SHEMALE • FIRST TIME 3,965 videos

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04:30 82%

Topping a guy friend for the first time!!!

4 years ago

TrannyOne

first time
07:37 85%

Cutiepii33quinn Gets Her Cherry Arse Nailed For Very First Time

2 months ago

PePorn

POV, amateur, first time
08:12 79%

My first time with a real shemale

1 year ago

XXXDan

brazil, orgasm, facial, first time
18:38 60%

Melissa Masters - Your Very First Time Trans Femdom GFE

1 week ago

DrTuber

femdom, solo, cumshot, ass, first time
03:06 77%

Transgender scene with sultry fiancée from Grooby Girls

2 months ago

PornHat

feet, solo, first time, nipples, glasses, jeans
23:44 61%

First-ever time for my hubby plow with Ladyboy

2 years ago

ShemaleTaxi

handjob, bisexual, anal, orgasm, ladyboy, taxi, first time
10:12 88%

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

9 months ago

ShemaleZ

small cock, shemale, 18, first time, small tits
14:56 57%

Domme T: first-ever Time rope-On Virgin

1 year ago

ShemaleTaxi

shemale, first time, kissing
08:07 85%

I try my transsexual friends cock for the first time

1 year ago

PornDr

handjob, beauty, blowjob, german, wife, cumshot, masturbation
08:12

My first time with a tranny

2 years ago

xHamster

first time
08:00 57%

Christmas orgy first time Slumber Party

6 years ago

IcePorn

teen (18+), first time, party
12:07 58%

You will never forget your first time with shemale babe Mel

9 years ago

xHamster

blowjob, babe, erotic, first time
11:52 43%

Your first time with a tranny will be amazing

10 years ago

xHamster

blowjob, erotic, first time, amateur
05:08 88%

Dude for the first time gets shemales male stick

6 years ago

Analdin

swinger, party, fetish, first time, hardcore, ladyboy
10:36 72%

My First Time With My New Ejaculating Fantasy Dildo

2 years ago

BeMyHole

dildo, redhead, solo, toys, first time, shemale
14:35 52%

Very first time unexperienced crossdresser gets jizz al over by sugar daddy

2 years ago

ShemaleMovie

orgasm, crossdresser, first time
08:09 78%

My very first time

4 years ago

TrannyOne

first time
25:12 65%

Cool tranny and lovely tutor Real guy first-ever time (นางใน)

4 years ago

TrannyGem

blowjob, redhead, first time, shemale fucks guy
10:28 73%

Boy very first time with trans

5 years ago

HDSex

first time, amateur
08:14

My first-ever time with a ladyboy

2 months ago

ShemaleMovie

ladyboy, first time
32:17 82%

Helena Price - First Time With A Ladyboy Hd

4 years ago

ShemaleZ

big tits, ladyboy, tattoo, crossdresser, ass licking, first time
51:27 68%

Little ones first time - all 3 angles

5 years ago

TXXX

asian, bareback, first time, amateur
05:14 76%

Trans has her first time with her step cousin

2 years ago

ShemaleTaxi

amateur, homemade, anal, cousin, first time, shemale
01:28 78%

Casting Guy First Time - Itzelxxx

2 years ago

TXXX

casting, first time
16:30 64%

Teen shemale LOVES first time with boyfriend

10 years ago

TXXX

blowjob, first time, boyfriend
20:33 90%

My first time getting dominated by a hot blonde trans babe

1 week ago

XXXVogue

shemale, blowjob, anal, big tits, BDSM, blonde, babe
15:51

Vol #8: boinked For The first Time on Femout

1 month ago

ShemaleTaxi

kissing, small cock, big tits, big cock, deepthroat, bareback, small tits
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
10:12

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

1 month ago

ShemaleZ

cum in mouth, first time, big ass, cum in ass
12:29 81%

Shy Latino First Time With A Shemale

6 years ago

TXXX

shy, first time
11:30

First Time With A Ts Goddess

3 weeks ago

ShemaleZ

shemale, cumshot, first time
05:17 55%

Cd and Str8 First time

6 years ago

TXXX

first time
12:08 83%

My First Time With A Trans

2 years ago

BeMyHole

amateur, big tits, ass licking, first time, hardcore
15:57

The first time

2 years ago

AShemaleTube

amateur, POV, first time
06:15 80%

Straight guys first time to fuck tranny

2 years ago

TrannyOne

first time
21:17 86%

I went to pulverize a trans with a good-sized jizz-shotgun and finished up being violated into by her in the end.

6 months ago

TrannyGem

creampie, muscle, big tits, blonde, big cock, ass, futanari
15:53 88%

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

1 month ago

ShemaleTaxi

big cock, shemale fucks guy, small cock, kissing, first time
03:25 44%

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
13:25

His very first time with a ladyboy

7 years ago

HDSex

asian, nylon, first time
23:22 79%

Fucked for the First Time

5 years ago

BeMyHole

femdom, latex, anal, dogging, panties, first time, shemale fucks guy
10:36 86%

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

1 year ago

KeekAss

amateur, anal, solo, cumshot, masturbation, first time
14:40

Now is your first time: Blowjob, Amateur Babe Porn

2 months ago

XXXDan

first time, asian, cumshot, missionary
03:34

Melissa Masters In Your Very First Time - Trans Femdom Gfe

1 month ago

Fuxxx

amateur, solo, asian, first time, femdom
07:30

The First Time This Man Has Sex With A Trans

1 month ago

ShemaleZ

first time
16:00 88%

Femdom Ts Initiation: First Time Fuckers

5 years ago

ShemaleZ

femdom, threesome, first time, fetish
04:31 82%

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

1 week ago

TrannyGem

amateur, cute, shemale, creampie, anal, fetish, dogging
30:15

Femout XXX: Nurse Kays First Time on Film

2 days ago

$$ FapHouse

shemale, anal, couple
06:25 75%

Ladyboy Amy Fucks Guys Ass For The First Time

3 years ago

DrTuber

blowjob, POV, asian, first time, shemale fucks guy
17:07 66%

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

1 year ago

TrannyGem

mom, fat, instruction, facesitting, shemale and girl, stepmom, domination
14:00

My First Time With A Trans Was Incredible

1 week ago

BeMyHole

shemale, first time
15:03 73%

First time sucking dick? And swallowing my hottest patrons

2 months ago

IcePorn

handjob, shemale, blowjob, POV, swallow, first time
12:42

The nylon fetish pt2 Sissy guy first time penetrate ladyboy

4 months ago

ShemaleMovie

big ass, BDSM, shemale, nylon, 3D, first time
08:10

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

1 year ago

ShemaleTaxi

first time, solo, orgasm compilation, orgasm, compilation
09:37 74%

Coming Back From A Party, Lizzy Makes Me Very Naughty

10 months ago

BeMyHole

shemale, amateur, shemale and girl, party, first time, MILF
05:00 63%

Ts gets blowjob first time Sneaking Around With Daddys partner

4 years ago

TrannyOne

first time
08:14 80%

Trans Taking an anal chastity

6 months ago

ShemaleMovie

creampie, anal, BDSM, crossdresser, british, big cock, domination
07:39 69%

Trap Schoolgirl Anal For The First Time

6 years ago

TrannyOne

first time
07:43

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

1 month ago

XXXVogue

teen anal (18+), femboy, teen (18+), first time, shemale
05:32 40%

I came for the very first time

1 month ago

TrannyGem

teen (18+), fetish, japanese, 18, anime, dress, thong
14:58 83%

My first time with a trans girl !!

1 year ago

xHamster

amateur, homemade, teen (18+), shemale, lingerie, shemale and girl, big cock
02:25 50%

I was confused the first time I saw this.

10 years ago

xHamster

18, first time
21:45

Guy first time with blonde Tgirl

15 years ago

AShemaleTube

first time, shemale fucks guy
02:51 69%

FIRST TIME real dick ANAL fuck - TATTOO couple vs shy girl - ATM female orgasm, anal GAPE (goth, punk, alt porn)ZF046

7 months ago

Sexu

lesbian, bisexual, couple, orgasm, tattoo, shy, goth
25:29

Ladyboy Fucks New Boyfriend Outdoors for the First Time Anal

Yesterday

AShemaleTube

cumshot, shemale fucks guy, outdoor, ladyboy
15:21 78%

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

7 months ago

SomePorn

blowjob, anal, dogging, ass licking, cumshot, ass, deepthroat
06:10 69%

Dudes very first Time With A t-girl

5 years ago

HDSex

prostitute, first time
10:21

My Teen Stepsister Wants To Try A Cock For The First Time

Today

BeMyHole

domination, shemale, small cock, anal, first time
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
06:34

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

1 year ago

BeMyHole

feet, bondage, BDSM, big cock, first time, shemale fucks guy
07:37 83%

First time in the Ass iwant a doggy style!

1 year ago

AShemaleTube

cumshot, amateur, first time
28:18 83%

Amazing Roxxie Moth Gets Anal Bareback First Time

4 years ago

BeMyHole

cute, stockings, blowjob, first time, hardcore, bareback
18:24 81%

The very first time

2 years ago

AShemaleTube

mature, stockings, shemale, lingerie, crossdresser, sissy, first time
15:30

Vol #2: boinked For The first Time on Femout

2 months ago

ShemaleTaxi

casting, small cock, anal, big cock, small tits, first time
06:20 60%

Teen guy sucking tranny cock first time

4 years ago

TrannyOne

teen (18+), first time
08:12

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

2 years ago

xHamster

amateur, cum in mouth, first time, cum in ass
04:38

Dudes first time anal sex with shemale

6 years ago

ShemaleZ

first time
06:32 88%

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

2 years ago

ShemaleTaxi

femdom, asian, filipina, domination, first time
08:08 60%

My very first time

7 years ago

xHamster

anal, first time, shemale fucks guy
32:59 50%

Helena Price 1st Time Transgender dame

2 years ago

ShemaleTaxi

shemale, first time
07:18 79%

TGirl fucks Step sister booty For The First Time

8 months ago

VideoSection

tattoo, blonde, shemale, first time
06:13

Transsexual Fatty Blows Dick First Time

1 year ago

GetTranny

first time
07:37

Cutiepii33quinn gets her cherry arse nailed for very first time

4 years ago

TrannyGem

first time
08:07 67%

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

9 months ago

TrannyGem

cumshot, first time, creampie, old man, german, old and young (18+)
05:15

Shemales donk acquires poked stiff

4 months ago

ShemaleMovie

big cock, first time
02:18

First-Ever Time Rapper Porks Transgender in V-Card

2 weeks ago

TrannyGem

chastity, hardcore, crossdresser, shemale, sissy, 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

2 years ago

ShemaleTaxi

asian, BDSM, ladyboy, big cock, deepthroat, filipina, domination
1:58:01 60%

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

8 months ago

ShemaleZ

lingerie, shemale, asian, first time
07:49

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

1 year ago

BeMyHole

first time, 18, asian, uniform
01:21 68%

Arab Femboy First Time Anal

4 years ago

AShemaleTube

homemade, arab, first time, femboy, domination
05:53

Im A Bit Nervous To Fuck My First Tgirl

2 days ago

BeMyHole

big cock, lingerie, blowjob, first time, ass licking
03:12 80%

Crossdresser Fucks Uncle for First Time

7 years ago

ShemaleZ

uncle, first time, crossdresser
06:50

Beautiful Local Girl Hardcore sex with Bf for the First time

8 years ago

AShemaleTube

first time
02:25

Twenty one yo Finnish trans dolls first-ever time getting poked on camera

9 months ago

TrannyGem

teen (18+), amateur, first time, POV, teen anal (18+), finnish
05:32 57%

First time

6 years ago

xHamster

mature, amateur, mature anal, first time
02:28

First Time CD ecperience

5 years ago

xHamster

first time
09:56 60%

Boy first time with tranny

6 years ago

ShemaleZ

first time
08:00

Anastasia Penny Made His First Time Memorable

1 year ago

GetTranny

cumshot, first time
08:00 59%

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
15:34 83%

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

10 months ago

xHamster

compilation, asian, solo, masturbation, first time, shemale
03:40

First Time Guest Anally Fucked In The House

3 months ago

xShemaleTube

first time
05:17

Dudes first time anal bang-out with she-male

3 years ago

ShemaleTaxi

taxi, first time
08:12 54%

Skinny teen femboy getting fucked first time

11 months ago

xHamster

amateur, german, anal, crossdresser, blonde, skinny, sissy
06:17

Transgender princess Thippy & Noi first time trio some

11 months ago

ShemaleMovie

shemale fucks guy, ladyboy, first time
04:00

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

9 years ago

TXXX

girlfriend, first time
16:19

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

4 years ago

TrannyGem

brazil, teen anal (18+), first time
06:20

Watch Busty Tgirl Her First Time Sex With Emma Rose

1 year ago

GetTranny

MILF, first time
01:10

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

2 years ago

KeekAss

first time
24:45

Ts Ingrid Doll Pegs Her Submissive For The First Time

Yesterday

HClips

shemale, big cock, amateur, pegging, POV, first time
25:47

Outdoor Latina Tranny Fucks Guy for the First Time Anal in Tight Asshole

Yesterday

AShemaleTube

cumshot, vintage, tight, shemale fucks guy, anal, big cock, latina
2:40:58 60%

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

8 months ago

ShemaleZ

big cock, shemale, asian, shemale and girl, first time
09:46 93%

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

2 years ago

TrannyGem

dildo, babe, college, toys, sissy, first time, femboy
16:51 72%

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

6 months ago

HClips

shemale fucks guy, asian, amateur, first time, ladyboy
07:52

Pierce Pariss Made Desire in First Bliss

1 week ago

XoZilla

missionary, heels, shemale, first time
11:34 79%

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

2 years ago

AnySex

handjob, shemale, blowjob, sissy, first time, small tits
09:28

Teen Thug first time with Tranny

6 years ago

ShemaleZ

first time
14:39 84%

Ride With A Beautiful & Wonderful Tranny Isabella Salvatore

5 months ago

BeMyHole

beauty, public, big tits, car, 18, jerking, riding
08:12

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

11 months ago

xHamster

shemale, first time
04:00 67%

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

9 years ago

TXXX

russian, teacher, first time
04:00 57%

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

11 years ago

TXXX

russian, shemale and girl, teacher, first time
11:56 43%

First Time With TS

8 years ago

ShemaleZ

vintage, first time

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