First Time Trans Videos (23,014)

”GROOBYGIRLS - A Star is Born”

”GROOBYGIRLS - A Star is Born”

Zatube 2 weeks ago

”TRANSEXPOV: Laying Down The Law!”

”TRANSEXPOV: Laying Down The Law!”

TransHero 1 year ago

Femboy Gets Bred by Savino Black

Femboy Gets Bred by Savino Black

xHamster 2 weeks ago

”T-girls Chelsea Marie & Aubrey Kate having assfucking threeway with Pierce”

”T-girls Chelsea Marie & Aubrey Kate having assfucking threeway with Pierce”

ThePornstar 1 year ago

FEMOUT XXX - Angel Monroe First Time To Exposed Her Goodies

FEMOUT XXX - Angel Monroe First Time To Exposed Her Goodies

TrannyGem 1 year ago

trans anal sex with real couple cuckold

55% HD 0:10 / 20:52

trans anal sex with real couple cuckold

PornBox 1 year ago

I ALWAYS HAVE A FUN GIVING ORAL PLEASURE-JOB 'COZ THEY SAY VERY SEXY THINGS THAT TURN ME ON AND MAKE ME FEEL SUPER LEWD AND AVID TO FULFILL ALL THEIR RAUNCHY DREAMS UNTIL THEY FINISH INSIDE ME

I ALWAYS HAVE A FUN GIVING ORAL PLEASURE-JOB 'COZ THEY SAY VERY SEXY THINGS THAT TURN ME ON AND MAKE ME FEEL SUPER LEWD AND AVID TO FULFILL ALL THEIR RAUNCHY DREAMS UNTIL THEY FINISH INSIDE ME

ShemaleSin 1 week ago

Slave used in Jacuzzi

57% HD 0:10 / 6:21

Slave used in Jacuzzi

LoyalFans 1 month ago

Ladyboystar - Incredible ladyboy shoves her hard dick in my booty in POV fashion

Ladyboystar - Incredible ladyboy shoves her hard dick in my booty in POV fashion

ShemaleSin 1 month ago

First time in the Ass iwant a doggy style!

First time in the Ass iwant a doggy style!

aShemaleTube 1 year ago

PLUS-SIZE had hook-up with boyceta for the first-ever time

PLUS-SIZE had hook-up with boyceta for the first-ever time

KeekAss 4 days ago

My Secret Desire, Solo Trans Fun

My Secret Desire, Solo Trans Fun

FapHouse 3 days ago

”TGIRLS.PORN: Cloudy Vi & Lilia Lust: 400th TGirls.Porn Scene”

”TGIRLS.PORN: Cloudy Vi & Lilia Lust: 400th TGirls.Porn Scene”

Rainblow 1 year ago

My First time :)

My First time :)

aShemaleTube 2 years ago

Angel : The Sex Demon in Town?

Angel : The Sex Demon in Town?

xHamster 1 month ago

4 Hole Hardcore Humiliation! Part 2 XXX

61% HD 1:01 / 6:37

4 Hole Hardcore Humiliation! Part 2 XXX

FapHouse 9 months ago

PetraTVsletje making her first porn movie with a very big dick

PetraTVsletje making her first porn movie with a very big dick

xHamster 1 year ago

Ts teen bareback first time Forgetful cute Forgiveness

Ts teen bareback first time Forgetful cute Forgiveness

FetishShrine 6 years ago

Venom Sinister gets a harsh BONDAGE & DISCIPLINE sesh from Domina Diosa Diamante

Venom Sinister gets a harsh BONDAGE & DISCIPLINE sesh from Domina Diosa Diamante

TrannyGem 2 years ago

Ashely Ocean Gets Her First Taste of On-Screen Dick in Hardcore Casting

Ashely Ocean Gets Her First Taste of On-Screen Dick in Hardcore Casting

Jizzberry 1 year ago

Chubby amateur femboy strips and toys ass

Chubby amateur femboy strips and toys ass

Tranny.one 4 years ago

Solo Trans Seduction, Don't Look Away

HD 0:39 / 32:14

Solo Trans Seduction, Don't Look Away

FapHouse 5 days ago

Couple Fuck and Cum!!!!!

Couple Fuck and Cum!!!!!

FapHouse 12 hours ago

Emma Rose's Romantic Deepthroat & Anal With Big Dick Roommate

Emma Rose's Romantic Deepthroat & Anal With Big Dick Roommate

XCafe 5 months ago

Ts Jade Venus gives Chanel Noir 1st anal

Ts Jade Venus gives Chanel Noir 1st anal

FetishShrine 4 years ago

Transsurgeon Andy-star Turns You Into a Sissy

56% HD 1:01 / 12:02

Transsurgeon Andy-star Turns You Into a Sissy

FapHouse 11 months ago

”T-girl Jade Venus ready for fuck on family dinner”

”T-girl Jade Venus ready for fuck on family dinner”

LesbianBliss 1 week ago

”Stripper Femboy Gets Manhandled By Buff Bouncers”

”Stripper Femboy Gets Manhandled By Buff Bouncers”

LesbianBliss 2 weeks ago

First to Cum Challenge - Veronica Sanders

First to Cum Challenge - Veronica Sanders

xHamster 10 months ago

My first time with high heals

My first time with high heals

xHamster 3 years ago

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

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

xHamster 8 months ago

”CastingFrancais - Sherly Quinn Canadian First Timer First Porn Audition With Muscular Guy”

”CastingFrancais - Sherly Quinn Canadian First Timer First Porn Audition With Muscular Guy”

ThePornstar 7 months ago

Asian bitch in tight red skirt sits on streetside with a strong vibrator on and ends up masturbating, climaxing back and forth

Asian bitch in tight red skirt sits on streetside with a strong vibrator on and ends up masturbating, climaxing back and forth

xHamster 5 months ago

My First Time With A Trans Man

My First Time With A Trans Man

Nuvid 5 months ago

Swedish Slut Tess Lacey Rides Pascal Hard

Swedish Slut Tess Lacey Rides Pascal Hard

ALOTPorn 3 months ago

”BLACK TGIRLS - The Mighty FreakofdaweekK!!”

”BLACK TGIRLS - The Mighty FreakofdaweekK!!”

TransHero 2 weeks ago

An Acrobatic first TEEN BBG 3some featuring Shrooms Q with Brian Omally and Kai Jaxon

An Acrobatic first TEEN BBG 3some featuring Shrooms Q with Brian Omally and Kai Jaxon

BigTitsLust 1 month ago

Sexy Sissy Tranny Solo Lush Anal Dildo

Sexy Sissy Tranny Solo Lush Anal Dildo

xHamster 3 months ago

Brunette tranny gets deep naughty with wet deepthroat oral fucking before asshole penetration creamping horny with sexy babe

Brunette tranny gets deep naughty with wet deepthroat oral fucking before asshole penetration creamping horny with sexy babe

Tranny.one 3 years ago

Crossdresser Jackie very first time in public

Crossdresser Jackie very first time in public

TrannyGem 1 year ago

Homemade reality demonstrate butt assfuck

Homemade reality demonstrate butt assfuck

TrannyGem 2 years ago

My Very First Time Creeampied a Pumpkin

My Very First Time Creeampied a Pumpkin

TrannyGem 2 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.

HD 0:39 / 12:11

Secret Santa Harin Experienced a Hard Orgasm When She Got an Anal Fisting for the First Time and Fucked by New Crystal Dildos.

FapHouse 2 weeks ago

First Time Anal Destroying My Ass Using Large Size Dildo

First Time Anal Destroying My Ass Using Large Size Dildo

xHamster 3 years ago

Hardcore Hookup Trans Girl/Girl

65% HD 0:10 / 20:05

Hardcore Hookup Trans Girl/Girl

LoyalFans 2 years ago

Your 1st Trans Tgirl Experience JOI Blonde Russian-Ukranian

Your 1st Trans Tgirl Experience JOI Blonde Russian-Ukranian

Lesbian8 5 months ago

Obedient Slave Fucked Apart

Obedient Slave Fucked Apart

xHamster 1 year ago

Trans Vanessa Gonzo With First Time Double Ana

Trans Vanessa Gonzo With First Time Double Ana

Eporner 3 months ago

TS Girl Kendall Penny Gets Her Ass Pounded

TS Girl Kendall Penny Gets Her Ass Pounded

FetishShrine 3 years ago

Sensational Student Pickup Experience: Rough Sex and Anal Fun with Two Girls and One Trans Friend

Premium HD 42:32

Sensational Student Pickup Experience: Rough Sex and Anal Fun with Two Girls and One Trans Friend

xnxxGold 10 months ago

Teen latina Tgirl first time

Teen latina Tgirl first time

aShemaleTube 14 years ago

Valkyria Domina Shows for First Time Ever Her Naughty Real Life Mistress Skills

73% 0:39 / 24:20

Valkyria Domina Shows for First Time Ever Her Naughty Real Life Mistress Skills

FapHouse 2 years ago

Futanari Lesbians First Date

Futanari Lesbians First Date

Tranny.one 4 years ago

Trans Solo Bliss, Watch Me Play

Trans Solo Bliss, Watch Me Play

FapHouse 5 days ago

Paola Santrelly Loves Monster Cock

Paola Santrelly Loves Monster Cock

xHamster 1 month ago

Luna Atrracted Me With Feet Fetish And Indian Futa With Her Busty Milf Body

Luna Atrracted Me With Feet Fetish And Indian Futa With Her Busty Milf Body

xHamster 2 months ago

Brazilian foot fetish and ts dominates first time Guys do make passes at chicks who wear

Brazilian foot fetish and ts dominates first time Guys do make passes at chicks who wear

Eporner 5 years ago

”ASIANTGIRL - Dennis First Time Showing Her Asian Goodies”

”ASIANTGIRL - Dennis First Time Showing Her Asian Goodies”

Rainblow 1 year ago

Lad has his first time with very hot TS

Lad has his first time with very hot TS

aShemaleTube 14 years ago

”FEMOUT XXX - Angel Monroe First Time To Exposed Her Goodies”

”FEMOUT XXX - Angel Monroe First Time To Exposed Her Goodies”

429Men 5 days ago

supercute brazilian ts thaysa ass destroyed by 2 bbc (pee, dap, ir, balls deep, trans, dirty talk, prolapse)alt002

supercute brazilian ts thaysa ass destroyed by 2 bbc (pee, dap, ir, balls deep, trans, dirty talk, prolapse)alt002

PissVids 4 years ago

My very first time

My very first time

Tranny.one 4 years ago

We met on the street and went home to have sex

We met on the street and went home to have sex

aShemaleTube 1 month ago

”TGIRLPOSTOP - Stacy Miguire Reveals Her Cunt First Time”

”TGIRLPOSTOP - Stacy Miguire Reveals Her Cunt First Time”

IFuckedYourGF 1 year ago

Tgirl Emma Roses first time with a woman

Tgirl Emma Roses first time with a woman

KeekAss 1 year 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

aShemaleTube 7 months ago

TS Slut Milking

59% HD 0:10 / 14:32

TS Slut Milking

LoyalFans 3 months ago

Shocking

Faptor 7 months ago

Very Cute Couple First Time Anal

Very Cute Couple First Time Anal

KeekAss 3 years ago

Finn Is Destroyed by 2 Cocks

54% HD 0:39 / 18:06

Finn Is Destroyed by 2 Cocks

FapHouse 1 year ago

Shemale Ass Fuck Cum

Shemale Ass Fuck Cum

FapHouse 2 days ago

”GROOBYGIRLS - ENJOY THE SUBLIME & STUNNING DREAM DIVYNE SIMPLY AWSOME”

”GROOBYGIRLS - ENJOY THE SUBLIME & STUNNING DREAM DIVYNE SIMPLY AWSOME”

Fapnow 1 year ago

Venus Likes a Three Way

Venus Likes a Three Way

xHamster 3 months ago

Outdoor ass bandit teenager shag photo gay-for-pay guys unsheathed sans registration

Outdoor ass bandit teenager shag photo gay-for-pay guys unsheathed sans registration

MenGem 2 years ago

My first time fuck fine transvestite on upstairs

My first time fuck fine transvestite on upstairs

XXXShemalePorn 2 years ago

trans girl rides huge Goliath from Hankey's Toys

trans girl rides huge Goliath from Hankey's Toys

xHamster 2 years ago

”GROOBYGIRLS - Eris Jolie First Time Hot Performance”

”GROOBYGIRLS - Eris Jolie First Time Hot Performance”

Trashreality 1 year ago

GROOBYGIRLS - Lena Vesper’s Sultry First Time on Cam

GROOBYGIRLS - Lena Vesper’s Sultry First Time on Cam

BallsAndBoobs 5 months ago

Big Cock Shemalec Ass Fuck

Big Cock Shemalec Ass Fuck

FapHouse 1 week ago

”ASIANTGIRL - Blonde & Naughty”

”ASIANTGIRL - Blonde & Naughty”

IFuckedYourGF 2 days ago

Ultra-cute barely legal Yr Senior Teenager TGirl With Monstrous Bum Lures Fellow Into Fuckin Her

Ultra-cute barely legal Yr Senior Teenager TGirl With Monstrous Bum Lures Fellow Into Fuckin Her

Transvids.tv 6 months ago

[Trans] TS Bang BoXXX 6

Premium VR 39:53

[Trans] TS Bang BoXXX 6

VRPorn 9 months ago

Marilyn Johnson first time to blow shemale meaty cock

Marilyn Johnson first time to blow shemale meaty cock

aShemaleTube 3 years ago

first time sucking a shemale cock estela duarte

first time sucking a shemale cock estela duarte

PornOne 3 years ago

Casey and Kat Take Everything Part 1

46% HD 0:12 / 14:15

Casey and Kat Take Everything Part 1

AdultPrime 5 years ago

Horn Demon Busty Ass Got Creampied By Maya

Horn Demon Busty Ass Got Creampied By Maya

xHamster 1 month ago

First Time Sucking A Shemale Cock

First Time Sucking A Shemale Cock

BeMyHole 4 years ago

Casey and Kat Take Everything - Part 1

66% HD 0:12 / 14:10

Casey and Kat Take Everything - Part 1

AdultPrime 5 years ago

Submissive Casey Kisses had her ass stretch by big dick Pierce Paris

Submissive Casey Kisses had her ass stretch by big dick Pierce Paris

Pornicom 11 months ago

Latin tranny fucks pussy for the first time ever

Latin tranny fucks pussy for the first time ever

HD21 5 years ago

”Honeymoon ends with shemale threeway - Khloe Kay , Jayden Marcos , Roman Todd”

”Honeymoon ends with shemale threeway - Khloe Kay , Jayden Marcos , Roman Todd”

TransHero 2 years ago

FIRST TIME CUCKOLD BLOW JOB BIG DICK BBC HUGE FACIAL

FIRST TIME CUCKOLD BLOW JOB BIG DICK BBC HUGE FACIAL

Pornzona 1 week ago

”FEMOUT XXX - Miami Trans Taylor Rose”

”FEMOUT XXX - Miami Trans Taylor Rose”

429Men 2 weeks ago

G064 - Lr Blowjob 10 (jap 2)

G064 - Lr Blowjob 10 (jap 2)

FapHouse 7 months ago

Taking Amethyst's Virginity

HD 0:10 / 30:40

Taking Amethyst's Virginity

LoyalFans 2 weeks ago

GROOBYGIRLS - Eris Jolie First Time Sexy Performance

GROOBYGIRLS - Eris Jolie First Time Sexy Performance

Fapnado 1 year ago

”ASIANTGIRL - Stunning in Every Way”

”ASIANTGIRL - Stunning in Every Way”

StarWank 1 week ago

my first-ever time fucking me with a cucumber in the backside

my first-ever time fucking me with a cucumber in the backside

TrannyGem 4 months 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

Miss me?

xHamster 3 years ago

mother I'd like to fuck Silvana Lee has hardcore sex with her brother's hot tgirl girlfriend Lizzy Laynez

mother I'd like to fuck Silvana Lee has hardcore sex with her brother's hot tgirl girlfriend Lizzy Laynez

BigTitsLust 7 months 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

Two hot TS first time fucking hot woman

Two hot TS first time fucking hot woman

aShemaleTube 2 years ago

Good looking newbie show his big cock to Mea Melone

63% HD 1:01 / 11:31

Good looking newbie show his big cock to Mea Melone

FapHouse 8 years ago

BWC Penetrating A Trans For The First-ever Time (Aurora North)

BWC Penetrating A Trans For The First-ever Time (Aurora North)

KeekAss 1 month ago

TGirls Porn: Luna Breaks In Dani

TGirls Porn: Luna Breaks In Dani

xHamster 3 years ago

Thai t-model attempts BIG BLACK COCK for the first-ever time

Thai t-model attempts BIG BLACK COCK for the first-ever time

TrannyGem 2 years ago

Young Asian ladyboy first time anal sex recorded on amateur video

Young Asian ladyboy first time anal sex recorded on amateur video

Wankoz 2 months ago

Excited shemale and dude screw every other anal out of a cock-sock

Excited shemale and dude screw every other anal out of a cock-sock

ShemaleSin 2 months ago

Riding towards the grande finale

Riding towards the grande finale

xHamster 7 months ago

Dirty Talking Femboy Is Seducing You

66% HD 1:01 / 5:37

Dirty Talking Femboy Is Seducing You

FapHouse 4 months ago

JockPussy: Tommy Tanner plowed by uncut cock Tanner in shower

JockPussy: Tommy Tanner plowed by uncut cock Tanner in shower

GayPorn.video 2 years ago

Valkyria Domme takes on Camilla internal ejaculation and gives her vulva girlcock for the very first time

Valkyria Domme takes on Camilla internal ejaculation and gives her vulva girlcock for the very first time

KeekAss 2 years ago

The party is starting there will be rough sex tonight Clip 1

The party is starting there will be rough sex tonight Clip 1

xHamster 1 month ago

His First Time Ever

64% HD 0:39 / 8:57

His First Time Ever

FapHouse 2 years ago

Beautiful shemale with big thick cock breaks into her ass with tattooed

Beautiful shemale with big thick cock breaks into her ass with tattooed

xHamster 1 month ago

TGIRLSHOOKUP: Fuck Me Like I'm Trash!

TGIRLSHOOKUP: Fuck Me Like I'm Trash!

xHamster 2 years ago

Busty teen sheshaft first time takes big cock

Busty teen sheshaft first time takes big cock

ALOTPorn 5 years ago

Sweaty Slutty Blonde Girl Gripping On Transgender Girl Cock While They Kiss, Petite Teen Nurse Cowgirl Fucking Trans Girl Cock With Her Pussy Exposed, Anal Fucking A Transgender, AI Generated

Sweaty Slutty Blonde Girl Gripping On Transgender Girl Cock While They Kiss, Petite Teen Nurse Cowgirl Fucking Trans Girl Cock With Her Pussy Exposed, Anal Fucking A Transgender, AI Generated

W1mp 5 days ago

Japanese amateur Miwa Ichikawa shows us her huge boobs and nipples

61% HD 1:01 / 56:24

Japanese amateur Miwa Ichikawa shows us her huge boobs and nipples

FapHouse 3 years ago

16 17 18 19 20

23,014 results found

Related searches

Narrow your search

trans fucks guy first time

Categories Pornstars

Categories Pornstars

Legal

Terms of Service Privacy Statement Statement of Responsibility Notice and Action Policy (Link Removal) DMCA / Copyright Acceptable Content Policy Digital Services Act 2257

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.