SHEMALE • FIRST TIME 3,342 videos

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05:33

Torrid japanese Trans Ys first-ever time with huge

1 year ago

ShemaleMovie

japanese, first time
05:14 82%

Trans has her first time with her step cousin

1 year ago

ShemaleTaxi

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04:48

Super-Naughty Japanese Trans Lady Attempting Out A Tenga Egg Masturbator For The Very First Time

1 year ago

KeekAss

first time
11:05

Ladyboy pummels brand fresh. It was his first-ever time

1 year ago

KeekAss

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

1 year ago

ShemaleZ

dildo, first time
09:46

LIL Young Transgirl Sissy gets RODE by wall plaything for the VERY FIRST TIME

1 year ago

TrannyGem

dildo, college, sissy
36:59

Young Guy Fuck The First Time A Shemale

1 year ago

ShemaleZ

blonde, first time
15:39

Trans Girl Fucks Herself With Her Brand New Dildo in the Shower

1 year ago

PornHub

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27:40

Spectacular latin redhead gets her first bisexual tranny penetrate

1 year ago

ShemaleTaxi

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05:22 47%

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1 year ago

xHamster

3D, first time, hardcore
04:51

Guy First Time Dressed as Woman and Strapon Fuck

1 year ago

xHamster

strapon, dress, first time
02:44

Fledgling femboy rails plaything for first-ever time

1 year ago

KeekAss

crossdresser, first time, femboy
04:24

Sissy bjs and nails big black cock fake penis

1 year ago

TrannyGem

big cock, BBC, sissy
01:28

Casting Guy First Time - Itzelxxx

1 year ago

TXXX

casting, first time
01:21

Mirans First Time

1 year ago

TXXX

first time, mature
10:07

Barely legal yr elder ts nymph jacks for the very first time in her stepdads truck

1 year ago

KeekAss

first time
06:55

Legal yr elderly schoolgirl female screwing with the instructor for the very first time to pass the check-up

1 year ago

KeekAss

first time, crossdresser
05:13 88%

She fellates a thick FUTA salami for the very first time

1 year ago

TrannyGem

cartoon, cum in mouth, futanari, first time
01:21

Mirans First Time

1 year ago

xShemaleTube

mature, first time
04:13

Sugary-sweet she-male inserts a 25cm cucumber

1 year ago

TrannyGem

first time
02:10

MissAlinaPaige s First Time Sucking Cock TRAILER

1 year ago

AShemaleTube

first time
10:06

TRANSSEXUAL Teenage Leticia Keren Loves Her Very First Time with The Fuckin Machine

1 year ago

KeekAss

first time
03:11

FEMOUT.XXX: Welcome Wiki

1 year ago

xHamster

stockings, first time, polish
06:12

Jellygrave - This was my first time using a fleshlight. I

1 year ago

NuVid

first time, fleshlight
02:40

Obese White Femboy Rail for First-Ever Time Faux-Cock - Prompt Climax with Hefty Explosion

1 year ago

TrannyGem

cumshot compilation, chastity
10:16

My Only Time Being Bottom For a Ts Chick

1 year ago

TrannyGem

cartoon
05:55

Ladyboy Firsttimer Ploy Gets Fucked Bareback

1 year ago

BeMyHole

first time
06:45

I Record While I Fuck For The First Time With My Transsexual Girlfriend 20 Min

1 year ago

GetTranny

first time
05:37

Fresh Faced First Timer Gets Barebacked POV Style

1 year ago

BeMyHole

first time
07:13

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

1 year ago

GetTranny

first time, shemale fucks guy
08:39

First time this slave suck a cock

1 year ago

AShemaleTube

first time
01:37 36%

First time with my TS stepsister

1 year ago

xHamster

amateur, creampie, first time, shemale fucks guy
05:19

SexGodPicasso @VonMadeHaNut Bangs A T-Girl For The Very First Time

1 year ago

KeekAss

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10:20

Beautiful 18 year older trans dame penetrating for the first time with her new sex toy

1 year ago

ShemaleTaxi

first time, homemade
04:40

The First-Ever ASS FUCKING FEMBOY. Heavily flowing...

1 year ago

TrannyGem

first time
06:58

Sissy/trans For The First Time Decided To Fuck Her Ass With A Dildo 11 Min

1 year ago

GetTranny

first time
10:10

Beautiful 18 year old trans girl fucking for the first time with her new sex toy

1 year ago

xHamster

teen anal (18+), shemale and girl, bareback, first time
13:48

This Is Our First Time Having A Threesome With A TS

1 year ago

BeMyHole

first time
04:25

First-Ever ASS-FUCK practice!

1 year ago

TrannyGem

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04:09

Ravaging Fap Long with a giant fuck stick and going knuckle deep close up - Brief movie

1 year ago

TrannyGem

indian
10:30

KIRITO PLAYS WITH SLIT AND BACKSIDE IN GGO (SWORD ART ONLINE COSTUME PLAY) - TAYLOR RYDE

1 year ago

TrannyGem

first time, cosplay
03:17

Young sissy gets her muff demolished by BIG BLACK COCK

1 year ago

TrannyGem

dildo
03:49

Yummy Mercedes Has Sex With A Shemale For The First Time

1 year ago

GetTranny

first time
03:25 47%

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

1 year ago

TrannyGem

amateur, femdom, teen (18+), deepthroat, first time, femboy
08:00

Cd Tries Fucking Dildo For The First Time

1 year ago

GetTranny

first time
37:05

Young Guy fuck the first Time a Shemale

1 year ago

xHamster

first time
15:57

The first time

1 year ago

AShemaleTube

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12:13

Japanese crossdresser strokes off for the first time in two weeks

1 year ago

ShemaleMovie

japanese, first time
15:56

My Very First Time Having Bang-Out With a Ts Damsel

1 year ago

KeekAss

first time
05:57

Asian Ladyboy First Time Masturbating In Front Of Cam

1 year ago

ShemaleZ

first time
18:49 72%

Unseen Hook-Up Movies Cumpilation - Onlyfans Veronica Sanders

1 year ago

TrannyGem

homemade, blowjob, POV, anal, russian, interracial, shemale and girl
02:07

T-Model Latina cociendo con su faux-cock!

1 year ago

TrannyGem

first time
09:21

It was his first time with a trans, at first he was a little nervous, but he started to let

1 year ago

AShemaleTube

amateur, homemade, interracial, compilation, cum in mouth, first time
05:06

Masturbate Long rails a XXL spear and knuckles his cock-squeezing butt - Brief movie

1 year ago

TrannyGem

huge dildo, dildo, 18
05:52

Sucking Cock Dude Has His First Time With A Shemale Right After A Breakup

1 year ago

BeMyHole

first time
06:18

Ts Teen Leticia Keren Enjoys Her First Time With The Fucking Machine

1 year ago

GetTranny

teen anal (18+), first time
20:26

I Record While I Fuck For The First Time With My Transsexual Girlfriend 20 Min

1 year ago

ShemaleZ

redhead, first time
05:18

Ass Fucking pranks with fuck stick in blue g-string

1 year ago

TrannyGem

indian, huge dildo
12:47

Gorgeous Marilyn Johnson Experienced Sex With A Trans Girl For The First Time

1 year ago

BeMyHole

shemale and girl, erotic, first time
15:52

FTM Femboy - Solo Rectal Butt to Throat & DOUBLE PENETRATION in Fishnets

1 year ago

TrannyGem

ass to mouth, femboy
29:58

Trans Girl plays with an 18 cm Dildo for the first time, Moans from pain but ends up liking it Succubo16

1 year ago

xHamster

mexican, first time
28:31

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

1 year ago

ShemaleZ

first time, shemale fucks guy
05:25

Sissy/trans For The First Time Decided To Fuck Her Ass With A Dildo 11 Min - Teaser Video

1 year ago

GetTranny

first time, dildo
08:00

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

1 year ago

GetTranny

uncle, first time
08:39

First time he suck a cock

1 year ago

AShemaleTube

first time, mature
07:38

【男の娘】アナル開発中　くちゅくちゅオナニー聞いて

1 year ago

TrannyGem

first time
14:39 72%

Ride With A Beautiful And Wonderful Trans Isabella Salvatore

1 year ago

BeMyHole

beauty, big tits, car, riding, first time
04:13

Good-Sized assfucking buttplug and assfucking beads demolishing my butt-hole

1 year ago

TrannyGem

huge dildo, gape, anal orgasm, orgasm
18:24 74%

The very first time

1 year ago

AShemaleTube

mature, homemade, stockings, shemale, lingerie, crossdresser, sissy
03:11

BOBSTGIRLS: We're Thrilled to Introduce Amy

1 year ago

xHamster

dildo, first time
06:26

Asian Ladyboy First Time Masturbating In Front Of Cam

1 year ago

VipTube

first time
09:17

Frolicking with my sissy fem stud

1 year ago

TrannyGem

big ass
06:43 62%

White haired petite girl cording blowage on the table very first time (kinda fail)

1 year ago

ShemaleMovie

short hair, first time
38:29 64%

Moscardiniema - I Remember The First Time I Saw Manu On Social Media, I Was Laying In Bed And It Was About 11pm, I Literally Couldnt Believe My Eyes.

1 year ago

BeMyHole

stockings, big tits, blonde, first time, hardcore, 18
38:38

Sucking A Curious Woman Tries A Shemales Cock For The First Time

1 year ago

BeMyHole

shemale and girl, first time
08:46

Elliot Finns first-ever Time With Trans-stud Luke Hudson

1 year ago

ShemaleMovie

first time
08:00

Fun party turns into orgy first time Laundry Day

1 year ago

IcePorn

party, group, orgy, first time
04:53

First Time With My Transvestite Friend

1 year ago

ShemaleZ

first time
06:36

I Try A Butt Plug For The First Time 7 Min

1 year ago

Upornia

first time
08:46

Agatha Lira – JOI, first time doing it, I came by myself

1 year ago

IcePorn

JOI, first time
03:20 62%

Homemade reality demonstrate butt assfuck

1 year ago

TrannyGem

feet, homemade, big ass, brazil, first time
02:04

Sissy Femboy Bangs her Butt with 8 inch Shoving & Vibing Faux-Cock - Assfucking Have Fun

1 year ago

TrannyGem

BDSM, anal orgasm, chastity
18:47

The Pill Episode 2 - Chris First Time

1 year ago

JizzBunker

babe, first time
04:59

Trans Has Her First Time With Her Cousin

1 year ago

ShemaleZ

amateur, cousin, first time, colombian
04:35

Draped Married BWC Uses A Gloryhole For The Very First Time

1 year ago

KeekAss

gloryhole, first time, crossdresser
05:44

Aspen Brooks In Yummy Mercedes Has Sex With A Shemale For The First Time

1 year ago

ShemaleZ

first time
08:19 72%

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

1 year ago

xHamster

handjob, amateur, solo, first time
16:12 77%

Stephie scarlet first time pegging a tgirl

1 year ago

IcePorn

pegging, first time, amateur
08:06

Pretty Ladyboy First Time In Front Of Camera

1 year ago

Upornia

asian, first time
14:35 40%

Very first time unexperienced crossdresser gets jizz al over by sugar daddy

1 year ago

ShemaleMovie

orgasm, crossdresser, first time
10:43

Sissy/trans For The First Time Decided To Fuck Her Ass With A Dildo 11 Min

1 year ago

ShemaleZ

first time, sissy
13:19

Cd Tries Fucking Dildo For The First Time

1 year ago

ShemaleZ

first time
03:42

Crossdresser Daisy's first time out in the open .

1 year ago

xHamster

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01:26

Como si fuera la primera ves

1 year ago

xHamster

vintage, mexican, webcam, first time
09:41

Ts Teen Enjoys Her First Time With The Fucking Machine - Leticia Keren

1 year ago

ShemaleZ

first time
13:23

Skinny German Skinny Young Woman Amateur Tranny Celine Dijjon Gets Anal Fingered To Orgasm

1 year ago

BeMyHole

german, orgasm, 18, college, skinny, first time
08:42

Redhead tranny shemale as anal cowgirl: First Timer? - Lily Demure

1 year ago

xHand

anal, spanking, ass licking, first time, missionary
10:39

Crossdresser first time sucks cock gets fucked facial full sissy

1 year ago

PornHub

small cock, facial, sissy, first time
10:04

Leticia Keren In Ts Teen Enjoys Her First Time With The Fucking Machine

1 year ago

ShemaleZ

first time
44:47

Intercourse tourist romps a transgender princess for the first time

1 year ago

ShemaleMovie

first time
31:02

Big manhood gf fucked for the first time

1 year ago

ShemaleMovie

first time
04:59

First time with my transvestite friend

1 year ago

xHamster

first time
09:40

Fucking The Virgin Ass Of An 18 Year Old Boy For The First Time

1 year ago

ShemaleZ

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09:51

My first anal experience

1 year ago

xHamster

first time
15:35

I Will Make Your First Time With A Shemale Unforgettable

1 year ago

BeMyHole

first time
12:00

Naughty Michael Delray fucks tranny for the first time

1 year ago

YourLust

stockings, big cock, first time
08:00

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

1 year ago

GetTranny

hairy, japanese, first time
14:28

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

1 year ago

xHamster

dildo, first time
28:17

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

1 year ago

xHamster

homemade, ladyboy, first time, shemale fucks guy, latina, amateur
15:01

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

1 year ago

Upornia

uncle, first time
05:30

Ever See Straight Guy Fucks A Transexual For The First Time?

1 year ago

BeMyHole

first time
01:56

My first time i wearing high heels )

1 year ago

xHamster

russian, first time
02:58

Sissy sounding pathetic clitty for the first time

1 year ago

xHamster

french, BDSM, clit, first time
08:00

M584g01 Stepson Who Has Returned For The First Time In 5 Years Is A Transcendental Transsexual?

1 year ago

GetTranny

japanese, old and young (18+), first time
02:19

Desi Ass Licking Anal Punishment Dildo First Time

1 year ago

xHamster

dildo, first time
08:00 44%

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

1 year ago

GetTranny

japanese, cum in mouth, first time
02:11

Hermosa mujer blanca viene a mi casa y terminamos follando

1 year ago

TrannyGem

indian, arab, indonesian, first time
09:37

Fucking Trio Chloe Temple Gets Her Ass And Pussy Fucked At The Same Time On Her First Day At Work With Winter XX Doll

1 year ago

BeMyHole

threesome, gloryhole, bathroom, first time
07:05

My First Time With A Trans. Part 2

1 year ago

ShemaleZ

teen (18+), 18, first time
07:42

Small Tits TS Yris Star Enjoys Her First Time With The Fucking Machine

1 year ago

BeMyHole

first time

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