SHEMALE • FIRST TIME 3,346 videos

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11:21 82%

First time with a

3 years ago

TrannyOne

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14:56 57%

Domme T: first-ever Time rope-On Virgin

8 months ago

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2 years ago

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12:00

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1 year ago

YourLust

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06:00

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5 years ago

BravoTube

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34:12

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5 days ago

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04:30 83%

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3 years ago

TrannyOne

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11 months ago

JizzBunker

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1 year ago

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1 year ago

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05:18 80%

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4 years ago

VideoSection

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5 years ago

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10:36 70%

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1 year ago

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1 year ago

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4 years ago

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14:29 70%

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5 years ago

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06:55

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7 years ago

ShemaleZ

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4 years ago

HDSex

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22:15

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9 months ago

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9 months ago

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31:37 77%

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4 years ago

AShemaleTube

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16:11

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3 years ago

TrannyOne

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21:06 78%

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3 years ago

TrannyOne

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07:42

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1 year ago

GetTranny

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51:27 65%

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4 years ago

TXXX

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09:30 78%

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

3 months ago

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40:52 56%

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3 months ago

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08:09 65%

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3 years ago

TrannyOne

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10:00 75%

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12 years ago

xHamster

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01:28

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1 year ago

TXXX

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05:18

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2 days ago

ShemaleTaxi

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32:17 82%

Helena Price - First Time With A Ladyboy Hd

3 years ago

ShemaleZ

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03:53 71%

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1 month ago

AShemaleTube

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17:35

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3 years ago

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08:15

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4 years ago

VideoSection

first time
06:15 87%

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2 years ago

ShemaleZ

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14:58 86%

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3 weeks ago

xHamster

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13:25

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6 years ago

HDSex

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27:35 76%

Ts Aubrey Kate gives him motivation and the cock for his first time

1 month ago

AShemaleTube

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06:30

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4 months ago

xHamster

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12:08

My First Time With A Trans

1 year ago

BeMyHole

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03:25 47%

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

1 year ago

TrannyGem

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06:20 66%

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4 years ago

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22:08

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3 months ago

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28:10 75%

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

1 year ago

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21:59 80%

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1 year ago

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6 years ago

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4 years ago

AShemaleTube

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03:23

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5 years ago

ShemaleZ

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1 year ago

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1 year ago

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10:01

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10 years ago

MyLust

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06:30

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4 years ago

TrannyGem

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18:23 72%

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6 months ago

xHamster

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18:51 91%

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4 years ago

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07:01

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3 years ago

TrannyOne

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16:00 84%

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4 years ago

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10:43 68%

Girl tries to fuck with trans first time

5 years ago

AShemaleTube

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05:12

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Today

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18:47

The Pill Episode 2 - Chris First Time

1 year ago

JizzBunker

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05:58

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3 years ago

TrannyOne

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05:13

Lena And A Married Males First Time

2 years ago

TXXX

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23:22 80%

Fucked for the First Time

4 years ago

BeMyHole

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08:01 73%

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3 years ago

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06:15

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8 months ago

AShemaleTube

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02:57 78%

Modest tranny lets her new boyfriend fuck her tight hole for the first time.

1 month ago

AnySex

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08:44

Crossdressers First Time

3 years ago

TrannyOne

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09:08 63%

Tatted Guys First Time With a Trans damsel: Blows His geyser and His Mind over a Smoking oral pleasure

3 months ago

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08:01

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3 years ago

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19:38

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3 months ago

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06:01

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3 years ago

TrannyOne

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23:47 65%

Guys first Time with Tgirl

3 years ago

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05:01 91%

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6 years ago

AShemaleTube

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17:30

Young guy gets fucked in the ass for the first time by a trans

7 months ago

JizzBunker

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1 year ago

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2 years ago

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14:09 67%

Venus Lux Fucks First Time Bottom JakeD

1 year ago

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14:51 77%

Sophie & Quinns Very First Time

3 years ago

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08:01

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3 years ago

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21:45

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14 years ago

AShemaleTube

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05:17 56%

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5 years ago

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5 years ago

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06:20

Watch busty tgirl Emma Rose her first time sex with a woman

4 months ago

AShemaleTube

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16:43

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3 years ago

xHamster

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46:35

First Time With A Shemale

4 years ago

BeMyHole

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03:41 61%

Anonymous Random Grindr Fuck - First Time With Trans

1 year ago

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26:35 62%

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1 year ago

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04:26

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7 months ago

TrannyGem

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06:15

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1 year ago

TrannyOne

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17:52

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2 years ago

TrannyOne

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32:59

Helena Price 1st Time Transgender dame

1 year ago

ShemaleTaxi

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09:06

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1 year ago

KeekAss

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3 years ago

xHamster

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02:28 53%

Sissy Lexie Adams Crossdresser First Time with Sex Machine

2 years ago

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3 years ago

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05:49

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2 years ago

Upornia

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18:06

Sexually Attractive TS And Straight Guy Go At It For The First Time! - Shemale

3 years ago

HomemadeXXX

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His First Time with a Tgirl - Tyra Scott

10 years ago

xHamster

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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

6 months ago

HClips

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16:52

My first Time

3 years ago

TrannyOne

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5 years ago

ShemaleZ

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05:32 54%

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5 years ago

xHamster

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4 years ago

VideoSection

first time
15:10

My first time as a sissy was so liberating

2 years ago

ShemaleTaxi

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18:47

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4 years ago

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06:20

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3 years ago

TrannyOne

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1 year ago

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11:33

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3 years ago

AShemaleTube

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Sissy lad gets to fuck the trans babes thick ass for the first time

2 years ago

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13:04 83%

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

1 year ago

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1 year ago

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4 years ago

AShemaleTube

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28:31

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3 years ago

TrannyGem

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6 years ago

xHamster

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Hot lad gets his hairy ass stretched by the stunning TS chick

4 years ago

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5 years ago

AShemaleTube

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