SHEMALE • FIRST TIME 777 videos

Popular Latest Top rated

27:22 96%

Bashful lean ladyboy very first time on camera

3 months ago

ShemaleTaxi

shemale, anal, ladyboy, first time
52:24 95%

Trans Welcome Gonzo First Time Double Butt - Vanessa Jhons

4 years ago

ShemaleZ

handjob, big ass, interracial, MILF, big tits, tattoo, toys
24:14 94%

First Time With Jacuzzi... OMG

1 month ago

AShemaleTube

big tits, ebony, shemale, first time
20:01 93%

Pretty young tgirl ass fucked for the first time

5 years ago

ShemaleZ

stockings, shemale, lingerie, redhead, cumshot, ass, first time
44:17 92%

Kendall Penny - Southern Sass Submits For The First Time!

3 years ago

ShemaleZ

stockings, fetish, BDSM, ass, first time, brunette
20:43 92%

My first time dominated by scorching light-haired t-girl LaraMCX

3 days ago

ShemaleMovie

cum in mouth, shemale fucks guy, anal, teen anal (18+), shemale, teen (18+), amateur
21:31 92%

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

4 years ago

TrannyOne

feet, heels, first time, fetish
20:04 91%

TGIRL POST-OP: Jenny Loves Her New Pussy Fucked

4 years ago

xHamster

couple, interracial, ass, first time, post op, anal
20:33 91%

My first time getting dominated by a hot blonde trans babe

5 months ago

XXXVogue

blowjob, anal, big tits, BDSM, blonde, babe, ass
46:35 91%

First Time With A Shemale

5 years ago

BeMyHole

first time, stockings, hardcore
15:27 91%

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

1 year ago

ShemaleTaxi

shemale, creampie, shemale and girl, big ass, first time
35:58 91%

Fresh faced dickgirl masturbates for the first time on cam

9 years ago

TXXX

solo, masturbation, first time
23:57 90%

My Stepbrother Sleeps With Me And Ends Up Fucking A Beautiful Trans Girl - MarilyDaniela

1 month ago

BeMyHole

amateur, beauty, shemale, blowjob, bisexual, anal, big ass
39:35 90%

Skinny Asian Ladyboys First Time On Camera

2 years ago

ShemaleZ

small cock, asian, ladyboy, skinny, small tits, first time
16:00 90%

Femdom Ts Initiation: First Time Fuckers

5 years ago

ShemaleZ

femdom, threesome, first time, fetish
19:51 89%

T-Model teenager with yam-sized pink cigar lets dude plow her in the butt

3 years ago

TrannyGem

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19:52 89%

Shemale teen with big schlong lets stud shag her in the ass

1 year ago

ShemaleMovie

big ass, skinny, sissy, first time, cum in ass
20:49 89%

Big Tits First Timer Gets His Ass Fucked From The Tranny!

2 years ago

BeMyHole

bisexual, big ass, brazil, big tits, latina, domination, first time
18:50 89%

AUBREYS FIRST-EVER TIME

5 years ago

TrannyGem

shemale, first time
28:15 88%

My trans gf penetrates me for the very first time. She I love how she plows my caboose

2 years ago

KeekAss

blowjob, anal, ladyboy, crossdresser, girlfriend, bareback, small tits
24:41 88%

Cunty bride hook up BBC for first time

3 months ago

AShemaleTube

amateur, bride, shemale, anal, interracial, big cock, domination
52:54 88%

Trans Vanessa Jhons welcome Gonzo first time double anal

5 years ago

TXXX

anal, big tits, BDSM, double anal, gangbang, big cock, orgy
29:11 88%

Transsexual Bianca (bibibratx) top for the first-ever time with Cristiano

8 months ago

ShemaleTaxi

teen (18+), big ass, teen anal (18+), BDSM, tattoo, piercing, big cock
17:56 88%

Legacy Mess: bony transgender princess humps a guy for the first time. P2

8 months ago

ShemaleMovie

thai, couple, BDSM, ladyboy, domination, skinny, first time
18:53 88%

Made His First Time Memorable - Anastasia Penny

2 years ago

ShemaleZ

cumshot, big cock, first time
16:20 88%

ADULT TIME - T-nymph Brittney Kade Fufills Besties Bucket List tear up By Topping Him & eating His Ass

7 months ago

VideoSection

ass, shemale fucks guy, shemale, first time, domination
21:17 87%

I went to pulverize a trans with a good-sized jizz-shotgun and finished up being violated into by her in the end.

10 months ago

TrannyGem

creampie, muscle, big tits, blonde, big cock, futanari, first time
33:49 86%

Tgata Manuella Gonçalves Did Whatever She Wanted While Riding With Alex Victor.

10 months ago

BeMyHole

amateur, public, blowjob, anal, big ass, car, latina
33:58 86%

For the first-ever time he put the metal in the trans - Isa Oliveira

3 months ago

KeekAss

handjob, shemale, first time
25:54 86%

First time BBC

6 years ago

ShemaleZ

interracial, big tits, BBC, first time
39:15 86%

Cute shemale girl gets anal fucked for the first time

3 years ago

xHamster

cute, first time
18:15 86%

FEMALE DOMINATION HANDBALLING ASSFUCKING INSTRUCTING PEGGING DOMINATRIX PREDOMINANCE FEMBOY

4 years ago

TrannyGem

femdom, train, instruction, wife, fisting, bondage, dildo
18:24 85%

The very first time

2 years ago

AShemaleTube

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16:27 85%

Trans girl Selena assfucked for the first time

2 years ago

AShemaleTube

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30:27 85%

Skinny she-male gets insatiable anal fucked in the small ass

11 months ago

VideoSection

anal, asian, 18, ass, skinny, first time, missionary
19:12 85%

CD TRANSSEXUAL FIRST-EVER BIG BLACK COCK !! HE CAME INWARDS of Me TWO TIMES!!! WARM PUBLIC SISSY

4 years ago

TrannyGem

public, dogging, BBC, first time, crossdresser
21:39 85%

Jamie French And Erica Cherry Fuck For The First Time And They Fuck Hard! Ots764

5 years ago

TXXX

french, first time, cumshot
46:35 85%

First Time With A Shemale

4 years ago

TrannyOne

first time
25:40 84%

Ebony tranny wants his virgin asshole

5 months ago

XoZilla

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24:51 84%

Cunty bride meet up big black cock for first-ever time

3 months ago

ShemaleMovie

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32:51 84%

French tgirl : his first time with a sexy dicky girl

5 years ago

AShemaleTube

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18:29 83%

First time getting fingered before taking the dildo in

2 months ago

XXXVogue

handjob, amateur, beauty, shemale, anal, couple, russian
39:41 83%

Skinny Asian ladyboys first time on camera

2 years ago

xHamster

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30:15 83%

Femout XXX: Nurse Kays First Time on Film

4 months ago

$$ FapHouse

shemale, anal, couple, first time
28:18 83%

Amazing Roxxie Moth Gets Anal Bareback First Time

5 years ago

BeMyHole

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19:39 83%

Horny Danish Boy - His First Time

4 months ago

BeMyHole

blowjob, anal, ass licking, danish, first time, hardcore
22:55 83%

My first time!

2 years ago

XXXDan

teen (18+), teen anal (18+), first time
16:42 83%

I Recently Acquired A Giant Tentacle Dildo, And In This Video I Use It For The First Time

2 years ago

BeMyHole

amateur, stockings, dildo, solo, tentacle, first time
33:17 83%

His First Time With A Shemale

3 years ago

ShemaleZ

fetish, MILF, big cock, first time
28:17 83%

My trans girlfriend fucks me for the first time. She loves how she fucks my ass

2 years ago

xHamster

homemade, ladyboy, first time, shemale fucks guy, latina, amateur
53:12 83%

First time anal couple sex blonde tgirl

7 years ago

AShemaleTube

homemade, anal, couple, ass to mouth, webcam, first time, frottage
24:09 83%

Phat Rabbit Killer My First Time

5 years ago

HClips

ebony, interracial, tattoo, ass licking, first time, amateur
21:36 83%

Trans Fucking A Straight Boy For The First Time

9 months ago

BeMyHole

blowjob, BDSM, redhead, ass licking, reality, first time, shemale fucks guy
15:56 82%

RUSSIAN FEMBOY TEARS UP WITH DOMME FOR THE VERY FIRST TIME WITH a YAM-SIZED BELT DICK, STRAPPED WITH a INNOCENCE

4 years ago

TrannyGem

femdom, strapon, mature anal, russian, fisting, bondage, pegging
21:59 82%

Trans nailing a heterosexual stud for the first-ever time

2 years ago

TrannyGem

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43:28 82%

Shelady Very First Time cam

5 years ago

TrannyGem

blowjob, creampie, anal, webcam, small tits, first time
23:44 82%

Her first time with a Shemale

8 years ago

xHamster

lingerie, first time, shemale and girl, big cock
32:17 82%

Helena Price - First Time With A Ladyboy Hd

4 years ago

ShemaleZ

shemale, big tits, ladyboy, tattoo, crossdresser, ass licking, first time
15:32 82%

Russian Femboy Fucks With Mistress For The First Time With A Huge Strapon Tied With A Chastity

4 years ago

ShemaleZ

femdom, strapon, russian, fisting, BDSM, tied, first time
28:10 82%

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

2 years ago

ShemaleZ

amateur, redhead, girlfriend, first time
27:09 82%

First Time Indian Shemale Fucking Desi Babe In Office

4 years ago

TrannyOne

indian, office, spandex, first time
27:53 82%

Anastasia Penny – He Hired An Escort For The First Time

3 years ago

Upornia

big tits, lingerie, first time, escort, interracial
22:58 82%

AI-nosey - sequence 1: first-ever Times (Big Johnson)

5 years ago

ShemaleTaxi

cartoon, taxi, first time, shemale
15:53 82%

Vol #10: screwed For The very first Time on Femout

6 months ago

ShemaleTaxi

big cock, shemale fucks guy, small cock, kissing, first time, deepthroat
16:43 82%

Feels Like The First Time . . .

4 years ago

TrannyOne

skinny, first time, anal
15:18 82%

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

4 years ago

TrannyGem

german, bisexual, crossdresser, riding, nylon, slut, first time
15:34 81%

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

1 year ago

xHamster

compilation, asian, solo, masturbation, first time, shemale
23:10 81%

Fucked For The First Time with Domino Presley

5 years ago

ShemaleZ

first time, shemale fucks guy, MILF
29:36 80%

Teaching str8 young boy first time ladyboy experience

8 years ago

AShemaleTube

erotic, first time
16:37 80%

First Time Topping - T4t Intimate Cute Anal

1 year ago

HClips

shemale and girl, cute, amateur, shemale, POV, first time
4:12:46 80%

Oots-015 Sensitive Cosplayer Who Gets Her Anus Penetrated And Writhes In Agony. Anal Masturbation, Deep Throat, Sensitive, First Time Filming, Female Orgasm, Ahegao, Lesbian, Anal Sex, Lotion Play, Pov, Doujinshi, Cosplay, Cosplayer, Big Cock, 3p, Fa

11 months ago

ShemaleZ

teen (18+), lesbian, POV, teen anal (18+), orgasm, lingerie, first time
25:56 80%

Katerin Britz - The First Time Is Always Intense

1 year ago

HClips

stockings, big ass, shemale, ass, first time
23:45 80%

First-time solo webcam pleasure session

8 months ago

XXXVogue

first time, solo, amateur, big cock, webcam
17:39 80%

Huge Cock Ts Shemale Fuck Latina Teen Girl First Time

4 years ago

Upornia

shemale and girl, first time, mom
15:21 80%

Handballing bondage with cum-shot

4 months ago

ShemaleMovie

fisting, bondage, sissy, BDSM, heels
31:37 80%

Shy Couple first time shemale experience 2

6 years ago

AShemaleTube

couple, shy, first time, shemale
23:22 80%

Fucked for the First Time

5 years ago

BeMyHole

femdom, latex, anal, dogging, panties, first time, shemale fucks guy
17:21 80%

I Fuck A Tranny Girl For The First Time 4k

3 years ago

ShemaleZ

big ass, big tits, shemale and girl, first time, anal orgasm, brunette
33:17 79%

His very first time with a she-creature

3 years ago

KeekAss

MILF, vintage, domination, first time, shemale fucks guy, anal
39:11 79%

A nosey woman tries a shemales spunk-pump for the very first time

4 years ago

ShemaleTaxi

shemale and girl, pump, taxi, first time, big cock
15:21 79%

ADULT TIME - Lonely T-Girl Emma Rose Has First Romantic Suck And Fuck With Big Dick Roommate!

11 months ago

SomePorn

blowjob, dogging, ass licking, cumshot, ass, deepthroat, reality
16:17 79%

Ts Madisons massive cock takes on a guy for the first time on cam

7 months ago

XXXVogue

shemale fucks guy, ebony, big cock, domination, first time, big tits
22:08 79%

Trans screwing a heterosexual boy for the first-ever time

1 year ago

ShemaleTaxi

amateur, shemale, blowjob, anal, BDSM, first time
21:52 78%

Brand New Trans Cutie Pixie Pond Fucked by a Man for the First Time Ever

9 months ago

$$ FapHouse

amateur, shemale, blowjob, POV, anal, couple, interracial
18:19 78%

Barbie Femmes Dont Need A Ken. They Have Their Own Peckers

1 year ago

TrannyGem

teen (18+), creampie, 18, shemale and girl, masturbation, big cock, babe
26:00 78%

First-time blowjob experience with big cock in missionary position featuring Jessica Kate

8 months ago

XXXVogue

amateur, spanish, big ass, big cock, ass, first time, missionary
15:26 78%

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

1 year ago

xHamster

big ass, shemale and girl, shemale, first time, creampie
15:59 78%

Mama Studio introduces Training my step nephew to lick a trans for the first-ever time - Free-for-all

3 weeks ago

TrannyGem

amateur, mom, creampie, train, anal, brazil, latina
17:52 78%

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

4 years ago

TrannyOne

first time, hardcore
35:17 78%

The First Time Married To A Trans Girl

11 months ago

HClips

POV, lingerie, shemale and girl, bareback, first time, brunette
22:32 78%

First time BBC FTM Transman Ethan Hawk

5 years ago

xHamster

couple, BBC, first time, FTM
18:23 77%

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

1 year ago

xHamster

teen (18+), blowjob, shemale and girl, cumshot, first time, creampie
15:15 77%

VERY FIRST TIME TRANSGENDER PLOWED IN BOOTY AND CREAMPIED

2 years ago

KeekAss

amateur, stockings, creampie, bareback, first time, webcam
20:32 76%

Big-ass trans tramp gets it good from ultra-cute femboy prettyboi2000x

3 months ago

XXXVogue

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17:26 76%

Alexandra Bxl In Young Guy Fucked In The Ass For The First Time By A Tranny

5 years ago

ShemaleZ

mature, first time, shemale fucks guy, shemale, amateur
16:30 76%

TS Dominance: Initiation of First Time Subs

1 year ago

TrannyOne

BDSM, shemale, domination, first time
16:12 76%

Stephie scarlet first time pegging a tgirl

2 years ago

IcePorn

pegging, first time, amateur
1:29:57 76%

M584G02 son who has returned for the first time in a few years is a transcendental transsexual.

2 years ago

xHamster

bisexual, orgasm, japanese, cum in mouth, first time
21:06 76%

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

4 years ago

TrannyOne

first time, beauty
20:56 75%

Very first time deep throating and smashing … $$$

6 months ago

ShemaleMovie

first time, crossdresser, shemale, deepthroat, 18
16:31 75%

ChristyEvans asks me to be her first-ever time and put my rock-hard lollipop in her and get her pregnant

6 months ago

ShemaleMovie

shemale, creampie, first time, pregnant
34:12 75%

Watch fine-looking Silvana Lee and Lizzy Laynezs porn

1 year ago

PornHat

latina, shemale and girl, first time, shemale, cuckold, colombian
18:14 75%

Pure TABOO asian cherry Lulu Chu Gets ALIEN DICK DRAINED By Stepmom Penny Barber & Dr. Sophia Locke!

5 months ago

ShemaleMovie

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25:51 75%

Five Cocks for her First Time

6 months ago

NuVid

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30:05 75%

White tranny takes BBC for first time

7 years ago

TXXX

interracial, BBC, first time
34:12 75%

Milf Silvana Lee has Hardcore Sex with Her Brothers Sexy Shemale Girlfriend ...

1 year ago

Beeg

shemale, cuckold, first time, girlfriend, dogging, latina
17:39 75%

Huge Cock TS Shemale Fuck Latina Teen Girl First Time

6 years ago

xHamster

teen (18+), german, bisexual, teen anal (18+), shemale and girl, 69, asshole
18:49 75%

Unseen Hook-Up Movies Cumpilation - Onlyfans Veronica Sanders

2 years ago

TrannyGem

homemade, POV, anal, russian, interracial, shemale and girl, compilation
18:51 74%

Fucked by a man for the first time.

5 years ago

ShemaleZ

POV, first time, asian, teen (18+)
30:46 74%

Jamie French And Bambi Bliss - First Time Ots846

4 years ago

ShemaleZ

shemale, french, ass licking, first time, stockings
17:57 74%

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

3 years ago

ShemaleTaxi

ladyboy, domination, skinny, first time
16:53 74%

Senses Like The first-ever Time . . .

5 years ago

ShemaleTaxi

couple, bareback, first time
39:01 73%

A curious woman tries a shemale's cock for the first time

4 years ago

xHamster

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16:30 73%

Fancy womans small tits sex

2 months ago

PornHat

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24:59 73%

Old Futa Girl-On-Girl Tranny Humps Young Very First Time Cherry With Numerous Ejaculations - Sims four

2 years ago

TrannyGem

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20:11 73%

Pretty young tdamsel butt drilled by girl for the first time

5 years ago

ShemaleTaxi

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15:51 73%

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

1 year ago

AShemaleTube

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37:57 73%

Sexy traps first Video

4 years ago

XXXDan

blonde, skinny, small tits, first time
22:23 73%

Fucked For The Very First Time

4 years ago

TrannyOne

first time
29:55 73%

Ananda India Took Our Ride And Exchanges With Our Friend Alex Victor

7 months ago

BeMyHole

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