Challenge Videos - Trans (3,033)

I played the challenges and he fuck me

I played the challenges and he fuck me

YouPorn Unknown

Hands Off Challenge - Day 7

Hands Off Challenge - Day 7

YouPorn Unknown

I'm Really Different Now Even Though I've Been Here for so Long.

HD 1:01 / 40:39

I'm Really Different Now Even Though I've Been Here for so Long.

FapHouse 8 months ago

Mom tells sissy to not spunk nomatter how much you want to

Mom tells sissy to not spunk nomatter how much you want to

TrannyGem 7 months 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

”T-girl Khloe Kay endures three big cocks simultaneously drilling her booty an”

”T-girl Khloe Kay endures three big cocks simultaneously drilling her booty an”

Trashreality 10 months 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

Xshemale 9 months ago

Hands Off Challenge - Day 20

Hands Off Challenge - Day 20

RedTube Unknown

Natalie Mars and Sasha Sissy: Daily Dildo Drilling and Booty Rimming Cosplay Fun!

Natalie Mars and Sasha Sissy: Daily Dildo Drilling and Booty Rimming Cosplay Fun!

ALOTPorn 11 months ago

Krissy Lynn dares her holes to welcome TS Michelle Firestones cock

Krissy Lynn dares her holes to welcome TS Michelle Firestones cock

Fapnado 9 months ago

Huge Hollow Butt Plug!!

Huge Hollow Butt Plug!!

xHamster 9 months ago

30 Day's of Cum Video Challenge Video #1

30 Day's of Cum Video Challenge Video #1

xHamster 9 months ago

Creampie Compilation Cum Challenge #2

Creampie Compilation Cum Challenge #2

Eporner 9 months ago

TGIRLPORNSTAR: Adriana Rodrigues & Natalia Trans & Dante

TGIRLPORNSTAR: Adriana Rodrigues & Natalia Trans & Dante

xHamster 9 months ago

Producer&#039;s Arraial 2025: Jully Takes on the Big

Producer&#039;s Arraial 2025: Jully Takes on the Big

xHamster 9 months ago

Trans Beauty Edging and Gooning Until Giant Jizz flow

Trans Beauty Edging and Gooning Until Giant Jizz flow

ShemaleSin 10 months ago

”Big Titted Jessy Dubai butt drilled by sexy stud Jessy Dubai”

”Big Titted Jessy Dubai butt drilled by sexy stud Jessy Dubai”

ThePornstar 9 months ago

Young shemale takes one more huge dick as a challenge

Young shemale takes one more huge dick as a challenge

XVideos 7 years ago

Krissy Lynn dares her holes to welcome TS Michelle Firestones cock

Krissy Lynn dares her holes to welcome TS Michelle Firestones cock

UrGayPorn 7 months ago

Another Hilarious Challenge I Come Across Today

Another Hilarious Challenge I Come Across Today

xHamster 1 year ago

”Misty Stone & Natassia Dreams have tremendous sex”

”Misty Stone & Natassia Dreams have tremendous sex”

Trashreality 1 year ago

”TRANSVR - Cutie Spite Ended Up Fucking Her Housemate”

”TRANSVR - Cutie Spite Ended Up Fucking Her Housemate”

Zatube 1 year ago

”Embracing Challenges: Overcoming Tough Situations”

”Embracing Challenges: Overcoming Tough Situations”

ThePornstar 1 year ago

Secretdreamsfuta Intense Ride: Curvy Beauty Takes on Massive Challenge with Passion

Secretdreamsfuta Intense Ride: Curvy Beauty Takes on Massive Challenge with Passion

FapHouse 11 months ago

Cum Challenge Filling A Full Glass With Cum (cei)

Cum Challenge Filling A Full Glass With Cum (cei)

AbTranny 3 years ago

Trans Girl Gives Step Sis a Big Dick Ride Challenge

Trans Girl Gives Step Sis a Big Dick Ride Challenge

FapHouse 1 year ago

Tattooed trans Joey Stone suffers pussy stretching and deepthroating

Tattooed trans Joey Stone suffers pussy stretching and deepthroating

Fapnado 10 months ago

hefty pleasure button love glove collar

hefty pleasure button love glove collar

TrannyGem 1 year ago

Bro Seeking Bro: Riding Into A New Level Of Intensity

Bro Seeking Bro: Riding Into A New Level Of Intensity

GayMenSexTube 5 months ago

BLACK TGIRLS - The Japanese Kitten Unleashed

BLACK TGIRLS - The Japanese Kitten Unleashed

Fapnado 5 months ago

Rosy Vs Nathalia Extreme Challenge)

Rosy Vs Nathalia Extreme Challenge)

Xshemale 5 months ago

Emily Did Her Superlatively good to Not Cum in Expertised Weenie Sucker Cutie's Taut Throat and Mouth

Emily Did Her Superlatively good to Not Cum in Expertised Weenie Sucker Cutie's Taut Throat and Mouth

ShemaleSin 5 months ago

Temptation and steamy thrill with transbabe Morgan Bailey at the bar

Temptation and steamy thrill with transbabe Morgan Bailey at the bar

Yeswegays 5 months ago

Temptation and steamy thrill with transbabe Morgan Bailey at the bar

Temptation and steamy thrill with transbabe Morgan Bailey at the bar

VikiPorn 5 months ago

Jasminedlight & Valentina Rosa - Outdoor Garden Extreme Anal Training Footing

Jasminedlight & Valentina Rosa - Outdoor Garden Extreme Anal Training Footing

xHamster 6 months ago

The Cross-dresser Puts a Glass Ball in Her Anus and Writhes

The Cross-dresser Puts a Glass Ball in Her Anus and Writhes

FapHouse 6 months ago

Tgilrs Challenge (round 08) - Tiffany 22 Cm Vs Debora

Tgilrs Challenge (round 08) - Tiffany 22 Cm Vs Debora

PornUse 5 months ago

Tgilrs Challenge (round 27) - Priscilla Beckam 20 Cm Vs

Tgilrs Challenge (round 27) - Priscilla Beckam 20 Cm Vs

PornUse 5 months ago

”Pierce Paris gave Tony Orlando hard punishment after pissing him off”

”Pierce Paris gave Tony Orlando hard punishment after pissing him off”

TransHero 3 months ago

Watch this inked babe deepthroat a shemale cock with her tight throat

Watch this inked babe deepthroat a shemale cock with her tight throat

FetishShrine 4 months ago

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

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

429Men 8 months ago

300 Millimeters the Great Challenge

300 Millimeters the Great Challenge

FapHouse 4 months ago

Self-training 49: M-leg Split Challenge at a Beach

HD 1:01 / 32:35

Self-training 49: M-leg Split Challenge at a Beach

FapHouse 3 months ago

S1UTTRANSPUP - BRATTY PUP dares you to destroy their ass better than they can!

S1UTTRANSPUP - BRATTY PUP dares you to destroy their ass better than they can!

xHamster 3 months ago

Emily Did Her Most excellent to Not Cum in Expertised Dong Sucker Gal's Taut Throat and Mouth

Emily Did Her Most excellent to Not Cum in Expertised Dong Sucker Gal's Taut Throat and Mouth

BigTitsLust 5 months ago

Shemale hentai Ashe Cumming A Lot After Caught by Her Mentor mother I'd like to fuck

Shemale hentai Ashe Cumming A Lot After Caught by Her Mentor mother I'd like to fuck

SortPorn 4 months ago

”Fuck Your Step Sibling Challenge - Mackenzie Moss”

”Fuck Your Step Sibling Challenge - Mackenzie Moss”

TransHero 3 months ago

Tgilrs Challenge (round 33 23 Cm Vs - Raphaella Ferrari

Tgilrs Challenge (round 33 23 Cm Vs - Raphaella Ferrari

PornUse 3 months ago

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

XVideos 3 years ago

Boyish Cameron Taylor vs FTM Luke Hudson

Boyish Cameron Taylor vs FTM Luke Hudson

ALOTPorn 1 month ago

Manhood Railing Challenge Inbetween She-creatures Melyna Merli and Nicolly Pantoja

Manhood Railing Challenge Inbetween She-creatures Melyna Merli and Nicolly Pantoja

TrannyGem 1 month ago

The Brim Game Week One Day 6

The Brim Game Week One Day 6

TrannyGem 7 months ago

Tanned Nutty overcomes hard cock plowing her trans ass

Tanned Nutty overcomes hard cock plowing her trans ass

UrGayPorn 7 months ago

Shemale Blowjob Challenge Will Suck it All

Shemale Blowjob Challenge Will Suck it All

MyLust 4 years ago

Young tgirl takes another huge dick as a challenge

Young tgirl takes another huge dick as a challenge

XVideos 7 years ago

Esthefany moviendo el culo

Esthefany moviendo el culo

XVideos 7 years ago

Jasmine Dlight Extreme Anal Training with Self Fist, Giant Egg Plug and Dildo

HD 1:01 / 11:29

Jasmine Dlight Extreme Anal Training with Self Fist, Giant Egg Plug and Dildo

FapHouse 7 months ago

Young shemale takes one more huge dick as a challenge

Young shemale takes one more huge dick as a challenge

XVideos 7 years ago

30 Minutes On The Elliptical While Getting Vibed With a Remote Controlled Butt Plug Challenge

30 Minutes On The Elliptical While Getting Vibed With a Remote Controlled Butt Plug Challenge

XVideos 1 year ago

[3D Comiс] Futa Fight Champions Bailey Vs Delia

[3D Comiс] Futa Fight Champions Bailey Vs Delia

HentaiGem 2 years ago

pink top big boobs crossdresser teasing

pink top big boobs crossdresser teasing

xHamster 8 months ago

Uperstar Trans Chanel Santini Has Been Challenged To A Naughty Gangbang

Uperstar Trans Chanel Santini Has Been Challenged To A Naughty Gangbang

getTranny 7 months ago

Big Dick Renata Hot Videos Challenge With Melissa Pozzi

Big Dick Renata Hot Videos Challenge With Melissa Pozzi

PePorn 6 months ago

This Will Blow Your Mind: Vaniity Is Back

This Will Blow Your Mind: Vaniity Is Back

xHamster 1 week ago

Perfect Cuban Trans Versatile Fuck

Perfect Cuban Trans Versatile Fuck

XPornPlay 1 month ago

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

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

TransHero 3 months ago

WISH TRANSGIRL - 2 Trans Bitches Have a Dinky Railing Challenge

WISH TRANSGIRL - 2 Trans Bitches Have a Dinky Railing Challenge

KeekAss 1 month ago

”Lets settle who is the best cunt licker”

”Lets settle who is the best cunt licker”

LesbianBliss 3 weeks ago

Self-training No. 98: Standing Fuck Machine Masturbation

Self-training No. 98: Standing Fuck Machine Masturbation

xHamster 1 month ago

Twitchy Femboy gets ruthlessly edged by toy!

Twitchy Femboy gets ruthlessly edged by toy!

Pornzona 1 month ago

Femboy MILF in the Ultimate Gooner Boy Challenge

Femboy MILF in the Ultimate Gooner Boy Challenge

xHamster 3 weeks ago

”Insatiable Lana gets her gorgeous face covered in cum”

”Insatiable Lana gets her gorgeous face covered in cum”

TransHero 3 months ago

Femboy MILF in the Ultimate Gooner Boy Challenge

HD 1:01 / 22:31

Femboy MILF in the Ultimate Gooner Boy Challenge

FapHouse 3 weeks ago

Nerdy Sissy Femboy Gaped Raw by Monster Cock Moans Squirms Cum Challenge

Nerdy Sissy Femboy Gaped Raw by Monster Cock Moans Squirms Cum Challenge

JuicyTrans 1 week ago

Sissy Joyce Challenge

Sissy Joyce Challenge

YouPorn Unknown

Subby Little Femboy Slut is Orgasm Deprived - Day 2

Subby Little Femboy Slut is Orgasm Deprived - Day 2

Pornzona 3 weeks ago

FEMOUT - Amateur Bogdana and Her Dream For Anal Sex tool

FEMOUT - Amateur Bogdana and Her Dream For Anal Sex tool

ShemaleSin 4 months ago

Self-training No. 26: Exposure Walk with Urination

Self-training No. 26: Exposure Walk with Urination

xHamster 4 months ago

Jade Venus fucks her voluptuous voluptuous friends Olivia Jay and Little Puck

Jade Venus fucks her voluptuous voluptuous friends Olivia Jay and Little Puck

Pornwhite 2 months ago

”GROOBYVR - Miss Canadian Pie”

”GROOBYVR - Miss Canadian Pie”

Rainblow 2 months ago

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

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

FapHouse 2 months ago

Johnny Depp Stepmom Best Cumshot Compil3

Johnny Depp Stepmom Best Cumshot Compil3

Fapcat 1 year ago

”FEMOUT - Bogdana Bogdana Bogdana”

”FEMOUT - Bogdana Bogdana Bogdana”

IFuckedYourGF 1 month ago

”Inked transgender Joey Stone suffers beaver stretching & deepthroating”

”Inked transgender Joey Stone suffers beaver stretching & deepthroating”

LesbianBliss 2 months ago

”T-girl Khloe Kay endures three big cocks simultaneously drilling her booty an”

”T-girl Khloe Kay endures three big cocks simultaneously drilling her booty an”

Rainblow 2 months ago

Krissy Lynn dares her holes to welcome TS Michelle Firestones cock

Krissy Lynn dares her holes to welcome TS Michelle Firestones cock

Fapcat 8 months ago

Hot Girls with Big Dicks Fuck Sexy p2

Hot Girls with Big Dicks Fuck Sexy p2

Fapcat 1 year ago

Suckable Toes Cum On My Feet Challenge Foot Fetish

Suckable Toes Cum On My Feet Challenge Foot Fetish

xHamster 2 months ago

Jade Venus fucks her hot sexy friends Olivia Jay and Little Puck

Jade Venus fucks her hot sexy friends Olivia Jay and Little Puck

Pornicom 2 months ago

Jade Venus fucks her hot sexy friends Olivia Jay and Little Puck

Jade Venus fucks her hot sexy friends Olivia Jay and Little Puck

SleazyNEasy 2 months ago

Jade Venus fucks her hot sexy friends Olivia Jay and Little Puck

Jade Venus fucks her hot sexy friends Olivia Jay and Little Puck

Pornicom 2 months ago

”Taking the biggest meat of her life!”

”Taking the biggest meat of her life!”

TransHero 3 months ago

Boomerang Launches Your Challenge

Boomerang Launches Your Challenge

FapHouse 3 months ago

Self-training No. 48: Tackle-ass Exposure Challenge Walk

57% HD 0:08 / 0:40

Self-training No. 48: Tackle-ass Exposure Challenge Walk

FapHouse 3 months ago

”GROOBY.CLUB: TALYTA SOARES & MARCUS!”

”GROOBY.CLUB: TALYTA SOARES & MARCUS!”

Rainblow 1 year ago

”Stunning Latin shemale Thalia Modesto rides dick like a pro”

”Stunning Latin shemale Thalia Modesto rides dick like a pro”

Rainblow 1 year ago

”BOBSTGIRLS: Marcela In Command”

”BOBSTGIRLS: Marcela In Command”

Zatube 1 year ago

Latex Sissy Anal Training

Latex Sissy Anal Training

xHamster 2 years ago

My Hottest Soapiest Shower POV Fat Cock Cumming

My Hottest Soapiest Shower POV Fat Cock Cumming

xHamster 1 year ago

Luxurious TRANSSEXUAL assistant unwraps down with masturbating and jizz shot

Luxurious TRANSSEXUAL assistant unwraps down with masturbating and jizz shot

TrannyGem 2 years ago

TGilrs CHALLENGE (round 16) - Amanda Lima 22 cm VS Raffaella

TGilrs CHALLENGE (round 16) - Amanda Lima 22 cm VS Raffaella

xHamster 3 years ago

Tgilrs Challenge (round 24) - Valesca Sargentely 25 Cm Vs

Tgilrs Challenge (round 24) - Valesca Sargentely 25 Cm Vs

getTranny 3 years ago

Young shemale takes one more giant cock as a challenge

Young shemale takes one more giant cock as a challenge

DrTuber 3 years ago

Tgilrs Challenge (round 28) - Cris 20 Cm Vs Luana Pacheco 16

Tgilrs Challenge (round 28) - Cris 20 Cm Vs Luana Pacheco 16

getTranny 3 years ago

Trans Girl Gives Step Sis a Big Dick Ride Challenge

Trans Girl Gives Step Sis a Big Dick Ride Challenge

FapHouse 1 year ago

Flashing in a Busy Carpark

68% HD 1:01 / 6:28

Flashing in a Busy Carpark

FapHouse 2 years ago

Transsexual Anal Challenge in Brazil - Episode #05

65% HD 1:01 / 26:02

Transsexual Anal Challenge in Brazil - Episode #05

FapHouse 5 years ago

Crossdress cosplay Rosalina dildos and panties

Crossdress cosplay Rosalina dildos and panties

FapHouse 6 years ago

Transsexual Anal Challenge in Brazil - Episode #10

Transsexual Anal Challenge in Brazil - Episode #10

FapHouse 4 years ago

Transsexual Sexy Anal Challenge in Brazil - Episode #01

HD 1:01 / 20:34

Transsexual Sexy Anal Challenge in Brazil - Episode #01

FapHouse 5 years ago

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

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

Zatube 1 year ago

”TRANSVR - Cutie Spite Ended Up Fucking Her Housemate”

”TRANSVR - Cutie Spite Ended Up Fucking Her Housemate”

ThePornstar 1 year ago

”Deeper: Assfucking-obsessed Haley Reed is pushed past her comfort zone”

”Deeper: Assfucking-obsessed Haley Reed is pushed past her comfort zone”

ThePornstar 1 year ago

”GROOBY.CLUB: TALYTA SOARES & MARCUS!”

”GROOBY.CLUB: TALYTA SOARES & MARCUS!”

StarWank 1 year ago

”BRAZILIAN TRANSSEXUALS: New Tranny Beautiful Babe Brenda Christal”

”BRAZILIAN TRANSSEXUALS: New Tranny Beautiful Babe Brenda Christal”

StarWank 1 year ago

”Huge dick bro gets a fantastic BJ from his sister”

”Huge dick bro gets a fantastic BJ from his sister”

ThePornstar 1 year ago

Tattooed trans Joey Stone suffers pussy stretching and deepthroating

Tattooed trans Joey Stone suffers pussy stretching and deepthroating

Yeswegays 1 year ago

Beautiful black MILF Misty Stone having erotic sex with TS Natassia Dreams

Beautiful black MILF Misty Stone having erotic sex with TS Natassia Dreams

Fapnado 4 years ago

”Swallowed: Angel Youngs’ Deepthroat Challenge”

”Swallowed: Angel Youngs’ Deepthroat Challenge”

ThePornstar 11 months ago

”Reality Kings: Competitive Couples Sexercise With Leana Lovings & JMac”

”Reality Kings: Competitive Couples Sexercise With Leana Lovings & JMac”

ThePornstar 1 year ago

19 20 21 22 23

3,033 results found

Related categories

Nipple Piercing Lollipop Edging Shaking Orgasm Milking Table WTF Piercing Freak Competition Braces Begging Laughing Jerking Off Tan Lines Perverted Kinky Gagging Tease Nerdy Premature Ejaculation

Narrow your search

try not to cum challenge jerk off challenge edging challenge cum challenge dildo challenge dont cum challenge anal challenge stroke challenge cock hero challenge joi challenge orgasm challenge jerk challenge edge challenge blowjob challenge do not cum challenge handjob challenge stranger challenge deepthroat challenge escape challenge no fap challenge

Categories Pornstars

Categories Pornstars

PornMD: A Porn Search Engine.

Parents

Pornmd.com uses the "Restricted To Adults" (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Pornmd.com. All rights reserved.

© 2026 Pornmd.com. All rights reserved.