SHEMALE • FIRST TIME 744 videos

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16:29

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

6 years ago

TrannyGem

gangbang, first time
24:08

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

8 months ago

TrannyGem

feet, amateur, double penetration, first time
20:56 75%

Very first time deep throating and smashing … $$$

5 months ago

ShemaleMovie

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17:43

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4 years ago

TrannyGem

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26:08

First-Ever time BIG BLACK COCK

6 years ago

TrannyGem

BBC, first time
39:01

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

4 years ago

KeekAss

lesbian, first time, shemale and girl
41:08

Anna Hickhiman - Big Tit Latina Anna Fucks Stranger In The Ass For The First Time And Squirts

4 months ago

ShemaleZ

big ass, shemale, latina, squirt, first time
15:40

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

9 months ago

ShemaleMovie

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15:12

This is my first time as a crossdressing sissy

3 years ago

ShemaleTaxi

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28:43

Raphaella Ferrari In The First Time Of The Incredible

1 year ago

ShemaleZ

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16:12

Get ready for your first time with a t-girl

3 years ago

ShemaleTaxi

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16:02

Get ready for your first time with a transsexual

1 year ago

XXXDan

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15:09

My very first time as a sissy was so liberating

3 years ago

ShemaleTaxi

panties, first time, sissy
39:01 73%

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

4 years ago

xHamster

shemale and girl, first time, bisexual
19:13 60%

My First Time

1 year ago

ShemaleZ

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27:19

Busty Crossdresser First time on Chaturbate

7 years ago

AShemaleTube

first time
25:54

First Time Blackcock

3 years ago

HClips

interracial, tattoo, first time
17:39 80%

Huge Cock Ts Shemale Fuck Latina Teen Girl First Time

4 years ago

Upornia

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58:50

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

5 years ago

ShemaleMovie

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16:02

Get ready for your first time with a tranny

5 years ago

xHamster

couple, JOI, first time
26:23

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

2 years ago

xHamster

shemale, first time
15:16 60%

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

1 year ago

XXXDan

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15:26 78%

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

1 year ago

xHamster

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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, asian
15:56

My First-Ever Time Having Hookup With a Ts Gal

1 year ago

TrannyGem

cumshot, cartoon, first time, amateur, 18, story
15:17

Crossdressing for the first time senses so liberating

3 years ago

ShemaleTaxi

lingerie, panties, first time, crossdresser
16:21

Hot Pre Cumming Masturbation Cute Ladyboy

1 year ago

XXXDan

compilation, teen (18+), cute, first time
17:32

Crossdresser sissy training her thight ass

3 years ago

xHamster

public, train, vibrator, first time
15:19

Thai chick taste large she-creature cock first time

3 years ago

ShemaleTaxi

thai, taxi, first time, creampie
16:12

Prepare for your first time with a she-male

4 years ago

ShemaleTaxi

first time
19:37

My first-ever Time with chick fellow

1 year ago

ShemaleMovie

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35:25 57%

The first-ever Time Married to a Trans damsel

11 months ago

ShemaleMovie

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25:05 45%

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

3 years ago

ShemaleZ

solo, pump, first time, escort, toys
20:07

Skitty In My First Time With A Machine

3 years ago

Upornia

machine, first time
16:02

Acquire Prepped For Your Very First Time With A ladyboy

5 years ago

TrannyGem

first time
18:07

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

5 years ago

HClips

orgasm, tattoo, first time, brunette
17:39 75%

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
17:48

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

1 year ago

JizzBunker

teen (18+), first time, compilation, beauty, dance, seduced
15:16

My first time being a sissy was so satisfying

3 years ago

ShemaleTaxi

crossdresser, first time
26:01

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

4 years ago

TrannyGem

russian, gape, 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
17:57

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

1 year ago

ShemaleMovie

pantyhose, emo, chubby, BBW, 18, panties, penis
48:04

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

4 years ago

xHamster

latex, mature anal, machine, first time
52:59

Trans Vanessa Jhons Welcome To Gonzo With First Time Double Anal Sz2489

5 years ago

Upornia

fetish, double anal, gangbang, first time, double penetration
18:19 78%

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
33:12

Joanie-my first video-part 1

2 years ago

XXXDan

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15:39

Transgender princess first time with sex gal

4 years ago

ShemaleMovie

homemade, cartoon, first time
17:49

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5 years ago

ShemaleTaxi

teen anal (18+), first time
15:07

GLORIUS PUSSY TRY FIRST TIME GAINT SHEMALE COCK AND LOVE IT

5 years ago

AShemaleTube

first time
19:33

Sissy Bimbo Brandynette First Time Caged showing off her new Lovense toy

6 years ago

ShemaleZ

18, first time
19:20

German Sissy Ron first Vid

4 years ago

xHamster

german, JOI, first time
16:11

Be gentle this is my first time with a transsexual

1 year ago

JizzBunker

interracial, lingerie, first time
33:20

First-time Dap For Phat Ass Trans Alves Ak001 - Goddess Julia And Julia Alves

2 years ago

ShemaleZ

double anal, first time, double penetration
17:12

Throbbing cock TS tranny pound latina teen girl First Time

5 years ago

ShemaleZ

first time, shemale and girl
16:19

First time with a hot shemale

4 years ago

TrannyOne

first time
15:08

GLORIUS LABIA ATTEMPT VERY FIRST TIME GAINT T-GIRL DICK AND ENJOY IT

4 years ago

KeekAss

first time, lesbian
26:27

Rocco Steele And Trip Richards In First Time With A Trans Guy

4 years ago

HClips

tattoo, first time, brunette
19:31

My First Time Double-Anal And Footjob In New Lingerie

6 years ago

TXXX

teen anal (18+), footjob, double anal, first time, double penetration, creampie
15:16

My very first time being a sissy was so satisfying

3 years ago

ShemaleTaxi

panties, taxi, first time
36:34 71%

First time with my Hismith machine

4 years ago

TrannyOne

machine, first time, stockings
15:08

My First Time With Big Tranny One-eyed Snake

2 years ago

ShemaleZ

first time
20:49

First time in bondage

2 years ago

xHamster

latex, shemale, japanese, masturbation, first time
17:38

DVaBoi Femboy Sissy First Time Dildo Sesh

5 years ago

BeMyHole

first time, femboy
2:31:59

Danna Valentina 20200828 very first time i catch jism

3 years ago

ShemaleTaxi

latex, caught, taxi, first time
30:21

Sequel to Pegging of Sissy tart for the first Time

2 years ago

ShemaleTaxi

massage, bathroom, pegging, taxi, first time
15:56

RUSSIAN FEMBOY HUMPS WITH DOMME FOR THE FIRST-EVER TIME WITH A IMMENSE BELT DICK, STRAPPED WITH A INNOCENCE

4 years ago

TrannyGem

femdom, strapon, russian, pegging, first time, chastity, femboy
17:27

Sissy uses Lube for the first Time and Absolutely Loves It!

7 years ago

TrannyGem

ass to mouth, shaving, first time
15:18

GLORIUS labia try very first TIME GAINT SHEMALE COCK

2 years ago

ShemaleMovie

first time
17:06

My Taut Good-Sized Trap Bum vs Mr Hankey Dominic Pacifico BIG BLACK COCK Fake Penis

3 years ago

TrannyGem

huge dildo, dildo, penis, first time, BBC
15:08

Suleika Spandex ravages a sissy buttfuck bi-atch (first-ever time)

4 years ago

TrannyGem

spandex, dutch, first time, sissy
17:17

Trans gal fills thick fuck stick in culo. First-Ever time on camera. (Utter Uncircumcised)

3 years ago

TrannyGem

huge dildo, first time
17:43

Gothic crossdresser teenager first-ever time toying with fuck stick and jizzing all over herself

4 years ago

TrannyGem

first time
23:21

Stellar dark-haired WITH WET PUSSY TASTE SHEMALE COCK first TIME

3 years ago

ShemaleTaxi

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17:32

Crossdresser sissy teaching her thight bum

3 years ago

TrannyGem

public, vibrator, first time, crossdresser
20:46

First time sucking and fucking … $$$

4 years ago

AShemaleTube

first time
16:20

Is this your first time plowing a red-hot she-male

4 years ago

ShemaleTaxi

bisexual, first time, hardcore
15:16

My first-ever time as a sissy was nicer than I ever imagined

4 years ago

ShemaleTaxi

first time
18:15 86%

FEMALE DOMINATION HANDBALLING ASSFUCKING INSTRUCTING PEGGING DOMINATRIX PREDOMINANCE FEMBOY

4 years ago

TrannyGem

femdom, train, instruction, wife, fisting, bondage, dildo
16:43

Femboy Uses dildo For The first-ever Time (reupload)

4 years ago

ShemaleTaxi

first time, dildo
20:07

Skitty in My very first time with a Machine

4 years ago

KeekAss

latex, machine, first time, crossdresser
18:22

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

3 years ago

KeekAss

first time
15:58

I will make your first time with a shemale unforgettable

7 years ago

xHamster

first time
17:46

Fuckin very first time!

5 years ago

HDSex

first time
15:08

Cindicsissy Eating My Own Cum For The First Time

3 years ago

ShemaleZ

first time
19:18

Nerdy Glasses - Enby Fisting Their Ass For First Time. My Asshole Is Still Too Tight. Cum Many Times

3 years ago

ShemaleZ

fisting, tattoo, glasses, tight, asshole, first time
28:23

Trans Girl Fucks A Space Unicorn Cock For The First Time!

3 years ago

ShemaleZ

first time
18:33

Femboi On Cam For First Time 19 Min

3 years ago

ShemaleZ

first time
36:34

First Time With My Hismith Machine

4 years ago

ShemaleZ

redhead, machine, first time
20:57

Gaping My Tight Hole With An Xl Dildo For The First Time, Broke My Mind And My Ass 21 Min

3 years ago

Upornia

dildo, tight, gape, first time
15:15

Small Tits ladyboy Leticia Keren Gets Machine drilled for The first-ever Time

2 years ago

ShemaleTaxi

machine, taxi, first time
17:43

Gothic crossdresser teenage first-ever time toying with faux-cock and nutting all over herself

4 years ago

KeekAss

first time, crossdresser
32:58

Theresa Si getting prepped for her first-ever camshow, very first time toying with the ESCA wand experience dirtytalk and smash

4 years ago

KeekAss

first time
25:08

Anal invasion Bumper very first Time

3 years ago

ShemaleMovie

first time
15:18

GLORIUS vag attempt first TIME GAINT SHEMALE COCK

4 years ago

ShemaleTaxi

first time
18:51

My first time cross dressing

4 years ago

ShemaleTaxi

crossdresser, dress, first time, femboy
18:07

DVaBoi Femboy Sissy first Time fake penis Sesh

4 years ago

ShemaleTaxi

penis, first time
16:29

Your first time as a sissy will be amazing

4 years ago

TrannyOne

first time
24:14

Marina s 1st Almere Visit

2 years ago

XXXDan

mature anal, fisting, first time
16:59

First Time The Whore Crawls By His Cock

2 years ago

ShemaleZ

amateur, first time, 18
15:06

Smallish Fun Bags Transgender Princess Leticia Keren Gets Machine Nailed for The First-Ever Time

2 years ago

KeekAss

first time
15:16

My first-ever time as a sissy was better than I ever imagined

1 year ago

ShemaleMovie

amateur, crossdresser, sissy
18:05

DVaBoi Femboy Sissy very first Time fuck stick Sesh

5 years ago

ShemaleTaxi

first time, femboy
15:08

CindiCsissy eats my own cum for the first time

1 year ago

JizzBunker

shemale, first time
37:05

Young boy fucks a transsexual for the first time

2 years ago

JizzBunker

first time
36:59

Young Guy Fuck The First Time A Shemale

2 years ago

ShemaleZ

blonde, first time
29:52

Trans Girl Plays With An 18 Cm Dildo For The First Time Moans From Pain But Ends Up Liking It Succubo16

2 years ago

ShemaleZ

dildo, first time
23:03

First time Sissy MixyXXX training FIST with hands free orgasm!

2 years ago

AShemaleTube

pantyhose, orgasm, fisting, first time, hands free
30:08

Trans woman plays with an eighteen cm Dildo for the first time, Moans from pain but ends up luving it Succubo16

2 years ago

ShemaleTaxi

first time
18:01

DVaBoi Femboy Sissy first-ever Time dildo Sesh

2 years ago

ShemaleMovie

first time
16:39

First Time Using A Butt Plug Riding Dick

2 years ago

ShemaleZ

first time
17:18

Gothic Crossdresser Teen First Time Playing With Dildo And Cumming All Over Herself

2 years ago

ShemaleZ

first time
20:36 57%

First time working out with new gym buddy - Emily Adaire fucks new Tantaly sex doll

1 year ago

XXXDan

beauty, doll, german, orgasm, solo, masturbation, close up
36:30

First time with my machine

2 years ago

AShemaleTube

first time, crossdresser, stockings
21:19

First time in bdsm xhzqzzu

1 year ago

AShemaleTube

first time
23:46

Her first-ever time with a transgender princess

1 year ago

ShemaleMovie

big cock, shemale, shemale and girl, stockings
18:36

Shorts and Sass: Unleashing Confidence in Crossdresser Fashion!

1 year ago

JizzBunker

dance, crossdresser
32:27

Fun and Fabulous: Join Me on My Creativity Journey

1 year ago

XXXDan

teen (18+), crossdresser, shemale, masturbation
26:35

Crossdressing Confessions: Sharing My Personal Stories and Experiences!

1 year ago

XXXDan

big cock, masturbation
15:33

He Wears My Panties For The First Time Pov

2 years ago

ShemaleZ

panties, first time
1:29:51

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

2 years ago

ShemaleZ

cum in mouth, first time, asian

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