First Time Anal Videos - Trans (25,069)

Body stocking sissy Crossdresser shows off her slutty side in this amateur POV pornstar TS hot video

Body stocking sissy Crossdresser shows off her slutty side in this amateur POV pornstar TS hot video

XHamster 1 week ago

Pretty Girl Strips And Plays In Hotel Room

Pretty Girl Strips And Plays In Hotel Room

Tranny.one 3 years ago

TranssexualVenus.com - Inked gay's first time passionately plowed by Asian trans

TranssexualVenus.com - Inked gay's first time passionately plowed by Asian trans

UrGayPorn 17 hours ago

Beauty in the Eyes of Beholder

Beauty in the Eyes of Beholder

XHamster 3 months ago

Your 1st Trans Tgirl Experience JOI Blonde Russian-Ukranian

Your 1st Trans Tgirl Experience JOI Blonde Russian-Ukranian

Pornzona 3 weeks ago

Beauty in the Eyes of Beholder

Beauty in the Eyes of Beholder

XHamster 1 month ago

Hazelnut Latte: Sissy Co-worker Loosing Virginity and Got Introduced to Juicy Cock for the First Time - Episode 8

57% HD 1:01 / 37:09

Hazelnut Latte: Sissy Co-worker Loosing Virginity and Got Introduced to Juicy Cock for the First Time - Episode 8

FapHouse 6 months ago

Virgin Finn Gets It Really Hard

HD 1:01 / 13:18

Virgin Finn Gets It Really Hard

FapHouse 1 year ago

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

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

AShemaleTube 5 months ago

Seeing My Latina Maid Half Naked Cleaning Ends with Her Fucking Me

Seeing My Latina Maid Half Naked Cleaning Ends with Her Fucking Me

XHamster 1 month ago

Young cock from dropped balls grows the cock quickly.

Young cock from dropped balls grows the cock quickly.

XHamster 1 year ago

Small cock tiny tits Asian femboy teen first time raw anal fuck

Small cock tiny tits Asian femboy teen first time raw anal fuck

Pervclips 1 month ago

Gfe First Machine Fuck

Gfe First Machine Fuck

XHamster 1 year ago

TS Fuck My Pussy

TS Fuck My Pussy

XHamster 3 months ago

My first time with a woman, what a delight, sex without a condom!

My first time with a woman, what a delight, sex without a condom!

AShemaleTube 1 month ago

French kiss

Some.Porn 1 year ago

19 Years Old, Freshly Transitioned....looking for Trouble

57% 1:01 / 16:52

19 Years Old, Freshly Transitioned....looking for Trouble

FapHouse 2 weeks ago

Petite Hairy Sia Wood Takes Every Inch of Trans Monique

64% 0:39 / 32:34

Petite Hairy Sia Wood Takes Every Inch of Trans Monique

FapHouse 1 month ago

Rimming Her as She Screams

Rimming Her as She Screams

XHamster 4 months ago

FEMBOY USES ASS-PLUG FOR FIRST-EVER TIME ! FINISHES WITH MONEY-SHOT !

FEMBOY USES ASS-PLUG FOR FIRST-EVER TIME ! FINISHES WITH MONEY-SHOT !

GayCK 5 years ago

Amara Romani eats creampie from huge tits PAWG Eden Adams pussy – Squirting Guru

60% HD 0:39 / 47:34

Amara Romani eats creampie from huge tits PAWG Eden Adams pussy – Squirting Guru

FapHouse 4 years ago

VERY FIRST TIME TRANSGENDER PLOWED IN BOOTY AND CREAMPIED

VERY FIRST TIME TRANSGENDER PLOWED IN BOOTY AND CREAMPIED

KeekAss 3 years ago

twinks Georgio And Louis raw bang

twinks Georgio And Louis raw bang

GayJaVu 9 months ago

Royal Gathering: the Queen Takes Center Stage

Royal Gathering: the Queen Takes Center Stage

XHamster 2 weeks ago

”Olivia Jay & Kasey Kei Can't Wait Any Longer to Reunite in a Passionate Encounter”

”Olivia Jay & Kasey Kei Can't Wait Any Longer to Reunite in a Passionate Encounter”

IFuckedYourGF 2 days ago

Curvy Trans Goddess with Perfect Huge Tits: Boob Worship, Ass Licking, Hard Pounding & Massive Cumshot in Mouth

Curvy Trans Goddess with Perfect Huge Tits: Boob Worship, Ass Licking, Hard Pounding & Massive Cumshot in Mouth

XHamster 2 months ago

Its the first time you show me your cock

Its the first time you show me your cock

PornGem 1 month ago

I Let My Wife While Banging Her TS Friend

I Let My Wife While Banging Her TS Friend

BeMyHole 2 months ago

Jessica Fappit Fucks Like a Bunny!

66% HD 1:01 / 49:05

Jessica Fappit Fucks Like a Bunny!

FapHouse 1 month ago

Big Cock

XHamster 1 month ago

Amateur crossdresser goes wild and takes a hard pounding on his first time bareback!

Amateur crossdresser goes wild and takes a hard pounding on his first time bareback!

GayX 1 month ago

The Twink got lost in the ruins. Watcher stepdaddy fucked my ass without a condom to cum.

The Twink got lost in the ruins. Watcher stepdaddy fucked my ass without a condom to cum.

XHamster 1 year ago

Black and beautiful professor teaches you how to please her

Black and beautiful professor teaches you how to please her

XHamster 4 months ago

”TGIRLSHOOKUP - America's Sluttiest Hole”

”TGIRLSHOOKUP - America's Sluttiest Hole”

Zatube 4 days ago

Tiny Tit Latina Sucks Cock Then Pegs His Ass Hard

Tiny Tit Latina Sucks Cock Then Pegs His Ass Hard

FapHouse 2 months ago

All Natural Beauties Nico Love & Claire Gemini in First Time Trans Threesome

57% HD 1:01 / 35:17

All Natural Beauties Nico Love & Claire Gemini in First Time Trans Threesome

FapHouse 2 months ago

Jason and Jessy Dubai 13 Bareback!

Jason and Jessy Dubai 13 Bareback!

XHamster 1 month ago

Stepdad Fucking Stepson Bareback

Stepdad Fucking Stepson Bareback

XHamster 1 year ago

Slim Hot Ladyboy Spreads Her Legs Wide For My Cock

Slim Hot Ladyboy Spreads Her Legs Wide For My Cock

BeMyHole 3 months ago

Our Very first Hook-up Gauze- enchanting

Our Very first Hook-up Gauze- enchanting

GayJack 1 week ago

TGIRLS PORN - A Day At The Pond With Holly and Pixie

TGIRLS PORN - A Day At The Pond With Holly and Pixie

XHamster 3 months ago

Bya Lessa Fucking Hard Old Guy

Bya Lessa Fucking Hard Old Guy

XHamster 3 months ago

Risky public sex str8 boys 1st time with a transgender beauty Sex On the Beach

Risky public sex str8 boys 1st time with a transgender beauty Sex On the Beach

ShemaleSin 8 months ago

First time working out with new gym buddy - Emily Adaire fucks new Tantaly sex doll

First time working out with new gym buddy - Emily Adaire fucks new Tantaly sex doll

XHamster 1 year ago

ChaosMen: Natural caucasian scout goes for nailing

ChaosMen: Natural caucasian scout goes for nailing

GaysTubes 3 years ago

Femboy Gets Bred by Savino Black

Femboy Gets Bred by Savino Black

XHamster 6 months ago

The Taste and Smell of Honey When My Favorite Shemale Eats Me

57% HD 1:01 / 9:06

The Taste and Smell of Honey When My Favorite Shemale Eats Me

FapHouse 1 month ago

”Picnic My Butt - Angellica Good, Only Matt”

”Picnic My Butt - Angellica Good, Only Matt”

Rainblow 1 year ago

Avengers Black widow futa babe blowjob and dildo riding fuck Ai Generated 1 Clip 2

Avengers Black widow futa babe blowjob and dildo riding fuck Ai Generated 1 Clip 2

XHamster 1 month ago

Horny Trans Receives Two Cocks in Her Delicious Ass

HD 1:01 / 40:41

Horny Trans Receives Two Cocks in Her Delicious Ass

FapHouse 2 years ago

The First Time Is Always Intense

The First Time Is Always Intense

XHamster 9 months ago

Early Footage of Hot TS Pornstar Lena Kelly

55% HD 1:01 / 33:56

Early Footage of Hot TS Pornstar Lena Kelly

FapHouse 1 month ago

Lap Dance & Anal With Tgirl Stripper ABRIDGED

Lap Dance & Anal With Tgirl Stripper ABRIDGED

PornFreeNow 8 months ago

Hentai Babe futa Orc Big monster hotel sex - Ai Generated

Hentai Babe futa Orc Big monster hotel sex - Ai Generated

XHamster 4 months ago

This Soiree Got Out of Manage..the Bottom Bootie Fuck-hole Got Wrecked

This Soiree Got Out of Manage..the Bottom Bootie Fuck-hole Got Wrecked

MenGem 6 days ago

Buck Richards takes on TS Jexxxica Blake's massive BBC

Buck Richards takes on TS Jexxxica Blake's massive BBC

Fapnado 3 years ago

Having Nasty Freaky Time with My Gay Boy

68% HD 0:39 / 48:45

Having Nasty Freaky Time with My Gay Boy

FapHouse 5 months ago

AI Generated Storm Tranny Babe rides enemy monster cock

AI Generated Storm Tranny Babe rides enemy monster cock

XHamster 5 months ago

Dangerous and Hot Redhead, with Huge Ass and 12 Inch Cock

HD 1:01 / 24:46

Dangerous and Hot Redhead, with Huge Ass and 12 Inch Cock

FapHouse 1 month ago

Black Adventures 102

55% HD 0:39 / 3:09

Black Adventures 102

FapHouse 1 year ago

Erect Penis in a Nice White Ass, Hot Sex

61% 1:01 / 23:43

Erect Penis in a Nice White Ass, Hot Sex

FapHouse 4 months ago

Indian Virgin dude's Very First rock hard fuck-a-thon

Indian Virgin dude's Very First rock hard fuck-a-thon

MenGem 2 years ago

Pretty tranny fucks a woman in the pussy for the first time

Pretty tranny fucks a woman in the pussy for the first time

DrTuber 1 month ago

Ts Jade Venus gives Chanel Noir 1st anal

Ts Jade Venus gives Chanel Noir 1st anal

FetishShrine 4 years ago

”GROOBYVR: Smile! It's Shiri!”

”GROOBYVR: Smile! It's Shiri!”

TransHero 2 years ago

I Hired a Transvestite to Come to My House to Fuck and I Cummed in His Delicious Gay Ass. Creampie

I Hired a Transvestite to Come to My House to Fuck and I Cummed in His Delicious Gay Ass. Creampie

FapHouse 4 months ago

PREMIUM LATINA GROUP SEX!!

PREMIUM LATINA GROUP SEX!!

XHamster 1 year ago

First time for Kittala: Big Cocks, Double Penetration, and Anal Gangbang with DAP!

First time for Kittala: Big Cocks, Double Penetration, and Anal Gangbang with DAP!

TrannyMovs 7 months ago

Ali Da Reaper Fucks ZAZA ZARIAA

Ali Da Reaper Fucks ZAZA ZARIAA

XHamster 1 year ago

Anal Bareback Sex Triple Ejaculation Creampie Big Knob Daddy Hoss Kado Fucking Sexy Trans Hotty Redhead Tori Easton Hardcore Rough

Anal Bareback Sex Triple Ejaculation Creampie Big Knob Daddy Hoss Kado Fucking Sexy Trans Hotty Redhead Tori Easton Hardcore Rough

Dafreeporn 3 months ago

My hairy hole is being fucked by daddy until I cum in my ass!

My hairy hole is being fucked by daddy until I cum in my ass!

XHamster 2 years ago

This guy penetrated me so well and made me orgasm while telling me all the sexual desires he had

This guy penetrated me so well and made me orgasm while telling me all the sexual desires he had

AShemaleTube 3 months ago

Foxxy Seduces the Help

HD 0:39 / 37:26

Foxxy Seduces the Help

FapHouse 1 day ago

Pays The Bills

Some.Porn 5 months ago

Smalltitted petite asian babe cockriding

Smalltitted petite asian babe cockriding

Some.Porn 6 months ago

Straight Mistaken Got Penetrated at Orgy Party

HD 1:01 / 36:56

Straight Mistaken Got Penetrated at Orgy Party

FapHouse 4 months ago

Trans Vanessa Jhons Welcome Rock-hard-core Very first Time Double arse

Trans Vanessa Jhons Welcome Rock-hard-core Very first Time Double arse

Transvids.tv 1 year ago

Beautiful Shemale Hard Group Fuck

57% 1:01 / 4:00:00+

Beautiful Shemale Hard Group Fuck

FapHouse 5 months ago

FIRST-EVER TIME PEGGING! wazoo plumbing, Pegging, And Guts Fapping

FIRST-EVER TIME PEGGING! wazoo plumbing, Pegging, And Guts Fapping

Transvids.tv 9 months ago

German crossdresser get bareback anal fuck

German crossdresser get bareback anal fuck

XHamster 3 years ago

GORGEOUS BRUNETTE WITH WET PUSSY TASTE SHEMALE COCK FIRST TIME

GORGEOUS BRUNETTE WITH WET PUSSY TASTE SHEMALE COCK FIRST TIME

XHamster 3 years ago

Young femboy with hormone- Breasts tits gets fucked for the first time in a pink nightgown

Young femboy with hormone- Breasts tits gets fucked for the first time in a pink nightgown

XHamster 1 month ago

Blonde Femboy French Maid Gets Destroyed Doggy Style in Kitchen - Raw Anal Fuck

Blonde Femboy French Maid Gets Destroyed Doggy Style in Kitchen - Raw Anal Fuck

XHamster 2 months ago

Nikatsu ventures out for the first time practicing Dogging on the streets

Premium HD 31:08

Nikatsu ventures out for the first time practicing Dogging on the streets

XVideosRed 5 months ago

My Stepmom Busts Me Jerkin' It in the Living Room

My Stepmom Busts Me Jerkin' It in the Living Room

Jizzberry 1 year ago

Midnight Pizza

50% HD 1:01 / 23:44

FapHouse 4 months ago

Gorgeous Nerdy Trans Girl Gets Hard Fucking!

Gorgeous Nerdy Trans Girl Gets Hard Fucking!

XHamster 5 months ago

Punjabi Driver Big Cock First Time I Hold in My Hand

61% HD 0:39 / 5:29

Punjabi Driver Big Cock First Time I Hold in My Hand

FapHouse 4 months ago

Sissyslave Swrving Me Rimjob Facesitting Special

Sissyslave Swrving Me Rimjob Facesitting Special

XHamster 1 month ago

Straight Latino Boy Fucked Raw by Latina Trans with Big Dick

HD 0:39 / 32:21

Straight Latino Boy Fucked Raw by Latina Trans with Big Dick

FapHouse 1 month ago

Outside My House Making Love

65% HD 0:39 / 8:16

Outside My House Making Love

FapHouse 2 weeks ago

My Friend Lets His Ass Be Fucked. Extreme Anal Sex with the Trans Dalmita Castellanos and the Teen Angelica Cristal in Fakings

62% HD 1:01 / 38:48

My Friend Lets His Ass Be Fucked. Extreme Anal Sex with the Trans Dalmita Castellanos and the Teen Angelica Cristal in Fakings

FapHouse 4 months ago

Hooked up with Dani Synclair After Meeting on Feeld

Hooked up with Dani Synclair After Meeting on Feeld

XHamster 2 months ago

French tgirl : his first time with a sexy dicky girl

French tgirl : his first time with a sexy dicky girl

Tranny.one 4 years ago

A Helping Hand for a Student with a Big Dick in Public-everyone Can See It, Lots of Cum!

HD 1:01 / 10:51

A Helping Hand for a Student with a Big Dick in Public-everyone Can See It, Lots of Cum!

FapHouse 2 weeks ago

Ai Generated Huge Boobs Trans Sucking Massive Dick While Cum Hard

Ai Generated Huge Boobs Trans Sucking Massive Dick While Cum Hard

FapHouse 4 months ago

The Night Bruce Knight and Eros Finally Linked up Clip 1

The Night Bruce Knight and Eros Finally Linked up Clip 1

XHamster 3 weeks ago

silver-towheaded ladyman acquires protection-free-for-all BIG BLACK COCK For The First-ever-ever Time

silver-towheaded ladyman acquires protection-free-for-all BIG BLACK COCK For The First-ever-ever Time

TransTube.tv 1 year ago

Bucked up - Audrey and Melanie Do a Cam Show!

56% HD 0:39 / 9:25

Bucked up - Audrey and Melanie Do a Cam Show!

FapHouse 2 years ago

Part 2 Amateur Sissy Crossdresser try's to squirt on dildo for Daddy and talks about him paying $8k for her breast implants

Part 2 Amateur Sissy Crossdresser try's to squirt on dildo for Daddy and talks about him paying $8k for her breast implants

XHamster 4 weeks ago

Orgy in Only in the Ap of the Whores

Orgy in Only in the Ap of the Whores

XHamster 4 months ago

delicious food in a condom jerk and cum

delicious food in a condom jerk and cum

XHamster 1 year ago

Thick Ass Taking Every Inch of Girl Cock

Thick Ass Taking Every Inch of Girl Cock

XHamster 3 months ago

First Time Fisting Video with Cagedjock Part 2 Interview and Fisting, Nipple Play Butt Plug, Massage Machine and Pegging

First Time Fisting Video with Cagedjock Part 2 Interview and Fisting, Nipple Play Butt Plug, Massage Machine and Pegging

XHamster 5 months ago

Publication date: Jan 12, 2026 Sexy little sun ended up suffering with three large-dicked ebony chaps, having her little butt ripped open and filled with three loads from the ebony studs thirsty for an booty, Part two.

Publication date: Jan 12, 2026 Sexy little sun ended up suffering with three large-dicked ebony chaps, having her little butt ripped open and filled with three loads from the ebony studs thirsty for an booty, Part two.

ShemaleSin 5 months ago

He Cheated on His Wife with His Transvestite Sister-in-law

63% HD 0:39 / 25:22

He Cheated on His Wife with His Transvestite Sister-in-law

FapHouse 3 months ago

Yasmine Lee: The Ass Fucking Masseuse cums in his mouth

59% 0:25 / 20:24

Yasmine Lee: The Ass Fucking Masseuse cums in his mouth

Clips4sale 1 year ago

Instead of Lessons, Hard Fucking and Cum in the Ass to the Limit! Twink Is Enjoying It!

Instead of Lessons, Hard Fucking and Cum in the Ass to the Limit! Twink Is Enjoying It!

FapHouse 4 months ago

French tgirl : his first time with a sexy dicky girl

French tgirl : his first time with a sexy dicky girl

AShemaleTube 5 years ago

Ruined Anus Transsexual Ben Fucking her Ass with Extreme Inflatable Dildo and Anal Creampie

Ruined Anus Transsexual Ben Fucking her Ass with Extreme Inflatable Dildo and Anal Creampie

XHamster 1 week ago

Youngster with a big ass gets a raw anal pounding in German without protection

Youngster with a big ass gets a raw anal pounding in German without protection

GayVD 1 month ago

The Gay Awakening Podcast Episode #34

The Gay Awakening Podcast Episode #34

Clips4sale 3 years ago

My Very First Time

My Very First Time

BeMyHole 2 years ago

First Time Cream Pie

67% HD 0:39 / 40:51

First Time Cream Pie

FapHouse 6 months ago

Part 2 Crossdresser amateur slut tries to squirt on a cock for guys and milf stepmom

Part 2 Crossdresser amateur slut tries to squirt on a cock for guys and milf stepmom

XHamster 2 months ago

Its the first time you show me your pecker and let me suck it

Its the first time you show me your pecker and let me suck it

Pornwhite 1 month ago

Stepson Wakes up BBW Step Mom to get First Anal Sex with her

Stepson Wakes up BBW Step Mom to get First Anal Sex with her

XHamster 5 years ago

This is our first time fucking a transsexual babe

This is our first time fucking a transsexual babe

XHamster 11 years ago

Locked Sissy Teases Her Tight Hole - Almost Reached Anal Orgasm

Locked Sissy Teases Her Tight Hole - Almost Reached Anal Orgasm

XHamster 3 weeks ago

my ass is so sexy for cock

my ass is so sexy for cock

XHamster 2 weeks ago

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