SHEMALE • FIRST TIME 4,584 videos

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09:44 94%

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

8 months ago

XXXVogue

cartoon, futanari, cumshot, first time, creampie, anal, shemale
09:47 93%

MILF Stepmom Let Stepsons TS GF Fuck Her Asshole

8 months ago

BeMyHole

mom, blowjob, anal, big ass, MILF, ladyboy, ass licking
07:32 91%

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

2 years ago

MyLust

mom, anal, MILF, orgasm, futanari, first time
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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06:06 91%

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

4 months ago

ShemaleZ

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20:33 91%

My first time getting dominated by a hot blonde trans babe

7 months ago

XXXVogue

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20:04 91%

TGIRL POST-OP: Jenny Loves Her New Pussy Fucked

4 years ago

xHamster

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09:46 90%

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

2 years ago

TrannyGem

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10:46 90%

Transexual Brandy Alexander gets fucked and facialized for the first time

7 years ago

ShemaleZ

facial, first time
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

3 years ago

ShemaleTaxi

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16:00 90%

Femdom Ts Initiation: First Time Fuckers

5 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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07:37 89%

Cutiepii33quinn Gets Her Cherry Arse Nailed For Very First Time

8 months ago

PePorn

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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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05:55 89%

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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20:43 88%

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

2 months ago

ShemaleMovie

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52:54 88%

Trans Vanessa Jhons welcome Gonzo first time double anal

5 years ago

TXXX

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08:07 88%

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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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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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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14:39 86%

Ride With A Beautiful & Wonderful Tranny Isabella Salvatore

11 months ago

BeMyHole

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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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05:00 86%

Post-Op Ladyboy Beauty Natty Fucked Bareback

2 years ago

BeMyHole

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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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33:58 86%

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

5 months ago

KeekAss

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18:15 86%

FEMALE DOMINATION HANDBALLING ASSFUCKING INSTRUCTING PEGGING DOMINATRIX PREDOMINANCE FEMBOY

4 years ago

TrannyGem

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06:20 85%

Tgirl Emma Roses first time with a woman

1 year ago

KeekAss

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05:08 85%

Dude for the first time gets shemales male stick

7 years ago

Analdin

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17:56 85%

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

10 months ago

ShemaleMovie

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18:24 85%

The very first time

2 years ago

AShemaleTube

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14:58 84%

My first time with a trans girl !!

1 year ago

xHamster

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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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04:30 84%

Topping a guy friend for the first time!!!

5 years ago

TrannyOne

first time
28:18 83%

Amazing Roxxie Moth Gets Anal Bareback First Time

5 years ago

BeMyHole

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12:08 83%

My First Time With A Trans

3 years ago

BeMyHole

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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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19:39 83%

Horny Danish Boy - His First Time

6 months ago

BeMyHole

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07:37 83%

First time in the Ass iwant a doggy style!

1 year ago

AShemaleTube

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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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15:18 83%

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

4 years ago

TrannyGem

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53:12 83%

First time anal couple sex blonde tgirl

7 years ago

AShemaleTube

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32:17 83%

Helena Price - First Time With A Ladyboy Hd

4 years ago

ShemaleZ

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07:18 82%

Ebony transsexual Trea Rich gets filled up

7 months ago

XXXVogue

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08:07 82%

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

1 year ago

TrannyGem

cumshot, first time, creampie, old man, german, old and young (18+)
16:43 82%

Feels Like The First Time . . .

4 years ago

TrannyOne

skinny, first time, anal
08:14 81%

Trans Taking an anal chastity

1 year ago

ShemaleMovie

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15:53 81%

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

8 months ago

ShemaleTaxi

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08:12 81%

My first time with a real shemale

2 years ago

XXXDan

brazil, orgasm, facial, 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
11:34 81%

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

3 years ago

AnySex

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02:57 80%

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

1 year ago

AnySex

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23:22 80%

Fucked for the First Time

5 years ago

BeMyHole

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17:21 80%

I Fuck A Tranny Girl For The First Time 4k

3 years ago

ShemaleZ

big ass, big tits, shemale and girl, first time, anal orgasm, brunette
06:14 80%

Kinky sissy, kinky cum, ts girl

2 weeks ago

XXXVogue

first time, shemale and girl, sissy, stockings
19:12 80%

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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07:18 80%

TGirl pummels Step Sister bum For The first Time

3 months ago

ShemaleMovie

shemale, amateur, big ass, beauty, first time, prostitute
07:18 80%

TGirl fucks Step sister booty For The First Time

1 year ago

VideoSection

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12:15 80%

Hottest Tanned Ladyboy Loves Getting Fucked In High Heels

2 months ago

BeMyHole

POV, chubby, asian, ladyboy, dogging, facial, ass licking
06:15 80%

Straight guys first time to fuck tranny

3 years ago

TrannyOne

first time
06:00 80%

First time anal bareback for this amateur teen ladyboy

6 years ago

AShemaleTube

small cock, asian, ladyboy, first time
09:39 80%

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

2 years ago

JizzBunker

teen (18+), teen anal (18+), latina, first time, couple, amateur
07:49 80%

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

2 years ago

BeMyHole

first time, 18, asian, uniform
03:12 80%

Crossdresser Fucks Uncle for First Time

7 years ago

ShemaleZ

uncle, first time, crossdresser
23:45 80%

First-time solo webcam pleasure session

10 months 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
03:06 80%

Genevieves short skirt sex by Grooby Girls

7 months ago

PornHat

small cock, solo, cute, masturbation
05:26 80%

White Tranny Trying BBC For First Time

7 years ago

ShemaleZ

first time
12:26 80%

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

4 years ago

TrannyGem

BBC, first time
04:50 80%

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

2 years ago

BeMyHole

teen (18+), creampie, chubby, teen anal (18+), BBW, nipples, first time
06:02 79%

Filipino Femboy Has First Time Bareback Anal Sex On Camera

5 years ago

ShemaleZ

filipina, first time, femboy
13:59 79%

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

2 years ago

xHamster

shemale, shemale and girl, first time
05:48 79%

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

4 months ago

HClips

shemale fucks guy, teen (18+), asian, amateur, ladyboy, first time
12:29 79%

Shy Latino First Time With A Shemale

6 years ago

TXXX

shy, first time
15:02 79%

Rail with a stunning and super-sexy trans Isabella Salvatore

3 months ago

TrannyGem

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11:02 79%

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

7 months ago

KeekAss

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39:11 79%

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

4 years ago

ShemaleTaxi

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08:09 79%

My very first time

4 years ago

TrannyOne

first time
04:04 79%

Anal Fisting First Time

4 years ago

ShemaleZ

teen (18+), teen anal (18+), fisting, first time
15:21 79%

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

1 year ago

SomePorn

blowjob, dogging, ass licking, cumshot, ass, deepthroat, reality
18:38 79%

Melissa Masters - Your Very First Time Trans Femdom GFE

7 months ago

DrTuber

femdom, solo, cumshot, ass, first time, big ass
09:30 79%

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
04:31 78%

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

7 months ago

TrannyGem

amateur, cute, shemale, creampie, anal, fetish, dogging
15:26 78%

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

1 year ago

xHamster

big ass, shemale and girl, shemale, first time, creampie
03:06 78%

Transgender scene with sultry fiancée from Grooby Girls

8 months ago

PornHat

feet, redhead, solo, nipples, glasses, masturbation, jeans
14:48 78%

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

3 months ago

ShemaleMovie

amateur, spanish, anal, threesome, couple, outdoor, orgasm
10:38 78%

My first-ever ever 3some!!!

11 months ago

ShemaleMovie

amateur, beauty, double anal, blonde, big cock, deepthroat, first time
35:17 78%

The First Time Married To A Trans Girl

1 year ago

HClips

POV, lingerie, shemale and girl, bareback, first time, brunette
06:26 78%

Trans Lesbians first-ever Time Together

3 years ago

ShemaleTaxi

shemale, lesbian, taxi, first time
10:57 77%

LEGACY MESS : Filipino Slut With ginormous Cock for the first time in pornography messy Fucks deep hard in the Throat and Ass of her Partner

11 months ago

ShemaleMovie

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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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09:02 77%

J want you to take me like this!

7 months ago

ShemaleTaxi

amateur, shemale, french, lingerie, solo, taxi, first time
09:39 76%

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

2 months ago

HClips

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16:12 76%

Stephie scarlet first time pegging a tgirl

2 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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16:30 76%

Fancy womans small tits sex

4 months ago

PornHat

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18:14 75%

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

7 months ago

ShemaleMovie

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05:32 75%

Post-Op Thai Shemale Meiji Pussy Bareback

2 years ago

BeMyHole

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06:20 75%

Teen guy sucking tranny cock first time

5 years ago

TrannyOne

teen (18+), first time
12:53 75%

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

7 months ago

TrannyGem

amateur, stockings, doll, german, cumshot, masturbation, nylon
03:34 75%

Melissa Masters In Your Very First Time - Trans Femdom Gfe

8 months ago

Fuxxx

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12:32 75%

Blair Glass first Time With a pulverize Machine

2 years ago

ShemaleMovie

glasses, machine, first time
01:21 75%

Arab Femboy First Time Anal

5 years ago

AShemaleTube

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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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35:17 74%

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

2 months ago

$$ FapHouse

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01:28 73%

Casting Guy First Time - Itzelxxx

2 years ago

TXXX

casting, first time
07:34 73%

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

5 years ago

TrannyGem

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10:36 73%

My First Time With My New Ejaculating Fantasy Dildo

3 years ago

BeMyHole

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04:20 72%

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

7 years ago

TXXX

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15:46 72%

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

1 year ago

ShemaleMovie

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09:37 72%

Coming Back From A Party, Lizzy Makes Me Very Naughty

1 year ago

BeMyHole

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12:05 71%

Beauty Fucks For Her First Time With A Trans And Its With Spencer Bradley

3 years ago

ShemaleZ

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06:40 71%

Lady with a rock hard lollipop rides step daddy

1 year ago

ShemaleTaxi

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06:08 71%

Curvy Black Trap Twerking and Tugging

7 years ago

TrannyGem

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4:12:46 71%

Oots-015 Sensitive Cosplayer Who Gets Her Anus Penetrated And Writhes In Agony. Anal Masturbation, Deep Throat, Sensitive, First Time Filming, Female Orgasm, Ahegao, Lesbian, Anal Sex, Lotion Play, Pov, Doujinshi, Cosplay, Cosplayer, Big Cock, 3p, Fa

1 year ago

ShemaleZ

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03:01 71%

FEMOUT GONZO: Lemmis Very First Time!

4 years ago

KeekAss

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36:34 71%

First time with my Hismith machine

4 years ago

TrannyOne

machine, first time, stockings
16:51 71%

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

1 year ago

HClips

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