First Time Anal Videos - Trans (16,549)

Tgirls Experience #27

Tgirls Experience #27

xHamster 6 months ago

First time

aShemaleTube 9 years ago

I Used Several Balls to Dilate That Bitch's Asshole

I Used Several Balls to Dilate That Bitch's Asshole

FapHouse 1 week ago

Mama Studio Presents "Teaching My Step Cousin To Eat A Trans For The First Time" - Free

Mama Studio Presents "Teaching My Step Cousin To Eat A Trans For The First Time" - Free

BeMyHole 3 weeks ago

Crossdressed twink fucked raw by straight boy discreet

Crossdressed twink fucked raw by straight boy discreet

xHamster 3 months ago

I wore a cute dress and gave a guy a blowjob.

I wore a cute dress and gave a guy a blowjob.

xHamster 1 month 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

Virgin wanted to have unforgettable first time with both of us

Virgin wanted to have unforgettable first time with both of us

aShemaleTube 10 months ago

Studying my cherry arse with my dearest condom

Studying my cherry arse with my dearest condom

Gayhub 1 day ago

College-Aged Porn – Jamie French And Bambi Bliss – Very First Time OTS846

College-Aged Porn – Jamie French And Bambi Bliss – Very First Time OTS846

TrannyGem 3 years ago

I Fuck Transvestite Slut in My Building in the Ass and Cum Inside Her Tight Ass

I Fuck Transvestite Slut in My Building in the Ass and Cum Inside Her Tight Ass

xHamster 1 month ago

Fucking Everything Up Her Tight Pussycat Ass

Fucking Everything Up Her Tight Pussycat Ass

XXXShake 1 year ago

My trans gf pokes me for the very first time. She enjoys how she plumbs my donk

My trans gf pokes me for the very first time. She enjoys how she plumbs my donk

KeekAss 2 years ago

Handcuffed crossdresser anal

Handcuffed crossdresser anal

xHamster 1 year ago

Tgirls Experience #27

66% HD 1:01 / 1:30:27

Tgirls Experience #27

FapHouse 10 months ago

Anal Play With Amy Nosferatu - Temptress Split Tongue Seduction Turns Roommie’s first Trans Bang

Anal Play With Amy Nosferatu - Temptress Split Tongue Seduction Turns Roommie’s first Trans Bang

Amateur8 10 months ago

Petite Trans Latina Girl Fucked by Tourist

Petite Trans Latina Girl Fucked by Tourist

xHamster 2 months ago

Tattooed Trans Girl in Doggy Style Plays with Asshole and Cock

Tattooed Trans Girl in Doggy Style Plays with Asshole and Cock

xHamster 1 month ago

Massive BBC tranny destroys cute white femboy's rectal hole raw and cums inside

Massive BBC tranny destroys cute white femboy's rectal hole raw and cums inside

ShemaleSin 3 weeks ago

First Time Anal with Tundra

First Time Anal with Tundra

Tranny.one 3 years ago

Naughty Japanese Undergarments Galore: A Wild Threesome with a Hunk & A Hottie

Naughty Japanese Undergarments Galore: A Wild Threesome with a Hunk & A Hottie

GayX 2 weeks ago

Femboy Sissy Becomes the Slut of Two Dicks Big Brunette and Fat Hairy White Fill His Anus

Femboy Sissy Becomes the Slut of Two Dicks Big Brunette and Fat Hairy White Fill His Anus

xHamster 1 month ago

Introduction to double anal for two beginner sluts

Introduction to double anal for two beginner sluts

PornFreeNow 10 months ago

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

70% HD 1:01 / 6:21

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

FapHouse 1 month ago

Evelyn Grinding My Ass in Circles & Gives Me Pleasure

48% HD 0:39 / 8:35

Evelyn Grinding My Ass in Circles & Gives Me Pleasure

FapHouse 2 months ago

My very first time with a dwarf. He porked my lil' bootie so great.

My very first time with a dwarf. He porked my lil' bootie so great.

TrannyGem 3 weeks ago

”Who Is the Flame-haired Chick Mini Stallion?”

”Who Is the Flame-haired Chick Mini Stallion?”

429Men 2 months ago

Me and My Homies in a One Night Stand

Me and My Homies in a One Night Stand

FapHouse 2 months ago

Screaming and Moaning as a Big Cock Shoots Cum Into My Hole

63% HD 1:01 / 7:31

Screaming and Moaning as a Big Cock Shoots Cum Into My Hole

FapHouse 2 months ago

From Tease to Full Feminine Exposure (#Femboy #Transformation #Submissive)

From Tease to Full Feminine Exposure (#Femboy #Transformation #Submissive)

xHamster 8 months ago

”Ultra Tightenthe Ass with HUGE Dildo!”

”Ultra Tightenthe Ass with HUGE Dildo!”

LesbianBliss 4 months ago

Black stiffy sissy song

Black stiffy sissy song

TrannyGem 4 years ago

BBC Fucks a Tranny for the First Time in an Interracial Encounter

BBC Fucks a Tranny for the First Time in an Interracial Encounter

xHamster 6 months ago

No152 Bullying Breaking In 2 FUCK ME

No152 Bullying Breaking In 2 FUCK ME

xHamster 1 month ago

Extraordinary Giant Dragon Sex Tool Stretches Teen out

Extraordinary Giant Dragon Sex Tool Stretches Teen out

ShemaleSin 4 years ago

Be Mine Only Mine

Be Mine Only Mine

xHamster 1 month ago

eighteen year old Finnish sexy trans Victoriababy enjoys Dad's thick dong.

eighteen year old Finnish sexy trans Victoriababy enjoys Dad's thick dong.

ShemaleSin 1 year ago

Watch graceful Brittney Kade's trailer

Watch graceful Brittney Kade's trailer

PornHat 6 days ago

Teen Femboy Masturbation Anal

Teen Femboy Masturbation Anal

xHamster 10 months ago

Chrystal Medeiros cums in a stranger's ass

Chrystal Medeiros cums in a stranger's ass

xHamster 1 year ago

First time anal couple sex blonde tgirl

First time anal couple sex blonde tgirl

aShemaleTube 7 years ago

This man put me in the sexual postures that thrill him the most, so he concluded up smashing me until I reached climax and fulfilling our sexual wishes because that makes us squeal with gusto.

This man put me in the sexual postures that thrill him the most, so he concluded up smashing me until I reached climax and fulfilling our sexual wishes because that makes us squeal with gusto.

TrannyGem 1 week ago

jerking off while imagining a big dick

jerking off while imagining a big dick

xHamster 5 months ago

A Berlin Night

xHamster 1 month ago

MY VERY FIRST TIME WITH A TRANSVESTI! (JÚLIA DENTTELO)

MY VERY FIRST TIME WITH A TRANSVESTI! (JÚLIA DENTTELO)

TrannyGem 4 years ago

Bf gets drilled in rump by trans gf, go after Daniela Chanel! My OF is free-for-all!

Bf gets drilled in rump by trans gf, go after Daniela Chanel! My OF is free-for-all!

Transvids.tv 10 months ago

Casey Lay Fucks Herself

66% HD 1:01 / 13:03

Casey Lay Fucks Herself

FapHouse 3 weeks ago

Tranny slut ass fucking gay friend - Fucked For The Very First Time - Domino Presley

Tranny slut ass fucking gay friend - Fucked For The Very First Time - Domino Presley

Xtits 2 years ago

first time for my husband fuck with Ladyboy Full (Free Movie scene)

first time for my husband fuck with Ladyboy Full (Free Movie scene)

Dafreeporn 9 months ago

My First Time with a Shemale Pornstar - Elisa Sanches

My First Time with a Shemale Pornstar - Elisa Sanches

Jizzberry 3 years ago

First Time Having Sex with a Brazilian Trans Girl.

First Time Having Sex with a Brazilian Trans Girl.

xHamster 3 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

Fapnado 2 weeks ago

First Time Pleasure with My Street Friend

First Time Pleasure with My Street Friend

xHamster 8 months ago

Ultimate TS Seduction In The Steam Room

Ultimate TS Seduction In The Steam Room

BeMyHole 1 week ago

Compilation of Very Hot Twinks Having Bareback Anal Sex.

Compilation of Very Hot Twinks Having Bareback Anal Sex.

xHamster 6 months ago

Anal Boundary Exceeded???

68% HD 1:01 / 12:21

Anal Boundary Exceeded???

FapHouse 1 year ago

Fabulous twink has anal sex for first time as a sissy : see

Fabulous twink has anal sex for first time as a sissy : see

ManPorn 3 years ago

Part Ii Seth, Fucked a Trans for the First Time

63% 0:39 / 10:24

Part Ii Seth, Fucked a Trans for the First Time

FapHouse 2 months ago

Cute Twink Cruise in the Room

Cute Twink Cruise in the Room

xHamster 1 month ago

Blonde Tranny Ass Fucked in Condom - Tiny Tgirl’s First Time On Camera - Ramon

Blonde Tranny Ass Fucked in Condom - Tiny Tgirl’s First Time On Camera - Ramon

Xtits 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

Creampie Fucking Young Gay Bareback in Bathroom I Cum Inside His Ass Cruising

Creampie Fucking Young Gay Bareback in Bathroom I Cum Inside His Ass Cruising

xHamster 1 year ago

That Giant Penis Reaches All the Way to My Throat!

That Giant Penis Reaches All the Way to My Throat!

xHamster 7 months ago

Obedient Slave Fucked Apart

Obedient Slave Fucked Apart

xHamster 1 year ago

Amateur Crossdresser in stocking heels skirt seduces husband to her room gives blowjob, but hubby keeps talking about milf wild

Amateur Crossdresser in stocking heels skirt seduces husband to her room gives blowjob, but hubby keeps talking about milf wild

xHamster 3 months ago

Blonde teen shemale gets fucked hard first time

Blonde teen shemale gets fucked hard first time

Tranny.one 4 years ago

Hot shemale fucks for first time her boyfriend

Hot shemale fucks for first time her boyfriend

Tranny.one 4 years ago

”Submissive tranny Monique Miles analized”

”Submissive tranny Monique Miles analized”

429Men 2 months ago

Shemale first time sex with a guy

Shemale first time sex with a guy

aShemaleTube 5 years ago

Foreskin squirts cum from a bloated huge dick! Exclusive! It's hot!!!

Foreskin squirts cum from a bloated huge dick! Exclusive! It's hot!!!

xHamster 1 year ago

Dudes pounding bubble butts rough and hard

Dudes pounding bubble butts rough and hard

analpornvids 2 weeks ago

Femboy Cums Very Hard and His Cock Gets Hard and Fat

Femboy Cums Very Hard and His Cock Gets Hard and Fat

xHamster 3 months ago

Instinct Unleashed gameplay parte 1

Instinct Unleashed gameplay parte 1

xHamster 6 months ago

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

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

FapHouse 1 week ago

Twink Femboy Loves to Drink Sweet Precum of Big Blue Futanari Mistress

Twink Femboy Loves to Drink Sweet Precum of Big Blue Futanari Mistress

xHamster 3 months ago

Emma Rose and Leah Hayes get their first time fuck with a big-dicked dude

Emma Rose and Leah Hayes get their first time fuck with a big-dicked dude

TrannyMovs 7 months ago

Good-Sized assfucking buttplug and assfucking beads demolishing my butt-hole

Good-Sized assfucking buttplug and assfucking beads demolishing my butt-hole

TrannyGem 2 years ago

”Asian TBabe Annalise Rose's First Time with TBabe Honey Foxxx”

”Asian TBabe Annalise Rose's First Time with TBabe Honey Foxxx”

Trashreality 1 year ago

Sissy Transition CLINIC - Obedience Training

Sissy Transition CLINIC - Obedience Training

xHamster 1 year ago

Huge Cock Guy Fucking Shemale Asshole Anal Sex And Creampies

Huge Cock Guy Fucking Shemale Asshole Anal Sex And Creampies

xHamster 1 month ago

First time anal couple sex blonde tgirl

First time anal couple sex blonde tgirl

Tranny.one 4 years 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

free Cute white femboy bangs with giant ebony dong trans cutie bareback, this babe even cums inside his butt

free Cute white femboy bangs with giant ebony dong trans cutie bareback, this babe even cums inside his butt

ShemaleSin 1 month ago

Naked ladysilva in bed with an ass butt plug in her hot ass

Naked ladysilva in bed with an ass butt plug in her hot ass

xHamster 2 weeks ago

Thai Transgender Princess

Thai Transgender Princess

TrannyGem 4 years 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

The Secretary Messed up the Job and the Trans Boss Showed No Mercy, She Had Sex with Him and Took off the Condom During the Act.

The Secretary Messed up the Job and the Trans Boss Showed No Mercy, She Had Sex with Him and Took off the Condom During the Act.

xHamster 6 days 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

Married couple home pegging training

Married couple home pegging training

xHamster 1 year ago

Blasting balls-deep into my slut's wrecked shithole

Blasting balls-deep into my slut's wrecked shithole

xHamster 1 month ago

twenty one yo Finnish trans doll's first-ever time getting poked on camera

twenty one yo Finnish trans doll's first-ever time getting poked on camera

TrannyGem 1 year ago

First Time Be with My Gateman

First Time Be with My Gateman

xHamster 5 months ago

Ai Generated Huge Boobs Trans Sucking Massive Dick While Cum Hard

Ai Generated Huge Boobs Trans Sucking Massive Dick While Cum Hard

xHamster 1 month ago

Sissy Training After First Time Feminization

Sissy Training After First Time Feminization

xHamster 2 years ago

Ladyboystar - POINT OF VIEW anal invasion and oral with a uber-cute young transgirl

Ladyboystar - POINT OF VIEW anal invasion and oral with a uber-cute young transgirl

TrannyGem 2 weeks ago

first time sucking a shemale cock estela duarte

first time sucking a shemale cock estela duarte

PissVids 3 years ago

Sissy precum for the first time

Sissy precum for the first time

xHamster 7 months ago

Kira yhivi and Victor

Kira yhivi and Victor

Some.Porn 8 months ago

Our first night as husband and wife

Our first night as husband and wife

xHamster 4 months ago

From Jackhammer to Sensual: Fisting Lessons from a Queen - Cliff Media

From Jackhammer to Sensual: Fisting Lessons from a Queen - Cliff Media

Pornzona 3 days ago

Nani X Lilo cheats on husband with sissy man deep anal sex AI Generated Clip 2

Nani X Lilo cheats on husband with sissy man deep anal sex AI Generated Clip 2

xHamster 1 month ago

Ruined orgasm on the face of a femboy twink crossdresser!

Ruined orgasm on the face of a femboy twink crossdresser!

xHamster 1 year ago

Paidocarmona Filmed Him Sofie's

Paidocarmona Filmed Him Sofie's

xHamster 1 month ago

Slutty Amateur Crossdresser Trans Female Talks Dirty to Her Girlfriend Stepmom

Slutty Amateur Crossdresser Trans Female Talks Dirty to Her Girlfriend Stepmom

FapHouse 1 week ago

Instructing My Gorgeous Sissy With 12 Inches Of Stiff Knobs Xxx Bondages Teaching

Instructing My Gorgeous Sissy With 12 Inches Of Stiff Knobs Xxx Bondages Teaching

TrannyGem 3 years ago

Introduction to double anal for two beginner sluts

Introduction to double anal for two beginner sluts

Lesbian8 10 months ago

Hot Shemale Jessica Kate Is Hot, and She Knows How to Win Us Over!

61% HD 1:01 / 50:39

Hot Shemale Jessica Kate Is Hot, and She Knows How to Win Us Over!

FapHouse 1 year ago

Pool Party at Tgatas, and the Night Promises to Continue.

Pool Party at Tgatas, and the Night Promises to Continue.

xHamster 3 months ago

Scarlett And Natalie Having Fun

Scarlett And Natalie Having Fun

xHamster 4 months ago

Stepdad Fucks His Cute Stepson Gay Young Twink Bareback Cums Inside His Ass Anal Creampie

65% HD 1:01 / 14:07

Stepdad Fucks His Cute Stepson Gay Young Twink Bareback Cums Inside His Ass Anal Creampie

FapHouse 1 year ago

HotPinkNymph's first time with StarDust Dragon Amarok: Shaking, moaning, and getting a hot creampie

HotPinkNymph's first time with StarDust Dragon Amarok: Shaking, moaning, and getting a hot creampie

TrannyMovs 8 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

Stepmom surprises me and takes it all

Stepmom surprises me and takes it all

Jizzberry 2 years ago

Nosy Neighbours: Fucking the Sugar That Lives Next Door

Nosy Neighbours: Fucking the Sugar That Lives Next Door

xHamster 1 month ago

Trans Redhead GF Destroys My Virgin Ass First Time Rough Cum Gush

Trans Redhead GF Destroys My Virgin Ass First Time Rough Cum Gush

JuicyTrans 1 week ago

Thrilling moment from "French chubby amateur teen has public sex on the beach"

Thrilling moment from "French chubby amateur teen has public sex on the beach"

xHamster 7 months ago

First Double Fist Fucking for Loren - Mistress Lunatika

61% HD 1:01 / 17:00

First Double Fist Fucking for Loren - Mistress Lunatika

FapHouse 3 months ago

Watching my husband fucks TS makes me horny

Watching my husband fucks TS makes me horny

Yeswegays 2 weeks ago

Kitchen Seduce

xHamster 1 month ago

I am ready to fuck baby

I am ready to fuck baby

xHamster 2 months ago

14 15 16 17 18

16,549 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.