Challenge Videos - Trans (3,831)

SUSANNA 25 cm VS TAMPIRES 21 cm - (TGIRLS CHALLENGE 139)

SUSANNA 25 cm VS TAMPIRES 21 cm - (TGIRLS CHALLENGE 139)

xHamster 3 years ago

public wc fetish whore waiting for being caught by strangers

public wc fetish whore waiting for being caught by strangers

TrannyGem 3 months ago

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

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

xHamster 2 years ago

JULI 23 cm VS SUSY 25 cm - (TGIRLS CHALLENGE 148)

JULI 23 cm VS SUSY 25 cm - (TGIRLS CHALLENGE 148)

xHamster 3 years ago

Perfect Emotional Shemale Cumpilation (try not to cum challenge)

Perfect Emotional Shemale Cumpilation (try not to cum challenge)

aShemaleTube 2 months ago

Riding ONLY (Anal Masturbation Instructional)

HD 0:10 / 19:18

Riding ONLY (Anal Masturbation Instructional)

LoyalFans 4 weeks ago

Try not to nut gay edition volume 3

Try not to nut gay edition volume 3

SexTubeSpot 5 years ago

ALINA 20 cm VS MERY 18 cm - (TGIRLS CHALLENGE 140)

ALINA 20 cm VS MERY 18 cm - (TGIRLS CHALLENGE 140)

xHamster 3 years ago

PAOLA 21 cm VS SARA 24 cm - (TGIRLS CHALLENGE 142)

PAOLA 21 cm VS SARA 24 cm - (TGIRLS CHALLENGE 142)

xHamster 3 years ago

VALERY 25 cm VS AXEN 20 cm - (TGIRLS CHALLENGE 161)

VALERY 25 cm VS AXEN 20 cm - (TGIRLS CHALLENGE 161)

xHamster 3 years ago

BIANCA 24 cm VS SARA 19 cm - (TGIRLS CHALLENGE 137)

BIANCA 24 cm VS SARA 19 cm - (TGIRLS CHALLENGE 137)

xHamster 3 years ago

MARCELLA 24 cm VS SABRINA 27 cm - (TGIRLS CHALLENGE 165)

MARCELLA 24 cm VS SABRINA 27 cm - (TGIRLS CHALLENGE 165)

xHamster 3 years ago

Dana Delvey's Epic Dragon Ride

56% HD 0:10 / 25:10

Dana Delvey's Epic Dragon Ride

LoyalFans 2 months ago

Green with Envy

HD 1:01 / 34:31

Green with Envy

FapHouse 2 weeks ago

Femboy gets edged over and over until he explodes!

Femboy gets edged over and over until he explodes!

Pornzona 1 month ago

Twister Gone Wild: All-Gender Orgy Party - Cliff Media

Twister Gone Wild: All-Gender Orgy Party - Cliff Media

xHamster 1 year ago

Ride Dildo Challenges 2

HD 1:01 / 21:28

Ride Dildo Challenges 2

FapHouse 8 months ago

Trap Hetero Synesthesia

Trap Hetero Synesthesia

BigTitsLust 2 years ago

TGilrs CHALLENGE (round 38) - Natalia De Robrus 20 cm VS

TGilrs CHALLENGE (round 38) - Natalia De Robrus 20 cm VS

xHamster 3 years ago

Post Orgasm Cum Milking Jessica Bloom Big Trans Dick Milking Machine

HD 0:39 / 24:34

Post Orgasm Cum Milking Jessica Bloom Big Trans Dick Milking Machine

FapHouse 1 year ago

Big Tits Latina Teen Loves Hardcore Fucking and Hair Pulling

Big Tits Latina Teen Loves Hardcore Fucking and Hair Pulling

Fapcat 1 year ago

Ts babe reach orgasm by jerking her stiff cock

Ts babe reach orgasm by jerking her stiff cock

VikiPorn 6 months ago

TGilrs CHALLENGE (round 25) - Luna Marksi 22 cm VS Marcela

TGilrs CHALLENGE (round 25) - Luna Marksi 22 cm VS Marcela

xHamster 3 years ago

Cucked By The Pole Dancer

Premium 49% HD 33:25

Cucked By The Pole Dancer

TransAngels 4 years ago

TGilrs CHALLENGE (round 37) - Raphaella Ferrari 22 cm VS

TGilrs CHALLENGE (round 37) - Raphaella Ferrari 22 cm VS

xHamster 3 years ago

7 Ladyboys Cum Contest

7 Ladyboys Cum Contest

FapHouse 2 years ago

Transsexual Anal Challenge in Brazil - Episode #05

Transsexual Anal Challenge in Brazil - Episode #05

xHamster 10 months ago

Here we goes the CHALLENGE FIGHT 211, on ring Mireja VS Flavia

Here we goes the CHALLENGE FIGHT 211, on ring Mireja VS Flavia

xHamster 2 years ago

Unveiled Desires: A Tale of Cuckold, Hotwife

Unveiled Desires: A Tale of Cuckold, Hotwife

xHamster 2 years ago

Solo Competition Hard vs Slow Who Cums Harder Lonely Girlfriend Challenge

Solo Competition Hard vs Slow Who Cums Harder Lonely Girlfriend Challenge

xHamster 4 months 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!

Pornzona 1 month ago

A boy with a big, effeminate-looking butt, to use and tame.

A boy with a big, effeminate-looking butt, to use and tame.

xHamster 4 months ago

Flavia Vs Mireja (ts Challenge New Edition)

Flavia Vs Mireja (ts Challenge New Edition)

getTranny 3 years ago

Hefty fake penis compete! See how this femboy ass fucking wanks using four big fake penises!

Hefty fake penis compete! See how this femboy ass fucking wanks using four big fake penises!

TrannyGem 4 years ago

Part 2 Anal Competition Between Sissy: Barbie in the Cellar Mistress Julia

Part 2 Anal Competition Between Sissy: Barbie in the Cellar Mistress Julia

FapHouse 8 months ago

TRANSVR - Angel Spite Ended Up Screwing Her Housemate

TRANSVR - Angel Spite Ended Up Screwing Her Housemate

ShemaleSin 1 year ago

Furry Fap Hero! - Furry PMV JOI Compilation! CUM CHALLENGE!

Furry Fap Hero! - Furry PMV JOI Compilation! CUM CHALLENGE!

Pornzona 1 week ago

The Princess of Tennis

The Princess of Tennis

Some.Porn 10 months ago

Mistress Destroys Sissy Diaper Hole Prostate Gush Cumshot

Mistress Destroys Sissy Diaper Hole Prostate Gush Cumshot

JuicyTrans 1 week ago

she-creature Samurai Summons you To Take Her Purity

she-creature Samurai Summons you To Take Her Purity

Transvids.tv 6 months ago

Goon your life away for porno mummy sissy angel scarlet black

Goon your life away for porno mummy sissy angel scarlet black

TrannyGem 3 years ago

3D Porn Carton: Petite Busty Princess Takes the Shemale Monster's Fuck Challenge

3D Porn Carton: Petite Busty Princess Takes the Shemale Monster's Fuck Challenge

Fapality 2 years ago

Quintessential Quintuplets Hentai Jerk Off Challenge

Quintessential Quintuplets Hentai Jerk Off Challenge

Fapcat 3 years ago

European Gang-Bang Challenge!!!

European Gang-Bang Challenge!!!

Eporner 1 month ago

SISSY ANAL challenge trying to take 15 INCHES dildo in the ass!!

SISSY ANAL challenge trying to take 15 INCHES dildo in the ass!!

xHamster 2 years ago

Here we goes the CHALLENGE FIGHT 182, on ring Sandy VS Raphaella

Here we goes the CHALLENGE FIGHT 182, on ring Sandy VS Raphaella

xHamster 3 years ago

”T-girl Jessy Dubai moans with every hard thrust her big black cock dom gives”

”T-girl Jessy Dubai moans with every hard thrust her big black cock dom gives”

429Men 2 months ago

shemale dildo hero - edging challenge

shemale dildo hero - edging challenge

Tranny.one 4 years ago

Fresh widow tested a tgirl cock

Fresh widow tested a tgirl cock

Fapnado 4 years ago

Let's See How Good You Are, My Little Wanker! Now You Have to Cum Twice! German - Wichsanleitung

50% HD 1:01 / 6:52

Let's See How Good You Are, My Little Wanker! Now You Have to Cum Twice! German - Wichsanleitung

FapHouse 3 months ago

Here we goes the CHALLENGE FIGHT 216, on ring Lanny VS Marcella

Here we goes the CHALLENGE FIGHT 216, on ring Lanny VS Marcella

xHamster 2 years ago

Rafaela VS Sabrina (Tgirls Extreme Challenge)

Rafaela VS Sabrina (Tgirls Extreme Challenge)

xHamster 3 years ago

Dice Game with Hot Challenges

62% HD 1:01 / 14:51

Dice Game with Hot Challenges

FapHouse 1 week ago

ABT250116 20cm Dildo Challenge

ABT250116 20cm Dildo Challenge

xHamster 1 week ago

Olivia Jayy Ruins Donnie Rock's No Nut Challenge in Record Time

Olivia Jayy Ruins Donnie Rock's No Nut Challenge in Record Time

xHamster 1 day ago

Discode 1

49% HD 1:01 / 20:13

FapHouse 3 weeks ago

Great girl-girl show for her master! Jerk off challenge for two hot tranny girlies!

Great girl-girl show for her master! Jerk off challenge for two hot tranny girlies!

xHamster 1 year ago

Juliana VS Lohara (Tgirls Extreme Challenge)

Juliana VS Lohara (Tgirls Extreme Challenge)

xHamster 3 years ago

Here we goes the CHALLENGE FIGHT, on ring Sabrina VS Ariadny

Here we goes the CHALLENGE FIGHT, on ring Sabrina VS Ariadny

xHamster 2 years ago

Here we goes the CHALLENGE FIGHT 213, on ring Melissa VS Helly

Here we goes the CHALLENGE FIGHT 213, on ring Melissa VS Helly

xHamster 2 years ago

Who Comes First? Nasty JOI for Jerk off Losers! German Deutsch

48% HD 0:39 / 4:09

Who Comes First? Nasty JOI for Jerk off Losers! German Deutsch

FapHouse 2 months ago

Here we goes the CHALLENGE FIGHT, on ring Raissa VS Bianca

Here we goes the CHALLENGE FIGHT, on ring Raissa VS Bianca

xHamster 2 years ago

Renata VS Bella (Tgirls Extreme Challenge)

Renata VS Bella (Tgirls Extreme Challenge)

xHamster 3 years ago

Beautiful post-op swallows my seed

53% HD 0:39 / 13:39

Beautiful post-op swallows my seed

FapHouse 3 years ago

Korra Del Rio Isabella Sorrenti Fuck

Korra Del Rio Isabella Sorrenti Fuck

Dafreeporn 3 weeks ago

DEVILS FILM - Superstar Trans CHANEL SANTINI has been challenged To A Naughty Gangbang PART 2

DEVILS FILM - Superstar Trans CHANEL SANTINI has been challenged To A Naughty Gangbang PART 2

xHamster 10 months ago

I fuck my trans Stepsister in the ass

I fuck my trans Stepsister in the ass

VikiPorn 1 year ago

Bianca VS Bellatrix (Tgirls Extreme Challenge)

Bianca VS Bellatrix (Tgirls Extreme Challenge)

xHamster 3 years ago

Here we goes the CHALLENGE FIGHT 184, on ring Mandy VS Raphaella

Here we goes the CHALLENGE FIGHT 184, on ring Mandy VS Raphaella

xHamster 2 years ago

TS Ria Bentley Fucks TS Gray Perrier in Every Room of Her House!

70% HD 1:01 / 31:22

TS Ria Bentley Fucks TS Gray Perrier in Every Room of Her House!

FapHouse 6 months ago

Starting My Day in the Best Mood Can You Tell?

61% 1:01 / 6:03

Starting My Day in the Best Mood Can You Tell?

FapHouse 2 months ago

This Will Blow Your Mind: Vaniity Is Back

63% HD 1:01 / 35:43

This Will Blow Your Mind: Vaniity Is Back

FapHouse 4 weeks ago

TGilrs CHALLENGE (round 42) - Renata Molina 22 cm VS Keylla

TGilrs CHALLENGE (round 42) - Renata Molina 22 cm VS Keylla

xHamster 3 years ago

Ebony beauty Brooke Morgan solo

Ebony beauty Brooke Morgan solo

xHamster 2 months ago

TGilrs CHALLENGE (round 31) - Hanna Rios 22 cm VSChrystal

TGilrs CHALLENGE (round 31) - Hanna Rios 22 cm VSChrystal

xHamster 3 years ago

Pierce'd to Her Limit!

67% VR 0:39 / 27:07

Pierce'd to Her Limit!

FapHouse 1 year ago

TGilrs CHALLENGE (round 40) - Valentina 23 cm VS Jade 25 cm

TGilrs CHALLENGE (round 40) - Valentina 23 cm VS Jade 25 cm

xHamster 3 years ago

Drink Every Drop from My Mouth - Cum Pillow Challenge

Drink Every Drop from My Mouth - Cum Pillow Challenge

xHamster 5 months ago

Fucked Here We Goes The CHALLENGE FIGHT 178, On Ring Aylla VS Carla

Fucked Here We Goes The CHALLENGE FIGHT 178, On Ring Aylla VS Carla

BeMyHole 2 years ago

Here we goes the CHALLENGE FIGHT, on ring Rebecca Vs Vivian

Here we goes the CHALLENGE FIGHT, on ring Rebecca Vs Vivian

xHamster 2 years ago

Cum Challenge! Who Comes First???

59% HD 0:39 / 4:12

Cum Challenge! Who Comes First???

FapHouse 2 years ago

Group Sex with a Shemale and the Guy Is Fucking Me

Group Sex with a Shemale and the Guy Is Fucking Me

FapHouse 23 hours ago

TGilrs CHALLENGE (round 39) - Lorena Xtravaganza 25 cm VS

TGilrs CHALLENGE (round 39) - Lorena Xtravaganza 25 cm VS

xHamster 3 years ago

Bruna VS Walkiria (Tgirls Extreme Challenge)

Bruna VS Walkiria (Tgirls Extreme Challenge)

xHamster 3 years ago

CAROLA 22 cm VS GRAZIELLA 20 cm - (TGIRLS CHALLENGE 147)

CAROLA 22 cm VS GRAZIELLA 20 cm - (TGIRLS CHALLENGE 147)

xHamster 3 years ago

Open Challenge

aShemaleTube 1 month ago

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

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

ALOTPorn 1 year ago

Best farts compilation - part 1

59% HD 1:01 / 5:33

Best farts compilation - part 1

FapHouse 6 years ago

Rosy VS Nathalia (Tgirls Extreme Challenge)

Rosy VS Nathalia (Tgirls Extreme Challenge)

xHamster 3 years ago

Fishnet Femboy bounces his Fat Ass on Big Dildos

Fishnet Femboy bounces his Fat Ass on Big Dildos

xHamster 7 months ago

Award Winning - Neon Vampire - Evolution Scene Ii

65% 0:39 / 29:15

Award Winning - Neon Vampire - Evolution Scene Ii

FapHouse 1 year ago

Here we goes the CHALLENGE FIGHT, on ring Leona VS Alexia

Here we goes the CHALLENGE FIGHT, on ring Leona VS Alexia

xHamster 2 years ago

Big Dick Melissa Pozzi & Renata Hot Videos Challenge

Big Dick Melissa Pozzi & Renata Hot Videos Challenge

BeMyHole 3 years ago

Fuck And Huge Dick Here We Goes The CHALLENGE FIGHT, On Ring Victoria VS Andrea

Fuck And Huge Dick Here We Goes The CHALLENGE FIGHT, On Ring Victoria VS Andrea

BeMyHole 2 years ago

Female Domination Teenager Mercilessly edges me with a Jerking Machine(Utter Version on OnlyFans @princesscrossed)

Female Domination Teenager Mercilessly edges me with a Jerking Machine(Utter Version on OnlyFans @princesscrossed)

TrannyGem 2 years ago

Sissy Joyce Challenge

Sissy Joyce Challenge

xHamster 1 month ago

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

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

xHamster 2 years ago

Outdoor Workout with Vibrator for Ass and Cock! Tranny Cums Straight Into Her Shorts!

55% HD 0:39 / 5:46

Outdoor Workout with Vibrator for Ass and Cock! Tranny Cums Straight Into Her Shorts!

FapHouse 2 months ago

First to Cum Challenge - Veronica Sanders

First to Cum Challenge - Veronica Sanders

xHamster 1 year ago

Here we goes the CHALLENGE FIGHT, on ring Beatrice VS Renata

Here we goes the CHALLENGE FIGHT, on ring Beatrice VS Renata

xHamster 2 years ago

Jerking Off with Astolfo Part2(Hentai JOI) (Fate Grand Order JOI) (Fap the beat, breathplay, femboy)

Jerking Off with Astolfo Part2(Hentai JOI) (Fate Grand Order JOI) (Fap the beat, breathplay, femboy)

HentaiGem 3 years ago

TGilrs CHALLENGE (round 48) - Brenda 22 cm VS Raffaella

TGilrs CHALLENGE (round 48) - Brenda 22 cm VS Raffaella

xHamster 3 years ago

”BLACK TGIRLS - Heads I Win-Tails You Lose!”

”BLACK TGIRLS - Heads I Win-Tails You Lose!”

Fapnow 2 weeks ago

Hung Shemale Gabrielly Ferraz Fucking Another Chick with a Dick in Hardcore TS Action

Hung Shemale Gabrielly Ferraz Fucking Another Chick with a Dick in Hardcore TS Action

XXXShake 2 months ago

Turbo Cum Draining in 60 Seconds Turbo JOI Cum for your Brain ! Drain yourself in 1 Minute - 60 Seconds JOI Cum Defiance Turbo Prejac Unload

Turbo Cum Draining in 60 Seconds Turbo JOI Cum for your Brain ! Drain yourself in 1 Minute - 60 Seconds JOI Cum Defiance Turbo Prejac Unload

ShemaleSin 1 day ago

Sweaty Dirty Creamy Black Panty Cardio

HD 1:01 / 47:13

Sweaty Dirty Creamy Black Panty Cardio

FapHouse 1 year ago

TsHeadDoctor - Give me a challenge next time?

TsHeadDoctor - Give me a challenge next time?

aShemaleTube 3 years ago

Here we goes the CHALLENGE FIGHT, on ring Lanny VS Marcella

Here we goes the CHALLENGE FIGHT, on ring Lanny VS Marcella

xHamster 2 years ago

JOI Secretary Trans Anal Whore

JOI Secretary Trans Anal Whore

xHamster 2 years ago

”The tennis match turns into a steamy threesome with Jewelz, Eva, & Emma”

”The tennis match turns into a steamy threesome with Jewelz, Eva, & Emma”

LesbianBliss 2 months ago

AB072 Super-Naughty edging and kittling have fun

AB072 Super-Naughty edging and kittling have fun

TrannyGem 3 years ago

Cum Challenge ! Who comes first???

67% HD 0:10 / 4:07

Cum Challenge ! Who comes first???

LoyalFans 2 years ago

Try out of machine fuck thick 15 inch BBC King Cock dildo

Try out of machine fuck thick 15 inch BBC King Cock dildo

xHamster 1 year ago

Gyno Torment at Teleheath Doctor Visit, Medfet Gynecology Roleplay

62% HD 1:01 / 31:07

Gyno Torment at Teleheath Doctor Visit, Medfet Gynecology Roleplay

FapHouse 1 year ago

September through December 2025 Cumpilation

September through December 2025 Cumpilation

xHamster 3 months ago

Trans Fetishists Janelle Fennec And Melanie Brooks Having Anal Sex

Trans Fetishists Janelle Fennec And Melanie Brooks Having Anal Sex

Eporner 1 year ago

You can have a sandwich if you fuck me

4K 0:12 / 33:36

You can have a sandwich if you fuck me

AdultPrime 1 year ago

CAMILLA 20 cm VS STEFANI 23 cm - (TGIRLS CHALLENGE 134)

CAMILLA 20 cm VS STEFANI 23 cm - (TGIRLS CHALLENGE 134)

xHamster 3 years ago

TGilrs CHALLENGE (round 47) - Kiara 22 cm VS Keylla Marques

TGilrs CHALLENGE (round 47) - Kiara 22 cm VS Keylla Marques

xHamster 3 years ago

Here we goes the CHALLENGE FIGHT 178, on ring Aylla VS Carla

Here we goes the CHALLENGE FIGHT 178, on ring Aylla VS Carla

xHamster 3 years ago

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