SHEMALE • FIRST TIME 3,956 videos

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«‹3 4 5 6 7 ›

15:48

This is my very first time crossdressing like this

4 months ago

ShemaleMovie

masturbation, crossdresser, shemale, first time
17:42 17%

I Fuck a Tranny Girl for the First Time 4k

4 months ago

Beeg

first time, shemale, reality
11:02

Transboy unloading for the first time

4 months ago

ShemaleMovie

homemade, orgasm, first time, amateur
03:06

Brand New Trans Cutie Pixie Pond Fucked By A Man For the First Time Ever

4 months ago

AShemaleTube

amateur, small cock, shemale, POV, interracial, small tits, first time
3:05:31 38%

Hiiragi Kana And Alice Nanase In Dass-616 First Time Nh Lesbian Sex. First Time Ever, Ban Lifted. W Exclusive Special Kana Hiiragi

4 months ago

ShemaleZ

lesbian, shemale, stockings, asian, first time
08:06

Yaya (trans) - Having This Rough Sex For The First Time

4 months ago

ShemaleZ

small tits, stockings, nylon
06:00

PLATINUM-BLONDE TRANNY IN CRIMSON UNDERGARMENTS ATTEMPT HEFTY LATINA PENIS FIRST-EVER TIME

4 months ago

TrannyGem

MILF, interracial, missionary
05:29

I nail this trans nymph while she is in the shower

4 months ago

ShemaleMovie

feet, homemade, beauty, shemale, shower, big cock, babe
06:00

Amateur Porn 18-years-old ladyboy first time on cam bareback butt sex

4 months ago

XoZilla

ladyboy, anal, bareback, first time, amateur
12:15

TRANSFIXED - Horny Michael DelRay Has His First Trans experience With splendid acquaintance Jade Venus

4 months ago

ShemaleMovie

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06:15

Curly haired lesbo gets porked by TRANSSEXUAL for first-ever time (Erica Cherry, Queenie Sateen)

4 months ago

KeekAss

first time
04:14

I Tried An Anal Dilator The First Time And Had A Sissygasm (slow-motion Replay)

4 months ago

HClips

masturbation, amateur
07:42

When I Lost My virginity - romp memories by Maya McAdamia

4 months ago

ShemaleMovie

arab, first time, BBW
05:20

Real unexperienced Transgender woman Gets Used As A plaything

4 months ago

ShemaleMovie

ass, femboy, amateur, anal, first time, shemale
15:41

First Time Sex with Strong Man

4 months ago

JizzBunker

babe, asian, shemale, hardcore, first time
09:32

Pretty schoolgirl Shemale girl jacks for the very first time after school

4 months ago

ShemaleMovie

teen (18+), BBW, ladyboy, creampie compilation, compilation, babe, cumshot compilation
08:14

Pretty she-male first-ever time in front of camera

4 months ago

ShemaleMovie

asian, first time
10:20 43%

True Nature pt. 1 - Cross dressing Sissy Man Buttfuck Nailed by Ginormous Knob Futa COUGAR

4 months ago

TrannyGem

femdom, public, teen (18+), creampie, old man, teen anal (18+), 3D
06:34

First Time Fembois with Thayane Beck for TrannyBizzare

4 months ago

ShemaleTaxi

anal, ladyboy, shemale fucks guy, first time
07:25

Fucks Transman For The First Time

4 months ago

xShemaleTube

first time, threesome
06:38

Lovely Tfemale's first-ever time with a girl

4 months ago

ShemaleTaxi

blowjob, shemale and girl
06:07

Brunette teen's very first time with a shemale

4 months ago

ShemaleTaxi

first time
11:49

I was pounded by a trans damsel for the very first time

4 months ago

TrannyGem

anal, shemale, first time, mexican
21:36 81%

Trans Fucking A Straight Boy For The First Time

4 months ago

BeMyHole

amateur, shemale, blowjob, BDSM, redhead, ass licking, reality
08:06

First Time Fembois 3 - Trans N Shemale

4 months ago

ShemaleZ

asian, bareback, first time, ladyboy
07:00

Susie Vicentini in Susie First Time on Camera - DreamTranny

4 months ago

TXXX

shemale, mature
08:44 63%

Trans woman punishes this fellow by destroying his backside

4 months ago

ShemaleMovie

homemade, beauty, BDSM, crossdresser, big cock, babe, heels
05:08 83%

NUBILE GUY GOT RAGING WITH ME DEEP-THROATING HIS TROUSER SNAKE AND ASK ME TO LET HIM PULVERIZE ME

4 months ago

TrannyGem

amateur, teen (18+), creampie, couple, teen anal (18+), 18, babe
10:51 50%

My step-dad CATCHES me drilling my bf

4 months ago

ShemaleMovie

caught, shemale fucks guy, first time, cum in mouth, big cock, facial
02:51

Blondes and psychedelic lovemaking (Part five) Remastered - Toon

4 months ago

TrannyGem

amateur, teen (18+), japanese, cum in mouth, japanese uncensored
05:40

Blondes and psychedelic hook-up (Part four) Remastered - Toon

4 months ago

TrannyGem

amateur, teen (18+), first time
05:40

Blondes and psychedelic fucky-fucky (Part two) Remastered - Cartoon

4 months ago

TrannyGem

amateur, cum in ass
15:03

Giant stiffy arms free-for-all cum shot in underwear and matching rump buttplug

4 months ago

TrannyGem

big ass, orgasm, monster, close up, surprise, first time, hands free
14:45

The ladyboy Kendra Romans getting full of chocolate

4 months ago

ShemaleMovie

first time, amateur, full movie, POV
07:37

Lovens manage on a drill machine, rigid ravaging my culo of a sissy superslut

4 months ago

TrannyGem

first time, anal, sissy, cute, machine, femboy
10:41

MI CLIENTE ME PIDE UN MASAJE CON FINAL FELIZ EN SU BUTT. (2PARTE)

4 months ago

TrannyGem

first time, anal, turkish
02:10

Femboy blowing trunk for the very first time

4 months ago

TrannyGem

first time
10:37

MI CLIENTE ME PIDE UN MASAJE CON FINAL FELIZ EN SU RUMP.

4 months ago

TrannyGem

black, creampie, lesbian, squirt, massage, bondage, BDSM
08:30

Fleshlight cumshots from the back plus assfuck blinking

4 months ago

ShemaleMovie

black, tease, double anal, piercing, creampie compilation, compilation, jerking
06:32 40%

Your very first Time Getting nailed by a Trans dame: First Date GFE POV Femdom

4 months ago

ShemaleMovie

kissing, femdom, shemale, POV, BDSM, girlfriend, filipina
10:21

TRANS ANGELS - Michael sucks Marissa Minxs Dick For The First Time Before He bangs Her bum

4 months ago

ShemaleMovie

big ass, missionary, big cock, first time
05:16

Transsexual goes mad about blowing man-meat of a elegant dude

4 months ago

ShemaleMovie

big ass, first time
06:39

Husband and wifey very first time three-way with shemale

4 months ago

ShemaleTaxi

masturbation, wife, threesome, husband
01:42

First time with tranny

4 months ago

AShemaleTube

stockings, bareback, first time
07:59

Lovely french Femboy demonstrate his super-steamy figure nand used his fucktoy inwards his arse

4 months ago

TrannyGem

femboy, shemale and girl, asian, first time, heels, french
07:17

JUDE LYNX — WARM OMEGA LYNX STUD FROLICKING WITH HIS TAIL

4 months ago

TrannyGem

femboy, futanari, dildo, shemale and girl, anime, first time
14:39 84%

Ride With A Beautiful & Wonderful Tranny Isabella Salvatore

4 months ago

BeMyHole

beauty, public, big tits, car, 18, jerking, riding
12:56

She made me spunk twice! first-ever time pummeling Britney from Tantaly - Emily Adaire

4 months ago

ShemaleMovie

small cock, missionary, amateur, first time, shemale and girl, nylon
05:31

Very first time fisting my sissys ass, he almost took my whole mitt! fendom rectal!

4 months ago

ShemaleMovie

anal, strapon, crossdresser, sissy, fisting
11:17

MY FIRST TIME WITH giant THAI she-creature manstick

4 months ago

ShemaleTaxi

cumshot, cum in mouth
11:17

THE first TIME YOU NEVER leave behind

4 months ago

ShemaleTaxi

teen (18+), big ass, lingerie, ladyboy, 18, ass to mouth, taxi
05:19

Sexy BBC fucks a sumptuous t-girl for the very first time

4 months ago

ShemaleMovie

futanari, big ass, 3D, anime, BBC, cartoon
12:57

ADULT TIME - super kinky Hunk RUINS Ariel Demure Tight Trans Ass With harsh ASSFUCKING!

4 months ago

ShemaleMovie

first time, bareback
26:15

Guy Gets His Ass Fucked for the First Time in a Hotel by Latina Tranny Beatriz

4 months ago

$$ FapHouse

handjob, big cock, shemale fucks guy
06:07

Nervous About My First Time Fucking A Thai Street Trans At Trannybizzare

4 months ago

ShemaleZ

thai, first time, ladyboy
07:17 67%

POINT OF VIEW: Humping a jaw-dropping Trans nymph for the first-ever time

4 months ago

TrannyGem

amateur, cute, POV, spanish, latina, first time
10:14

Real Transgender nymph Gets assfuck screw

4 months ago

ShemaleMovie

amateur, femboy, homemade, first time
05:39

Her Curious Boyfriend Trying Trans Sex For The First Time 6 Min - Haley Spades, Steve Rickz And Petite Blonde

4 months ago

ShemaleZ

boyfriend, small cock, first time
02:07

Id you inwards this super-hot femboy, steamy femboy wants milk in her booty

4 months ago

TrannyGem

big cock, first time, solo, femboy
13:16

Young femboy TrapyAle, plays with her taut bootie using her rump buttplug and a large purple fake penis

4 months ago

TrannyGem

riding, femboy, dildo, first time, penis
02:01

This is my very first time attempting buttfuck fuck-a-thon using a enormous fake penis

4 months ago

TrannyGem

shemale and girl, first time, dildo, solo, amateur, penis
1:18:48

Russiandoll00 sumptuous eventually cumming!!

4 months ago

ShemaleMovie

shemale, beauty
13:25

Steaming Trans Chick Solo Onanism VERY FIRST TIME ON CAMERA!

4 months ago

TrannyGem

small tits, solo
08:15

Slim trans teen Fany Menezes experiments with the machine for her first time

4 months ago

XXXVogue

small tits, first time, solo
11:39

First time porking a StarDust Dragon Amarok from desire Grove!! jiggling CUM!!!

4 months ago

ShemaleMovie

shemale, dildo, first time, huge dildo, machine
10:31 83%

Tranny teenager Cassie yells bootie Fucked & Hair Pulled

4 months ago

ShemaleMovie

amateur, homemade, shemale, creampie, big ass, couple, crossdresser
31:16

Deep Digging With A Bbc In The Big Ass Of Manuela Matias First Time With Ed Chocolate And Big Bbc

4 months ago

ShemaleZ

anal, brazil, tattoo, latina, ass to mouth, ass licking, blonde
04:33

Milking for the firs time after 25 days sans touhing myself. I come in two mins. Noisy wails

4 months ago

TrannyGem

shemale and girl, amateur, italian
20:54

BLONDE ladyboy IN crimson underwear TRY BIG LATINA COCK FIRST TIME

5 months ago

ShemaleMovie

domination, shemale fucks guy, big cock, bareback, ladyboy, first time
04:25

Im your medicine, my arse will heal all your ultra-kinky Wish

5 months ago

TrannyGem

crossdresser, masturbation, dildo, first time, anime
08:00

Korra Del Rio, Bradley Spencer And Spencer Bradley - Beauty Fucks For Her First Time With A Trans And Its

5 months ago

Fuxxx

beauty, first time
04:00

Whats Russian For Suck My Cock? First Time Chick Fucked By Ts Teacher

5 months ago

Fuxxx

nylon, russian, first time, clothed
12:40

First time busty Latina Jesse Pony tries to fuck with shemale babe Kasey Kei

5 months ago

YourLust

small tits, MILF, first time
24:08

First-Ever time dual foray after 25 days sans rubbin myself. I cant get enough! Stoner fav.

5 months ago

TrannyGem

feet, amateur, double penetration, first time
07:45

Guy Is First Time Topped By Shemale Wife

5 months ago

HClips

big ass, wife, first time, threesome
06:39

Huge baps dark-hued TS first time anal

5 months ago

ShemaleTaxi

first time
08:24

First-time girl indulges with a dildo for some solo fun

5 months ago

XXXVogue

stockings, crossdresser, shemale and girl, solo
09:12

Leni gets pounded outdoors for the first time with an internal cumshot

5 months ago

XXXVogue

creampie, outdoor, crossdresser, first time, amateur
51:58

First-time trap enjoys a wide open slot with some hefty toys

5 months ago

XXXVogue

first time, crossdresser
03:19 29%

Studio conversation Tit addicted Lezzies hymecymeyseh vilguinvyhpca Practice first-ever time

5 months ago

TrannyGem

ebony, indian, shemale, lesbian, german, asian, japanese
2:31:51

Danna Valentina 20200828 first-ever time i catch spunk

5 months ago

ShemaleMovie

first time, shemale, caught
03:03

Soy transroxy, una barra de chocolate muy sabrosa para chupar, gran verga morena

5 months ago

TrannyGem

first time, shemale fucks guy, BBC, big ass, ebony
16:02

ADULT TIME Bored Lulu Chu DARED To Get Very first Internal cumshot From T Female Zariah Aura During Strength Outage

5 months ago

KeekAss

first time, cumshot, shemale
03:05 50%

Ravaging after experience

5 months ago

TrannyGem

creampie, shemale, ebony, amateur, hardcore, first time
10:23

Transgender Princess Very First Time Self-Clyster w/Water Bottle; Candid Flatulence & Peeing

5 months ago

TrannyGem

feet, pissing, farting
13:38 14%

FaKings featuring Kate Blacks beautiful women scene

5 months ago

OkXXX

amateur, beauty, black, shemale, spanish, 18, compilation
06:22 75%

Unexperienced ladyboy shemale teenage beau fucked in the ass by a huge white cock

5 months ago

ShemaleMovie

thai, POV, asian, bareback, first time, chinese
06:16 83%

Alluring trap jacking her firm sausage

5 months ago

ShemaleMovie

sissy, femboy, amateur, shemale, jerking, solo
06:25

First-time big-titted shemale Nim gives oral pleasure and takes a hard anal drill

5 months ago

XXXVogue

shemale fucks guy, ladyboy
10:14

Chloe Temple Gets Her Ass And Pussy nailed At The Same Time On Her very first Day At Work With Winter XX woman -Trans Angels

5 months ago

ShemaleMovie

creampie, first time
06:21

Tiny amateur ladyboy trans teen Many POV blowjob and buttfuck hump from behind

5 months ago

ShemaleMovie

thai, amateur, ladyboy, first time
10:27

Jade Venus Is date Her Mother-In-Law For The first Time And Her poon At The Same Time - Trans Angels

5 months ago

ShemaleMovie

bareback, first time
05:17

Sex industry star August Taylor first time ass-fuck humping on cam

5 months ago

ShemaleMovie

teen (18+), first time, teen anal (18+)
05:17

Shelady luvs some messy playing

5 months ago

ShemaleMovie

shemale, big cock, first time
04:45

Trans female very first time toying with candle paraffin wax

5 months ago

TrannyGem

BDSM
08:07

White T-Model gulps her beaus beefstick with her splendid Jaws while getting her Bootie finger-banged

5 months ago

TrannyGem

couple, shemale fucks guy, shemale and girl, ebony, big cock, swallow
13:11

My first time being filmed! Solo playtime taunt

5 months ago

ShemaleMovie

orgasm, first time, solo
13:13

Assfuck Fuck Stick Railing in Hip High Socks

5 months ago

TrannyGem

fetish, first time, socks
21:43 78%

Hot Young Blondie - His First Time

5 months ago

BeMyHole

teen (18+), blowjob, teen anal (18+), dogging, 18, ass licking, domination
05:40

Is Ready To Get Her First Time Fuck By Two 6 Min With Tori Easton, Crystal Thayer And Raven Lane

5 months ago

ShemaleZ

stockings, first time, redhead, MILF, threesome
13:42

Pretty Pinay transgender princess attempts out using a funbag massager pump machine for the very first time

5 months ago

TrannyGem

machine, small tits, solo, amateur, massage, pump
08:06

Guy Fucks Ladyboy In The Ass For The First Time In A Swinger Club

5 months ago

ShemaleZ

shemale fucks guy, big ass, asian, ladyboy, swinger, first time
05:21

Muddy she-creature loses control

5 months ago

ShemaleMovie

ass to mouth, first time, prostitute
05:26 72%

Shy guy learning to suck his Horny Tgirl Veronica Sanders Big Clit til she finishes off on his face

5 months ago

ShemaleTaxi

kissing, black, ladyboy, facial, clit, babe, shy
33:49 88%

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

5 months ago

BeMyHole

amateur, public, anal, big ass, car, latina, ass licking
15:28

Kenzie Taylor First Time With T-Girl Brittney Kade!

5 months ago

BeMyHole

shemale, big tits, dogging, ass licking, shemale and girl, deepthroat, domination
05:38

Beautiful legitimate year old teen virgin gal riding on a weenie for the first time

5 months ago

ShemaleMovie

couple, teen anal (18+), dildo, riding, big cock, babe, ass
06:38

I sucked a transsexual hard-on for the very first time

5 months ago

ShemaleTaxi

first time
07:10

Old stud and teenager pokes sugar daddy first time Tender Sex in

5 months ago

ShemaleMovie

old and young (18+), first time, teen (18+)
06:16

Spex femboy sweetheart Brooklyn Roberts solo

5 months ago

ShemaleMovie

first time, solo, femboy, big cock, masturbation
08:04

Extended Cut of My Fat Trans Ass Gets Fucked by a Black Cock for the First Time.

5 months ago

AShemaleTube

black
05:05

Tearing Up myself with a humungous fake penis for the very first time and spunking - myLanaSky

5 months ago

AShemaleTube

first time, crossdresser, sissy, femboy
15:11

Thai doll taste huge shemale spunk-pump first time

5 months ago

ShemaleMovie

thai, shemale, asian, pump
05:36

Maduro me coge súper duro

5 months ago

TrannyGem

first time, massage
30:12

Sequel to Pegging of Sissy fuckslut for the first Time

5 months ago

ShemaleMovie

handjob, shower, toys, bathroom, pegging, sissy, first time
06:30

She-males first time with ebony boy

5 months ago

ShemaleTaxi

first time, cuckold, hardcore
05:01

First time in a fufu clip my useless worthless clitty

5 months ago

AShemaleTube

amateur, sissy, femboy, solo
05:13

Hot 18 year old young man tries his hottest friends cock for the first-ever time when there is no one in his mansion

5 months ago

ShemaleMovie

teen (18+), big cock, old man, first time
05:24

Gargle Her Meatpipe - Tgirl Manstick Fellating Encouragement - Imposed Bisexous

5 months ago

TrannyGem

handjob, cute, femdom, bisexual, fetish, cuckold, shemale and girl
14:03

My very first time as a crossdressing sissy was liberating

5 months ago

ShemaleMovie

sissy, crossdresser

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