SHEMALE • FIRST TIME 505 videos

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22:58 97%

AI-nosey - sequence 1: first-ever Times (Big Johnson)

3 years ago

ShemaleTaxi

cartoon, taxi, first time
52:54 96%

Trans Vanessa Jhons welcome Gonzo first time double anal

3 years ago

TXXX

shemale, anal, big tits, BDSM, double anal, gangbang, big cock
52:24 94%

Trans Welcome Gonzo First Time Double Butt - Vanessa Jhons

2 years ago

ShemaleZ

big ass, interracial, MILF, tattoo, first time, double penetration
20:01 94%

Pretty young tgirl ass fucked by girl for the first time

5 years ago

PornHub

ass, first time, brunette
20:01 93%

Pretty young tgirl ass fucked for the first time

3 years ago

ShemaleZ

shemale, lingerie, redhead, first time, cumshot
44:17 93%

Kendall Penny - Southern Sass Submits For The First Time!

1 year ago

ShemaleZ

stockings, fetish, BDSM, ass, first time, brunette
20:04 92%

TGIRL POST-OP: Jenny Loves Her New Pussy Fucked

2 years ago

xHamster

couple, interracial, first time, post op
28:15 91%

My trans gf penetrates me for the very first time. She I love how she plows my caboose

4 months ago

KeekAss

anal, crossdresser, bareback, small tits, first time, shemale fucks guy
21:59 84%

Trans nailing a heterosexual stud for the first-ever time

6 months ago

TrannyGem

homemade, blowjob, latina, first time, shemale fucks guy
21:39 84%

Jamie French And Erica Cherry Fuck For The First Time And They Fuck Hard! Ots764

3 years ago

TXXX

french, first time
53:12 84%

First time anal couple sex blonde tgirl

5 years ago

AShemaleTube

homemade, shemale, anal, couple, ass to mouth, webcam, first time
17:21 83%

I Fuck A Tranny Girl For The First Time 4k

1 year ago

ShemaleZ

big ass, shemale and girl, first time, brunette, big tits
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
24:09 83%

Phat Rabbit Killer My First Time

3 years ago

HClips

ebony, interracial, tattoo, ass licking, first time
32:17 83%

Helena Price - First Time With A Ladyboy Hd

2 years ago

ShemaleZ

shemale, big tits, ladyboy, tattoo, ass licking, first time
15:32 82%

Russian Femboy Fucks With Mistress For The First Time With A Huge Strapon Tied With A Chastity

2 years ago

ShemaleZ

femdom, strapon, russian, fisting, tied, first time, chastity
17:26 82%

Alexandra Bxl In Young Guy Fucked In The Ass For The First Time By A Tranny

3 years ago

ShemaleZ

mature, first time, shemale fucks guy
25:12 82%

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

3 years ago

PornHub

old man, dogging, old and young (18+), teacher, first time, cute
18:15 82%

FEMALE DOMINATION HANDBALLING ASSFUCKING INSTRUCTING PEGGING DOMINATRIX PREDOMINANCE FEMBOY

2 years ago

TrannyGem

femdom, train, instruction, wife, fisting, bondage, reality
43:28 81%

Shelady Very First Time cam

3 years ago

TrannyGem

blowjob, creampie, first time
55:15 81%

M584G01 stepson who has returned for the first time in 5 years is a transcendental transsexual?

10 months ago

xHamster

creampie, bisexual, orgasm, japanese, cum in mouth, first time
23:22 81%

Fucked for the First Time

3 years ago

BeMyHole

femdom, latex, dogging, panties, first time, shemale fucks guy
32:51 80%

French tgirl : his first time with a sexy dicky girl

3 years ago

AShemaleTube

french, outdoor, ass to mouth, shemale and girl, blonde, first time
16:53 79%

Senses Like The first-ever Time . . .

3 years ago

ShemaleTaxi

couple, bareback, first time
1:29:57 79%

M584G02 son who has returned for the first time in a few years is a transcendental transsexual.

10 months ago

xHamster

bisexual, orgasm, japanese, cum in mouth, first time
32:02 79%

Smallish fuck-stick transgender princess first time porno

3 years ago

VideoSection

anal, ass, sissy, first time
33:17 77%

His very first time with a she-creature

1 year ago

KeekAss

MILF, vintage, domination, first time, shemale fucks guy
23:44 77%

Her first time with a Shemale

6 years ago

xHamster

lingerie, first time
16:00 77%

Femdom Ts Initiation: First Time Fuckers

3 years ago

ShemaleZ

femdom, threesome, first time
27:53 77%

Anastasia Penny – He Hired An Escort For The First Time

1 year ago

Upornia

big tits, lingerie, first time, escort
15:15 77%

VERY FIRST TIME TRANSGENDER PLOWED IN BOOTY AND CREAMPIED

10 months ago

KeekAss

amateur, stockings, creampie, bareback, first time
21:06 75%

Hot guy gets his ass plowed for the first time by a nasty shemale beauty

2 years ago

TrannyOne

first time
18:24 73%

The very first time

7 months ago

AShemaleTube

mature, homemade, stockings, shemale, crossdresser, first time
28:10 73%

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

5 months ago

ShemaleZ

amateur, redhead, girlfriend, first time
16:42 73%

I Recently Acquired A Giant Tentacle Dildo, And In This Video I Use It For The First Time

9 months ago

BeMyHole

amateur, stockings, dildo, solo, tentacle, first time
22:23 71%

Fucked For The Very First Time

2 years ago

TrannyOne

first time
30:46 71%

Jamie French And Bambi Bliss - First Time Ots846

2 years ago

ShemaleZ

shemale, french, ass licking, first time
16:27 70%

Trans girl Selena assfucked for the first time

6 months ago

AShemaleTube

homemade, shemale, crossdresser, first time
18:49 69%

Unseen Hook-Up Movies Cumpilation - Onlyfans Veronica Sanders

7 months ago

TrannyGem

homemade, blowjob, POV, anal, russian, interracial, shemale and girl
32:50 67%

Gorgeous Darkhair Nasty Shemale Interracial Sex

4 years ago

Analdin

blowjob, anal, big ass, interracial, police, big tits, latina
17:57 67%

Legacy dirt: skinny she-male fucks a guy for the first time. P2

1 year ago

ShemaleTaxi

ladyboy, domination, skinny, first time
23:44 65%

First-ever time for my hubby plow with Ladyboy

1 year ago

ShemaleTaxi

handjob, bisexual, anal, orgasm, ladyboy, taxi, first time
23:47 65%

Guys first Time with Tgirl

2 years ago

TrannyOne

69, first time
19:58 65%

MY FIRST TIME FUCK BEAUTIFUL SHEMALE ON UPSTAIRS

1 year ago

xHamster

beauty, small cock, creampie, anal, interracial, bareback, small tits
20:11 62%

Pretty young tdamsel butt drilled by girl for the first time

3 years ago

ShemaleTaxi

shemale, shemale and girl, taxi, first time
26:35 62%

Sissy very first Time Dressing Up For dad

11 months ago

ShemaleMovie

amateur, crossdresser, dress, sissy, first time
16:44 62%

My First Time With A Tranny

12 months ago

BeMyHole

creampie, squirt, shemale and girl, domination, first time
16:12 60%

Be gentle this is my first time with a tranny

2 years ago

TrannyOne

first time
51:27 58%

Little ones first time - all 3 angles

4 years ago

TXXX

asian, bareback, first time
1:02:42 58%

First Time Visit To The Gloryhole For This attractive playgirl

4 years ago

ShemaleZ

gloryhole, first time
25:12 57%

Cool tranny and lovely tutor Real guy first-ever time (นางใน)

2 years ago

TrannyGem

blowjob, redhead, first time, shemale fucks guy
53:13 57%

TScumshot.com first time anal couple sex tgirls

2 years ago

TrannyOne

couple, first time, BDSM
29:46 56%

Teaching str8 young boy first time she-male experience on webcam

4 years ago

HDSex

webcam, first time, femboy
34:39 55%

Trans plowing 2 gals for the first time ~KimberlyGeorge~

1 year ago

VideoSection

shemale, threesome, group, first time
22:46 55%

Sissy lad gets to fuck the trans babes thick ass for the first time

2 years ago

TrannyOne

feet, ass to mouth, cum in mouth, sissy, first time, cum in ass
2:25:10 53%

First Time Fembois 2

1 year ago

ShemaleZ

redhead, first time, shemale fucks guy, brunette
21:03 52%

T Gurl Cums in her dress

3 years ago

xHamster

public, outdoor, compilation, dress, cumshot compilation, first time
15:10 50%

Thai girl taste big shemale cock first time

1 year ago

xHamster

thai, first time
17:07

Step-Mom instruct a significant lesson to her fresh step daughter-in-law (How to be a tramp)

1 month ago

TrannyGem

mom, shemale, fat, anal, instruction, facesitting, shemale and girl
31:37

Shy Couple first time shemale experience 2

4 years ago

AShemaleTube

couple, shy, first time
24:59

Old Futa Girl-On-Girl Tranny Humps Young Very First Time Cherry With Numerous Ejaculations - Sims four

2 weeks ago

TrannyGem

shemale, lesbian, shemale and girl, old and young (18+), cartoon, futanari, creampie
36:39

Comes To Visit For The First Time Surprisingly Is A

2 days ago

ShemaleZ

first time, shemale, surprise, asian, stockings
15:34

Horny in the Morning! Surprise Sex, Dangerous Spiky Piercing Blowjob & first-ever Time facial cumshot Cumshot

3 years ago

ShemaleTaxi

surprise
22:15

Very first time hj given by an exotic dark eyed girl

1 month ago

ShemaleTaxi

handjob, shemale, BDSM, facesitting, jerking, taxi, first time
32:13

Sensational DEBUT: The miracle You can Only see Here - First Time Crossdresser Rina : See More→https://bit.ly/EagleGay

1 year ago

ShemaleMovie

asian, japanese, first time
2:36:25

Yui Hatano And Hibiki Otsuki - Dass-133 First Time Nh Lesbian Sex. Kanami Kashiwagi Yu

12 months ago

ShemaleZ

lesbian, asian, uniform, first time
22:15

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

2 weeks ago

ShemaleMovie

shemale and girl, shemale, first time, BDSM
23:10

Fucked For The First Time with Domino Presley

3 years ago

ShemaleZ

first time, shemale fucks guy
39:41

Skinny Asian ladyboys first time on camera

4 months ago

xHamster

anal, japanese, skinny, first time, asian, amateur
38:29

Moscardiniema - I Remember The First Time I Saw Manu On Social Media, I Was Laying In Bed And It Was About 11pm, I Literally Couldnt Believe My Eyes.

7 months ago

BeMyHole

stockings, big tits, blonde, first time, hardcore
35:58

Fresh faced dickgirl masturbates for the first time on cam

7 years ago

TXXX

solo, masturbation, first time
25:17

Vivien Valero First Time shelady Strokers ladyboy

4 years ago

ShemaleZ

cumshot, first time, solo
24:59

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

2 weeks ago

PornHub

shemale, lesbian, orgasm, big tits, shemale and girl, cumshot, cartoon
18:44

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

3 weeks ago

ShemaleMovie

stockings, first time, anal, shemale, blowjob, heels, ass
15:58

Ladyboy fuck a white dude in ass

3 years ago

PornHub

russian, dogging, mask, first time, shemale fucks guy, brunette, cum in ass
20:49

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

4 months ago

BeMyHole

bisexual, big ass, brazil, big tits, latina, domination, bareback
19:43

MidLife Crisis (v0.30) - Hetero man having first time anal with a trap (3)

1 year ago

xHamster

small cock, creampie, 18, small tits, first time
19:29

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

1 week ago

AShemaleTube

sissy, shemale
16:11

Is this your first time fucking a hot tranny

2 years ago

TrannyOne

first time
39:11

A nosey woman tries a shemales spunk-pump for the very first time

2 years ago

ShemaleTaxi

shemale and girl, pump, taxi, first time
16:43

Feels Like The First Time . . .

2 years ago

TrannyOne

skinny, first time
15:57

The first time

7 months ago

AShemaleTube

amateur, POV, first time
17:08

Skylar and Rays First Time Part 1

4 years ago

TXXX

first time
18:53

Made His First Time Memorable - Anastasia Penny

4 months ago

ShemaleZ

cumshot, big cock, first time
37:05

Young Guy fuck the first Time a Shemale

7 months ago

xHamster

first time
18:47

The Pill Episode 2 - Chris First Time

7 months ago

JizzBunker

babe, first time
15:10

My first time as a sissy was so liberating

1 year ago

ShemaleTaxi

crossdresser, taxi, first time, sissy
18:50

AUBREYS FIRST-EVER TIME

3 years ago

TrannyGem

shemale, 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
17:35

Young dude screwed in the ass for the first time by a tranny

3 years ago

ShemaleMovie

first time, shemale fucks guy
16:12

Stephie scarlet first time pegging a tgirl

7 months ago

IcePorn

pegging, first time
28:17

My trans girlfriend fucks me for the first time. She loves how she fucks my ass

8 months ago

xHamster

homemade, ladyboy, first time, shemale fucks guy, latina
39:15

Cute shemale girl gets anal fucked for the first time

1 year ago

xHamster

cute, first time
28:27

My trans gf screws me for the first-ever time. She loves how she fucks my ass

5 months ago

ShemaleTaxi

amateur, blowjob, girlfriend, first time, shemale fucks guy
19:43

MidLife Crisis v0.30 - Straight man gets anal for the first time with a trap 3

3 months ago

JizzBunker

small cock, creampie, anal, college, cartoon, first time
1:45:31

Big T In *limited First Time* [innocent Big Breasts Girl] Too Le

5 months ago

Upornia

shemale and girl, first time
22:00

Ts In Stockings Ingrid Moreira The First Time

2 years ago

BeMyHole

piercing, condom, shaving, first time, shemale fucks guy
19:50

Thai Transgender Princess

2 years ago

TrannyGem

asian, first time
15:30

I arrived by surprise. It was his first time sucking a shemale

10 months ago

xHamster

amateur, couple, shemale and girl, compilation, surprise, cumshot compilation, first time
46:35

First Time With A Shemale

3 years ago

BeMyHole

first time
25:45

FUTANARIA FIRST TIME FUCK BUDDIES

3 years ago

ShemaleZ

first time
37:57

Sexy traps first Video

2 years ago

XXXDan

blonde, skinny, small tits, first time
17:46

I pulverize a she-creature woman for the first-ever time 4k

2 years ago

TrannyGem

squirt, first time
17:03

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

2 months ago

BeMyHole

natural, audition, car
22:42

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

1 week ago

AShemaleTube

sissy
2:55:43

First Time Fembois

1 year ago

Upornia

stockings, first time
15:57

Yvanas First Time On Porn - Alexandra Bxl

1 year ago

ShemaleZ

stockings, lingerie, first time
16:11

Is this your very first time tearing up a red-hot transgender princess

4 years ago

TrannyGem

first time
16:30

Teen shemale LOVES first time with boyfriend

8 years ago

TXXX

blowjob, first time, boyfriend
21:47

TGIRLS.GONZO: Moscow Sweetie Gets Her Donk Humped

2 years ago

TrannyGem

russian, screaming, first time
19:51

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

1 year ago

TrannyGem

sissy, first time, cum in ass
21:45

Guy first time with blonde Tgirl

13 years ago

AShemaleTube

first time
23:07

First Time Shemale Sex Virgins

14 years ago

AShemaleTube

first time
26:23

Tranny fucks a little trans for the first time on the New Year

1 month ago

JizzBunker

small cock, tattoo, shemale, first time, beauty
39:35

Skinny Asian Ladyboys First Time On Camera

3 months ago

ShemaleZ

amateur, small cock, ladyboy, skinny, first time
23:20

First time Sissy training fist with forearms free orgasm!

11 months ago

ShemaleTaxi

orgasm, fisting, first time, femboy
17:25

Young guy fucked in the ass for the first time by a tranny

3 years ago

xHamster

mature anal, couple, first time, shemale fucks guy
18:51

Fucked by a man for the first time.

3 years ago

ShemaleZ

POV, first time
16:16

This is my first time fucking a shemale babe

3 years ago

xHamster

babe, first time
15:13

Ftm gets pegged by wife for the first time

4 years ago

ShemaleZ

wife, shemale and girl, pegging, first time, FTM

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