Challenge Videos - Trans (4,349)

Foreskin Covered Cum & Piss Challenge - Never Retracting

51% HD 0:39 / 6:16

Foreskin Covered Cum & Piss Challenge - Never Retracting

FapHouse 6 months ago

Sucks And Thick Cock Here We Goes The CHALLENGE FIGHT 212, On Ring Hellen VS Milla

Sucks And Thick Cock Here We Goes The CHALLENGE FIGHT 212, On Ring Hellen VS Milla

BeMyHole 2 years ago

Evil Mommy Catheter Incontinence Challenge Sissy

Evil Mommy Catheter Incontinence Challenge Sissy

BeMyHole 3 years ago

Tgilrs Challenge (round 20) - Veronika Havenna 25 Cm Vs

Tgilrs Challenge (round 20) - Veronika Havenna 25 Cm Vs

getTranny 3 years ago

Kink Trans Danni Daniels Gia DiMarco Primary Evolution Quest Human TS Seduce Destroy

Kink Trans Danni Daniels Gia DiMarco Primary Evolution Quest Human TS Seduce Destroy

Yeswegays 2 days ago

Kendra James and Abigail Mac:Catwoman and Batwoman fall for the Futa stone! HD

HD 0:11 / 39:41

Kendra James and Abigail Mac:Catwoman and Batwoman fall for the Futa stone! HD

Clips4sale 3 years ago

Obedient Femboy Sissy is getting desperate to jizz - Day three

Obedient Femboy Sissy is getting desperate to jizz - Day three

TransTube.tv 1 year ago

CLARISSA 18 cm VS ESMERALDA 20 cm - (TGIRLS CHALLENGE 125)

CLARISSA 18 cm VS ESMERALDA 20 cm - (TGIRLS CHALLENGE 125)

xHamster 3 years ago

Super intense anal sex with TS Leah Hayes

Super intense anal sex with TS Leah Hayes

Wankoz 2 weeks ago

Ab065 Happy Chinese New Year-red Food Challenge And Nice Blow Job 6 Min - Abby Kitty

Ab065 Happy Chinese New Year-red Food Challenge And Nice Blow Job 6 Min - Abby Kitty

PornUse 7 months ago

Wolf Wagners Dirty Jungle Party 3: Lively Threesome Finale

Wolf Wagners Dirty Jungle Party 3: Lively Threesome Finale

Some.Porn 1 year ago

Beautiful post-op swallows my seed

53% HD 0:39 / 13:39

Beautiful post-op swallows my seed

FapHouse 3 years ago

Here we goes the CHALLENGE FIGHT, on ring Luana Vs Ingrid

Here we goes the CHALLENGE FIGHT, on ring Luana Vs Ingrid

xHamster 3 years ago

It’s Just Curiosity, Right? Pre-Gay Reflex Check

It’s Just Curiosity, Right? Pre-Gay Reflex Check

Clips4sale 7 months ago

TGIRL DOUBLE FISTED AND PEGGED WITH HUGE STRAPON

68% HD 0:10 / 20:40

TGIRL DOUBLE FISTED AND PEGGED WITH HUGE STRAPON

LoyalFans 2 years ago

Futanari Ashe Gushes After Being Caught By Her Milf Mentor

Futanari Ashe Gushes After Being Caught By Her Milf Mentor

JuicyTrans 3 weeks ago

Sissy Joyce Challenge

Sissy Joyce Challenge

Pornzona 3 months ago

Hellish Aroma Trapdoor Part 4

Hellish Aroma Trapdoor Part 4

Clips4sale 10 months ago

Hide From My Parents

Hide From My Parents

Some.Porn 2 years ago

Riding ONLY (Anal Masturbation Instructional)

57% HD 0:10 / 19:18

Riding ONLY (Anal Masturbation Instructional)

LoyalFans 3 months ago

Fallen Makina and the City of Ruins sex public cheating milf hero fap challenge sex ahegao hentai blowjob big tits 3d

Fallen Makina and the City of Ruins sex public cheating milf hero fap challenge sex ahegao hentai blowjob big tits 3d

Juicexxx 2 months ago

13 Seconds Sissygasm Ruined Premature Huge Cumshots Buttplug Chastity Cage

13 Seconds Sissygasm Ruined Premature Huge Cumshots Buttplug Chastity Cage

JuicyTrans 3 weeks ago

Trans Male Jade Venus Fucks His Female GFs Olivia Jay & Little Puck

Trans Male Jade Venus Fucks His Female GFs Olivia Jay & Little Puck

Wankoz 2 weeks ago

Danika Deep vs KaneVision Competitive Wrestling

Danika Deep vs KaneVision Competitive Wrestling

Clips4sale 3 years ago

Izzy Wilde challenges her girlfriend Cami Strella to a steamy sex battle

Izzy Wilde challenges her girlfriend Cami Strella to a steamy sex battle

Fucker 3 months ago

Rosy Vs Beatrice (ts Challenge New Edition)

Rosy Vs Beatrice (ts Challenge New Edition)

getTranny 3 years ago

Mouth Trap Challenge

Mouth Trap Challenge

AbTranny 3 days ago

Korra Del Rio Isabella Sorrenti Fuck

Korra Del Rio Isabella Sorrenti Fuck

xHamster 2 years ago

This Will Blow Your Mind: Vaniity Is Back

This Will Blow Your Mind: Vaniity Is Back

xHamster 2 months ago

”Wedding Crash Challenge Leads To A Day Of Horny Wet Cunts”

”Wedding Crash Challenge Leads To A Day Of Horny Wet Cunts”

TransHero 6 months ago

Ab065 Happy Chinese New Year-red Food Challenge And Nice Blow Job - Abby Kitty

Ab065 Happy Chinese New Year-red Food Challenge And Nice Blow Job - Abby Kitty

AbTranny 1 month ago

Exposed Sissy Challenge

HD 0:10 / 11:03

Exposed Sissy Challenge

LoyalFans 3 years ago

Sleepover Fun

Some.Porn 2 years ago

TGilrs CHALLENGE - Veronika Havenna 25 Cm

TGilrs CHALLENGE - Veronika Havenna 25 Cm

BeMyHole 2 years ago

ADULT TIME Sexy T Chick Izzy Wilde Challenges Her GF Cam

ADULT TIME Sexy T Chick Izzy Wilde Challenges Her GF Cam

Sheshaft 5 days ago

Goddess JOI with Muscle worship and Latex ASMR

HD 0:10 / 11:22

Goddess JOI with Muscle worship and Latex ASMR

LoyalFans 8 months ago

Here we goes the CHALLENGE FIGHT 187, on ring Victoria VS Andrea

Here we goes the CHALLENGE FIGHT 187, on ring Victoria VS Andrea

xHamster 3 years 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!

AbTranny 1 month ago

WHO NEEDS FLYING TRUCKS WHEN WE HAVE EDGING MACHINES?

WHO NEEDS FLYING TRUCKS WHEN WE HAVE EDGING MACHINES?

Transvids.tv 11 months ago

I Hit It Last

Premium HD 24:01

TransAngels 6 years ago

Someone come behind me and fuck my hot pussy

Someone come behind me and fuck my hot pussy

Pornzona 1 week ago

Teen (18+) Risks Everything For Fucking With Trans Principal

Teen (18+) Risks Everything For Fucking With Trans Principal

BallsNBoobs 2 months ago

JOI Challenge: Show me what a good wanker you are, cum in a minute! GERMAN DEUTSCH

JOI Challenge: Show me what a good wanker you are, cum in a minute! GERMAN DEUTSCH

Clips4sale 1 year ago

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

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

xHamster 3 years ago

two Lesbian Cuties Sucking Tgirl Huge Rod Cumming

two Lesbian Cuties Sucking Tgirl Huge Rod Cumming

PornFreeNow 3 days ago

”Katy Leon - Monstercocking Katy Leon - Trans Porn”

”Katy Leon - Monstercocking Katy Leon - Trans Porn”

429Men 5 months ago

Extreme Double Fisting and Monster Strapon Pounding in a Shemale's Ass

Extreme Double Fisting and Monster Strapon Pounding in a Shemale's Ass

XXXShake 2 years ago

TGIRLS XXX - Pop The Balloon - Trans Edition

TGIRLS XXX - Pop The Balloon - Trans Edition

Fapnado 6 months ago

tgilrs challenge fight 139 , on ring susanna h. vs tempires t.

tgilrs challenge fight 139 , on ring susanna h. vs tempires t.

SukaPorn 2 years ago

Mei's Futanari Cock Takes on HoneyChan's No Nut November Challenge

Mei's Futanari Cock Takes on HoneyChan's No Nut November Challenge

Jizzberry 3 years ago

Transexual Anal Challenge in Brazil - Episode #19

HD 1:01 / 20:49

Transexual Anal Challenge in Brazil - Episode #19

FapHouse 5 years ago

Bigtits TGilrs CHALLENGE - Valesca Sargentely

Bigtits TGilrs CHALLENGE - Valesca Sargentely

BeMyHole 3 years ago

TGilrs CHALLENGE (round 20) - Veronika Havenna 25 cm VS

TGilrs CHALLENGE (round 20) - Veronika Havenna 25 cm VS

xHamster 3 years ago

Ride Dildo Challenges 2

Ride Dildo Challenges 2

xHamster 10 months ago

tgilrs challenge fight 67 , on ring chrystal vs larissa a.

tgilrs challenge fight 67 , on ring chrystal vs larissa a.

SukaPorn 2 years ago

TRANSFIXED Casey Kisses Having Anal Sex With A Milf And A Big Cocked Fucker

TRANSFIXED Casey Kisses Having Anal Sex With A Milf And A Big Cocked Fucker

Eporner 1 year ago

Premature-Ejaculation or Chastity Challenge

56% 0:28 / 10:31

Premature-Ejaculation or Chastity Challenge

Clips4sale 3 years ago

Crossdress Iskra and here panties

Crossdress Iskra and here panties

xHamster 1 year ago

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - CLIP 4 OF 5 - WMV

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - CLIP 4 OF 5 - WMV

Clips4sale 1 year ago

MILF Quest: 1

Some.Porn 10 months ago

Maha the Russian Trans MILF (part 2 of 2)

Maha the Russian Trans MILF (part 2 of 2)

Dafreeporn 2 weeks ago

Dont Blow It Defiance Can - TS Jenby Doll Finish Me in Time

Dont Blow It Defiance Can - TS Jenby Doll Finish Me in Time

SortPorn 2 weeks 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

Aylla Gattina Vs Carla Tavares (ts Challenge New Edition)

Aylla Gattina Vs Carla Tavares (ts Challenge New Edition)

getTranny 3 years ago

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

65% HD 0:39 / 6:52

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

FapHouse 5 months ago

Ladyboy Fucks TGilrs CHALLENGE - Rebecca 24 Cm VS Walleska

Ladyboy Fucks TGilrs CHALLENGE - Rebecca 24 Cm VS Walleska

BeMyHole 3 years ago

Groobygirls Bareback Only for Belle Adams

51% HD 0:39 / 22:18

Groobygirls Bareback Only for Belle Adams

FapHouse 6 months ago

Stunning Pietra Raw Fucks Her Lucky Fella

Stunning Pietra Raw Fucks Her Lucky Fella

xHamster 1 month ago

Latina teen shemale drilled bareback

65% HD 1:01 / 27:15

Latina teen shemale drilled bareback

FapHouse 8 years ago

Secret Sissy Winter Challenge

Secret Sissy Winter Challenge

IWantClips 1 year ago

”GROOBYVR - The Fan Fuck With Lola”

”GROOBYVR - The Fan Fuck With Lola”

IFuckedYourGF 4 weeks ago

brazilian bombshell luna alvier loves bbc

55% HD 0:30 / 34:09

brazilian bombshell luna alvier loves bbc

AnalVids 2 years ago

Shemale Doctor Fucking Max Asshole With Huge Cock And Collecting Semen

Shemale Doctor Fucking Max Asshole With Huge Cock And Collecting Semen

xHamster 1 month ago

ADRIANA 20 Cm VS BEATRICE 24 Cm - (transgender princesses defiance 131)

ADRIANA 20 Cm VS BEATRICE 24 Cm - (transgender princesses defiance 131)

TransTube.tv 11 months ago

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

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

BeMyHole 3 years ago

It's anal time, wake up! - Eva Maxim and Jade Venus

It's anal time, wake up! - Eva Maxim and Jade Venus

Fapnado 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

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

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

SortPorn 1 year ago

Beautiful Post-Op Swallows My Seed

62% HD 0:10 / 13:40

Beautiful Post-Op Swallows My Seed

LoyalFans 3 years 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 1 year ago

Brazilian And T-girl Here We Goes The CHALLENGE FIGHT 211, On Ring Mireja VS Flavia

Brazilian And T-girl Here We Goes The CHALLENGE FIGHT 211, On Ring Mireja VS Flavia

BeMyHole 2 years ago

Leticia VS Carolina (Tgirls Extreme Challenge)

Leticia VS Carolina (Tgirls Extreme Challenge)

BeMyHole 3 years ago

Petite Trans Nixi Leon Loves Feeling BBC

Petite Trans Nixi Leon Loves Feeling BBC

xHamster 1 year ago

Headscissoring Challenge Turned Erotic: Starring Aria James (Alternate Angle)

66% HD 0:29 / 10:30

Headscissoring Challenge Turned Erotic: Starring Aria James (Alternate Angle)

Clips4sale 2 years ago

ABT250116 20cm Dildo Challenge -20公分假陽具大挑戰

ABT250116 20cm Dildo Challenge -20公分假陽具大挑戰

aShemaleTube 2 months ago

Maha the Russian Trans MILF (part 2 of 2)

Maha the Russian Trans MILF (part 2 of 2)

xHamster 3 weeks ago

Car Foot Fetish

Car Foot Fetish

FapHouse 10 months ago

Real Gamers Only Pause For Cock

Real Gamers Only Pause For Cock

Some.Porn 1 year ago

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - FULL VERSION - MP4

61% 0:31 / 27:27

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - FULL VERSION - MP4

Clips4sale 1 year 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 month ago

Hung Stud Takes It Up The Ass From Smokin Hot TS Nataly Souza

Hung Stud Takes It Up The Ass From Smokin Hot TS Nataly Souza

XXXShake 10 months ago

Here we goes the CHALLENGE FIGHT 189, on ring Andrea VS Vanity

Here we goes the CHALLENGE FIGHT 189, on ring Andrea VS Vanity

xHamster 3 years ago

Sabrina Rios Vs Ariadny Oliver (ts Challenge New Edition)

Sabrina Rios Vs Ariadny Oliver (ts Challenge New Edition)

getTranny 3 years ago

Sissygasm Challenge Day 1 - Sissy Trap Boy Rides Dildo

Sissygasm Challenge Day 1 - Sissy Trap Boy Rides Dildo

Itsrealamateurs 1 month ago

Arm Strength Challenge

Arm Strength Challenge

FapHouse 10 months ago

”TGIRLS XXX - Pop The Balloon - Tranny Edition”

”TGIRLS XXX - Pop The Balloon - Tranny Edition”

Trashreality 4 months ago

Can anal stimulation bring a closed femboy to orgasm?

Can anal stimulation bring a closed femboy to orgasm?

xHamster 2 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

TGilrs CHALLENGE (round 32) - Valesca Sargentely 22 cm VS

TGilrs CHALLENGE (round 32) - Valesca Sargentely 22 cm VS

xHamster 3 years ago

Erika VS Victoria (Tgirls Extreme Challenge)

Erika VS Victoria (Tgirls Extreme Challenge)

xHamster 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

”Step Mom's Hard Cock Workout - Millie Morgan & Jade Maris”

”Step Mom's Hard Cock Workout - Millie Morgan & Jade Maris”

TransHero 6 months ago

Priscilla VS Jennyfer (Tgirls Extreme Challenge)

Priscilla VS Jennyfer (Tgirls Extreme Challenge)

xHamster 3 years ago

Liquid silicone encasement bondage

HD 0:10 / 1:01:34

Liquid silicone encasement bondage

LoyalFans 3 months ago

”Unshaved muff teen Riley gets deep-dicked by a black dick”

”Unshaved muff teen Riley gets deep-dicked by a black dick”

ThePornstar 1 year ago

Gorgeous Trans Stepmom Banged By Muscle Hunks

Gorgeous Trans Stepmom Banged By Muscle Hunks

xHamster 4 years ago

Gender Bender Animation: Swipe Challenge

Gender Bender Animation: Swipe Challenge

HentaiGem 3 years ago

Car Foot Fetish

66% HD 1:01 / 5:33

Car Foot Fetish

FapHouse 10 months ago

Icky Sticky Animation Challenge Feb 2025

Icky Sticky Animation Challenge Feb 2025

3DPornDude 1 year ago

Transsexual anal challenge in Brazil - Episode #11

Transsexual anal challenge in Brazil - Episode #11

xHamster 2 years ago

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - FULL VERSION - WMV

74% 0:31 / 27:29

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - FULL VERSION - WMV

Clips4sale 1 year ago

Kink Trans Danni Daniels Gia DiMarco Primary Evolution Quest Human TS Seduce Destroy

Kink Trans Danni Daniels Gia DiMarco Primary Evolution Quest Human TS Seduce Destroy

FetishShrine 1 day ago

POV sex with ebony girlfriend Olivia Jayy

POV sex with ebony girlfriend Olivia Jayy

xDegu 3 days ago

Big Dick Trans Domme Stroke-for-stroke Masturbation Challenge 10-minutes With Explosive Finish

Big Dick Trans Domme Stroke-for-stroke Masturbation Challenge 10-minutes With Explosive Finish

AbTranny 1 week ago

Trans Latex Mamma JOI Gooner

Trans Latex Mamma JOI Gooner

ShemaleSin 2 years ago

Akali solo this massive cock

Akali solo this massive cock

xHamster 3 months ago

Spitroasted in sexy lingerie by two big dildos

Spitroasted in sexy lingerie by two big dildos

Pornzona 3 months ago

extreme market challenge: part 2 — huge ball limit and pumpkin for dumb sissy [3-part series]

extreme market challenge: part 2 — huge ball limit and pumpkin for dumb sissy [3-part series]

PornBox 2 weeks ago

Il contratto da Sissy - The Sissy's slut contract #2 (MOBILE VERSION WMV)

HD 0:11 / 35:01

Il contratto da Sissy - The Sissy's slut contract #2 (MOBILE VERSION WMV)

Clips4sale 2 years ago

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

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

Yeswegays 3 years ago

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