Challenge Videos - Trans (3,015)

Nobody would have guessed I view like this under my work clothes

Nobody would have guessed I view like this under my work clothes

Gayhub 8 months ago

Renata VS Bella (Tgirls Extreme Challenge)

Renata VS Bella (Tgirls Extreme Challenge)

xHamster 3 years ago

TGilrs CHALLENGE (round 41) - Chris Christal 22 cm VS Dafne

TGilrs CHALLENGE (round 41) - Chris Christal 22 cm VS Dafne

xHamster 3 years ago

Experienced Shemale Takes On BBC Challenge in Explicit Taste Game

Experienced Shemale Takes On BBC Challenge in Explicit Taste Game

PumpJap 3 months ago

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

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

Fapnow 1 year ago

Cock Confusion Challenge II

Cock Confusion Challenge II

Eporner 5 months ago

Cisgender gets ass fucked by this TS

Cisgender gets ass fucked by this TS

ALOTPorn 4 weeks ago

Jennyfer VS Rafaella (Tgirls Extreme Challenge)

Jennyfer VS Rafaella (Tgirls Extreme Challenge)

xHamster 3 years ago

TGilrs CHALLENGE (round 23) - Marla 25 Cm VS Daniela 20 Cm

TGilrs CHALLENGE (round 23) - Marla 25 Cm VS Daniela 20 Cm

BeMyHole 2 years ago

Here we goes the CHALLENGE FIGHT, on ring Rebecca VS

Here we goes the CHALLENGE FIGHT, on ring Rebecca VS

xHamster 2 years ago

How Long Can You Watch Without Nutting Like A Fucking Champ

How Long Can You Watch Without Nutting Like A Fucking Champ

Jizzberry 9 months ago

Big Load TGilrs Challenge

Big Load TGilrs Challenge

BeMyHole 3 years 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 2 years ago

Transexual anal challenge - Episode #10

Transexual anal challenge - Episode #10

xHamster 2 years ago

”Aria Kai challenged by Brickzilla”

”Aria Kai challenged by Brickzilla”

TransHero 1 month ago

cock confusion challenge

cock confusion challenge

Eporner 5 months ago

TGilrs CHALLENGE (round 09) - Luana 20 cm VS Barbara 21 cm

TGilrs CHALLENGE (round 09) - Luana 20 cm VS Barbara 21 cm

xHamster 3 years ago

$Сhallenge - can you not touch the dick.\RUS$ 77% HD 3:48

Сhallenge - can you not touch the dick.\RUS

aShemaleTube 3 years ago

Here we goes the CHALLENGE FIGHT, on ring Vivian VS Taissa

Here we goes the CHALLENGE FIGHT, on ring Vivian VS Taissa

xHamster 2 years ago

Another Straight Boy in Conversion Challenge

Another Straight Boy in Conversion Challenge

Tranny.one 3 years ago

Challenging my neighbors- Cum rain, pee

Challenging my neighbors- Cum rain, pee

TransTube.tv 1 year ago

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

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

xHamster 2 years ago

Geovane VS Renata (Tgirls Extreme Challenge)

Geovane VS Renata (Tgirls Extreme Challenge)

xHamster 3 years ago

”Adorable massage hot girl helps an old man with his gonads”

”Adorable massage hot girl helps an old man with his gonads”

ThePornstar 1 year ago

TGilrs CHALLENGE (round 33) - Raphaella Ferrari 23 cm VS

TGilrs CHALLENGE (round 33) - Raphaella Ferrari 23 cm VS

xHamster 3 years ago

Cumshots TGilrs Challenge

Cumshots TGilrs Challenge

BeMyHole 3 years ago

Edging challenge

Edging challenge

Eporner 4 years ago

Bigtits Here We Goes The CHALLENGE FIGHT 208, On Ring Flavia VS Mireja

Bigtits Here We Goes The CHALLENGE FIGHT 208, On Ring Flavia VS Mireja

BeMyHole 2 years ago

Multi Orgasm Challenge

Multi Orgasm Challenge

Eporner 4 years ago

FapFantastika 11

FapFantastika 11

Eporner 4 weeks ago

TGilrs CHALLENGE - Valesca Sargentely 22 Cm

TGilrs CHALLENGE - Valesca Sargentely 22 Cm

BeMyHole 2 years ago

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

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

xHamster 2 years ago

Hentai NNN Challenge Day 19: Trap VS Reverse Trap (Steins;Gate)"

Hentai NNN Challenge Day 19: Trap VS Reverse Trap (Steins;Gate)"

HentaiGem 3 years 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

Cute Femboy with Big Ass Makes a Jerk Off Challenge Experiment

Cute Femboy with Big Ass Makes a Jerk Off Challenge Experiment

xHamster 9 months ago

FERNANDA 20 cm VS HANN 22 cm (TGIRLS CHALLENGE 120)

FERNANDA 20 cm VS HANN 22 cm (TGIRLS CHALLENGE 120)

xHamster 3 years ago

Tgirl Fuck Man And Sucking Act Here We Goes The CHALLENGE FIGHT, On Ring Marcella VS Amanda

Tgirl Fuck Man And Sucking Act Here We Goes The CHALLENGE FIGHT, On Ring Marcella VS Amanda

BeMyHole 2 years ago

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

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

xHamster 3 years ago

Cock Hungry Trannies Challenge

Cock Hungry Trannies Challenge

BeMyHole 3 years ago

TGilrs CHALLENGE (round 34) - Melissa Pozzi 26 cm VS Renata

TGilrs CHALLENGE (round 34) - Melissa Pozzi 26 cm VS Renata

xHamster 3 years ago

Natally VS Arianna (Tgirls Extreme Challenge)

Natally VS Arianna (Tgirls Extreme Challenge)

BeMyHole 2 years ago

TGIRLS XXX - Pop The Balloon - Trans Edition

TGIRLS XXX - Pop The Balloon - Trans Edition

Fapnado 1 month ago

Kessie VS Victoria (Tgirls Extreme Challenge)

Kessie VS Victoria (Tgirls Extreme Challenge)

xHamster 3 years ago

Post Orgasm Cum Milking Jessica Bloom Big Trans Dick Milking Machine

Post Orgasm Cum Milking Jessica Bloom Big Trans Dick Milking Machine

xHamster 1 year 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

Stroking challenger

Stroking challenger

aShemaleTube 6 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 9 months ago

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

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

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

BeMyHole 2 years 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

xHamster 3 years ago

”Resident Head Fuck”

”Resident Head Fuck”

TransHero 3 weeks ago

Ts babe reach orgasm by jerking her stiff cock

Ts babe reach orgasm by jerking her stiff cock

VikiPorn 2 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 Isabelli VS Luana

Here we goes the CHALLENGE FIGHT, on ring Isabelli VS Luana

xHamster 2 years ago

Big Dick Melissa Pozzi & Renata Hot Videos Challenge

Big Dick Melissa Pozzi & Renata Hot Videos Challenge

BeMyHole 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

BeMyHole 1 year ago

German amateur shemale destroys her ass and cums hard

German amateur shemale destroys her ass and cums hard

xHamster 5 years ago

Hankeys Toys Tryouts - L Big Daddy

Hankeys Toys Tryouts - L Big Daddy

xHamster 10 months ago

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

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

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

TRANNY CUM COMPILATION ENDURANCE DEFIANCE - Can u make it to the end ?

TRANNY CUM COMPILATION ENDURANCE DEFIANCE - Can u make it to the end ?

ShemaleSin 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 3 years 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

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

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

xHamster 2 years ago

30 mins no break fellate spitroast contest!

30 mins no break fellate spitroast contest!

TrannyGem 2 months ago

Not Quite Straight Vol. 2 PMV Challenge

Not Quite Straight Vol. 2 PMV Challenge

Eporner 2 years ago

Fishnet Femboy bounces his Fat Ass on Big Dildos

Fishnet Femboy bounces his Fat Ass on Big Dildos

xHamster 3 months ago

Str8 Hunk Test (T-Girls, Dick)

Str8 Hunk Test (T-Girls, Dick)

BigTitsLust 3 years 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 2 years ago

Isa VS HERSELF (Tgirls Extreme Challenge)

Isa VS HERSELF (Tgirls Extreme Challenge)

xHamster 3 years 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 7 months ago

Jerk Off Instructions- Lovely emo stiffy mom helps you de-strain after a stiff day at work

Jerk Off Instructions- Lovely emo stiffy mom helps you de-strain after a stiff day at work

TrannyGem 2 years ago

Straight Boy Test (T-girls, Shlong)

Straight Boy Test (T-girls, Shlong)

Dafreeporn 4 years ago

Here We Goes The CHALLENGE FIGHT 218, On Ring Luana VS Ingrid

Here We Goes The CHALLENGE FIGHT 218, On Ring Luana VS Ingrid

BeMyHole 2 years ago

Petite Trans Nixi Leon Loves Feeling BBC

Petite Trans Nixi Leon Loves Feeling BBC

xHamster 1 year ago

WVM - PART 151 - Don't Cum Challenge #4 By MissKitty2K

WVM - PART 151 - Don't Cum Challenge #4 By MissKitty2K

xHamster 1 year ago

FapFantastika 9

FapFantastika 9

Eporner 1 month ago

Tranny Tops Guy TGilrs CHALLENGE - Fernanda Vasconcelos 22 Cm VS

Tranny Tops Guy TGilrs CHALLENGE - Fernanda Vasconcelos 22 Cm VS

BeMyHole 3 years ago

Ruby Faith Spermicide Challenge

Ruby Faith Spermicide Challenge

FukXL 7 months ago

Multi Orgasm Challenge

Multi Orgasm Challenge

BeMyHole 3 years ago

TGilrs CHALLENGE (round 15) - Natalia Rodrigues 23 cm VS

TGilrs CHALLENGE (round 15) - Natalia Rodrigues 23 cm VS

xHamster 3 years ago

BEST OF SCOUT LONDON TRANS GIRL COMPILATION

BEST OF SCOUT LONDON TRANS GIRL COMPILATION

FapCat 3 years ago

TGilrs CHALLENGE (round 05) - Daniela Colucci 20 cm VS Luana

TGilrs CHALLENGE (round 05) - Daniela Colucci 20 cm VS Luana

xHamster 3 years ago

Cocotranse Challenge Game with Rules Horny Crossdresser

Cocotranse Challenge Game with Rules Horny Crossdresser

aShemaleTube 5 years ago

Nylon Try Not To Cum Challenge

Nylon Try Not To Cum Challenge

Tranny.one 4 years ago

Trans Fetishists Janelle Fennec And Melanie Brooks Having Anal Sex

Trans Fetishists Janelle Fennec And Melanie Brooks Having Anal Sex

Eporner 9 months ago

Mature T-girl MILF Strokes Monster Cock for Messy Cumshot POV - sexcamts.com

Mature T-girl MILF Strokes Monster Cock for Messy Cumshot POV - sexcamts.com

Sheshaft 4 months ago

”SchoolPOV: Two Sexy Teen Cunts For The Taking With Alexa Flexy & Alyssa Bounty”

”SchoolPOV: Two Sexy Teen Cunts For The Taking With Alexa Flexy & Alyssa Bounty”

ThePornstar 5 months ago

Try Not To Cum Challenge PT 2 ! StupidBratPiss

Try Not To Cum Challenge PT 2 ! StupidBratPiss

Eporner 5 years ago

JOI- Adorable Goth Cock Mommy Helps you De-stress after a Hard Day at Work

JOI- Adorable Goth Cock Mommy Helps you De-stress after a Hard Day at Work

TatBabes 1 year ago

Sissy Jessica Bloom Eats Her Own Cum off a Cake! - Edging Sounding And Cumplay

Sissy Jessica Bloom Eats Her Own Cum off a Cake! - Edging Sounding And Cumplay

xHamster 1 year ago

TGilrs CHALLENGE (round 02) - Gloria Voguel 22 Cm VS

TGilrs CHALLENGE (round 02) - Gloria Voguel 22 Cm VS

BeMyHole 2 years ago

JOI challenge for gooners and addicts

JOI challenge for gooners and addicts

Eporner 2 months ago

Rafaella VS Isabel (Tgirls Extreme Challenge)

Rafaella VS Isabel (Tgirls Extreme Challenge)

BeMyHole 2 years ago

TGilrs CHALLENGE (round 10) - Tiffany Kawasaky 23 cm VS

TGilrs CHALLENGE (round 10) - Tiffany Kawasaky 23 cm VS

xHamster 3 years ago

Tgilrs Challenge (round 23) - Marla 25 Cm Vs Daniela 20 Cm

Tgilrs Challenge (round 23) - Marla 25 Cm Vs Daniela 20 Cm

getTranny 3 years ago

Sissy Anal Training

Sissy Anal Training

xHamster 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

Fresh widow tested a tgirl cock

Fresh widow tested a tgirl cock

Fapnado 4 years ago

Bigtits Here We Goes The CHALLENGE FIGHT 187, On Ring Victoria VS Andrea

Bigtits Here We Goes The CHALLENGE FIGHT 187, On Ring Victoria VS Andrea

BeMyHole 2 years ago

Naughty And Nice Shemale Feeling Her Cock

Naughty And Nice Shemale Feeling Her Cock

aShemaleTube 1 year 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

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

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

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 2 years ago

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

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

xHamster 2 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

Tranny.one 1 year ago

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

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

xHamster 2 years ago

Big Load And Huge Cock TGilrs CHALLENGE (round 18) - Amanda Lima 23 Cm VSCarolina

Big Load And Huge Cock TGilrs CHALLENGE (round 18) - Amanda Lima 23 Cm VSCarolina

BeMyHole 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”

Rainblow 6 months ago

Take my Compilation, Creampie & Cumshot Challenge, All under Femdom Dominance

Take my Compilation, Creampie & Cumshot Challenge, All under Femdom Dominance

XXXShake 3 years ago

Here we goes the CHALLENGE FIGHT 190, on ring Valeria VS Anna

Here we goes the CHALLENGE FIGHT 190, on ring Valeria VS Anna

xHamster 2 years ago

Discover the Ultimate Guide to Pleasure with Wendy: A Realistic Doll Experience!

Discover the Ultimate Guide to Pleasure with Wendy: A Realistic Doll Experience!

JuicyVid 3 weeks ago

100 Push up Challenge Live Purup

100 Push up Challenge Live Purup

xHamster 2 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

aShemaleTube 6 months ago

3 HOUR TRY NOT TO CUM EDGING CHALLENGE FULL MOVIE

3 HOUR TRY NOT TO CUM EDGING CHALLENGE FULL MOVIE

YouPorn Unknown

Female or Shemale? guess it! (pics slideshow)

Female or Shemale? guess it! (pics slideshow)

XVideos 4 years ago

luuv. alice and lucien fulfill a reality show challenge

luuv. alice and lucien fulfill a reality show challenge

PornOne 1 month ago

TGilrs CHALLENGE (round 19) - Fernanda Vasconcelos 22 cm VS

TGilrs CHALLENGE (round 19) - Fernanda Vasconcelos 22 cm VS

xHamster 3 years ago

Korra Del Rio Isabella Sorrenti Fuck

Korra Del Rio Isabella Sorrenti Fuck

xHamster 1 year 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

1 2 3 4 5

3,015 results found

Related categories

Milking Table Nipple Piercing Freak Hazing Edging Braces WTF Piercing Gagging Locker Room Training Cheerleader Weird Screaming Orgasm Stretching Messy Competition Instructions Fisting Punk

Narrow your search

edging challenge jerk off challenge orgasm challenge edge challenge try not to cum challenge cum challenge dildo challenge anal challenge dont cum challenge cock hero challenge joi challenge stroke challenge nnn challenge do not cum challenge backdoor challenge blowjob challenge jerk challenge handjob challenge no fap challenge melone challenge

Categories Pornstars

Categories Pornstars

Legal

Terms of Service Privacy Statement Statement of Responsibility Notice and Action Policy (Link Removal) DMCA / Copyright Acceptable Content Policy Digital Services Act 2257

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.