SHEMALE • FIRST TIME 526 videos

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15:10

My first time as a sissy was so liberating

2 years ago

ShemaleTaxi

crossdresser, taxi, first time, sissy
46:35

First Time With A Shemale

3 years ago

TrannyOne

first time
27:45

Transsexual Aubrey Kate gives him motivation and the cock for his first-ever time

1 week ago

ShemaleMovie

big cock, shemale fucks guy
18:44

Suspended Trans Keira Verga fucks her aficionado for the first-ever time

8 months ago

ShemaleMovie

stockings, blowjob, anal, ass, heels, first time, hardcore
17:03

Teds Ride With Wendy Santos, The Naughty Trans Gives A Blowjob In The Car

9 months ago

BeMyHole

natural, audition, car, riding, first time
33:14

My Hot Online Asian Girlfriend! Were Meeting For The First Time And She Forgot To Tell Me She Has A Cock!

2 months ago

ShemaleZ

shemale, interracial, asian, first time, cum in mouth
17:30

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

7 months ago

JizzBunker

anal, amateur, first time, shemale, couple, mature
18:53

Made His First Time Memorable - Anastasia Penny

12 months ago

ShemaleZ

cumshot, big cock, first time
23:19

First Time For My Husband Fuck With Ladyboy

1 year ago

Upornia

amateur, teen (18+), asian, husband, first time, ladyboy
20:16

First Time Anal with Tundra

2 years ago

TrannyOne

amateur, anal, first time
33:17

His First Time With A Shemale

2 years ago

ShemaleZ

fetish, MILF, big cock, first time
16:52

My first Time

3 years ago

TrannyOne

first time
28:18

Amazing Roxxie Moth Gets Anal Bareback First Time

3 years ago

BeMyHole

cute, stockings, blowjob, first time, hardcore, bareback
15:21

Boy gets to fuck a CD for the first time

6 years ago

xHamster

couple, lingerie, first time
20:49

Big Tits First Timer Gets His Ass Fucked From The Tranny!

12 months ago

BeMyHole

bisexual, big ass, brazil, big tits, latina, domination, bareback
15:21

Popping your TS Cherry

5 years ago

TrannyGem

femdom, strip, first time
23:07

First Time Shemale Sex Virgins

15 years ago

AShemaleTube

first time
27:19

Fucking A T-girl For The First Time With Renata Barbosa And Fernandinha Fernandez

7 months ago

ShemaleZ

shemale and girl, shemale, big ass, MILF, tattoo, first time
46:35

First Time With A Shemale

4 years ago

BeMyHole

first time, stockings
25:17

Vivien Valero First Time shelady Strokers ladyboy

5 years ago

ShemaleZ

cumshot, first time, solo
30:05

White tranny takes BBC for first time

5 years ago

TXXX

interracial, BBC, first time
29:07

Teaching str8 young boy first time ladyboy experience

7 years ago

ShemaleZ

ladyboy, first time
15:21

ADULT TIME - Hottest Very first Rendezvous Ever Casey Calvert Tongues Up T-Nymph Leilani Li Takes DEEP Internal ejaculation

3 days ago

KeekAss

big ass
15:56

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

3 years ago

TrannyGem

femdom, strapon, russian, pegging, first time, chastity, femboy
15:59

Tranny shag a white fellow in donk

3 years ago

TrannyGem

riding, big cock, mask, first time, cum in ass, shemale fucks guy
25:12

Sexy Ladyboy and Super-Cute Educator Real Guy first-ever Time (นางใน)

3 years ago

KeekAss

asian, redhead, first time, shemale fucks guy, cute, ladyboy
21:45

Big Booty Tech Nerd is a Dildo Virgin. Anal Nut First Timer!

4 years ago

BeMyHole

dildo, first time, big tits
21:53

Venezuela transsexuals romping For The first-ever Time!

4 years ago

VideoSection

bisexual, spanish, first time
21:15

Guy first time with blonde Tgirl

5 years ago

ShemaleZ

first time
38:30

Shemale Porn Video Moscardiniema - I Remember The First Time I Saw Manu On Social Media, I Was...

3 months ago

TrannyOne

first time, shemale
20:18

I Record While I Fuck For The First Time With My Transsexual Girlfriend

11 months ago

BeMyHole

first time, dogging
22:55

My first time!

11 months ago

XXXDan

teen (18+), teen anal (18+), first time
20:26

I Record While I Fuck For The First Time With My Transsexual Girlfriend 20 Min

1 year ago

ShemaleZ

redhead, first time
1:29:57

741m584-g03 My Son Who Came Back For The First Time In

1 year ago

ShemaleZ

first time, asian
33:20

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

1 year ago

ShemaleZ

double anal, first time, double penetration
53:13

First Time butthole couple Sex

1 year ago

TrannyOne

shemale, couple, masturbation, first time
23:12

GORGEOUS BRUNETTE WITH WET PUSSY TASTE SHEMALE COCK FIRST TIME

2 years ago

xHamster

creampie, shemale and girl, wet, first time
19:46

MidLife Crisis (v0.30) - Middled age stud creampied for very first time (three)

2 years ago

TrannyGem

teen anal (18+), game, 18, wet, anime, cartoon, first time
33:17

His first time with a shemale

2 years ago

xHamster

vintage, domination, first time
20:47

First time sucking and fucking

2 years ago

TrannyOne

crossdresser, first time
16:43

Feels Like The First Time

2 years ago

ShemaleZ

first time
21:31

Naughty man gets his sweet ass banged hard by the huge TS dick for the first time

3 years ago

TrannyOne

feet, heels, first time
36:34

First time with my Hismith machine

3 years ago

TrannyOne

machine, first time, stockings
22:35

Tgirl fucks Tboy with pussy ................Pussyboy get fucked for first time

3 years ago

TXXX

first time
16:43

Feels Like The First Time . . .

3 years ago

xHamster

first time
1:38:41

My Very First Time With A Trans (Total clothespins)

4 years ago

TrannyGem

full movie, first time
15:31

Guy gets to screw a CD for the very first time

4 years ago

ShemaleMovie

first time
25:54

First time BBC

5 years ago

ShemaleZ

interracial, big tits, BBC, first time
29:19

The first Time Kisses Came Upon Rio

5 years ago

TXXX

kissing, first time, amateur
16:51

My first Time

7 years ago

AShemaleTube

POV, first time
20:31

Blonde for the first time

7 years ago

TXXX

first time
16:30

Teen shemale LOVES first time with boyfriend

9 years ago

TXXX

blowjob, first time, boyfriend
16:01

ADULT TIME - Straight Girl Kenzie Taylor First Trans pummel With fat knocker T-Girl Brittney Kade

1 month ago

ShemaleTaxi

shemale and girl, shemale, first time, fat, taxi
23:46

Her first-ever time with a transgender princess

3 months ago

ShemaleMovie

big cock, shemale, shemale and girl, stockings
22:42

First-ever time big black cock FTM Transman Ethan Hawk

2 years ago

ShemaleTaxi

taxi, BBC, first time, FTM
19:12

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

3 years ago

TrannyGem

public, dogging, BBC, first time, crossdresser
19:26

BARBIE ANDERSON TRANS ARGENTINA DEVERSES HER BEEFY NEPHEW FOR THE FIRST-EVER TIME (TOTAL MOVIE)

3 years ago

TrannyGem

muscle, cousin, first time
19:51

T-Model teenager with yam-sized pink cigar lets dude plow her in the butt

2 years ago

TrannyGem

sissy, first time, cum in ass
15:18

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

2 years ago

TrannyGem

german, bisexual, riding, nylon, slut, first time
18:15

FEMALE DOMINATION HANDBALLING ASS FUCKING INSTRUCTING PEGGING DOMINATRIX SUPREMACY FEMBOY

3 years ago

TrannyGem

femdom, train, instruction, wife, fisting, dildo, pegging
22:37

First Time Shemale Sex Virgins

5 years ago

ShemaleZ

first time
21:45

Guy first time with blonde Tgirl

14 years ago

AShemaleTube

first time, shemale fucks guy
16:30

Anal fisting with my hand, and toy. First time trying to fist my ass

3 weeks ago

JizzBunker

shemale, fisting
33:21

My red-hot online japanese girlfriend! Were meeting for the first time and she forgot to tell me she has a shaft!

2 months ago

ShemaleTaxi

first time, cum in mouth, japanese, girlfriend, anal
19:13

My First Time

2 months ago

ShemaleZ

shemale, shemale and girl, creampie, first time, stockings, lingerie
17:47

I tear up a shemale nymph for the first time 4k

3 months ago

ShemaleTaxi

shemale and girl, first time, shemale
59:26

First Wet Gangbang With Dap! Kittala Gets Dap From 4 Big Cocks For The First Time Eks163 In Hd

4 months ago

HClips

big cock, gangbang, first time, shemale, threesome
15:08

CindiCsissy eats my own cum for the first time

6 months ago

JizzBunker

shemale, first time
22:32

My First Time!

6 months ago

BeMyHole

teen (18+), anal, couple, teen anal (18+), big tits, 18, ass licking
19:29

Blonde sissy in dress used in missionary and first time rimming ass(close up) - LaylacrossFR

7 months ago

AShemaleTube

sissy, shemale, first time
22:42

Blonde sissy in dress used in missionary and first time rimming ass - LaylacrossFR

7 months ago

AShemaleTube

sissy, first time
22:15

Very first time hand-job given by an exotic dark spotted girl

8 months ago

ShemaleMovie

shemale and girl, shemale, first time, BDSM, facesitting
39:51

Thin japanese she-creatures first time on camera

11 months ago

ShemaleTaxi

japanese, ladyboy, 18, first time
39:35

Skinny Asian Ladyboys First Time On Camera

11 months ago

ShemaleZ

amateur, small cock, asian, ladyboy, skinny, small tits, first time
21:50

Trans Fucking A Straight Boy For The First Time

11 months ago

ShemaleZ

BDSM, first time
22:55

My first time!

1 year ago

xHamster

teen (18+), shemale, teen anal (18+), first time
27:54

My Trans Girlfriend Fucks Me For The First Time. She Loves How She Fucks My Ass

1 year ago

BeMyHole

first time, shemale fucks guy, domination
28:15

My trans gf porks me for the very first time. She I love how she boinks my booty

1 year ago

TrannyGem

amateur
28:31

My Trans Girlfriend Fucks Me For The First Time. She Loves How She Fucks My Ass

1 year ago

ShemaleZ

first time, shemale fucks guy
29:24

My Very First Time Creeampied a Pumpkin

1 year ago

TrannyGem

teen (18+), anime
33:17

Graziella Blond - His First Time With A Shemale

1 year ago

ShemaleZ

first time
23:20

First time Sissy training fist with forearms free orgasm!

1 year ago

ShemaleTaxi

orgasm, fisting, first time, femboy, crossdresser
22:38

Tranny Shemale Fucks Straight Guy - First Time Transsexual Fucking

1 year ago

ShemaleZ

first time, shemale fucks guy
16:20

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

1 year ago

ShemaleZ

tattoo, first time
39:15

Cute shemale girl gets anal fucked for the first time

2 years ago

xHamster

cute, first time
15:29

Its my first time letting a shemale rail my shaft

2 years ago

ShemaleTaxi

first time
20:53

BLONDE SHEMALE IN RED LINGERIE TRY BIG LATINA COCK FIRST TIME

2 years ago

xHamster

latina, first time
15:16

My first time being a sissy was so satisfying

2 years ago

ShemaleTaxi

crossdresser, first time
15:37

First Time Eating Ass

2 years ago

Upornia

first time
15:17

Crossdressing for the first time senses so liberating

2 years ago

ShemaleTaxi

lingerie, panties, first time, crossdresser
32:36

Stella First Time Sucking A Shemale Cock

2 years ago

ShemaleZ

outdoor, tattoo, first time
19:27

Gonzo User plows the very first time a trans

2 years ago

ShemaleMovie

fat, german, chubby, BBW, facial, erotic, first time
17:13

Legacy dirt:She on the porn first time, her lucky day. P3

2 years ago

ShemaleTaxi

thai, asian, skinny, taxi, first time
20:07

Skitty In My First Time With A Machine

2 years ago

Upornia

machine, 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
16:30

Femdom tgirl initiation: first time fuckers

2 years ago

TrannyOne

femdom, first time, BDSM
38:26

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

2 years ago

ShemaleZ

POV, first time
17:52

Lady sextasy experiences transgender intense fucking for the first time also enjoys it

2 years ago

TrannyOne

first time, hardcore
21:05

Hot shemale fucks for first time her boyfriend

3 years ago

TrannyOne

first time, boyfriend
16:19

MY VERY FIRST TIME WITH A TRANSVESTI! (JÚLIA DENTTELO)

3 years ago

TrannyGem

brazil, teen anal (18+), first time
44:37

Sex Tourist Bangs A Shemale For The First Time

3 years ago

HClips

threesome, first time, brunette
53:15

Trans Vanessa Jhons welcome Gonzo first time double ana

3 years ago

TrannyOne

first time, double penetration, interracial
15:56

Get ready for your first time with a tranny

4 years ago

AShemaleTube

first time
52:59

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

4 years ago

Upornia

fetish, double anal, gangbang, first time, double penetration
23:46

Guys first Time with Tgirl

4 years ago

BeMyHole

kissing, nipples, 69, panties, jeans, first time, shemale fucks guy
16:39

Female dom transsexual Initiation: first Time Fuckers

4 years ago

ShemaleTaxi

facesitting, domination, first time
33:03

Blonde TS woman fucks the bald mans sweet ass bareback for the first time

4 years ago

BeMyHole

nipples, first time, missionary
16:16

This is my first time fucking a shemale babe

4 years ago

xHamster

babe, first time
45:20

His first time with a Shemale

4 years ago

xHamster

outdoor, first time
32:00

Susie Vicentini - First Time On Camera

5 years ago

ShemaleZ

lingerie, tattoo, ass licking, webcam, first time
19:33

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

5 years ago

ShemaleZ

18, first time
38:59

First-Time Fantasy

5 years ago

ShemaleZ

cum in mouth, bareback, first time
25:06

Hellos First Time With fantastic lady-twink

5 years ago

ShemaleZ

first time
17:36

Fucking first time!

6 years ago

xHamster

first time
26:06

Tranny For The First Time

6 years ago

ShemaleZ

first time
25:36

Hellos First Time With fantastic lady-twink

6 years ago

ShemaleZ

first time
29:36

Teaching str8 young boy first time ladyboy experience

7 years ago

AShemaleTube

erotic, first time
28:25

My trans gf fucks me for the first-ever time. She I love how she fucks my backside

3 months ago

ShemaleTaxi

hardcore, amateur, anal, blowjob, first time
55:16

M584G01 My son-in-law who has returned for the first-ever time in 5 years is a transcendental ts?

3 months ago

ShemaleTaxi

creampie, japanese, cum in mouth, first time
19:55

Thai Ladyboy

7 months ago

JizzBunker

couple, asian, shemale, thai, first time

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