SHEMALE • FIRST TIME 4,063 videos

Popular Latest Top rated

09:47 94%

MILF Stepmom Let Stepsons TS GF Fuck Her Asshole

3 months ago

BeMyHole

mom, blowjob, big ass, MILF, ladyboy, ass licking, shemale and girl
20:04 93%

TGIRL POST-OP: Jenny Loves Her New Pussy Fucked

4 years ago

xHamster

couple, interracial, ass, first time, post op, anal
20:33 93%

My first time getting dominated by a hot blonde trans babe

2 months ago

XXXVogue

shemale, blowjob, anal, big tits, BDSM, blonde, babe
09:44 92%

Futanari doe visits Fira for a wild breeding lesson in Centaur Things

3 months ago

XXXVogue

cartoon, futanari, cumshot
09:46 91%

LIL Young Transgirl Sissy gets RODE by wall plaything for the VERY FIRST TIME

2 years ago

TrannyGem

dildo, 18, cumshot, babe, college, toys, sissy
10:46 90%

Transexual Brandy Alexander gets fucked and facialized for the first time

7 years ago

ShemaleZ

facial, first time
07:32 90%

Futanari stepdaughter has her first anal time with her horny mommy [Hentai Uncensored]

2 years ago

MyLust

mom, anal, MILF, orgasm, futanari, first time
10:12 90%

My Teen 18+ Stepsister Wants To Try A Cock For The First Time 10 Min - Amanda Riley And Steve Rickz

11 months ago

ShemaleZ

small cock, shemale, 18, first time, small tits
10:57 90%

LEGACY MESS : Filipino fuckslut With Big Cock for the first time in pornography muddy Fucks deep hard in the Throat and Ass of her Partner

2 years ago

ShemaleTaxi

asian, BDSM, ladyboy, big cock, deepthroat, filipina, domination
16:00 89%

Femdom Ts Initiation: First Time Fuckers

5 years ago

ShemaleZ

femdom, threesome, first time, fetish
19:12 89%

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
05:55 89%

Premiere: Ashley Is Fucked By A Shemale And Swallows For The First Time Transsexual Sperm! 6 Min With Ashley Cumstar And Rosella Extrem

3 years ago

ShemaleZ

sperm, swallow, group, cum in mouth, first time, fetish
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
03:06 88%

GROOBYGIRLS - Eris Jolie First Time Sexy Performance

1 year ago

TrannyGem

solo, nipples, strip, masturbation, jeans, first time
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.

8 months ago

TrannyGem

creampie, muscle, big tits, blonde, big cock, ass, futanari
05:08 87%

Dude for the first time gets shemales male stick

6 years ago

Analdin

swinger, party, fetish, first time, hardcore, ladyboy
08:07 86%

I try my transsexual friends cock for the first time

1 year ago

PornDr

handjob, beauty, blowjob, german, wife, cumshot, masturbation
14:39 86%

Ride With A Beautiful & Wonderful Tranny Isabella Salvatore

7 months ago

BeMyHole

beauty, public, big tits, car, 18, jerking, riding
18:15 86%

FEMALE DOMINATION HANDBALLING ASSFUCKING INSTRUCTING PEGGING DOMINATRIX PREDOMINANCE FEMBOY

4 years ago

TrannyGem

femdom, train, instruction, wife, fisting, bondage, dildo
06:32 86%

Your First Time Getting Fucked by a Trans nymph: First rendezvous GFE point of view Femdom

2 years ago

ShemaleTaxi

femdom, asian, filipina, domination, first time, kissing
08:07 86%

Car Toon And 3d Animated - Shemale Stepsister Persuaded Stepbrother For Anal Sex For A Long Time, And The Guy Agreed To Take Her Small Dick. Then The Guy Liked It When He Was Fucked In The Ass For The First Time Futa On Male. 8 Min

1 year ago

ShemaleZ

ladyboy, shemale fucks guy, 3D, first time, small cock
03:06 86%

FEMOUT XXX - Angel Monroe First Time To Exposed Her Goodies

1 year ago

AShemaleTube

first time, selfsuck, masturbation, interracial
06:26 86%

Trans Lesbians first-ever Time Together

3 years ago

ShemaleTaxi

shemale, lesbian, taxi, first time
10:36 86%

First-ever time assfucking. Lovely Transgirl plays with herself. Sploog ejaculation

2 years ago

KeekAss

amateur, anal, solo, cumshot, masturbation, first time
06:20 85%

Tgirl Emma Roses first time with a woman

1 year ago

KeekAss

first time, shemale and girl, lingerie, big tits
15:53 84%

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

3 months ago

ShemaleTaxi

big cock, shemale fucks guy, small cock, kissing, first time, deepthroat
53:12 84%

First time anal couple sex blonde tgirl

7 years ago

AShemaleTube

homemade, anal, couple, ass to mouth, webcam, first time, frottage
18:24 84%

The very first time

2 years ago

AShemaleTube

mature, homemade, stockings, shemale, lingerie, crossdresser, sissy
07:37 84%

Cutiepii33quinn Gets Her Cherry Arse Nailed For Very First Time

4 months ago

PePorn

POV, amateur, first time
06:06 83%

Whats Russian For Suck My Cock? First Time Girl Fucked By Ts Teacher - Lora Hoffman

1 week ago

ShemaleZ

teacher, small cock, russian, shemale and girl, shemale
17:56 83%

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

6 months ago

ShemaleMovie

thai, couple, BDSM, big cock, domination, skinny, first time
30:27 83%

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

8 months ago

VideoSection

shemale, anal, asian, 18, ass, skinny, first time
12:08 83%

My First Time With A Trans

2 years ago

BeMyHole

amateur, big tits, ass licking, first time, hardcore
13:59 83%

TRANSFIXED - Whitney Wright Helps Hot Redhead Erica Cherry Explore New Pleasures On Their First Date

2 years ago

xHamster

shemale, shemale and girl, first time
28:18 83%

Amazing Roxxie Moth Gets Anal Bareback First Time

5 years ago

BeMyHole

cute, stockings, blowjob, first time, hardcore, bareback
13:24 83%

Petite tranny undresses for the first time and shows what a horny cock she has

3 years ago

xHamster

handjob, orgasm, japanese, nipples, first time, japanese uncensored
03:06 83%

FEMOUT XXX - Jaede First Time Solo Masturbation Reveals

1 year ago

AShemaleTube

solo, masturbation, first time
07:37 83%

First time in the Ass iwant a doggy style!

1 year ago

AShemaleTube

cumshot, amateur, first time
14:58 83%

My first time with a trans girl !!

1 year ago

xHamster

amateur, homemade, teen (18+), shemale, bisexual, lingerie, shemale and girl
32:17 82%

Helena Price - First Time With A Ladyboy Hd

4 years ago

ShemaleZ

big tits, ladyboy, tattoo, crossdresser, ass licking, first time
32:51 82%

French tgirl : his first time with a sexy dicky girl

4 years ago

AShemaleTube

french, outdoor, ass to mouth, shemale and girl, blonde, first time
04:30 82%

Topping a guy friend for the first time!!!

4 years ago

TrannyOne

first time
15:18 82%

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

3 years ago

TrannyGem

german, bisexual, crossdresser, riding, nylon, slut, first time
16:43 82%

Feels Like The First Time . . .

4 years ago

TrannyOne

skinny, first time, anal
08:12 81%

My first time with a real shemale

2 years ago

XXXDan

brazil, orgasm, facial, 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
04:50 80%

Inexperienced Teen Fuck My Ass For The First Time, Did He Cum Quickly?

2 years ago

BeMyHole

teen (18+), creampie, chubby, teen anal (18+), BBW, nipples, first time
03:06 80%

Transgender scene with sultry fiancée from Grooby Girls

4 months ago

PornHat

feet, solo, first time, nipples, glasses, jeans
10:06 80%

Dorian Drake gets barebacked for the first time by big cock from trans girl pv

2 weeks ago

AShemaleTube

amateur, homemade, shemale, fetish, big cock, first time, femboy
06:08 80%

Curvy Black Trap Twerking and Tugging

7 years ago

TrannyGem

chubby, piercing, shaving, first time
23:45 80%

First-time solo webcam pleasure session

5 months ago

XXXVogue

first time, solo, amateur, big cock, webcam
33:58 80%

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

3 weeks ago

KeekAss

handjob, shemale, first time
07:18 80%

TGirl fucks Step sister booty For The First Time

10 months ago

VideoSection

tattoo, blonde, shemale, first time
03:12 80%

Crossdresser Fucks Uncle for First Time

7 years ago

ShemaleZ

uncle, first time, crossdresser
06:15 80%

Straight guys first time to fuck tranny

2 years ago

TrannyOne

first time
14:15 80%

Beautiful shemale pounds the guys ass bareback for the first time

4 years ago

TrannyOne

first time
05:00 80%

Post-Op Ladyboy Beauty Natty Fucked Bareback

2 years ago

BeMyHole

beauty, teen (18+), creampie, POV, 18, panties, first time
03:06 80%

Genevieves short skirt sex by Grooby Girls

2 months ago

PornHat

small cock, solo, cute, masturbation
05:26 80%

White Tranny Trying BBC For First Time

6 years ago

ShemaleZ

first time
11:34 80%

Sissy trans Artemis Asteria gets intimate with roommate for the first time

2 years ago

AnySex

handjob, shemale, blowjob, sissy, first time, small tits
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
02:57 79%

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

1 year ago

AnySex

amateur, POV, blowjob, anal, first time, boyfriend
23:22 79%

Fucked for the First Time

5 years ago

BeMyHole

femdom, latex, anal, dogging, panties, first time, shemale fucks guy
08:14 79%

Trans Taking an anal chastity

8 months ago

ShemaleMovie

anal, BDSM, crossdresser, british, big cock, bareback, sissy
08:09 79%

My very first time

4 years ago

TrannyOne

first time
06:00 79%

First time anal bareback for this amateur teen ladyboy

6 years ago

AShemaleTube

small cock, asian, ladyboy, first time
15:21 78%

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

9 months ago

SomePorn

blowjob, dogging, ass licking, cumshot, ass, deepthroat, reality
39:11 78%

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

3 years ago

ShemaleTaxi

shemale and girl, pump, taxi, first time, big cock
06:02 78%

Filipino Femboy Has First Time Bareback Anal Sex On Camera

4 years ago

ShemaleZ

filipina, first time, femboy
12:29 78%

Shy Latino First Time With A Shemale

6 years ago

TXXX

shy, first time
10:38 78%

My first-ever ever 3some!!!

6 months ago

ShemaleMovie

amateur, beauty, shemale, double anal, blonde, big cock, babe
09:39 78%

My first time with a trans. Part 3. I fuck her nice ass

2 years ago

JizzBunker

teen (18+), teen anal (18+), latina, first time, couple, amateur
15:26 77%

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
05:14 77%

Trans has her first time with her step cousin

2 years ago

ShemaleTaxi

amateur, homemade, anal, cousin, first time, shemale
12:05 77%

Beauty Fucks For Her First Time With A Trans And Its With Spencer Bradley

3 years ago

ShemaleZ

amateur, beauty, shemale and girl, first time
15:15 77%

VERY FIRST TIME TRANSGENDER PLOWED IN BOOTY AND CREAMPIED

2 years ago

KeekAss

amateur, stockings, creampie, bareback, first time, webcam
07:18 76%

Ebony transsexual Trea Rich gets filled up

2 months ago

XXXVogue

black, ebony, shemale
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
04:04 76%

Anal Fisting First Time

3 years ago

ShemaleZ

teen (18+), teen anal (18+), fisting, first time
09:30 76%

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

1 year ago

Upornia

asian, shemale, interracial, big cock, first time
04:31 76%

Assfucking Internal Ejaculation Gushes Out Onto Camera As Lil Trans Gets Plumbed

2 months ago

TrannyGem

amateur, cute, shemale, creampie, anal, fetish, dogging
05:32 75%

Post-Op Thai Shemale Meiji Pussy Bareback

2 years ago

BeMyHole

shemale, creampie, asian, first time, post op, thai
12:53 75%

She made me spunk two times! Very First time fuckin Britney from Tantaly - Emily Adaire

2 months ago

TrannyGem

amateur, stockings, doll, german, cumshot, masturbation, nylon
35:17 75%

The First Time Married To A Trans Girl

8 months ago

HClips

POV, lingerie, shemale and girl, bareback, first time, brunette
06:25 75%

Ladyboy Amy Fucks Guys Ass For The First Time

3 years ago

DrTuber

blowjob, POV, asian, first time, shemale fucks guy
08:07 75%

TRANSSEXUAL Kim Wagner bangs a young homo, it is him first-ever time

11 months ago

TrannyGem

cumshot, first time, creampie, old man, german, old and young (18+)
30:05 75%

White tranny takes BBC for first time

7 years ago

TXXX

interracial, BBC, first time
11:11 75%

Meaty fake penis destroys my little cootchie

1 year ago

ShemaleTaxi

feet, beauty, dildo, uniform, girlfriend, babe, penis
09:02 74%

J want you to take me like this!

3 months ago

ShemaleTaxi

amateur, shemale, french, lingerie, solo, taxi, first time
09:37 74%

Coming Back From A Party, Lizzy Makes Me Very Naughty

1 year ago

BeMyHole

shemale, amateur, shemale and girl, party, first time, MILF
15:03 74%

First time sucking dick? And swallowing my hottest patrons

4 months ago

IcePorn

handjob, shemale, blowjob, POV, swallow, first time
10:28 74%

Boy very first time with trans

5 years ago

HDSex

first time, amateur
16:12 74%

Stephie scarlet first time pegging a tgirl

2 years ago

IcePorn

pegging, first time, amateur
39:01 73%

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

3 years ago

xHamster

shemale and girl, first time, bisexual
11:02 73%

Pretty Ebony TRANSSEXUAL YPB In Her Very first Time Humping A Fellows Arse

2 months ago

KeekAss

ebony, amateur, homemade, shemale, small tits, first time
01:28 73%

Casting Guy First Time - Itzelxxx

2 years ago

TXXX

casting, first time
10:36 72%

My First Time With My New Ejaculating Fantasy Dildo

2 years ago

BeMyHole

dildo, redhead, solo, toys, first time, shemale
04:20 72%

Old man partners daughter and tranny first time Alyssa Gets Her Way With

6 years ago

TXXX

old man, first time
06:09 71%

Casting Nubian TS Strokes her Fat Cock

7 years ago

TrannyGem

casting, fat, shaving, first time
07:34 71%

My very first Time in Winston-Salem, NC (TRANSSEXUAL PublicPrincess)

5 years ago

TrannyGem

public, spy, caught, jerking, first time, cum in ass
12:32 71%

Blair Glass first Time With a pulverize Machine

2 years ago

ShemaleMovie

glasses, machine, first time
36:34 71%

First time with my Hismith machine

4 years ago

TrannyOne

machine, first time, stockings
10:15 71%

Free-for-all Dorian Drake gets barebacked for the first-ever time by gigantic shaft from trans female

1 month ago

KeekAss

shemale, blowjob, first time
11:15 71%

Fuck stick in the bum, onanism and jizm first-ever time using a fucktoy, its joy. My femboy booty was highly open

1 year ago

TrannyGem

black, dildo, cumshot, masturbation, celebrity, BBC, first time
25:17 71%

Vivien Valero First Time shelady Strokers ladyboy

6 years ago

ShemaleZ

cumshot, first time, solo
13:16 71%

ADULT TIME - Curious Cis Couple Have Their First Threesome With Trans Baddie Kasey Kei!

3 years ago

TXXX

threesome, couple, first time
10:55 71%

His very first Time Coming to the Gullet Supermarket

6 years ago

TrannyGem

gagging, handjob compilation, cumshot compilation, first time, ebony
16:51 70%

Young Sexy Ladyboy First Time With Her Sugar Stepdaddy Suck Fuck Cum - Sugar Daddy

8 months ago

HClips

shemale fucks guy, asian, amateur, first time, ladyboy
18:14 70%

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

2 months ago

ShemaleMovie

shemale, threesome, monster, stepmom, reality, futanari, first time
01:21 70%

Arab Femboy First Time Anal

5 years ago

AShemaleTube

homemade, arab, first time, femboy, domination
06:10 69%

Dudes very first Time With A t-girl

6 years ago

HDSex

prostitute, first time
15:46 69%

Turning My husband Into Tranny tart, lady first time with Tranny

1 year ago

ShemaleMovie

shemale, strapon, train, BDSM, crossdresser, husband, ass
16:40 69%

Perola Martinez gives it to the guy for the first time

5 months ago

XXXVogue

anal, shemale fucks guy, first time, big cock, amateur, blowjob
05:01 69%

[Trans] My First Time Venus Lux

4 years ago

TrannyOne

feet, heels, first time
07:39 69%

Trap Schoolgirl Anal For The First Time

6 years ago

TrannyOne

first time
51:27 68%

Little ones first time - all 3 angles

5 years ago

TXXX

asian, bareback, first time, amateur
02:51 67%

FIRST TIME real dick ANAL fuck - TATTOO couple vs shy girl - ATM female orgasm, anal GAPE (goth, punk, alt porn)ZF046

9 months ago

Sexu

lesbian, bisexual, couple, orgasm, tattoo, shy, goth
15:26 67%

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

1 year ago

JizzBunker

first time, creampie, shemale and girl
08:10 67%

Milf plumbs teen with wire on very first time Risky Birthday Capers

4 months ago

ShemaleTaxi

teen (18+), MILF, first time
10:57 67%

LEGACY MESS : Filipino Slut With ginormous Cock for the first time in pornography messy Fucks deep hard in the Throat and Ass of her Partner

6 months ago

ShemaleMovie

BDSM, big cock, deepthroat, filipina, slut, first time, shemale fucks guy

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