SHEMALE • FIRST TIME 516 videos

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21:02

Platinum-blonde tranny IN crimson LINGERIE TRY BIG LATINA COCK FIRST TIME

1 year ago

ShemaleTaxi

latina, domination, first time
20:12

AMO VESTIRME DE MONJA Y TORTURAR MI BUM PARA VER MI MAN-LAVA REGADO EN TODA LA HABITACION

2 years ago

TrannyGem

nun, dress, first time
26:01

First-Ever time with a Bad Dragon - Demogorgon - phat rock hard, kinky rail

2 years ago

TrannyGem

russian, gape, first time
16:02

Acquire Prepped For Your Very First Time With A ladyboy

3 years ago

TrannyGem

first time
15:57

RUSSIAN FEMBOY drills WITH MISTRESS FOR THE FIRST TIME WITH A HUGE STRAPON, roped WITH A innocence

1 year ago

ShemaleTaxi

femdom, strapon, russian, taxi, first time, femboy
18:15

FEMALE DOMINATION HANDBALLING ASS FUCKING INSTRUCTING PEGGING DOMINATRIX SUPREMACY FEMBOY

2 years ago

TrannyGem

femdom, train, instruction, wife, fisting, dildo, pegging
33:20

First-time Dap For Phat Ass Trans Alves Ak001 - Goddess Julia And Julia Alves

10 months ago

ShemaleZ

double anal, first time, double penetration
17:43

Nubile tranny first-ever Time Sex

3 years ago

ShemaleMovie

first time
15:16

My first time being a sissy was so satisfying

1 year ago

ShemaleTaxi

crossdresser, first time
23:07

First Time sheboy Sex Virgins

6 years ago

ShemaleZ

first time
1:01:26

Pretty trans girl new toy first time anal play on cam

6 years ago

TXXX

dildo, first time
32:30

Susie Vicentini - First Time On Camera

5 years ago

ShemaleZ

tattoo, ass licking, first time
17:39

Huge Cock TS Shemale Fuck Latina Teen Girl First Time

4 years ago

xHamster

german, bisexual, teen anal (18+), 69, asshole, first time, hardcore
15:10 50%

Thai girl taste big shemale cock first time

1 year ago

xHamster

thai, first time
26:27

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

2 years ago

HClips

tattoo, first time, brunette
15:08

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

3 years ago

KeekAss

lesbian, first time
19:33

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

4 years ago

ShemaleZ

18, first time
15:48

First time with an amateur trans

4 years ago

TrannyOne

dogging, first time
15:07

GLORIUS PUSSY TRY FIRST TIME GAINT SHEMALE COCK AND LOVE IT

3 years ago

AShemaleTube

first time
16:00

Guy having his first time with Geneva and Gina Ryder

5 years ago

ShemaleZ

vintage, first time
2:31:59

Danna Valentina 20200828 very first time i catch jism

1 year ago

ShemaleTaxi

latex, caught, taxi, first time
15:56

RUSSIAN FEMBOY HUMPS WITH DOMME FOR THE FIRST-EVER TIME WITH A IMMENSE BELT DICK, STRAPPED WITH A INNOCENCE

2 years ago

TrannyGem

femdom, strapon, russian, pegging, first time, chastity, femboy
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

spandex, dutch, first time
20:45

First-Ever Time donk Foray For t-female Adria

3 years ago

TrannyGem

cute, interracial, first time
30:21

Sequel to Pegging of Sissy tart for the first Time

1 year ago

ShemaleTaxi

massage, bathroom, pegging, taxi, first time
19:31

My First Time Double-Anal And Footjob In New Lingerie

4 years ago

TXXX

teen anal (18+), footjob, double anal, first time, double penetration
17:27

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

5 years ago

TrannyGem

ass to mouth, shaving, first time
23:44

Her first time with a shemale

6 years ago

TXXX

first time
15:08

GLORIUS LABIA ATTEMPT VERY FIRST TIME GAINT T-GIRL DICK AND ENJOY IT

3 years ago

KeekAss

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
15:18

GLORIUS labia try very first TIME GAINT SHEMALE COCK

10 months ago

ShemaleMovie

first time
16:26

Huge shemale, ass fucking, first time shemale

3 years ago

HDSex

first time
25:05

Pumped Anal Prolapse! First Time Huge Butt Plug Fitted!! - Male Escort - Book Me On

1 year ago

ShemaleZ

solo, pump, first time, escort
17:06

My Taut Good-Sized Trap Bum vs Mr Hankey Dominic Pacifico BIG BLACK COCK Fake Penis

1 year ago

TrannyGem

huge dildo, dildo, penis, first time
15:26

Its ultimately time to pound my first-ever transgirl

5 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
15:08

CindiCsissy eating my own cum for the first time

1 year ago

xHamster

redhead, small tits, first time
17:17

Trans gal fills thick fuck stick in culo. First-Ever time on camera. (Utter Uncircumcised)

1 year ago

TrannyGem

huge dildo, first time
17:32

Crossdresser sissy teaching her thight bum

2 years ago

TrannyGem

public, vibrator, 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
23:21

Stellar dark-haired WITH WET PUSSY TASTE SHEMALE COCK first TIME

1 year ago

ShemaleTaxi

cuckold, wet, taxi, 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
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

2 years ago

ShemaleMovie

flashing, vibrator, first time
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
20:46

First time sucking and fucking … $$$

2 years ago

AShemaleTube

first time
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

casting, cute, first time, hardcore
16:43

Femboy Uses dildo For The first-ever Time (reupload)

2 years ago

ShemaleTaxi

first time
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
16:20

Is this your first time plowing a red-hot she-male

2 years ago

ShemaleTaxi

bisexual, first time, hardcore
18:22

First-Ever time ever! Youngster Femboy very first sesh ass-fuck teaching with Knotted Mutt Fuck Stick Part 1!

1 year ago

KeekAss

first time
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

Get ready for your first time with a tranny

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
19:09

Lucimara Santos Pool teen First Time t-girl pound

4 years ago

ShemaleZ

brazil, pool, first time
23:46

Her First Time With A shemale

6 years ago

ShemaleZ

first time
16:20

Your first-ever time with a she-creature will be amazing

4 years ago

HDSex

first time
15:58

I will make your first time with a shemale unforgettable

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
19:55

Thai Ladyboy

2 days ago

JizzBunker

couple, asian, shemale, thai, first time
19:31

FTM tboy jerks off huge clit for the first time

Yesterday

PornHub

teen (18+), solo, 18
15:52

Blonde T-Girl gets bareback BBC for the first time

Today

AShemaleTube

interracial, amateur, BBC
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

Fuckin very first time!

3 years ago

HDSex

first time
16:20

Is this your first time penetrating a steamy t-girl

4 years ago

HDSex

bisexual, first time, hardcore
19:39

Lucimara Santos Pool teen First Time t-girl pound

5 years ago

ShemaleZ

pool, first time
24:47

I m a crossdresser for the first time part 3

4 years ago

AShemaleTube

first time
27:30

Beautiful brazilian redhead gets her first bisexuel tranny fuck

2 years ago

xHamster

bisexual, MILF, redhead, dogging, first time
15:08

Cindicsissy Eating My Own Cum For The First Time

1 year ago

ShemaleZ

first time
18:33

Femboi On Cam For First Time 19 Min

2 years ago

ShemaleZ

first time
15:09

My very first time as a sissy was so liberating

1 year ago

ShemaleTaxi

panties, first time
28:23

Trans Girl Fucks A Space Unicorn Cock For The First Time!

1 year ago

ShemaleZ

first time
32:58

Theresa Si getting prepped for her first-ever camshow, very first time toying with the ESCA wand experience dirtytalk and smash

2 years ago

KeekAss

first time
19:18

Nerdy Glasses - Enby Fisting Their Ass For First Time. My Asshole Is Still Too Tight. Cum Many Times

1 year ago

ShemaleZ

fisting, tattoo, glasses, tight, asshole, first time
25:08

Anal invasion Bumper very first Time

2 years ago

ShemaleMovie

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
15:15

Small Tits ladyboy Leticia Keren Gets Machine drilled for The first-ever Time

1 year ago

ShemaleTaxi

machine, taxi, first time
23:43

First Time Double Penetration After 25 Days Without Touching Myself. I Cant Get Enough! Stoner Fav

1 year ago

ShemaleZ

fetish, first time, double penetration
36:34

First Time With My Hismith Machine

2 years ago

ShemaleZ

redhead, machine, first time
20:53

BLONDE SHEMALE IN RED LINGERIE TRY BIG LATINA COCK FIRST TIME

1 year ago

xHamster

latina, first time
17:43

Gothic crossdresser teenage first-ever time toying with faux-cock and nutting all over herself

2 years ago

KeekAss

first time
18:51

My first time cross dressing

2 years ago

ShemaleTaxi

crossdresser, dress, first time
15:18

GLORIUS vag attempt first TIME GAINT SHEMALE COCK

2 years ago

ShemaleTaxi

first time
15:16

My very first time being a sissy was so satisfying

1 year ago

ShemaleTaxi

panties, taxi, first time
25:54

First Time Blackcock

1 year ago

HClips

interracial, tattoo, first time
18:07

DVaBoi Femboy Sissy first Time fake penis Sesh

2 years ago

ShemaleTaxi

penis, first time
20:11 83%

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

2 years ago

PornHub

public, cumshot, nun, reality, dress, first time
16:19

First time with a hot shemale

2 years ago

TrannyOne

first time
16:29

Your first time as a sissy will be amazing

2 years ago

TrannyOne

first time
39:01

A curious woman tries a shemale's cock for the first time

2 years ago

xHamster

shemale and girl, first time
17:49

Huge Cock ts she-creature poke Latina Teen Girl First Time

3 years ago

ShemaleTaxi

teen anal (18+), first time
1:40:20

My first time with a tranny (Full HD Version - Director

1 year ago

xHamster

orgasm, full movie, first time, story
20:57

Gaping My Tight Hole With An Xl Dildo For The First Time, Broke My Mind And My Ass 21 Min

1 year ago

Upornia

dildo, tight, gape, first time
16:20

Is this your first time banging a super-steamy transgender princess

4 years ago

ShemaleMovie

first time
22:35

FTM Transman // Ethan hawk gets gam trembling~FIRST TIME BIG BLACK COCK!~interracial trans massive arse! humungous sausage!

1 year ago

KeekAss

black, first time, FTM
28:48

Trans gal screws a space unicorn manhood for the first time!

1 year ago

ShemaleTaxi

small cock, taxi, first time
18:05

DVaBoi Femboy Sissy very first Time fuck stick Sesh

3 years ago

ShemaleTaxi

first time, femboy
24:14

Marina s 1st Almere Visit

4 months ago

XXXDan

mature anal, fisting, first time
36:34

First time with my Hismith machine

2 years ago

TrannyOne

machine, first time
16:04

Sissy Supergirl First Time With Dildo

4 months ago

xHamster

kissing, first time
15:08

My First Time With Big Tranny One-eyed Snake

4 months ago

ShemaleZ

first time
33:12

Joanie-my first video-part 1

3 months ago

XXXDan

first time
15:06

Smallish Fun Bags Transgender Princess Leticia Keren Gets Machine Nailed for The First-Ever Time

6 months ago

KeekAss

first time
16:24

We found a hot shemale for a threesome

4 months ago

XXXDan

first time
23:03

First time Sissy MixyXXX training FIST with hands free orgasm!

5 months ago

AShemaleTube

pantyhose, orgasm, fisting, first time, hands free
37:05

Young boy fucks a transsexual for the first time

4 months ago

JizzBunker

first time
30:08

Trans woman plays with an eighteen cm Dildo for the first time, Moans from pain but ends up luving it Succubo16

6 months ago

ShemaleTaxi

first time
39:51

Thin japanese she-creatures first time on camera

4 months ago

ShemaleTaxi

japanese, ladyboy, 18, first time
16:59

First Time The Whore Crawls By His Cock

2 months ago

ShemaleZ

amateur, first time, 18
20:49

First time in slavery

2 months ago

XXXDan

latex, bondage, japanese, masturbation, heels, first time
36:30

First time with my machine

4 months ago

AShemaleTube

first time
31:02

Big manhood gf fucked for the first time

8 months ago

ShemaleMovie

first time

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