SHEMALE • FIRST TIME 3,254 videos

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22:54

First Time Threeway with a Black Tranny Babe

14 years ago

AShemaleTube

black, babe, first time
05:29

Amateur Ladyboy Quin First Time Here

10 months ago

ShemaleZ

first time
10:57

Are you excited about your first time with a tranny

8 years ago

xHamster

first time
09:39 82%

My first-ever time with a trans. Part trio. I shag her rich donk

9 months ago

KeekAss

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17:46

I pulverize a she-creature woman for the first-ever time 4k

2 years ago

TrannyGem

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09:18

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2 years ago

ShemaleTaxi

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22:00

Ts In Stockings Ingrid Moreira The First Time

2 years ago

BeMyHole

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18:34

Hung Trans Keira Verga fucks her fan for the first time

2 years ago

PornHub

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05:29

Elegant transsexual gets fucked by a guy for the first time

10 years ago

AShemaleTube

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59:03

Hard times at Sequoia State Park p.1 - First day

1 year ago

XXXDan

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06:00

Alex gets banged by Tgirl for the first time

4 years ago

ShemaleZ

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06:33

T-Girl for very first Time Fuck-Fest - KimCock

3 years ago

TrannyGem

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06:01

First Time Tranny Guest Anally Fucked In The House

3 years ago

BeMyHole

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06:15

Beauty Spencer Bradley Fucks For Her First Time With A Trans And Its

1 year ago

GetTranny

first time
04:48

Bunny Porks Her Bootie For Dominatrix Molly

1 year ago

TrannyGem

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04:04 73%

Anal Fisting First Time

2 years ago

ShemaleZ

teen (18+), teen anal (18+), fisting, first time
04:50 85%

Inexperienced Teen Fuck My Ass For The First Time, Did He Cum Quickly?

9 months ago

BeMyHole

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10:28

Boy very first time with trans

3 years ago

HDSex

first time
06:23

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5 years ago

AShemaleTube

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14:28

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8 months ago

xHamster

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04:43

Sissy feels a vibration inside her for the first time

2 years ago

xHamster

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11:07 60%

First Time Teacher of Magic and Alice Blitz ( part 2 )

4 years ago

HClips

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01:47

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2 years ago

xHamster

german, 18, first time
09:11 90%

Adorable eighteen Yr Elderly Teenie TGirl With Giant Bootie Entices Stud Into Fuckin Her

6 months ago

TrannyGem

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19:39

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6 years ago

ShemaleZ

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06:25

Holy hell, what a super-hot three-way with mummy Dee Williams. This is the first time that Ellas met Dr. Williams and they are understandably a bit nervous. Dr. Williams do everything she can to put Ella at ease

2 years ago

ShemaleMovie

teen (18+), threesome, teen anal (18+), first time
06:01

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2 years ago

TrannyOne

casting, teen (18+), czech, first time
07:45 50%

Caught masturbating public shower first time Habitual Theft

1 year ago

IcePorn

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03:00

First Time Straight Mexican Pounds Blonde Sissy

1 month ago

AShemaleTube

homemade, creampie, crossdresser, mexican, first time
06:15

We had a first time 3some with a TS female

1 year ago

TrannyOne

first time
03:33

MonikaMonika First time anal play

1 year ago

xHamster

mature, mature anal, polish, first time
12:20

You will never leave behind your first-ever time with shemale Mel

6 years ago

HDSex

bisexual, anal, first time
05:56

Transsexual Fatty Blows Dick First Time 6 Min

6 months ago

ShemaleZ

first time
11:36

Cute TRANNY first time SISSYGASM after make up and stroking

2 years ago

xHamster

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05:50

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4 years ago

TXXX

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08:06

T-Model gives her faux-cock a suck off for the very first time

2 years ago

KeekAss

first time
05:38

Young man gets anal fucked for the first time by the mature TS woman

3 years ago

BeMyHole

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06:06

My first time with a trans. Part 1 While my friend rests

9 months ago

xHamster

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09:43

Beautiful Tbabe Seduces Hot Stud To Fuck Her Ass

3 months ago

BeMyHole

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05:54

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4 years ago

ShemaleZ

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07:55

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8 years ago

PornHub

BBW, first time
12:00

Sissy FIRST TIME ANAL fingering and cumshot on black socks

2 years ago

xHamster

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15:58

This is our first time fucking a tranny

2 years ago

xHamster

JOI, first time
05:56

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5 years ago

IcePorn

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15:56

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

7 months ago

KeekAss

first time
06:38

Z Fucks My Ass with a Strapon (his first time!)

5 years ago

HClips

strapon, first time
28:17

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

8 months ago

xHamster

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05:11

VRB TRANS first-ever Time TS Call doll experience

3 years ago

ShemaleMovie

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08:05

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5 years ago

AShemaleTube

first time
11:49

I was romped by a trans nymph for the first-ever time

2 years ago

KeekAss

homemade, first time
23:20

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11 months ago

ShemaleTaxi

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35:43

Adorable She-Creature first-ever Time Audition Call with Dark-Hued Dom

4 years ago

TrannyGem

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16:38

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6 years ago

AShemaleTube

first time
06:07

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1 year ago

TrannyOne

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09:20

My First Time With A Trans. Part 3. He Moves Deliciously On Top Of My Cock

4 months ago

ShemaleZ

first time
16:34

First time

4 years ago

ShemaleZ

first time
08:00

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2 years ago

IcePorn

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07:57

First-Time Fantasy.

2 years ago

TrannyOne

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06:01

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2 years ago

TrannyOne

first time
04:51

A guy dressed up as a woman for the first time and fucks with a strap-on

3 months ago

JizzBunker

strapon, MILF, bondage, dress, first time
05:46

Newbie Hot Shemale First Time On Webcam Bb Anus

10 months ago

ShemaleZ

first time
08:36

NextDoorStudios - Elliot Finns very first Time with Trans-Dude Luke Hudson

3 years ago

KeekAss

ass licking, first time
13:00

Trans Verbal Demands -Elegant Look With Glove And Sweet Dress

1 year ago

xHamster

cute, gloves, dress, first time
36:47

Kendall Cent - Submits For The First-Ever Time

3 years ago

TrannyGem

first time
06:33

Ladyboy for first time sex - KimCock

5 years ago

ShemaleZ

first time
06:16

First time swinging with a trans, what a blast

1 year ago

TXXX

ass to mouth, first time
08:00

Big ass latin slut first time Stepmom To The Rescue

5 years ago

NuVid

stepmom, slut, first time
07:00

Gloryhole cums in my mouth for the first time

3 months ago

XXXDan

gloryhole, cum in mouth, first time
09:28

Teen Thug first time with Tranny

5 years ago

ShemaleZ

first time
16:42 73%

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

10 months ago

BeMyHole

amateur, stockings, dildo, solo, tentacle, first time
06:25

She-male Jusmin very first Time without a condom

4 years ago

ShemaleMovie

first time
06:45

SEXY ASIAN transsexual casting FOR THE very first TIME

9 months ago

ShemaleTaxi

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08:01

Teen ts threesome and brutal dildo hd first time I ve looked up to

2 years ago

TrannyOne

first time
11:50

Torn Up for my ts gf for the very first time

6 months ago

KeekAss

lesbian, first time
08:12

Hot and deep inside my ass!!!

6 months ago

xHamster

first time
18:17

First time with a tranny

10 years ago

xHamster

first time
06:53

First-time Fantasy - Sharnell Dupree

2 years ago

ShemaleZ

first time
44:47

Intercourse tourist romps a transgender princess for the first time

8 months ago

ShemaleMovie

first time
06:25

Transsexual fatty blows dick first time

7 months ago

IcePorn

first time
10:05

Chloe Temple gets fucked in both ass and pussy on first day at work with doll Winter XX - Trans Angels

4 months ago

XXXDan

big tits, big cock, first time
09:49

Prepare for your first-ever time with a real t-girl

4 years ago

ShemaleMovie

bisexual, first time
12:53

I am sexually aroused about my very first time with a she-creature

5 years ago

HDSex

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05:25

Natalie Mars - Sexy Tranny Milf Fucks A Transgender Man For The First Time

1 year ago

ShemaleZ

first time
05:14 97%

First-ever time going knuckle deep in taut milky culo of nubile she-male

3 years ago

KeekAss

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08:00

Teen girl seducing older man first time Stepmom To The Rescu

5 years ago

IcePorn

stepmom, seduced, first time
04:26

First time for chubby crossdresser

2 years ago

TrannyOne

first time
27:26

First time being role-toyed restrain bondage and conditioning, kneeling and eating cock

1 year ago

ShemaleTaxi

bondage, first time
08:01

College dorm sex party first time Intimate Family Affairs

2 years ago

TrannyOne

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08:00

Mother catches pal cronys daughter masturbating first time

5 years ago

IcePorn

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12:05

Jewelz Blu In Cis And Trans Mermaids Explore New Bodies In First Time Fuck And Kasei Kei

1 year ago

ShemaleZ

first time
04:52

Shaved Cock And Ass The Date - His First Time Discovering His GirlFriend Has A HUGE COCK

2 years ago

BeMyHole

girlfriend, shaving, first time
05:51 64%

POV Asian First Time Anal

4 years ago

ShemaleZ

asian, first time
08:00

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

7 months ago

GetTranny

uncle, first time
06:24

She-creature Jusmin first Time act

9 months ago

ShemaleTaxi

first time
07:59

First Time Trans Girl Fucks Her Tight Virgin Ass 14 Min

10 months ago

GetTranny

first time
08:03

Tgirl Emily Throne Gets Her Ass Drilled

2 years ago

AnyPorn

russian, natural, heels, shaving, first time
13:19

Cd Tries Fucking Dildo For The First Time

8 months ago

ShemaleZ

first time
27:40

Spectacular latin redhead gets her first bisexual tranny penetrate

6 months ago

ShemaleTaxi

bisexual, brazil, first time
12:36

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

3 years ago

xHamster

kissing, strapon, lesbian, BBW, girlfriend, screaming, pegging
33:17

Graziella Blond - His First Time With A Shemale

11 months ago

ShemaleZ

first time
06:46

Sissys training pays off. very first time knuckle in her backside.

1 year ago

ShemaleTaxi

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11:46

Instagram follower drills a trans lady for the first-ever time

3 years ago

TrannyGem

first time
22:37

TRANNY SHEMALE FUCKS STRAIGHT GUY - FIRST TIME TRANSSEXUAL FUCKING

1 year ago

xHamster

latina, first time
03:42

Crossdresser Daisy's first time out in the open .

8 months ago

xHamster

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12:05

TRANSFIXED - Horny Michael DelRay Has His First Trans Experience With Gorgeous Friend Jade Venus

10 months ago

xHamster

first time
06:15

Small tits shemale Jade Downing analed

1 year ago

TrannyGem

handjob, ass licking, small tits, first time
07:31

TSPlayground Busty Ladyboy first Bareback on Camera!

5 years ago

TrannyGem

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14:00

Hetero stud lets Tranny and her boyfriend suck his manstick

1 year ago

ShemaleTaxi

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02:57

Felicia-CD first-ever time on xhamster

2 years ago

KeekAss

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25:54

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4 years ago

ShemaleZ

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06:06

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4 years ago

TrannyGem

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20:06

Handsome bloke spreads his legs to get his tight ass smashed hard by the blonde shemale beauty

3 years ago

BeMyHole

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07:43

First time in drag

1 year ago

TrannyOne

first time
17:21 83%

I Fuck A Tranny Girl For The First Time 4k

1 year ago

ShemaleZ

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06:40

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4 years ago

xHamster

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20:04 92%

TGIRL POST-OP: Jenny Loves Her New Pussy Fucked

2 years ago

xHamster

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35:43

Ultra-Cute Transgender Princess first-ever Time Audition Call with Ebony Dom

4 years ago

KeekAss

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06:10

TBabe Nonny first time anal with big cock plus cumshot

5 years ago

AShemaleTube

first time
14:19

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4 years ago

ShemaleMovie

first time
12:37

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8 years ago

xHamster

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