SHEMALE • FIRST TIME 4,695 videos

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04:00

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

10 years ago

TXXX

girlfriend, first time
07:49 80%

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

2 years ago

BeMyHole

first time, 18, asian, uniform
11:11

First time stepbrother

2 years ago

ShemaleMovie

blowjob, femboy, homemade, seduced, first time
38:26

OMG – only after she pulled her pants down did he know she had a dick

5 years ago

xHamster

MILF, orgasm, nipples, natural, cum in mouth, first time
05:17

Dudes first time anal bang-out with she-male

4 years ago

ShemaleTaxi

taxi, first time
15:34 82%

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

1 year ago

xHamster

compilation, asian, solo, masturbation, first time, shemale
03:02

This is Allicia Nogueiras first time on our site and we

12 years ago

DrTuber

first time
22:54

His First Time With A shetwink

8 years ago

ShemaleZ

first time
08:14 82%

Trans Taking an anal chastity

1 year ago

ShemaleMovie

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11:56 43%

First Time With TS

9 years ago

ShemaleZ

vintage, first time
08:07 85%

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+)
04:00 57%

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

12 years ago

TXXX

russian, shemale and girl, teacher, first time
06:38

My first time with a meaty trouser snake tgirl

1 year ago

ShemaleTaxi

shemale, shemale fucks guy, first time
1:58:01 54%

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

1 year ago

ShemaleZ

lingerie, shemale, asian, first time, swallow
22:46 53%

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

4 years ago

TrannyOne

feet, ass to mouth, cum in mouth, sissy, first time, cum in ass
10:46 90%

Transexual Brandy Alexander gets fucked and facialized for the first time

7 years ago

ShemaleZ

facial, first time
08:00

Anastasia Penny Made His First Time Memorable

2 years ago

GetTranny

cumshot, first time
33:22

His first time with a shemale

1 year ago

XXXDan

MILF, BDSM, vintage, teacher, first time, hardcore
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, deepthroat, reality, first time, romantic
09:28

Teen Thug first time with Tranny

7 years ago

ShemaleZ

first time
06:27

Cute ladyboy's first time

8 years ago

AShemaleTube

first time
06:15

Shemale first time sex with a guy

6 years ago

AShemaleTube

first time
05:30

My First Time With Beautyfull Shemale 6 Min

3 years ago

ShemaleZ

first time
15:37

First Time Eating Ass

4 years ago

Upornia

first time
12:27

My first time.

2 weeks ago

AShemaleTube

big ass, interracial, homemade, shemale, first time
08:01

Teen first time screaming which will probably be the thickest thing sh

4 years ago

TrannyOne

screaming, first time, teen (18+)
24:16 64%

Dominant blonde t-girl wrecks her guy toy

10 months ago

XXXVogue

kissing, shemale, anal, BDSM, blonde, deepthroat, cum in mouth
11:36

Crossdresser CD Blows Straight Boy first Time Candicane

3 years ago

TrannyOne

first time, crossdresser
10:12

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

11 months ago

ShemaleZ

cum in mouth, first time, big ass, cum in ass
24:04 67%

My first-ever time with a damsel, what a elation, hookup bareback!

3 months ago

TrannyGem

shemale, POV, brazil, tattoo, 18, bareback, skinny
16:08

Guy enjoys first time with busty shemale

9 months ago

XXXVogue

amateur, cumshot, big cock, ass, first time, shemale fucks guy
16:11 66%

FtM Youngster Wants Ass Fucking

9 months ago

TrannyGem

amateur, teen (18+), POV, teen anal (18+), orgasm, british, ass
10:51 50%

My step-dad CATCHES me drilling my bf

1 year ago

ShemaleMovie

facial, caught, cum in mouth, first time, boyfriend, cum in ass
07:43

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

10 months ago

XXXVogue

teen anal (18+), femboy, teen (18+), first time, shemale
14:17

Is this your first time in a shemale gangbang

4 years ago

xHamster

first time
08:12 53%

Skinny teen femboy getting fucked first time

1 year ago

xHamster

german, crossdresser, skinny, sissy, first time, femboy
10:36 57%

VERY FIRST TIME WITH A TRANS - LUANA PRADO

2 months ago

TrannyGem

couple, amateur, shemale, first time, creampie
06:33

Very Small Cock Dickgirl Fucks For The First Time

3 years ago

TrannyOne

small cock, first time
05:00 63%

Ts gets blowjob first time Sneaking Around With Daddys partner

4 years ago

TrannyOne

first time
29:59 86%

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
08:32

Nerdy shemale Tastes manhood for the very first Time

4 years ago

ShemaleTaxi

first time
08:59

First Time swallowing cum

4 years ago

TrannyOne

swallow, first time
04:52

Shaved Cock And Ass The Date - His First Time Discovering His GirlFriend Has A HUGE COCK, Part 2

4 years ago

TrannyOne

ebony, black, girlfriend, shaving, first time
10:14

Virgin shemale with a large, thick penis and a big butt having sex for the first time.

2 weeks ago

AShemaleTube

penis, solo, interracial, first time
14:39 85%

Ride With A Beautiful & Wonderful Tranny Isabella Salvatore

1 year ago

BeMyHole

beauty, public, big tits, car, 18, jerking, riding
12:42 67%

The nylon fetish pt2 Sissy guy first time penetrate ladyboy

1 year ago

ShemaleMovie

fetish, lingerie, BDSM, 3D, nylon, gape, first time
36:33

Carolina Biondi Trans Active Shooting For The First Time

1 year ago

ShemaleZ

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04:08

Sucking Off Str8 guy in parking lot. It was his first time

7 years ago

ShemaleZ

fetish, first time
05:08

Alluring shemale first time butt fucked

3 years ago

TrannyOne

18, first time
29:19 64%

The first Time Kisses Came Upon Rio

7 years ago

TXXX

kissing, first time, amateur, webcam
05:09

Dude had first time anal with shemale

4 years ago

TrannyOne

first time
05:15

Shemales donk acquires poked stiff

1 year ago

ShemaleMovie

big cock, first time
14:40

Now is your first time: Blowjob, Amateur Babe Porn

11 months ago

XXXDan

first time, asian, cumshot, missionary
03:01 58%

FEMOUT: Ms. Momo's First Time

4 years ago

xHamster

beauty, small cock, asian, solo, first time
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

bisexual, orgasm, japanese, cum in mouth, first time
08:11

His first time sex with a Tgirl is perfect!

13 years ago

AShemaleTube

first time
05:01

VRB TRANS First Time TS Call Girl Experience

6 years ago

xHamster

first time, lingerie
32:23

JoJo Havana First-Ever Time non-pro Comes In Porno With A group sex

6 years ago

TrannyGem

group, first time
02:28

First Time CD ecperience

5 years ago

xHamster

first time
04:00 43%

Dorm Room First Times Emma Kisses Her first Girl AND Sucks her Cock

12 years ago

TXXX

kissing, dorm, first time
06:14

Transsexual Bronx Takes What She Wants

5 months ago

ShemaleMovie

anal, shemale fucks guy, first time, black
32:51 83%

French tgirl : his first time with a sexy dicky girl

5 years ago

AShemaleTube

french, outdoor, ass to mouth, shemale and girl, blonde, first time
02:37

My first time sucking a cock

3 years ago

TrannyOne

first time
08:12

We Met for The First Time with This Married Handsome Man and We Both Went Beyond Borders

3 years ago

xHamster

amateur, cum in mouth, first time, cum in ass
10:43 66%

Girl tries to fuck with trans first time

7 years ago

AShemaleTube

first time, homemade
10:46

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

3 months ago

TrannyGem

homemade, anal, amateur, first time, latina
09:41

My First Time With A Trans. Part 3. I Fuck Her Rich Ass

3 years ago

ShemaleZ

amateur, teen (18+), first time
08:14 64%

Dad lecturer brings a naughty twist to the conference with a cougar and first-time antics

1 year ago

XXXVogue

handjob, amateur, shemale, cougar, heels, first time
30:27 86%

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

1 year ago

VideoSection

anal, asian, 18, ass, skinny, first time, missionary
04:54 66%

First time this cute babe allows her lesbian mature aunt to lick her pussy

2 years ago

HellPorno

mature, cute, lesbian, hairy, ass licking, babe, aunt
10:57

Are you excited about your first time with a tranny

11 years ago

xHamster

first time
12:40 43%

First Time Using Our Sex Swing! Tgirl On Girl Lesbian Couple

5 years ago

ShemaleZ

BDSM, first time, couple, amateur, shemale and girl
08:46 60%

Cute Tgirls Enjoy Anal Sex with each other

7 years ago

TrannyGem

cute, natural, college, first time, FTM
05:55 57%

Hardcore granny sex and blonde shemale fucks female first time Slutty

10 years ago

TXXX

granny, shaving, first time
15:54

SOMEONES SPUNKING

4 years ago

TrannyGem

strip, goth, first time
06:04

This is how I keep my caboose after penetrating stiff with my stepdad

1 year ago

ShemaleMovie

homemade, teen (18+), creampie, first time, bareback, teen anal (18+)
01:10

Very First time trans doll TheJuicyJosi bjed a trunk (blow) and get humped before web cam

2 years ago

KeekAss

first time
16:51 71%

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

1 year ago

HClips

shemale fucks guy, asian, amateur, first time, ladyboy
09:43

Tattooed Couples First Time With Trans Atm & Facial - Dark Leaves And Lily Lu

10 months ago

HClips

threesome, couple, facial, blonde, small tits, first time
06:07

First time guest anally fucked in the house

5 years ago

AShemaleTube

first time
15:37

Nervous First Time For This Trans With Hot Woman

2 months ago

AShemaleTube

masturbation, blowjob, first time, shemale
15:15 77%

VERY FIRST TIME TRANSGENDER PLOWED IN BOOTY AND CREAMPIED

3 years ago

KeekAss

amateur, stockings, creampie, bareback, first time, webcam
15:00

DARKHAIRED BABE SHEMALE POUND LITTLE YOUNG BABE HOLE

2 years ago

XoZilla

first time
06:09 50%

Trap first-timer wanks her massive man sausage

1 year ago

ShemaleMovie

femboy, small cock, solo, jerking, first time
07:08

Cowboy dad plows a TRANS for the very first TIME EVER

5 months ago

ShemaleMovie

anal, big cock, first time
11:43

I want your first time with a tranny to be amazing

9 years ago

xHamster

first time
08:12

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

1 year ago

xHamster

shemale, first time
08:10

Teenage ladyboy nurses and strong shaking climax first time Sucking

5 years ago

ShemaleTaxi

taxi, first time, college
05:08

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

3 months ago

ShemaleTaxi

beauty, blowjob, threesome, BBC, first time
18:18

Nymphomaniac Ugly Mature tricked to Lesbian Strap-On screw by Stranger big Boobs blondie MILF

2 weeks ago

VideoSection

mature, strapon, lesbian, MILF, orgasm, ugly, 18
05:06

Naked Nicolly Nogueira first time ass fucked

7 years ago

DrTuber

big ass, ass, first time
23:46

Guys first Time with Tgirl

6 years ago

BeMyHole

kissing, nipples, 69, panties, jeans, first time
14:20

My Very First Time With A sheboy Was Awesome

6 years ago

TrannyGem

first time
05:01 72%

[Trans] My First Time Venus Lux

4 years ago

TrannyOne

feet, heels, first time
18:38 82%

Melissa Masters - Your Very First Time Trans Femdom GFE

9 months ago

DrTuber

femdom, solo, cumshot, big cock, ass, first time
33:58 88%

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

8 months ago

KeekAss

handjob, shemale, first time
15:46 76%

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

1 year ago

ShemaleMovie

shemale, strapon, train, BDSM, crossdresser, husband, ass
03:06 72%

Grooby Girls featuring angels pink asshole dirt

8 months ago

PornHat

feet, cute, teen (18+), solo, 18, nipples, glasses
16:34

First time

7 years ago

ShemaleZ

first time
07:31 67%

Transgender mom, young petite, sissy feminization

5 months ago

XXXVogue

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12:25

MonikaMonika First time anal cd

3 years ago

xHamster

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07:07

Redhead shemale fucks her dates ass for the first time

2 years ago

TrannyGem

first time
06:20 85%

Tgirl Emma Roses first time with a woman

2 years ago

KeekAss

first time, shemale and girl, lingerie, big tits
07:03 60%

Getting dominated and fellating hard-on for the very first time like a little slut with facial

3 months ago

ShemaleTaxi

amateur, feet, BDSM, facial, spanking, blonde, deepthroat
12:47 93%

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

2 months ago

ShemaleTaxi

cumshot, ladyboy, amateur, first time, missionary, POV
11:30

First Time With A Ts Goddess

10 months ago

ShemaleZ

shemale, cumshot, first time
08:00 43%

Tight russian teen massage and rough first time Lilly is a s

8 years ago

IcePorn

teen (18+), massage, russian, first time, tight
12:01

TRANSFIXED - CIS And Trans Mermaids Explore New Bodies In First Time Fuck! Jewelz Blu And Kasei Kei

3 years ago

TXXX

first time
06:16

TGirl Sarah first time banging some dude

7 years ago

TrannyOne

first time
22:53

Young dude Fucks Blonde Latin Shemale Anal for the first Time

5 months ago

ShemaleMovie

shemale fucks guy, first time, 18
09:39 81%

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

4 months ago

HClips

amateur, small cock, shemale, POV, small tits, first time
08:14

Yaya (trans) - Having this raunchy hump for the first-ever time

1 year ago

ShemaleTaxi

first time, small cock
05:41

Tranny for first-ever Time Intercourse - Kimcock

7 years ago

TrannyGem

handjob, anal, ladyboy, ass, gape, first time
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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05:57

Slim blonde t-girl experiences big black cock for the first time in POV

8 months ago

XXXVogue

amateur, POV, shemale and girl, BBC, first time
06:01

Verified amateur rough anal first time Punish my nineteen year-old bum

4 years ago

TrannyOne

first time, amateur
06:13

Transsexual Fatty Blows Dick First Time

2 years ago

GetTranny

first time
16:43 83%

Feels Like The First Time . . .

4 years ago

TrannyOne

skinny, first time, anal
12:17

You will never leave behind your very first time with she-creature babe Mel

6 years ago

HDSex

first time
06:15

Jamie Kelly fucks for the first time with another trans woman

3 years ago

XXXDan

threesome, first time

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