Challenge Videos - Trans (4,263)

Strapon Anal Challenge

Strapon Anal Challenge

xHamster 2 years ago

Pierce'd to Her Limit!

62% VR 0:39 / 27:07

Pierce'd to Her Limit!

FapHouse 1 year ago

Foreskin Covered Cum & Piss Challenge - Never Retracting

48% HD 1:01 / 6:16

Foreskin Covered Cum & Piss Challenge - Never Retracting

FapHouse 6 months ago

Mrs Nara and 4 TS uses a guy and a girl as fuck holes - Complete (720 EN-sub)

52% 4K 0:29 / 42:03

Mrs Nara and 4 TS uses a guy and a girl as fuck holes - Complete (720 EN-sub)

Clips4sale 3 years ago

Group Sex with a Shemale and the Guy Is Fucking Me

59% HD 0:39 / 9:41

Group Sex with a Shemale and the Guy Is Fucking Me

FapHouse 1 month ago

Arm Strength Challenge

Arm Strength Challenge

FapHouse 9 months ago

Public Nudity While Cycling!! Tranny Girl Rides Not Only the Bike, Also a Dildo!

66% HD 0:39 / 11:20

Public Nudity While Cycling!! Tranny Girl Rides Not Only the Bike, Also a Dildo!

FapHouse 4 months ago

Here we goes the CHALLENGE FIGHT 176, on ring Alexia Vs Diana

Here we goes the CHALLENGE FIGHT 176, on ring Alexia Vs Diana

xHamster 3 years ago

Bikers

64% VR 1:05 / 59:04

VirtualRealTrans 1 year ago

Shemale Andreia Mel in some hot latina pussy

Shemale Andreia Mel in some hot latina pussy

xHamster 6 months ago

AB2503 Secretary 50cm long dildo challenge (Chinese and English subtitles)

AB2503 Secretary 50cm long dildo challenge (Chinese and English subtitles)

xHamster 1 year ago

30 Minutes on the Elliptical While Getting Vibed With a Remote Controlled Butt Plug Challenge

HD 1:01 / 28:21

30 Minutes on the Elliptical While Getting Vibed With a Remote Controlled Butt Plug Challenge

FapHouse 2 years ago

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

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

xHamster 3 years ago

[Trans] Game Over (Remastered)

VR 1:11 / 42:05

[Trans] Game Over (Remastered)

VrSmash 5 months ago

Jasminedlight & Valentina Rosa - Outdoor Garden Extreme Anal Training Footing

65% HD 1:01 / 8:54

Jasminedlight & Valentina Rosa - Outdoor Garden Extreme Anal Training Footing

FapHouse 9 months ago

Sophia & Ashley: Endurance Challenge

Sophia & Ashley: Endurance Challenge

ALOTPorn 2 weeks ago

Tatted TS Kelly Lovely rammed shemale Cassie Cummings in the kitchen

Tatted TS Kelly Lovely rammed shemale Cassie Cummings in the kitchen

UrGayPorn 6 months ago

My shower after i fuck my boyfriend and cum in his ass

My shower after i fuck my boyfriend and cum in his ass

xHamster 1 year ago

Bonus Update

xHamster 4 weeks ago

”Super Hung Daddy Teaches a Lesson in Hole Stretching”

”Super Hung Daddy Teaches a Lesson in Hole Stretching”

TransHero 6 months ago

Blonde Slender Slut Happy Ending in Her Mouth

66% HD 0:30 / 13:39

Blonde Slender Slut Happy Ending in Her Mouth

Clips4sale 3 years ago

Petite Trans Nixi Leon Loves Feeling BBC

Petite Trans Nixi Leon Loves Feeling BBC

xHamster 1 year ago

Discode 1

57% HD 0:39 / 20:13

FapHouse 2 months ago

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

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

xHamster 3 years ago

Stunning Pietra Raw Fucks Her Lucky Fella

64% HD 0:39 / 25:08

Stunning Pietra Raw Fucks Her Lucky Fella

FapHouse 1 month ago

Vanniall two HOUR two JIZM SHOT Edging Web cam Flash - Huge Trans Shaft Solo Jizm Shots - Fap Off Together

Vanniall two HOUR two JIZM SHOT Edging Web cam Flash - Huge Trans Shaft Solo Jizm Shots - Fap Off Together

TransTube.tv 1 year ago

Slutty Shemale MILF Sucks Monster Pecker in Raw POV Cam Show

Slutty Shemale MILF Sucks Monster Pecker in Raw POV Cam Show

Sheshaft 10 months ago

Sissy Training Day 1 - First Steps of Transformation

Sissy Training Day 1 - First Steps of Transformation

FapHouse 1 week ago

Bianca VS Bellatrix (Tgirls Extreme Challenge)

Bianca VS Bellatrix (Tgirls Extreme Challenge)

xHamster 3 years ago

TGilrs CHALLENGE (round 12) - Debora Vasques 21 cm VS

TGilrs CHALLENGE (round 12) - Debora Vasques 21 cm VS

xHamster 3 years ago

Dr. Meets Antonio Black

Dr. Meets Antonio Black

Some.Porn 1 year ago

Extreme Deepthroat Challenge of the Gagging Reflex - Pig Pushes Its Limits

Extreme Deepthroat Challenge of the Gagging Reflex - Pig Pushes Its Limits

FapHouse 3 weeks ago

Maha the Russian Trans MILF (part 1 of 2)

Maha the Russian Trans MILF (part 1 of 2)

FapHouse 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 3 months ago

Here we goes the CHALLENGE FIGHT, on ring Vittoria VS Gisel

Here we goes the CHALLENGE FIGHT, on ring Vittoria VS Gisel

xHamster 3 years ago

We're Still Here with the Chinese Balls. Eater-ass

44% HD 0:39 / 8:27

We're Still Here with the Chinese Balls. Eater-ass

FapHouse 5 months ago

Here we goes the CHALLENGE FIGHT 208, on ring Flavia VS Mireja

Here we goes the CHALLENGE FIGHT 208, on ring Flavia VS Mireja

xHamster 3 years ago

TGilrs CHALLENGE (round 36) - Litizia Sallis 24 cm VS

TGilrs CHALLENGE (round 36) - Litizia Sallis 24 cm VS

xHamster 3 years ago

Outdoor workout with vibrator for ass and cock! Tranny cums straight into her shorts!

70% HD 0:30 / 5:40

Outdoor workout with vibrator for ass and cock! Tranny cums straight into her shorts!

Clips4sale 1 year ago

TGilrs CHALLENGE - Valesca Sargentely 22 Cm

TGilrs CHALLENGE - Valesca Sargentely 22 Cm

BeMyHole 2 years ago

Big Cocks TGilrs CHALLENGE (round 42) - Renata Molina 22 Cm VS Keylla

Big Cocks TGilrs CHALLENGE (round 42) - Renata Molina 22 Cm VS Keylla

BeMyHole 2 years ago

German amateur shemale destroys her ass and cums hard

German amateur shemale destroys her ass and cums hard

xHamster 5 years ago

Pantyhose Woman vs Orgasmite 3 - Live on Villain TV

57% HD 0:30 / 19:28

Pantyhose Woman vs Orgasmite 3 - Live on Villain TV

Clips4sale 5 months ago

I fuck my trans Stepsister in the ass

I fuck my trans Stepsister in the ass

VikiPorn 1 year ago

Penny Peacock – Takes Smash Challenge

Penny Peacock – Takes Smash Challenge

AbTranny 4 years ago

Sweaty Dirty Creamy Black Panty Cardio

HD 1:01 / 47:13

Sweaty Dirty Creamy Black Panty Cardio

FapHouse 1 year ago

Here we goes the CHALLENGE FIGHT 212, on ring Hellen VS Milla

Here we goes the CHALLENGE FIGHT 212, on ring Hellen VS Milla

xHamster 3 years ago

Ab065 Happy Chinese New Year-red Food Challenge And Nice Blow Job - 恭喜发财红色食物大挑战-性感红衣女郎口交射精 With Abby Kitty

Ab065 Happy Chinese New Year-red Food Challenge And Nice Blow Job - 恭喜发财红色食物大挑战-性感红衣女郎口交射精 With Abby Kitty

PornUse 7 months ago

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

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

xHamster 3 years ago

Erika VS Victoria (Tgirls Extreme Challenge)

Erika VS Victoria (Tgirls Extreme Challenge)

xHamster 3 years ago

you have two Mins to do with me as you satisfy(Corded Female Dominance)

you have two Mins to do with me as you satisfy(Corded Female Dominance)

TrannyGem 1 year ago

Aylla Gattina Vs Carla Tavares (ts Challenge New Edition)

Aylla Gattina Vs Carla Tavares (ts Challenge New Edition)

getTranny 3 years ago

I fuck my trans Stepsister in the ass

I fuck my trans Stepsister in the ass

SleazyNEasy 1 year ago

DEVILS FILM - Wild Bisexual Threesome With Wife Adira Allure And Two Big Cocks

DEVILS FILM - Wild Bisexual Threesome With Wife Adira Allure And Two Big Cocks

Some.Porn 1 year ago

Brazilian And Big Cocks TGilrs CHALLENGE - Kiara 22 Cm VS Keylla Marques

Brazilian And Big Cocks TGilrs CHALLENGE - Kiara 22 Cm VS Keylla Marques

BeMyHole 3 years ago

onlyfans - pietra radi yasmine de castro bianca lima tgirlplayhouse transgirl orgy

onlyfans - pietra radi yasmine de castro bianca lima tgirlplayhouse transgirl orgy

TransDoe 2 years ago

Finally all in with the ultimate challenge - Dick Rambone to the balls

Finally all in with the ultimate challenge - Dick Rambone to the balls

Tranny.one 4 years ago

Agatha Lila A Sexy And Mature Drag Queen Who Challenges Herself By Having Sex With A Black Man Until His Enormous Penis Rots Away

Agatha Lila A Sexy And Mature Drag Queen Who Challenges Herself By Having Sex With A Black Man Until His Enormous Penis Rots Away

Eporner 2 months ago

Here we goes the CHALLENGE FIGHT 205, on ring Mireja VS Drielly

Here we goes the CHALLENGE FIGHT 205, on ring Mireja VS Drielly

xHamster 3 years ago

wichsanleitung an tranny wendy für dich ich zeig dir wie stud wichst! sexdoll realistic doll

wichsanleitung an tranny wendy für dich ich zeig dir wie stud wichst! sexdoll realistic doll

SortPorn 6 months ago

This Whore Got Nailed

This Whore Got Nailed

xHamster 2 months ago

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

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

xHamster 3 years ago

Fresh widow tested a tgirl cock

Fresh widow tested a tgirl cock

Fapnado 4 years ago

thirty minutes no break deepthroat spitroast defiance!

thirty minutes no break deepthroat spitroast defiance!

ShemaleSin 3 years ago

Stefani Suspended - Stefani Special and Elise Graves - subby Stefani completely submits to the rope suspension experience!

66% 4K 0:59 / 21:05

Stefani Suspended - Stefani Special and Elise Graves - subby Stefani completely submits to the rope suspension experience!

Clips4sale 1 year ago

Sissification Lecture "Ultimate Guide to Sissy Lovemaking Playthings" Veronica Taboo invites you to Sissy Academy

Sissification Lecture "Ultimate Guide to Sissy Lovemaking Playthings" Veronica Taboo invites you to Sissy Academy

TransTube.tv 1 year ago

EP3: Fucking Angelic Pirouette in the Ass - Femboy Futa Mania

EP3: Fucking Angelic Pirouette in the Ass - Femboy Futa Mania

xHamster 3 months ago

Dice Game with Hot Challenges

Dice Game with Hot Challenges

xHamster 1 month ago

Here we goes the CHALLENGE FIGHT 206, on ring Mireja VS Emanuela

Here we goes the CHALLENGE FIGHT 206, on ring Mireja VS Emanuela

xHamster 3 years ago

Watch these kinky babes get their tight pussies licked in a wild threesome

Watch these kinky babes get their tight pussies licked in a wild threesome

Some.Porn 2 years ago

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

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

xHamster 3 years ago

Transsexual Anal Challenge in Brazil - Episode #05

Transsexual Anal Challenge in Brazil - Episode #05

xHamster 1 year ago

Blake Lovely - Extreme Deepthroat - Swallowing Rodrigo Amor's Thick 10 Inch Monster Cock Gag Challenge

Blake Lovely - Extreme Deepthroat - Swallowing Rodrigo Amor's Thick 10 Inch Monster Cock Gag Challenge

Clips4sale 3 months ago

Maha the Russian Trans MILF (part 2 of 2)

Maha the Russian Trans MILF (part 2 of 2)

FapHouse 1 week ago

Kiss The Ball

xHamster 2 months ago

Busty Latina TS Angela Bratz takes down a big dick stud

70% HD 1:01 / 30:58

Busty Latina TS Angela Bratz takes down a big dick stud

FapHouse 4 years ago

Ts babe reach orgasm by jerking her stiff cock

Ts babe reach orgasm by jerking her stiff cock

FetishShrine 7 months ago

I Hit It Last

Premium HD 24:01

TransAngels 6 years ago

September through December 2025 Cumpilation

September through December 2025 Cumpilation

xHamster 5 months ago

Carolina & Selena

Carolina & Selena

xHamster 2 years ago

Yoruichi X Nami - Showing Her Biggest Fan Why She's Considered the Best

Yoruichi X Nami - Showing Her Biggest Fan Why She's Considered the Best

3DPornDude 5 days ago

natassia dreams & misty stone obsessed

natassia dreams & misty stone obsessed

PornOne 4 years ago

Open Challenge

aShemaleTube 2 months ago

Anal Beads, Buttplug and Huge Dildo - Anal Training Cumslut Jessica Bloom

Anal Beads, Buttplug and Huge Dildo - Anal Training Cumslut Jessica Bloom

xHamster 1 year ago

Vola-004 [i want to be sandwiched through thin trans

Vola-004 [i want to be sandwiched through thin trans

TeenTVX 3 years ago

The Howard Stern Demonstrate, Greatest She-Male challenge part 1

The Howard Stern Demonstrate, Greatest She-Male challenge part 1

KeekAss 5 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

Lovely TRANSSEXUAL Challenges A Pump Her Butt Utter Of Jizz

Lovely TRANSSEXUAL Challenges A Pump Her Butt Utter Of Jizz

TrannyGem 2 weeks ago

Here we goes the CHALLENGE FIGHT 199, on ring Beatrice VS Renata

Here we goes the CHALLENGE FIGHT 199, on ring Beatrice VS Renata

xHamster 3 years ago

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

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

xHamster 3 years ago

The Howard Stern Display, Finest Transgirl challenge part two

The Howard Stern Display, Finest Transgirl challenge part two

KeekAss 5 years ago

TGIRLSEX XXX - Ashley and Brooklyn Challenge For Wild Fuck

TGIRLSEX XXX - Ashley and Brooklyn Challenge For Wild Fuck

Fapnado 1 year ago

ADULT TIME Sexy T Girl Izzy Wilde Challenges Her GF Cam

ADULT TIME Sexy T Girl Izzy Wilde Challenges Her GF Cam

aShemaleTube 1 month ago

Sexy Jade Trolling for Poling

HD 0:39 / 44:42

Sexy Jade Trolling for Poling

FapHouse 10 months ago

JOI Challenge by Tranny: Show Me What a Good Wanker You Are, Cum in a Minute! German Deutsch

61% HD 0:39 / 3:10

JOI Challenge by Tranny: Show Me What a Good Wanker You Are, Cum in a Minute! German Deutsch

FapHouse 4 months ago

UP CLOSE - HOW TRANS WOMEN ORGASM COMPILATION! EMBER FIERA, JADE VENUS, BRITTNEY KADE, TORI EASTON

UP CLOSE - HOW TRANS WOMEN ORGASM COMPILATION! EMBER FIERA, JADE VENUS, BRITTNEY KADE, TORI EASTON

Fapcat 1 year ago

Rosy VS Pamela (Tgirls Extreme Challenge)

Rosy VS Pamela (Tgirls Extreme Challenge)

xHamster 3 years ago

Muddy Chatting Stroke Compete - Straight, Trans or Homo

Muddy Chatting Stroke Compete - Straight, Trans or Homo

2BGay 2 years ago

BIG DICK TGIRL EDGING INTO OBLIVION VINTAGE ORIGINAL FULL VIDEO

BIG DICK TGIRL EDGING INTO OBLIVION VINTAGE ORIGINAL FULL VIDEO

xHamster 2 days ago

Cum in Panties CEI JOI- Cum Eating Instructions by Goddess Nikki Kit

61% HD 0:25 / 11:21

Cum in Panties CEI JOI- Cum Eating Instructions by Goddess Nikki Kit

IWantClips 1 year ago

Naughty nun plays with a large unholy member

Naughty nun plays with a large unholy member

xHamster 2 years 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

aShemaleTube 11 months ago

A Rewarding Morning Awakening: Blowjob, Fist, Pegging, Chastity Release and Handjob : Mistress Julia

A Rewarding Morning Awakening: Blowjob, Fist, Pegging, Chastity Release and Handjob : Mistress Julia

xHamster 1 year ago

Brazilian And Big Tits TGilrs CHALLENGE - Daniela Colucci 20 Cm VS Luana

Brazilian And Big Tits TGilrs CHALLENGE - Daniela Colucci 20 Cm VS Luana

BeMyHole 3 years ago

Discode 1

46% HD 1:01 / 20:13

FapHouse 2 months ago

Super Hardcore Anal Action with Transsexual Leah Hayes

Super Hardcore Anal Action with Transsexual Leah Hayes

Some.Porn 1 week ago

Cute Teens Love Big Black Cock

Cute Teens Love Big Black Cock

Some.Porn 1 year ago

Cute Trans Gril Takes On Monster Tentacle Dildo

Cute Trans Gril Takes On Monster Tentacle Dildo

xHamster 4 years ago

Open Challenge (Early Access)

Premium HD 33:43

Open Challenge (Early Access)

xnxxGold 3 months ago

Can anal stimulation bring a closed femboy to orgasm?

Can anal stimulation bring a closed femboy to orgasm?

xHamster 5 days ago

”TGIRLS XXX - Pop The Balloon - Tranny Edition”

”TGIRLS XXX - Pop The Balloon - Tranny Edition”

Rainblow 1 week ago

Luna Lust Cute Bubble Butt Small Tits Brunette Teen POV No Hand Deepthroat Blowjob

46% HD 0:39 / 43:37

Luna Lust Cute Bubble Butt Small Tits Brunette Teen POV No Hand Deepthroat Blowjob

FapHouse 1 year 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

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

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

Faptor 1 year ago

DEVILS FILM - Superstar Trans CHANEL SANTINI has been challenged To A Nasty Group sex PART 1

DEVILS FILM - Superstar Trans CHANEL SANTINI has been challenged To A Nasty Group sex PART 1

ShemaleSin 11 months ago

Marcela Dimov in Command!

62% HD 1:01 / 23:11

Marcela Dimov in Command!

FapHouse 1 year ago

Wolf Wagners Dirty Jungle Party 3: Lively Threesome Finale

Wolf Wagners Dirty Jungle Party 3: Lively Threesome Finale

Some.Porn 1 year ago

Krissy Lynn dares her holes to welcome TS Michelle Firestones cock

Krissy Lynn dares her holes to welcome TS Michelle Firestones cock

UrGayPorn 9 months ago

TGilrs CHALLENGE - Veronika Havenna 25 Cm

TGilrs CHALLENGE - Veronika Havenna 25 Cm

BeMyHole 2 years ago

Ep3: Fucking Angelic Pirouette in the Ass - Femboy Futa Mania

Ep3: Fucking Angelic Pirouette in the Ass - Femboy Futa Mania

xHamster 2 months ago

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