SHEMALE • FIRST TIME 3,251 videos

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05:25

White tranny takes BBC deep in her ass for the first time

2 years ago

XXXDan

BBC, first time
01:37

White gurls first time riding BBC

6 years ago

xHamster

riding, BBC, first time
12:01

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

1 year ago

TXXX

first time
11:26

Jesscia Bloom Double Anal With Dildos First Time

2 years ago

xHamster

double anal, first time, double penetration
09:13

His First Time With A Woman With A Dick

1 year ago

ShemaleZ

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12:16

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7 years ago

xHamster

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04:36

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1 year ago

xHamster

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01:38

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1 year ago

xHamster

first time
01:18

Sissy Sucking Cock First Time on Video

3 years ago

xHamster

first time
13:36

First Time Fucking My Ass On Stream On Star Wars Day

1 year ago

ShemaleZ

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05:00

Dominic Pacifico & Sharnell Dupree in First-Time Fantasy - TransAngels

4 years ago

TXXX

small tits, first time
06:15

Pretty lady Cadence sucks a tranny cock for the first time

2 years ago

XXXDan

first time
1:01:26

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6 years ago

TXXX

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11:39

First Time Sissy Anal Fingering With Joi Dirty Talk - Cumshot On Black Stockings And Cum Play

2 years ago

ShemaleZ

dirty talk, JOI, first time
32:30

Susie Vicentini - First Time On Camera

5 years ago

ShemaleZ

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17:39

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4 years ago

xHamster

german, bisexual, teen anal (18+), 69, asshole, first time, hardcore
02:06

Crossdresser First Time Using Dildo

4 years ago

xHamster

first time
13:46

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5 years ago

xHamster

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06:31

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6 years ago

AShemaleTube

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12:00

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7 years ago

xHamster

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06:16

Ladyboy Jusmin First Time Anal

9 years ago

xHamster

teen anal (18+), first time
05:25

First-ever time for a fag biotch

3 years ago

VideoSection

first time
10:15

Redhead Shemale First Time Stroking!

3 years ago

AShemaleTube

first time
02:00

Sissy Amateurs First Porn

3 years ago

xHamster

first time
06:03

Chubby tranny masturbating in first time solo

6 years ago

XXXDan

chubby, solo, first time
14:09

POV Shemale Fucks Sweet Pussy

2 years ago

PornHub

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06:57

My first time doing anal

6 years ago

TXXX

dildo, first time
26:27

Rocco Steele And Trip Richards In First Time With A Trans Guy

2 years ago

HClips

tattoo, first time, brunette
03:03

Trans girl tries anal deep heat for first time

9 years ago

xHamster

first time
15:08

GLORIUS PUSS ATTEMPT VERY FIRST TIME GAINT TRANSGENDER PRINCESS FUCK-STICK

3 years ago

KeekAss

lesbian, first time
14:32

This is the first time in a transvestite gang bang

6 years ago

JizzBunker

first time
14:11

This is our very first time having a three way with a ladyboy

3 years ago

KeekAss

compilation, handjob compilation, first time
19:33

Sissy Bimbo Brandynette First Time Caged showing off her new Lovense toy

4 years ago

ShemaleZ

18, first time
03:16

First time Ladyboy Nickie for TransWorldAsia

10 years ago

PornHub

first time
15:48

First time with an amateur trans

4 years ago

TrannyOne

dogging, first time
13:46

This is our very first time having a 3 way with a ladyboy

3 years ago

KeekAss

handjob compilation, first time
03:51

First time crossdressing

4 years ago

HClips

first time
14:59

GLORIUS PUSSY TRY FIRST TIME GAINT SHEMALE COCK AND LOVE IT

3 years ago

AShemaleTube

first time
11:53

I want your first time with a she-creature to be extraordinaire

3 years ago

HDSex

bisexual, first time
10:11

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3 years ago

VideoSection

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15:07

GLORIUS PUSSY TRY FIRST TIME GAINT SHEMALE COCK AND LOVE IT

3 years ago

AShemaleTube

first time
02:18

Busty Angelina Castro first time trying TS cock

4 years ago

AShemaleTube

first time
06:16

Darling Leticias First Time Filmed!

8 years ago

JizzBunker

first time
06:20

TGirl Yasmim very first time with a big hard-on

4 years ago

VideoSection

first time
04:30

First time with a lady-boy

4 years ago

ShemaleZ

first time
2:31:59

Danna Valentina 20200828 very first time i catch jism

1 year ago

ShemaleTaxi

latex, caught, taxi, first time
06:52

Kinky iris with new spike clamps, very painfull first time

4 years ago

xHamster

first time
17:38

DVaBoi Femboy Sissy First Time Dildo Sesh

3 years ago

BeMyHole

first time, femboy
15:08

Suleika Spandex ravages a sissy buttfuck bi-atch (first-ever time)

2 years ago

TrannyGem

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14:21

Your first time with a hot Brazilian tranny will be amazing

4 years ago

xHamster

first time
20:45

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3 years ago

TrannyGem

cute, interracial, first time
11:07

Are you thrilled about your first-ever time with a tranny

3 years ago

HDSex

first time
17:27

Sissy uses Lube for the first Time and Absolutely Loves It!

5 years ago

TrannyGem

ass to mouth, shaving, first time
06:25 82%

Holy hell, what a super hot threesome with cougar Dee Williams. This is the very 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

2 years ago

ShemaleTaxi

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05:15

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4 years ago

PornHub

femdom, teen (18+), teen anal (18+), fisting, monster, reality, surprise
01:54

Miss Alina's First Time Sucking Cock

5 years ago

xHamster

first time
24:42

18yo Smallish Ebony TGirl Pounds DL BIG BLACK COCK for first-ever Time. He said it’s finer than cunt

2 years ago

TrannyGem

18, BBC, first time
12:11

First full video first time anal

4 years ago

HClips

first time
04:26

Str8 first time with SHemale gives of cum facial

4 years ago

PornHub

facial, first time
01:57

I don't know what to wear

3 years ago

xHamster

czech, first time
15:26

Its ultimately time to pound my first-ever transgirl

4 years ago

TrannyGem

first time
18:38

Its time you tasted your first-ever she-male dick

4 years ago

ShemaleMovie

first time
23:12

GORGEOUS BRUNETTE WITH WET PUSSY TASTE SHEMALE COCK FIRST TIME

1 year ago

xHamster

creampie, shemale and girl, big cock, wet, first time, brunette
17:32

Crossdresser sissy teaching her thight bum

2 years ago

TrannyGem

public, vibrator, first time
14:38

Glorius Pussy Try First Time Gaint Shemale Cock And Love It - Suggest Model

2 years ago

ShemaleZ

first time
06:39

Her first time in a threesome with shemale

3 years ago

AShemaleTube

threesome, first time
01:19

Transsexual Valeria Wong masturbates on camera for first time

5 years ago

AShemaleTube

first time
05:57

Her first time with a shemale

4 years ago

ShemaleZ

first time
17:43

Gothic crossdresser teenager first-ever time toying with fuck stick and jizzing all over herself

2 years ago

TrannyGem

first time
03:45

Sissy Kitty Hime does butt things first time!

4 years ago

ShemaleZ

first time
04:00

Dorm Room First Times Emma Kisses Her first Girl AND Sucks her Cock

9 years ago

TXXX

kissing, dorm, first time
13:02

Femboy Pummels Her Cunt First-Ever Time

3 years ago

KeekAss

first time, femboy
05:24

Cumming orgasm first time filmed

4 years ago

xHamster

orgasm, first time
08:02

Transgender swaps blowjob with big dick first time bisexual

4 years ago

xHamster

bisexual, first time
05:35

Hung first time Trans Amy

4 years ago

xHamster

first time
06:24

Ladyboy Jusmin first-ever Time activity

5 years ago

HDSex

handjob, facial, oil, gape, first time
11:56

This is our very first time pounding a ts honey

4 years ago

KeekAss

MILF, handjob compilation, first time
44:17 93%

Kendall Penny - Southern Sass Submits For The First Time!

1 year ago

ShemaleZ

stockings, fetish, BDSM, ass, first time, brunette
06:10

Tgirl yasmim dornelles first time with tony lees big cock

5 years ago

JizzBunker

first time
18:15 82%

FEMALE DOMINATION HANDBALLING ASSFUCKING INSTRUCTING PEGGING DOMINATRIX PREDOMINANCE FEMBOY

2 years ago

TrannyGem

femdom, train, instruction, wife, fisting, bondage, reality
13:25

Bigtits tranny First Time nail With A darksome guy

4 years ago

ShemaleZ

first time
11:42

Trans Angel Fucks Ass With Dildo First Time

5 years ago

TXXX

first time
09:45

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4 years ago

ShemaleZ

first time
07:03

First Time Boyfriend Bareback

10 years ago

xHamster

first time
23:21

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1 year ago

ShemaleTaxi

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14:04

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3 years ago

HDSex

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11:59

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3 years ago

HDSex

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03:06

Deep Throating Str8 Guy. It was his first time

4 years ago

ShemaleZ

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02:43

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6 years ago

ShemaleZ

first time
15:16

My first-ever time as a sissy was nicer than I ever imagined

2 years ago

ShemaleTaxi

first time
33:08

Theresa Si getting ready for her very first webcam flash, first time playing with the ESCA vibrator practice dirtytalk and fuck

1 year ago

ShemaleMovie

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19:20

German Sissy Ron first Vid

2 years ago

xHamster

german, JOI, first time
15:17

Crossdressing for the first time senses so liberating

1 year ago

ShemaleTaxi

lingerie, panties, first time
14:47

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4 years ago

xHamster

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16:47

Compilation of taut femboy using fuck stick for the first-ever time

1 year ago

ShemaleTaxi

taxi, first time
35:52

Cute victim she-creature Rikki first time casting call

4 years ago

ShemaleMovie

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16:39

Your very first time with a transgender princess will be extraordinaire

4 years ago

ShemaleMovie

gangbang, first time
16:59

Femboys very first Time with hefty fuck stick

1 year ago

ShemaleTaxi

first time
11:56

This is our first time fucking a babe transsexual

6 years ago

JizzBunker

bisexual, babe, first time, hardcore
14:08

Teen Cd Femboy In Secretary Outfit First Time Using Anal Vibrator Til Cumming

3 years ago

HClips

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17:12

Throbbing cock TS tranny pound latina teen girl First Time

4 years ago

ShemaleZ

first time
20:07

Skitty in My very first time with a Machine

2 years ago

KeekAss

latex, machine, first time
52:59

Trans Vanessa Jhons Welcome To Gonzo With First Time Double Anal Sz2489

3 years ago

Upornia

fetish, double anal, gangbang, first time, double penetration
16:02

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3 years ago

xHamster

couple, JOI, first time
16:08

I will make your very first time with a shemale never-to-be-forgotten

4 years ago

HDSex

first time
06:10

TBabe Lena Kellys first time with a BIG BLACK COCK

5 years ago

Analdin

chubby, blonde, asshole, first time
11:28

Me and my girls first time with a transsexual

6 years ago

JizzBunker

bride, girlfriend, first time
06:49

Crossdresser gets put in chastity for first time

6 years ago

AShemaleTube

first time, chastity
16:20

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4 years ago

HDSex

first time
15:58

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6 years ago

xHamster

first time
21:46

Guy Tries Out Shemale For The First Time, Sucks Dicks, Ass Fucks and Facial

6 years ago

PornHub

facial, first time, hardcore
17:30

Young guy gets fucked in the ass for the first time by a trans

2 days ago

JizzBunker

anal, amateur, first time, shemale, couple
06:33

The wife gave it to me as a gift for her husband! For him to eat with her for the first time

3 days ago

AShemaleTube

stockings, shemale and girl, homemade, threesome, shemale, first time
26:03

First-ever time with a Bad Dragon - Demogorgon - large firm, wild rail

4 days ago

ShemaleTaxi

anal, shemale, masturbation, first time
06:24

First Time Fembois with Thayane Beck for TrannyBizzare

Yesterday

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05:18

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Yesterday

xHamster

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05:16

Trans Guys First time with Sex Machine Huge Orgasm

Today

PornHub

first time
22:17

Massive cumshot after Jade fucks her flesh light - first time buttplug

4 years ago

ShemaleZ

first time
15:59

Amateur Shemale Nev Nomi puts her Fox Tail in for the first time!

4 years ago

ShemaleZ

first time
17:46

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3 years ago

HDSex

first time

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