SHEMALE • FIRST TIME 4,065 videos

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04:30 82%

Topping a guy friend for the first time!!!

4 years ago

TrannyOne

first time
07:37 84%

Cutiepii33quinn Gets Her Cherry Arse Nailed For Very First Time

4 months ago

PePorn

POV, amateur, first time
08:07 86%

I try my transsexual friends cock for the first time

1 year ago

PornDr

handjob, beauty, blowjob, german, wife, cumshot, masturbation
03:06 80%

Transgender scene with sultry fiancée from Grooby Girls

4 months ago

PornHat

feet, solo, first time, nipples, glasses, jeans
06:25 75%

Ladyboy Amy Fucks Guys Ass For The First Time

3 years ago

DrTuber

blowjob, POV, asian, first time, shemale fucks guy
08:12 81%

My first time with a real shemale

2 years ago

XXXDan

brazil, orgasm, facial, first time
23:44 62%

First-ever time for my hubby plow with Ladyboy

2 years ago

ShemaleTaxi

handjob, bisexual, anal, orgasm, ladyboy, taxi, first time
10:12 90%

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

11 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
14:34

Horny couples first time on the honeymoon: A Ts & a TS for your pleasure!

1 month ago

TrannyOne

shemale, first time
08:00 57%

Christmas orgy first time Slumber Party

7 years ago

IcePorn

teen (18+), first time, party
12:07 61%

You will never forget your first time with shemale babe Mel

9 years ago

xHamster

blowjob, babe, erotic, first time
05:08 87%

Dude for the first time gets shemales male stick

6 years ago

Analdin

swinger, party, fetish, first time, hardcore, ladyboy
11:52 46%

Your first time with a tranny will be amazing

10 years ago

xHamster

blowjob, erotic, first time, amateur
10:36 72%

My First Time With My New Ejaculating Fantasy Dildo

2 years ago

BeMyHole

dildo, redhead, solo, toys, first time, shemale
08:09 79%

My very first time

4 years ago

TrannyOne

first time
51:27 68%

Little ones first time - all 3 angles

5 years ago

TXXX

asian, bareback, first time, amateur
10:28 74%

Boy very first time with trans

5 years ago

HDSex

first time, amateur
01:28 73%

Casting Guy First Time - Itzelxxx

2 years ago

TXXX

casting, first time
16:30 67%

Teen shemale LOVES first time with boyfriend

10 years ago

TXXX

blowjob, first time, boyfriend
14:35 52%

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

2 years ago

ShemaleMovie

orgasm, crossdresser, 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
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
11:34 80%

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

2 years ago

AnySex

handjob, shemale, blowjob, sissy, first time, small tits
10:08

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

4 days ago

$$ FapHouse

toys, beauty, first time, pantyhose, solo, asian, korean
08:12 67%

My first time with a tranny

2 years ago

xHamster

first time
05:14 77%

Trans has her first time with her step cousin

2 years ago

ShemaleTaxi

amateur, homemade, anal, cousin, first time, shemale
15:51

Vol #8: boinked For The first Time on Femout

3 months ago

ShemaleTaxi

kissing, small cock, deepthroat, bareback, small tits, taxi, first time
09:30 76%

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
12:08 83%

My First Time With A Trans

2 years ago

BeMyHole

amateur, big tits, ass licking, first time, hardcore
05:19

Sunshyne Monroes exciting first time in domination

1 week ago

XXXVogue

big cock, shemale fucks guy, first time, blowjob
05:17 55%

Cd and Str8 First time

6 years ago

TXXX

first time
20:33 93%

My first time getting dominated by a hot blonde trans babe

2 months ago

XXXVogue

shemale, blowjob, anal, big tits, BDSM, blonde, babe
12:29 78%

Shy Latino First Time With A Shemale

6 years ago

TXXX

shy, first time
06:15 80%

Straight guys first time to fuck tranny

2 years ago

TrannyOne

first time
16:08

Guy enjoys first time with busty shemale

1 month ago

XXXVogue

amateur, cumshot, big cock, ass, first time, shemale fucks guy
23:22 79%

Fucked for the First Time

5 years ago

BeMyHole

femdom, latex, anal, dogging, panties, first time, shemale fucks guy
15:53 84%

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

3 months ago

ShemaleTaxi

big cock, shemale fucks guy, small cock, kissing, first time, deepthroat
15:57

The first time

2 years ago

AShemaleTube

amateur, POV, first time
10:36 86%

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

2 years ago

KeekAss

amateur, anal, solo, cumshot, masturbation, first time
29:59 87%

Sinn Sage And Erica Cherry - Astonishing Sex Scene Shemale Milf Exotic Just For You

3 years ago

Upornia

shemale, MILF, shemale and girl, cumshot, toys, first time
16:00 89%

Femdom Ts Initiation: First Time Fuckers

5 years ago

ShemaleZ

femdom, threesome, first time, fetish
21:41

MY HOMIE WOOED ME TO ATTEMPT A BIG BLACK COCK FOR THE VERY FIRST TIME - ALEJANDRA PALACIOS

4 days ago

KeekAss

shemale, black, BBC, hardcore, first time
13:25

His very first time with a ladyboy

7 years ago

HDSex

asian, nylon, first time
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.

8 months ago

TrannyGem

creampie, muscle, big tits, blonde, big cock, ass, futanari
14:15 80%

Beautiful shemale pounds the guys ass bareback for the first time

4 years ago

TrannyOne

first time
08:42 44%

First time getting ass fucked

3 weeks ago

XXXVogue

handjob, blowjob, POV, lingerie, ladyboy, british, cum in mouth
07:39 69%

Trap Schoolgirl Anal For The First Time

6 years ago

TrannyOne

first time
14:39 86%

Ride With A Beautiful & Wonderful Tranny Isabella Salvatore

7 months ago

BeMyHole

beauty, public, big tits, car, 18, jerking, riding
17:07 63%

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
07:43

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

3 months ago

XXXVogue

teen anal (18+), femboy, teen (18+), first time, shemale
10:38 78%

My first-ever ever 3some!!!

6 months ago

ShemaleMovie

amateur, beauty, shemale, double anal, blonde, big cock, babe
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
14:58 83%

My first time with a trans girl !!

1 year ago

xHamster

amateur, homemade, teen (18+), shemale, bisexual, lingerie, shemale and girl
06:15

Avery Lust can have her sexual needs satisfied

Yesterday

TrannyGem

first time
05:00 63%

Ts gets blowjob first time Sneaking Around With Daddys partner

4 years ago

TrannyOne

first time
15:03 74%

First time sucking dick? And swallowing my hottest patrons

4 months ago

IcePorn

handjob, shemale, blowjob, POV, swallow, first time
44:27

Ultra-kinky college girl anal invasion fuck-a-thon

Yesterday

ShemaleTaxi

college, shemale and girl, anal, shemale fucks guy, shemale, massage, sissy
10:12

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

3 months ago

ShemaleZ

cum in mouth, first time, big ass, cum in ass
07:37 83%

First time in the Ass iwant a doggy style!

1 year ago

AShemaleTube

cumshot, amateur, first time
04:38

Dudes first time anal sex with shemale

6 years ago

ShemaleZ

first time
18:38 50%

Melissa Masters - Your Very First Time Trans Femdom GFE

2 months ago

DrTuber

femdom, solo, cumshot, ass, first time, big ass
07:19 56%

Tranny and queer gang porno view first time Restrained Benjamin is in

5 years ago

ShemaleTaxi

taxi, first time
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 67%

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

9 months ago

Sexu

lesbian, bisexual, couple, orgasm, tattoo, shy, goth
08:00 63%

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
08:14 79%

Trans Taking an anal chastity

8 months ago

ShemaleMovie

anal, BDSM, crossdresser, british, big cock, bareback, sissy
02:57 79%

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
03:12 80%

Crossdresser Fucks Uncle for First Time

7 years ago

ShemaleZ

uncle, first time, crossdresser
18:24 84%

The very first time

2 years ago

AShemaleTube

mature, homemade, stockings, shemale, lingerie, crossdresser, sissy
08:08 60%

My very first time

7 years ago

xHamster

anal, first time, shemale fucks guy
08:01

The soiree is starting there will be raunchy hump tonight

3 days ago

VideoSection

first time, shemale fucks guy, femboy
06:20 60%

Teen guy sucking tranny cock first time

4 years ago

TrannyOne

teen (18+), first time
04:00

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

9 years ago

TXXX

girlfriend, 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
10:15 61%

Beautiful 18 yr elderly trans girl fucking for the first time with her new hook-up toy

1 year ago

ShemaleTaxi

amateur, homemade, 18, masturbation, skinny, first time
07:49

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

1 year ago

BeMyHole

first time, 18, asian, uniform
08:02

Intense toe-curling climax for first-time shemale Fatclitshit in the shower

Today

XXXVogue

bathroom
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
15:21 78%

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

9 months ago

SomePorn

blowjob, dogging, ass licking, cumshot, ass, deepthroat, reality
06:50

Beautiful Local Girl Hardcore sex with Bf for the First time

8 years ago

AShemaleTube

first time
06:34 50%

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

2 years ago

BeMyHole

feet, bondage, BDSM, big cock, first time, shemale fucks guy
06:32 86%

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, kissing
09:56 60%

Boy first time with tranny

6 years ago

ShemaleZ

first time
10:57

YOUNG BOY HAD HIS VERY FIRST TIME WITH A TRANS - LUANA PRADO

4 days ago

KeekAss

shemale, first time
01:21 70%

Arab Femboy First Time Anal

5 years ago

AShemaleTube

homemade, arab, first time, femboy, domination
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
06:24

Trans Khloe Kay slurps Aiden Ashley cooch first time

3 days ago

ShemaleMovie

first time
36:33

Carolina Biondi Trans Active Shooting For The First Time

1 year ago

ShemaleZ

first time, shemale, stockings, lingerie, tattoo
07:37

Cutiepii33quinn gets her cherry arse nailed for very first time

4 years ago

TrannyGem

first time
15:46 69%

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

1 year ago

ShemaleMovie

shemale, strapon, train, BDSM, crossdresser, husband, ass
03:25 47%

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
05:32 53%

First time

6 years ago

xHamster

mature, amateur, mature anal, first time
2:40:58 67%

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

10 months ago

ShemaleZ

big cock, shemale, asian, shemale and girl, first time
05:57

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

1 month ago

XXXVogue

amateur, POV, shemale and girl, BBC, first time
14:40

Now is your first time: Blowjob, Amateur Babe Porn

4 months ago

XXXDan

first time, asian, cumshot, missionary
06:15

Shemale first time sex with a guy

5 years ago

AShemaleTube

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
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
09:02 74%

J want you to take me like this!

3 months ago

ShemaleTaxi

amateur, shemale, french, lingerie, solo, taxi, first time
08:07 75%

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

11 months ago

TrannyGem

cumshot, first time, creampie, old man, german, old and young (18+)
08:12 53%

Skinny teen femboy getting fucked first time

1 year ago

xHamster

german, anal, crossdresser, blonde, skinny, sissy, 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
05:17

Dudes first time anal bang-out with she-male

3 years ago

ShemaleTaxi

taxi, first time
29:36

Teaching str8 young boy first time ladyboy experience

8 years ago

AShemaleTube

erotic, first time
10:26

Very first Time - Edible trans ladys backside fucked by a fake penis

1 month ago

KeekAss

first time, amateur, penis
06:09

Auditioning Tranny Tugging her Hard Cock

7 years ago

TrannyGem

casting, blowjob, POV, fetish, jerking, audition, ass
03:34

Melissa Masters In Your Very First Time - Trans Femdom Gfe

3 months ago

Fuxxx

amateur, solo, asian, first time, femdom
06:09 50%

Trap first-timer wanks her massive man sausage

8 months ago

ShemaleMovie

femboy, small cock, solo, jerking, first time
08:00

Anastasia Penny Made His First Time Memorable

2 years ago

GetTranny

cumshot, first time
11:11

First time stepbrother

1 year ago

ShemaleMovie

blowjob, femboy, homemade, seduced, first time
03:40

First Time Guest Anally Fucked In The House

5 months ago

xShemaleTube

first time
1:58:01 63%

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

11 months ago

ShemaleZ

lingerie, shemale, asian, first time, swallow
11:36

Crossdresser CD Blows Straight Boy first Time Candicane

2 years ago

TrannyOne

first time, crossdresser
05:15

Shemales donk acquires poked stiff

6 months ago

ShemaleMovie

big cock, first time
06:36

First time he's sucking a cock

2 days ago

AShemaleTube

crossdresser, mature, amateur
53:12 84%

First time anal couple sex blonde tgirl

7 years ago

AShemaleTube

homemade, anal, couple, ass to mouth, webcam, first time, frottage
11:35 67%

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

5 years ago

TrannyGem

vibrator, first time, dildo, cumshot
12:55

She made me jism twice! first time drilling Britney from Tantaly - Emily Adaire

6 months ago

ShemaleMovie

solo, big tits, first time, german, nylon, stockings

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