First Time Trans Videos (28,913)

Petra,s 8th training

Petra,s 8th training

xHamster 1 year ago

First teen anal experience with an impromptu toy, he dreams of a huge cock in his posh ass

First teen anal experience with an impromptu toy, he dreams of a huge cock in his posh ass

xHamster 3 years ago

Shemale Girl Fucking 18 Plus Boy Mouth With Big Cock Under The Table

Shemale Girl Fucking 18 Plus Boy Mouth With Big Cock Under The Table

xHamster 3 weeks ago

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

65% HD 1:01 / 14:59

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

FapHouse 1 year ago

”We had a first time threeway with a tranny female”

”We had a first time threeway with a tranny female”

Fapnow 3 years ago

My Internet Friend Has Sex For The First Time With A Trans Girl And His Femboy Friend Gets All His Cum In His Face

My Internet Friend Has Sex For The First Time With A Trans Girl And His Femboy Friend Gets All His Cum In His Face

getTranny 1 month ago

[Trans] Measure Me

VR 1:20 / 30:26

[Trans] Measure Me

VRPorn 2 years ago

I Get My Milk with a Toy Mouth and You Won't Believe the Amount of Cum That Came Out

I Get My Milk with a Toy Mouth and You Won't Believe the Amount of Cum That Came Out

FapHouse 2 months ago

first time fisting in tight white ass of teen tranny

first time fisting in tight white ass of teen tranny

Pornzona 2 months ago

His First Taste of Cum

67% HD 0:10 / 8:03

His First Taste of Cum

LoyalFans 3 months ago

Delicious Blonde with Pink Ass Ready to Get Fucked

Delicious Blonde with Pink Ass Ready to Get Fucked

FapHouse 2 months ago

A Very Hot Christmas with My Sex Machine

A Very Hot Christmas with My Sex Machine

FapHouse 3 months ago

This Video Is the 1st in a Series of Nyxi Leon's Very First Transformation Ever

45% HD 0:39 / 25:41

This Video Is the 1st in a Series of Nyxi Leon's Very First Transformation Ever

FapHouse 1 year ago

free femboy fucks his stepfather

free femboy fucks his stepfather

aShemaleTube 3 months ago

She Takes a Shower with a Cis Woman

She Takes a Shower with a Cis Woman

xHamster 10 months ago

Amateur Brunette Tgirls First Time Anal Fucked by Big Cocks

Amateur Brunette Tgirls First Time Anal Fucked by Big Cocks

WeGotDicks 2 months ago

My First Time Anal

My First Time Anal

Pornzona 2 months ago

Femboy Gets Fucked Bareback by Hetero

53% HD 1:01 / 21:52

Femboy Gets Fucked Bareback by Hetero

FapHouse 3 months ago

Femboy's Hot Ass Is Detonated by Huge Showy Dildo

Femboy's Hot Ass Is Detonated by Huge Showy Dildo

FapHouse 3 months ago

Greedy Slut Intense Deepthroat Hot Ass & Thick Cum Swallowing

61% HD 0:39 / 1:42

Greedy Slut Intense Deepthroat Hot Ass & Thick Cum Swallowing

FapHouse 2 weeks ago

Young Trans Beauty Gives Older Man His First Trans Experience

Young Trans Beauty Gives Older Man His First Trans Experience

xHamster 3 months ago

My Black Chauffeur with Huge Cock Fucks My Ass While I'm Lying on My Bed

54% 0:39 / 29:27

My Black Chauffeur with Huge Cock Fucks My Ass While I'm Lying on My Bed

FapHouse 3 months ago

Vol #4: Fucked For The first Time on Femout

Vol #4: Fucked For The first Time on Femout

Dafreeporn 9 months ago

Shy Golden Shower

63% HD 0:39 / 2:16

Shy Golden Shower

FapHouse 2 months ago

Gfe First Machine Fuck

Gfe First Machine Fuck

xHamster 1 year ago

Cute Asian Teen Pleases Hot Guy

Cute Asian Teen Pleases Hot Guy

xHamster 1 month ago

G117 - Lola Deepthroating a Long White Dick 1 - Original

G117 - Lola Deepthroating a Long White Dick 1 - Original

FapHouse 1 month ago

First Time Trans Alice Gets Wrecked

63% 0:39 / 43:33

First Time Trans Alice Gets Wrecked

FapHouse 8 months ago

Cutiepii33quinn Gets Her Cherry Arse Nailed For Very First Time

Cutiepii33quinn Gets Her Cherry Arse Nailed For Very First Time

PePorn 7 months ago

Fucking and Getting Pregnant My Fucktoy Ass, Having so Much Fun While Asking for More

57% HD 1:01 / 8:55

Fucking and Getting Pregnant My Fucktoy Ass, Having so Much Fun While Asking for More

FapHouse 1 month ago

Anime Shemale Girls Enjoying sex

Anime Shemale Girls Enjoying sex

xHamster 3 days ago

This Fit Trans Came to Cause Mischief on the City Streets on Her Birthday

This Fit Trans Came to Cause Mischief on the City Streets on Her Birthday

aShemaleTube 2 months ago

GROOBYGIRLS: Bella Sky Graduates

GROOBYGIRLS: Bella Sky Graduates

xHamster 2 years ago

Ive never been with a trans girl before but I am down for it

Ive never been with a trans girl before but I am down for it

FetishShrine 1 month ago

Melissa Masters - Your Very First Time Trans Femdom GFE

Melissa Masters - Your Very First Time Trans Femdom GFE

IcePorn 5 months ago

Sereia Mel sendo fodida de todo jeito

Premium HD 15:52

Sereia Mel sendo fodida de todo jeito

XVideosRed 2 years ago

She Cums so Hard When She Gets Spanked and Fucked

63% HD 1:01 / 21:00

She Cums so Hard When She Gets Spanked and Fucked

FapHouse 1 week ago

Eva Turned a Top Guy Into a Bottom

54% HD 1:01 / 16:41

Eva Turned a Top Guy Into a Bottom

FapHouse 2 months ago

Bts POV Sex with Anahi Altuzar 2

Bts POV Sex with Anahi Altuzar 2

FapHouse 2 weeks ago

”TGIRLSHOOKUP - America's Sluttiest Hole”

”TGIRLSHOOKUP - America's Sluttiest Hole”

Faptor 3 weeks ago

My First Sextape with a Hung Tgirl

58% HD 0:39 / 42:44

My First Sextape with a Hung Tgirl

FapHouse 2 months ago

French boy took all my load

61% HD 0:10 / 9:19

French boy took all my load

LoyalFans 7 months ago

I Fucked My Wife's Tranny Friend's Untouched Ass for the First Time!

I Fucked My Wife's Tranny Friend's Untouched Ass for the First Time!

XXXShake 1 year ago

My very first time HOOKUP with a trans lady !!

My very first time HOOKUP with a trans lady !!

MyTransfix 2 days ago

White man experiences trans booty for the first time

White man experiences trans booty for the first time

XXXShemalePorn 1 year ago

She Is Pretty Trans Woman For Real

She Is Pretty Trans Woman For Real

Eporner 2 months ago

Cum Challenge! Who Comes First???

71% HD 0:39 / 4:12

Cum Challenge! Who Comes First???

FapHouse 2 years ago

Also Hawt to Handle in Denmark

Also Hawt to Handle in Denmark

ShemaleSin 3 years ago

Who Wants to Eat My Cum Next

63% HD 1:01 / 24:58

Who Wants to Eat My Cum Next

FapHouse 3 months ago

ABT250116 20cm Dildo Challenge

ABT250116 20cm Dildo Challenge

xHamster 1 month ago

Tiny thai ladyboy room maid barely can handle a big cock fucking her roughly

Tiny thai ladyboy room maid barely can handle a big cock fucking her roughly

xHamster 10 months ago

Barely 18 Extreme Throat Fucking

Barely 18 Extreme Throat Fucking

xHamster 1 month ago

TransXHunter - Part II Trans Big cock fucking a guys ass with her cute Pink Banny costume. and give her a good blowjob

TransXHunter - Part II Trans Big cock fucking a guys ass with her cute Pink Banny costume. and give her a good blowjob

xHamster 2 months ago

FTM Jaq Quicksilver Fucked By Big Dicked Trans Babe

FTM Jaq Quicksilver Fucked By Big Dicked Trans Babe

xHamster 1 month ago

A TRANNY girl with a monster dick is sitting on your face and milking herself

A TRANNY girl with a monster dick is sitting on your face and milking herself

xHamster 1 week ago

Young Guy Fucks Blonde Latin Shemale Anal for the First Time

Young Guy Fucks Blonde Latin Shemale Anal for the First Time

xHamster 5 months ago

Petite Asian trans woman loves a cock in her asshole

Petite Asian trans woman loves a cock in her asshole

aShemaleTube 6 days ago

Busty TS Pounds Away, Blasts a Huge Load & Tastes Her Warm Cum (4k)

63% 4K 0:10 / 24:40

Busty TS Pounds Away, Blasts a Huge Load & Tastes Her Warm Cum (4k)

LoyalFans 4 months ago

gina james and vera special when transgirl met transgirl

gina james and vera special when transgirl met transgirl

TransDoe 2 years ago

Stepbrother let me eat your cock for first time

Stepbrother let me eat your cock for first time

FetishShrine 1 month ago

Taking my bestie to have some supreme orgy with a trans gal for the very first time, NO HAIR

Taking my bestie to have some supreme orgy with a trans gal for the very first time, NO HAIR

TrannyGem 6 days ago

Gfe First Machine Fuck

Gfe First Machine Fuck

xHamster 1 year ago

skinny tranny is interviewed and sensually barebacked in first scene

skinny tranny is interviewed and sensually barebacked in first scene

PornOne 4 days ago

”Lustful Spanish lesbian sucks off her twat”

”Lustful Spanish lesbian sucks off her twat”

ThePornstar 11 months ago

Very first-ever time with trans in gloryhole trio-way

Very first-ever time with trans in gloryhole trio-way

TransTube.tv 1 year ago

FEMOUT XXX - First Time Black Teen petite Tgirl masturbates

FEMOUT XXX - First Time Black Teen petite Tgirl masturbates

xHamster 2 years ago

Avery Angel's first time as a couple: A wild, steamy threesome with a pawg MILF and two bi guys!

Avery Angel's first time as a couple: A wild, steamy threesome with a pawg MILF and two bi guys!

TrannyMovs 7 months ago

First Time With A Shemale

First Time With A Shemale

Tranny.one 4 years ago

Anastasia Penny In Hired Escort To Get Fucked For The First Time

Anastasia Penny In Hired Escort To Get Fucked For The First Time

AbTranny 8 months ago

Petite Mexican FTM Teen Ass Ripped By Fat Toy Gushing Cum Explosion

Petite Mexican FTM Teen Ass Ripped By Fat Toy Gushing Cum Explosion

JuicyTrans 1 week ago

TS Fuck My Pussy

59% 0:39 / 4:28

TS Fuck My Pussy

FapHouse 1 month ago

My first time dominated by a hot blonde tranny - raw, rough, and cum-filled!

My first time dominated by a hot blonde tranny - raw, rough, and cum-filled!

TrannyMovs 6 months ago

Leopard corset

xHamster 2 months ago

My brother-in-law came to visit and I ended up having sex with him while my husband was away -

My brother-in-law came to visit and I ended up having sex with him while my husband was away -

aShemaleTube 1 month ago

StepBro Fucks my Pussy Raw TransBoySecret

StepBro Fucks my Pussy Raw TransBoySecret

BoyFriendTV 1 year ago

Hot MILF wanted to have a fight, but I fucked her well (143)

Hot MILF wanted to have a fight, but I fucked her well (143)

Eporner 4 years ago

I fuck her ass with desire

I fuck her ass with desire

xHamster 5 months ago

My Black Chauffeur with Huge Cock Fucks My Ass While I'm Lying on My Bed

61% 1:01 / 29:27

My Black Chauffeur with Huge Cock Fucks My Ass While I'm Lying on My Bed

FapHouse 3 months ago

Freya Frostnymph frotting for the first time

Freya Frostnymph frotting for the first time

xHamster 1 year ago

Step Brother Fucks Shemale Yasmin in Her Tight Asshole for the First Time

Step Brother Fucks Shemale Yasmin in Her Tight Asshole for the First Time

xHamster 8 months ago

Savage Anal Hardcore Pounding Without Remorse

61% 1:01 / 11:13

Savage Anal Hardcore Pounding Without Remorse

FapHouse 1 month ago

”ASIANTGIRL - Sweet & Hung”

”ASIANTGIRL - Sweet & Hung”

LesbianBliss 2 months ago

Hot Trans Cumshot compilation

Hot Trans Cumshot compilation

xHamster 1 week ago

TS Goddess Creampies the Virgin Bell Boy

67% HD 0:10 / 15:06

TS Goddess Creampies the Virgin Bell Boy

LoyalFans 2 months ago

Indian Shemale Hardcore Fun with BF

58% HD 0:39 / 6:14

Indian Shemale Hardcore Fun with BF

FapHouse 1 month ago

We Did an Interracial Threesome for the First Time with My Best Friend BBC

We Did an Interracial Threesome for the First Time with My Best Friend BBC

aShemaleTube 1 month ago

Thirsty College boy

67% HD 0:10 / 12:26

Thirsty College boy

LoyalFans 1 year ago

Thick Ass Taking Every Inch of Girl Cock

66% HD 1:01 / 17:15

Thick Ass Taking Every Inch of Girl Cock

FapHouse 4 weeks ago

Discovering The Perfect Asian Sissy Summer

Discovering The Perfect Asian Sissy Summer

Eporner 8 months ago

Sissy precum for the first time

Sissy precum for the first time

xHamster 8 months ago

Shemale teen first time bareback

Shemale teen first time bareback

aShemaleTube 8 years ago

Speed Dating Fever Janet and Ash Explore Taboo Trans Cock Oral Fun Virgin First Time Experience

Speed Dating Fever Janet and Ash Explore Taboo Trans Cock Oral Fun Virgin First Time Experience

Yeswegays 1 week ago

T-girl Tea Party with Nightsisterlil1 Threesome, Anal, Ass Eating, Creampie and Facial

T-girl Tea Party with Nightsisterlil1 Threesome, Anal, Ass Eating, Creampie and Facial

xHamster 1 year ago

TS Slut Milking

59% HD 0:10 / 14:32

TS Slut Milking

LoyalFans 7 months ago

Agatha Lira - My Very first Time With A Trans And The First-ever Time

Agatha Lira - My Very first Time With A Trans And The First-ever Time

Transvids.tv 1 year ago

First Time Ts Fucker Gets Epic Dicking With Lea Vibing

First Time Ts Fucker Gets Epic Dicking With Lea Vibing

AbTranny 2 months ago

Your Very first Time Getting Drilled by a Trans Chick: Very first Rendezvous GFE POINT OF VIEW Female dominance

Your Very first Time Getting Drilled by a Trans Chick: Very first Rendezvous GFE POINT OF VIEW Female dominance

TransTube.tv 11 months ago

sexy tranny fanny menezes takes two cocks in the ass for the first time 1080p

sexy tranny fanny menezes takes two cocks in the ass for the first time 1080p

PornOne 2 years ago

Transsexual cums at a practitioner's appointment

Transsexual cums at a practitioner's appointment

xHamster 3 months ago

Sexy Beautiful Bigtits Big Cock Ladyboy Fucks with Big Ass Pornstar

Sexy Beautiful Bigtits Big Cock Ladyboy Fucks with Big Ass Pornstar

xHamster 1 month ago

Tranny cum swallow first time Mirta in love with her boyfrie

Tranny cum swallow first time Mirta in love with her boyfrie

VipTube 10 years ago

Young german amateur transexual teen shemale fucks first time anal with huge cock

Young german amateur transexual teen shemale fucks first time anal with huge cock

Tranny.one 3 years ago

I Gave My Boy a Blowjob While He Was Looking at His Cell Phone, the Atmosphere Heated up and He Ended up Fucking My Ass

I Gave My Boy a Blowjob While He Was Looking at His Cell Phone, the Atmosphere Heated up and He Ended up Fucking My Ass

xHamster 3 months ago

My Little Transgender College Girl Calls Me Stepdaddy

66% HD 1:01 / 21:26

My Little Transgender College Girl Calls Me Stepdaddy

FapHouse 4 months ago

Femboys getting naughty at the public douche, frottingbing and doing raw fellatios on each other

Femboys getting naughty at the public douche, frottingbing and doing raw fellatios on each other

TrannyGem 1 month ago

Sissyboy Cuckold Slave Training Pegging First Time

Sissyboy Cuckold Slave Training Pegging First Time

xHamster 3 months ago

Being used for this Russian daddy

Being used for this Russian daddy

xHamster 4 days ago

Olivia Jay Leads Kasey Kei Into Slow Sensual Sex

Olivia Jay Leads Kasey Kei Into Slow Sensual Sex

FetishShrine 8 months ago

4 Wonderful Tranny Scenes

4 Wonderful Tranny Scenes

xHamster 2 years ago

Jesse, a newbie, gets her first time in underpants with a fuck stick - a hot compilation!

Jesse, a newbie, gets her first time in underpants with a fuck stick - a hot compilation!

TrannyMovs 1 week ago

So It's Your First Time With A Trans Woman

So It's Your First Time With A Trans Woman

Eporner 2 years ago

Trans fucking a straight boy for the first time

Trans fucking a straight boy for the first time

Pornzona 2 months ago

Pink barbie shemale vacation anal beach sex anal creampie AI Generated

Pink barbie shemale vacation anal beach sex anal creampie AI Generated

xHamster 1 week ago

Ai Generated Long Dick Ebony Shemale Creampie Cum and Threesome.

Ai Generated Long Dick Ebony Shemale Creampie Cum and Threesome.

xHamster 1 month ago

My Slutty Teen Stepsister is Begging to Ride Her Stepbrother's Dick

My Slutty Teen Stepsister is Begging to Ride Her Stepbrother's Dick

Tranny.one 11 months ago

First Transsexual In My LIFE, Ive Been Unleashed Girl LadyBOY DickGIRL SheMALE Action 3P With A Young Guy D0A6S5S-065 Cute CumSLUT Rino Yuki & Ram Ichinose

First Transsexual In My LIFE, Ive Been Unleashed Girl LadyBOY DickGIRL SheMALE Action 3P With A Young Guy D0A6S5S-065 Cute CumSLUT Rino Yuki & Ram Ichinose

Eporner 3 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 3 months ago

Hot Skinny Trans Fucks Her Hot Girlfriend with a Surprize in Popcorn Bucket

63% 0:39 / 30:09

Hot Skinny Trans Fucks Her Hot Girlfriend with a Surprize in Popcorn Bucket

FapHouse 2 weeks ago

Hot Trans Babe Fucks Virgin Roommate

Hot Trans Babe Fucks Virgin Roommate

xHamster 1 month ago

Athena Parisi's first time with a Cis-Woman!

69% HD 0:10 / 26:05

Athena Parisi's first time with a Cis-Woman!

LoyalFans 4 months ago

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