SHEMALE • FIRST TIME 528 videos

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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
18:07

DVaBoi Femboy Sissy first Time fake penis Sesh

3 years ago

ShemaleTaxi

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36:34

First Time With My Hismith Machine

3 years ago

ShemaleZ

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31:02

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3 years ago

ShemaleTaxi

girlfriend, first time
23:23

Fucked for the First Time

3 years ago

TrannyOne

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44:47

Fucky-fucky tourist plows a transgender princess for the first time

3 years ago

ShemaleTaxi

first time
16:19

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3 years ago

TrannyOne

first time
16:29

Your first time as a sissy will be amazing

3 years ago

TrannyOne

first time
22:22

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

3 years ago

TrannyOne

first time, FTM
18:22

Hung Trans Keira Verga Fucks Her Fan For The First Time

3 years ago

TrannyOne

first time, hardcore
32:49

Cassie Takes A Dragon For The First Time - Cassie Cummings

3 years ago

ShemaleZ

tattoo, first time
17:39

Huge Cock Ts Shemale Fuck Latina Teen Girl First Time

3 years ago

Upornia

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26:27

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

3 years ago

HClips

tattoo, first time, brunette
21:13

Venezuela Transsexuals Fucking For The First Time! 21 Min

3 years ago

Upornia

first time
22:32

First time BBC FTM Transman Ethan Hawk

3 years ago

xHamster

couple, BBC, first time, FTM
15:08

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

3 years ago

KeekAss

lesbian, first time
15:08

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

3 years ago

KeekAss

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22:34

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3 years ago

TXXX

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15:07

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3 years ago

AShemaleTube

first time
18:07

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

3 years ago

HClips

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17:25

Young guy fucked for the first time by a tranny

3 years ago

AShemaleTube

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58:50

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3 years ago

ShemaleMovie

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16:02

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4 years ago

TrannyGem

first time
16:02

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4 years ago

xHamster

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39:29

Sharnell Dupree - First-time Fantasy

4 years ago

TXXX

first time
43:15

First Time on Webcam

4 years ago

BeMyHole

first time
15:03

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

4 years ago

TXXX

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17:38

DVaBoi Femboy Sissy First Time Dildo Sesh

4 years ago

BeMyHole

first time, femboy
15:28

Brunette gets Pegged by Wife for the first Time

4 years ago

TrannyGem

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56:43

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

4 years ago

xHamster

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16:20

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4 years ago

ShemaleTaxi

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17:49

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4 years ago

ShemaleTaxi

teen anal (18+), first time
16:08

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4 years ago

ShemaleTaxi

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15:50

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

4 years ago

ShemaleTaxi

first time
16:26

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4 years ago

ShemaleTaxi

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18:05

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4 years ago

ShemaleTaxi

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17:46

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4 years ago

HDSex

first time
15:58

I Will Make Your Very First Time With A transgirl Memorable

4 years ago

TrannyGem

first time
17:12

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4 years ago

ShemaleZ

first time, shemale and girl
24:47

I m a crossdresser for the first time part 3

4 years ago

AShemaleTube

first time
16:20

Is this your first time banging a super-steamy transgender princess

4 years ago

ShemaleMovie

first time
16:39

Your very first time with a transgender princess will be extraordinaire

4 years ago

ShemaleMovie

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16:38

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4 years ago

ShemaleMovie

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15:48

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4 years ago

TrannyOne

dogging, first time
25:49

Futanaria First Time Fuck Buddies

5 years ago

ShemaleZ

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36:43

Kendall Penny - Submits for the First Time

5 years ago

ShemaleZ

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19:09

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5 years ago

ShemaleZ

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16:08

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5 years ago

HDSex

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22:17

Massive cumshot after Jade fucks her flesh light - first time buttplug

5 years ago

ShemaleZ

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37:10

Pixie and Rachael making out. First time

5 years ago

ShemaleZ

first time
38:59

First-Time Fantasy

5 years ago

TXXX

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16:20

Is this your first time penetrating a steamy t-girl

5 years ago

HDSex

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1:38:11

My First Time With A Trans (Full movies)

5 years ago

TXXX

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15:59

Amateur Shemale Nev Nomi puts her Fox Tail in for the first time!

5 years ago

ShemaleZ

first time
16:34

First time

5 years ago

ShemaleZ

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20:15

First Time ass Penetration For t-girl Adria

5 years ago

ShemaleZ

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19:31

My First Time Double-Anal And Footjob In New Lingerie

5 years ago

TXXX

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20:40

005 - My first time at Skype Hotel

5 years ago

AShemaleTube

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22:25

First Time Threeway with a Black Tranny Babe

5 years ago

ShemaleZ

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16:00

Guy having his first time with Geneva and Gina Ryder

5 years ago

ShemaleZ

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32:30

Susie Vicentini - First Time On Camera

5 years ago

ShemaleZ

tattoo, ass licking, first time
19:39

Lucimara Santos Pool teen First Time t-girl pound

5 years ago

ShemaleZ

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20:45

First Time ass Penetration For t-girl Adria

5 years ago

ShemaleZ

interracial, first time
19:02

First time anal (no sound)

5 years ago

TXXX

first time
17:27

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

6 years ago

TrannyGem

ass to mouth, shaving, first time
16:30

Guy having his first time with Geneva and Gina Ryder

6 years ago

AShemaleTube

18, first time
27:19

Busty Crossdresser First time on Chaturbate

6 years ago

AShemaleTube

first time
22:54

His First Time With A shetwink

6 years ago

ShemaleZ

first time
21:04

First Time Sthis chabmale Sex encounters

6 years ago

ShemaleZ

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20:45

First Time ass Penetration For t-girl Adria

6 years ago

ShemaleZ

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15:58

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6 years ago

xHamster

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19:39

Lucimara Santos Pool teen First Time t-girl pound

6 years ago

ShemaleZ

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23:07

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6 years ago

ShemaleZ

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23:44

Her first time with a shemale

6 years ago

ShemaleZ

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20:31

Blonde for the first time

6 years ago

ShemaleZ

first time
27:17

Cuties First Time With ladyboy

6 years ago

ShemaleZ

first time
16:29

Your first time with a tranny will be incredible

6 years ago

xHamster

gangbang, first time
16:11

Your first time with a transsexual will be an outstanding

7 years ago

JizzBunker

first time
16:19

First time

7 years ago

ShemaleZ

first time
15:16

Crossdresser first time Dressing for man

7 years ago

ShemaleZ

dress, first time
1:01:26

Pretty trans girl new toy first time anal play on cam

7 years ago

TXXX

dildo, first time
16:10

Your first time with a tranny will be outstanding

8 years ago

xHamster

first time
58:40

My first time seeing her shove a dildo in that tight ass

9 years ago

xHamster

dildo, tight, first time
18:17

First time with a tranny

10 years ago

xHamster

first time
22:53

His first time with a tranny

11 years ago

xHamster

first time
29:52

Lad has his first time with very hot TS

13 years ago

AShemaleTube

first time
18:03

Tran First Time On Camera

13 years ago

xHamster

first time
22:54

First Time Threeway with a Black Tranny Babe

15 years ago

AShemaleTube

black, babe, first time, interracial
19:20

German Sissy Ron first Vid

Today

XXXDan

shemale
15:27

ADULT TIME - hottest very first rendezvous Ever! Casey Calvert Gobbles Up T-Girl Leilani Li & Takes DEEP Creampie!

Today

ShemaleTaxi

shemale, creampie
15:16

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

5 months ago

ShemaleMovie

amateur, crossdresser, sissy
22:07

FIRST-EVER TIME WITH MY FRESH FUCK-FEST MACHINE ASS FUCKING

10 months ago

TrannyGem

solo, british, toys, first time, machine, cosplay
18:28

Its time for you to try your first shemale cock

10 months ago

XXXDan

first time
32:48

Joanie-my first video-part 2

11 months ago

JizzBunker

first time
16:16

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

1 year ago

VideoSection

first time
23:44

First-Ever time for my spouse screw with Transgender Princess Utter (Free-For-All Vid)

1 year ago

KeekAss

handjob, POV, asian, first time
15:06

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

1 year ago

KeekAss

first time
27:40

Spectacular latin redhead gets her first bisexual tranny penetrate

1 year ago

ShemaleTaxi

bisexual, brazil, first time
23:44

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

1 year ago

KeekAss

handjob, POV, asian, first time
18:01

DVaBoi Femboy Sissy first-ever Time dildo Sesh

1 year ago

ShemaleMovie

first time
33:51

Kendra Romans - First-Ever Time

1 year ago

KeekAss

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15:15

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

1 year ago

ShemaleTaxi

machine, taxi, first time
22:37

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

2 years ago

KeekAss

first time
18:22

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

2 years ago

TrannyGem

huge dildo, first time
18:22

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

2 years ago

KeekAss

first time
17:17

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

2 years ago

TrannyGem

huge dildo, first time
27:30

Beautiful brazilian redhead gets her first bisexuel tranny fuck

2 years ago

xHamster

bisexual, MILF, redhead, dogging, first time
16:43

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

2 years ago

ShemaleTaxi

first time
15:16

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

2 years ago

ShemaleTaxi

first time
19:20

German Sissy Ron first Vid

3 years ago

xHamster

german, JOI, first time
17:43

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

3 years ago

KeekAss

first time, crossdresser
17:43

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

3 years ago

TrannyGem

first time
26:01

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

3 years ago

TrannyGem

russian, gape, first time
20:45

First-ever time stud with t-girl

3 years ago

TrannyGem

first time
18:24

T-girl Alexandra naked for the 1st time,playing with herself

3 years ago

xHamster

mature, first time
18:34

Suspended Trans Keira Verga Bangs her Devotee for the first-ever Time

3 years ago

TrannyGem

heels, first time
15:19

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

3 years ago

KeekAss

penis, first time
21:43

Venezuela Ts’S Smashing For The First-Ever Time!

3 years ago

KeekAss

first time
15:58

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

4 years ago

TrannyGem

first time
18:28

Its time you tasted your very first transgirl trouser snake

4 years ago

TrannyGem

first time

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