SHEMALE • FIRST TIME 682 videos

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18:51 74%

Fucked by a man for the first time.

5 years ago

ShemaleZ

POV, first time, asian, teen (18+)
20:33 95%

My first time getting dominated by a hot blonde trans babe

4 days ago

XXXVogue

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23:44 61%

First-ever time for my hubby plow with Ladyboy

2 years ago

ShemaleTaxi

handjob, bisexual, anal, orgasm, ladyboy, taxi, first time
18:30 71%

Made His First Time Unforgettable

1 month ago

BeMyHole

shemale, first time, blowjob, domination, hardcore
20:01 91%

Pretty young tgirl ass fucked for the first time

5 years ago

ShemaleZ

stockings, shemale, lingerie, redhead, cumshot, ass, first time
31:37 79%

Shy Couple first time shemale experience 2

5 years ago

AShemaleTube

couple, shy, first time, shemale
2:25:10 67%

First Time Fembois 2

3 years ago

ShemaleZ

redhead, first time, shemale fucks guy, brunette
29:01 87%

Ts Bianca (bibibratx) top for the first time with Cristiano

10 months ago

AShemaleTube

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26:00 82%

First-time blowjob experience with big cock in missionary position featuring Jessica Kate

3 months ago

XXXVogue

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21:06 76%

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

4 years ago

TrannyOne

first time, beauty
15:51

Vol #8: boinked For The first Time on Femout

4 weeks ago

ShemaleTaxi

kissing, small cock, big tits, big cock, deepthroat, bareback, small tits
16:12 62%

Be gentle this is my first time with a tranny

4 years ago

TrannyOne

first time
25:12 65%

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

4 years ago

TrannyGem

blowjob, redhead, first time, shemale fucks guy
16:30 78%

TS Dominance: Initiation of First Time Subs

1 year ago

TrannyOne

BDSM, shemale, domination, first time
16:11 56%

Is this your first time fucking a hot tranny

4 years ago

TrannyOne

first time, amateur
51:27 68%

Little ones first time - all 3 angles

5 years ago

TXXX

asian, bareback, first time, amateur
22:23 72%

Fucked For The Very First Time

4 years ago

TrannyOne

first time
35:58 90%

Fresh faced dickgirl masturbates for the first time on cam

9 years ago

TXXX

solo, masturbation, first time
29:11 92%

Transsexual Bianca (bibibratx) top for the first-ever time with Cristiano

3 months ago

ShemaleTaxi

teen (18+), teen anal (18+), BDSM, tattoo, piercing, big cock, taxi
20:34 93%

My first time dominated by hot blonde tranny LaraMCX

2 weeks ago

AShemaleTube

amateur, homemade, shemale, 18, blonde, ass, cum in mouth
32:17 82%

Helena Price - First Time With A Ladyboy Hd

4 years ago

ShemaleZ

big tits, ladyboy, tattoo, crossdresser, ass licking, first time
16:30 64%

Teen shemale LOVES first time with boyfriend

10 years ago

TXXX

blowjob, first time, boyfriend
22:08 71%

Trans screwing a heterosexual boy for the first-ever time

1 year ago

ShemaleTaxi

amateur, shemale, blowjob, anal, BDSM, first time
25:17

Walkiria Drumond In Blonde Big Tit Tranny Walkiria Fucks Guy Anally For The First Time

1 week ago

HClips

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21:59 85%

Trans nailing a heterosexual stud for the first-ever time

2 years ago

TrannyGem

homemade, reality, first time, shemale fucks guy, amateur, blowjob
17:09

Manmeat-fellating Lessons and freaky Sex: Stepbro Helps Stepsister Overcome Her Shyness and Get Even

2 months ago

ShemaleTaxi

blowjob, shemale, first time, shy
17:35 62%

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

4 years ago

ShemaleMovie

first time, shemale fucks guy, blowjob, amateur
15:53 88%

Vol #10: screwed For The very first Time on Femout

1 month ago

ShemaleTaxi

big cock, shemale fucks guy, small cock, kissing, first time
15:57

The first time

2 years ago

AShemaleTube

amateur, POV, first time
21:52 75%

Brand New Trans Cutie Pixie Pond Fucked by a Man for the First Time Ever

4 months ago

$$ FapHouse

amateur, shemale, blowjob, POV, anal, couple, interracial
16:12 78%

ADULT TIME - Sexy T-Girl Brittney Kade Seduces Nervous Straight For FIRST TIME TRANS FUCK!

2 months ago

SomePorn

first time, shemale, seduced
16:53 75%

Senses Like The first-ever Time . . .

4 years ago

ShemaleTaxi

couple, bareback, first time
18:50 88%

AUBREYS FIRST-EVER TIME

5 years ago

TrannyGem

shemale, first time
21:43 78%

Hot Young Blondie - His First Time

5 months ago

BeMyHole

teen (18+), blowjob, teen anal (18+), dogging, 18, ass licking, domination
21:17 87%

I went to pulverize a trans with a good-sized jizz-shotgun and finished up being violated into by her in the end.

5 months ago

TrannyGem

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23:22 79%

Fucked for the First Time

5 years ago

BeMyHole

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46:35 83%

First Time With A Shemale

4 years ago

TrannyOne

first time
16:00 88%

Femdom Ts Initiation: First Time Fuckers

5 years ago

ShemaleZ

femdom, threesome, first time, fetish
43:28 84%

Shelady Very First Time cam

5 years ago

TrannyGem

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36:39 70%

Comes To Visit For The First Time Surprisingly Is A

1 year ago

ShemaleZ

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23:47 67%

Guys first Time with Tgirl

4 years ago

TrannyOne

69, first time
18:47 50%

The Pill Episode 2 - Chris First Time

2 years ago

JizzBunker

babe, first time
17:07 66%

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

1 year ago

TrannyGem

mom, fat, instruction, facesitting, shemale and girl, stepmom, domination
21:31 92%

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

4 years ago

TrannyOne

feet, heels, first time, fetish
16:16 50%

This is my first time fucking a shemale babe

5 years ago

xHamster

babe, first time, ladyboy
28:10 81%

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

2 years ago

ShemaleZ

amateur, redhead, girlfriend, first time
18:23 76%

Barbie Girls Don't Need A Ken. They Have Their Own Dicks

1 year ago

xHamster

teen (18+), blowjob, shemale and girl, cumshot, first time, creampie
19:52 89%

Shemale teen with big schlong lets stud shag her in the ass

9 months ago

ShemaleMovie

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24:09 83%

Phat Rabbit Killer My First Time

4 years ago

HClips

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46:35 90%

First Time With A Shemale

5 years ago

BeMyHole

first time, stockings
23:10 81%

Fucked For The First Time with Domino Presley

4 years ago

ShemaleZ

first time, shemale fucks guy, MILF
26:22

Shemale Fucks Petite Transgirl for the First Time in the New Year

6 months ago

$$ FapHouse

cumshot, homemade, first time, shemale, couple
37:05

Young Guy fuck the first Time a Shemale

2 years ago

xHamster

first time
15:59 60%

Tranny shag a white fellow in donk

4 years ago

TrannyGem

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53:13 57%

TScumshot.com first time anal couple sex tgirls

4 years ago

TrannyOne

couple, first time, BDSM
22:53

MI PROFESOR FOLLA MI bootie PEQUEÑO DESPUES DE CLASES.

3 months ago

ShemaleMovie

bisexual, anal, big ass, orgasm, BDSM, first time
21:45

Guy first time with blonde Tgirl

15 years ago

AShemaleTube

first time, shemale fucks guy
21:36 81%

Trans Fucking A Straight Boy For The First Time

4 months ago

BeMyHole

amateur, shemale, blowjob, BDSM, redhead, ass licking, reality
16:52

My first Time

4 years ago

TrannyOne

first time
15:30

Vol #2: boinked For The first Time on Femout

2 months ago

ShemaleTaxi

first time, shemale, casting, small cock, anal, big cock, small tits
18:47

BrFat guy gets his thick ass toyed and stretched by the horny TS babe

5 years ago

BeMyHole

dogging, mask, dress, first time
28:18 83%

Amazing Roxxie Moth Gets Anal Bareback First Time

4 years ago

BeMyHole

cute, stockings, blowjob, first time, hardcore, bareback
25:40

Ebony shemale and male Sub kinky sex

2 weeks ago

Analdin

ebony, shemale, fetish, big tits, masturbation, big cock, first time
20:16

First Time Anal with Tundra

3 years ago

TrannyOne

amateur, anal, first time
18:24 81%

The very first time

2 years ago

AShemaleTube

mature, stockings, shemale, lingerie, crossdresser, sissy, first time
16:38 56%

My First Time With A Trans Man

4 months ago

NuVid

shemale fucks guy, shemale, first time
15:31

Guy gets to screw a CD for the very first time

5 years ago

ShemaleMovie

first time
16:37 86%

First Time Topping - T4t Intimate Cute Anal

10 months ago

HClips

shemale and girl, cute, amateur, shemale, POV, first time
20:11 73%

Pretty young tdamsel butt drilled by girl for the first time

5 years ago

ShemaleTaxi

shemale, shemale and girl, taxi, first time
26:35 64%

Sissy very first Time Dressing Up For dad

2 years ago

ShemaleMovie

amateur, crossdresser, dress, sissy, first time
33:17 79%

His very first time with a she-creature

3 years ago

KeekAss

MILF, vintage, domination, first time, shemale fucks guy, anal
16:44 55%

My First Time With A Tranny

2 years ago

BeMyHole

creampie, squirt, shemale and girl, domination, first time, cumshot
1:58:01 60%

Hiiragi Kana In Dass-588 When I Met My Childhood Friend For The First Time In Three Years, I Found Out She Had Become A Stunningly Beautiful Young Woman And We Ended Up Having A Physical Relationship. Kana Hiiragi

8 months ago

ShemaleZ

lingerie, shemale, asian, first time
32:59 50%

Helena Price 1st Time Transgender dame

2 years ago

ShemaleTaxi

shemale, first time
1:24:21 67%

Curvy dark-skinned babe is ready for her first time

2 months ago

XXXVogue

ebony, big ass, chubby, big tits, babe, first time
15:21 78%

ADULT TIME - Lonely T-Girl Emma Rose Has First Romantic Suck And Fuck With Big Dick Roommate!

6 months ago

SomePorn

blowjob, anal, dogging, ass licking, cumshot, ass, deepthroat
34:39 59%

Trans plowing 2 gals for the first time ~KimberlyGeorge~

3 years ago

VideoSection

shemale, threesome, group, first time
37:57 71%

Sexy traps first Video

3 years ago

XXXDan

blonde, skinny, small tits, first time
25:06

Hellos First Time With fantastic lady-twink

6 years ago

ShemaleZ

first time
28:31

Roxxie Cracking In A First-Ever Timer

4 years ago

TrannyGem

first time
19:36

Pretty young tgirl ass fucked by girl for the first time

5 years ago

TXXX

POV, first time, shemale and girl
16:27 83%

Trans girl Selena assfucked for the first time

2 years ago

AShemaleTube

homemade, shemale, blowjob, lingerie, crossdresser, first time
1:00:28 54%

She Is An Innocent Girl Who Is Having Sex For The First Time In A Year. The Old Mans Port Is Fully Erect As He Looks Very Shy. A Big Cock Is Stuck In The Vagina Hole For The First Time In A Year! Two Consecutiv

1 year ago

HClips

creampie, old man, POV, asian, shy, first time
16:51 71%

Young Sexy Ladyboy First Time With Her Sugar Stepdaddy Suck Fuck Cum - Sugar Daddy

6 months ago

HClips

shemale fucks guy, asian, amateur, first time, ladyboy
16:01

BWC Penetrating A Trans For The First-ever Time (Aurora North)

Today

KeekAss

shemale
16:05 56%

Inexperienced real en motel de guerrero. pornography en español!

1 year ago

ShemaleTaxi

homemade, black, small cock, arab, creampie, anal, big ass
15:21

Boy gets to fuck a CD for the first time

7 years ago

xHamster

couple, lingerie, first time
16:19

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

4 years ago

TrannyGem

brazil, teen anal (18+), first time
25:21

Agatha Mama on Teaching My Stepcousin to Eat a Trans Woman for the First Time

Yesterday

$$ FapHouse

brazil, cum in mouth, shemale, MILF
15:34 83%

ASIANTGIRL - Compilation Updates 27th Jan to 31st Jan '25

10 months ago

xHamster

compilation, asian, solo, masturbation, first time, shemale
29:36

Teaching str8 young boy first time ladyboy experience

8 years ago

AShemaleTube

erotic, first time
29:07

Teaching str8 young boy first time ladyboy experience

8 years ago

ShemaleZ

ladyboy, first time
18:38

Melissa Masters - Your Very First Time Trans Femdom GFE

Yesterday

DrTuber

big ass, cumshot, solo, shemale, first time, ass
20:47

First time sucking and fucking

3 years ago

TrannyOne

crossdresser, first time
43:15

First Time on Webcam

5 years ago

BeMyHole

first time
40:52 58%

Tall Trans dame penetrated humid By Tiny CIS Girl

1 year ago

ShemaleTaxi

shemale and girl, tall, shemale, first time
17:57 72%

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

3 years ago

ShemaleTaxi

ladyboy, domination, skinny, first time
15:30 69%

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

2 years ago

xHamster

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33:20

My hot online Asian girlfriend! Were meeting for the first time and she forgot to tell me she has a cock!

1 year ago

XXXDan

girlfriend, shemale, asian, first time
36:39

Carolina Biondi trans active shooting for the first time

11 months ago

XXXDan

small tits, anal, first time
16:40 69%

Perola Martinez gives it to the guy for the first time

2 months ago

XXXVogue

anal, shemale fucks guy, first time, big cock, amateur, blowjob
53:12 84%

First time anal couple sex blonde tgirl

6 years ago

AShemaleTube

homemade, shemale, anal, couple, ass to mouth, webcam, first time
17:52 78%

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

3 years ago

TrannyOne

first time, hardcore
15:03 64%

First time sucking dick? And swallowing my hottest patrons

2 months ago

IcePorn

handjob, shemale, blowjob, POV, swallow, first time
22:54

His First Time With A shetwink

7 years ago

ShemaleZ

first time
18:28

Its time you tasted your first shemale cock

6 years ago

xHamster

first time
15:37

First Time Eating Ass

3 years ago

Upornia

first time
16:51

My first Time

8 years ago

AShemaleTube

POV, first time
15:21

Popping your TS Cherry

6 years ago

TrannyGem

femdom, strip, first time
33:49 88%

Tgata Manuella Gonçalves Did Whatever She Wanted While Riding With Alex Victor.

5 months ago

BeMyHole

amateur, public, anal, big ass, car, latina, ass licking
16:43

Its like its the first time

1 year ago

XXXDan

couple, beauty, skinny, first time, anal, big cock
38:59 56%

First-Time Fantasy

6 years ago

ShemaleZ

cum in mouth, bareback, first time
25:12 63%

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

4 years ago

KeekAss

asian, redhead, first time, shemale fucks guy, cute, ladyboy
16:30 88%

Black guy beeing fucked for his first time by a tgirl

8 months ago

AShemaleTube

black, amateur, shemale, first time
20:09 67%

First Time Working Out With New Gym Buddy Fucks New Tantaly - Emily Adaire And Lina Paige

10 months ago

HClips

solo, first time, amateur, shemale, gym
24:16 57%

Dominant blonde t-girl wrecks her guy toy

1 week ago

XXXVogue

kissing, shemale, anal, BDSM, shemale and girl, blonde, deepthroat
17:10

Young Guy Fucks a Blonde Shemale in Her Tight Asshole for the First Time

3 weeks ago

$$ FapHouse

couple, first time, anal, shemale
53:13 69%

First Time butthole couple Sex

2 years ago

TrannyOne

shemale, couple, masturbation, first time
15:25

Sissy Rozebell experiences wild jizz flow in her butt for the first time

Today

XXXVogue

crossdresser, sissy, BBC, shemale, amateur, femboy
15:49

Vol #3: torn up For The first Time on Femout

1 month ago

ShemaleTaxi

kissing, small cock, blowjob, big cock, small tits, taxi, first time

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