago

TrannyGem

facial, natural, first time
07:32 90%

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

2 years ago

MyLust

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06:01

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4 years ago

TrannyOne

first time, amateur
15:29

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3 years ago

ShemaleTaxi

first time
14:00

My First Time With A Trans Was Incredible

2 months ago

BeMyHole

shemale, first time
10:20

Fucking The Beautiful Adharas Tight Ass For The First Time

8 months ago

HClips

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08:44

First Time Whipped

4 years ago

ShemaleZ

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07:16

Big booty latina gets anal invaded in a wild session

5 months ago

XXXVogue

first time, amateur
08:39

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2 years ago

AShemaleTube

first time
08:06

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

3 months ago

ShemaleZ

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05:59

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5 years ago

HellPorno

69, first time
09:47 94%

MILF Stepmom Let Stepsons TS GF Fuck Her Asshole

3 months ago

BeMyHole

mom, blowjob, big ass, MILF, ladyboy, ass licking, shemale and girl
12:10

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5 years ago

ShemaleMovie

beauty, first time
02:18

First-Ever Time Rapper Porks Transgender in V-Card

2 months ago

TrannyGem

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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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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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03:01

FEMOUT GONZO: Lemmis Very First Time!

3 years ago

KeekAss

toys, first time, crossdresser
06:33

Very Small Cock Dickgirl Fucks For The First Time

2 years ago

TrannyOne

small cock, first time
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

beauty, blowjob, first time
05:57

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9 years ago

DrTuber

nurse, cuckold, 18, first time
25:36

Hellos First Time With fantastic lady-twink

7 years ago

ShemaleZ

first time
10:45

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7 years ago

xHamster

first time
07:52

Pierce Pariss Made Desire in First Bliss

2 months ago

XoZilla

missionary, heels, shemale, first time
07:41

German Crossdresser First Time in front of cam

13 years ago

AShemaleTube

amateur, german, first time
10:13 64%

Real Transgender Gal Gets Ass-Fuck Smash

2 years ago

TrannyGem

cute, homemade, teen anal (18+), british, sissy, first time
14:19

Is this really your first time with a t-girl

5 years ago

ShemaleMovie

first time
20:54

Tranny surprises male date

1 year ago

JizzBunker

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05:16

Shemale playgirl is a admirable cowgirl

1 year ago

ShemaleMovie

first time, dildo, 18
10:43 40%

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

1 year ago

ShemaleMovie

homemade, huge dildo, dildo, 18, blonde, skinny, BBC
07:12 65%

Very first Time in Public

2 months ago

ShemaleMovie

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05:10

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

6 years ago

ShemaleZ

anal, piercing, first time
38:26

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

4 years ago

ShemaleZ

POV, first time
36:43

Kendall Penny - Submits for the First Time

6 years ago

ShemaleZ

BDSM, first time
13:25

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

4 years ago

TrannyGem

teacher, first time
04:21

Crossdresser Lea First Time Fucked In All Angles

3 years ago

ShemaleZ

BDSM, crossdresser, first time
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

strapon, ass licking, domination, first time, hardcore
06:07

Ladyboy first time fucking guy

3 years ago

TrannyOne

first time
06:14

Ladyboy Jusmin First Time Anal

11 years ago

DrTuber

first time
12:40

Sexy Thai ladyboy enjoys being rigorously banged from behind in POV

1 week ago

XXXVogue

thai, POV, facial, cumshot, asshole, first time, missionary
11:39

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

9 months ago

TrannyGem

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16:11

Your first-ever time with a ladyboy will be unbelievable

5 years ago

TrannyGem

first time
11:32

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

4 years ago

TrannyGem

first time
11:17

THE first TIME YOU NEVER leave behind

7 months ago

ShemaleTaxi

teen (18+), big ass, lingerie, ladyboy, 18, ass to mouth, taxi
06:10

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

6 years ago

TrannyGem

blonde, first time
16:20

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

3 years ago

ShemaleZ

tattoo, first time
04:58

Nice transsexual first-time fucked

4 years ago

AShemaleTube

first time
07:07

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

3 months ago

ShemaleMovie

bareback, creampie, riding, first time
12:17

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

6 years ago

HDSex

first time
10:03

Your first time with a Brazilian shemale will be incredible

9 years ago

xHamster

first time
13:36

First Time Fucking My Ass On Stream On Star Wars Day

3 years ago

ShemaleZ

webcam, first time
04:56

First Time Crossdressing- New Heels!

2 years ago

ShemaleZ

crossdresser, first time
05:31 40%

Jessica Having anal fuckfest With 18 Plus Max

2 weeks ago

ShemaleTaxi

big tits, BDSM, monster, british, 18, cumshot, babe
22:07

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

1 year ago

TrannyGem

solo, british, toys, first time, machine, cosplay
14:49

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

5 years ago

TrannyGem

first time
35:17 75%

The First Time Married To A Trans Girl

8 months ago

HClips

POV, lingerie, shemale and girl, bareback, first time, brunette
05:43

First-time femboys experience multiple orgasms with sex toys

1 month ago

XXXVogue

femboy, first time
04:29

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

4 years ago

AShemaleTube

teen (18+), first time, boyfriend, shemale fucks guy, homemade
05:58

Shemale first time sex with a guy

5 years ago

BeMyHole

short hair, first time
06:10

TGirl Melissa first time with latinos cock

7 years ago

AShemaleTube

first time
10:57

MY FIRST TIME

12 years ago

AShemaleTube

first time
06:01

First Time Tranny Guest Anally Fucked In The House

5 years ago

BeMyHole

kissing, cute, 69, first time, condom
32:10

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

4 months ago

ShemaleMovie

couple, first time, homemade, spanking
08:14

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

4 months ago

XXXVogue

first time, outdoor, blowjob, vintage, orgy, cinema
22:34

Fucked For The Very First Time

4 years ago

TXXX

big tits, first time, shemale fucks guy
17:56 83%

Legacy Mess: bony transgender princess humps a guy for the first time. P2

6 months ago

ShemaleMovie

thai, couple, BDSM, big cock, domination, skinny, first time
33:17

His first time with a shemale

3 years ago

xHamster

vintage, domination, first time
05:24

Gargle Her Meatpipe - Tgirl Manstick Fellating Encouragement - Imposed Bisexous

7 months ago

TrannyGem

handjob, cute, femdom, bisexual, fetish, cuckold, shemale and girl
03:10

BOBSTGIRLS: Boom Boom - New Girl Lola Bloom

2 years ago

xHamster

cute, first time
05:39

The Toy Was Too Big For First Time

9 months ago

HClips

amateur, solo, first time
52:54 88%

Trans Vanessa Jhons welcome Gonzo first time double anal

5 years ago

TXXX

anal, big tits, BDSM, double anal, gangbang, big cock, orgy
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

big ass, first time, ebony
07:01

Teen facial compilation and brunette caught cheating first time Kayla

4 years ago

TrannyOne

cheating, facial, compilation, caught, first time
19:39

Lucimara Santos Pool teen First Time t-girl pound

7 years ago

ShemaleZ

pool, first time
05:07

Dude for the fist time has tranny up his arse

6 years ago

Analdin

swinger, party, fetish, fisting, first time
12:40

Is this your first-ever time with a brazilian shemale

7 years ago

HDSex

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

sperm, swallow, group, cum in mouth, first time, fetish
10:56

First time fellating a she-male cock

2 years ago

ShemaleMovie

first time
36:43 67%

Very first time with my Hismith machine

4 years ago

ShemaleTaxi

orgasm, machine, sissy, first time, solo, masturbation
09:48

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

6 months ago

ShemaleMovie

beauty, teen (18+), teen anal (18+), babe, old and young (18+), first time
06:38

My first time with a meaty trouser snake tgirl

10 months ago

ShemaleTaxi

shemale, shemale fucks guy, first time
11:50

Torn Up for my ts gf for the very first time

2 years ago

KeekAss

lesbian, first time
05:12

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

2 years ago

TrannyGem

first time
05:50

Teen guy sucking tranny cock first time

6 years ago

TXXX

first time, teen (18+)
08:08

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

1 year ago

xHamster

first time, huge dildo, dildo
12:05 77%

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
06:46

OH WoW..Tranny Fucks fine costa rican hoe for the first time

14 years ago

xHamster

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

7 months ago

ShemaleMovie

teen (18+), big cock, old man, first time
39:51

Thin japanese she-creatures first time on camera

2 years ago

ShemaleTaxi

japanese, ladyboy, 18, first time
10:20

Claudia Clars First Time Cum

6 years ago

TXXX

first time
05:31

Sexy Thai ladyboy tries anal sex for the first time

6 years ago

ShemaleZ

first time
07:32

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

3 years ago

TXXX

first time
06:29

Sissy crossdresser with father

3 months ago

TrannyGem

shemale, sissy, crossdresser, amateur, first time
25:49

Futanaria First Time Fuck Buddies

6 years ago

ShemaleZ

shemale, first time
03:47

First time out my cage for a week.

2 months ago

AShemaleTube

cumshot, amateur, sissy, solo, first time
06:01

Czech casting teen first time Analmal Training

4 years ago

TrannyOne

casting, teen (18+), czech, first time
06:24

She-creature Jusmin first Time act

2 years ago

ShemaleTaxi

first time
06:15

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

4 years ago

xHamster

first time
12:46

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

4 years ago

ShemaleTaxi

kissing, homemade, strapon, BBW, taxi, first time
07:01 65%

Shemale and arab girl first time No Money No Problem

4 years ago

TrannyOne

arab, money, first time, amateur, shemale and girl
08:34

Straight First Time Explode in Sissy Mouth

8 years ago

xHamster

first time
05:27

First to Cum Challenge - Veronica Sanders

11 months ago

xHamster

homemade, cumshot, interracial, first time, latina
06:38

Cool Trap from the club

8 months ago

ShemaleTaxi

shemale, shemale fucks guy, first time, teen (18+), prostitute
09:40

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

8 years ago

JizzBunker

first time
12:10

First Time In Bed With A Transvestite

1 year ago

JizzBunker

beauty, brazil, first time
05:45

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

2 years ago

ShemaleZ

first time
05:09

Amateur Black TS Chasitys First Time Huge Facial Creampie For New Transgender Queen

3 weeks ago

KeekAss

creampie, ebony, interracial, first time, black
15:18 82%

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

3 years ago

TrannyGem

german, bisexual, crossdresser, riding, nylon, slut, first time
05:24

Joanna Angel and shemale Aubrey Kate first time with ea

5 years ago

xHamster

first time
15:58

I Will Make Your Very First Time With A transgirl Memorable

5 years ago

TrannyGem

first time
09:57

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

1 year ago

BeMyHole

first time, shemale
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
1:29:53

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

2 years ago

ShemaleZ

first time
05:46

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

1 year ago

TXXX

big ass, threesome, lingerie, spanish, first time
12:56

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

7 months ago

ShemaleMovie

small cock, missionary, amateur, first time, shemale and girl, nylon
06:09 71%

Casting Nubian TS Strokes her Fat Cock

7 years ago

TrannyGem

casting, fat, shaving, first time
02:06

First time deepthroat blowjob on video

4 years ago

AShemaleTube

first time
20:31

Blonde for the first time

7 years ago

ShemaleZ

first time
26:24

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

1 year ago

ShemaleTaxi

beauty, shemale, first time

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