SHEMALE • FIRST TIME 3,185 videos

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03:56

First time exhibition masturbation in public nature trail

6 days ago

AShemaleTube

public, crossdresser, shemale, first time
05:01 58%

Old man eats teen ass first time Frannkie's a fast learner!

2 years ago

TrannyOne

teen (18+), old man, first time
06:50

Beautiful Local Girl Hardcore sex with Bf for the First time

6 years ago

AShemaleTube

first time
15:28

Brunette gets Pegged by Wife for the first Time

3 years ago

TrannyGem

wife, clit, big clit, erotic, pegging, first time, sensual
02:55

The first time I take a dick in my ass

4 years ago

xHamster

couple, first time
08:10

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3 years ago

ShemaleTaxi

taxi, first time
08:10

Rough tranny first-ever time mind-blowing y., Alexa Nova and Kendall

3 years ago

ShemaleTaxi

bondage, first time
44:40 61%

Indian Taina - My First Time With An Indian

1 year ago

ShemaleZ

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06:15

Heterosexual boy have joy boning transexual for the first-ever time (Crystal Thayer, Large Titties, Yam-Sized Orbs)

1 year ago

KeekAss

tattoo, first time
06:01

Horny big cock tranny fuck for the first time

2 years ago

TrannyOne

first time
05:07

Extraordinary latina transsexual first time bum fucked

4 years ago

DrTuber

blowjob, latina, first time
14:14

Teen Crossdresser first time anal

4 years ago

ShemaleZ

amateur, anal, crossdresser, ass, cum in mouth, first time, cum in ass
08:08 58%

My very first time

5 years ago

xHamster

anal, first time, shemale fucks guy
10:46

Transexual Brandy Alexander gets fucked and facialized for the first time

5 years ago

ShemaleZ

facial, first time
12:23 85%

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

3 years ago

KeekAss

doll, instruction, JOI, first time
26:23

Tranny fucks a little trans for the first time on the New Year

1 month ago

JizzBunker

small cock, tattoo, shemale, first time
1:06:07

Small tits latin gf Valentina anal fucked for the first time

4 years ago

VipTube

first time
06:14

GENDER X Fucking my tranny friend for the first time! - Dante Colle, Ariel Demure

2 years ago

TrannyOne

first time
03:06

Joeystransfeetgirls - Kalli Grace First Time Footjob

1 week ago

AShemaleTube

shemale, footjob, interracial, first time, domination
05:49

Satisfying nosey - his very first time with a trans

2 years ago

KeekAss

first time
15:00

Asian Tranny First-Time Fantasy part 1 - Sharnell Dupree

9 months ago

xHand

gagging, pool, short hair, spanking, natural, first time, missionary
05:07

Dude for the fist time has tranny up his rear

5 years ago

XoZilla

swinger, party, fisting, first time
16:43

Feels Like The First Time

2 years ago

ShemaleZ

first time
05:09

Dude had first time anal with shemale

2 years ago

TrannyOne

first time
10:10

Stepbro Analed Ts Stepsis For First Time

1 year ago

ShemaleZ

anal, first time
10:38

A Ginger Steals Vixens Virginity !!! (FULL) !!!

1 year ago

PornHub

glasses, slut, sissy, first time
03:11

Guy Feminized And Fucked For First Time

4 months ago

ShemaleZ

BDSM, first time
08:39

First time he suck a cock

6 months ago

AShemaleTube

first time
39:29

Sharnell Dupree - First-time Fantasy

3 years ago

TXXX

first time
05:21

Amateur Ladyboy Fucked In A Hotel Room

4 months ago

BeMyHole

POV, hotel, first time
01:21

Mirans First Time

6 months ago

TXXX

first time
13:00

Nur mit Gummi in den Arsch bitte

2 years ago

xHamster

german, mature anal, teen anal (18+), MILF, swallow, first time, saggy tits
04:17

Last night I pummeled him over and over until he moneyless

5 months ago

TrannyGem

creampie, first time, femboy
05:55

Timid French sissy first time to fellate

2 years ago

HDSex

french, crossdresser, first time
10:06

Trans babe Daisy meets Dante Colle for the first time and fucks him

3 years ago

AShemaleTube

first time
05:09

Tight Ass Tgirl Gets Fucked For The First Time

4 years ago

ShemaleZ

tight, first time
06:27

My first time with a black tgirl

2 years ago

TrannyOne

first time
04:38

Dude for the first time gets shemales dick

4 years ago

TXXX

first time
22:46 55%

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

2 years ago

TrannyOne

feet, ass to mouth, cum in mouth, sissy, first time, cum in ass
06:15

Spencer Bradley first time to suck a tranny cock

2 years ago

AShemaleTube

first time
09:03

Getting pegged for the very first time part 1

1 year ago

ShemaleTaxi

strapon, pegging, first time
05:06

Naked Nicolly Nogueira first time ass fucked

4 years ago

DrTuber

big ass, ass, first time
18:53

Made His First Time Memorable - Anastasia Penny

3 months ago

ShemaleZ

cumshot, big cock, first time
03:53

Bot Having Sex For The First Time With Tranny

11 months ago

GetTranny

first time
19:58 65%

MY FIRST TIME FUCK BEAUTIFUL SHEMALE ON UPSTAIRS

1 year ago

xHamster

beauty, small cock, creampie, anal, interracial, bareback, small tits
38:29

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.

7 months ago

BeMyHole

stockings, big tits, blonde, first time, hardcore
05:55

Shemale Creampies Guy for the first Time

4 years ago

ShemaleZ

first time
12:40

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

2 years ago

ShemaleZ

BDSM, first time
18:47

BrFat guy gets his thick ass toyed and stretched by the horny TS babe

3 years ago

BeMyHole

dogging, mask, dress, first time
08:00

M584g02 Son Who Has Returned For The First Time In A Few Years Is A Transcendental Transsexual

7 months ago

GetTranny

japanese, cum in mouth, first time
09:15

Young german amateur transexual teen shemale fucks first time anal with huge cock

1 year ago

TrannyOne

german, teen anal (18+), bareback, first time
06:01

Transgender with fat Cock Fucks hetero man

1 year ago

ShemaleTaxi

fat, deepthroat, first time
23:19

First Time For My Husband Fuck With Ladyboy

1 year ago

Upornia

amateur, teen (18+), asian, husband, first time
08:00

Latino daddy bear first time Sneaky Father Problems

2 months ago

IcePorn

teen (18+), POV, first time
05:56

Amateur Tgirl First Time On Cam

5 years ago

ShemaleZ

first time
08:00

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

6 years ago

IcePorn

teen (18+), massage, russian, first time
08:45

Jaw-Dropping T-Model Ingrid Moreira smashes rigid dude for his very first time! Facial Cumshot!

2 years ago

TrannyGem

facial, first time
05:13 85%

She fellates a thick FUTA salami for the very first time

6 months ago

TrannyGem

cartoon, cum in mouth, futanari, first time
05:01

[Trans] My First Time Venus Lux

2 years ago

TrannyOne

feet, heels, first time
04:39

My first-ever time with a nubile she-creature

4 years ago

KeekAss

skinny, first time
28:31

Roxxie Cracking In A First-Ever Timer

3 years ago

TrannyGem

first time
05:58

Blonde shemale cums on herself first time She has always wondered what it

2 years ago

TrannyOne

lesbian, outdoor, first time
10:36

My first threesome!!!

3 months ago

XXXDan

amateur, beauty, german, threesome, double anal, blonde, first time
10:39

A Ginger Steals Vixens V-Card !!! (TOTAL) !!!

1 year ago

TrannyGem

glasses, slut, first time
15:57

Yvanas First Time On Porn - Alexandra Bxl

1 year ago

ShemaleZ

stockings, lingerie, first time
10:16

My First Time With A Trans

2 years ago

ShemaleZ

outdoor, ass licking, first time
10:38

The First Time You Never Forget

3 years ago

Upornia

teen (18+), first time
29:07

Teaching str8 young boy first time ladyboy experience

6 years ago

ShemaleZ

ladyboy, first time
05:45

My First Time with a Transsexual

6 years ago

ShemaleZ

first time
04:37

Very Cute Couple First Time Anal

4 years ago

xHamster

small tits, first time
08:42

Redhead ladyboy Lily Demure crazy sex movie

5 months ago

XoZilla

facial, cum in mouth, first time, cum in ass
06:02 70%

Filipino Femboy Has First Time Bareback Anal Sex On Camera

3 years ago

ShemaleZ

filipina, first time, femboy
13:25

First-Ever Time Tutor of Magic and Alice Blitz ( part 1 )

2 years ago

TrannyGem

teacher, first time
06:26

Trans Lesbians first-ever Time Together

1 year ago

ShemaleTaxi

shemale, lesbian, taxi, first time
08:00

Teen tranny hd first time Itsy Bitsy HotSpot

6 years ago

VipTube

first time
03:50

Tattooed Guy Enjoys His Very First Time Of Trans Transaction

1 year ago

GetTranny

first time
10:57

MY FIRST TIME

10 years ago

AShemaleTube

first time
17:19

Strikingly Stunning T-Girl is Providing me a Flawless Oral Pleasure

3 years ago

TrannyGem

facial, natural, first time
10:25

The Pool Guy Rims Some Tranny Ass for the First Time

3 months ago

AShemaleTube

first time
06:13

First time with a shemale hooker

4 years ago

AShemaleTube

hooker, big tits, first time
37:57

Sexy traps first Video

2 years ago

XXXDan

blonde, skinny, small tits, first time
13:47

Newbaby s almost first time

4 years ago

AShemaleTube

first time
08:11

His first time sex with a Tgirl is perfect!

10 years ago

AShemaleTube

first time
06:15 75%

Marilyn Johnson first time to blow shemale meaty cock

2 years ago

AShemaleTube

first time
06:09

Casting Amateur Tgirl Deepthroating Dick

5 years ago

TrannyGem

casting, POV, audition, first time
03:10

BOBSTGIRLS: Boom Boom - New Girl Lola Bloom

1 year ago

xHamster

cute, first time
04:08

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

5 years ago

ShemaleZ

fetish, first time
11:08

THE VERY FIRST TIME you not ever LEAVE BEHIND

3 years ago

TrannyGem

ass to mouth, first time
05:42

First-ever time

4 years ago

HDSex

first time
13:51

Ts Was Fucked By Xxl Cock For The First Time 14 Min - Inked Girl

1 year ago

ShemaleZ

first time
14:08

Man gets pulverized by transgender princess for the very first time

2 years ago

TrannyOne

first time
06:12

Filipino femboy has first time bareback ass-fuck romp on camera

4 years ago

ShemaleMovie

small cock, filipina, first time, femboy
05:57

My first time with a black tgirl

5 years ago

ShemaleZ

first time
11:35

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

3 years ago

TrannyGem

vibrator, first time
1:40:20

My First Time With A Tranny (Full Hd Version – Director’s Cut)

1 year ago

TrannyOne

first time
07:16

First-ever time with a she-creature, I called Renata Fontes to give and fellate very hard

3 years ago

ShemaleTaxi

taxi, first time
53:12 84%

First time anal couple sex blonde tgirl

5 years ago

AShemaleTube

homemade, shemale, anal, couple, ass to mouth, webcam, first time
07:37

My Stepsister Wanted To Try A Good Cock For The First Time 8 Min - Dante Colle

2 months ago

TXXX

first time
08:00

Agatha Lira - My First Time With A Trans And The First

10 months ago

GetTranny

first time
11:35 75%

First time Vibrator Cum for t-girl Moxxi Mewws

2 years ago

PornHub

small cock, redhead, piercing, goth, vibrator, first time
14:15

You will never forget your first time with t-girl Mel

3 years ago

ShemaleMovie

first time
03:11

TGIRLBBW: DEBUT OF SUMMER FLOW!

2 months ago

JizzBunker

feet, BBW, first time
26:35 60%

Sissy very first Time Dressing Up For dad

11 months ago

ShemaleMovie

amateur, crossdresser, dress, sissy, first time
06:40

Tgirls first-ever time with a Bio lady

4 years ago

VideoSection

first time
07:45

18 year old German amateur tranny next door makes homemade anal porn

3 months ago

JizzBunker

amateur, homemade, german, student, 18, caught, college
11:36

Crossdresser CD Blows Straight Boy first Time Candicane

1 year ago

TrannyOne

first time
03:02

This is Allicia Nogueiras first time on our site and we

9 years ago

DrTuber

first time
21:03 50%

T Gurl Cums in her dress

3 years ago

xHamster

public, outdoor, compilation, dress, cumshot compilation, first time
05:27

My First Time Trying ass fucking with a (HUGE) fuck stick (Trans teen, Big Cock, Sukai)

3 years ago

ShemaleTaxi

huge dildo, teen anal (18+), first time
05:55

Hardcore granny sex and blonde shemale fucks female first time Slutty

7 years ago

TXXX

granny, shaving, first time
10:28

Whorish femboy crossdressing for the first time finds 2 boys to tagteam her backside and film it

5 months ago

ShemaleTaxi

first time, femboy
05:05

Oral And Hardcore Sex Fucked For The Very First Time

2 years ago

BeMyHole

first time
05:38

Inked BOY DOES CASTING FOR THE FIRST TIME WITH A TRANSGENDER GIA ITZEL

8 months ago

BeMyHole

casting, first time
05:52

First time

4 years ago

ShemaleZ

first time
18:28

Its time you tasted your first shemale cock

4 years ago

xHamster

first time
12:58

Mistress pegs sissy for the first-ever time

1 year ago

ShemaleTaxi

femdom, strapon, pegging, taxi, sissy, first time
08:00

Life of the party first time Deep Throat Challenge

4 years ago

IcePorn

party, group, first time
05:58

Shemale first time sex with a guy

3 years ago

BeMyHole

short hair, first time
05:45

Kasey Kei And Jesse Pony In Blonde First Time Having Sex With A Transgender

10 months ago

TXXX

first time
06:24

Blonde teen shemale gets fucked hard first time

2 years ago

TrannyOne

teen anal (18+), first time

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