First Time Ever Videos (2,344)

Watch this hot shemale dominate her own cock live on webcam for the first time ever!

Watch this hot shemale dominate her own cock live on webcam for the first time ever!

FetishShrine 8 months ago

I Instructed Him How To Gobble Vag For The First-ever Time!

I Instructed Him How To Gobble Vag For The First-ever Time!

Gayhub 8 months ago

Bottoming Never Felt so Good

Bottoming Never Felt so Good

XHamster 10 months ago

”Ultra Tightenthe Ass with HUGE Dildo!”

”Ultra Tightenthe Ass with HUGE Dildo!”

LesbianBliss 7 months ago

First-Ever time self restrain bondage with keys~

First-Ever time self restrain bondage with keys~

TrannyGem 8 months ago

I’ll Turn You Into My Sissy Slut!

HD 0:39 / 15:06

I’ll Turn You Into My Sissy Slut!

FapHouse 7 months ago

”Straight Latino fucks a man hole first time ever”

”Straight Latino fucks a man hole first time ever”

TransHero 7 months ago

”Asian brunette is about to fuck a ebony dude”

”Asian brunette is about to fuck a ebony dude”

TransHero 7 months ago

An Unusual Class

An Unusual Class

Some.Porn 10 months ago

Shy Shower

57% HD 0:10 / 2:11

LoyalFans 4 months ago

Check Out Fetishize Naked Femboy's Desert Seduction by Horny Troops - the Greatest XXX Porn Around!

Check Out Fetishize Naked Femboy's Desert Seduction by Horny Troops - the Greatest XXX Porn Around!

FapHouse 4 months ago

Fantastic First-time XXX: Transvestite Femboy's Ass-centric Glory Hole Cumshot!

Fantastic First-time XXX: Transvestite Femboy's Ass-centric Glory Hole Cumshot!

XHamster 3 months ago

Our First Footjob - Tgirl Fucks Highly Arched Soles

HD 1:01 / 18:41

Our First Footjob - Tgirl Fucks Highly Arched Soles

FapHouse 2 months ago

Sumptuous Trans Stunner Anal invasion Her Best friend For The First-ever Time

Sumptuous Trans Stunner Anal invasion Her Best friend For The First-ever Time

TrannyGem 2 months ago

ladyboystar - perhaps the hottest fuck i ve had with a ladyboy ever!

HD 0:30 / 32:59

ladyboystar - perhaps the hottest fuck i ve had with a ladyboy ever!

AnalVids 1 month ago

Ladyboystar - Perhaps the hottest fuck I&#039_ve had with a ladyboy ever!

Premium HD 33:00

Ladyboystar - Perhaps the hottest fuck I&#039_ve had with a ladyboy ever!

XVideosRed 1 month ago

Sissy Stagecoach in the Wild West

Sissy Stagecoach in the Wild West

XHamster 2 months ago

Miss Hannah Blake Mistress Ae & Jasmine d’light extreme fisting & pegging

4K 0:27 / 16:42

Miss Hannah Blake Mistress Ae & Jasmine d’light extreme fisting & pegging

Clips4sale 10 months ago

Check Out the Very First Masturbation Video I Ever Recorded! I Think I Need to Make More of These

HD 0:39 / 12:17

Check Out the Very First Masturbation Video I Ever Recorded! I Think I Need to Make More of These

FapHouse 9 months ago

Lizzy Woo's Ass Wrecked First-time Strap-on Pegging by Your Cruel Stepmommy Domme Watch Her Beg for More

Lizzy Woo's Ass Wrecked First-time Strap-on Pegging by Your Cruel Stepmommy Domme Watch Her Beg for More

XHamster 2 months ago

Ladyboystar - Sexiest Ladyboy Ever Takes My Pants Down and Sucks on My Cock

Ladyboystar - Sexiest Ladyboy Ever Takes My Pants Down and Sucks on My Cock

XHamster 2 months ago

It’s Lovely & Warm in There - Her First Fisting Featuring Jasmine Dlight & Mistress Prin

It’s Lovely & Warm in There - Her First Fisting Featuring Jasmine Dlight & Mistress Prin

FapHouse 7 months ago

”First time babe shooting porn has the biggest most amazing butt ever”

”First time babe shooting porn has the biggest most amazing butt ever”

TransHero 7 months ago

”Jacrony's son succumbed to Agatha's sultry charms. Satisfying pornographic star Ag”

”Jacrony's son succumbed to Agatha's sultry charms. Satisfying pornographic star Ag”

TransHero 7 months ago

A Gonzo Good Time

A Gonzo Good Time

Clips4sale 3 years ago

Pristine Edge first time to fuck by a trans Kate Zoha

Pristine Edge first time to fuck by a trans Kate Zoha

SleazyNEasy 3 years ago

Taking a giant leap into passion & femininity

Taking a giant leap into passion & femininity

FapHouse 3 years ago

Kellycd2022 very first time ever clad flick pissing in undies and stocking tugging money-shot

Kellycd2022 very first time ever clad flick pissing in undies and stocking tugging money-shot

KeekAss 3 years ago

Transgender sits astride fuck stick and cowers. First-Ever climax

Transgender sits astride fuck stick and cowers. First-Ever climax

TrannyGem 3 years ago

FTM see me make myself squirt for the first-ever-ever time !

FTM see me make myself squirt for the first-ever-ever time !

Transvids.tv 1 year ago

BIMBOFICATION 101

BIMBOFICATION 101

LoyalFans 2 years ago

Indian Sissy Slut Spanks Her Plugged Ass and Plays with Her Tiny Clitty

Indian Sissy Slut Spanks Her Plugged Ass and Plays with Her Tiny Clitty

XHamster 2 years ago

”ASIANTGIRL - Nid's First Time Solo Masturbation Video”

”ASIANTGIRL - Nid's First Time Solo Masturbation Video”

Rainblow 1 year ago

Youthfull Trans MILF Plays With Herself for the First-ever-ever Time

Youthfull Trans MILF Plays With Herself for the First-ever-ever Time

TransTube.tv 1 year ago

Sissy Anal Training Instructions - Fuck your Ass with Me SD wmv

Sissy Anal Training Instructions - Fuck your Ass with Me SD wmv

Clips4sale 2 years ago

First-ever-ever time taking giant Manbearpig large 15 inch fake-man sausage in my backside makes me jizz two times

First-ever-ever time taking giant Manbearpig large 15 inch fake-man sausage in my backside makes me jizz two times

TransTube.tv 1 year ago

”Prostate Epiphany - Whitney Wright, Erica Cherry”

”Prostate Epiphany - Whitney Wright, Erica Cherry”

Rainblow 2 years ago

”A Natural”

”A Natural”

ThePornstar 2 years ago

Boobs Blessed

Some.Porn 1 year ago

Office whore fisting very first-ever time

Office whore fisting very first-ever time

Transvids.tv 1 year ago

first-ever time bathroom have fun

first-ever time bathroom have fun

TrannyGem 1 year ago

New Girl Jodie Sevendee Agrees to Self Bondage

49% 0:30 / 9:24

New Girl Jodie Sevendee Agrees to Self Bondage

Clips4sale 1 year ago

Ember Snow- TS BGG "Threesome Fuck w Leilani Li and Andre Stone"

Ember Snow- TS BGG "Threesome Fuck w Leilani Li and Andre Stone"

Clips4sale 2 years ago

POINT OF VIEW: Humping a jaw-dropping Trans nymph for the first-ever time

POINT OF VIEW: Humping a jaw-dropping Trans nymph for the first-ever time

TrannyGem 1 year ago

FIRST TIME ANAL! Ass Fucked by Trans Girl

Premium HD 16:57

FIRST TIME ANAL! Ass Fucked by Trans Girl

Sheer 4 years ago

ASIANTGIRL - All About Beauty

ASIANTGIRL - All About Beauty

Fapnado 1 year ago

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

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

FapHouse 11 months ago

beauty Attempts To poke With Trans First-ever Time

beauty Attempts To poke With Trans First-ever Time

Transvids.tv 1 year ago

FEMOUT GONZO - Sable First-ever Time Peek Of Her Sweetness

FEMOUT GONZO - Sable First-ever Time Peek Of Her Sweetness

KeekAss 1 year ago

JockPussy - FTM Ari demonstrates first-ever timer how to sate his puss

JockPussy - FTM Ari demonstrates first-ever timer how to sate his puss

GayCK 4 years ago

Futa Alien Goddess ravages BIG BLACK COCK Earthling for the first-ever time.

Futa Alien Goddess ravages BIG BLACK COCK Earthling for the first-ever time.

KeekAss 4 years ago

Trans Tori Easton fucks BBW Natasha Nice in cottage

Trans Tori Easton fucks BBW Natasha Nice in cottage

Sheshaft 4 years ago

The first-ever time of Carolina

The first-ever time of Carolina

TrannyGem 5 years ago

Mature ebony shemale nymph screw youthfull milky stud first-ever time

Mature ebony shemale nymph screw youthfull milky stud first-ever time

TrannyGem 5 years ago

Shy First ever Orgasm Crossdressing (Preview)

Shy First ever Orgasm Crossdressing (Preview)

XHamster 5 years ago

Gothic crossdresser teenage first-ever time toying with faux-cock and nutting all over herself

Gothic crossdresser teenage first-ever time toying with faux-cock and nutting all over herself

KeekAss 4 years ago

I was romped by a trans nymph for the first-ever time

I was romped by a trans nymph for the first-ever time

KeekAss 4 years ago

FEMOUT: Ms. Momo's First-Ever Time

FEMOUT: Ms. Momo's First-Ever Time

KeekAss 4 years ago

tiny sissy rails a faux-cock for first-ever time

tiny sissy rails a faux-cock for first-ever time

TrannyGem 4 years ago

Pristine Edge first time to fuck by a trans Kate Zoha

Pristine Edge first time to fuck by a trans Kate Zoha

Pornwhite 3 years ago

Shemale Amy Drills Boys Donk For The First-Ever Time

Shemale Amy Drills Boys Donk For The First-Ever Time

TrannyGem 3 years ago

DEMONS TGIRLS - Marvelous Marilyn Johnson Expert Bang-Out With A Trans Gal For The First-Ever Time

DEMONS TGIRLS - Marvelous Marilyn Johnson Expert Bang-Out With A Trans Gal For The First-Ever Time

KeekAss 3 years ago

T-Girls first-ever time with ebony dude

T-Girls first-ever time with ebony dude

KeekAss 7 years ago

FTM Bro Fucking with Atlas Adventure 5

HD 0:11 / 35:31

FTM Bro Fucking with Atlas Adventure 5

Clips4sale 4 years ago

Asian crossdresser milks off for the first-ever time in two weeks

Asian crossdresser milks off for the first-ever time in two weeks

KeekAss 4 years ago

Tranny for first-ever Time Intercourse - Kimcock

Tranny for first-ever Time Intercourse - Kimcock

TrannyGem 7 years ago

AUBREY'S FIRST-EVER TIME

AUBREY'S FIRST-EVER TIME

TrannyGem 6 years ago

Yago Rebeiro cum plowed Dani

Yago Rebeiro cum plowed Dani

Tranny.one 5 years ago

First-Ever Time with Anthony - Bad Dragon Fuck Stick

First-Ever Time with Anthony - Bad Dragon Fuck Stick

TrannyGem 4 years ago

LEO BULGARI POUNDS FOR THE FIRST-EVER TIME WITH A TRANS FELLOW (FTM) VICTOR DEEX - TEASER!!!

LEO BULGARI POUNDS FOR THE FIRST-EVER TIME WITH A TRANS FELLOW (FTM) VICTOR DEEX - TEASER!!!

KeekAss 3 years ago

”TRANSVR: Taste-O-Vision!”

”TRANSVR: Taste-O-Vision!”

Fapnow 2 years ago

Beautiful BIG BLACK COCK pummels a stellar tranny for the first-ever time

Beautiful BIG BLACK COCK pummels a stellar tranny for the first-ever time

TrannyGem 3 years ago

Journalist interviews trans couple, Jane's fresh perspective.

Journalist interviews trans couple, Jane's fresh perspective.

Fapnado 3 years ago

new cam software had to try idk....

new cam software had to try idk....

XHamster 2 years ago

”Journalist interviews tbabe couple, Jane's fresh perspective.”

”Journalist interviews tbabe couple, Jane's fresh perspective.”

TransHero 3 years ago

Eroused tranny mounts a penis

Eroused tranny mounts a penis

XXXShemalePorn 5 years ago

Femboy rails 7 inch fake penis for first-ever time

Femboy rails 7 inch fake penis for first-ever time

TrannyGem 2 years ago

”Hot shemale, TS Foxxy fucks big boobed sexy girl, Aiden Starr”

”Hot shemale, TS Foxxy fucks big boobed sexy girl, Aiden Starr”

4Wank 2 years ago

Having a Xxl Egg!!

Having a Xxl Egg!!

FapHouse 2 years ago

elisa afrodit first porn ever and creampie

elisa afrodit first porn ever and creampie

PornBox 1 year ago

Toxin Vagina

Some.Porn 1 year ago

19yo Latina Transsexual Eventually Bangs High College Kick for First-Ever Time - HE WAS DIGGING

19yo Latina Transsexual Eventually Bangs High College Kick for First-Ever Time - HE WAS DIGGING

TrannyGem 1 year ago

Sylvia deepthroats muscle man dick for first-ever time

Sylvia deepthroats muscle man dick for first-ever time

TrannyGem 1 year ago

BBC Forever Faggot

BBC Forever Faggot

Clips4sale 2 years ago

Trans nymph Attempting monster fuck stick for the first-ever time and getting her slot ruined but a huge jizz shot

Trans nymph Attempting monster fuck stick for the first-ever time and getting her slot ruined but a huge jizz shot

Transvids.tv 1 year ago

Latin Tranny Fucks Pussy for the First Time EVER

Latin Tranny Fucks Pussy for the First Time EVER

YouPorn Unknown

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

FapHouse 1 year ago

First-ever Time with Pad in Underpants - Antique Amateur Crossdresser Joy!

First-ever Time with Pad in Underpants - Antique Amateur Crossdresser Joy!

GayCK 1 year ago

ASIANTGIRL - Nid's First-ever Time Solo Onanism Vid

ASIANTGIRL - Nid's First-ever Time Solo Onanism Vid

KeekAss 1 year ago

Sissy Supergirl Super Compilation

Sissy Supergirl Super Compilation

XHamster 11 months ago

Best First Date Ever Casey Calvert Gobbles Up T-Chick Leilani Li Takes Deep Creampie

Best First Date Ever Casey Calvert Gobbles Up T-Chick Leilani Li Takes Deep Creampie

Xshemale 1 year ago

Alysons First Shoot with Thad Maxxx

66% HD 1:01 / 13:27

Alysons First Shoot with Thad Maxxx

FapHouse 1 year ago

Transwoman Erica Cherry jerked herself to jizz in a heavy and deep anal fuck with Whitney Wright

Transwoman Erica Cherry jerked herself to jizz in a heavy and deep anal fuck with Whitney Wright

Sheshaft 1 year ago

Virgin Sissy Housewife Fucked with Dildo for the First Time

Virgin Sissy Housewife Fucked with Dildo for the First Time

FapHouse 1 year ago

My first-ever time with a t-model

My first-ever time with a t-model

KeekAss 1 year ago

teenie crossdresser humped and spread first-ever time

teenie crossdresser humped and spread first-ever time

KeekAss 1 year ago

T-model very first-ever time with bang-festival lady

T-model very first-ever time with bang-festival lady

TransTube.tv 1 year ago

Mechanic and his very first-ever time with trans

Mechanic and his very first-ever time with trans

TransTube.tv 1 year ago

Busty teen sheshaft first time takes big cock

Busty teen sheshaft first time takes big cock

AShemaleTube 5 years ago

Curly lightskin Teenage trans very first-ever time on camera extremely crazy

Curly lightskin Teenage trans very first-ever time on camera extremely crazy

TransTube.tv 1 year ago

I want a guy with a yam-sized spear to screw my backside for the first-ever time relentless

I want a guy with a yam-sized spear to screw my backside for the first-ever time relentless

TransTube.tv 1 year ago

Chinese She-masculine's First-ever-ever Time Getting Plumbed By A Dude on Cam

Chinese She-masculine's First-ever-ever Time Getting Plumbed By A Dude on Cam

TransTube.tv 1 year ago

The first-ever time the nymph banged a cooter, was it a girl-on-girl?

The first-ever time the nymph banged a cooter, was it a girl-on-girl?

KeekAss 1 year ago

Crossdressers First-Ever Time

Crossdressers First-Ever Time

4Gay 2 years ago

Bubblebutt Play with Natural Light

HD 0:39 / 15:03

Bubblebutt Play with Natural Light

FapHouse 2 years ago

CLEO CADILLAC first-ever time a trans licked my arse

CLEO CADILLAC first-ever time a trans licked my arse

KeekAss 1 year ago

Her Chastity Cage Flops Around While Her Asshole is Stretched Beyond Recognition!

Her Chastity Cage Flops Around While Her Asshole is Stretched Beyond Recognition!

XHamster 1 year ago

The Training of Jamie Taylor

The Training of Jamie Taylor

XHamster 8 years ago

Teenager fellow penetrates transgender princess first-ever time

Teenager fellow penetrates transgender princess first-ever time

GayCK 7 years ago

Huge-Boobed Ash-Blonde TRANSSEXUAL Kayleigh Coxx first-ever time tearing up a fuckbox

Huge-Boobed Ash-Blonde TRANSSEXUAL Kayleigh Coxx first-ever time tearing up a fuckbox

TrannyGem 7 years ago

Your first-ever time with a tranny is going to be magical

Your first-ever time with a tranny is going to be magical

TrannyGem 6 years ago

Without wig androgynous - Hygiene an maturity m

Without wig androgynous - Hygiene an maturity m

XHamster 4 years ago

Mc young actor romping a transgirl for the first-ever time

Mc young actor romping a transgirl for the first-ever time

TrannyGem 4 years ago

”Nadia : Horny Suck Doll”

”Nadia : Horny Suck Doll”

TransHero 6 years ago

Is this your first time in a shemale gangbang

Is this your first time in a shemale gangbang

XHamster 9 years ago

Brunette asian ladyboy bareback fucked for first time

Brunette asian ladyboy bareback fucked for first time

Sheshaft 8 years ago

Its my first-ever time letting a shemale rail my penis

Its my first-ever time letting a shemale rail my penis

KeekAss 5 years ago

Tranny Fucks Pussy for the first time Ever

Tranny Fucks Pussy for the first time Ever

XHamster 14 years ago

TS Bruna Butterfly Hot Gangbang

TS Bruna Butterfly Hot Gangbang

XHamster 10 years ago

Sinful Jane Wilde and Aften Opal at masturbation scene

Sinful Jane Wilde and Aften Opal at masturbation scene

PornHat 3 years ago

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