SHEMALE • FIRST TIME 3,944 videos

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04:30 82%

Topping a guy friend for the first time!!!

4 years ago

TrannyOne

first time
07:37 85%

Cutiepii33quinn Gets Her Cherry Arse Nailed For Very First Time

1 month ago

PePorn

POV, amateur, first time
10:28 73%

Boy very first time with trans

5 years ago

HDSex

first time, amateur
03:06 75%

Transgender scene with sultry fiancée from Grooby Girls

1 month ago

PornHat

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11:34 79%

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

2 years ago

AnySex

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06:25 75%

Ladyboy Amy Fucks Guys Ass For The First Time

3 years ago

DrTuber

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08:12 82%

My first time with a real shemale

1 year ago

XXXDan

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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

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10:12 86%

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

9 months ago

ShemaleZ

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14:56 58%

Domme T: first-ever Time rope-On Virgin

1 year ago

ShemaleTaxi

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08:07 85%

I try my transsexual friends cock for the first time

1 year ago

PornDr

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08:00 57%

Christmas orgy first time Slumber Party

6 years ago

IcePorn

teen (18+), first time, party
12:07 59%

You will never forget your first time with shemale babe Mel

9 years ago

xHamster

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15:51

Vol #8: boinked For The first Time on Femout

4 weeks ago

ShemaleTaxi

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05:08 88%

Dude for the first time gets shemales male stick

6 years ago

Analdin

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10:36 72%

My First Time With My New Ejaculating Fantasy Dildo

2 years ago

BeMyHole

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25:12 65%

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

4 years ago

TrannyGem

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08:09 78%

My very first time

4 years ago

TrannyOne

first time
11:52 45%

Your first time with a tranny will be amazing

10 years ago

xHamster

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14:35 52%

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

2 years ago

ShemaleMovie

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51:27 68%

Little ones first time - all 3 angles

5 years ago

TXXX

asian, bareback, first time, amateur
03:34

Melissa Masters In Your Very First Time - Trans Femdom Gfe

1 month ago

Fuxxx

amateur, solo, asian, first time, femdom
32:17 82%

Helena Price - First Time With A Ladyboy Hd

4 years ago

ShemaleZ

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05:14 76%

Trans has her first time with her step cousin

2 years ago

ShemaleTaxi

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01:28 78%

Casting Guy First Time - Itzelxxx

2 years ago

TXXX

casting, first time
16:30 64%

Teen shemale LOVES first time with boyfriend

10 years ago

TXXX

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10:12

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

1 month ago

ShemaleZ

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02:18

First-Ever Time Rapper Porks Transgender in V-Card

1 week ago

TrannyGem

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09:30 78%

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

1 year ago

Upornia

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12:29 81%

Shy Latino First Time With A Shemale

6 years ago

TXXX

shy, first time
15:53 88%

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

1 month ago

ShemaleTaxi

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15:57

The first time

2 years ago

AShemaleTube

amateur, POV, first time
11:30

First Time With A Ts Goddess

2 weeks ago

ShemaleZ

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06:15 80%

Straight guys first time to fuck tranny

2 years ago

TrannyOne

first time
05:17 55%

Cd and Str8 First time

6 years ago

TXXX

first time
12:08 83%

My First Time With A Trans

2 years ago

BeMyHole

amateur, big tits, ass licking, first time, hardcore
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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13:25

His very first time with a ladyboy

7 years ago

HDSex

asian, nylon, first time
23:22 79%

Fucked for the First Time

5 years ago

BeMyHole

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03:25 44%

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

2 years ago

TrannyGem

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10:36 86%

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

1 year ago

KeekAss

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16:00 88%

Femdom Ts Initiation: First Time Fuckers

5 years ago

ShemaleZ

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05:32

I came for the very first time

1 month ago

TrannyGem

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04:31

Assfucking Internal Ejaculation Gushes Out Onto Camera As Lil Trans Gets Plumbed

4 days ago

TrannyGem

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07:43

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

1 month ago

XXXVogue

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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

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07:12

Very first Time in Public

3 days ago

ShemaleMovie

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16:01

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

Today

KeekAss

shemale
12:42

The nylon fetish pt2 Sissy guy first time penetrate ladyboy

3 months ago

ShemaleMovie

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08:10

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

1 year ago

ShemaleTaxi

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07:37 83%

First time in the Ass iwant a doggy style!

1 year ago

AShemaleTube

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18:38

Melissa Masters - Your Very First Time Trans Femdom GFE

Yesterday

DrTuber

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07:39 69%

Trap Schoolgirl Anal For The First Time

6 years ago

TrannyOne

first time
02:51 69%

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

7 months ago

Sexu

lesbian, bisexual, couple, orgasm, tattoo, shy, goth
14:58 84%

My first time with a trans girl !!

1 year ago

xHamster

amateur, homemade, teen (18+), shemale, lingerie, shemale and girl, big cock
10:15 59%

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

1 year ago

ShemaleTaxi

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02:25 60%

I was confused the first time I saw this.

10 years ago

xHamster

18, first time
14:40

Now is your first time: Blowjob, Amateur Babe Porn

2 months ago

XXXDan

first time, asian, cumshot, missionary
21:45

Guy first time with blonde Tgirl

15 years ago

AShemaleTube

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02:25

Twenty one yo Finnish trans dolls first-ever time getting poked on camera

8 months ago

TrannyGem

teen (18+), amateur, first time, POV, teen anal (18+), finnish
03:47

First time out my cage for a week.

Today

AShemaleTube

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05:15

Shemales donk acquires poked stiff

4 months ago

ShemaleMovie

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06:55

College-aged yr elder schoolgirl gal nailing with the instructor for the very first time to pass the examination

Today

TrannyGem

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06:32 88%

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

2 years ago

ShemaleTaxi

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09:47

Cute Lexi Lore Gets Fucked By TS For The First Time

1 year ago

BeMyHole

first time
07:52

Pierce Pariss Made Desire in First Bliss

3 days ago

XoZilla

missionary, heels, shemale, first time
07:19

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

4 years ago

ShemaleTaxi

taxi, first time
12:53

She made me spunk two times! Very First time fuckin Britney from Tantaly - Emily Adaire

Yesterday

TrannyGem

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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
06:20 60%

Teen guy sucking tranny cock first time

4 years ago

TrannyOne

teen (18+), first time
10:07

Barely legal yr older ts chick wanks for the first-ever time in her stepparents van

Yesterday

TrannyGem

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18:24 81%

The very first time

2 years ago

AShemaleTube

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06:10 69%

Dudes very first Time With A t-girl

5 years ago

HDSex

prostitute, first time
08:07 67%

TRANSSEXUAL Kim Wagner bangs a young homo, it is him first-ever time

9 months ago

TrannyGem

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04:38

Dudes first time anal sex with shemale

6 years ago

ShemaleZ

first time
07:49

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

1 year ago

BeMyHole

first time, 18, asian, uniform
06:34

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

1 year ago

BeMyHole

feet, bondage, BDSM, big cock, first time, shemale fucks guy
07:18 79%

TGirl fucks Step sister booty For The First Time

8 months ago

VideoSection

tattoo, blonde, shemale, 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

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
10:10

My first time in sexy lingerie and a wig... do I look good enough?

Today

XXXVogue

tease, crossdresser
15:21 78%

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

6 months ago

SomePorn

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05:17

Fucking sexy shemale bitch likes each inch of boner in culo

Yesterday

ShemaleMovie

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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

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08:00 59%

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
01:21 68%

Arab Femboy First Time Anal

4 years ago

AShemaleTube

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07:37

Cutiepii33quinn gets her cherry arse nailed for very first time

4 years ago

TrannyGem

first time
06:50

Beautiful Local Girl Hardcore sex with Bf for the First time

8 years ago

AShemaleTube

first time
09:27

Exploring my backside for the first time (Full video on Fansly)

Yesterday

XXXVogue

masturbation
08:12 54%

Skinny teen femboy getting fucked first time

11 months ago

xHamster

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08:12

My first time with a tranny

2 years ago

xHamster

first time
05:32 57%

First time

6 years ago

xHamster

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12:38

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3 days ago

TrannyGem

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03:40

First Time Guest Anally Fucked In The House

3 months ago

xShemaleTube

first time
16:51 71%

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

6 months ago

HClips

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09:56 60%

Boy first time with tranny

6 years ago

ShemaleZ

first time
15:25

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

Today

XXXVogue

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22:46 53%

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

3 years ago

TrannyOne

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11:02

Pretty Ebony TRANSSEXUAL YPB In Her Very first Time Humping A Fellows Arse

Yesterday

KeekAss

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10:51 50%

My step-dad CATCHES me drilling my bf

4 months ago

ShemaleMovie

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06:09 40%

Trap first-timer wanks her massive man sausage

5 months ago

ShemaleMovie

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05:17

Dudes first time anal bang-out with she-male

3 years ago

ShemaleTaxi

taxi, first time
15:34 83%

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

10 months ago

xHamster

compilation, asian, solo, masturbation, first time, shemale
11:56 43%

First Time With TS

8 years ago

ShemaleZ

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29:36

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8 years ago

AShemaleTube

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05:40

Blondes and psychedelic hump (Part 1) Remastered - Toon

Today

TrannyGem

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25:21

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

Yesterday

$$ FapHouse

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02:28

First Time CD ecperience

5 years ago

xHamster

first time
04:00

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

9 years ago

TXXX

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04:00 67%

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

9 years ago

TXXX

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14:20

My Very First Time With A sheboy Was Awesome

5 years ago

TrannyGem

first time
20:47

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3 years ago

TrannyOne

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05:09

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3 years ago

TrannyOne

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11:35 67%

First-Ever Time sextoy man-cream For T-hottie Moxxi Mewws

4 years ago

TrannyGem

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14:17

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4 years ago

xHamster

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08:11

His first time sex with a Tgirl is perfect!

12 years ago

AShemaleTube

first time
08:12

Fucking the Beautiful Adhara's Tight Ass for the First Time

10 months ago

xHamster

shemale, first time
08:32

Nerdy shemale Tastes manhood for the very first Time

3 years ago

ShemaleTaxi

first time
08:13

A Bride on Her Wedding Night �� futanari mother Breed Her youngster FemBoyfriend.

Today

ShemaleMovie

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