SHEMALE • FIRST TIME 3,210 videos

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29:36

Teaching str8 young boy first time ladyboy experience

6 years ago

AShemaleTube

erotic, first time
06:14 75%

First time with a Shemale Escort

5 years ago

AShemaleTube

mature, lingerie, first time, escort
06:01

First Time With Ts Hooker

5 years ago

ShemaleZ

hooker, vintage, domination, first time
05:57

Ebony and white nurses and shemale and mr 18 first time Horn

7 years ago

DrTuber

nurse, cuckold, 18, first time
12:01

MESMERIZED - Cis + Trans Mermaids Examine Fresh Figures In First-Ever Time Screw! With Jewelz Blu & Kasei Kei

1 year ago

KeekAss

lesbian, first time
08:00

Life of the party first time Deep Throat Challenge

4 years ago

IcePorn

party, group, first time
03:12

Crossdresser Fucks Uncle for First Time

5 years ago

ShemaleZ

uncle, first time
05:05

Oral And Hardcore Sex Fucked For The Very First Time

2 years ago

BeMyHole

first time
07:32

When I Lost My Virginity - Sex memories by Maya McAdamia

10 months ago

xHamster

first time
16:49

Her black transgirl fuck-stick is so meaty and rock hard

2 years ago

TrannyGem

JOI, first time
10:28

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

6 months ago

ShemaleTaxi

first time, femboy
05:58

Shemale first time sex with a guy

3 years ago

BeMyHole

short hair, first time
04:22

Alexa Cosmic transgender princess swimming in the river very first time in teal combi sundress

10 months ago

KeekAss

outdoor, crossdresser, first time
06:17

Ladyboy Jusmin First Time Anal

9 years ago

PornHub

anal, first time
05:55 50%

Lana violet pov blowjob and shemale pov blowjob first time B

7 years ago

IcePorn

old and young (18+), first time
03:56

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2 weeks ago

AShemaleTube

public, crossdresser, shemale, first time
39:15

Cute shemale girl gets anal fucked for the first time

1 year ago

xHamster

cute, first time
09:16

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

8 months ago

BeMyHole

teen anal (18+), latina, ass licking, first time
01:31

Nikk Montero first time in a lifetime drinking piss

1 year ago

xHamster

pissing, first time
06:07

First time guest anally fucked in the house

3 years ago

AShemaleTube

first time
06:12

His very first time with a trans - short

1 year ago

ShemaleMovie

crossdresser, first time
09:41

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

8 months ago

ShemaleZ

amateur, teen (18+), first time
10:20

Remigio Zampa starts a girl to anal intercourse!Roby Bianchi

4 years ago

xHamster

spanish, nipples, swallow, natural, vintage, seduced, puffy nipples
05:01

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2 years ago

TrannyOne

bus, first time
15:29

Its my first time letting a shemale rail my shaft

1 year ago

ShemaleTaxi

first time
05:48

First time with Shemale hooker

4 years ago

ShemaleZ

mature, hooker, first time
05:45

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

10 months ago

TXXX

first time
06:15

Jesse Pony first time having sex with a trans

11 months ago

UiPorn

first time
03:06

Joeystransfeetgirls - Kalli Grace First Time Footjob

2 weeks ago

AShemaleTube

shemale, footjob, interracial, first time, domination
16:08

His very first time with a trans, did he like it?

1 year ago

KeekAss

POV, anal, tattoo, first time
16:43

Feels Like The First Time . . .

2 years ago

TrannyOne

skinny, first time
17:26 82%

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

3 years ago

ShemaleZ

mature, first time, shemale fucks guy
14:15

You will never forget your first time with transgender princess Mel

4 years ago

ShemaleMovie

first time
11:08

MY VERY FIRST TIME WITH MASSIVE SHEMALE SPEAR

3 years ago

TrannyGem

thai, teen anal (18+), 18, first time
02:37

My first time sucking a cock

1 year ago

TrannyOne

first time
06:46

OH WoW..Tranny Fucks fine costa rican hoe for the first time

12 years ago

xHamster

first time
36:43

Very first time with my Hismith machine

2 years ago

ShemaleTaxi

orgasm, machine, sissy, first time
21:39 84%

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

3 years ago

TXXX

french, first time
32:02 77%

Smallish fuck-stick transgender princess first time porno

3 years ago

VideoSection

anal, ass, sissy, first time
10:15

Crossdresser First Time Sucks Cock Gets Fucked Facial Full Sissy

1 year ago

TXXX

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05:59

First time this shemale works such a big dick

3 years ago

HellPorno

69, first time
04:27

I Fucked By A First Time Crossdresser

2 years ago

TXXX

first time
06:34

My First Time in Tights: Embracing My Crossdressing Journey!

3 months ago

xHamster

first time
08:46

NextDoorStudios - Elliot Finns very first Time With Trans-fellow Luke Hudson

1 year ago

ShemaleTaxi

deepthroat, first time, missionary
45:20

His first time with a Shemale

4 years ago

xHamster

outdoor, first time
06:07

Stockinged trap sweetheart toys her taut caboose

3 years ago

ShemaleTaxi

close up, skinny, first time
07:00

Young girl big tits fucking old man first time Old clever ge

5 years ago

IcePorn

old man, old and young (18+), first time
06:07

Mature black tranny woman fuck young white boy first time

3 years ago

PornHub

handjob, black, old man, mature anal, hairy, old and young (18+), college
06:05

My very first time with a trans. Part 1 While my acquaintance rests

4 months ago

KeekAss

ladyboy, crossdresser, first time
06:16

Mujer trans y su novia hacen el amor desnudas (Modelo Alizze Luna)

1 year ago

TrannyGem

kissing, bisexual, double anal, first time, double penetration
06:03

Amateur tgirl jerking dick in first time solo

6 years ago

AShemaleTube

jerking, masturbation, first time
13:25

Crossdressing for the very first time was sexier than I imagined

2 years ago

ShemaleMovie

crossdresser, first time
05:08

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1 year ago

TrannyOne

18, first time
05:45

First time with Big Dick Tranny

3 years ago

BeMyHole

first time
07:01

Tranny cop first time Sex With a Sneaky Stripper

1 year ago

TrannyOne

amateur, teen (18+), strip, first time
06:17

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3 years ago

ShemaleTaxi

first time
05:58

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2 years ago

TrannyOne

first time
12:04

Hot lad gets his hairy ass stretched by the stunning TS chick

4 years ago

BeMyHole

hairy, natural, first time
05:07

Dude for the fist time has tranny up his arse

5 years ago

Analdin

swinger, party, fetish, fisting, first time
16:17

His very first time with a trans, did he like it?

1 year ago

ShemaleTaxi

blowjob, couple, tattoo, first time
33:17

His first time with a shemale

1 year ago

xHamster

vintage, domination, first time
12:30

Is this your first time with a Brazilian shemale

5 years ago

xHamster

brazil, first time
06:00 75%

Latina teen shemale first time fucked her girlfriend

6 years ago

AShemaleTube

girlfriend, first time
02:23

My first time

2 years ago

AShemaleTube

first time
10:45

Me fuckn my asian CD for first time bronx

5 years ago

xHamster

first time
05:07

Dudes first time ass fuck making out with shemale

4 years ago

Analdin

deepthroat, first time
10:24

Tiny mangos tranny First Time butthole Kimber Films

6 years ago

ShemaleZ

small tits, first time
11:06

Bearly Legal Fem Boy Sucks Dick On Camera For The First Time 18 Year Old Facial

10 months ago

TXXX

first time
22:34

Fucked For The Very First Time

3 years ago

TXXX

big tits, first time, shemale fucks guy
05:30

Petite Thai ladyboy first time anal fuck POV style

4 years ago

ShemaleZ

first time
15:58

I Will Make Your Very First Time With A transgirl Memorable

3 years ago

TrannyGem

first time
05:45

Petite Asian First Time Fucked By A Transgender - Ivory Mayhem And Kimmy Kimm

10 months ago

ShemaleZ

first time
07:49

Fucked for the Very First Time

3 years ago

AShemaleTube

domination, first time
32:51 80%

French tgirl : his first time with a sexy dicky girl

3 years ago

AShemaleTube

french, outdoor, ass to mouth, shemale and girl, blonde, first time
06:14

Inexperienced Boy Sucking An Ass For The First Time, Smeared Himself All Over

10 months ago

BeMyHole

selfsuck, first time
05:10

Pierce Paris and Janelle Fennec first time anal scene sex in the bedroom

4 years ago

ShemaleZ

anal, piercing, first time
06:09

Casting Nubian TS Strokes her Fat Cock

5 years ago

TrannyGem

casting, fat, shaving, first time
15:56

SOMEONES spunking

3 years ago

ShemaleTaxi

goth, taxi, first time
03:06

GROOBYGIRLS: Debuting Princess Genevieve

4 months ago

TrannyGem

first time, heels
20:04

Alex Castano Teen Transsexual Gets Fucked First Time

1 year ago

Upornia

teen (18+), first time
12:05

Beauty Fucks For Her First Time With A Trans And Its With Spencer Bradley

1 year ago

ShemaleZ

amateur, beauty, shemale and girl, first time
11:46

Uber-cute she-creature very first time SISSYGASM after make up and stroking

2 years ago

ShemaleMovie

cute, french, first time
05:10

Sexy Ladyboy Tarja Lou Fucks The First Time

1 year ago

ShemaleZ

first time
03:00

First Time Straight Mexican Pounds Blonde Sissy

1 month ago

AShemaleTube

homemade, creampie, crossdresser, mexican, first time
22:53

His first time with a tranny

10 years ago

xHamster

first time
05:59

Busty teen sheshaft first time takes big cock

3 years ago

BeMyHole

first time
09:38

My first time

5 years ago

AShemaleTube

homemade, first time
05:29

Amateur Ladyboy Quin First Time Here

10 months ago

ShemaleZ

first time
09:39 82%

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

9 months ago

KeekAss

crossdresser, ass licking, first time
32:23

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

3 years ago

TrannyGem

group, first time
20:45

First-ever time stud with t-girl

2 years ago

TrannyGem

first time
18:49 69%

Unseen Hook-Up Movies Cumpilation - Onlyfans Veronica Sanders

7 months ago

TrannyGem

homemade, blowjob, POV, anal, russian, interracial, shemale and girl
06:15

Beauty Spencer Bradley Fucks For Her First Time With A Trans And Its

1 year ago

GetTranny

first time
17:36

Fucking first time!

5 years ago

xHamster

first time
04:48

Bunny Porks Her Bootie For Dominatrix Molly

1 year ago

TrannyGem

femdom, lesbian, first time
53:13

First Time butthole couple Sex

1 year ago

TrannyOne

shemale, couple, masturbation, first time
22:00

Ts In Stockings Ingrid Moreira The First Time

2 years ago

BeMyHole

piercing, condom, shaving, first time, shemale fucks guy
12:14

Amateur shemale first time on cam

6 years ago

ShemaleZ

first time
15:16

Crossdresser first time Dressing for man

6 years ago

ShemaleZ

dress, first time
12:20

You will never leave behind your very first time with shemale Mel

2 years ago

ShemaleMovie

bisexual, first time
17:46

I pulverize a she-creature woman for the first-ever time 4k

2 years ago

TrannyGem

squirt, first time
06:33

T-Girl for very first Time Fuck-Fest - KimCock

3 years ago

TrannyGem

public, squirt, first time, FTM
14:59

Steaming youthful Tgirls very first time on smash machine before I jism all over her face!

3 years ago

KeekAss

machine, first time
06:01

First Time Tranny Guest Anally Fucked In The House

3 years ago

BeMyHole

kissing, cute, 69, first time
28:17

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

8 months ago

xHamster

homemade, ladyboy, first time, shemale fucks guy, latina
18:34

Hung Trans Keira Verga fucks her fan for the first time

2 years ago

PornHub

anal, latina, heels, first time, hardcore, brunette
05:56

Transsexual Fatty Blows Dick First Time 6 Min

5 months ago

ShemaleZ

first time
10:13

Real Transgender Gal Gets Ass-Fuck Smash

11 months ago

TrannyGem

homemade, teen anal (18+), british, sissy, first time, teen (18+)
21:05

Hot shemale fucks for first time her boyfriend

2 years ago

TrannyOne

first time, boyfriend
10:28

Boy very first time with trans

3 years ago

HDSex

first time
05:56

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5 years ago

IcePorn

cum in mouth, surprise, first time
05:41

Tranny for first-ever Time Intercourse - Kimcock

5 years ago

TrannyGem

handjob, blowjob, anal, threesome, ladyboy, ass, gape
05:29

Elegant transsexual gets fucked by a guy for the first time

10 years ago

AShemaleTube

amateur, first time
23:44

First-Ever time for my spouse shag with She-Creature Total (Free-For-All Flick)

9 months ago

KeekAss

handjob, POV, asian, first time
14:28

My first time with a 24 cm dildo and cumming like a sissy

8 months ago

xHamster

dildo, first time
01:47

German Boy cums fast FIRST TIME VACUUM he came twice

2 years ago

xHamster

german, 18, first time
06:06

My first time with a trans. Part 1 While my friend rests

9 months ago

xHamster

homemade, teen (18+), big cock, first time
06:14

Trans Khloe Kay licks Aiden Ashley pussy first time

5 months ago

AShemaleTube

first time
09:43

Beautiful Tbabe Seduces Hot Stud To Fuck Her Ass

2 months ago

BeMyHole

beauty, first time
09:11 89%

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

6 months ago

TrannyGem

fat, anal, interracial, 18, bareback, first time

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