SHEMALE • FIRST TIME SEX 577 videos

Popular Latest Top rated

05:29 51%

Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson

5 years ago

xHamster

teen (18+), russian, first time, sissy, shemale and girl, crossdresser
09:47 94%

MILF Stepmom Let Stepsons TS GF Fuck Her Asshole

1 week ago

BeMyHole

ladyboy, first time, shemale and girl, big cock, kitchen, mom
04:10 82%

Transgender Lezzies Anal Invasion Screwing Up-Close From The Rear

5 months ago

TrannyGem

amateur, teen (18+), creampie, couple, teen anal (18+), dogging, crossdresser
06:20 64%

Teenager Trans and Beau very first Ravage

5 years ago

TrannyGem

teen anal (18+), first time
02:43 85%

Phat Dinky Trans Damsel Porks Gym Brother-In-Law + Face Tearing Up Deep Jaws

7 months ago

TrannyGem

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08:07 85%

I try my transsexual friends cock for the first time

1 year ago

PornDr

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20:04 93%

TGIRL POST-OP: Jenny Loves Her New Pussy Fucked

4 years ago

xHamster

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08:00 56%

Dass-133 First Time Nh Lesbian Sex. Kanami Kashiwagi Yu

2 years ago

GetTranny

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04:36 93%

Splendid Sissy Cherry Gets Roped Down And Creampied

9 months ago

TrannyGem

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08:26 92%

TRANS NYMPH GETS HUMPED BY ANOTHER TRANS DAME FOR THE FIRST-EVER TIME

1 year ago

TrannyGem

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06:21 80%

Fresh Zealand Inexperienced Transgender Female Gets Hard-Core Plumbed

8 months ago

TrannyGem

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14:56 58%

Domme T: first-ever Time rope-On Virgin

1 year ago

ShemaleTaxi

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25:51 60%

Five Cocks for her First Time

4 weeks ago

NuVid

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05:08 92%

Dude for the first time gets shemales male stick

6 years ago

Analdin

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12:21

First Time Feminized Means First Time Fucked in the Ass

8 months ago

xHamster

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08:17

Cool CHICA TRANS de GRAN bootie Motando Un ENORME chest

1 week ago

ShemaleMovie

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11:25 82%

Tearing Up My Trans GIRLFRIEND Cassie with a Mr Hankeys Fake Penis - HARDCORE PLUS-SIZE All Girl GG - PREVIEW - Sydney Moans

4 years ago

TrannyGem

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10:08 88%

Futa on Male where MILF-dickgirl and BitchBoy sedused boy for anal sex. Guy first time trying in the caboose and hatch.

2 years ago

ShemaleTaxi

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25:40

Ebony shemale and male Sub kinky sex

2 days ago

Analdin

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49:16 71%

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2 months ago

AShemaleTube

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10:36 72%

My First Time With My New Ejaculating Fantasy Dildo

2 years ago

BeMyHole

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06:23 87%

Transgender princess suntan first-ever Time Femboy

3 years ago

ShemaleMovie

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21:47 60%

TGIRLS.GONZO: Moscow Sweetie Gets Her Donk Humped

4 years ago

TrannyGem

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16:05 56%

Inexperienced real en motel de guerrero. pornography en español!

1 year ago

ShemaleTaxi

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32:50 71%

Gorgeous Darkhair Nasty Shemale Interracial Sex

5 years ago

Analdin

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10:11

Asian slut in tight crimson dress slams a battery switched strong vibrating dildo and moans a lot.

6 days ago

ShemaleTaxi

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09:34 57%

POINT OF VIEW Your FTM Finest Buddy Takes Your Chastity

4 months ago

TrannyGem

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08:06 67%

My First Time Have Sex With Black American Man

6 months ago

ShemaleZ

black, first time
09:43 40%

Fucking My Hot MILF Stepmom For The Firstime!

3 months ago

BeMyHole

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05:32 82%

Post-Op Thai Shemale Meiji Pussy Bareback

1 year ago

BeMyHole

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18:49 75%

Unseen Hook-Up Movies Cumpilation - Onlyfans Veronica Sanders

2 years ago

TrannyGem

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33:46 50%

Milf Silvana Lee Has Hardcore Sex With Her Brothers Sexy Shemale Girlfriend Lizzy Laynez Indoor

2 months ago

BeMyHole

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10:01 70%

That boy had first time sex with an experienced milf tranny

11 years ago

MyLust

first time
09:46 92%

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

2 years ago

TrannyGem

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11:09 75%

My first time with a shemale sexdoll from Tantaly

3 years ago

xHamster

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05:32

I came for the very first time

2 weeks ago

TrannyGem

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09:30 78%

Asian Transgirl Daniella Teas First Time Getting Fucked By A Guy On Video - Rough Sex

1 year ago

Upornia

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03:01 85%

FEMOUT XXX: Lemmi's First Time!

3 years ago

xHamster

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06:15

Young Asian ladyboy first time anal sex recorded on amateur video

2 days ago

AShemaleTube

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10:15 57%

Beautiful 18 yr elderly trans girl fucking for the first time with her new hook-up toy

1 year ago

ShemaleTaxi

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10:17 77%

Penetrated trans gf for the very first time

1 year ago

TrannyGem

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07:44

Evelyn Got into Me Our first-ever intimity on bed

4 weeks ago

ShemaleTaxi

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4:12:46

Oots-015 Sensitive Cosplayer Who Gets Her Anus Penetrated And Writhes In Agony. Anal Masturbation, Deep Throat, Sensitive, First Time Filming, Female Orgasm, Ahegao, Lesbian, Anal Sex, Lotion Play, Pov, Doujinshi, Cosplay, Cosplayer, Big Cock, 3p, Fa

5 months ago

ShemaleZ

teen (18+), lesbian, POV, teen anal (18+), orgasm, lingerie, first time
10:49

I WENT TO VISIT MY TRANS FRIEND AND WE HAD SEX FOR THE FIRST TIME I GAVE HER MY ASS AND TOOK CUM IN MY MOUTH

2 months ago

BeMyHole

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12:55

She made me jism twice! first time drilling Britney from Tantaly - Emily Adaire

3 months ago

ShemaleMovie

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06:02 76%

Filipino Femboy Has First Time Bareback Anal Sex On Camera

4 years ago

ShemaleZ

filipina, first time, femboy
08:42 85%

Redhead ladyboy Lily Demure crazy sex movie

2 years ago

XoZilla

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17:09 57%

Lovely big ass vixen horny xxx scene

9 months ago

Analdin

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13:00 83%

Nur mit Gummi in den Arsch bitte

4 years ago

xHamster

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08:07 60%

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

8 months ago

TrannyGem

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02:26

Daniela Lei first time no hands

1 month ago

AShemaleTube

shemale, stockings, hands free
53:13 57%

TScumshot.com first time anal couple sex tgirls

4 years ago

TrannyOne

couple, first time, BDSM
53:12 84%

First time anal couple sex blonde tgirl

6 years ago

AShemaleTube

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03:05 50%

Ravaging after experience

4 months ago

TrannyGem

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05:02 46%

Diva bitch-300 lovers in the future after this long wait!lol

4 years ago

xHamster

teen (18+), mature anal, muscle, teen anal (18+), first time, mature
03:32

Very First time letting my beau put it in my ass

2 months ago

TrannyGem

hardcore, amateur, first time
2:40:58 60%

Mooc-002 When I Met My Childhood Friend For The First Time In A Year, He Had Become A Yandere Girl. He Showed Me His Big Dick And I Got Aroused, So I Had Anal Sex With Him And Ejaculated Inside Him Over And Over Again. Hifumi Yuuri

7 months ago

ShemaleZ

big cock, shemale, asian, shemale and girl, first time
09:51 51%

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!

8 months ago

SunPorno

kissing, homemade, beauty, shemale, couple, fetish, wife
1:00:28 54%

She Is An Innocent Girl Who Is Having Sex For The First Time In A Year. The Old Mans Port Is Fully Erect As He Looks Very Shy. A Big Cock Is Stuck In The Vagina Hole For The First Time In A Year! Two Consecutiv

1 year ago

HClips

creampie, old man, POV, asian, shy, first time
17:09

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

1 month ago

ShemaleTaxi

blowjob, shemale, first time, shy
16:42 83%

I Recently Acquired A Giant Tentacle Dildo, And In This Video I Use It For The First Time

2 years ago

BeMyHole

amateur, stockings, dildo, solo, tentacle, first time
2:36:25 62%

Yui Hatano And Hibiki Otsuki - Dass-133 First Time Nh Lesbian Sex. Kanami Kashiwagi Yu

2 years ago

ShemaleZ

lesbian, asian, uniform, first time
21:59 84%

Trans nailing a heterosexual stud for the first-ever time

2 years ago

TrannyGem

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07:52

Trans lady gives her trans gf a blowage before getting her virginity taken

3 weeks ago

HDSex

anal, shemale, blowjob, lingerie
30:08

Trans chick plays with an legal cm fuck stick for the first time, Moans from pain but ends up liking it Succubo16

2 months ago

ShemaleMovie

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06:15 71%

Shemale fucked guy for the first time and she enjoyed hardcore anal sex

1 year ago

AShemaleTube

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14:17 77%

My First Time Sex with a Trans Girl!!!

7 months ago

$$ FapHouse

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20:36 57%

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

10 months ago

XXXDan

beauty, doll, german, orgasm, masturbation, big cock, close up
53:13 69%

First Time butthole couple Sex

2 years ago

TrannyOne

shemale, couple, masturbation, first time
08:00

Teen braces facial compilation and licking orgasm first time

5 years ago

IcePorn

teen (18+), orgasm, orgasm compilation, first time
19:38 20%

My First-Ever Time with CHICK MAN

1 year ago

TrannyGem

blowjob, creampie, double anal, first time, double penetration
15:00 63%

Lustful shemale incredible porn movie

1 year ago

XoZilla

small cock, shemale, first time, missionary
24:14 13%

Marinas 1st Almere Visit

3 years ago

TrannyGem

mature anal, fisting, dutch, heels, first time
12:36

Fucking my Trans GF Cassie with a Mr Hankey's Dildo

4 years ago

xHamster

kissing, strapon, lesbian, BBW, screaming, pegging, first time
11:39

First time porking a StarDust Dragon Amarok from desire Grove!! jiggling CUM!!!

4 months ago

ShemaleMovie

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14:17

Is this your first time in a shemale gangbang

4 years ago

xHamster

first time
16:16 50%

This is my first time fucking a shemale babe

5 years ago

xHamster

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11:38

Using a huge dildo, I had my first mind-blowing sissygasm and squirted all over while enjoying the cream

2 weeks ago

XXXVogue

squirt, massage, femboy
34:12 86%

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

6 months ago

Beeg

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02:21

Trans stunner nail immense guys donk

8 months ago

TrannyGem

fat, old man, big ass, latina, 18, old and young (18+), first time
10:25

Sissy schoolgirl my First time Fucking my Ass with a Sex Machine bbc fake penis

3 months ago

ShemaleTaxi

amateur, shemale, uniform, 18, glasses, masturbation, babe
06:15 75%

Jesse Pony first time having sex with a trans

2 years ago

UiPorn

first time
08:43

Tatitahilton FUCKING A TWINKY LITTLE 18 YEAR OLD FOR THE FIRST TIME

5 years ago

TrannyGem

18, first time
20:11 73%

Pretty young tdamsel butt drilled by girl for the first time

5 years ago

ShemaleTaxi

shemale, shemale and girl, taxi, first time
08:00

Life of the party first time Deep Throat Challenge

5 years ago

IcePorn

party, group, first time, POV
09:55

Japanese She-Male Daniella Teas First-Ever Time Getting Torn Up By A Boy on Flick

1 year ago

TrannyGem

first time, asian, interracial, anal, POV, japanese
13:04 83%

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

2 years ago

ShemaleTaxi

stockings, german, solo, cumshot, big cock, first time
06:14

Girl Alice trailer 02 (ultra broad twenty one:nine) ten part 1 (Glance originals by subscription) 4K UHD 60 FPS HDR

1 year ago

TrannyGem

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19:51 88%

T-Model teenager with yam-sized pink cigar lets dude plow her in the butt

3 years ago

TrannyGem

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06:15

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2 years ago

PornGem

first time
07:30

The First Time This Man Has Sex With A Trans

1 week ago

ShemaleZ

first time
3:05:31 38%

Hiiragi Kana And Alice Nanase In Dass-616 First Time Nh Lesbian Sex. First Time Ever, Ban Lifted. W Exclusive Special Kana Hiiragi

3 months ago

ShemaleZ

lesbian, shemale, stockings, asian, first time
10:40 67%

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

11 months ago

ShemaleTaxi

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10:39 75%

Trans bunnygirl tries vibrations for the very first time

12 months ago

ShemaleMovie

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13:10

Very First Time Using Our Hookup Wag! Tgirl on Lady Girl-Girl Duo

3 years ago

TrannyGem

lesbian, couple, first time
05:08 83%

NUBILE GUY GOT RAGING WITH ME DEEP-THROATING HIS TROUSER SNAKE AND ASK ME TO LET HIM PULVERIZE ME

3 months ago

TrannyGem

amateur, teen (18+), creampie, couple, teen anal (18+), 18, babe
10:13 64%

Real Transgender Gal Gets Ass-Fuck Smash

2 years ago

TrannyGem

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05:37

Young Thai Tranny Enjoys Her First Time Anal Sex On Camera

1 year ago

BeMyHole

thai, asian, ladyboy, domination, first time, bareback
12:32 71%

Blair Glass first Time With a pulverize Machine

2 years ago

ShemaleMovie

glasses, machine, first time
12:40 40%

First Time Using Our Sex Swing! Tgirl On Girl Lesbian Couple

4 years ago

ShemaleZ

BDSM, first time, couple
02:08

GROOBYDVD: Femout First Time Fuckers #2

4 years ago

xHamster

JOI, first time
16:00

Guy having his first time with Geneva and Gina Ryder

6 years ago

ShemaleZ

vintage, first time
06:02

Filipino femboy has first time anal sex on camera

8 years ago

Upornia

filipina, bareback, first time, femboy
04:53

Videoclip music by PinkKissy

1 week ago

TrannyGem

shemale, sissy, heels
11:11 86%

Meaty fake penis destroys my little cootchie

10 months ago

ShemaleTaxi

feet, beauty, dildo, uniform, girlfriend, babe, penis
08:11

His first time sex with a Tgirl is perfect!

12 years ago

AShemaleTube

first time
07:01 54%

Tranny cop first time Sex With a Sneaky Stripper

2 years ago

TrannyOne

amateur, teen (18+), strip, first time
12:46

His Very First Time Pleasing A Trans Dame!

1 month ago

TrannyGem

anal, shemale, bareback, kissing
05:08

Sissy Takes fuck-sticks in Both Holes for the First Time and slurps jism off the Floor

3 months ago

ShemaleMovie

feet, orgasm, dildo, double anal, cumshot, deepthroat, toys
08:07 80%

Car Toon And 3d Animated - Shemale Stepsister Persuaded Stepbrother For Anal Sex For A Long Time, And The Guy Agreed To Take Her Small Dick. Then The Guy Liked It When He Was Fucked In The Ass For The First Time Futa On Male. 8 Min

10 months ago

ShemaleZ

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03:53

Inserting a huge 95mm red dildo for the first time

1 year ago

JizzBunker

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02:58

Sissy sounding pathetic clitty for the first time

2 years ago

xHamster

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34:39 59%

Trans plowing 2 gals for the first time ~KimberlyGeorge~

3 years ago

VideoSection

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06:02

Filipino femboy has very first time without a condom rectal romp on camera

3 years ago

TrannyGem

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05:05

Sofa Sex Domino Presley Fucked For The Very First Time

3 years ago

BeMyHole

couple, chubby, piercing, first time
07:01 14%

Teen girl tricked guy into sex first time Border-hopping Latina bitch

3 years ago

TrannyOne

first time
06:00

Amateur Porn Ladyboy First Time On Cam Bareback Butt Sex

4 years ago

ShemaleZ

first time
07:53

Riding Dildo Tgirl India Taina Shoots A Generous Cumshot During First Time Machine Sex

4 years ago

BeMyHole

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22:32 86%

First time BBC FTM Transman Ethan Hawk

4 years ago

xHamster

couple, BBC, first time, FTM
08:10

Porn emo trannies and queer sex airline first time Elder Sorencronys

5 years ago

ShemaleTaxi

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