SHEMALE • FIRST TIME 2,509 videos

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08:23 67%

Straight Guy Fucked By Trans Woman For First Time

8 months ago

ShemaleZ

amateur, big cock, webcam, first time
05:58

Males First Time With Transgender

2 years ago

BeMyHole

prostitute, first time
06:15

Jamie Kelly fucks for the first time with another trans woman

4 months ago

XXXDan

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08:03 86%

Cutiepii33quinn first-ever time...

1 year ago

ShemaleMovie

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29:46 58%

Teaching str8 young boy first time she-male experience on webcam

3 years ago

HDSex

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12:37

Johnny;s first Time wt A Hawt Trans Honey

7 months ago

TrannyOne

18, big cock, first time
01:52 59%

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

9 months ago

xHamster

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16:44

My First Time With A Tranny

3 weeks ago

BeMyHole

amateur, shemale, creampie, anal, shemale and girl
19:43

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

8 months ago

xHamster

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10:00 92%

Boy first time with tranny

11 years ago

xHamster

first time
2:25:10

First Time Fembois 2

7 months ago

ShemaleZ

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23:47 73%

Guys first Time with Tgirl

1 year ago

TrannyOne

69, first time
20:16

First Time Anal with Tundra

7 months ago

TrannyOne

amateur, shemale, anal, first time
32:50

Gorgeous Darkhair Nasty Shemale Interracial Sex

3 years ago

Analdin

shemale, blowjob, anal, big ass, interracial
06:15

First time with a Shemale Escort

1 year ago

TrannyOne

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05:42

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3 years ago

ShemaleMovie

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21:05

Super hot transgender princess screws for first time her boyfriend

2 years ago

ShemaleTaxi

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07:16

First-ever time with a she-creature, I called Renata Fontes to give and fellate very hard

2 years ago

ShemaleTaxi

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07:06

Getting dominated and deepthroating cock for the first-ever time like a little bi-atch with facial ��

10 months ago

ShemaleTaxi

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17:35

Young dude screwed in the ass for the first time by a tranny

2 years ago

ShemaleMovie

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14:19

Is this really your first time with a t-girl

2 years ago

ShemaleMovie

first time
08:20

Youngster got jumpy deep throating tranny s dick for the first time - teaser

1 year ago

ShemaleMovie

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05:30

My wife pummeled me in the butt for the first-ever time, but I even liked it

7 months ago

ShemaleTaxi

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06:19

There is a very first time for everything

2 years ago

ShemaleTaxi

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08:07

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1 year ago

ShemaleTaxi

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10:46

Transexual Brandy Alexander gets fucked and facialized for the first time

4 years ago

ShemaleZ

amateur, facial, first time
10:09

(Re-upload) bigcock transgender very first time with 11inches meaty bone

4 months ago

KeekAss

handjob, amateur, blowjob, anal, cumshot
02:28

Sissy Lexie Adams Crossdresser First Time with Sex Machine

5 months ago

xHamster

amateur, stockings, anal, dildo, lingerie
06:56

Irresistible SheBabe to be fuck for first time Part2

1 year ago

DrTuber

first time
05:00

Ts gets blowjob first time Sneaking Around With Daddys partner

1 year ago

TrannyOne

first time
06:32

First time with a Shemale MILF

3 years ago

TrannyOne

first time
09:37

Straight guy gets his ass pounded hard by the shemale for the first time

1 year ago

TrannyOne

latex, first time
10:51

My STEPSISTER asks me to do ass-fuck for the first-ever TIME

1 month ago

ShemaleTaxi

first time
07:01

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

1 year ago

TrannyOne

latina, first time
25:12

Cool tranny and lovely tutor Real guy first-ever time (นางใน)

1 year ago

TrannyGem

redhead, shemale fucks guy, first time
06:15

Heterosexual boy have joy boning transexual for the first-ever time (Crystal Thayer, Large Titties, Yam-Sized Orbs)

6 months ago

KeekAss

blowjob, anal, lingerie, tattoo, 18
06:55

My ass tastes sweet - i get all my 3 holes fucked for the very first time film

6 months ago

TrannyOne

amateur, anal, first time
13:25

First time teacher of magic and alice blitz ( part 1 )

9 months ago

TrannyOne

teacher, cum in mouth, first time
20:47

First time sucking and fucking

1 year ago

TrannyOne

crossdresser, first time
03:23

First Time Fucked by a Shemale

3 years ago

ShemaleZ

18, first time
1:40:20

My First Time With A Tranny (Full Hd Version – Director’s Cut)

7 months ago

TrannyOne

shemale, first time
16:43

Feels Like The First Time . . .

2 years ago

xHamster

shemale, first time
05:23

Cute Sexy Beginner CD Shemale Lover.

9 months ago

xHamster

handjob, cute, shemale, anal, big ass
16:30

Teen shemale LOVES first time with boyfriend

7 years ago

TXXX

small tits, boyfriend, first time
05:44

First time experience with transsexual Latina Isabella Fontana

2 months ago

AnySex

amateur, anal, big ass, big tits, latina
12:29

Shy Latino First Time With A Shemale

3 years ago

TXXX

amateur, shy, first time
03:41

Anonymous Random Grindr Fuck - First Time With Trans

1 week ago

ShemaleZ

amateur, stockings, creampie, bareback
22:22

Femoutfuckers for the first time

3 months ago

XXXDan

ebony, amateur, black, shemale, blowjob
05:09

Dude had first time anal with shemale

1 year ago

TrannyOne

crossdresser, first time
16:43

Feels Like The First Time

1 year ago

ShemaleZ

bareback, small tits, first time
08:46

Cute Tgirls Enjoy Anal Sex with each other

4 years ago

TrannyGem

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07:49

Fucked for the Very First Time

2 years ago

AShemaleTube

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19:36

Pretty young tgirl ass fucked by girl for the first time

2 years ago

TXXX

stockings, shemale, POV, shemale and girl, ass
13:25

His very first time with a ladyboy

5 years ago

HDSex

nylon, skinny, hardcore, first time
05:45

My First Time with a Transsexual

5 years ago

ShemaleZ

first time
05:56

Amateur Tgirl First Time On Cam

4 years ago

ShemaleZ

first time
23:19

First Time For My Husband Fuck With Ladyboy

2 months ago

Upornia

amateur, teen (18+), shemale, asian, ladyboy
04:52

Shaved Cock And Ass The Date - His First Time Discovering His GirlFriend Has A HUGE COCK, Part 2

1 year ago

TrannyOne

ebony, black, girlfriend, shaving, first time
05:06

Kristis First Time Fucking A Dildo While Jerking Off Her Big Hard Cock

3 weeks ago

ShemaleZ

first time
08:10

Rough tranny first-ever time mind-blowing y., Alexa Nova and Kendall

2 years ago

ShemaleTaxi

bondage, BDSM, hardcore, first time
05:39

Melissa s first time at the theater

1 year ago

AShemaleTube

crossdresser, first time
12:40

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

2 years ago

ShemaleZ

lesbian, couple, BDSM, first time
16:16

This is my first time fucking a shemale babe

3 years ago

xHamster

blowjob, anal, ladyboy, shemale and girl, big cock
05:41

Redhead TS TS Aspen Brooks first time fucking Mercedes Carrera tight pussy

5 years ago

ShemaleZ

tight, first time
03:01

FEMOUT: Ms. Momo's First Time

11 months ago

xHamster

beauty, stockings, small cock, shemale, big ass
03:05

TGirls Porn: Luna Breaks In Dani

7 months ago

xHamster

blowjob, anal, couple, webcam, small tits
05:30

My First Time With Beautyfull Shemale 6 Min

6 months ago

ShemaleZ

big ass, blonde, ass, first time
12:18

Shemale and her boyfriend first time on cam

5 years ago

ShemaleZ

boyfriend, first time
08:17

His First Time And A Transsexual Xhunpgy

3 months ago

Upornia

shemale, vintage, first time
08:01

Mom dad family first time He didnt want to do anything except work, wh

1 year ago

TrannyOne

mom, first time
07:39

Flustered By Disappointed Client She Offers Sex

3 weeks ago

BeMyHole

first time
05:32

First time

3 years ago

xHamster

mature, amateur, shemale, mature anal, anal
10:38

The First Time You Never Forget

2 years ago

Upornia

teen (18+), lingerie, ladyboy, big cock, bareback
11:00

First-ever time buttfuck fisted

4 years ago

HDSex

fisting, prostitute, gape, first time
13:51

Ts Was Fucked By Xxl Cock For The First Time 14 Min - Inked Girl

3 months ago

ShemaleZ

amateur, shemale, POV, tattoo, shemale and girl
18:06

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

1 year ago

HomemadeXXX

amateur, homemade, blowjob, creampie, anal
05:55

Shemale Creampies Guy for the first Time

4 years ago

ShemaleZ

shemale, creampie, first time
06:25

First time shemale, shemale ass, blow-job

2 years ago

HDSex

bareback, first time
05:31

Cute TS in sexy lingerie first time fucked by BBC monster

3 years ago

ShemaleZ

cute, small cock, shemale, blowjob, interracial
32:23

JoJo Havana First-Ever Time non-pro Comes In Porno With A group sex

2 years ago

TrannyGem

group, first time
02:01

Sissy first time anal

1 year ago

xHamster

amateur, dildo, lingerie, ladyboy, solo
05:08

Dude for the first time gets shemales male stick

4 years ago

Analdin

shemale, swinger, party, fetish, ladyboy
38:26

OMG – only after she pulled her pants down did he know she had a dick

1 year ago

xHamster

shemale, anal, MILF, orgasm, big tits
1:06:07

Small tits latin gf Valentina anal fucked for the first time

3 years ago

VipTube

anal, first time
17:15

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

1 year ago

ShemaleZ

shemale, ladyboy, 18, skinny, first time
05:42

First-ever time

3 years ago

HDSex

first time
08:05

Aubrey First Time

4 years ago

ShemaleZ

first time
04:37

Very Cute Couple First Time Anal

3 years ago

xHamster

cute, shemale, couple, bareback, small tits
03:10

BOBSTGIRLS: Boom Boom - New Girl Lola Bloom

1 month ago

xHamster

cute, beauty, big ass, big tits, solo
12:20

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

3 years ago

VideoSection

first time
08:02

Dude Fucks His Trans Crush For His First Time- Pierce Paris, TS Foxy

5 months ago

TrannyOne

bareback, first time
08:00

Teen braces facial compilation and licking orgasm first time

3 years ago

IcePorn

orgasm compilation, first time
02:15

His First Time - VenusLux

2 years ago

TXXX

stockings, asian, first time
29:07

Teaching str8 young boy first time ladyboy experience

5 years ago

ShemaleZ

ladyboy, first time
16:38

Your first time with a tranny will be outstanding

3 years ago

ShemaleMovie

ebony, black, bisexual, hardcore, first time
06:15

We had a first time threesome with a tranny woman

1 month ago

TrannyOne

anal, threesome, reality, first time
27:17

Cuties First Time With ladyboy

5 years ago

ShemaleZ

first time
13:25

Crossdressing for the very first time was sexier than I imagined

1 year ago

ShemaleMovie

ebony, black, blowjob, crossdresser, first time
53:13

First Time butthole couple Sex

5 months ago

TrannyOne

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10:03

Pooja's fuckd by. first time shemale

1 month ago

xHamster

amateur, indian, shemale, asian, first time
14:15

You will never forget your first time with t-girl Mel

3 years ago

ShemaleMovie

first time
09:15

Young german amateur transexual teen shemale fucks first time anal with huge cock

6 months ago

TrannyOne

amateur, teen (18+), german, anal, teen anal (18+)
06:07

Stockinged trap sweetheart toys her taut caboose

2 years ago

ShemaleTaxi

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13:38

Rookie lad gets his fat ass banged hard for the first time by the nasty TS chick

1 year ago

TrannyOne

fat, cum in mouth, cum in ass, first time
01:26

Shaggy Fucks a Crossdresser for the First Time

3 weeks ago

xHamster

first time
05:54

Shemale fucks white man for the first time

3 years ago

ShemaleZ

shemale, big ass, 18, ass, first time
10:20

Claudia Clars very first Time Jizm

2 years ago

TrannyGem

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06:28

My first time with a ladyboy

5 years ago

AShemaleTube

teen (18+), shemale and girl, first time
08:04

DESIRE LADYBOY - First-Timer Teenager Tgirl Thaysa Carvalho Gets Her Culo Gaped and Creampied Two Times

1 year ago

TrannyGem

creampie, small tits, gape, first time
07:32

First Time Oral With A Transgendered Jock

1 month ago

TXXX

first time
07:41

German Crossdresser First Time in front of cam

10 years ago

AShemaleTube

amateur, german, first time
05:58

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1 year ago

TrannyOne

mature, chubby, interracial, first time
59:03

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

9 months ago

XXXDan

mature, amateur, blowjob, big ass, outdoor
07:55

DeeDeeSluts First Time Out in Public

2 weeks ago

xHamster

public, crossdresser, first time
05:31

Shy Sissy First Time To Suck

1 year ago

HClips

amateur, stockings, POV, crossdresser, shy
03:33

MonikaMonika First time anal play

8 months ago

xHamster

mature, amateur, stockings, mature anal, anal
12:55

Sissy Anal JOI for Beginners - Femboy Helps you in your Anal first Time

2 years ago

BeMyHole

JOI, sissy, femboy, first time
05:30

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4 years ago

ShemaleZ

thai, first time
06:30

Hottie Lilly First Time Have Intimacy With Tgirl Aubreys

1 year ago

ShemaleZ

outdoor, blonde, first time
11:35

First-Ever Time sextoy man-cream For T-hottie Moxxi Mewws

2 years ago

TrannyGem

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