SHEMALE • FIRST TIME 3,378 videos

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05:14 94%

First-ever time going knuckle deep in taut milky culo of nubile she-male

4 years ago

KeekAss

handjob, stockings, fisting, masturbation, blonde, toys, small tits
14:36 94%

2 old Crossdressers first time

3 years ago

TrannyOne

crossdresser, first time, lingerie, shemale
03:08 93%

Porking Crossdresser For The Very first time in my life

7 months ago

KeekAss

amateur, crossdresser, first time, anal, blowjob
05:55 92%

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

2 years ago

ShemaleZ

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05:01 92%

Tranny is trying Anal for the first time

6 years ago

AShemaleTube

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05:57 92%

My first time with a MILF

5 years ago

ShemaleZ

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20:04 92%

TGIRL POST-OP: Jenny Loves Her New Pussy Fucked

3 years ago

xHamster

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18:51 92%

Fucked by a man for the first time.

4 years ago

ShemaleZ

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44:17 91%

Kendall Penny - Southern Sass Submits For The First Time!

2 years ago

ShemaleZ

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01:43 91%

Sissy First Time Piss Drinking

9 months ago

AShemaleTube

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15:00 91%

Asian Tranny First-Time Fantasy part 1 - Sharnell Dupree

1 year ago

xHand

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07:32 91%

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

1 year ago

MyLust

mom, anal, big ass, MILF, orgasm, big cock, futanari
08:26 90%

TRANS NYMPH GETS HUMPED BY ANOTHER TRANS DAME FOR THE FIRST-EVER TIME

9 months ago

TrannyGem

big tits, facesitting, 18, shemale and girl, blonde, babe, small tits
13:18 90%

FAUX-COCK REVIEW: Handsome Filipina Trans Chick Attempts a 7 Inch Electrified Fake Penis for the First-Ever Time

2 years ago

KeekAss

masturbation, filipina, first time
05:13 90%

She fellates a thick FUTA salami for the very first time

1 year ago

TrannyGem

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03:06 89%

FEMOUT XXX - New Tgirl Called Rachel, Gorgeous And Amazing Masturbating

5 months ago

TrannyGem

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08:05 89%

Skinny Trans Teen Fany Menezes Tries The Machine for The First Time

1 year ago

TXXX

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03:03 88%

A Young Finnish Trans Gets Cock For The First Time

2 months ago

AShemaleTube

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11:35 88%

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

4 years ago

TrannyGem

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09:11 87%

Adorable eighteen Yr Elderly Teenie TGirl With Giant Bootie Entices Stud Into Fuckin Her

1 year ago

TrannyGem

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06:32 87%

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

1 year ago

ShemaleTaxi

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10:32 87%

First Time Bbc For Cute Ts

2 years ago

TXXX

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06:15 87%

Getting Dominated And Sucking Cock For The First Time Like A Little Slut With Facial 7 Min

2 years ago

ShemaleZ

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14:58 86%

My first time with a trans girl !!

4 months ago

xHamster

amateur, homemade, teen (18+), shemale, lingerie, shemale and girl, big cock
04:50 86%

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

1 year ago

BeMyHole

teen (18+), creampie, chubby, teen anal (18+), BBW, nipples, first time
29:01 86%

Ts Bianca (bibibratx) top for the first time with Cristiano

2 months ago

AShemaleTube

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19:52 86%

Shemale teen with big schlong lets stud shag her in the ass

1 month ago

ShemaleMovie

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08:42 86%

Redhead ladyboy Lily Demure crazy sex movie

1 year ago

XoZilla

facial, cum in mouth, first time, cum in ass
12:23 86%

So its your first-ever time with a trans doll (Wholesome Jerk Off Instructions)

4 years ago

KeekAss

doll, instruction, JOI, first time, jerking, webcam
18:53 86%

Made His First Time Memorable - Anastasia Penny

1 year ago

ShemaleZ

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25:54 86%

First time BBC

5 years ago

ShemaleZ

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16:00 85%

Femdom Ts Initiation: First Time Fuckers

4 years ago

ShemaleZ

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15:32 84%

Russian Femboy Fucks With Mistress For The First Time With A Huge Strapon Tied With A Chastity

3 years ago

ShemaleZ

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32:51 83%

French tgirl : his first time with a sexy dicky girl

3 years ago

AShemaleTube

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13:00 83%

Nur mit Gummi in den Arsch bitte

3 years ago

xHamster

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22:32 83%

First time BBC FTM Transman Ethan Hawk

3 years ago

xHamster

couple, BBC, first time, FTM
13:04 83%

She made me cum twice! first-ever time boinking Britney from Tantaly - Emily Adaire

1 year ago

ShemaleTaxi

stockings, shemale, german, solo, cumshot, big cock, first time
10:55 83%

His very first Time Coming to the Gullet Supermarket

5 years ago

TrannyGem

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21:39 83%

Jamie French And Erica Cherry Fuck For The First Time And They Fuck Hard! Ots764

4 years ago

TXXX

french, first time
18:15 83%

FEMALE DOMINATION HANDBALLING ASSFUCKING INSTRUCTING PEGGING DOMINATRIX PREDOMINANCE FEMBOY

3 years ago

TrannyGem

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06:26 83%

Trans Lesbians first-ever Time Together

2 years ago

ShemaleTaxi

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03:06 83%

FEMOUT XXX - Angel Monroe First Time To Exposed Her Goodies

11 months ago

AShemaleTube

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21:59 83%

Trans nailing a heterosexual stud for the first-ever time

1 year ago

TrannyGem

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16:42 83%

I Recently Acquired A Giant Tentacle Dildo, And In This Video I Use It For The First Time

1 year ago

BeMyHole

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53:12 82%

First time anal couple sex blonde tgirl

6 years ago

AShemaleTube

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32:17 82%

Helena Price - First Time With A Ladyboy Hd

3 years ago

ShemaleZ

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13:00 82%

Trans Verbal Demands -Elegant Look With Glove And Sweet Dress

2 years ago

xHamster

cute, gloves, dress, first time
06:25 82%

Holy hell, what a super hot threesome with cougar Dee Williams. This is the very first time that Ellas met Dr. Williams and they are understandably a bit nervous. Dr. Williams do everything she can to put Ella at ease

3 years ago

ShemaleTaxi

teen (18+), blowjob, threesome, teen anal (18+), cougar, deepthroat, taxi
18:50 82%

AUBREYS FIRST-EVER TIME

4 years ago

TrannyGem

shemale, first time
16:43 82%

Feels Like The First Time . . .

3 years ago

TrannyOne

skinny, first time
09:39 82%

My first-ever time with a trans. Part trio. I shag her rich donk

1 year ago

KeekAss

crossdresser, ass licking, first time
04:30 82%

Topping a guy friend for the first time!!!

3 years ago

TrannyOne

first time
02:49 81%

Gimp White Fellow Deep Throats Meatpipe Before Getting Destroyed By Serena Cocoa’s Lollipop For The First-Ever Time

1 year ago

KeekAss

ebony, first time, shemale fucks guy
08:07 81%

I try my transsexual friends cock for the first time

1 year ago

PornDr

handjob, beauty, shemale, blowjob, german, wife, cumshot
05:18 81%

Boy had first-ever time rectal with shemale

5 years ago

VideoSection

first time, hardcore
31:37 80%

Shy Couple first time shemale experience 2

5 years ago

AShemaleTube

couple, shy, first time
11:21 80%

First time with a

3 years ago

TrannyOne

first time, hardcore, amateur
23:22 80%

Fucked for the First Time

4 years ago

BeMyHole

femdom, latex, anal, dogging, panties, first time, shemale fucks guy
28:17 80%

My trans girlfriend fucks me for the first time. She loves how she fucks my ass

1 year ago

xHamster

homemade, ladyboy, first time, shemale fucks guy, latina, amateur
22:08 80%

Trans screwing a heterosexual boy for the first-ever time

7 months ago

ShemaleTaxi

amateur, homemade, shemale, blowjob, anal, BDSM, first time
12:00 80%

Naughty Michael Delray fucks tranny for the first time

1 year ago

YourLust

stockings, big cock, first time
16:12 80%

Stephie scarlet first time pegging a tgirl

1 year ago

IcePorn

pegging, first time, amateur
03:12 80%

Crossdresser Fucks Uncle for First Time

6 years ago

ShemaleZ

uncle, first time, crossdresser
12:08 80%

My First Time With A Trans

2 years ago

BeMyHole

amateur, big tits, ass licking, first time, hardcore
03:06 80%

GROOBYGIRLS - Blonde Tgirl with pink nipples masturbates

6 months ago

TrannyGem

blonde, feet, solo, shemale, masturbation, nipples
06:54 79%

Getting dominated and sucking cock for the first time like a little slut with facial

2 years ago

TrannyOne

small cock, facial, slut, small tits, first time, domination
06:16 79%

Brunette trans with a monster cock Blacksharon jerks off very hot and makes his balls bounce to the rhythm of her masturbation

1 year ago

JizzBunker

ebony, orgasm, solo, monster, first time, thai
09:30 79%

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

7 months ago

Upornia

asian, shemale, interracial, big cock, first time
03:06 79%

FEMOUT XXX - Ashley Scarlett First Time Solo Masturbation

10 months ago

TrannyGem

cute, emo, solo, strip, masturbation, small tits, puffy nipples
18:19 78%

Barbie Femmes Dont Need A Ken. They Have Their Own Peckers

10 months ago

TrannyGem

teen (18+), shemale, creampie, 18, shemale and girl, cumshot, masturbation
28:10 78%

My Trans Girlfriend Fucks Me For The First Time. She I Love How She Fucks My Ass

1 year ago

ShemaleZ

amateur, redhead, girlfriend, first time
06:11 78%

Ladyboy Thippy & Noi first time 3 some

6 years ago

TXXX

ladyboy, gangbang, first time
02:57 78%

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

5 months ago

AnySex

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06:00 78%

First time anal bareback for this amateur teen ladyboy

5 years ago

AShemaleTube

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17:21 78%

I Fuck A Tranny Girl For The First Time 4k

2 years ago

ShemaleZ

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17:52 78%

Lady sextasy experiences transgender intense fucking for the first time also enjoys it

3 years ago

TrannyOne

first time, hardcore
14:51 77%

Sophie & Quinns Very First Time

3 years ago

KeekAss

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02:00 76%

My first time with a BBC

11 months ago

TrannyOne

anal, BBC, amateur, first time
03:53 76%

Old man first time with shemale

5 months ago

AShemaleTube

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11:09 76%

My First Time With A Shemale From Tantaly - Lina Paige

2 years ago

HClips

german, toys, first time
18:23 75%

Barbie Girls Don't Need A Ken. They Have Their Own Dicks

10 months ago

xHamster

teen (18+), blowjob, shemale and girl, cumshot, first time, creampie
11:51 75%

Direct Trans Creampie?! My First Time with Gianinats!!!

2 weeks ago

$$ FapHouse

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06:14 75%

First time with a Shemale Escort

5 years ago

AShemaleTube

mature, lingerie, first time, escort, latina
06:05 75%

Your First Time Getting Fucked By A Trans Girl: First Date Gfe Pov Femdom

1 year ago

ShemaleZ

femdom, shemale and girl, webcam, first time, solo, POV
17:26 75%

Alexandra Bxl In Young Guy Fucked In The Ass For The First Time By A Tranny

4 years ago

ShemaleZ

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05:32 75%

Post-Op Thai Shemale Meiji Pussy Bareback

1 year ago

BeMyHole

shemale, creampie, asian, first time, post op
15:51 75%

ADULT TIME - Straight Girl Kenzie Taylor First Trans Fuck With Big Titty T-Girl Brittney Kad

8 months ago

AShemaleTube

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06:15 75%

Marilyn Johnson first time to blow shemale meaty cock

3 years ago

AShemaleTube

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06:00 75%

Latina teen shemale first time fucked her girlfriend

7 years ago

AShemaleTube

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04:04 74%

Anal Fisting First Time

3 years ago

ShemaleZ

teen (18+), teen anal (18+), fisting, first time
08:19 74%

First Time Taste Drink My Own Cum. Handjob And Double Cum

1 year ago

xHamster

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10:00 74%

Boy first time with tranny

13 years ago

xHamster

first time
21:06 74%

Hot guy gets his ass plowed for the first time by a nasty shemale beauty

3 years ago

TrannyOne

first time, beauty
06:02 74%

Filipino Femboy Has First Time Bareback Anal Sex On Camera

4 years ago

ShemaleZ

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30:46 74%

Jamie French And Bambi Bliss - First Time Ots846

3 years ago

ShemaleZ

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08:00 73%

741m584-g02 My Son Who Came Back For The First Time In

1 year ago

GetTranny

hairy, japanese, first time
18:49 73%

Unseen Hook-Up Movies Cumpilation - Onlyfans Veronica Sanders

1 year ago

TrannyGem

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08:09 73%

My very first time

3 years ago

TrannyOne

first time
08:01 73%

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3 years ago

TrannyOne

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37:57 73%

Sexy traps first Video

3 years ago

XXXDan

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05:07 73%

Dude for the fist time has tranny up his rear

6 years ago

XoZilla

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06:15 73%

Spencer Bradley first time to suck a tranny cock

3 years ago

AShemaleTube

first time, shemale and girl
08:58 72%

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9 months ago

AShemaleTube

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24:59 72%

Old Futa Girl-On-Girl Tranny Humps Young Very First Time Cherry With Numerous Ejaculations - Sims four

1 year ago

TrannyGem

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04:18 72%

Mia Thorne Trains Cherry Tgirl Mate How to Have Hook-Up UTTER MOVIE ON FANSLY

1 year ago

TrannyGem

amateur, small cock, shemale, lesbian, shemale and girl, first time
03:23 71%

First Time Fucked by a Shemale

5 years ago

ShemaleZ

18, first time
15:00 71%

Lustful shemale incredible porn movie

1 year ago

XoZilla

small cock, shemale, first time, missionary
13:16 71%

ADULT TIME - Curious Cis Couple Have Their First Threesome With Trans Baddie Kasey Kei!

2 years ago

TXXX

threesome, couple, first time
01:21 71%

Mirans First Time

1 year ago

TXXX

first time, mature
09:08 71%

Tatted Guys First Time With a Trans damsel: Blows His geyser and His Mind over a Smoking oral pleasure

7 months ago

ShemaleTaxi

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08:10 70%

Transsexual Kim Wagner ravaged a teenage +18 guy

2 weeks ago

ShemaleMovie

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10:36 70%

My First Time With My New Ejaculating Fantasy Dildo

1 year ago

BeMyHole

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36:43 70%

Very first time with my Hismith machine

3 years ago

ShemaleTaxi

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06:15 69%

Shemale fucked guy for the first time and she enjoyed hardcore anal sex

1 year ago

AShemaleTube

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10:13 69%

Real Transgender Gal Gets Ass-Fuck Smash

1 year ago

TrannyGem

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01:21 67%

Arab Femboy First Time Anal

4 years ago

AShemaleTube

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10:28 67%

Boy very first time with trans

4 years ago

HDSex

first time
07:42 67%

He Wears My Panties For The First Time Pov - Teaser Video

1 year ago

GetTranny

panties, first time
20:09 67%

First Time Working Out With New Gym Buddy Fucks New Tantaly - Emily Adaire And Lina Paige

3 months ago

HClips

solo, first time, amateur, shemale, gym
38:29 67%

Moscardiniema - I Remember The First Time I Saw Manu On Social Media, I Was Laying In Bed And It Was About 11pm, I Literally Couldnt Believe My Eyes.

1 year ago

BeMyHole

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