SHEMALE • FIRST TIME 4,695 videos

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12:47 93%

Ladyboystar - Changing sex positions while buttfuck drilling a mind-blowing ladyboy

2 months ago

ShemaleTaxi

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09:44 93%

Futanari doe visits Fira for a wild breeding lesson in Centaur Things

10 months ago

XXXVogue

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09:47 92%

MILF Stepmom Let Stepsons TS GF Fuck Her Asshole

10 months ago

BeMyHole

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10:12 92%

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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07:32 91%

Futanari stepdaughter has her first anal time with her horny mommy [Hentai Uncensored]

2 years ago

MyLust

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09:46 91%

LIL Young Transgirl Sissy gets RODE by wall plaything for the VERY FIRST TIME

2 years ago

TrannyGem

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06:06 91%

Whats Russian For Suck My Cock? First Time Girl Fucked By Ts Teacher - Lora Hoffman

7 months ago

ShemaleZ

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20:33 90%

My first time getting dominated by a hot blonde trans babe

9 months ago

XXXVogue

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16:00 90%

Femdom Ts Initiation: First Time Fuckers

5 years ago

ShemaleZ

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10:46 90%

Transexual Brandy Alexander gets fucked and facialized for the first time

7 years ago

ShemaleZ

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05:55 90%

Premiere: Ashley Is Fucked By A Shemale And Swallows For The First Time Transsexual Sperm! 6 Min With Ashley Cumstar And Rosella Extrem

3 years ago

ShemaleZ

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03:06 89%

GROOBYGIRLS - Eris Jolie First Time Sexy Performance

2 years ago

TrannyGem

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10:57 89%

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

3 years ago

ShemaleTaxi

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20:04 89%

TGIRL POST-OP: Jenny Loves Her New Pussy Fucked

4 years ago

xHamster

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20:39 89%

Love anal, busty ts, ladyboy ass fuck

1 month ago

XXXVogue

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08:07 89%

Car Toon And 3d Animated - Shemale Stepsister Persuaded Stepbrother For Anal Sex For A Long Time, And The Guy Agreed To Take Her Small Dick. Then The Guy Liked It When He Was Fucked In The Ass For The First Time Futa On Male. 8 Min

1 year ago

ShemaleZ

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03:06 89%

FEMOUT XXX - Angel Monroe First Time To Exposed Her Goodies

2 years ago

AShemaleTube

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52:54 88%

Trans Vanessa Jhons welcome Gonzo first time double anal

5 years ago

TXXX

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33:58 88%

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

8 months ago

KeekAss

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17:56 87%

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

1 year ago

ShemaleMovie

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06:32 87%

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

3 years ago

ShemaleTaxi

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18:15 87%

FEMALE DOMINATION HANDBALLING ASSFUCKING INSTRUCTING PEGGING DOMINATRIX PREDOMINANCE FEMBOY

4 years ago

TrannyGem

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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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08:07 86%

I try my transsexual friends cock for the first time

2 years ago

PornDr

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05:43 86%

Cute Femboy Aroma and Lovely German Girl Amber Kawaii Having romp in school Uniforms

2 months ago

ShemaleTaxi

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29:36 86%

Teaching str8 young boy first time ladyboy experience

9 years ago

AShemaleTube

erotic, first time
30:27 86%

Skinny she-male gets insatiable anal fucked in the small ass

1 year ago

VideoSection

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31:25 86%

Adorable Femboy teen First-ever Time With BIG BLACK COCK

2 months ago

KeekAss

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20:43 85%

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

4 months ago

ShemaleMovie

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14:39 85%

Ride With A Beautiful & Wonderful Tranny Isabella Salvatore

1 year ago

BeMyHole

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18:24 85%

The very first time

3 years ago

AShemaleTube

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06:20 85%

Tgirl Emma Roses first time with a woman

2 years ago

KeekAss

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10:36 85%

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

2 years ago

KeekAss

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08:07 85%

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

1 year ago

TrannyGem

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28:18 85%

Amazing Roxxie Moth Gets Anal Bareback First Time

5 years ago

BeMyHole

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04:30 85%

Topping a guy friend for the first time!!!

5 years ago

TrannyOne

first time
07:37 84%

Cutiepii33quinn Gets Her Cherry Arse Nailed For Very First Time

11 months ago

PePorn

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05:08 84%

Dude for the first time gets shemales male stick

7 years ago

Analdin

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07:18 84%

Ebony transsexual Trea Rich gets filled up

9 months ago

XXXVogue

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32:51 84%

French tgirl : his first time with a sexy dicky girl

5 years ago

AShemaleTube

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05:00 83%

Post-Op Ladyboy Beauty Natty Fucked Bareback

2 years ago

BeMyHole

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03:06 83%

Grooby Girls featuring baby girls dildo xxx

10 months ago

PornHat

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19:12 83%

CD TRANSSEXUAL FIRST-EVER BIG BLACK COCK !! HE CAME INWARDS of Me TWO TIMES!!! WARM PUBLIC SISSY

4 years ago

TrannyGem

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13:24 83%

Petite tranny undresses for the first time and shows what a horny cock she has

3 years ago

xHamster

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06:15 83%

Straight guys first time to fuck tranny

3 years ago

TrannyOne

first time
19:39 83%

Horny Danish Boy - His First Time

9 months ago

BeMyHole

blowjob, anal, ass licking, danish, first time, hardcore
11:39 83%

I&m so ultra-kinky that I SISSYGASM hastily after making up my bitchy she-creature face for the very first time

4 years ago

TrannyGem

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07:18 83%

TGirl pummels Step Sister bum For The first Time

6 months ago

ShemaleMovie

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07:37 83%

First time in the Ass iwant a doggy style!

2 years ago

AShemaleTube

cumshot, amateur, first time
16:43 83%

Feels Like The First Time . . .

4 years ago

TrannyOne

skinny, first time, anal
15:18 83%

BEGINNER TRANSE ZUM ERSTEN MAL IN DEN ARSCH GEFICKT UND BESAMT ASS JOB

4 years ago

TrannyGem

german, bisexual, crossdresser, riding, nylon, slut, first time
14:58 83%

My first time with a trans girl !!

1 year ago

xHamster

amateur, homemade, teen (18+), shemale, bisexual, big ass, lingerie
32:17 83%

Helena Price - First Time With A Ladyboy Hd

5 years ago

ShemaleZ

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18:38 82%

Melissa Masters - Your Very First Time Trans Femdom GFE

9 months ago

DrTuber

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08:14 82%

Trans Taking an anal chastity

1 year ago

ShemaleMovie

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53:12 82%

First time anal couple sex blonde tgirl

7 years ago

AShemaleTube

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10:38 82%

My first-ever ever 3some!!!

1 year ago

ShemaleMovie

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15:34 82%

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

1 year ago

xHamster

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15:02 81%

Rail with a stunning and super-sexy trans Isabella Salvatore

6 months ago

TrannyGem

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12:29 81%

Shy Latino First Time With A Shemale

7 years ago

TXXX

shy, first time
07:18 81%

TGirl fucks Step sister booty For The First Time

1 year ago

VideoSection

tattoo, blonde, shemale, first time, beauty, prostitute
23:22 81%

Fucked for the First Time

5 years ago

BeMyHole

stockings, femdom, latex, anal, couple, dogging, panties
11:34 81%

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

3 years ago

AnySex

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09:39 81%

Brand Cutie Fucked By A Man For The First Time Ever With Pixie Pond And New Trans

4 months ago

HClips

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06:02 80%

Filipino Femboy Has First Time Bareback Anal Sex On Camera

5 years ago

ShemaleZ

filipina, first time, femboy
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
15:53 80%

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

11 months ago

ShemaleTaxi

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10:32 80%

First Time Having Sex with a GILF

2 weeks ago

$$ FapHouse

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17:21 80%

I Fuck A Tranny Girl For The First Time 4k

4 years ago

ShemaleZ

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04:50 80%

Inexperienced Teen Fuck My Ass For The First Time, Did He Cum Quickly?

3 years ago

BeMyHole

teen (18+), creampie, chubby, teen anal (18+), BBW, nipples, first time
14:48 80%

My internet buddy has intercourse for the first-ever TIME with a trans girl and his femboy friend gets all his CUM in his face

6 months ago

ShemaleMovie

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05:14 80%

A steaming mexican nymph Offers Her Anus to a Thick, Juicy Cock

3 months ago

VideoSection

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13:59 80%

TRANSFIXED - Whitney Wright Helps Hot Redhead Erica Cherry Explore New Pleasures On Their First Date

2 years ago

xHamster

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09:39 80%

My first time with a trans. Part 3. I fuck her nice ass

2 years ago

JizzBunker

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06:14 80%

Kinky sissy, kinky cum, ts girl

3 months ago

XXXVogue

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06:00 80%

First time anal bareback for this amateur teen ladyboy

6 years ago

AShemaleTube

small cock, asian, ladyboy, first time
12:15 80%

Hottest Tanned Ladyboy Loves Getting Fucked In High Heels

4 months ago

BeMyHole

POV, chubby, asian, ladyboy, dogging, facial, ass licking
08:00 80%

Its This Sissy Milkboys first-ever Time

1 year ago

ShemaleTaxi

3D, crossdresser, ass, anime, first time, hardcore
07:49 80%

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

2 years ago

BeMyHole

first time, 18, asian, uniform
23:45 80%

First-time solo webcam pleasure session

1 year ago

XXXVogue

first time, solo, amateur, big cock, webcam
14:15 80%

Beautiful shemale pounds the guys ass bareback for the first time

4 years ago

TrannyOne

first time
05:26 80%

White Tranny Trying BBC For First Time

7 years ago

ShemaleZ

first time
03:06 80%

Genevieves short skirt sex by Grooby Girls

10 months ago

PornHat

small cock, solo, cute, masturbation
12:26 80%

Ultra-Kinky Trans Nanny Requests To Watch Employeers BIG BLACK COCK

4 years ago

TrannyGem

BBC, first time
03:06 80%

Transgender scene with sultry fiancée from Grooby Girls

11 months ago

PornHat

feet, small cock, redhead, solo, nipples, glasses, masturbation
04:04 80%

Anal Fisting First Time

4 years ago

ShemaleZ

teen (18+), teen anal (18+), fisting, first time
08:09 79%

My very first time

4 years ago

TrannyOne

first time
09:30 79%

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

2 years ago

Upornia

asian, shemale, interracial, big cock, first time
39:11 79%

A nosey woman tries a shemales spunk-pump for the very first time

4 years ago

ShemaleTaxi

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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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09:02 78%

J want you to take me like this!

10 months ago

ShemaleTaxi

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15:26 78%

ADULT TIME - Best First Date Ever! Casey Calvert Gobbles Up T-Girl Leilani Li & Takes DEEP Creampie!

1 year ago

xHamster

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16:30 78%

Fancy womans small tits sex

7 months ago

PornHat

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03:01 78%

FEMOUT GONZO: Lemmis Very First Time!

4 years ago

KeekAss

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03:34 78%

Melissa Masters In Your Very First Time - Trans Femdom Gfe

11 months ago

Fuxxx

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06:26 78%

Trans Lesbians first-ever Time Together

3 years ago

ShemaleTaxi

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05:30 78%

Addiction Theropy pt. 11 - Scorching IG Model splattered all over my office with FUTA penis inwards her.

4 years ago

TrannyGem

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35:17 78%

The First Time Married To A Trans Girl

1 year ago

HClips

POV, lingerie, shemale and girl, bareback, first time, brunette
06:20 78%

Teen guy sucking tranny cock first time

5 years ago

TrannyOne

teen (18+), first time
15:03 77%

First time sucking dick? And swallowing my hottest patrons

12 months ago

IcePorn

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18:14 77%

Pure TABOO asian cherry Lulu Chu Gets ALIEN DICK DRAINED By Stepmom Penny Barber & Dr. Sophia Locke!

10 months ago

ShemaleMovie

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12:53 77%

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

9 months ago

TrannyGem

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05:14 77%

Trans has her first time with her step cousin

2 years ago

ShemaleTaxi

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15:15 77%

VERY FIRST TIME TRANSGENDER PLOWED IN BOOTY AND CREAMPIED

3 years ago

KeekAss

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04:31 77%

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

9 months ago

TrannyGem

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08:12 76%

My first time with a real shemale

2 years ago

XXXDan

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15:46 76%

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

1 year ago

ShemaleMovie

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16:12 76%

Stephie scarlet first time pegging a tgirl

3 years ago

IcePorn

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1:29:57 76%

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

3 years ago

xHamster

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10:08 75%

First Time Revealing My Face. College Girl Beauty in Black Pantyhose Got so Naughty When She Tried Her New Costume and Anal Plug

7 months ago

$$ FapHouse

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05:32 75%

Post-Op Thai Shemale Meiji Pussy Bareback

2 years ago

BeMyHole

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12:32 75%

Blair Glass first Time With a pulverize Machine

3 years ago

ShemaleMovie

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35:17 74%

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

5 months ago

$$ FapHouse

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39:01 74%

A curious woman tries a shemale's cock for the first time

4 years ago

xHamster

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04:20 74%

Old man partners daughter and tranny first time Alyssa Gets Her Way With

7 years ago

TXXX

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01:21 73%

Arab Femboy First Time Anal

5 years ago

AShemaleTube

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10:36 73%

My First Time With My New Ejaculating Fantasy Dildo

3 years ago

BeMyHole

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01:28 73%

Casting Guy First Time - Itzelxxx

2 years ago

TXXX

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07:34 73%

My very first Time in Winston-Salem, NC (TRANSSEXUAL PublicPrincess)

6 years ago

TrannyGem

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11:02 72%

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

9 months ago

KeekAss

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