Challenge Videos - Trans (3,179)

Slippery Squirty Fun

Slippery Squirty Fun

Some.Porn 7 months ago

Jasmine Dlight - Extreme Anal Training with John Thomas Xl Depth Trainer 30inches Full Dildo

Jasmine Dlight - Extreme Anal Training with John Thomas Xl Depth Trainer 30inches Full Dildo

XHamster 5 months ago

14 Days Sissygasm Challenge handfree only Cumshots

14 Days Sissygasm Challenge handfree only Cumshots

XHamster 1 year ago

Mitsiha&lsquo_s Sissy challenge&mdash_Cream Puffs

Mitsiha&lsquo_s Sissy challenge&mdash_Cream Puffs

XVideos 1 year ago

”Aria Kai challenged by Brickzilla”

”Aria Kai challenged by Brickzilla”

TransHero 7 months ago

Edging Challenge 10/28/25 Day 1 Uncummed 3 Days So Much Pre-Cum

Edging Challenge 10/28/25 Day 1 Uncummed 3 Days So Much Pre-Cum

XVideos 7 months ago

Here we goes the CHALLENGE FIGHT 191, on ring Andrea VS Sara

Here we goes the CHALLENGE FIGHT 191, on ring Andrea VS Sara

XHamster 3 years ago

Silhouette Challenge

Silhouette Challenge

RedTube Unknown

HOW LONG CAN YOU RESIST? SPEED HANDJOB CHALLENGE AS FAST AS POSSIBLE WITH VIVA ATHENA

HOW LONG CAN YOU RESIST? SPEED HANDJOB CHALLENGE AS FAST AS POSSIBLE WITH VIVA ATHENA

XVideos 7 years ago

35 or more upvotes on reddit challenge

35 or more upvotes on reddit challenge

XHamster 3 years ago

”Mixed gender threeway with Emily Willis, Natalie Mars & Dante Colle”

”Mixed gender threeway with Emily Willis, Natalie Mars & Dante Colle”

4Wank 3 years ago

Renata 20 Cm Vs Michelly 15 Cm Challenge 127)

Renata 20 Cm Vs Michelly 15 Cm Challenge 127)

GetTranny 3 years ago

Tgilrs Challenge (round 04) - Daniela Colucci 20 Cm Vs Luana

Tgilrs Challenge (round 04) - Daniela Colucci 20 Cm Vs Luana

GetTranny 3 years ago

Sabrina Rios Vs Ariadny Oliver (ts Challenge New Edition)

Sabrina Rios Vs Ariadny Oliver (ts Challenge New Edition)

GetTranny 3 years ago

Alexia Vs Nicolly Extreme Challenge)

Alexia Vs Nicolly Extreme Challenge)

GetTranny 3 years ago

Tgilrs Challenge (round 01) - Daniela Colucci 20 Cm Vs Luana

Tgilrs Challenge (round 01) - Daniela Colucci 20 Cm Vs Luana

GetTranny 3 years ago

Leticia Vs Luana Extreme Challenge)

Leticia Vs Luana Extreme Challenge)

GetTranny 3 years ago

Here we goes the CHALLENGE FIGHT, on ring Flavia VS Mireja

Here we goes the CHALLENGE FIGHT, on ring Flavia VS Mireja

XHamster 3 years ago

”Katy Leon - Monstercocking Katy Leon”

”Katy Leon - Monstercocking Katy Leon”

TransHero 4 years ago

SHEMALE CHALLENGE

SHEMALE CHALLENGE

Eporner 7 years ago

Perfect ass !

Sheshaft 6 years ago

pretty web trap

pretty web trap

Sheshaft 6 years ago

Luna T-Girl Floozy Challenges u to an Edging Defiance #1

Luna T-Girl Floozy Challenges u to an Edging Defiance #1

ShemaleSin 5 years ago

Penis Hero - Binary State - Bonus Round

Penis Hero - Binary State - Bonus Round

FreePorn8 5 years ago

”Sizzling TS Natalie Mars drilled by a white dong”

”Sizzling TS Natalie Mars drilled by a white dong”

TransHero 4 years ago

Tgilrs Challenge (round 12) - Debora Vasques 21 Cm Vs - Teaser Video

Tgilrs Challenge (round 12) - Debora Vasques 21 Cm Vs - Teaser Video

GetTranny 3 years ago

Bruna 22 Cm Vs Sa 17 Cm Challenge 119)

Bruna 22 Cm Vs Sa 17 Cm Challenge 119)

GetTranny 3 years ago

Priscilla Vs Sabrina (ts Challenge New Edition)

Priscilla Vs Sabrina (ts Challenge New Edition)

GetTranny 3 years ago

Hanna Rios Vs Asia Devil Mireja (ts Challenge New Edition)

Hanna Rios Vs Asia Devil Mireja (ts Challenge New Edition)

GetTranny 3 years ago

Fed with cock milk all the way from the cradle to grave!

Fed with cock milk all the way from the cradle to grave!

Eporner 3 years ago

Natalia Castro 22 Cm Vs Nanda 20 Cm Challenge

Natalia Castro 22 Cm Vs Nanda 20 Cm Challenge

GetTranny 3 years ago

Mireya Vs Drielly (ts Challenge New Edition) - Teaser Video

Mireya Vs Drielly (ts Challenge New Edition) - Teaser Video

GetTranny 3 years ago

Here we goes the CHALLENGE FIGHT, on ring Anna VS Elen

Here we goes the CHALLENGE FIGHT, on ring Anna VS Elen

XHamster 3 years ago

Blonde Challenges Massive Tits Trans EX To Aggressive Bareback Anal Out Of Spite

Blonde Challenges Massive Tits Trans EX To Aggressive Bareback Anal Out Of Spite

GiveMeAPorn 3 years ago

Ice Bucket Challenge with Ladyboy

Ice Bucket Challenge with Ladyboy

Eporner 7 years ago

Busty shemale stepmom Ariel Demure threesome blowjob n anal

Busty shemale stepmom Ariel Demure threesome blowjob n anal

Pornwhite 4 years ago

Tgilrs Challenge (round 15) - Natalia Rodrigues 23 Cm Vs

Tgilrs Challenge (round 15) - Natalia Rodrigues 23 Cm Vs

GetTranny 3 years ago

Monique Vs Ferrari (ts Challenge New Edition)

Monique Vs Ferrari (ts Challenge New Edition)

GetTranny 3 years ago

”Amy : Pin Up Doll Bareback”

”Amy : Pin Up Doll Bareback”

TransHero 6 years ago

Jane Wilde sucking the queens chick shaft while getting pounded from behind

Jane Wilde sucking the queens chick shaft while getting pounded from behind

Sheshaft 4 years ago

Army guys Tyler tonguefuck Nikos butt-hole

Army guys Tyler tonguefuck Nikos butt-hole

GayCK 4 years ago

It's anal time, wake up! - Eva Maxim and Jade Venus

It's anal time, wake up! - Eva Maxim and Jade Venus

Fapnado 3 years ago

Huge Tgirl Gangbang

Huge Tgirl Gangbang

Sheshaft 2 years ago

Big Johnson Heshe On Cam

Big Johnson Heshe On Cam

Sheshaft 2 years ago

TGIRLSEX XXX - Ashley and Brooklyn Challenge For Wild Fuck

TGIRLSEX XXX - Ashley and Brooklyn Challenge For Wild Fuck

AShemaleTube 1 year ago

WHO NEEDS FLYING VANS WHEN WE HAVE EDGING MACHINES?

WHO NEEDS FLYING VANS WHEN WE HAVE EDGING MACHINES?

TrannyGem 1 year ago

Gorgeous Latina tranny Thalia Modesto rides cock like a pro

Gorgeous Latina tranny Thalia Modesto rides cock like a pro

Fapnado 2 years ago

Wanking Challenge

Wanking Challenge

AbTranny 7 years ago

ShemalesFuckGirls Scene: Bia and Anita B

ShemalesFuckGirls Scene: Bia and Anita B

AbTranny 11 years ago

Desperate Femboy Writhes and Prays but is Denied - Day 1

Desperate Femboy Writhes and Prays but is Denied - Day 1

TrannyGem 2 years ago

Electro-Hitachi Edging and Demolished Ejaculations Like A Sissy

Electro-Hitachi Edging and Demolished Ejaculations Like A Sissy

TrannyGem 2 years ago

Nikki does a speed challenge

Nikki does a speed challenge

XXXShemalePorn 2 years ago

Cute Mediterranean Babe Wraps Her Lips Around Agent's Cock

Cute Mediterranean Babe Wraps Her Lips Around Agent's Cock

Some.Porn 2 years ago

Bird Boxxx - S8:E4

Bird Boxxx - S8:E4

Some.Porn 1 year ago

Asia vs Europe Shootout Challenge Pt 010

Asia vs Europe Shootout Challenge Pt 010

AShemaleTube 7 years ago

Tiffany Minx - Size Challenge - Exposed Sissy

Tiffany Minx - Size Challenge - Exposed Sissy

AShemaleTube 2 years ago

”The Haunting Seduction of Michael DelRay: A Supernatural Encounter with Natalie Mars”

”The Haunting Seduction of Michael DelRay: A Supernatural Encounter with Natalie Mars”

Zatube 2 years ago

Trans Girl Gives Step Sis a Big Dick Ride Challenge

Trans Girl Gives Step Sis a Big Dick Ride Challenge

XHamster 1 year ago

”TRANSVR - Cutie Spite Ended Up Fucking Her Housemate”

”TRANSVR - Cutie Spite Ended Up Fucking Her Housemate”

Trashreality 1 year ago

”Tiny Teen Elsa Jean Loves Football & Big P-O-V Penises!”

”Tiny Teen Elsa Jean Loves Football & Big P-O-V Penises!”

ThePornstar 2 years ago

”Hands up if you feel like t-girl on t-girl action today, this one is for you”

”Hands up if you feel like t-girl on t-girl action today, this one is for you”

4Wank 2 years ago

Transsexual anal challenge in Brazil - Episode #18

Transsexual anal challenge in Brazil - Episode #18

XHamster 2 years ago

Transsexual anal challenge in Brazil - Episode #15

Transsexual anal challenge in Brazil - Episode #15

XHamster 2 years ago

Transsexual anal challenge in Brazil - Episode #02

Transsexual anal challenge in Brazil - Episode #02

XHamster 2 years ago

”Mesmerizing Raven-Haired Beauties Compete in a Steamy Widow's Showdown”

”Mesmerizing Raven-Haired Beauties Compete in a Steamy Widow's Showdown”

4Wank 2 years ago

Huge Dildo Challenge! Watch How This Femboy Anal Masturbates Using 4 Huge Dildos!

Huge Dildo Challenge! Watch How This Femboy Anal Masturbates Using 4 Huge Dildos!

AbTranny 3 years ago

Brat Perversions Freaky Sissy Training POV

Brat Perversions Freaky Sissy Training POV

XHamster 2 years ago

Getting vibed on an elliptical with a remote controlled butt plug challenge

Getting vibed on an elliptical with a remote controlled butt plug challenge

XHamster 3 years ago

Here We Goes The Challenge Fight On Ring Sara Vs Mireya

Here We Goes The Challenge Fight On Ring Sara Vs Mireya

GetTranny 3 years ago

Challenge with me in game, I will make you naked come and play we will fuck and play

Challenge with me in game, I will make you naked come and play we will fuck and play

XHamster 3 years ago

Here We Goes The Challenge Fight On Ring Bianca Vs

Here We Goes The Challenge Fight On Ring Bianca Vs

GetTranny 3 years ago

”Fresh widow tested a tgirl meat”

”Fresh widow tested a tgirl meat”

Faptor 2 years ago

Mika Kawaiii's Femboy Twerk Compilation 1

Mika Kawaiii's Femboy Twerk Compilation 1

XHamster 2 years ago

Sissy , virginity , utter ball and humping machine

Sissy , virginity , utter ball and humping machine

TrannyGem 2 years ago

Transexual anal challenge - Episode #09

Transexual anal challenge - Episode #09

XHamster 2 years ago

Natsu japanese extreme throat challenge

Natsu japanese extreme throat challenge

XXXShemalePorn 3 years ago

”Katy Leon - Monstercocking Katy Leon”

”Katy Leon - Monstercocking Katy Leon”

HQBang 3 years ago

Impossible giant dildo insertion in my sissy pussy

Impossible giant dildo insertion in my sissy pussy

XHamster 3 years ago

”Transgender fetishists Janelle Fennec & Melanie Brooks having anal sex”

”Transgender fetishists Janelle Fennec & Melanie Brooks having anal sex”

Faptor 3 years ago

A friendly chess match with chess players Jade Venus and Haley Reed

A friendly chess match with chess players Jade Venus and Haley Reed

Sheshaft 1 year ago

Jade Venus and Haley Reed, are having a friendly chess match

Jade Venus and Haley Reed, are having a friendly chess match

Yeswegays 1 year ago

Hot blonde shemale masturbates with dildo

Hot blonde shemale masturbates with dildo

Some.Porn 1 year ago

24 Hours with My Fuck Machine: Can I Handle It?

24 Hours with My Fuck Machine: Can I Handle It?

XHamster 1 year ago

”Haley Reed & TBabe Jade Venus's chess match heats up!”

”Haley Reed & TBabe Jade Venus's chess match heats up!”

Trashreality 1 year ago

Transsexual gives Wank instructions whilst doing the laundry! If u're a admirable hunk, this babe’ll show u that guy

Transsexual gives Wank instructions whilst doing the laundry! If u're a admirable hunk, this babe’ll show u that guy

ShemaleSin 11 months ago

Shemale Machines 17: Dirty Compilation of Lustful Trannies

Shemale Machines 17: Dirty Compilation of Lustful Trannies

Jizzberry 2 years ago

”TGIRLPORNSTAR - Two Tranny Gets Threeway”

”TGIRLPORNSTAR - Two Tranny Gets Threeway”

ThePornstar 11 months ago

”Haley Reed & TBabe Jade Venus's chess match heats up!”

”Haley Reed & TBabe Jade Venus's chess match heats up!”

Zatube 1 year ago

Twitchy Femboy gets unmerciful edged by fucktoy!

Twitchy Femboy gets unmerciful edged by fucktoy!

TransTube.tv 1 year ago

TGIRLPORNSTAR - Two Trans Gets Threesome

TGIRLPORNSTAR - Two Trans Gets Threesome

Fapnado 1 year ago

suit salwar hot sil satin dress bhabhi big tits desi bhabhi showing boobs

suit salwar hot sil satin dress bhabhi big tits desi bhabhi showing boobs

XHamster 1 year ago

DEVILS FILM - Superstar Trans CHANEL SANTINI has been challenged To A Naughty Gangbang PART 1

DEVILS FILM - Superstar Trans CHANEL SANTINI has been challenged To A Naughty Gangbang PART 1

Xshemale 1 year ago

DESIRE LADYBOY - 2 Tgirls Enjoy a Stiffy Railing Challenge (Fortunate folks)

DESIRE LADYBOY - 2 Tgirls Enjoy a Stiffy Railing Challenge (Fortunate folks)

KeekAss 1 year ago

Bareback with Ladyboy Firsty's Sensational Body

Bareback with Ladyboy Firsty's Sensational Body

XXXShake 2 years ago

T-girls Lynda Caroynne & Adelaide Novaes Fuck Ass

T-girls Lynda Caroynne & Adelaide Novaes Fuck Ass

XHamster 11 months ago

TRANSFIXED Prince And The TS Queen Sharing Snow White's Pussy - Emily Willis, Natalie Mars And Dante Colle

TRANSFIXED Prince And The TS Queen Sharing Snow White's Pussy - Emily Willis, Natalie Mars And Dante Colle

Eporner 1 year ago

【猫耳女装】メスイキアナニー　おしりだけでアクメします　Part2 anal masturbation orgasm challenge crossdress

【猫耳女装】メスイキアナニー　おしりだけでアクメします　Part2 anal masturbation orgasm challenge crossdress

YouPorn Unknown

Immodest Talk During the time that Showing ALL My Holes Close Up

Immodest Talk During the time that Showing ALL My Holes Close Up

ShemaleSin 1 year ago

Kitty Cute Loves Her Huge Assets

Kitty Cute Loves Her Huge Assets

Some.Porn 1 year ago

”TGIRLSEX XXX - Ashley & Brooklyn Challenge For Wild Fuck”

”TGIRLSEX XXX - Ashley & Brooklyn Challenge For Wild Fuck”

ThePornstar 1 year ago

Continuation of 10 Huge bdsm Challenge

Continuation of 10 Huge bdsm Challenge

XHamster 1 year ago

The Draft II: Speed Rounds

The Draft II: Speed Rounds

Some.Porn 2 years ago

Tgilrs Challenge (round 48) - Brenda 22 Cm Vs Raffaella

Tgilrs Challenge (round 48) - Brenda 22 Cm Vs Raffaella

GetTranny 3 years ago

Young sheboy takes another huge dong as a challenge

Young sheboy takes another huge dong as a challenge

IcePorn 1 year ago

TS Natalie Mars In An Anal Threesome

TS Natalie Mars In An Anal Threesome

Eporner 1 year ago

Sissygasm Challenge Day 2 - Femboy in Chastity Riding Dildo

Sissygasm Challenge Day 2 - Femboy in Chastity Riding Dildo

RedTube Unknown

2022 Christmas Cum Eating Challenge CEI

2022 Christmas Cum Eating Challenge CEI

RedTube Unknown

Shemale samurai challenges you to take her chastity

Shemale samurai challenges you to take her chastity

YouPorn Unknown

Will You Challenge Me?

Will You Challenge Me?

Eporner 1 year ago

It's Anal Time, Wake Up! - Eva Maxim And Jade Venus

It's Anal Time, Wake Up! - Eva Maxim And Jade Venus

Eporner 1 year ago

Angels' Deepthroat Challenge

Angels' Deepthroat Challenge

Some.Porn 1 year ago

TRANSGENDER PRINCESS JIZM COMPILATION STAMINA CONTEST PART two - Can you make it to the end ?

TRANSGENDER PRINCESS JIZM COMPILATION STAMINA CONTEST PART two - Can you make it to the end ?

TrannyGem 1 year ago

1 Upvote = 1 Min Reddit Sissy Task Challenge - Erin Rose

1 Upvote = 1 Min Reddit Sissy Task Challenge - Erin Rose

RedTube Unknown

MODERN-DAY SINS - Blonde Challenges Massive Tits Trans EX To Aggressive Bareback Anal Out Of Spite

MODERN-DAY SINS - Blonde Challenges Massive Tits Trans EX To Aggressive Bareback Anal Out Of Spite

YouPorn Unknown

”BRAZILIAN TRANSSEXUALS: New Tranny Beautiful Babe Brenda Christal”

”BRAZILIAN TRANSSEXUALS: New Tranny Beautiful Babe Brenda Christal”

Trashreality 1 year ago

Hands Off Challenge - Day 10

Hands Off Challenge - Day 10

YouPorn Unknown

Sport Challenge

Sport Challenge

XHamster 6 years ago

”Nana : Used For A Sperm Target”

”Nana : Used For A Sperm Target”

TransHero 5 years ago

So fucking Good!!! - Chapter #05

So fucking Good!!! - Chapter #05

XHamster 4 years ago

Giant 18 inch dildo - Part 1

Giant 18 inch dildo - Part 1

XHamster 4 years ago

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