First Time Anal Videos - Trans (16,553)

First Double-penetration interracial 3-way for FTM

HD 1:01 / 36:56

First Double-penetration interracial 3-way for FTM

FapHouse 3 years ago

Young straight guy with a perfect body likes anal sex

Young straight guy with a perfect body likes anal sex

xHamster 2 years ago

My Stepbrother Wants to Pop My Anal Cherry

My Stepbrother Wants to Pop My Anal Cherry

XXXShake 1 year ago

”Transsexual Date Ends Up In The Bed”

”Transsexual Date Ends Up In The Bed”

TransHero 6 years ago

Bald guy gets his tight ass pounded hard by the tranny babe for the first time

Bald guy gets his tight ass pounded hard by the tranny babe for the first time

Tranny.one 4 years ago

Gorgeous Nerdy Trans Girl Gets Hard Fucking!

Gorgeous Nerdy Trans Girl Gets Hard Fucking!

xHamster 3 months ago

My Friend's Boyfriend Cums Inside My Tight Gay Ass When His Boyfriend Is Studying

47% HD 1:01 / 5:43

My Friend's Boyfriend Cums Inside My Tight Gay Ass When His Boyfriend Is Studying

FapHouse 1 year ago

Daddy Dildo Too Big (3 Day Load)

Daddy Dildo Too Big (3 Day Load)

GayJack 3 years ago

Red Latex Dress POV Bottom

Red Latex Dress POV Bottom

xHamster 1 month ago

Threesome of a Fat Man and Two Trans Girls

HD 1:01 / 26:30

Threesome of a Fat Man and Two Trans Girls

FapHouse 4 months ago

NEW sissy gets deflowered with monster DILDO

NEW sissy gets deflowered with monster DILDO

xHamster 1 year ago

My Dick Curve Dick Is Too Big for This Homie Guy

My Dick Curve Dick Is Too Big for This Homie Guy

xHamster 8 months ago

Introduction to double anal for two beginner sluts

Introduction to double anal for two beginner sluts

Lesbian8 10 months ago

Bangladesh male masturbation Bangladesh male masturbation

Bangladesh male masturbation Bangladesh male masturbation

xHamster 1 month ago

Father Fake Penis Too Ginormous (three Day Fountain)

Father Fake Penis Too Ginormous (three Day Fountain)

4Gay 1 year ago

Sexy Red Bone Tranny Fuck Guy In His Tight Ass

Sexy Red Bone Tranny Fuck Guy In His Tight Ass

xHamster 5 months ago

Amateur big ass is too tight make me cum fast that I did not expect

Amateur big ass is too tight make me cum fast that I did not expect

xHamster 1 year ago

I stopped and tried masturbating while holding back my ejaculation

I stopped and tried masturbating while holding back my ejaculation

xHamster 6 months ago

Kendal Penny has anal fun in college

Kendal Penny has anal fun in college

xHamster 5 years ago

Secret santa Harin experienced a hard orgasm when she got an anal fisting for the first time and fucked by new crystal dildos.

Secret santa Harin experienced a hard orgasm when she got an anal fisting for the first time and fucked by new crystal dildos.

xHamster 4 months ago

Waking up with a Hard Ladyboy Cock Sapphire Is Ready for a Hot Hard Anal Fuck

Waking up with a Hard Ladyboy Cock Sapphire Is Ready for a Hot Hard Anal Fuck

xHamster 1 year ago

Introducing Robinbunny! Your Next Favorite Sub Slut

Introducing Robinbunny! Your Next Favorite Sub Slut

FapHouse 1 month ago

My first time with a BBC

My first time with a BBC

Tranny.one 1 year ago

Shemale teen first time bareback

Shemale teen first time bareback

Tranny.one 4 years ago

So youve never been with a trans woman

So youve never been with a trans woman

aShemaleTube 4 weeks ago

Jade Venus Is Meeting Her Mother-In-Law For The First Time And Her Pussy At The Same Time

Jade Venus Is Meeting Her Mother-In-Law For The First Time And Her Pussy At The Same Time

BeMyHole 3 years ago

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

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

xHamster 1 month ago

Turning my straight friend into a gay after he bred me.

Turning my straight friend into a gay after he bred me.

xHamster 3 months ago

First Time with New BBC Sized Dildo Makes Daphne Moan and Dribble Her Sissy Cum Everywhere 4K

First Time with New BBC Sized Dildo Makes Daphne Moan and Dribble Her Sissy Cum Everywhere 4K

xHamster 1 day ago

Srossdress first time trying out latex

Srossdress first time trying out latex

GayXPS 2 years ago

Lingerie versatile ladyboy assfucking dude

Lingerie versatile ladyboy assfucking dude

TransJizz 2 years ago

GIA ITZEL HAS A DATE WITH A TINDER BOY, THEY GO TO THE MOTEL AND THEY FUCK HER HARD

GIA ITZEL HAS A DATE WITH A TINDER BOY, THEY GO TO THE MOTEL AND THEY FUCK HER HARD

xHamster 2 years ago

Paola Santrelly Loves Monster Cock

Paola Santrelly Loves Monster Cock

xHamster 5 months ago

Another lesson with a pink strapon and a sissy slut in a sexy bodysuit

Another lesson with a pink strapon and a sissy slut in a sexy bodysuit

xHamster 1 year ago

JOI - JERK OFF INSTRUCTIONS UNTIL YOU CUM IN MY ASS

JOI - JERK OFF INSTRUCTIONS UNTIL YOU CUM IN MY ASS

Pornzona 2 weeks ago

Fucking Mtf Chastity Charlie

Fucking Mtf Chastity Charlie

xHamster 1 month ago

”GROOBY.CLUB: Crystal Thayer On Top”

”GROOBY.CLUB: Crystal Thayer On Top”

429Men 2 months ago

”TGIRLS PORN - The Inked Twosome”

”TGIRLS PORN - The Inked Twosome”

Faptor 6 days ago

First time in the Ass iwant a doggy style!

First time in the Ass iwant a doggy style!

aShemaleTube 1 year ago

Hot Summer Girl MILF Cumshot in Hot Summer

HD 1:01 / 12:40

Hot Summer Girl MILF Cumshot in Hot Summer

FapHouse 3 days ago

Batbunz Abandoned Palace Currency-Shots

Batbunz Abandoned Palace Currency-Shots

2BGay 2 years ago

Pristine Edge first time to fuck by a trans Kate Zoha

Pristine Edge first time to fuck by a trans Kate Zoha

Yeswegays 3 years ago

Eva Lin First Time On Camera For An Intense Session Of Female Led Play

Eva Lin First Time On Camera For An Intense Session Of Female Led Play

aShemaleTube 3 weeks ago

Riding cuCUMber for a huge Belly Bulge!

Riding cuCUMber for a huge Belly Bulge!

xHamster 3 months ago

Ladysilva fucking my greedy ass with a thick dildo

Ladysilva fucking my greedy ass with a thick dildo

xHamster 3 weeks ago

OPERATED TS Alysha Mia hardcore screw and piddle in dude's throat

OPERATED TS Alysha Mia hardcore screw and piddle in dude's throat

ShemaleSin 4 months ago

Fat asses teen transsexual gets fucked first time

64% HD 1:01 / 20:39

Fat asses teen transsexual gets fucked first time

FapHouse 8 years ago

Fur covered femboy get rectally boinked by a stranger and finishes up inwards him (Scratchdex toon) - Jazziuu

Fur covered femboy get rectally boinked by a stranger and finishes up inwards him (Scratchdex toon) - Jazziuu

Gayhaus 5 months ago

Ladyboy angel Real Sex likes coarse Screwing ass slam, Unfathomable stretching for a t-girl trans beauty floozy Large Wang

Ladyboy angel Real Sex likes coarse Screwing ass slam, Unfathomable stretching for a t-girl trans beauty floozy Large Wang

ShemaleSin 3 days ago

A virgin spunking from his dad's torrid jizz splash and his milky pearl juice mixed into one splash of jizz!

A virgin spunking from his dad's torrid jizz splash and his milky pearl juice mixed into one splash of jizz!

MenGem 9 months ago

Amateur, fucking me all over with my big dick toys

Amateur, fucking me all over with my big dick toys

xHamster 6 months ago

Agatha Mama In Teaching My Step Cousin How To Eat A Trans Woman For The First Time.

Agatha Mama In Teaching My Step Cousin How To Eat A Trans Woman For The First Time.

BeMyHole 2 weeks ago

Desi Villages Beautiful Twink & Town Gay Bareback Threesome Gay Couple Village Sex - Locker Room

Desi Villages Beautiful Twink & Town Gay Bareback Threesome Gay Couple Village Sex - Locker Room

xHamster 2 years ago

”Buck Richards takes on Transgender Jexxxica Blake's fat black dick”

”Buck Richards takes on Transgender Jexxxica Blake's fat black dick”

Zatube 1 year ago

Don Nathan Fucks Marine in the Jacuzzi with His Moster Cock

64% 1:01 / 13:08

Don Nathan Fucks Marine in the Jacuzzi with His Moster Cock

FapHouse 2 months ago

561 Tgata Ebony Leticia Diniz Dotadona inserts a 22 cm thick cock into the little ass of the sucking slut.

561 Tgata Ebony Leticia Diniz Dotadona inserts a 22 cm thick cock into the little ass of the sucking slut.

xHamster 1 month ago

Rawhole - Gay Augusto Phellipe kissing each other sex scene

Rawhole - Gay Augusto Phellipe kissing each other sex scene

GayTube.site 2 years ago

Wow First Time touch truck driver big monster cock

Wow First Time touch truck driver big monster cock

xHamster 2 years ago

JOI - You will punheta this pipe and you will be punheta, doubt you won't love the regression - hot hardcore porn!

JOI - You will punheta this pipe and you will be punheta, doubt you won't love the regression - hot hardcore porn!

FetishShrine 11 months ago

No146 Bullying Training 1 I'm Peeing

No146 Bullying Training 1 I'm Peeing

xHamster 1 month ago

Sexy Ass

FapHouse 1 week ago

My Husband Arranged for Us to Meet so I Won't Leave Him

55% 1:01 / 40:48

My Husband Arranged for Us to Meet so I Won't Leave Him

FapHouse 2 months ago

Skinny teen shemale is getting banged

Skinny teen shemale is getting banged

Eporner 3 years ago

Flip Fuck POV with Bwc

Flip Fuck POV with Bwc

xHamster 3 weeks ago

She-Creature Teenie Cassie Shrieks Donk Ravaged & Hair Pulled

She-Creature Teenie Cassie Shrieks Donk Ravaged & Hair Pulled

TrannyGem 2 years ago

Fucked Raw by Xxl Black Cock

HD 1:01 / 20:42

Fucked Raw by Xxl Black Cock

FapHouse 6 days ago

My stepbro was too slow… so I made the first move, giving him a blowjob

My stepbro was too slow… so I made the first move, giving him a blowjob

ShemaleSex 3 months ago

Bhojpuri Superhit Subscribe to My Fabhosue

Bhojpuri Superhit Subscribe to My Fabhosue

xHamster 3 weeks ago

”GENDER X Fucking my tbabe friend for the first time! - Dante Colle, Ariel Demure”

”GENDER X Fucking my tbabe friend for the first time! - Dante Colle, Ariel Demure”

StarWank 5 years ago

Anaka's Masturbates in H

Anaka's Masturbates in H

xHamster 4 weeks ago

Sexy Big Titts Tattoed Asina Ladyboy Mistress Fucks with Big Ass Guy Anal

Sexy Big Titts Tattoed Asina Ladyboy Mistress Fucks with Big Ass Guy Anal

xHamster 3 weeks ago

Ladysilva on all fours on the beach fucking her hot ass with a big thick cock I got all open

Ladysilva on all fours on the beach fucking her hot ass with a big thick cock I got all open

xHamster 1 month ago

Trans Taking an Anal Virginity

Trans Taking an Anal Virginity

xHamster 11 months ago

Vey Puffy: Hot Shemale in Glasses Gets Stuffed by Two Toys (Part 01)

Vey Puffy: Hot Shemale in Glasses Gets Stuffed by Two Toys (Part 01)

xHamster 1 week ago

Horny amateur crossdressing trans uses anal vibrator cock ring and tack pussy to masturbate in stockings and heels

Horny amateur crossdressing trans uses anal vibrator cock ring and tack pussy to masturbate in stockings and heels

xHamster 2 months ago

Crossdressers First Time

Crossdressers First Time

Tranny.one 4 years ago

Indian Gay Sex Video - Straight Friend & Pornstar

Indian Gay Sex Video - Straight Friend & Pornstar

xHamster 3 years ago

”TGIRLS PORN - The Inked Twosome”

”TGIRLS PORN - The Inked Twosome”

HQBang 3 weeks ago

TRANSFIXED - Trans Babysitter Zariah Aura Gives It Up To Her Boss On Her First Day!

TRANSFIXED - Trans Babysitter Zariah Aura Gives It Up To Her Boss On Her First Day!

xHamster 3 years ago

Czech Hunter - Tight boyfriend wishes for loud sex

Czech Hunter - Tight boyfriend wishes for loud sex

GayTube.site 4 years ago

My 1st Time Anal

My 1st Time Anal

Lesbian8 3 months ago

I Fell Into My Friend's Trap with the Big 22cm Dick

65% HD 1:01 / 22:08

I Fell Into My Friend's Trap with the Big 22cm Dick

FapHouse 1 month ago

The Street Twink on My Dick

The Street Twink on My Dick

xHamster 1 month ago

Public Poolside ANAL with BIG ASS elf and HUGE DICK Draenei Futa

Public Poolside ANAL with BIG ASS elf and HUGE DICK Draenei Futa

HentaiGem 2 years ago

Self-sucking slut with a double cock squirts cum in her mouth

Self-sucking slut with a double cock squirts cum in her mouth

xHamster 1 month ago

MissionaryBoys: Incredible Elder Dobrovnik pounding blowjob

MissionaryBoys: Incredible Elder Dobrovnik pounding blowjob

GayTube.site 4 years ago

free Pearl skin whiteboy gets pegged by ebony girl

free Pearl skin whiteboy gets pegged by ebony girl

aShemaleTube 4 months ago

Femboy Fat Ass Boils First Anal Double Dildo Cum Gush Destroyed

Femboy Fat Ass Boils First Anal Double Dildo Cum Gush Destroyed

GayPornWatch 2 days ago

GROOBYVR - Meet The Ravines

GROOBYVR - Meet The Ravines

Fapnado 3 weeks ago

My Trans Gf bonks Me For The Very first Time. that stunner loves How that stunner bonks My butt

My Trans Gf bonks Me For The Very first Time. that stunner loves How that stunner bonks My butt

TransTube.tv 11 months ago

He said he never attempted Ass-Fuck so I put this Acquaintance on Him… He’s DONE with Cooter

He said he never attempted Ass-Fuck so I put this Acquaintance on Him… He’s DONE with Cooter

TrannyGem 3 years ago

My furry girlfriend can't get enough of my big cock in her ass - Animation - Jazziuu

My furry girlfriend can't get enough of my big cock in her ass - Animation - Jazziuu

TrannyMovs 7 months ago

SATANS TGIRLS - Sweetheart Spencer Bradley Smashes For Her Very First Time With A Trans And It's Korra Del Rio

SATANS TGIRLS - Sweetheart Spencer Bradley Smashes For Her Very First Time With A Trans And It's Korra Del Rio

KeekAss 3 years ago

fanny menezes sexy tranny fanny menezes takes two cocks in the ass for the first time

fanny menezes sexy tranny fanny menezes takes two cocks in the ass for the first time

PornOne 2 years ago

Selbstbefriedigung

Selbstbefriedigung

xHamster 3 years ago

He came in my ass and kept putting it

He came in my ass and kept putting it

xHamster 3 months ago

Red Latex Dress POV Bottom

Red Latex Dress POV Bottom

FapHouse 1 month ago

Tgirl Teen Cassie Bellows gets LARGE buttfuck cream pie

Tgirl Teen Cassie Bellows gets LARGE buttfuck cream pie

TransTube.tv 1 year ago

”First time ass fucking for ebony amateur”

”First time ass fucking for ebony amateur”

ThePornstar 1 year ago

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

63% 1:01 / 21:29

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

FapHouse 1 month ago

My wife lets me fuck her ass for first time

My wife lets me fuck her ass for first time

Eporner 8 months ago

Destroying My 18YO Twink Stepsons Fat Ass Pronebone Bareback Cumflood

Destroying My 18YO Twink Stepsons Fat Ass Pronebone Bareback Cumflood

GayPornWatch 2 months ago

The guy tries anal sex for the first time Shemale MILF

The guy tries anal sex for the first time Shemale MILF

FetishShrine 2 days ago

jerking off while imagining a big dick

jerking off while imagining a big dick

xHamster 5 months ago

A cute Asian boy masturbates and ejaculates for the first time in 2026 in a sunny and cozy little house.

A cute Asian boy masturbates and ejaculates for the first time in 2026 in a sunny and cozy little house.

xHamster 3 months ago

Stepdad fucks stepson in the ass on the toilet - 363

Stepdad fucks stepson in the ass on the toilet - 363

xHamster 2 years ago

A Young Finnish Trans Gets Cock for the First Time

A Young Finnish Trans Gets Cock for the First Time

xHamster 2 months ago

Fucking Hotsolzinha's ass in the fur

Fucking Hotsolzinha's ass in the fur

xHamster 3 months ago

Huge BBC Fucks Sissy Samantha

Huge BBC Fucks Sissy Samantha

xHamster 6 months ago

”GROOBY.CLUB: INTRODUCING JENISSEN JENNY!”

”GROOBY.CLUB: INTRODUCING JENISSEN JENNY!”

Fapnow 2 years ago

Sissy Transition CLINIC - Obedience Training

Sissy Transition CLINIC - Obedience Training

xHamster 1 year ago

AI Generated Storm Tranny Babe rides enemy monster cock Clip 2

AI Generated Storm Tranny Babe rides enemy monster cock Clip 2

xHamster 2 months ago

Fucked myself with brinjal

Fucked myself with brinjal

xHamster 1 month ago

May Sissy Cumpilation

May Sissy Cumpilation

TrannyGem 1 year ago

My stepsister lay down on the bed and asked me to fuck her ass for the first time

My stepsister lay down on the bed and asked me to fuck her ass for the first time

Lesbian8 8 months ago

Straight Guy Arrives After Party and Finds a Beautiful Trans Girl

Straight Guy Arrives After Party and Finds a Beautiful Trans Girl

xHamster 4 weeks ago

Gorgeous Nerdy Trans Girl Gets Hard Fucking!

63% HD 1:01 / 45:22

Gorgeous Nerdy Trans Girl Gets Hard Fucking!

FapHouse 3 months ago

First Time Cream Pie

First Time Cream Pie

xHamster 3 months ago

Two Married Men Have Gay Anal Sex in Their Boss's Secret Apartment.

Two Married Men Have Gay Anal Sex in Their Boss's Secret Apartment.

xHamster 1 month ago

We had a first time threesome with a trans woman

We had a first time threesome with a trans woman

Fapnado 3 years ago

15 16 17 18 19

16,553 results found

Related categories

First Anal Skinny Anal Anal Creampie Amateur Anal Redhead Anal Anal Creampie Compilation Amateur Anal Sex Anal Compilation Hairy Anal Cum Inside Anal Anal Gape Amateur Teen Anal 18+ Anus Small Tits Anal Story Anal Anal Extreme Asshole Anal Casting Anal Fingering Anal Squirt

Narrow your search

teen anal first time 18+ first time anal homemade first time anal creampie amateur first time anal teen first time anal 18+ real first time anal first time anal casting first time anal compilation first time anal teen 18+ first time anal amateur wife first time anal amateur anal first time mature first time anal homemade first time anal first time anal bbc first time bbc anal sasha grey first time anal bree olson first time anal anal amateur first time

Categories Pornstars

Categories Pornstars

Parents

Pornmd.com uses the "Restricted To Adults" (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Pornmd.com. All rights reserved.

© 2026 Pornmd.com. All rights reserved.