TRANNY • FIRST TIME 1,216 videos

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06:03

From Shy to Slay: Crossdresser Kitty's Personal Transformation Stories!

7 months ago

xHamster

shemale, shy
05:27

Express Yourself: Crossdresser Kitty's Guide to Authenticity!

7 months ago

xHamster

first time
05:36

Confidence is Key: Embrace Your Unique Style with Crossdresser Kitty!

7 months ago

xHamster

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05:24

Fashion Forward: Styling Tips for the Modern Crossdresser!

7 months ago

xHamster

shemale
05:25

Pure Elegance Personified: Celebrating the Timeless Beauty and Grace of White Bodies in All Their Splendor

7 months ago

xHamster

first time, teen (18+)
06:06

Fabulous Femboy Frenzy: Unleash Your Inner Diva!

7 months ago

xHamster

teen (18+), femboy, beauty
05:40

Captivating Cuteness: Dance Like Nobody's Watching!

7 months ago

xHamster

cute, teen (18+)
05:38

Sashay Your Way to Stardom: Crossdresser Kitty's Journey!

7 months ago

xHamster

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06:06

Slay the Dance Floor: Crossdresser Compilation Extravaganza!

7 months ago

xHamster

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06:35

Fierce and Flawless: Crossdresser Kitty's Fashion Showcase!

7 months ago

xHamster

big cock, beauty, ladyboy
07:40

Dancing Delight: Spreading Joy through Movement

7 months ago

xHamster

threesome, wife, ladyboy
07:28

Sexy Model Secrets: Embrace Your Confidence and Style!

7 months ago

xHamster

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05:37

Fashion Forward: Tips and Tricks for Crossdressers

7 months ago

xHamster

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05:20

Makeup Magic: Transforming into a Glam Goddess

7 months ago

xHamster

threesome, wife, small cock
05:49

Glamorous and Gorgeous: Crossdresser Chronicles Unleashed

7 months ago

xHamster

teen (18+), crossdresser, big cock
03:11

TGIRLPORNSTAR: VALERIA & MIGUEL!

1 year ago

xHamster

first time
03:11

ASIANTGIRL: ENTER BASTY!

10 months ago

xHamster

thai, small tits, first time
03:11

GROOBYGIRLS: Debuting Goddess Genevieve

1 year ago

xHamster

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08:12

Hot and deep inside my ass!!!

1 year ago

xHamster

first time
06:01

All About Me: Sharing Personal Stories and Experiences

7 months ago

xHamster

shemale, first time
02:30

All to the end

1 year ago

xHamster

first time
03:11

BOBSTGIRLS: We're Thrilled to Introduce Amy

1 year ago

xHamster

dildo, first time
01:26

Como si fuera la primera ves

1 year ago

xHamster

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07:32

When I Lost My Virginity - Sex memories by Maya McAdamia

1 year ago

xHamster

first time
03:11

FEMOUT.XXX: Welcome Wiki

1 year ago

xHamster

stockings, first time, polish
03:26

Night walk at train station and parking lot with fishnet stocking

2 years ago

xHamster

public, train, first time
03:22

Wetlook in yellow top and panties in bathroom. Wetlook shower. Wet yellow underwear. Part 2

1 year ago

xHamster

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05:11

RUBBERDOLL MONIQUE - As a bimbo doll at a parking lot

2 years ago

xHamster

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02:34

Sissy CD Samara Coxxx training her pussy some more - riding a dildo

2 years ago

xHamster

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03:10

BOBSTGIRLS: Boom Boom - New Girl Lola Bloom

1 year ago

xHamster

cute, first time
06:51

Lovely Sissygasm caged clitty squirting

2 years ago

xHamster

squirt, first time, hands free
17:32

Crossdresser sissy training her thight ass

2 years ago

xHamster

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03:27

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2 years ago

xHamster

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03:25

Long legged lover

2 years ago

xHamster

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01:07

Huge Analslut

2 years ago

xHamster

mature anal, first time
02:24

Nipplesuckeer

3 years ago

xHamster

first time
48:04

Fuck machine anal, 6 Toys! With 2 limp clitty cum shots

2 years ago

xHamster

latex, mature anal, machine, first time
04:54

Sexy bitch

3 years ago

xHamster

first time
38:26

OMG – only after she pulled her pants down did he know she had a dick

3 years ago

xHamster

MILF, orgasm, nipples, natural, cum in mouth, first time
04:02

Heterflexible straight discrete I adore

2 years ago

xHamster

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13:02

Kendal Penny has anal fun in college

3 years ago

xHamster

college, first time
14:47

Hands Free Sissy-Gasm

3 years ago

xHamster

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03:21

Mall Flash In Sissy Chastity

3 years ago

xHamster

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03:57

20051021 waspie and tits

3 years ago

xHamster

first time
10:01

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3 years ago

xHamster

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01:57

I don't know what to wear

4 years ago

xHamster

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01:12

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4 years ago

xHamster

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13:02

Trans Hottie Kendall Penny Gives the Ultimate Date to Lucky

4 years ago

xHamster

first time
05:12

Hung Ximena FTTV

4 years ago

xHamster

JOI, first time
02:16

Fucking my ass so good tonight

3 years ago

xHamster

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03:44

Bigcock transgender makes a submissive man crave for her cum

4 years ago

xHamster

first time
09:33

Summertime Saga - Trans cutie taking it full anal

4 years ago

xHamster

first time
02:56

Horny on the Couch

4 years ago

xHamster

first time
08:39

Fat Sissy Goes For A Ride

4 years ago

xHamster

fat, chubby, BBW, BBC, first time
01:08

My intro

4 years ago

xHamster

first time
09:54

Asian Transgirl Daniella Teas First Time Getting Fucked By A Guy on Video

4 months ago

PornHub

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10:20

Remigio Zampa starts a girl to anal intercourse!Roby Bianchi

4 years ago

xHamster

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15:51 82%

ADULT TIME - Straight Girl Kenzie Taylor First Trans Fuck With Big Titty T-Girl Brittney Kade

3 months ago

PornHub

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20:01 92%

Pretty young tgirl ass fucked by girl for the first time

5 years ago

PornHub

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04:26

Bustle CD Riding BBC

4 years ago

xHamster

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11:57

Amanda Borges first time fucking with trans babe Marcelle Herrera

8 months ago

PornHub

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10:38 71%

A Ginger Steals Vixens Virginity !!! (FULL) !!!

2 years ago

PornHub

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20:11 85%

AMO VESTIRME DE MONJA Y TORTURAR MI CULO PARA VER MI SEMEN REGADO EN TODA LA HABITACION

2 years ago

PornHub

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24:59

Older Futa Lesbian Shemale Fucks Young First Time Virgin With Multiple Orgasms - Sims 4

7 months ago

PornHub

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14:46

AMATEUR ASIAN LADYBOY FIRST TIME ANAL TRAINING

2 years ago

PornHub

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11:36

Wife Gives Up Her Tight Asshole To Hot Shemale Making Her Scream From Being Stretch Wide Open & Cum

2 years ago

PornHub

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25:12 83%

Beautiful shemale and cute teacher Real man first time (นางใน)

3 years ago

PornHub

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06:07

Mature black tranny woman fuck young white boy first time

3 years ago

PornHub

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04:26

Str8 first time with SHemale gives of cum facial

5 years ago

PornHub

facial, first time
06:00

BLONDE SHEMALE IN RED LINGERIE TRY BIG LATINA COCK FIRST TIME

2 years ago

PornHub

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08:25 82%

TRANS GIRL GETS FUCKED BY ANOTHER TRANS GIRL FOR THE FIRST TIME

4 months ago

PornHub

big ass, shemale and girl, big tits, shemale
09:40

Teen Thug first time with Tranny

5 years ago

PornHub

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09:52

Crossdresser Jackie first time in public

3 months ago

PornHub

crossdresser, solo, public, amateur
14:18

Sissy Femboy Wets her Diaper for the First Time

3 months ago

PornHub

pissing, asian, diaper, sissy, femboy
13:55

My first webcam with Alice Blitz. We fuck each other in the ass three times. Only fucking

3 years ago

PornHub

feet, lesbian, russian, reality, first time, webcam
10:38

I want an old man to fuck me in the ass for the first time

5 months ago

PornHub

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07:17

POV: Fucking a sexy Trans girl for the first time

4 months ago

PornHub

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11:37

First Time FootJob by a Cute Trans Girl POV FOOT FETISH CUM

5 months ago

PornHub

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10:24

Trans cutie gets her pussy railed for the first time

5 months ago

PornHub

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06:18

The first time with a trans girl is unforgettable

4 months ago

PornHub

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05:16

Trans Guys First time with Sex Machine Huge Orgasm

6 months ago

PornHub

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12:30

Fems First time Deepthroating BBC - G002

6 months ago

PornHub

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08:59

First time at the Aquarium

6 months ago

PornHub

shemale
19:31

FTM tboy jerks off huge clit for the first time

6 months ago

PornHub

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06:56

Beautiful Big dick TRANS tries pussy for the first time

6 months ago

PornHub

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05:34

First time hollow plug for anal slut - gape my hole please!

8 months ago

PornHub

double anal
14:09

Femboy rides 7 inch dildo for first time

7 months ago

PornHub

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29:23

Big glass butt plug first time all the way in & first time double anal with cum eating

7 months ago

PornHub

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10:05

My First Time Anal

7 months ago

PornHub

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07:05

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6 months ago

PornHub

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02:50

Cute trans girls first time taking 9 inches, she eats cum out of a bowl

10 months ago

PornHub

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05:12

Big ass shemale tries anal beads for the first time

9 months ago

PornHub

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10:40

Petite Latina Teen TS Cums On Film for the First Time Ever!

9 months ago

PornHub

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03:50

Fucking my boyfriend for the first time, I cum on his ass

10 months ago

PornHub

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05:33

Young Trans MILF Plays With Herself for the First Time

9 months ago

PornHub

solo
10:20

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

1 year ago

PornHub

first time, missionary
01:13

That was my first time with my big dildo

10 months ago

PornHub

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10:21

Lily Star Takes fist and prolapse for very first time!

1 year ago

PornHub

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10:39

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1 year ago

PornHub

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15:29

Shemale first time with sex doll

10 months ago

PornHub

doll, first time
13:18

DILDO REVIEW: Gorgeous Filipina Trans Girl Tries a 7 Inch Electric Dildo for the First Time

2 years ago

PornHub

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05:16

Freaky BBC neighbor gets his shemale neighbor on her back for the first time

1 year ago

PornHub

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05:17

Sexy BBC fucks a sexy shemale for the first time

1 year ago

PornHub

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08:05

Rookie Tgirl Arielly Miller Tries Machine Powered Anal for the First Time

1 year ago

PornHub

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10:45

Asian Ts Hellen Yamaguchi First Time Fucked at Big Booty Tgirls

1 year ago

PornHub

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11:51

Trans Angel Fucks Ass With Dildo First Time

3 years ago

PornHub

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11:49

Amateur tranny gently toying herself at camera for the first time

2 years ago

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11:35 71%

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3 years ago

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18:34

Hung Trans Keira Verga fucks her fan for the first time

3 years ago

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11:49

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2 years ago

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06:17

Erster Transsex - brasilian ladyboy fucks first time anal in a private porn

5 years ago

PornHub

first time
01:46

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4 years ago

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06:07

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4 years ago

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06:07

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4 years ago

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26:01

First time with a Bad Dragon - Demogorgon - large firm, crazy ride

4 years ago

PornHub

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20:00

FUCKING A TRANS FOR THE FIRST TIME!

7 years ago

PornHub

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21:46

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

6 years ago

PornHub

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08:45

Stunning Shemale Ingrid Moreira fucks hard guy for his first time! Facial!

6 years ago

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05:20

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7 years ago

PornHub

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30:02

LETSDOEIT - Intense FIRST TIME Fuck with Latina TGirl Rafaella Ferrari

5 years ago

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