SHEMALE • FIRST TIME 4,030 videos

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04:30 82%

Topping a guy friend for the first time!!!

4 years ago

TrannyOne

first time
07:37 82%

Cutiepii33quinn Gets Her Cherry Arse Nailed For Very First Time

3 months ago

PePorn

POV, amateur, first time
08:00 57%

Christmas orgy first time Slumber Party

7 years ago

IcePorn

teen (18+), first time, party
14:34

Horny couples first time on the honeymoon: A Ts & a TS for your pleasure!

1 week ago

TrannyOne

shemale, first time
08:12 81%

My first time with a real shemale

2 years ago

XXXDan

brazil, orgasm, facial, first time
10:12 89%

My Teen 18+ Stepsister Wants To Try A Cock For The First Time 10 Min - Amanda Riley And Steve Rickz

10 months ago

ShemaleZ

small cock, shemale, 18, first time, small tits
23:44 62%

First-ever time for my hubby plow with Ladyboy

2 years ago

ShemaleTaxi

handjob, bisexual, anal, orgasm, ladyboy, taxi, first time
14:56 57%

Domme T: first-ever Time rope-On Virgin

1 year ago

ShemaleTaxi

shemale, first time, kissing
08:07 87%

I try my transsexual friends cock for the first time

1 year ago

PornDr

handjob, beauty, blowjob, german, wife, cumshot, masturbation
12:07 60%

You will never forget your first time with shemale babe Mel

9 years ago

xHamster

blowjob, babe, erotic, first time
05:08 87%

Dude for the first time gets shemales male stick

6 years ago

Analdin

swinger, party, fetish, first time, hardcore, ladyboy
10:36 72%

My First Time With My New Ejaculating Fantasy Dildo

2 years ago

BeMyHole

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11:52 46%

Your first time with a tranny will be amazing

10 years ago

xHamster

blowjob, erotic, first time, amateur
08:12

My first time with a tranny

2 years ago

xHamster

first time
14:35 52%

Very first time unexperienced crossdresser gets jizz al over by sugar daddy

2 years ago

ShemaleMovie

orgasm, crossdresser, first time
08:09 78%

My very first time

4 years ago

TrannyOne

first time
10:28 74%

Boy very first time with trans

5 years ago

HDSex

first time, amateur
51:27 68%

Little ones first time - all 3 angles

5 years ago

TXXX

asian, bareback, first time, amateur
16:30 67%

Teen shemale LOVES first time with boyfriend

10 years ago

TXXX

blowjob, first time, boyfriend
15:51

Vol #8: boinked For The first Time on Femout

2 months ago

ShemaleTaxi

kissing, small cock, big tits, deepthroat, bareback, small tits, taxi
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
32:17 82%

Helena Price - First Time With A Ladyboy Hd

4 years ago

ShemaleZ

big tits, ladyboy, tattoo, crossdresser, ass licking, first time
01:28 73%

Casting Guy First Time - Itzelxxx

2 years ago

TXXX

casting, first time
05:14 77%

Trans has her first time with her step cousin

2 years ago

ShemaleTaxi

amateur, homemade, anal, cousin, first time, shemale
15:53 84%

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

3 months ago

ShemaleTaxi

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09:30 76%

Asian Transgirl Daniella Teas First Time Getting Fucked By A Guy On Video - Rough Sex

1 year ago

Upornia

asian, shemale, interracial, big cock, first time
12:29 78%

Shy Latino First Time With A Shemale

6 years ago

TXXX

shy, first time
05:17 55%

Cd and Str8 First time

6 years ago

TXXX

first time
07:43

Crystal Phoenix gets plowed hard for her first time with her big booty

2 months ago

XXXVogue

teen anal (18+), femboy, teen (18+), first time, shemale
20:33 92%

My first time getting dominated by a hot blonde trans babe

1 month ago

XXXVogue

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06:15 80%

Straight guys first time to fuck tranny

2 years ago

TrannyOne

first time
12:08 83%

My First Time With A Trans

2 years ago

BeMyHole

amateur, big tits, ass licking, first time, hardcore
07:58

Sydney offers her backside to Max while leaking cum in the school library

Yesterday

XXXVogue

teen (18+), sissy, cumshot compilation, beauty, compilation
11:34 80%

Sissy trans Artemis Asteria gets intimate with roommate for the first time

2 years ago

AnySex

handjob, shemale, blowjob, sissy, first time, small tits
10:36 86%

First-ever time assfucking. Lovely Transgirl plays with herself. Sploog ejaculation

2 years ago

KeekAss

amateur, anal, solo, cumshot, masturbation, first time
23:22 79%

Fucked for the First Time

5 years ago

BeMyHole

femdom, latex, anal, dogging, panties, first time, shemale fucks guy
15:57

The first time

2 years ago

AShemaleTube

amateur, POV, first time
16:00 89%

Femdom Ts Initiation: First Time Fuckers

5 years ago

ShemaleZ

femdom, threesome, first time, fetish
13:25

His very first time with a ladyboy

7 years ago

HDSex

asian, nylon, first time
07:14

Desi village dame tight pussy first time xxx video, desi super-fucking-hot super-sexy tgirl outdoor sex

2 weeks ago

VideoSection

girlfriend, first time, outdoor, indian, babe
06:03

Big Butt Mini Skirt Cheerleader Schoolgirl Uniform White Body Sexy Slut Solo Trans Shemale Big Ass B

1 year ago

xHamster

first time, shemale, wife
33:58

For the first-ever time he put the metal in the trans - Isa Oliveira

1 week ago

KeekAss

handjob, shemale, first time
14:15 80%

Beautiful shemale pounds the guys ass bareback for the first time

4 years ago

TrannyOne

first time
07:39 69%

Trap Schoolgirl Anal For The First Time

6 years ago

TrannyOne

first time
06:25 75%

Ladyboy Amy Fucks Guys Ass For The First Time

3 years ago

DrTuber

blowjob, POV, asian, first time, shemale fucks guy
17:07 65%

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

1 year ago

TrannyGem

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15:03 73%

First time sucking dick? And swallowing my hottest patrons

3 months ago

IcePorn

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08:10

Teenage solo orgasm compilation very first time Ive looked up to President

1 year ago

ShemaleTaxi

first time, solo, orgasm compilation, orgasm, compilation
07:18 79%

TGirl fucks Step sister booty For The First Time

10 months ago

VideoSection

tattoo, blonde, shemale, first time
09:02 71%

J want you to take me like this!

2 months ago

ShemaleTaxi

amateur, shemale, french, lingerie, solo, taxi, first time
10:26

Very first Time - Edible trans ladys backside fucked by a fake penis

1 month ago

KeekAss

first time, amateur, penis
08:14 78%

Trans Taking an anal chastity

7 months ago

ShemaleMovie

creampie, anal, BDSM, crossdresser, british, big cock, bareback
05:00 63%

Ts gets blowjob first time Sneaking Around With Daddys partner

4 years ago

TrannyOne

first time
18:38 50%

Melissa Masters - Your Very First Time Trans Femdom GFE

1 month ago

DrTuber

femdom, solo, cumshot, ass, first time, big ass
14:58 83%

My first time with a trans girl !!

1 year ago

xHamster

amateur, homemade, teen (18+), shemale, bisexual, lingerie, shemale and girl
10:12

My Blonde Busty Trans Stepsister Wants A Anal For The First Time With Steve Rickz And Brittney Kade

3 months ago

ShemaleZ

cum in mouth, first time, big ass, cum in ass
07:59

Curious Guy Tries First Time Anal With A Tranny 10 Min - Very Beautiful, Victoria Di Prada And Victoria Carvalho

1 month ago

Fuxxx

first time
28:18 83%

Amazing Roxxie Moth Gets Anal Bareback First Time

5 years ago

BeMyHole

cute, stockings, blowjob, first time, hardcore, bareback
09:37 74%

Coming Back From A Party, Lizzy Makes Me Very Naughty

12 months ago

BeMyHole

shemale, amateur, shemale and girl, party, first time, MILF
03:34

Melissa Masters In Your Very First Time - Trans Femdom Gfe

2 months ago

Fuxxx

amateur, solo, asian, first time, femdom
04:38

Dudes first time anal sex with shemale

6 years ago

ShemaleZ

first time
14:40

Now is your first time: Blowjob, Amateur Babe Porn

3 months ago

XXXDan

first time, asian, cumshot, missionary
02:25 50%

I was confused the first time I saw this.

10 years ago

xHamster

18, first time
07:19

Tranny and queer gang porno view first time Restrained Benjamin is in

4 years ago

ShemaleTaxi

taxi, first time
21:45

Guy first time with blonde Tgirl

15 years ago

AShemaleTube

first time, shemale fucks guy
08:00 63%

M584g02 Son Who Has Returned For The First Time In A Few Years Is A Transcendental Transsexual

2 years ago

GetTranny

japanese, cum in mouth, first time, asian
12:42

The nylon fetish pt2 Sissy guy first time penetrate ladyboy

5 months ago

ShemaleMovie

big ass, BDSM, shemale, nylon, 3D, first time
2:40:58 65%

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

9 months ago

ShemaleZ

big cock, shemale, asian, shemale and girl, first time
14:39 86%

Ride With A Beautiful & Wonderful Tranny Isabella Salvatore

6 months ago

BeMyHole

beauty, public, big tits, car, 18, jerking, riding
08:08 60%

My very first time

7 years ago

xHamster

anal, first time, shemale fucks guy
18:24 84%

The very first time

2 years ago

AShemaleTube

mature, homemade, stockings, shemale, lingerie, crossdresser, sissy
06:32 86%

Your First Time Getting Fucked by a Trans nymph: First rendezvous GFE point of view Femdom

2 years ago

ShemaleTaxi

femdom, asian, filipina, domination, first time
20:32 80%

Big-ass trans tramp gets it good from ultra-cute femboy prettyboi2000x

2 days ago

XXXVogue

cute, teen (18+), shemale, sissy, femboy, first time, teen anal (18+)
06:34 50%

Trans Girl Punishes And Dominates This Guy And Destroys His Asshole Roughly

2 years ago

BeMyHole

feet, bondage, BDSM, big cock, first time, shemale fucks guy
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
16:08

Guy enjoys first time with busty shemale

1 month ago

XXXVogue

amateur, cumshot, big cock, ass, first time, shemale fucks guy
07:49

Young Time Lady-boy... First Experience!!!!

1 year ago

BeMyHole

first time, 18, asian, uniform
07:32

Trying On My New BIG BLACK TORSO

Yesterday

BeMyHole

black, ebony
10:15 59%

Beautiful 18 yr elderly trans girl fucking for the first time with her new hook-up toy

1 year ago

ShemaleTaxi

amateur, homemade, 18, masturbation, skinny, first time
06:20 60%

Teen guy sucking tranny cock first time

4 years ago

TrannyOne

teen (18+), first time
02:51 67%

FIRST TIME real dick ANAL fuck - TATTOO couple vs shy girl - ATM female orgasm, anal GAPE (goth, punk, alt porn)ZF046

9 months ago

Sexu

lesbian, bisexual, couple, orgasm, tattoo, shy, goth
36:33

Carolina Biondi Trans Active Shooting For The First Time

1 year ago

ShemaleZ

first time, shemale, stockings, lingerie, tattoo
07:37 83%

First time in the Ass iwant a doggy style!

1 year ago

AShemaleTube

cumshot, amateur, first time
08:12

We Met for The First Time with This Married Handsome Man and We Both Went Beyond Borders

2 years ago

xHamster

amateur, cum in mouth, first time, cum in ass
03:12 80%

Crossdresser Fucks Uncle for First Time

7 years ago

ShemaleZ

uncle, first time, crossdresser
02:57 79%

Modest tranny lets her new boyfriend fuck her tight hole for the first time.

1 year ago

AnySex

amateur, POV, blowjob, anal, first time, boyfriend
04:00

The Date: His First Time Discovering His GirlFriend has A HUGE COCK

9 years ago

TXXX

girlfriend, first time
11:30

First Time With A Ts Goddess

2 months ago

ShemaleZ

shemale, cumshot, first time
32:59 50%

Helena Price 1st Time Transgender dame

2 years ago

ShemaleTaxi

shemale, first time
06:09

Auditioning Tranny Tugging her Hard Cock

7 years ago

TrannyGem

casting, blowjob, POV, fetish, jerking, audition, ass
10:57 90%

LEGACY MESS : Filipino fuckslut With Big Cock for the first time in pornography muddy Fucks deep hard in the Throat and Ass of her Partner

2 years ago

ShemaleTaxi

asian, BDSM, ladyboy, big cock, deepthroat, filipina, domination
09:56 60%

Boy first time with tranny

6 years ago

ShemaleZ

first time
06:50

Beautiful Local Girl Hardcore sex with Bf for the First time

8 years ago

AShemaleTube

first time
01:21 69%

Arab Femboy First Time Anal

4 years ago

AShemaleTube

homemade, arab, first time, femboy, domination
06:37

Ultra-kinky man deep throats phat black she-male meat for the very first time

Yesterday

KeekAss

black
07:37

Cutiepii33quinn gets her cherry arse nailed for very first time

4 years ago

TrannyGem

first time
05:32 53%

First time

6 years ago

xHamster

mature, amateur, mature anal, first time
1:29:57

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

2 years ago

ShemaleZ

first time, asian
06:09 50%

Trap first-timer wanks her massive man sausage

7 months ago

ShemaleMovie

femboy, small cock, solo, jerking, first time
04:00 67%

Whats Russian for Suck my Cock? First Time Girl Fucked By TS Teacher

9 years ago

TXXX

russian, teacher, first time
08:14

My first-ever time with a ladyboy

3 months ago

ShemaleMovie

ladyboy, 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
16:19

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

4 years ago

TrannyGem

brazil, teen anal (18+), first time
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

10 months ago

ShemaleZ

lingerie, shemale, asian, first time
19:39

Horny Danish Boy - His First Time

1 month ago

BeMyHole

shemale, anal, hardcore, ass licking, first time, blowjob, danish
05:17

Dudes first time anal bang-out with she-male

3 years ago

ShemaleTaxi

taxi, first time
10:15 71%

Free-for-all Dorian Drake gets barebacked for the first-ever time by gigantic shaft from trans female

2 weeks ago

KeekAss

shemale, blowjob, first time
08:00

Anastasia Penny Made His First Time Memorable

1 year ago

GetTranny

cumshot, first time
29:36

Teaching str8 young boy first time ladyboy experience

8 years ago

AShemaleTube

erotic, first time
16:40 69%

Perola Martinez gives it to the guy for the first time

4 months ago

XXXVogue

anal, shemale fucks guy, first time, big cock, amateur, blowjob
08:12 53%

Skinny teen femboy getting fucked first time

1 year ago

xHamster

german, anal, crossdresser, blonde, skinny, sissy, first time
03:25 47%

Teenie Ginger-Haired uses a String on for the First-Ever Time!(more Content Coming Shortly)

2 years ago

TrannyGem

amateur, femdom, teen (18+), deepthroat, first time, femboy
10:51 50%

My step-dad CATCHES me drilling my bf

6 months ago

ShemaleMovie

caught, shemale fucks guy, first time, cum in mouth, big cock, facial
05:57

Slim blonde t-girl experiences big black cock for the first time in POV

3 weeks ago

XXXVogue

amateur, POV, shemale and girl, BBC, first time
08:01

Teen first time screaming which will probably be the thickest thing sh

4 years ago

TrannyOne

screaming, first time, teen (18+)
04:00 57%

Whats Russian for Suck my Cock First Time Girl Fucked By TS Teacher

11 years ago

TXXX

russian, shemale and girl, teacher, first time
06:13

Transsexual Fatty Blows Dick First Time

1 year ago

GetTranny

first time
10:38 78%

My first-ever ever 3some!!!

5 months ago

ShemaleMovie

amateur, beauty, shemale, double anal, blonde, big cock, babe
11:56 43%

First Time With TS

8 years ago

ShemaleZ

vintage, first time
08:42

First time getting ass fucked

Yesterday

XXXVogue

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