Challenge Videos - Trans (3,731)

Transexual anal challenge - Episode #08

Transexual anal challenge - Episode #08

xHamster 2 years ago

Petite Trans Nixi Leon Loves Feeling BBC

Petite Trans Nixi Leon Loves Feeling BBC

xHamster 1 year ago

Transexual anal challenge in Brazil - Episode #19

Transexual anal challenge in Brazil - Episode #19

xHamster 2 years ago

Temptation and steamy thrill with transbabe Morgan Bailey at the bar

Temptation and steamy thrill with transbabe Morgan Bailey at the bar

VikiPorn 4 months ago

Sissy Quiz - Sissification Test for Curious Submissive, Panty-Boy, Crossdresser or Cock-Whore - Femdom POV Clip by Leda von Thrill - HD Video MP4 1920 x 1080p

33% HD 0:18 / 24:11

Sissy Quiz - Sissification Test for Curious Submissive, Panty-Boy, Crossdresser or Cock-Whore - Femdom POV Clip by Leda von Thrill - HD Video MP4 1920 x 1080p

Clips4sale 2 years ago

desi bhabhi showing boobs in suit salwar hot sil satin dress bhabhi big tits

desi bhabhi showing boobs in suit salwar hot sil satin dress bhabhi big tits

xHamster 11 months ago

The Tight Hole of the Banana Tree Is Delicious

59% HD 1:01 / 6:05

The Tight Hole of the Banana Tree Is Delicious

FapHouse 6 months ago

TGirl Nancy and Catherine TESTS OF STRENGTH HIDEF

HD 0:15 / 10:02

TGirl Nancy and Catherine TESTS OF STRENGTH HIDEF

Clips4sale 1 year ago

”The tennis match turns into a steamy threeway with Jewelz, Eva, & Emma”

”The tennis match turns into a steamy threeway with Jewelz, Eva, & Emma”

Rainblow 1 year ago

Rescued Tiny's Reward: Thanking a Friendly FtM Giant by Worshipping His Pussy and Clit - POV - Jaq Quicksilver -720p mp4

HD 0:27 / 10:57

Rescued Tiny's Reward: Thanking a Friendly FtM Giant by Worshipping His Pussy and Clit - POV - Jaq Quicksilver -720p mp4

Clips4sale 8 months ago

Ts Babi Antonella traps and blindfold Hex and have lots of fun with him (1080p ENG-sub) Trans Woman - Trans Fucking - Trans Anal - Trans Domination - Trans Blowjob - Trans Ass Licking

61% HD 0:25 / 22:57

Ts Babi Antonella traps and blindfold Hex and have lots of fun with him (1080p ENG-sub) Trans Woman - Trans Fucking - Trans Anal - Trans Domination - Trans Blowjob - Trans Ass Licking

Clips4sale 8 months 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

TGilrs CHALLENGE (round 14) - Fernanda Vasconcelos 22 cm VS

TGilrs CHALLENGE (round 14) - Fernanda Vasconcelos 22 cm VS

xHamster 3 years ago

TGIRLPORNSTAR: Adriana Rodrigues & Natalia Trans & Dante

TGIRLPORNSTAR: Adriana Rodrigues & Natalia Trans & Dante

xHamster 9 months ago

Sheena Shaw in Extra Evil Parts, Scene #01

Sheena Shaw in Extra Evil Parts, Scene #01

AbXXX 2 years ago

”Titty Jessy Dubai booty drilled by sexy stud Jessy Dubai”

”Titty Jessy Dubai booty drilled by sexy stud Jessy Dubai”

LesbianBliss 1 month ago

Sissy Shopping Challenge

Sissy Shopping Challenge

LoyalFans 2 years ago

2022 Christmas Cum Eating Challenge CEI

2022 Christmas Cum Eating Challenge CEI

xHamster 3 years ago

ADULT TIME - Sexy T-Girl Izzy Wilde Challenges Her GF Cami Strella To Sex Battle To Settle Argument!

ADULT TIME - Sexy T-Girl Izzy Wilde Challenges Her GF Cami Strella To Sex Battle To Settle Argument!

Fapcat 1 year ago

Isabelli Potter VS Luana (TS CHALLENGE NEW EDITION)

Isabelli Potter VS Luana (TS CHALLENGE NEW EDITION)

BeMyHole 2 years ago

Challenging My Husband to a Blowjob with Andres Soldier's Monster Cock

Challenging My Husband to a Blowjob with Andres Soldier's Monster Cock

Jizzberry 4 years ago

You nasty girl, licking cum off the floor!

You nasty girl, licking cum off the floor!

Fapcat 1 year ago

The challenge of keeping this sheath on my cock

The challenge of keeping this sheath on my cock

XVideos 4 months ago

INTENSIFY DICKLOOP Y - N

INTENSIFY DICKLOOP Y - N

Clips4sale 4 months ago

JXHXN - ADULT VERSION OF TIKTOK COMPILATION

JXHXN - ADULT VERSION OF TIKTOK COMPILATION

Fapcat 2 years ago

MICHELLE 24 Cm VS ADRIANA 20 Cm - (TGIRLS CHALLENGE)

MICHELLE 24 Cm VS ADRIANA 20 Cm - (TGIRLS CHALLENGE)

BeMyHole 2 years ago

Latina Masseuse Gives Sensual Massage Before Taking Huge Cock

Latina Masseuse Gives Sensual Massage Before Taking Huge Cock

ALOTPorn 7 months ago

SPH /CEI Hooter Taunt

SPH /CEI Hooter Taunt

TrannyGem 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!

Katestube 2 years ago

EDGE PLAY// Trangirls Massive Cock Gets Edged by GF until HUGE Shaking Orgasm!!

EDGE PLAY// Trangirls Massive Cock Gets Edged by GF until HUGE Shaking Orgasm!!

TatBabes 1 year ago

SNAPCHAT CUCKOLD COMPILATION (snapchat Sex, Snapchat Porn) - JXHXN on SPOTIFY

SNAPCHAT CUCKOLD COMPILATION (snapchat Sex, Snapchat Porn) - JXHXN on SPOTIFY

Fapcat 2 years ago

big cock transsexual gives deep anal to big tits milf

61% HD 0:30 / 33:21

big cock transsexual gives deep anal to big tits milf

AnalVids 1 year ago

Brunette Shemale Masturbating Her Prick

Brunette Shemale Masturbating Her Prick

Sheshaft 1 month ago

Transsexual anal challenge in Brazil - Episode #16

Transsexual anal challenge in Brazil - Episode #16

xHamster 2 years ago

Restrained Orgasm Challenge

HD 0:11 / 27:40

Restrained Orgasm Challenge

Clips4sale 3 years ago

No Nut November JOI Part 3

No Nut November JOI Part 3

TatBabes 1 year ago

The Janitor's Naughty Break

The Janitor's Naughty Break

M1lfs 1 month ago

Teen gets fucked by stepmom and her teacher

Teen gets fucked by stepmom and her teacher

Fapcat 11 months ago

Fist - only CUM challenge

Fist - only CUM challenge

XVideos 6 months ago

Boss Roberta Cortes demands sex from job applicant Hex - FULL (720p English)

66% HD 0:38 / 30:37

Boss Roberta Cortes demands sex from job applicant Hex - FULL (720p English)

Clips4sale 1 year 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

SpankBang 1 year ago

TGilrs CHALLENGE “FIGHT 22”, on ring Vallesca S. Vs Luna M. & Marica C.

Premium HD 41:23

TGilrs CHALLENGE “FIGHT 22”, on ring Vallesca S. Vs Luna M. & Marica C.

Sheer 3 years ago

Alpha & Beta Cum load Comparison - Fag Challenge - Slave Training

Alpha & Beta Cum load Comparison - Fag Challenge - Slave Training

xHamster 1 year ago

Try no to cum Challenge ! Futanari Edition (Hentai Fap Challenge)

Try no to cum Challenge ! Futanari Edition (Hentai Fap Challenge)

XVideos 1 year ago

Kendra James and Abigail Mac:Catwoman and Batwoman fall for the Futa stone! 720

61% HD 0:11 / 39:41

Kendra James and Abigail Mac:Catwoman and Batwoman fall for the Futa stone! 720

Clips4sale 3 years ago

DPing my ass and pussy with two dildos

DPing my ass and pussy with two dildos

Clips4sale 7 months ago

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - CLIP 3 OF 5 - WMV

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - CLIP 3 OF 5 - WMV

Clips4sale 1 year ago

Il contratto di Sissy - The Sissy's slut contract #2 (PART 2) (MOBILE VERSION MP4)

57% HD 0:11 / 17:53

Il contratto di Sissy - The Sissy's slut contract #2 (PART 2) (MOBILE VERSION MP4)

Clips4sale 1 year ago

3 HOUR TRY NOT TO CUM EDGING CHALLENGE FULL MOVIE

3 HOUR TRY NOT TO CUM EDGING CHALLENGE FULL MOVIE

YouPorn Unknown

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 1 month ago

Mrs Nara and 4 TS uses a guy and a girl as fuck holes - Complete (1080 EN-sub)

48% 4K 0:29 / 42:03

Mrs Nara and 4 TS uses a guy and a girl as fuck holes - Complete (1080 EN-sub)

Clips4sale 2 years ago

Olivia Jay offers up her pussy as a challenge to Jade Venus and Little Puck

Olivia Jay offers up her pussy as a challenge to Jade Venus and Little Puck

Eporner 2 months ago

Challenge Accepted.. Walking Outside Naked with Breasts

Challenge Accepted.. Walking Outside Naked with Breasts

xHamster 2 years ago

4K - Lusty Shower Vol 23 - Tokyo Bathroom Challenge EP1

4K 0:11 / 33:28

4K - Lusty Shower Vol 23 - Tokyo Bathroom Challenge EP1

Clips4sale 1 month ago

”Beautiful Raven-Haired Beauties Compete in a Steamy Widow's Showdown”

”Beautiful Raven-Haired Beauties Compete in a Steamy Widow's Showdown”

LesbianBliss 3 weeks ago

Aylla Gattina Vs Sabrina Fernandez (ts Challenge New

Aylla Gattina Vs Sabrina Fernandez (ts Challenge New

getTranny 2 years ago

Boss Roberta Cortes demands sex from job applicant Hex - FULL (1080p English)

51% HD 0:38 / 30:37

Boss Roberta Cortes demands sex from job applicant Hex - FULL (1080p English)

Clips4sale 1 year ago

Jess Mike Miller Tik Tok Flip The Switch Challenge Fuck Brunette Over Sink

Jess Mike Miller Tik Tok Flip The Switch Challenge Fuck Brunette Over Sink

Eporner 5 years ago

7 Ladyboys Cum Contest

48% 1:01 / 1:03:25

7 Ladyboys Cum Contest

FapHouse 2 years ago

Try not to nut tv edition pt 2

Try not to nut tv edition pt 2

XXXShemalePorn 5 years ago

TS Jessy Dubai moans with every hard thrust her BBC dom gives

TS Jessy Dubai moans with every hard thrust her BBC dom gives

Sheshaft 11 months ago

Jerk off Challenge - 3d Futa girls phone edition Metronome

Jerk off Challenge - 3d Futa girls phone edition Metronome

XVideos 2 years ago

Brazilian Bombshell Luna Alvier loves BBC

Premium HD 34:09

Brazilian Bombshell Luna Alvier loves BBC

Sheer 1 year ago

Your Cock and Balls Are Mine!! Dominant CBT Jo by Trannyi! German Deutsch

HD 1:01 / 12:19

Your Cock and Balls Are Mine!! Dominant CBT Jo by Trannyi! German Deutsch

FapHouse 1 month ago

Make Him Nut In 5 Minutes or Less Challenge Take 2

Make Him Nut In 5 Minutes or Less Challenge Take 2

XVideos 7 years ago

BOOT_COCKCORE: Gay System Override

BOOT_COCKCORE: Gay System Override

Clips4sale 4 months ago

Cock & Sole The Filthy Choice

50% 0:35 / 10:43

Cock & Sole The Filthy Choice

Clips4sale 6 months ago

CALAVERRECTION: I’m Hard. He’s Hard. You’re Just Begging.

CALAVERRECTION: I’m Hard. He’s Hard. You’re Just Begging.

Clips4sale 3 months ago

Vanessa vs JC: Arm Wrestling wmv

Vanessa vs JC: Arm Wrestling wmv

Clips4sale 9 months ago

10.4 inch dildo stretches my fat ass

10.4 inch dildo stretches my fat ass

xHamster 2 years ago

Goth Study Buddy's Self Sucking Contest (CEI)

67% 0:30 / 33:30

Goth Study Buddy's Self Sucking Contest (CEI)

Clips4sale 1 year ago

Hot Man Workout at Gym

Hot Man Workout at Gym

FapHouse 2 years ago

Sexy T-Girl Izzy Wilde Challenges Her GF Cami Strella To Sex Battle To Settle Argument!

Sexy T-Girl Izzy Wilde Challenges Her GF Cami Strella To Sex Battle To Settle Argument!

BeMyHole 9 months ago

Gemma Israel - Tgilrs Challenge (round 26) - Marcelle 23 Cm Vs

Gemma Israel - Tgilrs Challenge (round 26) - Marcelle 23 Cm Vs

AbTranny 3 years ago

Bbcgeorge with his biggest fan Anastasia-coxx, challenge accepted. Getting ready to make a lot of videos..

Bbcgeorge with his biggest fan Anastasia-coxx, challenge accepted. Getting ready to make a lot of videos..

XVideos 5 years ago

5 Minute Challenge

46% 4K 0:08 / 6:52

5 Minute Challenge

Clips4sale 4 years ago

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

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

Clips4sale 3 months ago

Danika Deep vs KaneVision Competitive Wrestling

Danika Deep vs KaneVision Competitive Wrestling

Clips4sale 3 years ago

Nara, Hex and Spicy Candy tag team to break a crossdresser brat's spirity (720 EN-sub)

HD 0:30 / 23:59

Nara, Hex and Spicy Candy tag team to break a crossdresser brat's spirity (720 EN-sub)

Clips4sale 2 years ago

”Oliver can't resist temptresses Avery Christy & Vanna Bardot's challenge”

”Oliver can't resist temptresses Avery Christy & Vanna Bardot's challenge”

TransHero 3 months ago

Set of Pool Balls Inserted & Pulled Out by Valentinarosa89 Stretch

54% HD 0:39 / 9:03

Set of Pool Balls Inserted & Pulled Out by Valentinarosa89 Stretch

FapHouse 1 year ago

She-Male VS She-Male!!! - (Challenge #02)

She-Male VS She-Male!!! - (Challenge #02)

xHamster 4 years ago

Groobygirls Bareback Only for Belle Adams

HD 1:01 / 22:18

Groobygirls Bareback Only for Belle Adams

FapHouse 3 months 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

BBC TS Sniffies Sneaky Link

55% 0:30 / 22:48

BBC TS Sniffies Sneaky Link

Clips4sale 8 months ago

HotHouse: Hairy ebony crossdresser desires rough slamming hard

HotHouse: Hairy ebony crossdresser desires rough slamming hard

IGaySEXTV 4 years ago

Jerk Off challenge by Asian Transgirl

Jerk Off challenge by Asian Transgirl

xHamster 7 months ago

Here we goes the CHALLENGE FIGHT 223, on ring Keylla VS Linda

Here we goes the CHALLENGE FIGHT 223, on ring Keylla VS Linda

xHamster 2 years ago

GlitterGiiiirl´s NikePro Dildo Riding with CalvinKlein Crop Top

GlitterGiiiirl´s NikePro Dildo Riding with CalvinKlein Crop Top

Clips4sale 6 months ago

”TS Stars : 5 Hung Latinas vs 1 Guy Raw Orgy 4k”

”TS Stars : 5 Hung Latinas vs 1 Guy Raw Orgy 4k”

TransHero 6 years ago

Wedgie wrestling-mobile friendly

Wedgie wrestling-mobile friendly

Clips4sale 1 year ago

”TBabe university babe Janelle Fennec is the new chick in the town”

”TBabe university babe Janelle Fennec is the new chick in the town”

LesbianBliss 3 weeks ago

Black Stepdaddy Ken Busts Open Candy Ass Sissy's White Ass to New Levels of Ecstacy and Agony with Thick 10-inch BBC

HD 1:01 / 17:26

Black Stepdaddy Ken Busts Open Candy Ass Sissy's White Ass to New Levels of Ecstacy and Agony with Thick 10-inch BBC

FapHouse 2 years ago

Femboy Gooner Teen Busts a Nut Cums Sissy Twink Cam Transgender Girl

Femboy Gooner Teen Busts a Nut Cums Sissy Twink Cam Transgender Girl

Pornzona 1 week ago

Ebony beauty Brooke Morgan solo

Ebony beauty Brooke Morgan solo

xHamster 2 months 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 3 months ago

Wedgie wrestling-4K

Premium 4K 8:48

Wedgie wrestling-4K

Clips4sale 1 year ago

Sucky Tekken Battle: Futanari

Sucky Tekken Battle: Futanari

FapHouse 11 months ago

Sexy Jade Trolling for Poling

HD 0:39 / 44:42

Sexy Jade Trolling for Poling

FapHouse 7 months ago

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

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

xHamster 3 years ago

Wrestling to Fuck

Wrestling to Fuck

FapHouse 5 years ago

camilla 20 cm vs jolie 25 cm trnsgender challenge 129 x

camilla 20 cm vs jolie 25 cm trnsgender challenge 129 x

Pornwhite 7 months ago

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - CLIP 1 OF 5 - MP4

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - CLIP 1 OF 5 - MP4

Clips4sale 1 year ago

Big tit muscle futa cock to cock fuck fight: Monica vs Rogue 720p

65% HD 0:30 / 6:15

Big tit muscle futa cock to cock fuck fight: Monica vs Rogue 720p

Clips4sale 1 year ago

Challenging My Neighbors - Cum Rain, Piss

HD 1:01 / 11:24

Challenging My Neighbors - Cum Rain, Piss

FapHouse 1 year ago

Edging Challenge 1028 Day One 3 Days UnCummed Clip 2

Edging Challenge 1028 Day One 3 Days UnCummed Clip 2

xHamster 1 month ago

YOU'RE GETTING BOINKED BY A TRANS DAMSEL Jerk Off Instructions

YOU'RE GETTING BOINKED BY A TRANS DAMSEL Jerk Off Instructions

Transvids.tv 8 months ago

My Hottest Soapiest Shower POV Fat Cock Cumming

My Hottest Soapiest Shower POV Fat Cock Cumming

xHamster 1 year ago

Wrestling to Fuck

68% 1:01 / 20:43

Wrestling to Fuck

FapHouse 5 years 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 1 year ago

Mel Fire and TS Frantiesca guide you when and how to have the best orgasm ever (engl-port)

63% HD 0:30 / 8:29

Mel Fire and TS Frantiesca guide you when and how to have the best orgasm ever (engl-port)

Clips4sale 1 year ago

Sissy cockslut non stop edging for being a bad lady

Sissy cockslut non stop edging for being a bad lady

TrannyGem 1 year ago

”GROOBYVR - Miss Canadian Pie”

”GROOBYVR - Miss Canadian Pie”

TransHero 2 months ago

Femaledominance Nubile Ruthlessly edges me with a Draining Machine(Utter Version on OnlyFans @princesscrossed)

Femaledominance Nubile Ruthlessly edges me with a Draining Machine(Utter Version on OnlyFans @princesscrossed)

TransTube.tv 1 year ago

Interactive: Chastity Challenge: Questions for a Slave - Maitresse Julia

73% HD 1:01 / 18:03

Interactive: Chastity Challenge: Questions for a Slave - Maitresse Julia

FapHouse 1 year ago

7 Ladyboys Cum Contest

7 Ladyboys Cum Contest

FapHouse 2 years ago

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

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

IFuckedYourGF 3 weeks ago

SISSY SHOOTS A LOAD IN INNOCENCE AFTER five DAYS OF VIRGINITY JIZM IN MAN ROD BOX V-Card Jism Compilation

SISSY SHOOTS A LOAD IN INNOCENCE AFTER five DAYS OF VIRGINITY JIZM IN MAN ROD BOX V-Card Jism Compilation

TrannyGem 4 years ago

TGilrs CHALLENGE (round 30) - Keyla Marquesi 24 cm VSTauana

TGilrs CHALLENGE (round 30) - Keyla Marquesi 24 cm VSTauana

xHamster 3 years ago

3D Porn Carton: Petite Busty Princess Takes the Shemale Monster's Fuck Challenge

3D Porn Carton: Petite Busty Princess Takes the Shemale Monster's Fuck Challenge

Fapality 2 years ago

5 6 7 8 9

3,731 results found

Related categories

Milking Table Edging Braces Encouragement Nipple Piercing Goon Gagging Tease Premature Ejaculation Shaking Orgasm CFNM Dangling Begging Punk Instructions Edging Compilation Laughing Doggystyle Compilation Freak Piercing

Narrow your search

jerk off challenge try not to cum challenge edging challenge cum challenge dont cum challenge anal challenge joi challenge cock hero challenge dildo challenge stroke challenge orgasm challenge edge challenge deepthroat challenge jerk challenge stranger challenge do not cum challenge escape challenge blowjob challenge mea melone 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.