Challenge Videos - Trans (4,232)

Leticia VS Carolina (Tgirls Extreme Challenge)

Leticia VS Carolina (Tgirls Extreme Challenge)

xHamster 3 years ago

Best farts compilation - part 1

62% HD 1:01 / 5:33

Best farts compilation - part 1

FapHouse 6 years ago

20181204 - cocotranse - fap challenge pmv - feminized

20181204 - cocotranse - fap challenge pmv - feminized

XXXShemalePorn 6 years ago

Shemale Doctor Banging Max Asshole With Giant Weenie And Collecting Sperm

Shemale Doctor Banging Max Asshole With Giant Weenie And Collecting Sperm

Dafreeporn 2 weeks ago

TGilrs CHALLENGE - Valesca Sargentely 22 Cm

TGilrs CHALLENGE - Valesca Sargentely 22 Cm

BeMyHole 2 years ago

30 mins no break fellate spitroast contest!

30 mins no break fellate spitroast contest!

TrannyGem 7 months ago

Arm Strength Challenge

Arm Strength Challenge

FapHouse 9 months ago

Here we goes the CHALLENGE FIGHT 192, on ring Sandy VS Anna

Here we goes the CHALLENGE FIGHT 192, on ring Sandy VS Anna

xHamster 3 years 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

Bianca VS Bellatrix (Tgirls Extreme Challenge)

Bianca VS Bellatrix (Tgirls Extreme Challenge)

xHamster 3 years ago

Maha the Russian Trans MILF (part 2 of 2)

Maha the Russian Trans MILF (part 2 of 2)

FapHouse 4 days ago

Shemale Stepmom Fucking Sex Doll Pussy With Big Cock Caught By Stepson

Shemale Stepmom Fucking Sex Doll Pussy With Big Cock Caught By Stepson

xHamster 2 weeks ago

Bianca VS Natalia (Tgirls Extreme Challenge)

Bianca VS Natalia (Tgirls Extreme Challenge)

xHamster 3 years ago

Anal Challenge

Some.Porn 1 year ago

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

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

xHamster 3 years ago

Fresh widow tested a tgirl cock

Fresh widow tested a tgirl cock

Fapnado 4 years 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

Strapon Anal Challenge

Strapon Anal Challenge

xHamster 2 years ago

I fuck my trans Stepsister in the ass

I fuck my trans Stepsister in the ass

SleazyNEasy 1 year ago

Cum Challenge ! Who comes first???

69% HD 0:10 / 4:07

Cum Challenge ! Who comes first???

LoyalFans 2 years ago

Dice Game with Hot Challenges

Dice Game with Hot Challenges

aShemaleTube 3 weeks ago

Russian girl destroyed by dildo trying not to cum compilation

Russian girl destroyed by dildo trying not to cum compilation

JuicyTrans 3 weeks ago

TGilrs CHALLENGE (round 17) - Aika Montanellii 22 cm VS

TGilrs CHALLENGE (round 17) - Aika Montanellii 22 cm VS

xHamster 3 years 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

Big Cocks TGilrs CHALLENGE - Brenda 22 Cm VS Raffaella

Big Cocks TGilrs CHALLENGE - Brenda 22 Cm VS Raffaella

BeMyHole 3 years ago

Sweaty Dirty Creamy Black Panty Cardio

HD 1:01 / 47:13

Sweaty Dirty Creamy Black Panty Cardio

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

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

Penny Peacock – Takes Smash Challenge

Penny Peacock – Takes Smash Challenge

AbTranny 4 years ago

TSSexual.com - Eva Maxim's athletic spit roast challenge

TSSexual.com - Eva Maxim's athletic spit roast challenge

UrGayPorn 16 hours 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

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

The Howard Stern Display, Finest Transgirl challenge part two

The Howard Stern Display, Finest Transgirl challenge part two

KeekAss 5 years ago

Cute Trans Gril Takes On Monster Tentacle Dildo

Cute Trans Gril Takes On Monster Tentacle Dildo

xHamster 4 years ago

September through December 2025 Cumpilation

September through December 2025 Cumpilation

xHamster 5 months ago

TheThroatBully Exclusive Trailer: DickGirl and Sprite Challenge

TheThroatBully Exclusive Trailer: DickGirl and Sprite Challenge

aShemaleTube 3 years ago

Dice Game with Hot Challenges

Dice Game with Hot Challenges

xHamster 3 weeks 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

Watch this hot amateur contest the stroke challenge with a steamy solo session

Watch this hot amateur contest the stroke challenge with a steamy solo session

GayVD 3 months 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

Carolina & Selena

Carolina & Selena

xHamster 2 years ago

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

45% HD 0:39 / 4:09

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

FapHouse 4 months ago

Sissyboy Wanted It Rough.He Got More Than He Expected

Sissyboy Wanted It Rough.He Got More Than He Expected

xHamster 1 week ago

Jaqueline VS Dany (Tgirls Extreme Challenge)

Jaqueline VS Dany (Tgirls Extreme Challenge)

xHamster 3 years ago

Sissy Training Day 1 - First Steps of Transformation

Sissy Training Day 1 - First Steps of Transformation

FapHouse 6 days ago

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

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

xHamster 3 years ago

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

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

xHamster 3 years ago

Stroking challenger

Stroking challenger

aShemaleTube 7 years 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

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

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

Maha the Russian Trans MILF (part 1 of 2)

Maha the Russian Trans MILF (part 1 of 2)

FapHouse 1 week ago

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

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

xHamster 3 years ago

Performance test for stroke losers! Can you ruin your orgasm 10 times? JOI GERMAN DEUTSCH

Performance test for stroke losers! Can you ruin your orgasm 10 times? JOI GERMAN DEUTSCH

xHamster 3 months ago

Beautiful post-op swallows my seed

51% HD 1:01 / 13:39

Beautiful post-op swallows my seed

FapHouse 3 years ago

Give me more

Some.Porn 11 months ago

RIDE IT BETTER THAN YOUR GF!!TRY NOT TO CUM CHALLENGE (COMP)

RIDE IT BETTER THAN YOUR GF!!TRY NOT TO CUM CHALLENGE (COMP)

Tranny.one 4 years ago

Dr. Meets Antonio Black

Dr. Meets Antonio Black

Some.Porn 1 year ago

Transsexual Anal Challenge in Brazil - Episode #05

Transsexual Anal Challenge in Brazil - Episode #05

xHamster 1 year ago

Here we goes the CHALLENGE FIGHT, on ring Allana Vs Vallesca

Here we goes the CHALLENGE FIGHT, on ring Allana Vs Vallesca

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 183, on ring Anna VS Elen

Here we goes the CHALLENGE FIGHT 183, on ring Anna VS Elen

xHamster 3 years ago

RED-HOT EMO T-MODEL EDGING CONTEST *TRY NOT TO JISM GAME*

RED-HOT EMO T-MODEL EDGING CONTEST *TRY NOT TO JISM GAME*

TrannyGem 4 years ago

TGilrs CHALLENGE (round 06) - Erika Lavigne 23 cm VS Nikolly

TGilrs CHALLENGE (round 06) - Erika Lavigne 23 cm VS Nikolly

xHamster 3 years ago

TGilrs CHALLENGE (round 13) - Nikolly Gaucha 25 cm VS

TGilrs CHALLENGE (round 13) - Nikolly Gaucha 25 cm VS

xHamster 3 years 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

Sissy Training Day 1 - First Steps of Transformation

Sissy Training Day 1 - First Steps of Transformation

FapHouse 6 days ago

Femboy Hooters Girl Takes BBC in the Bathroom

Femboy Hooters Girl Takes BBC in the Bathroom

xHamster 1 year ago

Playlist Edging Challenge

Playlist Edging Challenge

FapHouse 2 months ago

Stunning Pietra Raw Fucks Her Lucky Fella

Stunning Pietra Raw Fucks Her Lucky Fella

xHamster 3 weeks ago

Fucked, Fisted & Filled with Cum by Thick Monster Cock TS

64% HD 0:10 / 43:34

Fucked, Fisted & Filled with Cum by Thick Monster Cock TS

LoyalFans 1 year ago

[Trans] Game Over (Remastered)

VR 1:11 / 42:05

[Trans] Game Over (Remastered)

VrSmash 5 months ago

Here we goes the CHALLENGE FIGHT, on ring Elisabet VS

Here we goes the CHALLENGE FIGHT, on ring Elisabet VS

xHamster 3 years ago

”Krissy Lynn dares her holes to welcome Transgender Michelle Firestones meat”

”Krissy Lynn dares her holes to welcome Transgender Michelle Firestones meat”

Trashreality 9 months ago

Mature Shemale MILF Strokes Monster Dick for Messy Cumshot POV

Mature Shemale MILF Strokes Monster Dick for Messy Cumshot POV

SleazyNEasy 5 months ago

I Hit It Last

Premium HD 24:01

TransAngels 6 years ago

Naughty nun plays with a large unholy member

Naughty nun plays with a large unholy member

xHamster 2 years ago

”Krissy Lynn dares her holes to welcome Transgender Michelle Firestones meat”

”Krissy Lynn dares her holes to welcome Transgender Michelle Firestones meat”

ThePornstar 9 months ago

German amateur shemale destroys her ass and cums hard

German amateur shemale destroys her ass and cums hard

xHamster 5 years 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

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

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

Group Sex with a Shemale and the Guy Is Fucking Me

64% HD 1:01 / 9:41

Group Sex with a Shemale and the Guy Is Fucking Me

FapHouse 1 month ago

Post Orgasm Cum Milking Jessica Bloom Big Trans Dick Milking Machine

71% HD 1:01 / 24:34

Post Orgasm Cum Milking Jessica Bloom Big Trans Dick Milking Machine

FapHouse 2 years ago

Jessica Host Fucks Kurt Connors Hard In Top Chef Ts Penis Challenge Scene

Jessica Host Fucks Kurt Connors Hard In Top Chef Ts Penis Challenge Scene

Sheshaft 3 weeks 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

Verge and Stroke Jerk Off Instructions ft Trans Female Dom

Verge and Stroke Jerk Off Instructions ft Trans Female Dom

TrannyGem 6 months ago

”Super Hung Daddy Teaches a Lesson in Hole Stretching”

”Super Hung Daddy Teaches a Lesson in Hole Stretching”

TransHero 5 months 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

Bonus Update

xHamster 3 weeks ago

Black Daddy Ken Busts Open Candy Ass Sissy's White Ass to New Levels of Ecstacy and Agony with Thick 10-inch BBC (60 Fps)

Black Daddy Ken Busts Open Candy Ass Sissy's White Ass to New Levels of Ecstacy and Agony with Thick 10-inch BBC (60 Fps)

xHamster 2 years 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

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

He Likes Seats And He Cannot Lie

He Likes Seats And He Cannot Lie

Some.Porn 11 months ago

Cum Challenge! Who Comes First???

59% HD 0:39 / 4:12

Cum Challenge! Who Comes First???

FapHouse 2 years ago

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

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

xHamster 3 years ago

Sexy Jade Trolling for Poling

HD 0:39 / 44:42

Sexy Jade Trolling for Poling

FapHouse 9 months ago

Transexual anal challenge - Episode #10

Transexual anal challenge - Episode #10

xHamster 2 years 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

The F Off

Some.Porn 2 months 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

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

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

xHamster 1 month 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

Cucked By The Pole Dancer

Premium 49% HD 33:25

Cucked By The Pole Dancer

TransAngels 4 years ago

Extremely enlarged pumping dick

Extremely enlarged pumping dick

xHamster 1 month ago

Here we goes the CHALLENGE FIGHT 207, on ring Evelin VS Gemma

Here we goes the CHALLENGE FIGHT 207, on ring Evelin VS Gemma

xHamster 3 years ago

transmidnight - petite trans nyxi leon loves feeling bbc

transmidnight - petite trans nyxi leon loves feeling bbc

TransDoe 2 years ago

Who's doing no nut November? This video is a challenge for you

63% HD 1:01 / 6:29

Who's doing no nut November? This video is a challenge for you

FapHouse 3 years ago

Brazilian TGilrs CHALLENGE - Valesca Sargentely

Brazilian TGilrs CHALLENGE - Valesca Sargentely

BeMyHole 2 years ago

Stepson Caught Tgirl Stepmom Fucking His Sex Doll Pussy With Huge Cock

Stepson Caught Tgirl Stepmom Fucking His Sex Doll Pussy With Huge Cock

Dafreeporn 1 week ago

Shemale Andreia Mel in some hot latina pussy

Shemale Andreia Mel in some hot latina pussy

xHamster 6 months ago

Ts babe reach orgasm by jerking her stiff cock

Ts babe reach orgasm by jerking her stiff cock

FetishShrine 7 months ago

Award Winning - Neon Vampire - Evolution Scene Ii

69% 0:39 / 29:15

Award Winning - Neon Vampire - Evolution Scene Ii

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

ANNA 24 cm VS Miss JULI 23 cm - (TGIRLS CHALLENGE 166)

ANNA 24 cm VS Miss JULI 23 cm - (TGIRLS CHALLENGE 166)

xHamster 3 years ago

EP21: Taming and Fucking Lots of Demons - Breeders of the Nephelym

EP21: Taming and Fucking Lots of Demons - Breeders of the Nephelym

xHamster 1 year ago

TGIRLSEX XXX - Ashley and Brooklyn Challenge For Wild Fuck

TGIRLSEX XXX - Ashley and Brooklyn Challenge For Wild Fuck

Fapnado 1 year ago

Pantyhose Woman vs Orgasmite 3 - Live on Villain TV

HD 0:30 / 19:28

Pantyhose Woman vs Orgasmite 3 - Live on Villain TV

Clips4sale 5 months ago

Challenge #10 BDSM and Femdom: College: Student - twice cumshot, VERY BIG Ruined orgasm, Post orgasm

Challenge #10 BDSM and Femdom: College: Student - twice cumshot, VERY BIG Ruined orgasm, Post orgasm

xHamster 3 years ago

Here we goes the CHALLENGE FIGHT, on ring Rosy Vs Beatrice

Here we goes the CHALLENGE FIGHT, on ring Rosy Vs Beatrice

xHamster 3 years ago

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