SHEMALE • FIRST TIME 720 videos

Popular Latest Top rated

34:12 75%

Milf Silvana Lee has Hardcore Sex with Her Brothers Sexy Shemale Girlfriend ...

9 months ago

Beeg

shemale, cuckold, first time, girlfriend, dogging, latina
18:51 76%

Fucked by a man for the first time.

5 years ago

ShemaleZ

POV, first time, asian, teen (18+)
23:44 62%

First-ever time for my hubby plow with Ladyboy

2 years ago

ShemaleTaxi

handjob, bisexual, anal, orgasm, ladyboy, taxi, first time
18:30 70%

Made His First Time Unforgettable

4 months ago

BeMyHole

shemale, first time, blowjob, domination, hardcore
20:34 94%

My first time dominated by hot blonde tranny LaraMCX

2 months ago

AShemaleTube

homemade, shemale, 18, ass, cum in mouth, domination, bareback
21:41

MY HOMIE WOOED ME TO ATTEMPT A BIG BLACK COCK FOR THE VERY FIRST TIME - ALEJANDRA PALACIOS

4 days ago

KeekAss

shemale, black, BBC, hardcore, first time
31:37 78%

Shy Couple first time shemale experience 2

5 years ago

AShemaleTube

couple, shy, first time, shemale
20:01 92%

Pretty young tgirl ass fucked for the first time

5 years ago

ShemaleZ

stockings, shemale, lingerie, redhead, cumshot, ass, first time
24:41 87%

Cunty bride hook up BBC for first time

3 weeks ago

AShemaleTube

amateur, bride, shemale, anal, interracial, big cock, domination
2:25:10 67%

First Time Fembois 2

3 years ago

ShemaleZ

redhead, first time, shemale fucks guy, brunette
29:01 88%

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

1 year ago

AShemaleTube

big ass, interracial, big cock, ass, domination, first time, shemale fucks guy
17:45 50%

Straight Guy First Time Fucking a Sissy Crossdresser That Swallows Cum

1 month ago

$$ FapHouse

blowjob, anal, couple, latina, crossdresser, swallow, cum in mouth
16:30 79%

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
26:00 79%

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

5 months ago

XXXVogue

amateur, spanish, big ass, big cock, ass, first time, missionary
28:45

Etero Couple Tries a Shemale Fuck for the First Time

3 weeks ago

$$ FapHouse

18, teen (18+), vintage, first time, threesome
16:12 63%

Be gentle this is my first time with a tranny

4 years ago

TrannyOne

first time
29:11 90%

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

6 months ago

ShemaleTaxi

teen (18+), teen anal (18+), BDSM, tattoo, piercing, big cock, domination
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
16:30 67%

Teen shemale LOVES first time with boyfriend

10 years ago

TXXX

blowjob, first time, boyfriend
32:17 82%

Helena Price - First Time With A Ladyboy Hd

4 years ago

ShemaleZ

big tits, ladyboy, tattoo, crossdresser, ass licking, 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
35:58 91%

Fresh faced dickgirl masturbates for the first time on cam

9 years ago

TXXX

solo, masturbation, first time
22:08 72%

Trans screwing a heterosexual boy for the first-ever time

1 year ago

ShemaleTaxi

amateur, shemale, blowjob, anal, BDSM, first time
15:51

Vol #8: boinked For The first Time on Femout

3 months ago

ShemaleTaxi

kissing, small cock, deepthroat, bareback, small tits, taxi, first time
18:50 88%

AUBREYS FIRST-EVER TIME

5 years ago

TrannyGem

shemale, first time
21:59 84%

Trans nailing a heterosexual stud for the first-ever time

2 years ago

TrannyGem

homemade, reality, first time, shemale fucks guy, amateur, blowjob
21:52 77%

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

6 months ago

$$ FapHouse

amateur, shemale, blowjob, POV, anal, couple, interracial
17:35 64%

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

5 years ago

ShemaleMovie

first time, shemale fucks guy, blowjob, amateur, stockings
21:43 70%

Hot Young Blondie - His First Time

7 months ago

BeMyHole

teen (18+), blowjob, teen anal (18+), dogging, 18, ass licking, domination
20:33 93%

My first time getting dominated by a hot blonde trans babe

2 months ago

XXXVogue

shemale, blowjob, anal, big tits, BDSM, blonde, babe
21:06 75%

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

4 years ago

TrannyOne

first time, beauty
17:09 60%

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

4 months ago

ShemaleTaxi

blowjob, shemale, first time, shy
23:22 79%

Fucked for the First Time

5 years ago

BeMyHole

femdom, latex, anal, dogging, panties, first time, shemale fucks guy
16:08

Guy enjoys first time with busty shemale

1 month ago

XXXVogue

amateur, cumshot, big cock, ass, first time, shemale fucks guy
16:53 75%

Senses Like The first-ever Time . . .

4 years ago

ShemaleTaxi

couple, bareback, first time
15:53 84%

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

3 months ago

ShemaleTaxi

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

The first time

2 years ago

AShemaleTube

amateur, POV, first time
43:28 82%

Shelady Very First Time cam

5 years ago

TrannyGem

blowjob, creampie, first time, anal, masturbation, webcam
16:00 89%

Femdom Ts Initiation: First Time Fuckers

5 years ago

ShemaleZ

femdom, threesome, first time, fetish
29:59 87%

Sinn Sage And Erica Cherry - Astonishing Sex Scene Shemale Milf Exotic Just For You

3 years ago

Upornia

shemale, MILF, shemale and girl, cumshot, toys, first time
46:35 85%

First Time With A Shemale

4 years ago

TrannyOne

first time
18:47 50%

The Pill Episode 2 - Chris First Time

2 years ago

JizzBunker

babe, first time
44:27

Ultra-kinky college girl anal invasion fuck-a-thon

Yesterday

ShemaleTaxi

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36:39 71%

Comes To Visit For The First Time Surprisingly Is A

1 year ago

ShemaleZ

first time, shemale, surprise, asian, stockings
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.

8 months ago

TrannyGem

creampie, muscle, big tits, blonde, big cock, ass, futanari
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
46:35 90%

First Time With A Shemale

5 years ago

BeMyHole

first time, stockings
23:47 67%

Guys first Time with Tgirl

4 years ago

TrannyOne

69, first time
21:36 82%

Trans Fucking A Straight Boy For The First Time

6 months ago

BeMyHole

amateur, blowjob, BDSM, redhead, ass licking, reality, first time
17:07 63%

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
16:37 88%

First Time Topping - T4t Intimate Cute Anal

1 year ago

HClips

shemale and girl, cute, amateur, shemale, POV, first time
33:49 84%

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

7 months ago

BeMyHole

amateur, public, blowjob, anal, big ass, car, latina
19:52 89%

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

11 months ago

ShemaleMovie

ass, skinny, sissy, first time, shemale fucks guy, cum in ass
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
28:10 82%

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
15:59 60%

Tranny shag a white fellow in donk

4 years ago

TrannyGem

riding, big cock, mask, first time, cum in ass, shemale fucks guy
53:13 55%

TScumshot.com first time anal couple sex tgirls

4 years ago

TrannyOne

couple, first time, BDSM
28:18 83%

Amazing Roxxie Moth Gets Anal Bareback First Time

5 years ago

BeMyHole

cute, stockings, blowjob, first time, hardcore, bareback
15:03 74%

First time sucking dick? And swallowing my hottest patrons

4 months ago

IcePorn

handjob, shemale, blowjob, POV, swallow, first time
26:22

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

9 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
30:15 80%

Femout XXX: Nurse Kays First Time on Film

2 months ago

$$ FapHouse

shemale, anal, couple, first time
24:09 82%

Phat Rabbit Killer My First Time

5 years ago

HClips

ebony, interracial, tattoo, ass licking, first time, amateur
18:38 50%

Melissa Masters - Your Very First Time Trans Femdom GFE

2 months ago

DrTuber

femdom, solo, cumshot, ass, first time, big ass
21:45

Guy first time with blonde Tgirl

15 years ago

AShemaleTube

first time, shemale fucks guy
15:31

Guy gets to screw a CD for the very first time

5 years ago

ShemaleMovie

first time
20:16

First Time Anal with Tundra

3 years ago

TrannyOne

amateur, anal, first time
23:10 81%

Fucked For The First Time with Domino Presley

5 years ago

ShemaleZ

first time, shemale fucks guy, MILF
16:52

My first Time

4 years ago

TrannyOne

first time
18:24 84%

The very first time

2 years ago

AShemaleTube

mature, homemade, stockings, shemale, lingerie, crossdresser, sissy
16:12 73%

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

4 months ago

SomePorn

first time, shemale, seduced
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
25:06

Hellos First Time With fantastic lady-twink

6 years ago

ShemaleZ

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
32:59 50%

Helena Price 1st Time Transgender dame

2 years ago

ShemaleTaxi

shemale, first time
37:57 73%

Sexy traps first Video

4 years ago

XXXDan

blonde, skinny, small tits, first time
16:44 58%

My First Time With A Tranny

2 years ago

BeMyHole

creampie, squirt, shemale and girl, big cock, domination, 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
15:21 78%

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

9 months ago

SomePorn

blowjob, dogging, ass licking, cumshot, ass, deepthroat, reality
26:35 64%

Sissy very first Time Dressing Up For dad

2 years ago

ShemaleMovie

amateur, crossdresser, dress, sissy, 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
16:19

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

4 years ago

TrannyGem

brazil, teen anal (18+), first time
15:46 69%

Turning My husband Into Tranny tart, lady first time with Tranny

1 year ago

ShemaleMovie

shemale, strapon, train, BDSM, crossdresser, husband, ass
36:33

Carolina Biondi Trans Active Shooting For The First Time

1 year ago

ShemaleZ

first time, shemale, stockings, lingerie, tattoo
2:40:58 67%

Mooc-002 When I Met My Childhood Friend For The First Time In A Year, He Had Become A Yandere Girl. He Showed Me His Big Dick And I Got Aroused, So I Had Anal Sex With Him And Ejaculated Inside Him Over And Over Again. Hifumi Yuuri

10 months ago

ShemaleZ

big cock, shemale, asian, shemale and girl, first time
1:00:28 57%

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, shemale and girl, shy, first time
16:16 44%

This is my first time fucking a shemale babe

5 years ago

xHamster

babe, first time, ladyboy, blowjob
16:38 53%

My First Time With A Trans Man

6 months ago

NuVid

shemale fucks guy, shemale, first time
22:46 53%

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

4 years ago

TrannyOne

feet, ass to mouth, cum in mouth, sissy, first time, cum in ass
16:05 54%

Inexperienced real en motel de guerrero. pornography en español!

1 year ago

ShemaleTaxi

homemade, black, small cock, arab, creampie, anal, big ass
34:39 59%

Trans plowing 2 gals for the first time ~KimberlyGeorge~

3 years ago

VideoSection

shemale, threesome, group, first time
28:31

Roxxie Cracking In A First-Ever Timer

5 years ago

TrannyGem

first time
15:34 81%

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

1 year 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
16:27 83%

Trans girl Selena assfucked for the first time

2 years ago

AShemaleTube

homemade, shemale, blowjob, lingerie, crossdresser, shemale and girl, first time
15:49 57%

Vol #6: boned For The first-ever Time on Femout

3 months ago

ShemaleTaxi

kissing, small cock, shemale, blowjob, big tits, masturbation, big cock
15:21

Boy gets to fuck a CD for the first time

7 years ago

xHamster

couple, lingerie, first time
1:58:01 63%

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

11 months ago

ShemaleZ

lingerie, shemale, asian, first time, swallow
22:54

His First Time With A shetwink

7 years ago

ShemaleZ

first time
53:12 84%

First time anal couple sex blonde tgirl

7 years ago

AShemaleTube

homemade, anal, couple, ass to mouth, webcam, first time, frottage
29:07

Teaching str8 young boy first time ladyboy experience

8 years ago

ShemaleZ

ladyboy, first time
25:40 83%

Ebony tranny wants his virgin asshole

2 months ago

XoZilla

ebony, homemade, fetish, big cock, ass, asshole, first time
16:40 69%

Perola Martinez gives it to the guy for the first time

5 months ago

XXXVogue

anal, shemale fucks guy, first time, big cock, amateur, blowjob
38:59 56%

First-Time Fantasy

6 years ago

ShemaleZ

cum in mouth, bareback, first time
16:51

My first Time

8 years ago

AShemaleTube

POV, first time
20:09 67%

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

1 year ago

HClips

solo, first time, amateur, shemale, gym
1:24:21 67%

Curvy dark-skinned babe is ready for her first time

4 months ago

XXXVogue

ebony, big ass, chubby, big tits, babe, first time
20:47

First time sucking and fucking

3 years ago

TrannyOne

crossdresser, first time
16:51 70%

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

8 months ago

HClips

shemale fucks guy, asian, amateur, first time, ladyboy
15:30 67%

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

2 years ago

xHamster

blowjob, couple, shemale and girl, compilation, surprise, cumshot compilation, first time
1:29:57 76%

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

2 years ago

xHamster

bisexual, orgasm, japanese, cum in mouth, first time
17:57 74%

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

3 years ago

ShemaleTaxi

ladyboy, domination, skinny, first time
40:52 59%

Tall Trans dame penetrated humid By Tiny CIS Girl

1 year ago

ShemaleTaxi

shemale and girl, tall, shemale, first time
16:43

Its like its the first time

1 year ago

XXXDan

couple, beauty, skinny, first time, anal, big cock
43:15

First Time on Webcam

5 years ago

BeMyHole

first time
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
25:12 67%

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
24:46 67%

I have been fucked in the ass for the first time by a ladyboy

2 months ago

AShemaleTube

shemale, shemale fucks guy, amateur, ladyboy, first time

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