SHEMALE • FIRST TIME 532 videos

Popular Latest Top rated

23:44 60%

First-ever time for my hubby plow with Ladyboy

2 years ago

ShemaleTaxi

handjob, bisexual, anal, orgasm, ladyboy, taxi, first time
18:06

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

3 years ago

HomemadeXXX

amateur, first time
1:06:07

Small tits latin gf Valentina anal fucked for the first time

5 years ago

VipTube

first time, solo
15:21

ADULT TIME - Best First Date Ever! Casey Calvert Gobbles Up T-Girl Leilani Li & Takes Creampie!

2 months ago

SomePorn

reality, lesbian, shemale and girl, shemale, creampie, first time
29:01 84%

Ts Bianca (bibibratx) top for the first time with Cristiano

1 month ago

AShemaleTube

shemale, anal, big ass, interracial, big tits, big cock, ass
31:37 79%

Shy Couple first time shemale experience 2

4 years ago

AShemaleTube

couple, shy, first time
16:11 73%

Is this your first time fucking a hot tranny

3 years ago

TrannyOne

first time
51:27 66%

Little ones first time - all 3 angles

4 years ago

TXXX

asian, bareback, first time, amateur
21:06 76%

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

3 years ago

TrannyOne

first time, beauty
17:01

First-ever time topping - t4t personal lovely buttfuck

2 months ago

KeekAss

anal, amateur, shemale, blowjob, first time
20:01 92%

Pretty young tgirl ass fucked for the first time

4 years ago

ShemaleZ

shemale, lingerie, redhead, first time, cumshot, stockings
19:43

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

2 years ago

xHamster

small cock, creampie, 18, small tits, first time
16:30 73%

TS Dominance: Initiation of First Time Subs

8 months ago

TrannyOne

BDSM, shemale, domination, first time
22:23 68%

Fucked For The Very First Time

3 years ago

TrannyOne

first time
35:58 86%

Fresh faced dickgirl masturbates for the first time on cam

8 years ago

TXXX

solo, masturbation, first time
23:10 88%

Fucked For The First Time with Domino Presley

4 years ago

ShemaleZ

first time, shemale fucks guy, MILF
16:30 63%

Teen shemale LOVES first time with boyfriend

9 years ago

TXXX

blowjob, first time, boyfriend
25:12 58%

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

3 years ago

TrannyGem

blowjob, redhead, first time, shemale fucks guy
21:59 82%

Trans nailing a heterosexual stud for the first-ever time

1 year ago

TrannyGem

homemade, reality, first time, shemale fucks guy, amateur
17:35

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

4 years ago

ShemaleMovie

first time, shemale fucks guy
2:25:10 62%

First Time Fembois 2

2 years ago

ShemaleZ

redhead, first time, shemale fucks guy, brunette
16:11

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

5 years ago

TrannyGem

first time, big cock, bareback
17:07 65%

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

11 months ago

TrannyGem

mom, shemale, fat, anal, instruction, facesitting, shemale and girl
18:51 91%

Fucked by a man for the first time.

4 years ago

ShemaleZ

POV, first time, asian, teen (18+)
23:47 67%

Guys first Time with Tgirl

3 years ago

TrannyOne

69, first time
15:57

The first time

1 year ago

AShemaleTube

amateur, POV, first time
18:47

The Pill Episode 2 - Chris First Time

1 year ago

JizzBunker

babe, first time
32:13 53%

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

2 years ago

ShemaleMovie

asian, japanese, first time, crossdresser
22:08 80%

Trans screwing a heterosexual boy for the first-ever time

6 months ago

ShemaleTaxi

amateur, homemade, shemale, blowjob, anal, BDSM, first time
34:39 53%

Trans plowing 2 gals for the first time ~KimberlyGeorge~

2 years ago

VideoSection

shemale, threesome, group, first time
16:00 84%

Femdom Ts Initiation: First Time Fuckers

4 years ago

ShemaleZ

femdom, threesome, first time
17:30

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

10 months ago

JizzBunker

anal, amateur, first time, shemale, couple, mature
32:17 82%

Helena Price - First Time With A Ladyboy Hd

3 years ago

ShemaleZ

shemale, big tits, ladyboy, tattoo, ass licking, first time
19:38

My First-Ever Time with CHICK MAN

5 months ago

TrannyGem

big cock, shemale, creampie, double anal, first time
19:50

Thai Transgender Princess

3 years ago

TrannyGem

asian, first time
18:23 75%

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

9 months ago

xHamster

teen (18+), blowjob, shemale and girl, cumshot, first time, creampie
32:27

Fun and Fabulous: Join Me on My Creativity Journey

Yesterday

XXXDan

teen (18+), crossdresser, shemale, masturbation
46:35

First Time With A Shemale

3 years ago

TrannyOne

first time
40:52 56%

Tall Trans dame penetrated humid By Tiny CIS Girl

6 months ago

ShemaleTaxi

shemale and girl, tall, shemale, first time
43:28 89%

Shelady Very First Time cam

4 years ago

TrannyGem

blowjob, creampie, first time, anal, masturbation
37:05

Young Guy fuck the first Time a Shemale

1 year ago

xHamster

first time
16:53 74%

Senses Like The first-ever Time . . .

4 years ago

ShemaleTaxi

couple, bareback, first time
53:13 60%

TScumshot.com first time anal couple sex tgirls

3 years ago

TrannyOne

couple, first time, BDSM
16:12 60%

Be gentle this is my first time with a tranny

3 years ago

TrannyOne

first time
2:55:43

First Time Fembois

2 years ago

Upornia

stockings, first time
21:45

Guy first time with blonde Tgirl

14 years ago

AShemaleTube

first time, shemale fucks guy
26:35 62%

Sissy very first Time Dressing Up For dad

1 year ago

ShemaleMovie

amateur, crossdresser, dress, sissy, first time
46:35

First Time With A Shemale

4 years ago

BeMyHole

first time, stockings
16:44 53%

My First Time With A Tranny

1 year ago

BeMyHole

creampie, squirt, shemale and girl, domination, first time, cumshot
16:43

Feels Like The First Time . . .

4 years ago

xHamster

first time
33:17 77%

His very first time with a she-creature

2 years ago

KeekAss

MILF, vintage, domination, first time, shemale fucks guy, anal
28:18

Amazing Roxxie Moth Gets Anal Bareback First Time

4 years ago

BeMyHole

cute, stockings, blowjob, first time, hardcore, bareback
16:52

My first Time

3 years ago

TrannyOne

first time
21:31

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

3 years ago

TrannyOne

feet, heels, first time
16:16

This is my first time fucking a shemale babe

4 years ago

xHamster

babe, first time, ladyboy
20:16

First Time Anal with Tundra

2 years ago

TrannyOne

amateur, anal, first time
18:24 76%

The very first time

1 year ago

AShemaleTube

mature, homemade, stockings, shemale, lingerie, crossdresser, sissy
17:25

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

4 years ago

xHamster

mature anal, couple, first time, shemale fucks guy
25:06

Hellos First Time With fantastic lady-twink

5 years ago

ShemaleZ

first time
28:10 77%

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

1 year ago

ShemaleZ

amateur, redhead, girlfriend, first time
15:59 50%

Tranny shag a white fellow in donk

3 years ago

TrannyGem

riding, big cock, mask, first time, cum in ass, shemale fucks guy
15:30

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

1 year ago

xHamster

amateur, couple, shemale and girl, compilation, surprise, cumshot compilation, first time
24:09 83%

Phat Rabbit Killer My First Time

4 years ago

HClips

ebony, interracial, tattoo, ass licking, first time
18:47

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

4 years ago

BeMyHole

dogging, mask, dress, first time
15:21

Boy gets to fuck a CD for the first time

6 years ago

xHamster

couple, lingerie, first time
15:10

My first time as a sissy was so liberating

2 years ago

ShemaleTaxi

crossdresser, taxi, first time, sissy
16:05 60%

Inexperienced real en motel de guerrero. pornography en español!

9 months ago

ShemaleTaxi

homemade, black, small cock, arab, creampie, anal, big ass
22:46 50%

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

3 years ago

TrannyOne

feet, ass to mouth, cum in mouth, sissy, first time, cum in ass
15:31

Guy gets to screw a CD for the very first time

4 years ago

ShemaleMovie

first time
19:36

Pretty young tgirl ass fucked by girl for the first time

4 years ago

TXXX

POV, first time, shemale and girl
32:59 40%

Helena Price 1st Time Transgender dame

1 year ago

ShemaleTaxi

shemale, first time
16:27 82%

Trans girl Selena assfucked for the first time

1 year ago

AShemaleTube

homemade, shemale, blowjob, lingerie, crossdresser, shemale and girl, first time
15:34 89%

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

1 month ago

xHamster

compilation, asian, solo, masturbation, first time
17:57 67%

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

2 years ago

ShemaleTaxi

ladyboy, domination, skinny, first time
15:21

Popping your TS Cherry

6 years ago

TrannyGem

femdom, strip, first time
28:31

Roxxie Cracking In A First-Ever Timer

4 years ago

TrannyGem

first time
20:47

First time sucking and fucking

3 years ago

TrannyOne

crossdresser, first time
44:37

Sex Tourist Bangs A Shemale For The First Time

3 years ago

HClips

threesome, first time, brunette
16:19

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

3 years ago

TrannyGem

brazil, teen anal (18+), first time
15:37

First Time Eating Ass

2 years ago

Upornia

first time
37:57 73%

Sexy traps first Video

3 years ago

XXXDan

blonde, skinny, small tits, first time
29:07

Teaching str8 young boy first time ladyboy experience

7 years ago

ShemaleZ

ladyboy, first time
39:29

Sharnell Dupree - First-time Fantasy

4 years ago

TXXX

first time, asian
21:50

Trans Fucking A Straight Boy For The First Time

1 year ago

ShemaleZ

BDSM, first time
1:00:28 53%

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

8 months ago

HClips

amateur, creampie, old man, POV, asian, shemale and girl, shy
1:02:42 61%

First Time Visit To The Gloryhole For This attractive playgirl

5 years ago

ShemaleZ

gloryhole, first time
38:29 67%

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.

1 year ago

BeMyHole

stockings, big tits, tattoo, 18, blonde, first time, hardcore
28:27

My trans gf screws me for the first-ever time. She loves how she fucks my ass

1 year ago

ShemaleTaxi

amateur, blowjob, girlfriend, first time, shemale fucks guy, homemade
44:40 59%

Indian Taina - My First Time With An Indian

2 years ago

ShemaleZ

ebony, indian, shemale, interracial, big cock, first time
25:12

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

3 years ago

KeekAss

asian, redhead, first time, shemale fucks guy, cute, ladyboy
16:51

My first Time

7 years ago

AShemaleTube

POV, first time
29:19

The first Time Kisses Came Upon Rio

5 years ago

TXXX

kissing, first time, amateur
22:54

His First Time With A shetwink

6 years ago

ShemaleZ

first time
19:58 66%

MY FIRST TIME FUCK BEAUTIFUL SHEMALE ON UPSTAIRS

2 years ago

xHamster

beauty, small cock, creampie, anal, interracial, bareback, small tits
17:15

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

3 years ago

ShemaleZ

ladyboy, skinny, first time, brunette
25:56

Katerin Britz - The First Time Is Always Intense

10 months ago

HClips

stockings, big ass, shemale, ass, first time
15:28

Brunette gets Pegged by Wife for the first Time

4 years ago

TrannyGem

wife, clit, big clit, erotic, pegging, first time, sensual
20:31

Blonde for the first time

7 years ago

TXXX

first time
16:43

Feels Like The First Time

3 years ago

ShemaleZ

first time
29:52

Lad has his first time with very hot TS

13 years ago

AShemaleTube

first time
15:27

ADULT TIME - hottest very first rendezvous Ever! Casey Calvert Gobbles Up T-Girl Leilani Li & Takes DEEP Creampie!

2 months ago

ShemaleTaxi

shemale, creampie, shemale and girl, big ass, first time
15:54

SOMEONES SPUNKING

3 years ago

TrannyGem

strip, goth, first time
18:28

Its time you tasted your first shemale cock

5 years ago

xHamster

first time
23:46

Guys first Time with Tgirl

4 years ago

BeMyHole

kissing, nipples, 69, panties, jeans, first time, shemale fucks guy
53:12 84%

First time anal couple sex blonde tgirl

6 years ago

AShemaleTube

homemade, shemale, blowjob, anal, couple, ass to mouth, webcam
15:51 75%

ADULT TIME - Straight Girl Kenzie Taylor First Trans Fuck With Big Titty T-Girl Brittney Kad

6 months ago

AShemaleTube

shemale, shemale and girl, big tits, first time, 18
22:35

Tgirl fucks Tboy with pussy ................Pussyboy get fucked for first time

3 years ago

TXXX

first time
19:46

MidLife Crisis (v0.30) - Middled age stud creampied for very first time (three)

2 years ago

TrannyGem

teen anal (18+), game, 18, wet, anime, cartoon, first time
23:19

First Time For My Husband Fuck With Ladyboy

1 year ago

Upornia

amateur, teen (18+), asian, husband, first time, ladyboy
22:00

Ts In Stockings Ingrid Moreira The First Time

3 years ago

BeMyHole

piercing, condom, shaving, first time, shemale fucks guy, lingerie
1:40:20

My first time with a transexual Full Hd Version Directors Cut

1 year ago

JizzBunker

first time
21:03 47%

T Gurl Cums in her dress

4 years ago

xHamster

public, shemale, outdoor, dress, cumshot compilation, first time
16:06

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

1 year ago

KeekAss

blowjob, crossdresser, first time
38:59

First-Time Fantasy

5 years ago

ShemaleZ

cum in mouth, bareback, first time
38:26

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

3 years ago

xHamster

MILF, orgasm, nipples, natural, cum in mouth, first time
18:44

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

11 months ago

ShemaleMovie

stockings, blowjob, anal, lingerie, ass, heels, first time
15:13 40%

Ftm gets pegged by wife for the first time

5 years ago

ShemaleZ

wife, shemale and girl, pegging, first time, FTM
33:17

His First Time With A Shemale

2 years ago

ShemaleZ

fetish, MILF, big cock, first time
15:57

Yvanas First Time On Porn - Alexandra Bxl

2 years ago

ShemaleZ

stockings, lingerie, first time
15:21

ADULT TIME - Hottest Very first Rendezvous Ever Casey Calvert Tongues Up T-Nymph Leilani Li Takes DEEP Internal ejaculation

2 months ago

KeekAss

big ass, first time

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