SHEMALE • FIRST TIME 670 videos

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33:02

Guy with Fat Cock Fucks Latina Tranny in the Ass for the First Time on Vacation

3 months ago

$$ FapHouse

shemale, fat, cumshot, big cock, ass, first time
15:50

Bambi mess serves her owner, Miss Sunshine for the first time throughout webcam.

5 years ago

ShemaleTaxi

first time
20:56 71%

Very first time deep throating and smashing … $$$

1 month ago

ShemaleMovie

first time, crossdresser, shemale, deepthroat, 18
20:15

First Time ass Penetration For t-girl Adria

6 years ago

ShemaleZ

interracial, first time
26:24

First-Ever Time BIG BLACK COCK

6 years ago

TrannyGem

BBC, first time
20:45

First-Ever Time donk Foray For t-female Adria

5 years ago

TrannyGem

cute, interracial, first time
15:19

Its my first-ever time letting a shemale rail my penis

4 years ago

KeekAss

penis, first time, threesome
17:25

Young guy fucked for the first time by a tranny

4 years ago

AShemaleTube

first time, crossdresser, homemade
22:15

Very first time hand-job given by an exotic dark spotted girl

1 year ago

ShemaleMovie

shemale and girl, shemale, first time, BDSM, facesitting
21:09

JUGANDO CON MI VECINA TERMINO FOLLANDOLA Y ELLA ORDEÑANDO MI PENE.

9 months ago

TrannyGem

feet, cute, blowjob, creampie, lesbian, gagging
16:30

Femdom tgirl initiation: first time fuckers

3 years ago

TrannyOne

femdom, first time, BDSM
22:22

FTM Transman Ethan Hawk Gets Leg Trembling~FIRST TIME BBC!~interracial Trans Big Ass! Big Dick!

4 years ago

TrannyOne

first time, FTM
1:29:53

741m584-g02 My Son Who Came Back For The First Time In

2 years ago

ShemaleZ

first time
15:12

This is my first time as a crossdressing sissy

3 years ago

ShemaleTaxi

panties, first time
17:38

Thatha oliver em sua primeira cena. trans muito linda e voluptuous fodendo gostoso e com belos peitos naturais...ts very beautiful, sexy and with incredible natural cupcakes [ts thatha oliver] very torrid

9 months ago

ShemaleTaxi

beauty, brazil, ass licking, natural, babe, first time
53:15

Trans Vanessa Jhons welcome Gonzo first time double ana

4 years ago

TrannyOne

first time, double penetration, interracial
15:48

This is my very first time crossdressing like this

3 months ago

ShemaleMovie

masturbation, crossdresser, shemale, first time
18:28

Its time you tasted your very first ladyboy sausage

6 years ago

KeekAss

compilation, handjob compilation, first time
20:08

MY very first TIME FUCK wonderful shemale ON UPSTAIRS

2 years ago

ShemaleTaxi

creampie, BDSM, cuckold, first time
1:38:41

My Very First Time With A Trans (Total clothespins)

5 years ago

TrannyGem

full movie, first time
20:45

First Time ass Penetration For t-girl Adria

7 years ago

ShemaleZ

ass, first time
24:10

Full Version of My First Time Using a Chastity Cage for My Trans Big Penis

1 month ago

$$ FapHouse

mexican, chastity, first time
26:08

Very first time for a young dude but its a trap! Shes a shemale...

8 months ago

ShemaleMovie

italian, anal, first time
39:01 74%

A curious woman tries a shemale's cock for the first time

3 years ago

xHamster

shemale and girl, first time
1:01:26

Pretty trans girl new toy first time anal play on cam

8 years ago

TXXX

dildo, first time
17:03

Teds Ride With Wendy Santos, The Naughty Trans Gives A Blowjob In The Car

1 year ago

BeMyHole

natural, audition, car, riding, first time
15:03

No.290 Suleika Latex fucks a sissy anal slut (first time)

5 years ago

TXXX

latex, slut, first time
19:12 88%

CD TRANSSEXUAL FIRST-EVER BIG BLACK COCK !! HE CAME INWARDS of Me TWO TIMES!!! WARM PUBLIC SISSY

3 years ago

TrannyGem

public, dogging, BBC, first time, crossdresser
17:13

Legacy dirt:She on the porn first time, her lucky day. P3

3 years ago

ShemaleTaxi

thai, asian, skinny, taxi, first time
16:29

Your first-ever time with a transgirl will be extraordinaire

6 years ago

KeekAss

group, handjob compilation, first time
16:00

Guy having his first time with Geneva and Gina Ryder

6 years ago

ShemaleZ

vintage, first time
31:02

Humungous schlong girlfriend pounded for the very first time

4 years ago

ShemaleTaxi

girlfriend, first time
16:39

Female dom transsexual Initiation: first Time Fuckers

5 years ago

ShemaleTaxi

facesitting, domination, first time
18:28

Its time you tasted your very first transgirl trouser snake

5 years ago

TrannyGem

first time
21:02

Platinum-blonde tranny IN crimson LINGERIE TRY BIG LATINA COCK FIRST TIME

2 years ago

ShemaleTaxi

latina, domination, first time
19:09

I am a Cute Ladyboy in Mini Skirt and My White Beautiful Body

10 months ago

XXXDan

cute, beauty, public, teen (18+), dance, massage, compilation
33:13

Joanie - My very first flick - Part 1

8 months ago

ShemaleMovie

lingerie, crossdresser, sissy, first time, femboy, amateur
16:26

This is my first time pulverizing a t-girl babe

5 years ago

ShemaleTaxi

first time, shemale and girl
15:03

Giant stiffy arms free-for-all cum shot in underwear and matching rump buttplug

4 months ago

TrannyGem

big ass, orgasm, monster, big cock, close up, surprise, first time
30:08

Trans chick plays with an legal cm fuck stick for the first time, Moans from pain but ends up liking it Succubo16

2 months ago

ShemaleMovie

crossdresser, solo, sissy, BBW, first time, chubby
15:03

Big dick hands free jizz shot in underwear and matching rump plug

2 months ago

ShemaleMovie

ass, hands free, first time
30:05 75%

White tranny takes BBC for first time

6 years ago

TXXX

interracial, BBC, first time
21:53

Venezuela transsexuals romping For The first-ever Time!

5 years ago

VideoSection

bisexual, spanish, first time
36:57

Lizzy Yums bathing solo session with anal toys and edging for the first time

2 months ago

XXXVogue

masturbation, first time, anal, dildo
15:35

I Will Make Your First Time With A Shemale Unforgettable

2 years ago

BeMyHole

first time
17:31

Office tart going knuckle deep first-ever time

3 months ago

TrannyGem

amateur, sissy, first time, fisting, pantyhose, office
29:48

Alluring Shemales Fuck Each Others Tight Puckered Assholes

8 years ago

Analdin

swallow, tight, asshole, first time, brunette
22:37

SHEMALE LADYBOY POKES HETERO FELLOW - FIRST-EVER TIME TS SMASHING

3 years ago

KeekAss

first time, shemale fucks guy
26:49 60%

Fucking A T-girl For The First Time With Renata Barbosa And Fernandinha Fernandez

1 year ago

HClips

shemale and girl, shemale, big ass, ass licking, first time
24:53

Deep Digging In The Big Ass Of Beautiful Brat With A Big Dick First Time With Yago Ribeiro

11 months ago

ShemaleZ

beauty, creampie, big ass, big tits, lingerie, ass licking, ass
15:58

I will make your first-ever time with a she-creature never-to-be-forgotten

5 years ago

TrannyGem

first time
22:58 84%

AI-nosey - sequence 1: first-ever Times (Big Johnson)

4 years ago

ShemaleTaxi

cartoon, taxi, first time, shemale
15:38

Mr Hankeys Dragon Fake Penis Review & Pulverize - PLUMPER Pulverizes Trans Gf w/ HUMUNGOUS Strap Dildo - Sydney Groans

3 years ago

TrannyGem

BBW, screaming, penis, first time
18:15

FEMALE DOMINATION HANDBALLING ASS FUCKING INSTRUCTING PEGGING DOMINATRIX SUPREMACY FEMBOY

4 years ago

TrannyGem

femdom, train, instruction, wife, fisting, dildo, pegging
15:08

GLORIUS PUSS ATTEMPT VERY FIRST TIME GAINT TRANSGENDER PRINCESS FUCK-STICK

4 years ago

KeekAss

lesbian, first time
20:35

She-creature Nicky Bermudez wants a youthfull guy to pound her ass - FAKings

3 months ago

ShemaleTaxi

spanish, anal, big ass, orgasm, ass to mouth, ass, deepthroat
16:18

ADULT TIME - T-Girl Brittney Kade Fufills Besties Bucket List Fuck By Topping Him Licking His Ass

3 months ago

JizzBunker

shemale and girl, first time, ass licking, hardcore
24:08

First-Ever time dual foray after 25 days sans rubbin myself. I cant get enough! Stoner fav.

4 months ago

TrannyGem

feet, amateur, double penetration, first time
17:09 57%

Lovely big ass vixen horny xxx scene

9 months ago

Analdin

amateur, orgasm, shemale and girl, ass, slut, first time, anal orgasm
1:40:20

My first time with a tranny (Full HD Version - Director

3 years ago

xHamster

orgasm, full movie, first time, story
22:32

My First Time!

1 year ago

BeMyHole

teen (18+), couple, teen anal (18+), big tits, 18, first time, hardcore
29:38

My First Time

1 year ago

xHamster

latina, first time
16:16

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

1 year ago

VideoSection

first time
44:17 92%

Kendall Penny - Southern Sass Submits For The First Time!

3 years ago

ShemaleZ

stockings, fetish, BDSM, ass, first time, brunette
23:12

GORGEOUS BRUNETTE WITH WET PUSSY TASTE SHEMALE COCK FIRST TIME

3 years ago

xHamster

creampie, shemale and girl, wet, first time
18:28

Its time for you to try your first shemale cock

1 year ago

XXXDan

first time
15:40

Trans lady humps Herself With Her Brand fresh Dildo in the Shower

5 months ago

ShemaleMovie

anal, amateur, dildo, feet, first time
28:43

Raphaella Ferrari In The First Time Of The Incredible

11 months ago

ShemaleZ

cumshot, big tits, first time, blowjob, shemale
32:48

Joanie-my first video-part 2

1 year ago

JizzBunker

first time
19:20

German Sissy Ron first Vid

11 months ago

XXXDan

shemale, crossdresser, latex, first time, sissy, german
23:43

First Time Double Penetration After 25 Days Without Touching Myself. I Cant Get Enough! Stoner Fav

2 years ago

ShemaleZ

fetish, first time, double penetration
16:02

Get ready for your first time with a transsexual

1 year ago

XXXDan

shemale, lingerie, first time
16:12 72%

Stephie scarlet first time pegging a tgirl

2 years ago

IcePorn

pegging, first time, amateur
26:23

Shemale fucks Petite transgirl for the first time in the New Year

1 year ago

xHamster

shemale, first time
18:22

First-Ever time ever! Twunk Femboy very first sesh ass fucking teaching with Knotted Mutt Fuck Stick Part 1!

3 years ago

TrannyGem

huge dildo, first time
15:08

CindiCsissy eating my own cum for the first time

3 years ago

xHamster

redhead, small tits, first time
19:13 60%

My First Time

1 year ago

ShemaleZ

stockings, shemale, creampie, shemale and girl, blonde, first time
15:38

Mr Hankeys Dragon Fake Penis Review & Plow - PLUMPER Penetrates Trans Gf w/ THICK Strap Dildo - Sydney Yells

3 years ago

TrannyGem

BBW, screaming, penis, first time
16:29

Your first-ever time with a t-girl will be amazing

6 years ago

TrannyGem

gangbang, first time
39:01

A nosey nymph attempts a trannys man rod for the first-ever time

3 years ago

KeekAss

lesbian, first time, shemale and girl
4:12:46

Oots-015 Sensitive Cosplayer Who Gets Her Anus Penetrated And Writhes In Agony. Anal Masturbation, Deep Throat, Sensitive, First Time Filming, Female Orgasm, Ahegao, Lesbian, Anal Sex, Lotion Play, Pov, Doujinshi, Cosplay, Cosplayer, Big Cock, 3p, Fa

5 months ago

ShemaleZ

teen (18+), lesbian, POV, teen anal (18+), orgasm, lingerie, first time
17:43

Gothic crossdresser nubile very first time toying with fake penis and jizzing all over herself

3 years ago

TrannyGem

teen anal (18+), penis, first time
26:08

First-Ever time BIG BLACK COCK

6 years ago

TrannyGem

BBC, first time
15:12

This is my first time as a crossdressing sissy

3 years ago

ShemaleTaxi

first time, crossdresser
15:01

Playing With An Uncle Who Is Having Sex With A Transsexual For The First Time With A Big Dick. 15 Min

2 years ago

Upornia

uncle, first time
15:09

My very first time as a sissy was so liberating

3 years ago

ShemaleTaxi

panties, first time, sissy
15:56 81%

RUSSIAN FEMBOY TEARS UP WITH DOMME FOR THE VERY FIRST TIME WITH a YAM-SIZED BELT DICK, STRAPPED WITH a INNOCENCE

4 years ago

TrannyGem

femdom, strapon, mature anal, russian, fisting, bondage, pegging
15:26 77%

ADULT TIME - Best First Date Ever! Casey Calvert Gobbles Up T-Girl Leilani Li & Takes DEEP Creampie!

11 months ago

xHamster

big ass, shemale and girl, shemale, first time, creampie
16:12

Get ready for your first time with a t-girl

3 years ago

ShemaleTaxi

couple, first time
15:16 60%

Hands Free Hot Cumshot Big Load Cute Ladyboy Shemale Sissy Femboy Trap

10 months ago

XXXDan

cute, teen (18+), dance, couple, compilation, caught, college
16:02

Get ready for your first time with a tranny

4 years ago

xHamster

couple, JOI, first time
27:19

Busty Crossdresser First time on Chaturbate

7 years ago

AShemaleTube

first time
17:39

Huge Cock Ts Shemale Fuck Latina Teen Girl First Time

4 years ago

Upornia

shemale and girl, first time, mom
23:07

First Time sheboy Sex Virgins

7 years ago

ShemaleZ

first time
58:50

My first time witnessing her thrust a dildo in that tight caboose

4 years ago

ShemaleMovie

tight, first time, dildo
48:04

Fuck machine anal, 6 Toys! With 2 limp clitty cum shots

3 years ago

xHamster

latex, mature anal, machine, first time
35:25 67%

The first-ever Time Married to a Trans damsel

7 months ago

ShemaleMovie

POV, tattoo, crossdresser, babe, BBC, sissy, first time
15:56

My First-Ever Time Having Hookup With a Ts Gal

10 months ago

TrannyGem

cumshot, cartoon, first time, amateur, 18, story
15:10 54%

Thai girl taste big shemale cock first time

2 years ago

xHamster

thai, first time, asian
16:21

Hot Pre Cumming Masturbation Cute Ladyboy

9 months ago

XXXDan

compilation, teen (18+), cute, first time
56:43

SWEET ANGIE 2020-09-10 she does nothing -good for first time

5 years ago

xHamster

cute, first time
19:37

My first-ever Time with chick fellow

10 months ago

ShemaleMovie

shemale, shemale fucks guy, big cock, first time
17:48

Dive into the World of Sizzling Sensuality: Exploring the Alluring and Captivating Side of Seduction

8 months ago

JizzBunker

teen (18+), first time, compilation, beauty, dance, seduced
17:32

Crossdresser sissy training her thight ass

3 years ago

xHamster

public, train, vibrator, first time
25:05 45%

Pumped Anal Prolapse! First Time Huge Butt Plug Fitted!! - Male Escort - Book Me On

2 years ago

ShemaleZ

solo, pump, first time, escort, toys
15:17

Crossdressing for the first time senses so liberating

3 years ago

ShemaleTaxi

lingerie, panties, first time, crossdresser
15:19

Thai chick taste large she-creature cock first time

2 years ago

ShemaleTaxi

thai, taxi, first time, creampie
17:39 88%

Huge Cock TS Shemale Fuck Latina Teen Girl First Time

5 years ago

xHamster

teen (18+), german, bisexual, teen anal (18+), 69, asshole, first time
16:12

Prepare for your first time with a she-male

3 years ago

ShemaleTaxi

first time
18:07

Nympho Transgirl First Time With Enormous Bad Dragon//ruined Orgasm

4 years ago

HClips

orgasm, tattoo, first time, brunette
20:07

Skitty In My First Time With A Machine

3 years ago

Upornia

machine, first time
17:57

THIS new lingerie exhilarates ME SO MUCH THAT I MASTURBATE MERCILESSLY WHILE IMAGINING MY STEPBROTHERS PENIS.

10 months ago

ShemaleMovie

pantyhose, emo, chubby, BBW, 18, panties, penis
16:02

Acquire Prepped For Your Very First Time With A ladyboy

4 years ago

TrannyGem

first time
20:12

AMO VESTIRME DE MONJA Y TORTURAR MI BUM PARA VER MI MAN-LAVA REGADO EN TODA LA HABITACION

4 years ago

TrannyGem

nun, dress, first time
15:16

My first time being a sissy was so satisfying

3 years ago

ShemaleTaxi

crossdresser, first time
18:19 79%

Barbie Femmes Dont Need A Ken. They Have Their Own Peckers

1 year ago

TrannyGem

teen (18+), creampie, 18, shemale and girl, masturbation, big cock, babe
26:01

First-Ever time with a Bad Dragon - Demogorgon - phat rock hard, kinky rail

4 years ago

TrannyGem

russian, gape, first time
33:12

Joanie-my first video-part 1

1 year ago

XXXDan

first time, vibrator
15:39

Transgender princess first time with sex gal

3 years ago

ShemaleMovie

homemade, cartoon, first time
19:20

German Sissy Ron first Vid

3 years ago

xHamster

german, JOI, first time

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