TRANNY • FIRST TIME 1,058 videos

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10:12 82%

My Teen 18+ Stepsister Wants To Try A Cock For The First Time 10 Min - Amanda Riley And Steve Rickz

3 months ago

ShemaleZ

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14:22 79%

Sophie & Quinns First Time

3 years ago

Upornia

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18:51 82%

Fucked by a man for the first time.

4 years ago

ShemaleZ

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08:06 71%

It Was His First Time With A Trans Woman At First He Was A Little Nervous But He Started To Loosen Up

1 year ago

TXXX

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06:41 71%

Why Straight Guys date Trans Girls

4 years ago

xHamster

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20:01 92%

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4 years ago

ShemaleZ

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03:23 83%

First Time Fucked by a Shemale

5 years ago

ShemaleZ

18, first time
05:29 52%

Sissy Trainer Rus - Virgin Shemale. First Time Sex Lesson

5 years ago

xHamster

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08:23 53%

Straight Guy Fucked By Trans Woman For First Time

2 years ago

ShemaleZ

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08:19 75%

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

1 year ago

xHamster

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32:17 82%

Helena Price - First Time With A Ladyboy Hd

3 years ago

ShemaleZ

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2:25:10 64%

First Time Fembois 2

2 years ago

ShemaleZ

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06:05 75%

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

2 years ago

ShemaleZ

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12:07 55%

You will never forget your first time with shemale babe Mel

8 years ago

xHamster

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11:52 53%

Your first time with a tranny will be amazing

9 years ago

xHamster

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10:00 73%

Boy first time with tranny

13 years ago

xHamster

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19:43

MidLife Crisis (v0.30) - Hetero man having first time anal with a trap (3)

2 years ago

xHamster

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06:00

I Have Been Fucked In The Ass For The First Time By A Ladyboy - HornyShemales

1 year ago

TXXX

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12:06 72%

My First Time With A Trans

10 months ago

HClips

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08:18 45%

Straight dude gets drunk and curious for first time Pt3 cumshaw

6 years ago

ShemaleZ

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18:23 74%

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

1 year ago

xHamster

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01:28 86%

Casting Guy First Time - Itzelxxx

1 year ago

TXXX

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16:30 67%

Teen shemale LOVES first time with boyfriend

9 years ago

TXXX

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12:29 86%

Shy Latino First Time With A Shemale

5 years ago

TXXX

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35:58 88%

Fresh faced dickgirl masturbates for the first time on cam

8 years ago

TXXX

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16:00 86%

Femdom Ts Initiation: First Time Fuckers

4 years ago

ShemaleZ

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28:10 80%

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

1 year ago

ShemaleZ

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23:10 85%

Fucked For The First Time with Domino Presley

4 years ago

ShemaleZ

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04:38

Dude had first time anal with shemale

5 years ago

ShemaleZ

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09:30 77%

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

10 months ago

Upornia

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05:17 56%

Cd and Str8 First time

6 years ago

TXXX

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14:34 79%

Hot young Tgirls first time on fuck machine before I cum all over her face!

5 years ago

TXXX

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08:58 59%

First Time swallowing cum

6 years ago

xHamster

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03:01 84%

FEMOUT XXX: Lemmi's First Time!

3 years ago

xHamster

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05:27 58%

First Time with Milk

4 months ago

xHamster

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37:05

Young Guy fuck the first Time a Shemale

1 year ago

xHamster

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01:52 77%

Anal Training. First Time Using Big Dildo. I Give Up, That's Hurt

2 years ago

xHamster

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36:39 70%

Comes To Visit For The First Time Surprisingly Is A

1 year ago

ShemaleZ

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07:36 67%

Kathy Young Sexy Shemale First Time With Her Stepdaddy Playing 69 In Bed

1 month ago

HClips

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02:55 63%

The first time I take a dick in my ass

5 years ago

xHamster

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07:40 67%

Twink Got Nervous Sucking Tranny S Dick For The First Time - Teaser 8 Min

3 years ago

TXXX

first time
02:25

I was confused the first time I saw this.

10 years ago

xHamster

18, first time
14:06

Your first time with a tranny will be amazing

6 years ago

xHamster

first time
08:12

We Met for The First Time with This Married Handsome Man and We Both Went Beyond Borders

1 year ago

xHamster

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51:27 65%

Little ones first time - all 3 angles

5 years ago

TXXX

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08:04

His first time try it so I did what I did best in DC

5 years ago

TXXX

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04:41

Young Tgirl Aspen in first time anal sex

5 years ago

ShemaleZ

first time
24:09 83%

Phat Rabbit Killer My First Time

4 years ago

HClips

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03:48

Blonde gurls first time.

5 years ago

ShemaleZ

teen (18+), couple, blonde, first time
1:58:01

Hiiragi Kana In Dass-588 When I Met My Childhood Friend For The First Time In Three Years, I Found Out She Had Become A Stunningly Beautiful Young Woman And We Ended Up Having A Physical Relationship. Kana Hiiragi

3 months ago

ShemaleZ

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13:02 88%

Kendal Penny has anal fun in college

4 years ago

xHamster

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05:13 71%

Lena And A Married Males First Time

2 years ago

TXXX

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05:31 54%

Cute TS in sexy lingerie first time fucked by BBC monster

5 years ago

ShemaleZ

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16:16 43%

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5 years ago

xHamster

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14:14

Teen Crossdresser first time anal

6 years ago

ShemaleZ

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03:12 80%

Crossdresser Fucks Uncle for First Time

6 years ago

ShemaleZ

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03:01

His First Time with a Tgirl - Tyra Scott

11 years ago

xHamster

first time
12:18 58%

Shemale and her boyfriend first time on cam

7 years ago

ShemaleZ

first time, boyfriend
25:06

Hellos First Time With fantastic lady-twink

5 years ago

ShemaleZ

first time
07:05

My first time with a trans. Part 2

1 year ago

xHamster

amateur, homemade, teen (18+), first time
11:56 43%

First Time With TS

7 years ago

ShemaleZ

vintage, first time
03:41 70%

Anonymous Random Grindr Fuck - First Time With Trans

2 years ago

ShemaleZ

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11:30 80%

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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04:38

Dudes first time anal sex with shemale

5 years ago

ShemaleZ

first time
05:55

Shemale Creampies Guy for the first Time

6 years ago

ShemaleZ

first time
04:00 60%

Whats Russian for Suck my Cock First Time Girl Fucked By TS Teacher

10 years ago

TXXX

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02:28 53%

Sissy Lexie Adams Crossdresser First Time with Sex Machine

2 years ago

xHamster

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15:21

Boy gets to fuck a CD for the first time

7 years ago

xHamster

couple, lingerie, first time
05:49

The First Time He Fucks With A Trans 6 Min

3 years ago

Upornia

first time
05:09

Tight Ass Tgirl Gets Fucked For The First Time

6 years ago

ShemaleZ

tight, first time
15:34 87%

ASIANTGIRL - Compilation Updates 27th Jan to 31st Jan '25

4 months ago

xHamster

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19:36

Pretty young tgirl ass fucked by girl for the first time

4 years ago

TXXX

POV, first time, shemale and girl
03:01

Lemmis First Time!

2 years ago

HClips

first time
12:20 78%

Sissy Training After First Time Feminization

1 year ago

xHamster

BDSM, first time, sissy
03:10

First time CD

7 years ago

ShemaleZ

first time
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

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15:30 78%

I arrived by surprise. It was his first time sucking a shemale

2 years ago

xHamster

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14:58 87%

My first time with a trans girl !!

7 months ago

xHamster

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05:32 57%

First time

5 years ago

xHamster

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04:09

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5 years ago

ShemaleZ

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05:56

Amateur Tgirl First Time On Cam

6 years ago

ShemaleZ

first time
05:12

Zmsfm & Lm19 Hard anal sex hot tasty slut swallowing huge cock in her tight ass tasty anus gaped for the first time hot ass

1 year ago

xHamster

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2:40:58 69%

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

2 months ago

ShemaleZ

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08:47

Amateur First Time Group Sex

6 years ago

ShemaleZ

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09:56 60%

Boy first time with tranny

5 years ago

ShemaleZ

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06:00

Amateur T-Girl First Time On Cam

11 years ago

xHamster

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06:00

Amateur Porn Ladyboy First Time On Cam Bareback Butt Sex

3 years ago

ShemaleZ

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08:08 54%

My very first time

7 years ago

xHamster

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04:38

Dude for the first time gets shemales dick

6 years ago

TXXX

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29:07

Teaching str8 young boy first time ladyboy experience

7 years ago

ShemaleZ

ladyboy, first time
04:05

Young sissyslut getting pounded for first time by complete stranger

5 years ago

ShemaleZ

stranger, first time
05:31

Shy Sissy First Time To Suck

3 years ago

HClips

shy, first time
10:11 93%

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

1 year ago

ShemaleZ

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06:15 79%

Marilyn Johnson And Claire Tenebrarum In Marilyn First Time To Blow Shemale Cock

2 years ago

ShemaleZ

first time
35:17

The First Time Married To A Trans Girl

3 weeks ago

HClips

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15:37

First Time Eating Ass

2 years ago

Upornia

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04:59

First time with my transvestite friend

1 year ago

xHamster

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08:08

My first time to try 15 inch King Cock with high speed fucking machine

10 months ago

xHamster

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03:40 73%

Your Very First Time - Trans Femdom GFE with Melissa Masters

3 years ago

xHamster

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05:01

VRB TRANS First Time TS Call Girl Experience

5 years ago

xHamster

first time
07:05

My First Time With A Trans. Part 2

1 year ago

ShemaleZ

teen (18+), 18, first time
05:11

RUBBERDOLL MONIQUE - As a bimbo doll at a parking lot

2 years ago

xHamster

latex, doll, first time
04:58

Submissive Girl Tied Sg Gets Pet Played And Fucked In The Ass First Time Pt1 5 Min

1 year ago

ShemaleZ

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39:29

Sharnell Dupree - First-time Fantasy

4 years ago

TXXX

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44:37

Sex Tourist Bangs A Shemale For The First Time

3 years ago

HClips

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10:46

Transexual Brandy Alexander gets fucked and facialized for the first time

6 years ago

ShemaleZ

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10:10

Stepbro Analed Ts Stepsis For First Time

2 years ago

ShemaleZ

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05:07

Dudes First Time Ass Fuck Making Out With Shemale With Sergeant Miles, Coco De Mal And Kylie Maria

1 year ago

ShemaleZ

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10:38

The First Time You Never Forget

4 years ago

Upornia

teen (18+), first time
18:28

Its time you tasted your first shemale cock

6 years ago

xHamster

first time
16:51 64%

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

1 month ago

HClips

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18:53 88%

Made His First Time Memorable - Anastasia Penny

1 year ago

ShemaleZ

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04:37

Very Cute Couple First Time Anal

5 years ago

xHamster

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03:38

His First Time Getting Fucked by a Shemale

6 years ago

ShemaleZ

first time
17:15

Skinny Ladyboy Fucks A Guy For The First Time. P1 18 Min

3 years ago

ShemaleZ

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13:00 83%

Nur mit Gummi in den Arsch bitte

3 years ago

xHamster

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12:40 40%

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

4 years ago

ShemaleZ

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05:57

My first time with a black tgirl

6 years ago

ShemaleZ

first time
05:52

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5 years ago

ShemaleZ

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29:19

The first Time Kisses Came Upon Rio

5 years ago

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