SHEMALE • FIRST TIME 4,633 videos

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04:35 88%

Draped Married BWC Uses A Gloryhole For The Very First Time

2 years ago

KeekAss

gloryhole, first time, crossdresser, sissy
07:09

Brunette tranny ass licked and ass Fucked For The Very First Time 2 - Domino Presley

3 years ago

xTits

cheating, big tits, deepthroat, shaving, first time, missionary
21:06 74%

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

4 years ago

TrannyOne

first time, beauty
04:01

Sexy tgirl Gina James fucked by Christian for the first time

4 years ago

TrannyOne

first time, amateur
21:31 94%

Naughty man gets his sweet ass banged hard by the huge TS dick for the first time

4 years ago

TrannyOne

feet, heels, first time, fetish
10:28 70%

Boy very first time with trans

6 years ago

HDSex

first time, amateur
08:00

Teen braces facial compilation and licking orgasm first time

6 years ago

IcePorn

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05:31 54%

Cute TS in sexy lingerie first time fucked by BBC monster

6 years ago

ShemaleZ

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04:38 80%

Dude had first time anal with shemale

7 years ago

ShemaleZ

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08:00 58%

Hot teen banged doggy first time duddyly Family Competition

7 years ago

IcePorn

teen (18+), first time
04:03 50%

First Time in Drag

8 years ago

ShemaleZ

crossdresser, first time
12:44

Ladyboystar - Hottest tanned ladyboy likes getting nailed in high high-heeled slippers

1 month ago

ShemaleMovie

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13:04

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1 month ago

XXXVogue

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06:54

Hot BBW mummy gets dominated by Monster tranny Cock(HQ 3D Animation) 60 FPS

2 months ago

ShemaleMovie

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11:00

Beautiful japanese femboy Kelly in her very first xxx video

5 months ago

HDSex

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05:24

Gargle Her Meatpipe - Tgirl Manstick Fellating Encouragement - Imposed Bisexous

1 year ago

TrannyGem

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03:03

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

1 year ago

TrannyGem

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08:07 83%

TRANSSEXUAL Kim Wagner bangs a young homo, it is him first-ever time

1 year ago

TrannyGem

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29:51

Big Thighs White Shemale With Big Natural Tits Sexy Hot Horny Ladyboy

1 year ago

JizzBunker

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15:27 93%

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

1 year ago

ShemaleTaxi

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14:56 57%

Domme T: first-ever Time rope-On Virgin

2 years ago

ShemaleTaxi

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06:16 40%

She-Male Thippy & Noi first-ever time trio some

4 years ago

TrannyGem

first time, asian
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

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11:47

Gamer Girl Rides Her Step Mom Katrinas ginormous hermaphroditism salami on Live Stream

1 month ago

ShemaleTaxi

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12:25

Ladyboystar - Hard-core sans a condom bumfuck orgy with a killer transgender princess

2 months ago

TrannyGem

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10:05 43%

Instructing of a obedient Bitch, Fisting and Gape in the beaver

2 months ago

ShemaleTaxi

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05:10

TS Jessica Fox Submissive Surrender

2 months ago

Analdin

latex, feet, bondage, BDSM
08:32

Full salute Worship tease - Just Enough to Drive You ultra-kinky

3 months ago

ShemaleMovie

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16:08

Spouse with cunt and wifey run from Tikinhos contest.

4 months ago

TrannyGem

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14:49 60%

HALF PIPED - Trans Mom’s threesome orgy Adventure wt Hubbie & H

4 months ago

XoZilla

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05:16 60%

AI Generated Kida Nedakh Atlantis Futa goddess

5 months ago

ShemaleTaxi

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17:09 67%

Manmeat-fellating Lessons and freaky Sex: Stepbro Helps Stepsister Overcome Her Shyness and Get Even

10 months ago

ShemaleTaxi

blowjob, shemale, first time, shy
16:29

Tru Kait gave us her pussy to put our three jizz-shotguns and make a double penetration.

10 months ago

ShemaleTaxi

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08:30 63%

Fleshlight cumshots from the back plus assfuck blinking

1 year ago

ShemaleMovie

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07:34 73%

My very first Time in Winston-Salem, NC (TRANSSEXUAL PublicPrincess)

6 years ago

TrannyGem

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21:53

First Time Fucking with the Stunning Pastelle

1 month ago

$$ FapHouse

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10:09 50%

Young ginormous asian girl getting bred first time by a trans angel

1 month ago

ShemaleTaxi

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08:01

Its the very first time you showcase me your dinky

1 month ago

PornDr

french, blowjob, creampie, hardcore, first time
08:07

Emo trans girl gets fucked for the first time by a big man rod and gets super-naughty by being recorded

1 month ago

VideoSection

teen (18+), emo, old man, teen anal (18+), ladyboy, 18, shemale and girl
24:55

Agatha Mama In Teaching My Step Cousin How To Eat A Trans Woman For The First Time.

3 months ago

BeMyHole

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05:09 71%

Eva Lin First Time On Camera For An Intense Session Of Female Led Play

4 months ago

AShemaleTube

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15:39 60%

Mama Studio Presents Teaching My Step Cousin To Eat A Trans For The First Time - Free

4 months ago

BeMyHole

mom, blowjob, creampie, big ass, MILF, latina, ass to mouth
10:59

FIRST TIME WITH A TRANS WOMAN AND I ENDED UP GIVING HER MY ASS TO TRY IT OUT AND I LIKED IT - FULL

4 months ago

AShemaleTube

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14:47 50%

My Internet Friend Has Sex for the First Time with a Trans Girl and His Femboy Friend Gets All His Cum in His Face

4 months ago

$$ FapHouse

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28:11

Perverted Couple Hires A Shemale For The First Time For A Threesome

5 months ago

ShemaleZ

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11:00

Eva Nova - First Time CEI Encouragement JOI

6 months ago

NuVid

masturbation, solo, JOI, amateur
23:49

We Did an Interracial Threesome for the First Time with My Best Friend BBC

7 months ago

$$ FapHouse

interracial, cumshot, big cock, BBC, first time, colombian
07:59

Curious Guy Tries First Time Anal With A Tranny 10 Min - Very Beautiful, Victoria Di Prada And Victoria Carvalho

7 months ago

Fuxxx

first time
13:24 75%

Desi Village Girl Tight Pussy First Time Xxx Video, Desi Hot Beautiful Tgirl

11 months ago

DesiPornTube

beauty, amateur, indian, first time, tight
16:51 71%

Young Sexy Ladyboy First Time With Her Sugar Stepdaddy Suck Fuck Cum - Sugar Daddy

1 year ago

HClips

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16:56 64%

Young Sexy Ladyboy First Time with Her Sugar Daddy Suck, Fuck and Cum

1 year ago

$$ FapHouse

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06:41

Husband and wife explore a shemale for the first time

1 year ago

XXXVogue

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06:37 40%

Nymph gargles tranny dick for first time

1 year ago

ShemaleTaxi

masturbation, shemale, blowjob, first time, handjob
10:40 75%

I gave my bootie to my gigantic fuck stick for the first time

1 year ago

ShemaleTaxi

solo, 18, dildo, skinny, masturbation
12:06 68%

My First Time With A Trans

2 years ago

HClips

amateur, shemale, first time, blonde, blowjob
12:30 71%

Fems Very First time Sucking BIG BLACK COCK - G002

2 years ago

TrannyGem

asian, amateur, interracial, BBC, first time
10:11 91%

First Time Anal. Cute Tranny Plays With Herself. Squirt Orgasm

2 years ago

ShemaleZ

cute, squirt, orgasm, solo, toys, first time
15:57

The first time

2 years ago

AShemaleTube

amateur, POV, first time
04:59 80%

Trans Has Her First Time With Her Cousin

2 years ago

ShemaleZ

amateur, cousin, first time, colombian
28:17 86%

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

2 years ago

xHamster

homemade, ladyboy, first time, shemale fucks guy, latina, amateur
06:02 80%

Shemales2 And Orgy Premiere: Ashley Is Fucked By A Shemale And Swallows For The First Time Transsexual Sperm!

3 years ago

BeMyHole

teen anal (18+), sperm, swallow, group, orgy, domination, first time
03:41 76%

Anonymous Random Grindr Fuck - First Time With Trans

3 years ago

ShemaleZ

amateur, stockings, creampie, bareback, first time
10:25 83%

Jade Venus Is Meeting Her Mother-In-Law For The First Time And Her Pussy At The Same Time - Trans Angels

3 years ago

xHamster

mom, first time
11:09 79%

My first time with a shemale sexdoll from Tantaly

3 years ago

xHamster

pantyhose, doll, german, chubby, dildo, riding, natural
05:55 89%

Premiere: Ashley Is Fucked By A Shemale And Swallows For The First Time Transsexual Sperm! 6 Min With Ashley Cumstar And Rosella Extrem

3 years ago

ShemaleZ

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03:01 85%

FEMOUT XXX: Lemmi's First Time!

4 years ago

xHamster

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33:17 80%

His very first time with a she-creature

4 years ago

KeekAss

MILF, vintage, domination, first time, shemale fucks guy, anal
06:29 72%

The very first time he porks with a trans

4 years ago

ShemaleMovie

black, BBC, first time
06:15 60%

First time with a Shemale Escort

4 years ago

TrannyOne

first time, escort, mature
08:09 79%

My very first time

4 years ago

TrannyOne

first time
23:10 82%

Fucked For The First Time with Domino Presley

5 years ago

ShemaleZ

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05:09

Tight Ass Tgirl Gets Fucked For The First Time

7 years ago

ShemaleZ

tight, first time
05:01 89%

Tranny is trying Anal for the first time

8 years ago

AShemaleTube

first time, shemale, small tits, ladyboy, bareback, anal
17:59

First-ever time attempting a whisk in my bootie and it was mischievous!

3 days ago

KeekAss

big ass, solo
12:47

Ladyboystar - Long rectal drains and facial cumshot with a gorgeous Thia ladyboy

1 month ago

HDSex

shemale, POV, ladyboy, facial, first time, missionary
28:18 55%

Ts deepthroat, ts couple, ladyboy deepthroat

3 months ago

XXXVogue

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35:27

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3 months ago

XXXVogue

handjob, beauty, anal, massage, babe, gape, first time
12:37

Ladyboystar - Long butt sex jerks and facial cumshot with a handsome Thia shemale

3 months ago

TrannyGem

homemade, blowjob, POV, chubby, dogging, facial, jerking
04:09

Pinkish Harness Trans Female Fuckslut Rosy Crystal fuck stick part two Attempting Urinate for the First-Ever Time

10 months ago

TrannyGem

amateur, chubby, pissing, masturbation, dildo
34:12 80%

Milf Silvana Lee has Hardcore Sex with Her Brothers Sexy Shemale Girlfriend ...

1 year ago

Beeg

shemale, cuckold, first time, girlfriend, dogging, latina
07:45 83%

German first-timer 18yo she-male next door do homemade rectal pornography

1 year ago

TrannyGem

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19:52 90%

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

1 year ago

ShemaleMovie

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05:35 55%

Mini Skirt Cheerleader Schoolgirl Uniform Sissy Crossdresser Big Butt White Skin Shemale Big Ass

1 year ago

xHamster

teen (18+), massage, skirt, ladyboy, crossdresser
08:38 40%

My first and in my mouth.

1 year ago

xHamster

JOI, first time, cum in mouth, swallow
21:47 67%

TGIRLS.GONZO: Moscow Sweetie Gets Her Donk Humped

4 years ago

TrannyGem

russian, screaming, first time, anal
08:15

First-ever time fuck for a teenage shemale

6 years ago

VideoSection

first time, lingerie
13:35

Fucks girl, she-male, transgender

3 weeks ago

XXXVogue

beauty, 3D, british, anime, toys, first time, shemale and girl
12:27

Ladyboystar - Deep bumfuck and blowage fuckfest with a wondrous transgirl in black undergarments

1 month ago

TrannyGem

amateur, black, shemale, POV, dogging, facial, big cock
05:34 20%

Luna Atrracted Me With soles Fetish And Indian Futa With Her huge-titted milf Body

3 months ago

ShemaleMovie

indian, beauty, public, shemale, fetish, MILF, 3D
43:33 50%

I boink her bum with fantasy

3 months ago

ShemaleMovie

beauty, teen (18+), blowjob, massage, teen anal (18+), ladyboy, sissy
10:52

YOUNG TRANS GIRL LOST HER VIRGINITY AND RECORDED IT - COMPLETE ON RED - LUANA PRADO

7 months ago

BeMyHole

amateur, feet, teen (18+), POV, couple, fetish, teen anal (18+)
23:21

This Fit Trans Came To Cause Mischief On The City Streets On Her Birthday

8 months ago

BeMyHole

public, blowjob, car, domination, first time, hardcore
20:35

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

12 months ago

ShemaleTaxi

spanish, anal, big ass, orgasm, ass to mouth, ass, deepthroat
09:34 50%

POINT OF VIEW Your FTM Finest Buddy Takes Your Chastity

1 year ago

TrannyGem

cute, emo, POV, dildo, 18, riding, masturbation
30:27 86%

Skinny she-male gets insatiable anal fucked in the small ass

1 year ago

VideoSection

anal, asian, 18, ass, skinny, first time, missionary
03:42 67%

Summoners Legacy pt. three - Cherry futa got a highly enormous bone.

1 year ago

TrannyGem

cartoon, 3D, dirty talk, public, futanari
05:30 80%

Addiction Theropy pt. 11 - Scorching IG Model splattered all over my office with FUTA penis inwards her.

3 years ago

TrannyGem

squirt, 3D, office, wet, cartoon, futanari, penis
13:00 86%

Nur mit Gummi in den Arsch bitte

4 years ago

xHamster

mature, german, mature anal, teen anal (18+), swallow, first time, saggy tits
20:34

Alexa Castanos BBW Teen TS Ass Pounded First Time

1 month ago

JizzBunker

teen anal (18+), teen (18+), BBW
13:43

Muscular Guy Fucks a Trans Woman for the First Time!

1 month ago

$$ FapHouse

first time, cum in mouth, shemale
08:00

Gabizinha Trans Fucked Ftm For The First Time With Melissa Azuaga

1 month ago

Upornia

black, stockings, shemale, FTM
07:28 40%

Gabizinha Trans Fucked Ftm For The First Time With Melissa Azuaga

2 months ago

GetTranny

first time, amateur, ebony, FTM
07:00 57%

Small cock tiny tits Asian femboy teen first time raw anal fuck

2 months ago

AShemaleTube

small cock, blowjob, asian, ladyboy, first time, femboy
04:50 63%

First Time Meeting Kristi Kewt - Thad Maxxx

2 months ago

ShemaleZ

tattoo, first time, creampie, interracial
11:16

Trying A Shemale For The First Time In My Life! - Sassy Lux, Lina Paige And Wide Hips

3 months ago

Upornia

first time, shemale, big ass, solo, toys
06:49

Brand New Trans Cutie Pixie Pond Fucked By A Man For The First Time Ever

4 months ago

GetTranny

amateur, small cock, big cock, first time
38:14

Big Tit Tranny Kawane Fucks Guy In Tight Asshole For The First Time - Sabrina Suzuki, Alex Victor And Francine Munoz

4 months ago

ShemaleZ

tattoo, stockings, big ass, brunette, ass
06:14

Gorgeous Blonde Marilyn Johnson Fucks With A Trans Girl For The First Time

5 months ago

GetTranny

asian, stockings, first time, shemale and girl
10:57

YOUNG BOY HAD HIS VERY FIRST TIME WITH A TRANS - LUANA PRADO

6 months ago

KeekAss

shemale, first time
06:06 91%

Whats Russian For Suck My Cock? First Time Girl Fucked By Ts Teacher - Lora Hoffman

6 months ago

ShemaleZ

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05:09 80%

Sunshyne Monroe First Time Domination

6 months ago

AShemaleTube

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06:14 80%

Honey Foxxxs first time cum experience with big tits and intense pleasure

6 months ago

XXXVogue

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06:31 60%

First-time compilation of sexy undergarments and intense solo action

7 months ago

XXXVogue

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12:13

Secret santa Harin experienced a hard orgasm when she got an anal fisting for the first time and

7 months ago

AShemaleTube

shemale, crossdresser, stockings, orgasm
07:39

Bobbii Rose - gargles Huge Cock for very first Time

8 months ago

ShemaleMovie

big cock, cum in mouth, cum in ass
06:23

Immense, Shaggy TRANS Dame With ALL-NATURAL CUPCAKES BLASTS On Camera VERY FIRST TIME!!!

9 months ago

TrannyGem

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09:38 60%

His very first time with a sissy

9 months ago

ShemaleMovie

amateur, sissy, first time
28:17

Perverted Couple Hires a Shemale for the First Time for a Threesome

9 months ago

$$ FapHouse

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12:50

Innocent teen ladyboy first time on camera

9 months ago

AShemaleTube

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15:49 43%

Vol #3: torn up For The first Time on Femout

9 months ago

ShemaleTaxi

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