SHEMALE • FIRST TIME 4,508 videos

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04:30 83%

Topping a guy friend for the first time!!!

4 years ago

TrannyOne

first time
07:37 89%

Cutiepii33quinn Gets Her Cherry Arse Nailed For Very First Time

8 months ago

PePorn

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08:12 81%

My first time with a real shemale

2 years ago

XXXDan

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05:48 78%

Straight Guy First Time To Fuck A Trans And First Time To Try A Lady Cock

3 months ago

HClips

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06:25 70%

Ladyboy Amy Fucks Guys Ass For The First Time

3 years ago

DrTuber

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23:44 63%

First-ever time for my hubby plow with Ladyboy

3 years ago

ShemaleTaxi

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10:12 91%

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

1 year ago

ShemaleZ

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14:56 57%

Domme T: first-ever Time rope-On Virgin

2 years ago

ShemaleTaxi

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08:07 86%

I try my transsexual friends cock for the first time

2 years ago

PornDr

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12:07 64%

You will never forget your first time with shemale babe Mel

9 years ago

xHamster

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08:00 57%

Christmas orgy first time Slumber Party

7 years ago

IcePorn

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10:36 73%

My First Time With My New Ejaculating Fantasy Dildo

2 years ago

BeMyHole

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05:08 85%

Dude for the first time gets shemales male stick

7 years ago

Analdin

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11:52 44%

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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16:30 67%

Teen shemale LOVES first time with boyfriend

10 years ago

TXXX

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35:17 69%

All Natural Beauties Nico Love & Claire Gemini in First Time Trans Threesome

1 month ago

$$ FapHouse

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10:28 72%

Boy very first time with trans

5 years ago

HDSex

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51:27 68%

Little ones first time - all 3 angles

6 years ago

TXXX

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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 79%

My very first time

4 years ago

TrannyOne

first time
11:34 81%

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

3 years ago

AnySex

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32:17 83%

Helena Price - First Time With A Ladyboy Hd

4 years ago

ShemaleZ

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05:40

Male s first time with transgender

1 week ago

AShemaleTube

shemale, first time
01:28 73%

Casting Guy First Time - Itzelxxx

2 years ago

TXXX

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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

asian, shemale, interracial, big cock, first time
07:18 80%

TGirl fucks Step sister booty For The First Time

1 year ago

VideoSection

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05:55

Straight Guy First Time to Fuck a Trans and First Time to Try a Lady Cock

3 months ago

$$ FapHouse

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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.

1 year ago

TrannyGem

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03:34 75%

Melissa Masters In Your Very First Time - Trans Femdom Gfe

7 months ago

Fuxxx

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15:53 83%

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

7 months ago

ShemaleTaxi

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09:47 93%

MILF Stepmom Let Stepsons TS GF Fuck Her Asshole

7 months ago

BeMyHole

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08:01

Its the first time you show me your cock

Today

AShemaleTube

big cock, first time
16:02 60%

ADULT TIME - Bored Lulu Chu DARED To Get First Creampie From T-Girl Zariah Aura During Power Outage!: Trans Porn

3 months ago

JizzBunker

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04:58

Tranny First Time With A Huge Cock

1 year ago

ShemaleZ

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10:36 86%

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

2 years ago

KeekAss

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15:03 69%

First time sucking dick? And swallowing my hottest patrons

8 months ago

IcePorn

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05:17 55%

Cd and Str8 First time

7 years ago

TXXX

first time
06:15 80%

Straight guys first time to fuck tranny

3 years ago

TrannyOne

first time
12:29 79%

Shy Latino First Time With A Shemale

6 years ago

TXXX

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23:22 80%

Fucked for the First Time

5 years ago

BeMyHole

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05:39

Beautiful Trans Babe Anal Her Bestie For The First Time With Tori Easton And Jade Venus

Yesterday

ShemaleZ

redhead, shemale
08:12 67%

My first time with a tranny

2 years ago

xHamster

first time
14:34

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

5 months ago

TrannyOne

shemale, first time
09:37 72%

Coming Back From A Party, Lizzy Makes Me Very Naughty

1 year ago

BeMyHole

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08:05 58%

My very first time hilting the Artemis 115

1 month ago

ShemaleMovie

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06:40 71%

Lady with a rock hard lollipop rides step daddy

1 year ago

ShemaleTaxi

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54:28 68%

Sultry Fucking Anal Bareback Hoss Kado Ariel Demure gigantic Dick Sexy Trans girl Multiple Cumshots Creampie

1 month ago

ShemaleMovie

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16:40 65%

Perola Martinez gives it to the guy for the first time

9 months ago

XXXVogue

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15:57

The first time

2 years ago

AShemaleTube

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05:25

Amateur Crossdress Madison CD drips cum from fet lil clit onto a faux-cock and then fellates the dildo like the slut she is

Yesterday

ShemaleMovie

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03:06 78%

Transgender scene with sultry fiancée from Grooby Girls

8 months ago

PornHat

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13:25

His very first time with a ladyboy

8 years ago

HDSex

asian, nylon, first time
05:08

All congenital Beauties Nico Love & Claire Gemini in first Time Trans three way

2 weeks ago

ShemaleTaxi

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14:15 80%

Beautiful shemale pounds the guys ass bareback for the first time

4 years ago

TrannyOne

first time
02:57 80%

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
07:39 69%

Trap Schoolgirl Anal For The First Time

6 years ago

TrannyOne

first time
08:10 67%

Milf plumbs teen with wire on very first time Risky Birthday Capers

8 months ago

ShemaleTaxi

teen (18+), MILF, first time
04:31 78%

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

6 months ago

TrannyGem

amateur, cute, shemale, creampie, anal, fetish, dogging
25:38

Sisters, uncensored, rough-sex

Today

XXXVogue

skinny, 18
07:14

3d fuck, big ass femboy, beautiful lady boy

6 days ago

XXXVogue

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10:46

Latina teenager legal yr elder transgender princess gets raunchy orgy for the very first time

1 week ago

TrannyGem

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08:14

My first-ever time with a ladyboy

8 months ago

ShemaleMovie

ladyboy, first time
07:19 56%

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

5 years ago

ShemaleTaxi

taxi, first time
07:18 80%

TGirl pummels Step Sister bum For The first Time

3 months ago

ShemaleMovie

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14:58 84%

My first time with a trans girl !!

1 year ago

xHamster

amateur, homemade, teen (18+), shemale, bisexual, lingerie, shemale and girl
07:37 83%

First time in the Ass iwant a doggy style!

1 year ago

AShemaleTube

cumshot, amateur, 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
08:14

Venezuelan, femboy anal, guy fucks shemale

Yesterday

XXXVogue

teen anal (18+), thai, sissy, femboy, beauty, anal, teen (18+)
20:43 88%

My first time dominated by scorching light-haired t-girl LaraMCX

1 month ago

ShemaleMovie

teen (18+), anal, teen anal (18+), BDSM, blonde, ass, cum in mouth
04:38

Dudes first time anal sex with shemale

6 years ago

ShemaleZ

first time
05:19

Sunshyne Monroes exciting first time in domination

4 months ago

XXXVogue

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22:53

Young dude Fucks Blonde Latin Shemale Anal for the first Time

1 month ago

ShemaleMovie

shemale fucks guy, first time, 18
17:07 63%

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

2 years ago

TrannyGem

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08:10

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

2 years ago

ShemaleTaxi

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05:33

19 Years elderly ultra-cute Sissy Judes conforms Her First Day in Gloryhole Handjob

1 week ago

ShemaleTaxi

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28:18 83%

Amazing Roxxie Moth Gets Anal Bareback First Time

5 years ago

BeMyHole

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05:00 63%

Ts gets blowjob first time Sneaking Around With Daddys partner

4 years ago

TrannyOne

first time
17:04 60%

Young Guy Fucks A Blonde Shemale In Her Tight Asshole For The First Time

4 months ago

ShemaleZ

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15:51 60%

Vol #8: boinked For The first Time on Femout

7 months ago

ShemaleTaxi

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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

1 year ago

ShemaleZ

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07:31 58%

Transgender mom, young petite, sissy feminization

1 month ago

XXXVogue

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10:41

First time trying a black cock

Today

AShemaleTube

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17:56 83%

Legacy Mess: bony transgender princess humps a guy for the first time. P2

10 months ago

ShemaleMovie

thai, couple, BDSM, ladyboy, domination, skinny, first time
08:14 81%

Trans Taking an anal chastity

1 year ago

ShemaleMovie

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18:24 86%

The very first time

2 years ago

AShemaleTube

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06:36

Cute femboy, futanari animation, trans

Yesterday

XXXVogue

femboy, cartoon
06:20 75%

Teen guy sucking tranny cock first time

4 years ago

TrannyOne

teen (18+), first time
06:32 86%

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

3 years ago

ShemaleTaxi

femdom, asian, filipina, domination, first time, kissing
08:00 67%

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
09:02 76%

J want you to take me like this!

7 months ago

ShemaleTaxi

amateur, shemale, french, lingerie, solo, taxi, first time
10:38 78%

My first-ever ever 3some!!!

10 months ago

ShemaleMovie

amateur, beauty, double anal, blonde, big cock, deepthroat, first time
06:24

Redhead Trans gal fucks lezzy for the first time

Today

HDSex

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14:39 86%

Ride With A Beautiful & Wonderful Tranny Isabella Salvatore

11 months ago

BeMyHole

beauty, public, big tits, car, 18, jerking, riding
12:25

Ladyboystar - Hard-core sans a condom bumfuck orgy with a killer transgender princess

2 days ago

TrannyGem

dogging, creampie, anal, ladyboy, asian, amateur, POV
08:08 60%

My very first time

8 years ago

xHamster

anal, first time, shemale fucks guy
04:00

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

10 years ago

TXXX

girlfriend, first time
06:34 50%

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

2 years ago

BeMyHole

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16:08

Guy enjoys first time with busty shemale

5 months ago

XXXVogue

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08:42 50%

First time getting ass fucked

4 months ago

XXXVogue

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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
29:59 87%

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

3 years ago

Upornia

MILF, shemale and girl, cumshot, sissy, first time
10:12

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

7 months ago

ShemaleZ

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07:37

Cutiepii33quinn gets her cherry arse nailed for very first time

4 years ago

TrannyGem

first time
10:05

Dorian Drake gets barebacked for the very first time by giant dick from trans doll pv

3 months ago

KeekAss

amateur, shemale, bareback, first time
06:50

Beautiful Local Girl Hardcore sex with Bf for the First time

8 years ago

AShemaleTube

first time
01:21 75%

Arab Femboy First Time Anal

5 years ago

AShemaleTube

homemade, arab, first time, femboy, domination
10:43 66%

Girl tries to fuck with trans first time

6 years ago

AShemaleTube

first time, homemade
10:51 50%

My step-dad CATCHES me drilling my bf

10 months ago

ShemaleMovie

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21:45 60%

Guy first time with blonde Tgirl

15 years ago

AShemaleTube

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10:15 56%

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

2 years ago

ShemaleTaxi

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16:19

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

4 years ago

TrannyGem

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33:58 86%

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

4 months ago

KeekAss

handjob, shemale, first time
28:33

Ts first time, trans anal sex, rectal

2 days ago

XXXVogue

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04:00 69%

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

10 years ago

TXXX

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29:36 86%

Teaching str8 young boy first time ladyboy experience

9 years ago

AShemaleTube

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15:21 79%

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

1 year ago

SomePorn

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11:11

First time stepbrother

2 years ago

ShemaleMovie

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07:49 80%

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

2 years ago

BeMyHole

first time, 18, asian, uniform
06:14

Young Guy Picks up a Trans woman for a Really Good shag and Ends up Fucking Her Hard While His wife Is at Work

Yesterday

ShemaleMovie

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