Challenge Videos - Trans (4,113)

TGilrs CHALLENGE (round 26) - Marcelle 23 cm VS Gemma Israel

TGilrs CHALLENGE (round 26) - Marcelle 23 cm VS Gemma Israel

xHamster 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 3 years ago

UP CLOSE - How Nymphs Ejaculation With Stacked Trans Brittney Kade! SOLO TRANS GETTING OFF! TOTAL VIGNETTE

UP CLOSE - How Nymphs Ejaculation With Stacked Trans Brittney Kade! SOLO TRANS GETTING OFF! TOTAL VIGNETTE

TransTube.tv 1 year ago

$Сhallenge - can you not touch the dick.\RUS$ 76% HD 3:48

Сhallenge - can you not touch the dick.\RUS

aShemaleTube 4 years ago

Renata VS Bella (Tgirls Extreme Challenge)

Renata VS Bella (Tgirls Extreme Challenge)

xHamster 3 years ago

Twister Gone Wild: All-Gender Orgy Party - Cliff Media

Twister Gone Wild: All-Gender Orgy Party - Cliff Media

xHamster 1 year ago

This Will Blow Your Mind: Vaniity Is Back

58% HD 1:01 / 35:43

This Will Blow Your Mind: Vaniity Is Back

FapHouse 2 months ago

Wanking challenger

Wanking challenger

Tranny.one 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

Transexual anal challenge - Episode #08

Transexual anal challenge - Episode #08

xHamster 2 years ago

Hot Korra Del Rio Challenges Her Hot Asshole with a Bat

Hot Korra Del Rio Challenges Her Hot Asshole with a Bat

xHamster 3 months ago

Challenging My Neighbors- Cum Rain Piss

Challenging My Neighbors- Cum Rain Piss

getTranny 3 years ago

Fishnet Femboy bounces his Fat Ass on Big Dildos

Fishnet Femboy bounces his Fat Ass on Big Dildos

xHamster 9 months ago

Here we goes the CHALLENGE FIGHT, on ring Linda VS Jennifer

Here we goes the CHALLENGE FIGHT, on ring Linda VS Jennifer

xHamster 2 years ago

Try to WATCH Full VIDEO WITHOUT LOOKING at any DICK Challenge SISSY Test

Try to WATCH Full VIDEO WITHOUT LOOKING at any DICK Challenge SISSY Test

Tranny.one 4 years ago

Asian TGirl Cum Challenge JOI - Strokes Her Trans Cock in Purple Lingerie

Asian TGirl Cum Challenge JOI - Strokes Her Trans Cock in Purple Lingerie

Eporner 3 weeks ago

Hankeys Toys Tryouts - L Big Daddy

Hankeys Toys Tryouts - L Big Daddy

xHamster 1 year ago

TRANSGIRL JIZM COMPILATION STAMINA COMPETE PART two - Can you make it to the end ?

TRANSGIRL JIZM COMPILATION STAMINA COMPETE PART two - Can you make it to the end ?

TrannyGem 2 years ago

Jennyfer VS Rafaella (Tgirls Extreme Challenge)

Jennyfer VS Rafaella (Tgirls Extreme Challenge)

xHamster 3 years ago

Blonde bombshell with a pierced pussy takes on two dudes for some cash

Blonde bombshell with a pierced pussy takes on two dudes for some cash

Some.Porn 2 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

cock confusion challenge

cock confusion challenge

Eporner 11 months ago

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

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

xHamster 3 years ago

Latina Tgirl's Monster Cock Jerks Off in Raw POV Cum Challenge

Latina Tgirl's Monster Cock Jerks Off in Raw POV Cum Challenge

Pornwhite 3 weeks ago

”Try Not to Cum Ass Pumping Compilation: Hard Challenge”

”Try Not to Cum Ass Pumping Compilation: Hard Challenge”

TransHero 6 months ago

TGilrs CHALLENGE (round 03) - Anne Kelly 23 cm VS Mirella

TGilrs CHALLENGE (round 03) - Anne Kelly 23 cm VS Mirella

xHamster 3 years ago

Another Straight Boy in Conversion Challenge

Another Straight Boy in Conversion Challenge

Tranny.one 4 years ago

Mariaangel and Antotss Cumshot challenge 🍆💦

Mariaangel and Antotss Cumshot challenge 🍆💦

aShemaleTube 1 month ago

Krystallcox with Sounding Rods Urethral Play

Krystallcox with Sounding Rods Urethral Play

xHamster 1 year ago

Great girl-girl show for her master! Jerk off challenge for two hot tranny girlies!

Great girl-girl show for her master! Jerk off challenge for two hot tranny girlies!

xHamster 1 year ago

Straight Boy Test (T-girls, Shlong)

Straight Boy Test (T-girls, Shlong)

Dafreeporn 5 years ago

Cum Challenge Compilation Part3

Cum Challenge Compilation Part3

Fapcat 1 year ago

FapFantastika 9

FapFantastika 9

Eporner 6 months ago

Female Domination Teenager Mercilessly edges me with a Jerking Machine(Utter Version on OnlyFans @princesscrossed)

Female Domination Teenager Mercilessly edges me with a Jerking Machine(Utter Version on OnlyFans @princesscrossed)

TrannyGem 2 years ago

Cumshots TGilrs Challenge

Cumshots TGilrs Challenge

BeMyHole 3 years ago

Sissy Slut Challenge - Pimped out

Sissy Slut Challenge - Pimped out

Eporner 5 months ago

Submit to Daddy's Edging Challenge: POV JOI Cum Command Session! - Jaq Quicksilver - strapon, game, ftm, praise - 4k mp4

4K 0:29 / 12:14

Submit to Daddy's Edging Challenge: POV JOI Cum Command Session! - Jaq Quicksilver - strapon, game, ftm, praise - 4k mp4

Clips4sale 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

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

Rafaella VS Isabel (Tgirls Extreme Challenge)

Rafaella VS Isabel (Tgirls Extreme Challenge)

BeMyHole 3 years ago

Lorena VS Priscilla (Tgirls Extreme Challenge)

Lorena VS Priscilla (Tgirls Extreme Challenge)

xHamster 3 years ago

Multi Orgasm Challenge

Multi Orgasm Challenge

Eporner 4 years ago

Here we goes the CHALLENGE FIGHT 193, on ring Anna VS Roberta

Here we goes the CHALLENGE FIGHT 193, on ring Anna VS Roberta

xHamster 3 years ago

The Dildo Riding Challenge

The Dildo Riding Challenge

Eporner 1 month ago

Edging challenge

Edging challenge

Eporner 4 years ago

Str8 Male Test (Transsexuals, Jock)

Str8 Male Test (Transsexuals, Jock)

FreePorn8 5 years ago

Natalia VS Mohana (Tgirls Extreme Challenge)

Natalia VS Mohana (Tgirls Extreme Challenge)

BeMyHole 3 years ago

Sissy Joyce Challenge

Sissy Joyce Challenge

xHamster 3 months ago

This Will Blow Your Mind: Vaniity Is Back

This Will Blow Your Mind: Vaniity Is Back

xHamster 2 months ago

Watch these kinky babes in action as they compete in Innocence contest Diaries

Watch these kinky babes in action as they compete in Innocence contest Diaries

TrannyMovs 2 months ago

Try not to cum. Bitch twerking, screwing and being a doxy.

Try not to cum. Bitch twerking, screwing and being a doxy.

ShemaleSin 1 year ago

Transsexual Here We Goes The CHALLENGE FIGHT, On Ring Renata VS Bianca

Transsexual Here We Goes The CHALLENGE FIGHT, On Ring Renata VS Bianca

BeMyHole 2 years ago

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

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

Bokep.PORN 4 months ago

Melissa Masters - Don't Deny You Love Cock JOI Challenge

Melissa Masters - Don't Deny You Love Cock JOI Challenge

IcePorn 6 months ago

TGilrs CHALLENGE (round 27) - Priscilla Beckam 20 cm VS

TGilrs CHALLENGE (round 27) - Priscilla Beckam 20 cm VS

xHamster 3 years ago

TGilrs CHALLENGE (round 04) - Daniela Colucci 20 cm VS Luana

TGilrs CHALLENGE (round 04) - Daniela Colucci 20 cm VS Luana

xHamster 3 years ago

Asian TGirl Cum Challenge JOI - Strokes Her Trans Cock in Purple Lingerie

Asian TGirl Cum Challenge JOI - Strokes Her Trans Cock in Purple Lingerie

xHamster 3 weeks ago

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

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

xHamster 3 years ago

Cock Confusion Challenge II

Cock Confusion Challenge II

Eporner 11 months ago

Edging Game With Trans Hotty Leads To Massive CumShots! (Greater amount On OF)

Edging Game With Trans Hotty Leads To Massive CumShots! (Greater amount On OF)

ShemaleSin 1 month ago

EXTREME EDGING CHALLENGE 1 HOUR EDITION

EXTREME EDGING CHALLENGE 1 HOUR EDITION

Pornzona 3 months ago

Multi Orgasm Challenge

Multi Orgasm Challenge

BeMyHole 4 years ago

Kessie VS Victoria (Tgirls Extreme Challenge)

Kessie VS Victoria (Tgirls Extreme Challenge)

xHamster 3 years ago

Here we goes the CHALLENGE FIGHT 213, on ring Melissa VS Helly

Here we goes the CHALLENGE FIGHT 213, on ring Melissa VS Helly

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 1 year ago

Hands Off Challenge - Day 27

Hands Off Challenge - Day 27

AbTranny 3 weeks ago

FapFantastika 11

FapFantastika 11

Eporner 6 months ago

Not Quite Straight Vol. 2 PMV Challenge

Not Quite Straight Vol. 2 PMV Challenge

Eporner 2 years ago

ABT250116 20cm Dildo Challenge

ABT250116 20cm Dildo Challenge

xHamster 1 month ago

Perfect Emotional Shemale Cumpilation (try not to cum challenge)

Perfect Emotional Shemale Cumpilation (try not to cum challenge)

aShemaleTube 4 months 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

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

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

xHamster 3 years ago

Trap Hetero Synesthesia

Trap Hetero Synesthesia

BigTitsLust 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

Rafaela VS Sabrina (Tgirls Extreme Challenge)

Rafaela VS Sabrina (Tgirls Extreme Challenge)

xHamster 3 years ago

Sissy Challenge

54% HD 0:10 / 5:14

Sissy Challenge

LoyalFans 3 years ago

4 CUMS RUINED !!!

4 CUMS RUINED !!!

xHamster 3 years ago

Riding ONLY (Anal Masturbation Instructional)

57% HD 0:10 / 19:18

Riding ONLY (Anal Masturbation Instructional)

LoyalFans 2 months ago

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - CLIP 2 OF 5 - MP4

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - CLIP 2 OF 5 - MP4

Clips4sale 1 year ago

Big Load TGilrs Challenge

Big Load TGilrs Challenge

BeMyHole 3 years ago

JOI challenge for gooners and addicts

JOI challenge for gooners and addicts

Eporner 7 months 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

Geovane VS Renata (Tgirls Extreme Challenge)

Geovane VS Renata (Tgirls Extreme Challenge)

xHamster 3 years ago

Curious guy tries to handle big transsexual dick

Curious guy tries to handle big transsexual dick

xHamster 10 months ago

Back to School BangFest

Back to School BangFest

XXXShake 3 years ago

Teen Birthday

Eporner 2 years ago

Dont Cum, Sissy! - Sissy Futa Captions Challenge - Futamaxxing

Dont Cum, Sissy! - Sissy Futa Captions Challenge - Futamaxxing

Eporner 1 week ago

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

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

BeMyHole 3 years ago

[l A] Masters Quest Horny Femboy Bitch Oral Pussy Swallow Cum Development Electroshock Urethral Snake Rod Asshole Torture Challenge

[l A] Masters Quest Horny Femboy Bitch Oral Pussy Swallow Cum Development Electroshock Urethral Snake Rod Asshole Torture Challenge

AbTranny 1 month ago

Crossdress Iskra and here panties

Crossdress Iskra and here panties

xHamster 1 year ago

Tgilrs Challenge (round 50 22 Cm Vs Kiara 20 - Luna Marks

Tgilrs Challenge (round 50 22 Cm Vs Kiara 20 - Luna Marks

PornUse 5 months ago

Cocky gym-bro alpha dominates and humiliates you - Jaq Quicksilver - FtM Trans jock punishes you for being closeted with rough fucking - ft slapping, spitting, verbal humiliation, muscle worship, blowjob, pov fucking - 4k mp4

4K 0:30 / 12:29

Cocky gym-bro alpha dominates and humiliates you - Jaq Quicksilver - FtM Trans jock punishes you for being closeted with rough fucking - ft slapping, spitting, verbal humiliation, muscle worship, blowjob, pov fucking - 4k mp4

Clips4sale 1 year 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

EDGE HAVE FUN // Kinky T-woman Gets Mercilessly Edged by Alyce Pettit

EDGE HAVE FUN // Kinky T-woman Gets Mercilessly Edged by Alyce Pettit

TransTube.tv 1 year ago

sexy shemales with amazing big ass gets ai treatment with phat big dicks.

51% HD 0:19 / 6:23

sexy shemales with amazing big ass gets ai treatment with phat big dicks.

PornBox 2 years ago

On Valentine's Day, moved by a boyfriend and worried himself

On Valentine's Day, moved by a boyfriend and worried himself

xHamster 1 week ago

Try out of machine fuck thick 15 inch BBC King Cock dildo

Try out of machine fuck thick 15 inch BBC King Cock dildo

xHamster 1 year ago

Here we goes the CHALLENGE FIGHT, on ring Ariadny VS Sabrina

Here we goes the CHALLENGE FIGHT, on ring Ariadny VS Sabrina

xHamster 3 years ago

Hung Shemale Gabrielly Ferraz Fucking Another Chick with a Dick in Hardcore TS Action

Hung Shemale Gabrielly Ferraz Fucking Another Chick with a Dick in Hardcore TS Action

XXXShake 3 months ago

Bruna VS Walkiria (Tgirls Extreme Challenge)

Bruna VS Walkiria (Tgirls Extreme Challenge)

xHamster 3 years ago

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

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

xHamster 3 years ago

Femboy MILF in the Ultimate Gooner Boy Challenge

Femboy MILF in the Ultimate Gooner Boy Challenge

aShemaleTube 2 weeks ago

Here we goes the CHALLENGE FIGHT 222, on ring Mary VS Letizia

Here we goes the CHALLENGE FIGHT 222, on ring Mary VS Letizia

xHamster 3 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 1 year ago

Turbo Cum Draining in 60 Seconds Turbo JOI Cum for your Brain ! Drain yourself in 1 Minute - 60 Seconds JOI Cum Defiance Turbo Prejac Unload

Turbo Cum Draining in 60 Seconds Turbo JOI Cum for your Brain ! Drain yourself in 1 Minute - 60 Seconds JOI Cum Defiance Turbo Prejac Unload

ShemaleSin 1 month ago

Asian TGirl Cum Challenge JOI - Strokes Her Trans Cock in Purple Lingerie

Asian TGirl Cum Challenge JOI - Strokes Her Trans Cock in Purple Lingerie

aShemaleTube 3 weeks 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 1 year ago

Shemale Porn Video TGilrs CHALLENGE - Valesca Sargentely 22 Cm

Shemale Porn Video TGilrs CHALLENGE - Valesca Sargentely 22 Cm

Tranny.one 1 year ago

Challenging my neighbors- Cum rain, pee

Challenging my neighbors- Cum rain, pee

TransTube.tv 1 year ago

Trans mother i'd like to fuck redhead cums on a sex toy whilst drenched in oil and lube

Trans mother i'd like to fuck redhead cums on a sex toy whilst drenched in oil and lube

SortPorn 3 weeks ago

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

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

xHamster 3 years ago

Gloria VS Melissa (Tgirls Extreme Challenge)

Gloria VS Melissa (Tgirls Extreme Challenge)

xHamster 3 years ago

Here we goes the CHALLENGE FIGHT 220, on ring Linda VS Jennifer

Here we goes the CHALLENGE FIGHT 220, on ring Linda VS Jennifer

xHamster 3 years ago

femboy long edging session in thigh highs & sleaves - 29 minute slow stroke cum on thigh

femboy long edging session in thigh highs & sleaves - 29 minute slow stroke cum on thigh

xHamster 1 week ago

TGilrs CHALLENGE (round 50) - Luna Marks 22 cm VS Kiara 20

TGilrs CHALLENGE (round 50) - Luna Marks 22 cm VS Kiara 20

xHamster 3 years ago

Fist - only CUM challenge

Fist - only CUM challenge

XVideos 9 months ago

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

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

Tranny.one 1 year ago

Eva Turned a Top Guy Into a Bottom

54% HD 1:01 / 16:41

Eva Turned a Top Guy Into a Bottom

FapHouse 3 months ago

Ts babe reach orgasm by jerking her stiff cock

Ts babe reach orgasm by jerking her stiff cock

VikiPorn 7 months ago

TGilrs CHALLENGE (round 37) - Raphaella Ferrari 22 cm VS

TGilrs CHALLENGE (round 37) - Raphaella Ferrari 22 cm VS

xHamster 3 years ago

1 2 3 4 5

4,113 results found

Related categories

Edging WTF Gagging Milking Table Nipple Piercing Kinky Braces Cockring Bound Tease Spit Roast Throat Facial Swallowing Barebacking Throat Fuck Fetish Freckled Face Sitting Jerking Off

Narrow your search

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

Categories Pornstars

Categories Pornstars

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.