Challenge Videos - Trans (3,761)

Wedgie wrestling

Wedgie wrestling

Clips4sale 1 year ago

Asia vs Europe Shootout Challenge Pt 010

Asia vs Europe Shootout Challenge Pt 010

aShemaleTube 6 years ago

Here We Goes The Challenge Fight On Ring Bianca Vs

Here We Goes The Challenge Fight On Ring Bianca Vs

getTranny 2 years ago

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

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

Faptor 2 years ago

Transsexual anal challenge in Brazil - Episode #15

Transsexual anal challenge in Brazil - Episode #15

xHamster 2 years ago

Transexual anal challenge - Episode #09

Transexual anal challenge - Episode #09

xHamster 2 years ago

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

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

getTranny 2 years ago

Leticia Vs Luana Extreme Challenge)

Leticia Vs Luana Extreme Challenge)

getTranny 2 years ago

”Fresh widow tested a tgirl meat”

”Fresh widow tested a tgirl meat”

Trashreality 1 year ago

Flexy Sissy Cock Worship Practice

61% HD 1:01 / 8:25

Flexy Sissy Cock Worship Practice

FapHouse 2 years ago

Challenge to a new huge dildo -Part 3

HD 1:01 / 15:20

Challenge to a new huge dildo -Part 3

FapHouse 4 years ago

Big tit muscle futa cock to cock fuck fight: Monica vs Rogue 720p

65% HD 0:30 / 6:15

Big tit muscle futa cock to cock fuck fight: Monica vs Rogue 720p

Clips4sale 1 year ago

”Nerdy hottie gets her delicious holes intruded”

”Nerdy hottie gets her delicious holes intruded”

ThePornstar 1 year 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 1 year 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

Wild Ride on a Monster Dildo! 7.6 Inch Challenge

Wild Ride on a Monster Dildo! 7.6 Inch Challenge

FapHouse 1 year ago

Shemale Blowjob Challenge Will Suck it All

Shemale Blowjob Challenge Will Suck it All

HD21 4 years ago

Continuation of 10 Huge bdsm Challenge

Continuation of 10 Huge bdsm Challenge

xHamster 1 year ago

Will You Challenge Me?

Will You Challenge Me?

Eporner 11 months ago

Step-Sister Physically Dominates You and Owns Your Ass (ID # 1839 HD 1080rez)

Step-Sister Physically Dominates You and Owns Your Ass (ID # 1839 HD 1080rez)

Clips4sale 11 months ago

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

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

Trashreality 11 months ago

Stunning Raven-Haired Beauties Compete In A Steamy Widow's Showdown

Stunning Raven-Haired Beauties Compete In A Steamy Widow's Showdown

Eporner 10 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 10 months ago

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

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

KeekAss 7 months ago

Krissy Lynn dares her holes to welcome TS Michelle Firestones penis

Krissy Lynn dares her holes to welcome TS Michelle Firestones penis

Pornwhite 7 months ago

Shemale samurai challenges you to take her chastity

Shemale samurai challenges you to take her chastity

YouPorn Unknown

futanari milk challenge 3

60% 0:18 / 6:02

futanari milk challenge 3

PornBox 9 months ago

Petite Trans Nixi Leon Loves Feeling BBC

Premium HD 25:02

Petite Trans Nixi Leon Loves Feeling BBC

Sheer 2 years ago

ColbyKnox: Very juicy and tight crossdresser bareback slapping

ColbyKnox: Very juicy and tight crossdresser bareback slapping

IGaySEXTV 1 year ago

No Angel

Premium HD 27:05

TransAngels 6 years 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 10 months ago

Twitchy Femboy gets unmerciful edged by plaything!

Twitchy Femboy gets unmerciful edged by plaything!

Transvids.tv 8 months ago

TGIRLPORNSTAR - Two Trans Gets Threesome

TGIRLPORNSTAR - Two Trans Gets Threesome

Fapnado 8 months 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 7 months ago

Transsexual anal challenge in Brazil - Episode #20

Transsexual anal challenge in Brazil - Episode #20

FapHouse 1 year ago

Transsexual anal challenge in Brazil - Episode #12

Transsexual anal challenge in Brazil - Episode #12

FapHouse 1 year ago

Transsexual anal challenge in Brazil - Episode #08

Transsexual anal challenge in Brazil - Episode #08

FapHouse 1 year ago

”Embracing Challenges: Overcoming Tough Situations”

”Embracing Challenges: Overcoming Tough Situations”

Faptor 2 years ago

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

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

RedTube Unknown

2022 Christmas Cum Eating Challenge CEI

2022 Christmas Cum Eating Challenge CEI

RedTube Unknown

Hands Off Challenge - Day 10

Hands Off Challenge - Day 10

YouPorn Unknown

Dress up with my Bikinis and Lingerie

HD 0:30 / 33:53

Dress up with my Bikinis and Lingerie

Clips4sale 9 months ago

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

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

Zatube 9 months ago

Hot Tranny Kalliny Nomura Fucks The Technician And Cums In His Mouth DT531

Premium HD 33:37

Hot Tranny Kalliny Nomura Fucks The Technician And Cums In His Mouth DT531

Sheer 2 years ago

submit to daddy s edging challenge: pov joi cum command session!

submit to daddy s edging challenge: pov joi cum command session!

PornBox 8 months ago

Sissygasm Challenge Day 2 - Femboy in Chastity Riding Dildo

Sissygasm Challenge Day 2 - Femboy in Chastity Riding Dildo

RedTube Unknown

Perfect ass !

Sheshaft 5 years ago

Sissy challenge 4 Days only in sissy clothes

Sissy challenge 4 Days only in sissy clothes

xHamster 3 years ago

Busty shemale stepmom Ariel Demure threesome blowjob n anal

Busty shemale stepmom Ariel Demure threesome blowjob n anal

Pornwhite 3 years ago

FEMBOY soiree Fake Penis and Magic Wand Sex Do Not Jism Compete!

FEMBOY soiree Fake Penis and Magic Wand Sex Do Not Jism Compete!

TrannyGem 3 years ago

Uber shemale slut Natalie Mars is making sure she doesnt walk right for weeks

Uber shemale slut Natalie Mars is making sure she doesnt walk right for weeks

Pornwhite 3 years ago

Amazon Marcy facessiting trans girl Goddess Rose

Amazon Marcy facessiting trans girl Goddess Rose

Clips4sale 3 years ago

Natally VS Arianna (Tgirls Extreme Challenge)

Natally VS Arianna (Tgirls Extreme Challenge)

xHamster 3 years ago

Transsexual Anal Challenge in Brazil - Episode #14

HD 0:39 / 21:25

Transsexual Anal Challenge in Brazil - Episode #14

FapHouse 4 years ago

Ts Chanel Santini fucks dudes and enjoys anal reaming in group

Ts Chanel Santini fucks dudes and enjoys anal reaming in group

Pervclips 4 years ago

Army guys Tyler tonguefuck Nikos butt-hole

Army guys Tyler tonguefuck Nikos butt-hole

GayCK 4 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

Big cock Tgirl Lucy and the big black mamba dildo challenge

HD 0:39 / 18:15

Big cock Tgirl Lucy and the big black mamba dildo challenge

FapHouse 4 years ago

TS Sex Goddess Takes a Man to His Absolute Limit

HD 0:29 / 35:25

TS Sex Goddess Takes a Man to His Absolute Limit

Clips4sale 4 years ago

Finding the sissygasm

Finding the sissygasm

FapHouse 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 2 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!

Pervclips 2 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

Uber slut Natalie Mars crazy ass fisting

Uber slut Natalie Mars crazy ass fisting

its.PORN 3 years ago

35 or more upvotes on reddit challenge

35 or more upvotes on reddit challenge

xHamster 3 years ago

Natalia Castro 22 Cm Vs Nanda 20 Cm Challenge

Natalia Castro 22 Cm Vs Nanda 20 Cm Challenge

getTranny 2 years ago

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

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

getTranny 2 years ago

Sucking Off Three Futa Dick Girls - A Futanari Scene featuring Big Dicks, Femdom POV, and POV Face Fucking - 720 WMV

HD 0:29 / 11:19

Sucking Off Three Futa Dick Girls - A Futanari Scene featuring Big Dicks, Femdom POV, and POV Face Fucking - 720 WMV

Clips4sale 3 years ago

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

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

getTranny 3 years ago

Priscilla Vs Sabrina (ts Challenge New Edition)

Priscilla Vs Sabrina (ts Challenge New Edition)

getTranny 2 years ago

Bruna 22 Cm Vs Sa 17 Cm Challenge 119)

Bruna 22 Cm Vs Sa 17 Cm Challenge 119)

getTranny 2 years ago

Mandy May Vs Raphaella Ferrari (ts Challenge New Edition) - Teaser Video

Mandy May Vs Raphaella Ferrari (ts Challenge New Edition) - Teaser Video

getTranny 2 years ago

Monique Vs Ferrari (ts Challenge New Edition)

Monique Vs Ferrari (ts Challenge New Edition)

getTranny 2 years ago

Transsexual anal challenge in Brazil - Episode #16

Transsexual anal challenge in Brazil - Episode #16

FapHouse 1 year ago

Transsexual anal challenge in Brazil - Episode #06

Transsexual anal challenge in Brazil - Episode #06

FapHouse 1 year ago

Transsexual Anal Challenge in Brazil - Episode #10

Transsexual Anal Challenge in Brazil - Episode #10

FapHouse 1 year ago

”Insatiable Lana gets her beautiful face covered in cum”

”Insatiable Lana gets her beautiful face covered in cum”

ThePornstar 1 year ago

Trans Princess Jerk Off Instructions Vol 1

Trans Princess Jerk Off Instructions Vol 1

TrannyGem 10 months ago

New Year, Same Stronger-than-you-gf with a bigger cock! (ID # 1827 HD 1080rez)

New Year, Same Stronger-than-you-gf with a bigger cock! (ID # 1827 HD 1080rez)

Clips4sale 1 year ago

Gorgeous Ts-girl moans loudly while jerking

Gorgeous Ts-girl moans loudly while jerking

Katestube 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

Rope Tied Oil Catfight and BDSM Trib Fight part 3

66% 0:30 / 12:27

Rope Tied Oil Catfight and BDSM Trib Fight part 3

Clips4sale 1 year ago

Riding the great american challenge dildo. Almost 2.5 inches thick and 14 inches long

Riding the great american challenge dildo. Almost 2.5 inches thick and 14 inches long

xHamster 1 year ago

TGilrs CHALLENGE “FIGHT 40”, on ring VALENTINA MISS TRANS ITALIA 2017 Vs Jade

Premium HD 45:31

TGilrs CHALLENGE “FIGHT 40”, on ring VALENTINA MISS TRANS ITALIA 2017 Vs Jade

Sheer 3 years ago

TS Natalie Mars In An Anal Threesome

TS Natalie Mars In An Anal Threesome

Eporner 8 months ago

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

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

Eporner 10 months ago

pretty web trap

pretty web trap

Sheshaft 5 years ago

SHEMALE CHALLENGE

SHEMALE CHALLENGE

Eporner 6 years ago

Ice Bucket Challenge with Ladyboy

Ice Bucket Challenge with Ladyboy

Eporner 6 years ago

Queen Natalie disguised and avenged the new fairest in the land

Queen Natalie disguised and avenged the new fairest in the land

Sheshaft 4 years ago

So fucking Good!!! - Chapter #05

So fucking Good!!! - Chapter #05

xHamster 3 years ago

TS Annabelle Lane enjoying a double penetration

TS Annabelle Lane enjoying a double penetration

FetishShrine 7 years ago

”Amy : Pin Up Doll Bareback”

”Amy : Pin Up Doll Bareback”

TransHero 5 years ago

Natsu japanese extreme throat challenge

Natsu japanese extreme throat challenge

XXXShemalePorn 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

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 2 years ago

”Katy Leon - Monstercocking Katy Leon”

”Katy Leon - Monstercocking Katy Leon”

HQBang 2 years ago

Impossible giant dildo insertion in my sissy pussy

Impossible giant dildo insertion in my sissy pussy

xHamster 2 years ago

The German Nymphos Challenge!!! - (episode #02)

The German Nymphos Challenge!!! - (episode #02)

xHamster 2 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 2 years ago

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

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

xHamster 2 years ago

Busty shemale stepmom Ariel Demure threesome blowjob n anal

Busty shemale stepmom Ariel Demure threesome blowjob n anal

Pervclips 3 years ago

Chun Li Cosplayer Escape Challenge Part 1

Chun Li Cosplayer Escape Challenge Part 1

Clips4sale 3 years ago

Transsexual Anal Challenge in Brazil - Episode #15

HD 0:39 / 19:52

Transsexual Anal Challenge in Brazil - Episode #15

FapHouse 4 years ago

AFRICAN BIG COCKS - The Challenge - ROUND #12

AFRICAN BIG COCKS - The Challenge - ROUND #12

Tranny.one 4 years ago

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

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

Pornwhite 4 years ago

alexa readman loves taking bbc all the way

HD 0:30 / 26:48

alexa readman loves taking bbc all the way

PornBox 2 years ago

Mistress Marceau Bondage Model Training Manual Part 1

HD 0:05 / 13:24

Mistress Marceau Bondage Model Training Manual Part 1

Clips4sale 2 years ago

Shemale cock to cock wrestle and sexfight LOW

Shemale cock to cock wrestle and sexfight LOW

Clips4sale 2 years ago

Wanking Challenge

Wanking Challenge

AbTranny 6 years ago

Sissy , virginity , utter ball and humping machine

Sissy , virginity , utter ball and humping machine

TrannyGem 2 years ago

Hot House - Ebony blowjob cum

Hot House - Ebony blowjob cum

GayTubesTV 4 years ago

Sandra in Zipties and Handcuffs with Cruel Domme Star Nine

Sandra in Zipties and Handcuffs with Cruel Domme Star Nine

Clips4sale 1 year ago

Big Johnson Heshe On Cam

Big Johnson Heshe On Cam

Sheshaft 1 year ago

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

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

StarWank 1 year ago

Rosy Pinheiro and Kampfer - BrazilTGirlsXXX

Rosy Pinheiro and Kampfer - BrazilTGirlsXXX

AbTranny 6 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 2 years ago

”T-girl Domme Jessy Dubai Owns Buxxom Blonde Mikki Lynn”

”T-girl Domme Jessy Dubai Owns Buxxom Blonde Mikki Lynn”

StarWank 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

Fapnado 3 years ago

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