Challenge Videos - Trans (369)

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

Beta Loser Caught by Neighbor - A sissy training scene featuring: caught, humiliatrix, beta boy pov, pussy free pledge, censored porn, and JOI games - 720 MP4

HD 0:19 / 19:48

Beta Loser Caught by Neighbor - A sissy training scene featuring: caught, humiliatrix, beta boy pov, pussy free pledge, censored porn, and JOI games - 720 MP4

Clips4sale 2 years ago

Sucking Off Three Futa Dick Girls - A Futanari Scene featuring Big Dicks, Femdom POV, and POV Face Fucking - 720 WMV

HD 0:29 / 11:19

Sucking Off Three Futa Dick Girls - A Futanari Scene featuring Big Dicks, Femdom POV, and POV Face Fucking - 720 WMV

Clips4sale 3 years ago

GAY TEST. exe Final Stroke Protocol

GAY TEST. exe Final Stroke Protocol

Clips4sale 8 months 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

Girlfriend isn't Just Stronger Than You- Her Dick is Bigger Too! (ID #1832 HD 1080)

57% HD 0:11 / 10:06

Girlfriend isn't Just Stronger Than You- Her Dick is Bigger Too! (ID #1832 HD 1080)

Clips4sale 4 years ago

Sucking Off Three Futa Dick Girls

HD 0:10 / 11:19

Sucking Off Three Futa Dick Girls

LoyalFans 3 years ago

Sissy Shopping Challenge

Sissy Shopping Challenge

Clips4sale 2 years ago

Chastity Sissy Marissa Nicole Heavily Gagged and Left for the Maid

47% 0:33 / 22:35

Chastity Sissy Marissa Nicole Heavily Gagged and Left for the Maid

Clips4sale 1 year ago

The Cum Cookie Challenge

61% 0:28 / 13:59

The Cum Cookie Challenge

Clips4sale 3 years ago

Rope Tied Oil Catfight and Trib Fight

61% 0:30 / 10:08

Rope Tied Oil Catfight and Trib Fight

Clips4sale 1 year ago

BBC TS Sniffies Sneaky Link

55% 0:30 / 22:48

BBC TS Sniffies Sneaky Link

Clips4sale 1 year ago

Gamer Girl [Part 1]

4K 0:11 / 15:44

Gamer Girl [Part 1]

Clips4sale 4 years ago

New Year PigTox!

New Year PigTox!

Clips4sale 6 months ago

Beating up the tiny asian sissy

66% 0:26 / 14:56

Beating up the tiny asian sissy

Clips4sale 3 years ago

GlitterGiiiirl´s NikePro Dildo Riding with CalvinKlein Crop Top

GlitterGiiiirl´s NikePro Dildo Riding with CalvinKlein Crop Top

Clips4sale 11 months ago

INTENSIFY DICKLOOP Y - N

INTENSIFY DICKLOOP Y - N

Clips4sale 8 months ago

The Trap Session - CLASSICS SALE

65% 0:11 / 11:09

The Trap Session - CLASSICS SALE

Clips4sale 3 years ago

Feminized by the Chef: A Locktober Tale

45% 4K 0:30 / 35:05

Feminized by the Chef: A Locktober Tale

Clips4sale 1 year ago

Mel Fire and TS Frantiesca love to watch you cum when they decide so (engl-port)

Mel Fire and TS Frantiesca love to watch you cum when they decide so (engl-port)

Clips4sale 1 year ago

CUM injection and BIG TOYS for the perfect PEGGING SISSYGASM!

68% HD 0:30 / 17:28

CUM injection and BIG TOYS for the perfect PEGGING SISSYGASM!

Clips4sale 1 year ago

TS Sex Goddess Takes a Man to His Absolute Limit

HD 0:29 / 35:25

TS Sex Goddess Takes a Man to His Absolute Limit

Clips4sale 4 years ago

Mistress Marceau Bondage Model Training Manual Part 1

HD 0:05 / 13:24

Mistress Marceau Bondage Model Training Manual Part 1

Clips4sale 2 years ago

Wedgie wrestling

Wedgie wrestling

Clips4sale 2 years ago

Step-Sister Physically Dominates You and Owns Your Ass (ID # 1839 HD 1080rez)

Step-Sister Physically Dominates You and Owns Your Ass (ID # 1839 HD 1080rez)

Clips4sale 1 year 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

Locktober Special - Day 31: Halloween

Locktober Special - Day 31: Halloween

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

New Year, Same Stronger-than-you-gf with a bigger cock! (ID # 1827 HD 1080rez)

New Year, Same Stronger-than-you-gf with a bigger cock! (ID # 1827 HD 1080rez)

Clips4sale 1 year ago

How to Suck a 10" inch BBC Cock Blowjob Instructions POV

HD 0:10 / 15:55

How to Suck a 10" inch BBC Cock Blowjob Instructions POV

LoyalFans 9 months ago

Edge for My Ass in Yoga Pants

Edge for My Ass in Yoga Pants

Clips4sale 2 years ago

Futa Story: Insubordination - Ft Imilia Audley

4K 0:29 / 12:27

Futa Story: Insubordination - Ft Imilia Audley

Clips4sale 1 year ago

Cutest Sissy Task

Cutest Sissy Task

Clips4sale 3 years ago

Captured Infiltrator Part 2

Captured Infiltrator Part 2

Clips4sale 4 years ago

Dani M Love Gets Some Extra Training Before Her New Job at Hooters!

Dani M Love Gets Some Extra Training Before Her New Job at Hooters!

Clips4sale 3 years ago

Epic Hot Gay Kissing and Tongue Fetish 37 - CUSTOM VIDEO - JC Dickerson - Leo Blue - Manpuppy - MP4 720

HD 0:09 / 31:02

Epic Hot Gay Kissing and Tongue Fetish 37 - CUSTOM VIDEO - JC Dickerson - Leo Blue - Manpuppy - MP4 720

Clips4sale 3 years ago

Sucking Off Three Futa Dick Girls - A Futanari Scene featuring Big Dicks, Femdom POV, and POV Face Fucking - 1080 WMV

HD 0:29 / 11:19

Sucking Off Three Futa Dick Girls - A Futanari Scene featuring Big Dicks, Femdom POV, and POV Face Fucking - 1080 WMV

Clips4sale 3 years ago

One Chip Challenge

HD 0:10 / 11:10

One Chip Challenge

Clips4sale 4 years ago

Epic Gay Kissing and Mouth Fetish 37 - CUSTOM VIDEO - JC Dickerson - Leo Blue - Manpuppy - WMV 720

HD 0:09 / 31:02

Epic Gay Kissing and Mouth Fetish 37 - CUSTOM VIDEO - JC Dickerson - Leo Blue - Manpuppy - WMV 720

Clips4sale 3 years ago

Exposed Sissy Challenge

HD 0:10 / 11:03

Exposed Sissy Challenge

LoyalFans 3 years ago

Sissy Panties Challenge

Sissy Panties Challenge

LoyalFans 2 years ago

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

58% HD 0:11 / 35:01

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

Clips4sale 2 years ago

SISSY-SUCK-A-LONG - Level: Dark Shame! (JOI Game)

SISSY-SUCK-A-LONG - Level: Dark Shame! (JOI Game)

Clips4sale 1 year ago

Rope Tied Oil Catfight and Trib Fight full wmv

61% HD 0:30 / 31:50

Rope Tied Oil Catfight and Trib Fight full wmv

Clips4sale 1 year ago

Locked and Cucked for Valentine's Day

Locked and Cucked for Valentine's Day

LoyalFans 2 years ago

Your Step-Cousin is Stronger than you! (ID # 1900 HD 1080rez)

HD 0:11 / 10:42

Your Step-Cousin is Stronger than you! (ID # 1900 HD 1080rez)

Clips4sale 2 years ago

Beta Loser Caught by Neighbor - A sissy training scene featuring: caught, humiliatrix, beta boy pov, pussy free pledge, censored porn, and JOI games - 720 WMV

HD 0:19 / 19:48

Beta Loser Caught by Neighbor - A sissy training scene featuring: caught, humiliatrix, beta boy pov, pussy free pledge, censored porn, and JOI games - 720 WMV

Clips4sale 2 years ago

Day 56 Sissy Training Programme: Sissy Task 08

Day 56 Sissy Training Programme: Sissy Task 08

Clips4sale 1 year ago

48 Chicken Nuggets

48 Chicken Nuggets

Clips4sale 1 year ago

Hellish Aroma Trapdoor Part 2

Hellish Aroma Trapdoor Part 2

Clips4sale 11 months ago

12 steps to PigmasTox

12 steps to PigmasTox

Clips4sale 7 months ago

You're The Dirtiest BBC Faggot

You're The Dirtiest BBC Faggot

Clips4sale 1 year ago

Kendra James and Abigail Mac:Catwoman and Batwoman fall for the Futa stone! mp4 HD

61% HD 0:11 / 39:41

Kendra James and Abigail Mac:Catwoman and Batwoman fall for the Futa stone! mp4 HD

Clips4sale 3 years ago

Teacher Hex’s practical class of biology with TS student girl Sophie (1080p ENG-sub) Trans Woman - Trans Blowjob - Trans Fucking

66% HD 0:32 / 56:20

Teacher Hex’s practical class of biology with TS student girl Sophie (1080p ENG-sub) Trans Woman - Trans Blowjob - Trans Fucking

Clips4sale 1 year ago

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

63% 0:18 / 5:08

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

Clips4sale 1 year ago

Epic Hot Gay Kissing 37 - CUSTOM VIDEO - JC Dickerson - Leo Blue - Manpuppy - MP4 1080

HD 0:09 / 31:02

Epic Hot Gay Kissing 37 - CUSTOM VIDEO - JC Dickerson - Leo Blue - Manpuppy - MP4 1080

Clips4sale 4 years ago

Suck an Old Mans Dick: Sissy Ruination

HD 0:10 / 10:07

Suck an Old Mans Dick: Sissy Ruination

LoyalFans 3 years ago

Barbie Challenge

Barbie Challenge

LoyalFans 3 years ago

Transgender Burp Off

51% 0:10 / 9:49

Transgender Burp Off

Clips4sale 2 years ago

Gay porn addiction programming WMV

47% 0:11 / 6:07

Gay porn addiction programming WMV

Clips4sale 2 years ago

Slap and stroke JOI game A version - CBT

HD 0:10 / 10:49

Slap and stroke JOI game A version - CBT

LoyalFans 2 years ago

Sir's Obedient Pet

64% 0:10 / 16:29

Sir's Obedient Pet

Clips4sale 2 years ago

No Stroke Challenge Part Three, Intermediate Sissy Fuck

HD 0:10 / 10:09

No Stroke Challenge Part Three, Intermediate Sissy Fuck

LoyalFans 3 years ago

Is this the BEST Bondage model EVER?! This is Unbelievable Charlie and Mila left speechless

Is this the BEST Bondage model EVER?! This is Unbelievable Charlie and Mila left speechless

Clips4sale 2 years 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

Slave Nips submits to all my challenges

Slave Nips submits to all my challenges

LoyalFans 1 year ago

Step-Mom Catches you Snooping and Physically Dominates you to Get you in Line! (ID # 1832 HD 1080rez)

65% HD 0:30 / 8:44

Step-Mom Catches you Snooping and Physically Dominates you to Get you in Line! (ID # 1832 HD 1080rez)

Clips4sale 1 year ago

I Oil Up My Trans Cock and Masturbate

I Oil Up My Trans Cock and Masturbate

Clips4sale 1 year ago

KaneVision vs Felix Stone Competitive Wrestling

KaneVision vs Felix Stone Competitive Wrestling

Clips4sale 5 years ago

Public nudity while cycling!! Tranny girl rides not only the bike, also a dildo!

59% HD 0:29 / 11:14

Public nudity while cycling!! Tranny girl rides not only the bike, also a dildo!

Clips4sale 1 year ago

4K - Femcock vs Vibrator Round 3

57% 4K 0:22 / 17:14

4K - Femcock vs Vibrator Round 3

Clips4sale 1 year ago

Facessiting Trans Goddess Rose - FT Goddess Marcy

Facessiting Trans Goddess Rose - FT Goddess Marcy

LoyalFans 2 years ago

Mistress Baton Does The Thousand Fist Challenge HD for QT

Premium 4K 37:46

Mistress Baton Does The Thousand Fist Challenge HD for QT

Clips4sale 2 years ago

Josie Jo Brings Me Home For Her Boyfriend To Worship My Feet (HD1080 MP4)

Josie Jo Brings Me Home For Her Boyfriend To Worship My Feet (HD1080 MP4)

Clips4sale 2 years ago

ROSE’S 1st AFTERCARE BELLY WORSHIP

ROSE’S 1st AFTERCARE BELLY WORSHIP

Clips4sale 2 years ago

Barbie Challenge

Barbie Challenge

Clips4sale 3 years ago

The Fisting Party Part 3 - Vivienne l'Amour and Sadie Katinka go Wide and Deep with Fists, Strapon Cocks and Enormous Buttplugs (720P)

67% HD 0:29 / 25:30

The Fisting Party Part 3 - Vivienne l'Amour and Sadie Katinka go Wide and Deep with Fists, Strapon Cocks and Enormous Buttplugs (720P)

Clips4sale 1 year ago

Fucked, Fisted & Filled with Cum by Thick Monster Cock TS

71% 0:30 / 43:34

Fucked, Fisted & Filled with Cum by Thick Monster Cock TS

Clips4sale 1 year 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

Rope Tied Oil Catfight and Trib Fight wmv

Rope Tied Oil Catfight and Trib Fight wmv

Clips4sale 1 year ago

Hood Vibrator with Latex Layers

65% HD 0:27 / 15:50

Hood Vibrator with Latex Layers

Clips4sale 1 year ago

Black workout catsuit girl bound and gagged

Black workout catsuit girl bound and gagged

Clips4sale 4 years 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 7 months ago

SISSY STOCKINGS PANTYHOSE CUM CHALLENGE - Sissy Training, Sissy Sluts Training

SISSY STOCKINGS PANTYHOSE CUM CHALLENGE - Sissy Training, Sissy Sluts Training

Clips4sale 1 year ago

Face Your Fag Reality

Face Your Fag Reality

LoyalFans 6 months ago

Deepthroat challenge takes tgirl to her limit

Deepthroat challenge takes tgirl to her limit

Clips4sale 7 months ago

Eve Carmilla Loves Sucking Cock

HD 0:11 / 22:19

Eve Carmilla Loves Sucking Cock

Clips4sale 3 years ago

Pov Boxing - Lissa

Pov Boxing - Lissa

Clips4sale 1 year ago

Dom Hex hook Slutty TS girl ass and dominate her (720p ENG-sub)

HD 0:30 / 24:37

Dom Hex hook Slutty TS girl ass and dominate her (720p ENG-sub)

Clips4sale 1 year ago

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - CLIP 3 OF 5 - MP4

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - CLIP 3 OF 5 - MP4

Clips4sale 1 year 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 - 720p mp4

HD 0:30 / 12:30

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 - 720p mp4

Clips4sale 1 year ago

5 Minute Challenge

46% 4K 0:08 / 6:52

5 Minute Challenge

Clips4sale 4 years ago

Sissy Challenge

Sissy Challenge

Clips4sale 3 years ago

Trans Counselor: You Want Cock

Trans Counselor: You Want Cock

Clips4sale 4 years ago

My New Sissy Anal Slut

HD 0:10 / 25:13

My New Sissy Anal Slut

LoyalFans 3 years ago

Birthday Faggot For BBC

Birthday Faggot For BBC

Clips4sale 3 years ago

Nancy Thompson Foot Tickle & Chill 720p MP4

Nancy Thompson Foot Tickle & Chill 720p MP4

Clips4sale 1 year ago

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

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

Clips4sale 1 year ago

Anubet's Femdomination Wrestling 2

Anubet's Femdomination Wrestling 2

Clips4sale 1 year ago

Rope Tied Oil Catfight and Trib Fight 2 wmv

Rope Tied Oil Catfight and Trib Fight 2 wmv

Clips4sale 1 year ago

Josie Jo Brings Me Home For Her Boyfriend To Worship My Feet (HD1080 WMV)

Josie Jo Brings Me Home For Her Boyfriend To Worship My Feet (HD1080 WMV)

Clips4sale 2 years ago

Wedgie wrestling-4K

Premium 4K 8:48

Wedgie wrestling-4K

Clips4sale 2 years ago

Futa fuck wrestling: Paige Fujiwara vs Petra Mizzurna HD

Futa fuck wrestling: Paige Fujiwara vs Petra Mizzurna HD

Clips4sale 2 years ago

LP-53 Golden Chicken VS Hanzvanderkill

LP-53 Golden Chicken VS Hanzvanderkill

LoyalFans 2 years ago

VIVIENNE L'AMOUR - TGIRL DOUBLE FISTED AND PEGGED WITH HUGE STRAPON (1080P FULL HD)

65% HD 0:26 / 20:40

VIVIENNE L'AMOUR - TGIRL DOUBLE FISTED AND PEGGED WITH HUGE STRAPON (1080P FULL HD)

Clips4sale 2 years ago

VIVIENNE L'AMOUR - TGIRL DOUBLE FISTED AND PEGGED WITH HUGE STRAPON (720P FULL HD)

65% HD 0:26 / 20:40

VIVIENNE L'AMOUR - TGIRL DOUBLE FISTED AND PEGGED WITH HUGE STRAPON (720P FULL HD)

Clips4sale 2 years ago

Gay porn addiction programming mov

63% 0:11 / 6:07

Gay porn addiction programming mov

Clips4sale 2 years ago

House Tour Turned into Trans-4-Trans Fuck Fest

64% 0:30 / 31:17

House Tour Turned into Trans-4-Trans Fuck Fest

Clips4sale 1 year ago

30 Days to Become a Barbie - Sissy Transformation 720p

HD 0:24 / 12:54

30 Days to Become a Barbie - Sissy Transformation 720p

Clips4sale 2 weeks ago

It’s Just Curiosity, Right? Touch the Fear

It’s Just Curiosity, Right? Touch the Fear

Clips4sale 8 months ago

Step-Mommy Physically Dominates The Brat Out Of You (ID # 1768 HD 1080rez)

Step-Mommy Physically Dominates The Brat Out Of You (ID # 1768 HD 1080rez)

Clips4sale 2 years ago

Dom Hex hook Slutty TS girl ass and dominate her (1080p ENG-sub)

HD 0:30 / 24:37

Dom Hex hook Slutty TS girl ass and dominate her (1080p ENG-sub)

Clips4sale 1 year ago

So... You Want My Dick?

So... You Want My Dick?

Clips4sale 8 months ago

Outlaw in: Maid Outfit Escape Challenge 720p

HD 0:30 / 14:29

Outlaw in: Maid Outfit Escape Challenge 720p

Clips4sale 1 year ago

Day 49 Sissy training programme: Sissy Task 07

HD 0:30 / 11:34

Day 49 Sissy training programme: Sissy Task 07

Clips4sale 1 year ago

Streamer Fail

55% HD 0:10 / 10:08

LoyalFans 1 year ago

So You're an Exhibitionist huh?! wmv

HD 0:27 / 10:50

So You're an Exhibitionist huh?! wmv

Clips4sale 2 years ago

Trans Punk Noctella's Intro to Foot Tickling I

Trans Punk Noctella's Intro to Foot Tickling I

Clips4sale 2 years ago

Shemale cock to cock wrestle and sexfight HD

Shemale cock to cock wrestle and sexfight HD

Clips4sale 2 years ago

Jerk Off Encouragement In Silky Panties

Jerk Off Encouragement In Silky Panties

LoyalFans 3 years ago

1 2 3 4

369 results found

Related categories

Tease Funny Competition Basement Game In Control Perverted Training Edging Submissive Freak Barebacking Humiliation Submissive Teen 18+ Toys Uniform Noisy Hazing Begging Teach

Narrow your search

edge challenge try not to cum challenge edging challenge cum challenge jerk off challenge dont cum challenge dildo challenge cock hero challenge joi challenge anal challenge goon challenge cum twice challenge jerk challenge do not cum challenge orgasm challenge stroke challenge backdoor challenge wank challenge stranger challenge mea melone challenge

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.