First Time Videos - Trans (24,228)

Straight Young Best Friends Try Anal Sex For The First Time 4K

Straight Young Best Friends Try Anal Sex For The First Time 4K

LoveTranSex 1 year ago

His First Time with a Trans, I Think He Got Addicted to My Mouth and My Ass

His First Time with a Trans, I Think He Got Addicted to My Mouth and My Ass

xHamster 1 year ago

Twink gets a good fuck from a straight friend with a big dick - 503

Twink gets a good fuck from a straight friend with a big dick - 503

xHamster 2 years ago

Hot cum compilations July 2025 , sissy femboy vs daddy

Hot cum compilations July 2025 , sissy femboy vs daddy

xHamster 4 days ago

Kendal Penny has anal fun in college

Kendal Penny has anal fun in college

Tranny.one 3 years ago

Cruising Stupid Gay Gets Fucked Bareback by Straight Countryman Cums Inside His Tight Gay Ass

Cruising Stupid Gay Gets Fucked Bareback by Straight Countryman Cums Inside His Tight Gay Ass

xHamster 5 months ago

Shemale teen first time bareback

Shemale teen first time bareback

aShemaleTube 7 years ago

First time swinging with a trans, what a blast

First time swinging with a trans, what a blast

Katestube 2 years ago

First-Time Bareback Amateur Crossdresser

First-Time Bareback Amateur Crossdresser

Eporner 5 months ago

Beautiful shemale pounds the guy's ass bareback for the first time

Beautiful shemale pounds the guy's ass bareback for the first time

Tranny.one 3 years ago

Teen Femboi Fucked For The 1st Time

Teen Femboi Fucked For The 1st Time

Tranny.one 5 years ago

I Lost a Bet with a Straight Soccer Player Friend and He Fucked Me Until He Cums Inside My Ass

I Lost a Bet with a Straight Soccer Player Friend and He Fucked Me Until He Cums Inside My Ass

xHamster 5 months ago

Petite Teen's First Time With A Hot Milf - PetitesVision

Petite Teen's First Time With A Hot Milf - PetitesVision

Hoes.tube 3 weeks ago

Gay Porn In Cross-dressing Hiromi Aizawa 4 Times Embraced By An Energetic Young Man.ver2 First Times 12 Min

Gay Porn In Cross-dressing Hiromi Aizawa 4 Times Embraced By An Energetic Young Man.ver2 First Times 12 Min

AbGay 5 months ago

Hot brunette shemale anal fucks dude for the first time in his life

Hot brunette shemale anal fucks dude for the first time in his life

TransVibe 11 months ago

Fucking the ass of a young gay twink who barely turned 18

Fucking the ass of a young gay twink who barely turned 18

xHamster 1 year ago

Crossdressers First Time 2

Crossdressers First Time 2

GayCK 2 years ago

Vivian Flashes A Very first Timer A dear Time

Vivian Flashes A Very first Timer A dear Time

TransTube.tv 1 month ago

Fucking our virgin viewer, his first time with another guy

Fucking our virgin viewer, his first time with another guy

xHamster 2 years ago

Kendra Romans - First Time

Kendra Romans - First Time

Eporner 2 years ago

Very First time for my hubby ravage with She-Male

Very First time for my hubby ravage with She-Male

TrannyGem 2 months ago

First-ever Time With A

First-ever Time With A

TransTube.tv 3 months ago

I picked up a fucking femboy sucker on the side of the road to fuck his holes.

I picked up a fucking femboy sucker on the side of the road to fuck his holes.

BoyFriendTV 1 month ago

Shemale fucks husband and wife in a sexy anal threesome

Shemale fucks husband and wife in a sexy anal threesome

4KPorn 1 year ago

Cumshot from tranny's huge cock

Cumshot from tranny's huge cock

xHamster 2 years ago

His first time - no virgin anymore 3

His first time - no virgin anymore 3

GayCK 4 years ago

Topping a guy friend for the first time!!!

Topping a guy friend for the first time!!!

Tranny.one 4 years ago

Yasmin Lee, Ranger

Yasmin Lee, Ranger

xHamster 3 months ago

First time in the Ass iwant a doggy style!

First time in the Ass iwant a doggy style!

aShemaleTube 1 year ago

You will never forget your first time with shemale babe Mel

You will never forget your first time with shemale babe Mel

xHamster 9 years ago

Bisexual guy looses anal virginity with tattooed tranny TS Foxxy

Bisexual guy looses anal virginity with tattooed tranny TS Foxxy

AnySex 5 years ago

First time I stripped and put my cock in the guy's ass. Cruise twink with a big cock

First time I stripped and put my cock in the guy's ass. Cruise twink with a big cock

xHamster 3 weeks ago

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

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

Tranny.one 2 years ago

My first time with a real transsexual...

My first time with a real transsexual...

xHamster 1 year ago

Sexy College Blonde Gets Tight Ass Fucked for the first Time

Sexy College Blonde Gets Tight Ass Fucked for the first Time

Eporner 3 years ago

Twink Has his Very First Time With Highly mouth-watering TRANSSEXUAL

Twink Has his Very First Time With Highly mouth-watering TRANSSEXUAL

TrannyGem 4 years ago

First Time Amateur

First Time Amateur

aShemaleTube 12 years ago

Boy becomes a MAN by banging hot shemale Nicky Bermudez!

Boy becomes a MAN by banging hot shemale Nicky Bermudez!

xHamster 1 year ago

Cutiepii33quinn gets her cherry arse nailed for very first time

Cutiepii33quinn gets her cherry arse nailed for very first time

TrannyGem 3 years ago

"Step-Dad's Creepy Fantasy - Step Daughters First Time Anal Sex"

"Step-Dad's Creepy Fantasy - Step Daughters First Time Anal Sex"

4KPorn 1 month ago

The almost all glamorous t-girl in Argentina gets into the car and gets up to mischief on the streets of Buenos Aires - Argentina - Babyjazmin

The almost all glamorous t-girl in Argentina gets into the car and gets up to mischief on the streets of Buenos Aires - Argentina - Babyjazmin

SortPorn 2 weeks ago

SHEMALE Nicky Bermudez wants a young guy to fuck her ass - FAKings

SHEMALE Nicky Bermudez wants a young guy to fuck her ass - FAKings

aShemaleTube 1 month ago

I Lost a Bet with a Gay-for-pay Soccer Player Mate and He Romped Me Until He Spunks Inwards My Booty

I Lost a Bet with a Gay-for-pay Soccer Player Mate and He Romped Me Until He Spunks Inwards My Booty

4Gay 2 months ago

The first time with a tranny

The first time with a tranny

TransVibe 11 months ago

First time with a

First time with a

BeMyHole 4 years ago

Crimson-sizzling Tatt guy makes spunky love to an Asian Trans chick (Utter Version)

Crimson-sizzling Tatt guy makes spunky love to an Asian Trans chick (Utter Version)

TransTube.tv 10 months ago

Milky Sissy Femboy eats cum with her narrow smooth ass from daddy!

Milky Sissy Femboy eats cum with her narrow smooth ass from daddy!

xHamster 3 months ago

Vivian Showcases A Very first Timer A dear Time

Vivian Showcases A Very first Timer A dear Time

Transvids.tv 5 months ago

Shy Trans Femboy Loses Virginity

51% 0:17 / 9:17

Shy Trans Femboy Loses Virginity

Clips4sale 8 months ago

My Crossdresser Stepsister Tight Ass

My Crossdresser Stepsister Tight Ass

SissyFlix 8 months ago

No condom Gay-for-pay dude very first time bottom for Jade Jameson FINEST. ???? FLICK I have MADE

No condom Gay-for-pay dude very first time bottom for Jade Jameson FINEST. ???? FLICK I have MADE

TransTube.tv 2 months ago

First time for my husband fuck with Ladyboy Full (Free Video)

First time for my husband fuck with Ladyboy Full (Free Video)

Lesbian8 1 month ago

Sheboy pleasing a boy

Sheboy pleasing a boy

Eporner 3 years ago

Package Delivery

Package Delivery

PornHeal 1 year ago

THIS WAS THE FIRST TIME I HAD SEX WITH THIS GUY WHO MADE ME FEEL TOO SENSUAL EVERY TIME HE PENETRATED ME UNTIL I WAS FULL

THIS WAS THE FIRST TIME I HAD SEX WITH THIS GUY WHO MADE ME FEEL TOO SENSUAL EVERY TIME HE PENETRATED ME UNTIL I WAS FULL

xHamster 4 months ago

Young german amateur transexual teen shemale fucks first time anal with huge cock

Young german amateur transexual teen shemale fucks first time anal with huge cock

Tranny.one 2 years ago

on the of a young guy

on the of a young guy

xHamster 1 year ago

This Guy Asked Me to Give Him the Best Oral Sex He's Ever Felt so Far While He Trembled with Pleasure Finishing

This Guy Asked Me to Give Him the Best Oral Sex He's Ever Felt so Far While He Trembled with Pleasure Finishing

xHamster 3 months ago

Hot shemale fucks for first time her boyfriend

Hot shemale fucks for first time her boyfriend

Tranny.one 3 years ago

heterosexual dude bangs BB and jism on femboy ass*full vid on OF*

heterosexual dude bangs BB and jism on femboy ass*full vid on OF*

GayCK 2 years ago

Trans - First-Time Fantasy

Trans - First-Time Fantasy

TransVibe 11 months ago

Sergio very first time romp

Sergio very first time romp

GayCK 2 years ago

Hotwife Nichole meets her big black cock bull for the first time

Hotwife Nichole meets her big black cock bull for the first time

4KPorn 3 years ago

Bretts Frist Trans Female fuck - 53 min

56% HD 0:48 / 53:34

Bretts Frist Trans Female fuck - 53 min

DarkCruising 3 years ago

My Very first Time Assfucking

My Very first Time Assfucking

Transvids.tv 1 month ago

Virgin Tom´s 1st Time

60% HD 0:39 / 10:09

Virgin Tom´s 1st Time

FapHouse 7 months ago

Wow Straight Friend big monster cock I touch first time

Wow Straight Friend big monster cock I touch first time

xHamster 1 year ago

Hot Young Blondie - His First Time

Hot Young Blondie - His First Time

BeMyHole 3 weeks ago

TS Dominance: Initiation of First Time Subs

TS Dominance: Initiation of First Time Subs

Tranny.one 1 year ago

Crossdressers First Time

Crossdressers First Time

CrazyPorn 2 years ago

Very first time hetero with trans glory

Very first time hetero with trans glory

TransTube.tv 2 months ago

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

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

xHamster 1 year ago

Hottest virgin ass ever

Hottest virgin ass ever

xHamster 7 months ago

Sucking Off Str8 guy in parking lot. It was his first time

Sucking Off Str8 guy in parking lot. It was his first time

AbTranny 6 years ago

Mature guy tries a stunning trans shaft while his friend films

Mature guy tries a stunning trans shaft while his friend films

Sheshaft 10 months ago

Gay-For-Pay Cowboy Deep-Throats Trans Dinky for Very First Time

Gay-For-Pay Cowboy Deep-Throats Trans Dinky for Very First Time

TrannyGem 2 years ago

His First Time Ever

65% HD 1:01 / 8:57

His First Time Ever

FapHouse 1 year ago

First Time Fembois Thai trans

First Time Fembois Thai trans

Eporner 5 months ago

I finally fucked my straight friend after completely naked massage

I finally fucked my straight friend after completely naked massage

AnySex 2 years ago

Trans fuckin' a hetero dude for the very first time

Trans fuckin' a hetero dude for the very first time

TransTube.tv 2 months ago

T-Girl and twunks homo sexundressing first-ever time These 2 begin things off with some

T-Girl and twunks homo sexundressing first-ever time These 2 begin things off with some

GayCK 6 years ago

Lanita tops boyfriend for the first time while live

Lanita tops boyfriend for the first time while live

aShemaleTube 5 years ago

ts4straight fucks straight blonde virgin bodybuilder

ts4straight fucks straight blonde virgin bodybuilder

PornOne 8 months ago

Young Virgin`s Cherry Popped After Years: Unforgettable First Time

Young Virgin`s Cherry Popped After Years: Unforgettable First Time

XXXShemalePorn 4 years ago

Shemale teen with big cock lets guy fuck her in the ass

Shemale teen with big cock lets guy fuck her in the ass

xHamster 2 years ago

So It's Your First Time With A Trans Woman

So It's Your First Time With A Trans Woman

Eporner 1 year ago

White Dude Doesn't Know If He Can Handle Big Black Dick

White Dude Doesn't Know If He Can Handle Big Black Dick

AllBoner 3 years ago

shelady Very First Time cam

shelady Very First Time cam

TrannyGem 4 years ago

1st time for my spouse screw with Ladyboy Full (Free Movie)

1st time for my spouse screw with Ladyboy Full (Free Movie)

SortPorn 1 month ago

Young Guy fuck the first Time a Shemale

Young Guy fuck the first Time a Shemale

xHamster 1 year ago

HIS FIRST TIME FUCKED BY A LADYBOY AND HE CUM

HIS FIRST TIME FUCKED BY A LADYBOY AND HE CUM

Tranny.one 4 years ago

Amazing Roxxie Moth Gets Anal Bareback First Time

Amazing Roxxie Moth Gets Anal Bareback First Time

BeMyHole 4 years ago

Male's First Time With Transgender

Male's First Time With Transgender

TransHero 4 years ago

Heterosexual firt time with trans

Heterosexual firt time with trans

TransTube.tv 11 months ago

I Put a Red Blindfold on Markus and Suck His Hard Cock

I Put a Red Blindfold on Markus and Suck His Hard Cock

xHamster 5 months ago

penetrating deep first time in the butthole of newbie asian babe kittila

penetrating deep first time in the butthole of newbie asian babe kittila

PornOne 2 years ago

Guy tries barebacking first time with shemale

Guy tries barebacking first time with shemale

aShemaleTube 5 years ago

First time with a

First time with a

Tranny.one 4 years ago

I fuck a tranny girl for the first time 4k

I fuck a tranny girl for the first time 4k

TransTube.tv 4 years ago

Big Dick Ginger Tgirl eats his ass and begs to be covered in cum

57% 0:35 / 12:40

Big Dick Ginger Tgirl eats his ass and begs to be covered in cum

Clips4sale 3 months ago

First casting for the real married lovers

First casting for the real married lovers

Hoes.tube 7 months ago

Witness me pulverize my bf firm and make him spunk

Witness me pulverize my bf firm and make him spunk

TransTube.tv 2 months ago

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

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

aShemaleTube 6 months ago

Shemale fucked guy for the first time and she enjoyed hardcore anal sex

Shemale fucked guy for the first time and she enjoyed hardcore anal sex

aShemaleTube 1 year ago

Barely having reached 18 years of age, for the first time rough sex with moans and screams until cum!

Barely having reached 18 years of age, for the first time rough sex with moans and screams until cum!

xHamster 6 months ago

Belle Adams First Time Topping

Belle Adams First Time Topping

YepTube 1 year ago

Hot shemale take Boys ass and fuck him like a Sissy

Hot shemale take Boys ass and fuck him like a Sissy

Tranny.one 4 years ago

1st time for my spouse bang with Ladyboy Full (Free Clip)

1st time for my spouse bang with Ladyboy Full (Free Clip)

BigTitsLust 1 month ago

Sissy feels cum inside her for the first time

Sissy feels cum inside her for the first time

xHamster 3 years ago

First time

aShemaleTube 2 years ago

Fucks Her Male Friend For The First Time - Danni Daniels

Fucks Her Male Friend For The First Time - Danni Daniels

getTranny 3 years ago

Beautiful shemale pounds the guy's ass bareback for the first time

Beautiful shemale pounds the guy's ass bareback for the first time

BeMyHole 5 years ago

We Met for The First Time with This Married Handsome Man and We Both Went Beyond Borders

We Met for The First Time with This Married Handsome Man and We Both Went Beyond Borders

xHamster 2 years ago

Big pecker tranny anal fuck alt dude

Big pecker tranny anal fuck alt dude

Sheshaft 5 years ago

STRAIGHT MALE LIKES TO FUCK ME WHEN I WEAR HIS GIRLFRIEND'S STOCKINGS

STRAIGHT MALE LIKES TO FUCK ME WHEN I WEAR HIS GIRLFRIEND'S STOCKINGS

xHamster 1 year ago

Amazing young student gets her first anal cummed

Amazing young student gets her first anal cummed

Hoes.tube 3 years ago

DEVILS TGIRLS - Gorgeous Trans Lena Moon Tries Swinger Fuck For The First Time

DEVILS TGIRLS - Gorgeous Trans Lena Moon Tries Swinger Fuck For The First Time

aShemaleTube 1 year ago

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

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

TrannyGem 1 year ago

First Time With A Shemale

First Time With A Shemale

BeMyHole 4 years ago

Assfucking of curious hetero attracted by a big Brazilian cock, his orgasm squeezes my cock and makes me cum

Assfucking of curious hetero attracted by a big Brazilian cock, his orgasm squeezes my cock and makes me cum

xHamster 1 year ago

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