Pick Up Videos - Trans (5,785)

Picked Up A Guy Ate Him Real Good Then Fucked Him 189,516 Views Added 2025-08-03 With Agatha Lyra

Picked Up A Guy Ate Him Real Good Then Fucked Him 189,516 Views Added 2025-08-03 With Agatha Lyra

PePorn 4 months ago

Two cumshots on one face

Two cumshots on one face

ALOTPorn 13 years ago

Picked up rump tgirl deepthroating before without a condom boinking

Picked up rump tgirl deepthroating before without a condom boinking

TrannyGem 3 years ago

Blond Tranny Predator Taxi Driver Pick Up a Street Boyx

Blond Tranny Predator Taxi Driver Pick Up a Street Boyx

Tranny.one 3 years ago

”Killing the Time”

”Killing the Time”

429Men 4 weeks ago

Chad White Bangs Some Cute Japanese Tourist Girls - WMAF

Chad White Bangs Some Cute Japanese Tourist Girls - WMAF

FapCat 2 years ago

Blond Tranny Predator Taxi Driver Pick Up a Street Boy

Blond Tranny Predator Taxi Driver Pick Up a Street Boy

Tranny.one 4 years ago

Slim blondine fucks a man picked-up at bar

Slim blondine fucks a man picked-up at bar

aShemaleTube 6 years ago

Sensual amateur tgirl barebacks male

Sensual amateur tgirl barebacks male

Eporner 9 years ago

I picked up a big tits hitchhiker which turned out to be a transgender

I picked up a big tits hitchhiker which turned out to be a transgender

Yeswegays 3 years ago

I PICKED UP A STR8 CHAP FROM THE BAR *and gave him the most good oral-sex ever*

I PICKED UP A STR8 CHAP FROM THE BAR *and gave him the most good oral-sex ever*

ShemaleSin 1 year ago

Young Italian Man Picks up a Transsexual in a Bar, Gets a Blowjob, Then Takes Her Home to Get Her Ass Fucked Properly

Young Italian Man Picks up a Transsexual in a Bar, Gets a Blowjob, Then Takes Her Home to Get Her Ass Fucked Properly

xHamster 2 months ago

”New beginnings”

”New beginnings”

TransHero 1 month ago

Easy Pick Up - Outdoor backyard anal sex with busty blonde t-girl Paola Lima

Easy Pick Up - Outdoor backyard anal sex with busty blonde t-girl Paola Lima

Xtits 1 year ago

”JC Wilds seems to love big dicks so she gets screwed inside the bangbus”

”JC Wilds seems to love big dicks so she gets screwed inside the bangbus”

TransHero 1 month ago

Kourtney's Beach Pickup

Kourtney's Beach Pickup

TransTube.tv 7 months ago

”Mature Goth Ho Drains Shaft Professionally”

”Mature Goth Ho Drains Shaft Professionally”

TransHero 1 month ago

Cruising married uber driver fucks teen twink's mouth and cums in his mouth and swallows cum in the car in public

Cruising married uber driver fucks teen twink's mouth and cums in his mouth and swallows cum in the car in public

xHamster 2 years ago

A Real Short Time Experience With Dark Skinned Ladyboy Jina

A Real Short Time Experience With Dark Skinned Ladyboy Jina

Sheshaft 3 years ago

”I can give you something else to suck on”

”I can give you something else to suck on”

LesbianBliss 2 weeks ago

I picked up a a fucking hot hitchhiker which turned out to be a transgender

I picked up a a fucking hot hitchhiker which turned out to be a transgender

Yeswegays 3 years ago

Pickup and Seduction

Pickup and Seduction

aShemaleTube 2 years ago

Thick black girl picks up a guy on the street and rides his dick

Thick black girl picks up a guy on the street and rides his dick

xHamster 1 year ago

German skinny Tranny picked up for ass fuck at the beach

German skinny Tranny picked up for ass fuck at the beach

Tranny.one 1 month ago

He Picks up a Tranny in the Park and Invites Her Home to Fuck Each Other in the Ass.

He Picks up a Tranny in the Park and Invites Her Home to Fuck Each Other in the Ass.

aShemaleTube 5 months ago

Gorgeous trans babe picks up straight boy and breeds him at home

Gorgeous trans babe picks up straight boy and breeds him at home

xHamster 1 year ago

Picked up and rammed a transexual tramp

Picked up and rammed a transexual tramp

Sheshaft 6 years ago

German amateur homemade anal creampie sex date with teen shemale

German amateur homemade anal creampie sex date with teen shemale

xHamster 3 years ago

Trans hitchhiker with flat tits Claire Tenebrarum sucks cock for a ride

Trans hitchhiker with flat tits Claire Tenebrarum sucks cock for a ride

AnySex 2 years ago

Flat chested brunette tranny gets picked up and interracially banged

Flat chested brunette tranny gets picked up and interracially banged

Tranny.one 8 years ago

Khloe Kay picked up by Tranny Chaser Pierce Paris!

Khloe Kay picked up by Tranny Chaser Pierce Paris!

aShemaleTube 5 years ago

Fuck, we're in trouble Wolf, my husband found out

Fuck, we're in trouble Wolf, my husband found out

Fapnado 2 years ago

I Picked Up This Blonde Asian Trans

I Picked Up This Blonde Asian Trans

aShemaleTube 2 months ago

Heather Gets Picked Up

Heather Gets Picked Up

aShemaleTube 1 year ago

Ria's Home Workout with Caramel God

Ria's Home Workout with Caramel God

xHamster 1 year ago

Picked up a Stranger on the Highway and Fucked Him Hard in the Ass for a Ride, Without Condoms, and Came on His Ass

Picked up a Stranger on the Highway and Fucked Him Hard in the Ass for a Ride, Without Condoms, and Came on His Ass

xHamster 3 weeks ago

A man drags 2 horny Latina trannies off for an anal threesome

A man drags 2 horny Latina trannies off for an anal threesome

xHamster 1 year ago

Oh my, I fucked a bigtits trans hitchhiker

Oh my, I fucked a bigtits trans hitchhiker

Fapnado 3 years ago

Street Pick Up Is A Surprise

Street Pick Up Is A Surprise

AbTranny 7 years ago

Shemale street pickup

Shemale street pickup

aShemaleTube 8 years ago

Shemale Prostitute Lexie Beth Fucked

Shemale Prostitute Lexie Beth Fucked

Sheshaft 8 years ago

”Charming Ginger Colombian First Timer Gets Cum On Tits In Sexy Pickup & Fuck”

”Charming Ginger Colombian First Timer Gets Cum On Tits In Sexy Pickup & Fuck”

ThePornstar 8 months ago

Chesty heshe teacher Brittney Kade gets rimmed and barebacked

Chesty heshe teacher Brittney Kade gets rimmed and barebacked

Sheshaft 3 years ago

Blonde Tgirl picked up from the street blowjob then fucked

Blonde Tgirl picked up from the street blowjob then fucked

aShemaleTube 11 years ago

”My Transgender nanny is so , I had to fuck her”

”My Transgender nanny is so , I had to fuck her”

LesbianBliss 2 weeks ago

”T-girl Hardcore All-Stars #3”

”T-girl Hardcore All-Stars #3”

429Men 1 month ago

”She's a 10. All straight guys would fuck her”

”She's a 10. All straight guys would fuck her”

429Men 3 weeks ago

Man picked up streetwalker and was glad finding out that she had cock

Man picked up streetwalker and was glad finding out that she had cock

Tranny.one 8 years ago

Picked up a Slutty Trance Passenger with a Big Cock on the Highway and Fucked Her. Hot Cruise

Picked up a Slutty Trance Passenger with a Big Cock on the Highway and Fucked Her. Hot Cruise

xHamster 3 weeks ago

German Teen t-girl Gianina TS Outdoor anal pick up on vacation

German Teen t-girl Gianina TS Outdoor anal pick up on vacation

BigTitsLust 3 months ago

Public Pickup Of Trans Damsel - Ember Fiera

Public Pickup Of Trans Damsel - Ember Fiera

KeekAss 6 months ago

Latina Surroundings Femboy Bubblz Gets Picked Up Then Plumbed Rigid & Deep - Andre Stone

Latina Surroundings Femboy Bubblz Gets Picked Up Then Plumbed Rigid & Deep - Andre Stone

PePorn 3 months ago

Petite Latina strips bikini and fucked hard

Petite Latina strips bikini and fucked hard

ALOTPorn 7 years ago

public shemale pick up - black man fucks horny transsexual

public shemale pick up - black man fucks horny transsexual

Tranny.one 3 years ago

”Sexy fuck session for Emma Rose & Roman Todd!!”

”Sexy fuck session for Emma Rose & Roman Todd!!”

Rainblow 1 year ago

Lucky Stranger Pick Ups Ts Hitch Hiker And Fuck Her

Lucky Stranger Pick Ups Ts Hitch Hiker And Fuck Her

AbTranny 5 months ago

Handsome stranger picks and analed TS hitchhiker

Handsome stranger picks and analed TS hitchhiker

FapCat 10 months ago

”Road-Trip Threesome: Married Couple Picks Up Hot Hitchhiker”

”Road-Trip Threesome: Married Couple Picks Up Hot Hitchhiker”

LesbianBliss 3 weeks ago

Latina Neighborhood Femboy Bubblz Gets Picked Up then Fucked Hard & Deep

Latina Neighborhood Femboy Bubblz Gets Picked Up then Fucked Hard & Deep

BallsAndBoobs 8 months ago

Tranny fucks blubbery alt whore in sauna

Tranny fucks blubbery alt whore in sauna

Analdin 6 years ago

TS Marjorie gets doggied in bed of pickup

TS Marjorie gets doggied in bed of pickup

aShemaleTube 9 years ago

”Czech lover in public sucking cock with passion”

”Czech lover in public sucking cock with passion”

TransHero 1 month ago

”Cute Latina College Chick Pickup & Seduce To Interracial Casting Fuck”

”Cute Latina College Chick Pickup & Seduce To Interracial Casting Fuck”

TransHero 1 month ago

Pickedup Trans Latina In Braces Gets Anally Pounded

Pickedup Trans Latina In Braces Gets Anally Pounded

PornUse 6 months ago

Trans Hitch Hike Has Hot Anal After Picked Up In Alley With Ariel Demure

Trans Hitch Hike Has Hot Anal After Picked Up In Alley With Ariel Demure

AbTranny 3 months ago

MyDirtyHobby - Busty blonde swallows cum in public

MyDirtyHobby - Busty blonde swallows cum in public

FapCat 1 year ago

Busty Horny Thai Ladyboy Picked Up And Fucked

Busty Horny Thai Ladyboy Picked Up And Fucked

BeMyHole 1 month ago

forever young

PornOne 1 year ago

ladyboy star- i pickup a 18yo slender teen ladyboy at the mall

ladyboy star- i pickup a 18yo slender teen ladyboy at the mall

PornOne 1 year ago

Jamie Page and Chad Rock

Jamie Page and Chad Rock

xHamster 9 months ago

Ria's Home Workout with Caramel God

Ria's Home Workout with Caramel God

xHamster 2 years ago

AJ180 Question and Answer Part 2

AJ180 Question and Answer Part 2

xHamster 4 years ago

Very Horny, Goes On The Track Pick Up Her Girlfriend

Very Horny, Goes On The Track Pick Up Her Girlfriend

Eporner 1 year ago

Picked Her Up And Brought Her Back, Merely To Discover This babe's A Trans! Her Wang Is Larger Than Mine...

Picked Her Up And Brought Her Back, Merely To Discover This babe's A Trans! Her Wang Is Larger Than Mine...

FreePorn8 1 month ago

First Time with a Shemale - Paid for the Pleasure

First Time with a Shemale - Paid for the Pleasure

Jizzberry 2 years ago

Jessica Host One Night Stand

Jessica Host One Night Stand

xHamster 6 months ago

Lanita Super-steamy Gets Picked Up And Pounded

Lanita Super-steamy Gets Picked Up And Pounded

KeekAss 1 month ago

TikTok Pickup Line got a Hot Girl from my Gym to Give me a BJ and let me Fuck her in Parking Lot!

TikTok Pickup Line got a Hot Girl from my Gym to Give me a BJ and let me Fuck her in Parking Lot!

FapCat 2 years ago

tranny picked up in car to have anal sex in the car

tranny picked up in car to have anal sex in the car

xHamster 3 years ago

”Sexy fuck session for Emma Rose & Roman Todd!!”

”Sexy fuck session for Emma Rose & Roman Todd!!”

Trashreality 1 year ago

Picking up a Sexy Shemale off the Streets and Giving Her My BBC

Picking up a Sexy Shemale off the Streets and Giving Her My BBC

PornFreeNow 1 month ago

”GotFilled: Brynn Michaels Gets Her Cervix Blasted”

”GotFilled: Brynn Michaels Gets Her Cervix Blasted”

ThePornstar 6 months ago

D*A*S*S 020 A Surprise Lesbian Pick Up With A Crossdresser. He Was Make Amateur Girls Cum With His Penis, But Instead He Made Them Cum With His Amazing Technique Decensored

D*A*S*S 020 A Surprise Lesbian Pick Up With A Crossdresser. He Was Make Amateur Girls Cum With His Penis, But Instead He Made Them Cum With His Amazing Technique Decensored

Eporner 4 months ago

Nice trannies with beautiful asses eat cocks and gets deep anal

Nice trannies with beautiful asses eat cocks and gets deep anal

xHamster 3 months ago

”retribution Sex Pick-up in the Dodgiest Alley”

”retribution Sex Pick-up in the Dodgiest Alley”

TransHero 1 month ago

Street Pick Up Is A Surprise

Street Pick Up Is A Surprise

TrannyGem 6 years ago

Nice trannies with beautiful asses eat cocks and gets deep anal

Nice trannies with beautiful asses eat cocks and gets deep anal

xHamster 2 months ago

Blondie ladyman Predator Cab Driver Pick Up A Street Boyx

Blondie ladyman Predator Cab Driver Pick Up A Street Boyx

TrannyGem 5 years ago

”Road-Trip Threeway: Married Couple Picks Up Hot Hitchhiker”

”Road-Trip Threeway: Married Couple Picks Up Hot Hitchhiker”

Zatube 1 year ago

Black guy picked up experienced transsexual and bought his anus

Black guy picked up experienced transsexual and bought his anus

Tranny.one 8 years ago

Trans redhead with a tight hole gets seduced and fucked anally

Trans redhead with a tight hole gets seduced and fucked anally

XGroovy 1 year ago

Dude Bangs a Tranny Hard From the Streets

Dude Bangs a Tranny Hard From the Streets

Yeswegays 7 years ago

A hot blond trans is picked up and railed by bbc

A hot blond trans is picked up and railed by bbc

Eporner 2 months ago

Anal Outdoor Joy

Anal Outdoor Joy

Some.Porn 9 months ago

Reverse picking up, extreme cute transsexual

Reverse picking up, extreme cute transsexual

Tranny.one 1 year ago

Blonde TS Hooker Picks Up Guys

Blonde TS Hooker Picks Up Guys

aShemaleTube 14 years ago

Picked up amateur ladyboy jerks off solo

Picked up amateur ladyboy jerks off solo

aShemaleTube 2 years ago

Hot outdoor fuck with a nasty blonde

Hot outdoor fuck with a nasty blonde

ALOTPorn 13 years ago

I PICKED UP A STRAIGHT GUY FROM THE HOTEL and I gave him the best blowjob ever

I PICKED UP A STRAIGHT GUY FROM THE HOTEL and I gave him the best blowjob ever

xHamster 9 months ago

Horny Whore Notice A Solo Male On Pick-Up Truck So She Makes Him Feeling Good

58% HD 1:01 / 28:44

Horny Whore Notice A Solo Male On Pick-Up Truck So She Makes Him Feeling Good

FapHouse 2 years ago

”1 Chick on the Whole Street - Picked up by PUA POV”

”1 Chick on the Whole Street - Picked up by PUA POV”

TransHero 3 weeks ago

Homeless Transgender Damsel Picked Up By Stranger For Lovemaking In His Jeep

Homeless Transgender Damsel Picked Up By Stranger For Lovemaking In His Jeep

TrannyGem 3 months ago

Nikki Montero Street Butterfly Pickup Monica Mattos and DOUBLE PENETRATION and Cum Shots

Nikki Montero Street Butterfly Pickup Monica Mattos and DOUBLE PENETRATION and Cum Shots

TrannyGem 6 years ago

Picked up on the Highway and Fucked in the Car by Sissy Femboy in Stockings Without a Condom! Filled It All with Cum!

61% HD 1:01 / 21:16

Picked up on the Highway and Fucked in the Car by Sissy Femboy in Stockings Without a Condom! Filled It All with Cum!

FapHouse 1 year ago

Anal creampie cumshot outdoors by the pool - Easy Pick Up Tranny Paola Lima

Anal creampie cumshot outdoors by the pool - Easy Pick Up Tranny Paola Lima

Xtits 1 year ago

Picked Up A Stranger On The Highway And Fucked Him Hard In The Ass For A Ride, Without A Condom, And C cummed On His Ass

Picked Up A Stranger On The Highway And Fucked Him Hard In The Ass For A Ride, Without A Condom, And C cummed On His Ass

xHamster 1 month ago

Picked Her Up And Brought Her Back, Solely To Find She's A Trans! Her Penis Is Bigger Than Mine...

Picked Her Up And Brought Her Back, Solely To Find She's A Trans! Her Penis Is Bigger Than Mine...

Dafreeporn 1 month ago

oriental tgirl gets Picked Up At The Beach And gets screwed

oriental tgirl gets Picked Up At The Beach And gets screwed

Transvids.tv 11 months ago

Shemale Busty Hitchhiker Got Anal Fuck For A Ride - Blake Lovely

Shemale Busty Hitchhiker Got Anal Fuck For A Ride - Blake Lovely

PePorn 3 months ago

Hitchhiker picked up to get dominated in transsexual BDSM fuckfest

Hitchhiker picked up to get dominated in transsexual BDSM fuckfest

Tranny.one 2 years ago

Cutie eighteen gets her 1st ebony ramrod

Cutie eighteen gets her 1st ebony ramrod

Ebony8 5 months ago

TS prostitute Jenna Belle is facialized

TS prostitute Jenna Belle is facialized

FetishShrine 12 years ago

Toyko Love Hotel With Ts Twist: Be Careful When You Pick Up Strangers

Toyko Love Hotel With Ts Twist: Be Careful When You Pick Up Strangers

AbTranny 2 years ago

I PICKED UP A HETERO MAN FROM THE PUB *and gave him the finest oral ever*

I PICKED UP A HETERO MAN FROM THE PUB *and gave him the finest oral ever*

TrannyGem 1 year ago

He Picks up a Tranny on the Street and Takes Her Home for a Nice Active and Passive Fuck.

He Picks up a Tranny on the Street and Takes Her Home for a Nice Active and Passive Fuck.

xHamster 1 month ago

”Czech Bitch Gets Picked Up For Car Sex”

”Czech Bitch Gets Picked Up For Car Sex”

TransHero 1 month ago

”Street Slut Picked up for CarFuck”

”Street Slut Picked up for CarFuck”

TransHero 1 month ago

Sydney Love in Making his Dreams CUM True

Sydney Love in Making his Dreams CUM True

Tranny.one 3 years ago

I would normally never do this. But she had a sign saying sucks shaft for a ride

I would normally never do this. But she had a sign saying sucks shaft for a ride

Pornwhite 3 years ago

T-Girl is picking up a shemale hooker

T-Girl is picking up a shemale hooker

ShemaleSin 5 years ago

1 2 3 4 5

5,785 results found

Related categories

Street Pickup Begging Nympho Free Use Flat Chested Milking Table Czech Fantasy Pawn Shop Glasses Downblouse Face Sitting Shy Tan Lines Job Interview Boat Braces Slim Rich Backseat Poker

Narrow your search

pick up teen 18+ daniel knight pick up bar pick up pick up anal amateur pick up pick up girl japanese pick up pick up street street pick up thai pick up asian pick up public pick up pick up stranger pick up amateur real pick up shemale pick up latina pick up ebony pick up milf pick up teen pick up 18+

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.