SHEMALE • FIRST TIME 3,374 videos

Popular Latest Top rated

04:30 82%

Topping a guy friend for the first time!!!

3 years ago

TrannyOne

first time
11:21 80%

First time with a

3 years ago

TrannyOne

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08:12 63%

My first time with a transsexual

1 year ago

JizzBunker

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05:18 81%

Boy had first-ever time rectal with shemale

5 years ago

VideoSection

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10:28 67%

Boy very first time with trans

4 years ago

HDSex

first time
03:20

First Time Femboy

1 month ago

SomePorn

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09:51 65%

Homemade, escort meeting! My first Bi sex with Bia from the magic couple! Only those who have gone out with both of us know how good it is!

1 month ago

SunPorno

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34:12 50%

Watch fine-looking Silvana Lee and Lizzy Laynezs porn

4 months ago

PornHat

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06:54 79%

Getting dominated and sucking cock for the first time like a little slut with facial

2 years ago

TrannyOne

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14:56 58%

Domme T: first-ever Time rope-On Virgin

1 year ago

ShemaleTaxi

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08:19 74%

First Time Taste Drink My Own Cum. Handjob And Double Cum

1 year ago

xHamster

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29:01 86%

Ts Bianca (bibibratx) top for the first time with Cristiano

2 months ago

AShemaleTube

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05:29 51%

Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson

5 years ago

xHamster

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08:00 73%

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

1 year ago

GetTranny

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08:23 58%

Straight Guy Fucked By Trans Woman For First Time

2 years ago

ShemaleZ

big cock, first time
18:51 92%

Fucked by a man for the first time.

4 years ago

ShemaleZ

POV, first time, asian, teen (18+)
31:37 80%

Shy Couple first time shemale experience 2

5 years ago

AShemaleTube

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10:36 70%

My First Time With My New Ejaculating Fantasy Dildo

1 year ago

BeMyHole

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14:29 62%

College Amateur Aubreys first Porn

6 years ago

TrannyGem

car, swallow, college, first time, shemale
16:11 64%

Is this your first time fucking a hot tranny

3 years ago

TrannyOne

first time, amateur
08:07 81%

I try my transsexual friends cock for the first time

1 year ago

PornDr

handjob, beauty, shemale, blowjob, german, wife, cumshot
51:27 66%

Little ones first time - all 3 angles

5 years ago

TXXX

asian, bareback, first time, amateur
07:42 67%

He Wears My Panties For The First Time Pov - Teaser Video

1 year ago

GetTranny

panties, first time
08:00 58%

Christmas orgy first time Slumber Party

6 years ago

IcePorn

teen (18+), first time, party
21:06 74%

Hot guy gets his ass plowed for the first time by a nasty shemale beauty

3 years ago

TrannyOne

first time, beauty
08:09 73%

My very first time

3 years ago

TrannyOne

first time
10:00 74%

Boy first time with tranny

13 years ago

xHamster

first time
03:53 76%

Old man first time with shemale

5 months ago

AShemaleTube

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06:15 87%

Getting Dominated And Sucking Cock For The First Time Like A Little Slut With Facial 7 Min

2 years ago

ShemaleZ

stockings, small cock, POV, facial, domination, slut, first time
08:00 62%

741m584-g03 My Son Who Came Back For The First Time In

1 year ago

GetTranny

hairy, japanese, first time, asian, 18
32:36

Unleash your creativity as we embark on a thrilling journey together

1 month ago

XXXVogue

public, compilation
08:53

Crossdressers First Time

1 year ago

IcePorn

crossdresser, first time
09:48

Sexy she-creature ideal bum tweaking till she cums

4 days ago

ShemaleMovie

big cock, homemade, first time
06:05 75%

Your First Time Getting Fucked By A Trans Girl: First Date Gfe Pov Femdom

1 year ago

ShemaleZ

femdom, shemale and girl, webcam, first time, solo, POV
22:08 80%

Trans screwing a heterosexual boy for the first-ever time

7 months ago

ShemaleTaxi

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08:58 72%

First time swallowing cum

9 months ago

AShemaleTube

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17:35

Young dude screwed in the ass for the first time by a tranny

4 years ago

ShemaleMovie

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06:20 60%

Teenager Trans and Beau very first Ravage

4 years ago

TrannyGem

teen anal (18+), first time
21:59 83%

Trans nailing a heterosexual stud for the first-ever time

1 year ago

TrannyGem

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08:15

First-ever time fuck for a teenage shemale

5 years ago

VideoSection

first time
01:28

Casting Guy First Time - Itzelxxx

1 year ago

TXXX

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06:24

Lovely babe Cadence experiences her first time sucking a transgender dick with Natalie Mars

2 months ago

XXXVogue

first time
06:10

Newcomer femboy amateur jerking cock for the first time

2 months ago

XXXVogue

femboy
14:09

Latvian sissy crossdresser Ally enjoys her first time with a dildo

2 months ago

XXXVogue

femboy
32:17 82%

Helena Price - First Time With A Ladyboy Hd

3 years ago

ShemaleZ

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03:25 47%

Teenie Ginger-Haired uses a String on for the First-Ever Time!(more Content Coming Shortly)

1 year ago

TrannyGem

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12:00 80%

Naughty Michael Delray fucks tranny for the first time

1 year ago

YourLust

stockings, big cock, first time
03:08 93%

Porking Crossdresser For The Very first time in my life

7 months ago

KeekAss

amateur, crossdresser, first time, anal, blowjob
07:59

First Time Topping - T4t Intimate Cute

1 month ago

xShemaleTube

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13:25

His very first time with a ladyboy

6 years ago

HDSex

asian, nylon, first time
05:17 57%

VRB TRANS First time date with hot small tits shemale VR Porn

4 years ago

AShemaleTube

first time, shemale fucks guy
11:33

This Is Our First Time Fucking A Trans Babe

3 months ago

BeMyHole

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19:38

My First-Ever Time with CHICK MAN

7 months ago

TrannyGem

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15:57

The first time

1 year ago

AShemaleTube

amateur, POV, first time
08:58 57%

First Time swallowing cum

6 years ago

xHamster

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10:01

That boy had first time sex with an experienced milf tranny

10 years ago

MyLust

first time
23:47 67%

Guys first Time with Tgirl

3 years ago

TrannyOne

69, first time
03:03

Im transroxy, Ladyboy tears up a dark-haired with a thick donk no condom

4 weeks ago

TrannyGem

latina, shemale fucks guy, shemale, blowjob, first time, creampie, cum in ass
06:30

First-time shemale Jesse Pony gets screwed by petite she-creature Kasey Kei

2 months ago

XXXVogue

first time
18:23 75%

Barbie Girls Don't Need A Ken. They Have Their Own Dicks

10 months ago

xHamster

teen (18+), blowjob, shemale and girl, cumshot, first time, creampie
05:13

Lena And A Married Males First Time

2 years ago

TXXX

amateur, POV, first time
06:24

Khloe Kay, transsexual beauty, tastes Aiden Ashleys pussy for the very first time

2 months ago

XXXVogue

first time
18:47

The Pill Episode 2 - Chris First Time

1 year ago

JizzBunker

babe, first time
16:00 84%

Femdom Ts Initiation: First Time Fuckers

4 years ago

ShemaleZ

femdom, threesome, first time, fetish
08:15

Guy is first time topped by shemale wife

2 months ago

AShemaleTube

shemale, first time, wife
05:58

First time teen experience Janine smashing an older guy

3 years ago

TrannyOne

first time, teen (18+)
08:44 40%

Crossdressers First Time

3 years ago

TrannyOne

crossdresser, first time
17:35

Fresh guy experiences first time sex with a shemale

2 months ago

XXXVogue

homemade
17:30

Young guy gets fucked in the ass for the first time by a trans

11 months ago

JizzBunker

mature, shemale, mature anal, couple, ass, first time
19:52 86%

Shemale teen with big schlong lets stud shag her in the ass

1 month ago

ShemaleMovie

ass, skinny, sissy, first time, shemale fucks guy, cum in ass
08:27

Draped ladyman Surprise sucky-sucky vibration First-Ever Time

4 years ago

TrannyGem

surprise, vibrator, first time
06:20

Watch busty tgirl Emma Rose her first time sex with a woman

8 months ago

AShemaleTube

first time, shemale, blowjob, redhead
05:17 53%

Cd and Str8 First time

6 years ago

TXXX

first time
06:01

Inked homo plowed passionately for first time by Asian TS

3 years ago

TrannyOne

first time
28:10 78%

My Trans Girlfriend Fucks Me For The First Time. She I Love How She Fucks My Ass

1 year ago

ShemaleZ

amateur, redhead, girlfriend, first time
08:01

Skinny tight small tits teen and anal squirt first time Then he asked

3 years ago

TrannyOne

squirt, first time
05:54

Bashful French sissy first-ever time to fellate

2 years ago

ShemaleTaxi

french, taxi, sissy, first time
08:01

Rough violent gangbang crying first time Sometimes it takes a stranger

3 years ago

TrannyOne

stranger, first time
14:09 67%

Venus Lux Fucks First Time Bottom JakeD

1 year ago

IcePorn

first time, shemale fucks guy
14:51 77%

Sophie & Quinns Very First Time

3 years ago

KeekAss

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34:39 56%

Trans plowing 2 gals for the first time ~KimberlyGeorge~

2 years ago

VideoSection

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15:00 71%

Lustful shemale incredible porn movie

1 year ago

XoZilla

small cock, shemale, first time, missionary
40:52 57%

Tall Trans dame penetrated humid By Tiny CIS Girl

7 months ago

ShemaleTaxi

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21:45

Guy first time with blonde Tgirl

14 years ago

AShemaleTube

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06:37

Lovely ebony shemale Honey Foxxx fucks a smooth guy for the first time

2 months ago

XXXVogue

ebony
03:20 62%

Homemade reality demonstrate butt assfuck

1 year ago

TrannyGem

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08:01 73%

Christmas family fun and duddys step daughter blackmail first time Au

3 years ago

TrannyOne

funny, first time
12:08 80%

My First Time With A Trans

2 years ago

BeMyHole

amateur, big tits, ass licking, first time, hardcore
10:25

First time experience

2 months ago

XXXVogue

group
08:01

Blonde teen tied to bed first time Her vag was eventually broken to th

3 years ago

TrannyOne

teen (18+), tied, first time
03:48

Blonde gurls first time.

5 years ago

ShemaleZ

teen (18+), couple, blonde, first time
46:35

First Time With A Shemale

4 years ago

BeMyHole

first time, stockings
13:51

Linda novinha parece uma Boneca, teve o cuzinho arrombado e gostou

3 weeks ago

VideoSection

first time, shemale, anal, beauty
18:06

Sexually Attractive TS And Straight Guy Go At It For The First Time! - Shemale

3 years ago

HomemadeXXX

amateur, first time
06:15

First time with a Shemale Escort

3 years ago

TrannyOne

first time, escort, mature
06:14 75%

First time with a Shemale Escort

5 years ago

AShemaleTube

mature, lingerie, first time, escort, latina
16:52

My first Time

3 years ago

TrannyOne

first time
16:43

Feels Like The First Time . . .

4 years ago

xHamster

first time
06:50

First Time Bbc For Cute Ts

1 year ago

GetTranny

cute, first time, interracial
06:41

Husband and wife explore a shemale for the first time

2 months ago

XXXVogue

husband
15:59 50%

Tranny shag a white fellow in donk

3 years ago

TrannyGem

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44:37

First time having sex with a trans woman Linda

2 months ago

XXXVogue

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17:25

Young guy fucked in the ass for the first time by a tranny

4 years ago

xHamster

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06:10

Curious trans newbie strokes on casting couch for the first time

2 months ago

XXXVogue

casting
05:55

Shemale Creampies Guy for the first Time

5 years ago

ShemaleZ

first time
02:28 56%

Sissy Lexie Adams Crossdresser First Time with Sex Machine

2 years ago

xHamster

stockings, crossdresser, machine, sissy, first time
08:05

Noobie TS Fany Menezes First Time Machine Sex

2 months ago

SomePorn

solo, 18, first time, dildo
06:20

Teen guy sucking tranny cock first time

3 years ago

TrannyOne

teen (18+), first time
03:41 61%

Anonymous Random Grindr Fuck - First Time With Trans

1 year ago

ShemaleZ

amateur, stockings, creampie, bareback, first time
06:25

Trans beauty Sarah Oliveira fucks a dudes ass for the first time ever

2 months ago

XXXVogue

first time
06:25

Thai shemale Polla with a massive dick penetrates a guys ass after he drilled her for the first time

2 months ago

XXXVogue

first time
06:09

Casting Amateur Tgirl Deepthroating Dick

6 years ago

TrannyGem

casting, POV, audition, first time
14:09

This will be our very first time drilling a t-girl

5 years ago

VideoSection

first time
06:15

We had a first time threesome with a tranny woman

2 years ago

TrannyOne

reality, first time, threesome
10:52

THE YOUNG MANS FIRST TIME EATING A PUSSY, I LET HIM CUM INSIDE ME COMPLETELY ON RED

Today

BeMyHole

swallow
11:30

Beauty Fucks For Her First Time With A Trans And Its Korra - Spencer Bradley And Korra Del Rio

2 years ago

TXXX

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06:50

Beautiful Local Girl Hardcore sex with Bf for the First time

7 years ago

AShemaleTube

first time
05:56

Amateur Tgirl First Time On Cam

6 years ago

ShemaleZ

first time
13:04 83%

She made me cum twice! first-ever time boinking Britney from Tantaly - Emily Adaire

1 year ago

ShemaleTaxi

stockings, shemale, german, solo, cumshot, big cock, first time
11:33

Crossdresser CD Blows Straight Boy first Time Candicane

4 years ago

AShemaleTube

first time

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