SHEMALE • FIRST TIME 501 videos

Popular Latest Top rated

23:44 65%

First-ever time for my hubby plow with Ladyboy

1 year ago

ShemaleTaxi

handjob, bisexual, anal, orgasm, ladyboy, taxi, first time
31:37

Shy Couple first time shemale experience 2

4 years ago

AShemaleTube

couple, shy, first time
32:50 67%

Gorgeous Darkhair Nasty Shemale Interracial Sex

4 years ago

Analdin

blowjob, anal, big ass, interracial, police, big tits, latina
51:27 58%

Little ones first time - all 3 angles

4 years ago

TXXX

asian, bareback, first time
16:53 79%

Senses Like The first-ever Time . . .

3 years ago

ShemaleTaxi

couple, bareback, first time
16:12 60%

Be gentle this is my first time with a tranny

2 years ago

TrannyOne

first time
32:17 82%

Helena Price - First Time With A Ladyboy Hd

2 years ago

ShemaleZ

shemale, big tits, ladyboy, tattoo, ass licking, first time
20:01 94%

Pretty young tgirl ass fucked by girl for the first time

5 years ago

PornHub

ass, first time, brunette
16:11

Is this your first time fucking a hot tranny

2 years ago

TrannyOne

first time
22:15

Very first time hj given by an exotic dark eyed girl

1 month ago

ShemaleTaxi

handjob, shemale, BDSM, facesitting, jerking, taxi, first time
22:23 71%

Fucked For The Very First Time

2 years ago

TrannyOne

first time
23:10

Fucked For The First Time with Domino Presley

3 years ago

ShemaleZ

first time, shemale fucks guy
17:08

Skylar and Rays First Time Part 1

4 years ago

TXXX

first time
22:15

Very first time hand-job given by an exotic dark spotted girl

6 days ago

ShemaleMovie

shemale and girl, shemale, first time, BDSM
28:10 73%

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

5 months ago

ShemaleZ

amateur, redhead, girlfriend, first time
19:43

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

1 year ago

xHamster

small cock, creampie, 18, small tits, first time
20:01 93%

Pretty young tgirl ass fucked for the first time

3 years ago

ShemaleZ

shemale, lingerie, redhead, first time, cumshot
15:58

Ladyboy fuck a white dude in ass

3 years ago

PornHub

russian, dogging, mask, first time, shemale fucks guy, brunette, cum in ass
25:12 58%

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

2 years ago

TrannyGem

blowjob, redhead, first time, shemale fucks guy
35:58

Fresh faced dickgirl masturbates for the first time on cam

7 years ago

TXXX

solo, masturbation, first time
23:22 80%

Fucked for the First Time

3 years ago

BeMyHole

femdom, latex, dogging, panties, first time, shemale fucks guy
15:57

The first time

7 months ago

AShemaleTube

amateur, POV, first time
16:11

Is this your very first time tearing up a red-hot transgender princess

4 years ago

TrannyGem

first time
21:59 84%

Trans nailing a heterosexual stud for the first-ever time

6 months ago

TrannyGem

homemade, blowjob, latina, first time, shemale fucks guy
19:50

Thai Transgender Princess

2 years ago

TrannyGem

asian, first time
21:06 74%

Hot guy gets his ass plowed for the first time by a nasty shemale beauty

2 years ago

TrannyOne

first time
29:46 56%

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

4 years ago

HDSex

webcam, first time, femboy
1:45:31

Big T In *limited First Time* [innocent Big Breasts Girl] Too Le

5 months ago

Upornia

shemale and girl, first time
18:50

AUBREYS FIRST-EVER TIME

3 years ago

TrannyGem

shemale, first time
37:05

Young Guy fuck the first Time a Shemale

6 months ago

xHamster

first time
18:47

The Pill Episode 2 - Chris First Time

7 months ago

JizzBunker

babe, first time
2:25:10 53%

First Time Fembois 2

1 year ago

ShemaleZ

redhead, first time, shemale fucks guy, brunette
43:28 81%

Shelady Very First Time cam

3 years ago

TrannyGem

blowjob, creampie, first time
16:00 77%

Femdom Ts Initiation: First Time Fuckers

3 years ago

ShemaleZ

femdom, threesome, first time
19:43

MidLife Crisis v0.30 - Straight man gets anal for the first time with a trap 3

3 months ago

JizzBunker

small cock, creampie, anal, college, cartoon, first time
17:35

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

3 years ago

ShemaleMovie

first time, shemale fucks guy
23:47 63%

Guys first Time with Tgirl

2 years ago

TrannyOne

69, first time
34:39 55%

Trans plowing 2 gals for the first time ~KimberlyGeorge~

1 year ago

VideoSection

shemale, threesome, group, first time
16:30

Teen shemale LOVES first time with boyfriend

8 years ago

TXXX

blowjob, first time, boyfriend
18:44

Suspended Trans Keira Verga fucks her aficionado for the first-ever time

2 weeks ago

ShemaleMovie

stockings, first time, anal, shemale, blowjob, heels
18:51

Fucked by a man for the first time.

3 years ago

ShemaleZ

POV, first time
19:01

T-girl Alice first-ever time dominating her beau

3 years ago

VideoSection

thai, couple, BDSM, ladyboy, vibrator, first time
32:13

Sensational DEBUT: The miracle You can Only see Here - First Time Crossdresser Rina : See More→https://bit.ly/EagleGay

1 year ago

ShemaleMovie

asian, japanese, first time
46:35

First Time With A Shemale

2 years ago

TrannyOne

first time
27:53 77%

Anastasia Penny – He Hired An Escort For The First Time

1 year ago

Upornia

big tits, lingerie, first time, escort
17:07

Step-Mom instruct a significant lesson to her fresh step daughter-in-law (How to be a tramp)

3 weeks ago

TrannyGem

mom, cute, shemale, fat, anal, instruction, facesitting
31:51

First-ever time for youthfull hetero Latino to be fucked by transsexual Latina

1 year ago

ShemaleMovie

black, outdoor, domination, first time, shemale fucks guy
16:43

Feels Like The First Time . . .

3 years ago

xHamster

first time
16:44 58%

My First Time With A Tranny

11 months ago

BeMyHole

creampie, squirt, shemale and girl, domination, first time
1:40:20

My first time with a transexual Full Hd Version Directors Cut

3 months ago

JizzBunker

first time
53:13 57%

TScumshot.com first time anal couple sex tgirls

2 years ago

TrannyOne

couple, first time, BDSM
16:06

His very first time with a trans, did he like it2

4 months ago

KeekAss

blowjob, crossdresser, first time
17:52

Lady sextasy experiences transgender intense fucking for the first time also enjoys it

2 years ago

TrannyOne

first time, hardcore
16:16

This is my first time fucking a shemale babe

3 years ago

xHamster

babe, first time
33:17 76%

His very first time with a she-creature

1 year ago

KeekAss

MILF, vintage, domination, first time, shemale fucks guy
16:52

My first Time

2 years ago

TrannyOne

first time
17:57 67%

Legacy dirt: skinny she-male fucks a guy for the first time. P2

1 year ago

ShemaleTaxi

ladyboy, domination, skinny, first time
25:45

FUTANARIA FIRST TIME FUCK BUDDIES

3 years ago

ShemaleZ

first time
21:45

Guy first time with blonde Tgirl

13 years ago

AShemaleTube

first time
46:35

First Time With A Shemale

3 years ago

BeMyHole

first time
44:37

Sex Tourist Bangs A Shemale For The First Time

2 years ago

HClips

threesome, first time, brunette
21:05

Super hot transgender princess screws for first time her boyfriend

3 years ago

ShemaleTaxi

taxi, first time, boyfriend
21:50

Trans Fucking A Straight Boy For The First Time

3 months ago

ShemaleZ

BDSM, first time
17:25

Young guy fucked in the ass for the first time by a tranny

3 years ago

xHamster

mature anal, couple, first time, shemale fucks guy
15:10

My first time as a sissy was so liberating

1 year ago

ShemaleTaxi

crossdresser, taxi, first time
24:09 83%

Phat Rabbit Killer My First Time

3 years ago

HClips

ebony, interracial, tattoo, ass licking, first time
2:55:43

First Time Fembois

1 year ago

Upornia

stockings, first time
28:18

Amazing Roxxie Moth Gets Anal Bareback First Time

3 years ago

BeMyHole

cute, stockings, blowjob, first time, hardcore
18:24 73%

The very first time

7 months ago

AShemaleTube

mature, homemade, stockings, shemale, crossdresser, first time
25:06

Hellos First Time With fantastic lady-twink

4 years ago

ShemaleZ

first time
15:30

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

10 months ago

xHamster

amateur, couple, shemale and girl, compilation, surprise, cumshot compilation, first time
15:37

First Time Eating Ass

1 year ago

Upornia

first time
20:16

First Time Anal with Tundra

1 year ago

TrannyOne

amateur, anal, first time
20:47

First time sucking and fucking

2 years ago

TrannyOne

crossdresser, first time
19:36

Pretty young tgirl ass fucked by girl for the first time

3 years ago

TXXX

POV, first time
15:31

Guy gets to screw a CD for the very first time

4 years ago

ShemaleMovie

first time
32:59

Helena Price 1st Time Transgender dame

4 months ago

ShemaleTaxi

shemale, first time
19:43

MidLife Crisis (v0.30) - Heterosexual dude having first-ever time anal invasion with a trap (three)

1 year ago

KeekAss

small tits, first time
21:31

Naughty man gets his sweet ass banged hard by the huge TS dick for the first time

2 years ago

TrannyOne

feet, heels, first time
18:53

Made His First Time Memorable - Anastasia Penny

4 months ago

ShemaleZ

cumshot, big cock, first time
15:54

SOMEONES SPUNKING

2 years ago

TrannyGem

strip, goth, first time
44:40 61%

Indian Taina - My First Time With An Indian

1 year ago

ShemaleZ

ebony, indian, shemale, interracial, big cock, first time
23:46

Guys first Time with Tgirl

3 years ago

BeMyHole

nipples, 69, panties, jeans, first time
1:06:07

Small tits latin gf Valentina anal fucked for the first time

4 years ago

VipTube

first time
15:28

Brunette gets Pegged by Wife for the first Time

3 years ago

TrannyGem

wife, clit, big clit, erotic, pegging, first time, sensual
39:29

Sharnell Dupree - First-time Fantasy

3 years ago

TXXX

first time
15:21

Boy gets to fuck a CD for the first time

5 years ago

xHamster

couple, lingerie, first time
15:15 77%

VERY FIRST TIME TRANSGENDER PLOWED IN BOOTY AND CREAMPIED

10 months ago

KeekAss

amateur, stockings, creampie, bareback, first time
16:43

Feels Like The First Time

2 years ago

ShemaleZ

first time
22:46 55%

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

2 years ago

TrannyOne

feet, ass to mouth, cum in mouth, sissy, first time, cum in ass
15:57

Yvanas First Time On Porn - Alexandra Bxl

1 year ago

ShemaleZ

stockings, lingerie, first time
18:47

BrFat guy gets his thick ass toyed and stretched by the horny TS babe

3 years ago

BeMyHole

dogging, mask, dress, first time
19:58 65%

MY FIRST TIME FUCK BEAUTIFUL SHEMALE ON UPSTAIRS

1 year ago

xHamster

beauty, small cock, creampie, anal, interracial, bareback, small tits
28:31

Roxxie Cracking In A First-Ever Timer

3 years ago

TrannyGem

first time
16:19

MY VERY FIRST TIME WITH A TRANSVESTI! (JÚLIA DENTTELO)

2 years ago

TrannyGem

brazil, teen anal (18+), first time
29:19

The first Time Kisses Came Upon Rio

4 years ago

TXXX

kissing, first time
23:19

First Time For My Husband Fuck With Ladyboy

1 year ago

Upornia

amateur, teen (18+), asian, husband, first time
29:07

Teaching str8 young boy first time ladyboy experience

6 years ago

ShemaleZ

ladyboy, first time
1:02:42 59%

First Time Visit To The Gloryhole For This attractive playgirl

4 years ago

ShemaleZ

gloryhole, first time
38:29

Moscardiniema - I Remember The First Time I Saw Manu On Social Media, I Was Laying In Bed And It Was About 11pm, I Literally Couldnt Believe My Eyes.

7 months ago

BeMyHole

stockings, big tits, blonde, first time, hardcore
17:19

Strikingly Stunning T-Girl is Providing me a Flawless Oral Pleasure

3 years ago

TrannyGem

facial, natural, first time
20:18

I Record While I Fuck For The First Time With My Transsexual Girlfriend

3 months ago

BeMyHole

first time
37:57

Sexy traps first Video

2 years ago

XXXDan

blonde, skinny, small tits, first time
33:17

His First Time With A Shemale

1 year ago

ShemaleZ

fetish, MILF, big cock, first time
26:23

Tranny fucks a little trans for the first time on the New Year

1 month ago

JizzBunker

small cock, tattoo, shemale, first time, beauty
26:35 60%

Sissy very first Time Dressing Up For dad

11 months ago

ShemaleMovie

amateur, crossdresser, dress, sissy, first time
1:40:20

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

1 year ago

TrannyOne

first time
25:12

Sexy Ladyboy and Super-Cute Educator Real Guy first-ever Time (นางใน)

2 years ago

KeekAss

asian, redhead, first time, shemale fucks guy
38:26

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

2 years ago

xHamster

MILF, orgasm, nipples, natural, cum in mouth, first time
16:27 70%

Trans girl Selena assfucked for the first time

6 months ago

AShemaleTube

homemade, shemale, crossdresser, first time
22:54

His First Time With A shetwink

5 years ago

ShemaleZ

first time
19:11

My first-ever time in soubrette sissy

4 years ago

HDSex

sissy, first time
53:12 84%

First time anal couple sex blonde tgirl

5 years ago

AShemaleTube

homemade, shemale, anal, couple, ass to mouth, webcam, first time
15:21

Popping your TS Cherry

5 years ago

TrannyGem

femdom, strip, first time
23:23

Fucked for the First Time

2 years ago

TrannyOne

panties, first time, hardcore
38:59

First-Time Fantasy

4 years ago

ShemaleZ

cum in mouth, bareback, first time
18:28

Its time you tasted your first shemale cock

4 years ago

xHamster

first time
15:18

BEGINNER TRANSE ZUM ERSTEN MAL IN DEN ARSCH GEFICKT UND BESAMT ASS JOB

2 years ago

TrannyGem

german, bisexual, riding, nylon, slut, first time
22:07

FIRST-EVER TIME WITH MY FRESH FUCK-FEST MACHINE ASS FUCKING

2 months ago

TrannyGem

solo, british, toys, first time, machine
15:13

Ftm gets pegged by wife for the first time

4 years ago

ShemaleZ

wife, shemale and girl, pegging, first time, FTM

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