Challenge Videos - Trans (364)

Outlaw in: Maid Outfit Escape Challenge 720p

HD 0:30 / 14:29

Outlaw in: Maid Outfit Escape Challenge 720p

Clips4sale 1 year ago

Outlaw in: Maid Outfit Escape Challenge 1080p

HD 0:30 / 14:29

Outlaw in: Maid Outfit Escape Challenge 1080p

Clips4sale 1 year ago

Sissy Challenge

HD 0:11 / 12:47

Sissy Challenge

Clips4sale 4 years ago

Futa Wife's Growing Bulge - 720 MP4

61% HD 0:16 / 27:28

Futa Wife's Growing Bulge - 720 MP4

Clips4sale 3 years ago

Futa Wife's Growing Bulge - 720 WMV

HD 0:16 / 27:28

Futa Wife's Growing Bulge - 720 WMV

Clips4sale 3 years ago

Sissy Training Week 3

Sissy Training Week 3

Clips4sale 2 years ago

Fido Futa

Clips4sale 2 years ago

Slap and stroke JOI game B version - CBT

HD 0:10 / 10:48

Slap and stroke JOI game B version - CBT

LoyalFans 2 years ago

Sissy Training Challenge 2: Mastering Makeup and Clothing

Premium HD 10:26

Sissy Training Challenge 2: Mastering Makeup and Clothing

Clips4sale 1 year ago

Sissy Training Challenge: Can You Handle These Tasks?

Premium HD 9:30

Sissy Training Challenge: Can You Handle These Tasks?

Clips4sale 1 year ago

Sissy Training Challenge 3: Embracing Emotional Elegance and Mental Feminization Tasks

Premium HD 9:48

Sissy Training Challenge 3: Embracing Emotional Elegance and Mental Feminization Tasks

Clips4sale 1 year ago

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

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

Clips4sale 1 year ago

Sissy Training Challenge 4: Mastering Relationships and Communication for Deeper Connections

Premium HD 8:40

Sissy Training Challenge 4: Mastering Relationships and Communication for Deeper Connections

Clips4sale 1 year ago

4K - Femcock vs Vibrator Round 1

4K 0:20 / 12:26

4K - Femcock vs Vibrator Round 1

Clips4sale 1 year ago

Regina Twist Vs Troy Trojan

HD 0:49 / 11:27

Regina Twist Vs Troy Trojan

Clips4sale 9 months ago

My Futa Vampire Wife Part Two The Price of Disobedience

63% HD 0:30 / 32:09

My Futa Vampire Wife Part Two The Price of Disobedience

Clips4sale 9 months ago

Hellish Aroma Trapdoor Part 4

Hellish Aroma Trapdoor Part 4

Clips4sale 7 months ago

My SISSY's anal dildo training

My SISSY's anal dildo training

Clips4sale 1 year ago

Sissy Task for Sissies

57% HD 0:20 / 6:11

Sissy Task for Sissies

Clips4sale 1 year ago

combination challenge part 1 (old skool)

combination challenge part 1 (old skool)

LoyalFans 1 year 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

THE 10 LAYERS OF PANTYHOSE OVER THE HEAD BONDAGE CHALLENGE

61% 0:16 / 20:05

THE 10 LAYERS OF PANTYHOSE OVER THE HEAD BONDAGE CHALLENGE

Clips4sale 1 year ago

INTENSIFY DICKLOOP Y - N

INTENSIFY DICKLOOP Y - N

Clips4sale 5 months ago

LARISSA WIN VS ME ?, PART1

LARISSA WIN VS ME ?, PART1

Clips4sale 4 months ago

Don't Pick Up Hitchhikers Part 4 Written by Victoria Vaughn Narrated by Shayla Aspasia

HD 0:30 / 35:08

Don't Pick Up Hitchhikers Part 4 Written by Victoria Vaughn Narrated by Shayla Aspasia

Clips4sale 3 months ago

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

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

Clips4sale 1 year ago

Sissy Task 2 Feminine Training tasks Transformation and Obedience for Princess VivienVee Femdom Girls Next Door Feminization Reprogramming Become a Woman

Sissy Task 2 Feminine Training tasks Transformation and Obedience for Princess VivienVee Femdom Girls Next Door Feminization Reprogramming Become a Woman

Clips4sale 2 years ago

BOOT_COCKCORE: Gay System Override

BOOT_COCKCORE: Gay System Override

Clips4sale 5 months ago

Become His Hungry Cocksucker

Become His Hungry Cocksucker

Clips4sale 3 months ago

Crossdresser Vibed and made to Cum

Crossdresser Vibed and made to Cum

Clips4sale 8 months ago

Taking the Next Step 4K

Taking the Next Step 4K

Clips4sale 8 months ago

Nancy Thompson Foot Tickle & Chill 1080p MP4

Nancy Thompson Foot Tickle & Chill 1080p MP4

Clips4sale 1 year ago

Sissy Task Of The Day #4

Sissy Task Of The Day #4

Clips4sale 3 years ago

Futa Wife's Growing Bulge - 1080 MP4

HD 0:11 / 27:28

Futa Wife's Growing Bulge - 1080 MP4

Clips4sale 3 years ago

Phat Ass Shemale Fernanda Cristine Barebacks a Man

HD 0:26 / 20:41

Phat Ass Shemale Fernanda Cristine Barebacks a Man

Clips4sale 3 years ago

Plaything Sorority Sisters Edition 4K

4K 0:11 / 22:19

Plaything Sorority Sisters Edition 4K

Clips4sale 3 years ago

Sucking Off Three Futa Dick Girls - A Futanari Scene featuring Big Dicks, Femdom POV, and POV Face Fucking - 1080 MP4

HD 0:29 / 11:18

Sucking Off Three Futa Dick Girls - A Futanari Scene featuring Big Dicks, Femdom POV, and POV Face Fucking - 1080 MP4

Clips4sale 3 years ago

Girlfriend Encourages Locktober Chastity Challenge!

HD 0:30 / 12:10

Girlfriend Encourages Locktober Chastity Challenge!

Clips4sale 4 years ago

The Cum Cookie Challenge

61% 0:28 / 13:59

The Cum Cookie Challenge

Clips4sale 2 years ago

So You're an Exhibitionist huh?!

HD 0:27 / 10:50

So You're an Exhibitionist huh?!

Clips4sale 2 years ago

Pussy Free Loser Pledge 2021

HD 0:10 / 11:43

Pussy Free Loser Pledge 2021

LoyalFans 4 years ago

My New Sissy Anal Slut

HD 0:10 / 25:13

My New Sissy Anal Slut

LoyalFans 3 years ago

Epic Hot Gay Kissing and Mouth Fetish 37 - CUSTOM VIDEO - JC Dickerson - Leo Blue - Manpuppy - WMV 1080

HD 0:09 / 31:02

Epic Hot Gay Kissing and Mouth Fetish 37 - CUSTOM VIDEO - JC Dickerson - Leo Blue - Manpuppy - WMV 1080

Clips4sale 3 years ago

Mistress Baton Does The Thousand Fist Challenge HD

4K 0:11 / 37:46

Mistress Baton Does The Thousand Fist Challenge HD

Clips4sale 2 years 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

combination challenge part 2 (old skool)

combination challenge part 2 (old skool)

LoyalFans 1 year ago

Futa cock to cock battle and fucking: Poolside Showdown HD

Futa cock to cock battle and fucking: Poolside Showdown HD

Clips4sale 10 months ago

Mini Me Social Media Challenge

Mini Me Social Media Challenge

Clips4sale 4 years ago

4K - Femcock vs Vibrator Round 2

4K 0:24 / 11:32

4K - Femcock vs Vibrator Round 2

Clips4sale 1 year ago

Top Chef: The Ts Cock Challenge

Top Chef: The Ts Cock Challenge

C4S 2 years ago

Sucky Tekken battle : Futanari, ANAL, POV

Sucky Tekken battle : Futanari, ANAL, POV

LoyalFans 5 months ago

Ms. B Hydration Station Challenge!!

Ms. B Hydration Station Challenge!!

Clips4sale 7 months ago

ANTICHRISTmass Eve: Reprogram Your Aroma Mouth for Unholy Cum

69% 0:42 / 13:52

ANTICHRISTmass Eve: Reprogram Your Aroma Mouth for Unholy Cum

Clips4sale 3 months ago

18 ANTICHRISTmass Eve: AromaTurn You into Cum-Begging Whore

18 ANTICHRISTmass Eve: AromaTurn You into Cum-Begging Whore

Clips4sale 3 months ago

Bondage experiment - Escape Challenge 1

Bondage experiment - Escape Challenge 1

Clips4sale 3 years ago

Face Your Faggot Reality

Face Your Faggot Reality

Clips4sale 2 months ago

Crossdresser Streamer Fail!

HD 0:11 / 10:08

Crossdresser Streamer Fail!

Clips4sale 3 years ago

Teacher Hex’s practical class of biology with TS student girl Sophie (720p ENG-sub) Trans Woman - Trans Blowjob - Trans Fucking

63% HD 0:32 / 56:20

Teacher Hex’s practical class of biology with TS student girl Sophie (720p ENG-sub) Trans Woman - Trans Blowjob - Trans Fucking

Clips4sale 11 months ago

Stepmommys Dirtiest BBC Faggot

57% 0:21 / 11:40

Stepmommys Dirtiest BBC Faggot

Clips4sale 1 year ago

EXTREME FUCKING MACHINE - Part 2 - Vivienne l'Amour and Sadie Katinka continue their anal stretching adventure, fisting, pegging and fucking their wide open slaves

HD 0:28 / 14:49

EXTREME FUCKING MACHINE - Part 2 - Vivienne l'Amour and Sadie Katinka continue their anal stretching adventure, fisting, pegging and fucking their wide open slaves

Clips4sale 1 year 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

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 1 year ago

Uninvited Slumber Party Guest 7 Written by Kylie Gable narrated by Shayla Aspasia

HD 0:30 / 40:44

Uninvited Slumber Party Guest 7 Written by Kylie Gable narrated by Shayla Aspasia

Clips4sale 1 year ago

Submissive BBW bimbo secretary becomes dominant FUTA CEO

Submissive BBW bimbo secretary becomes dominant FUTA CEO

Clips4sale 1 year ago

Wedgie wrestling-mobile friendly

Wedgie wrestling-mobile friendly

Clips4sale 1 year ago

Exposed Sissy Challenge

Exposed Sissy Challenge

Clips4sale 3 years ago

Ari's First Self-Fisting

HD 0:11 / 25:38

Ari's First Self-Fisting

Clips4sale 4 years ago

Dirt and Cream

Clips4sale 4 years ago

The Katie Fox interactive anal challenge

4K 0:29 / 23:48

The Katie Fox interactive anal challenge

Clips4sale 3 years ago

Shemale cock to cock wrestle and sexfight 720p

Shemale cock to cock wrestle and sexfight 720p

Clips4sale 2 years ago

Vanessa vs JC: Arm Wrestling

58% 0:07 / 6:25

Vanessa vs JC: Arm Wrestling

Clips4sale 10 months ago

Best Boys Only- Streaming Only

HD 0:10 / 14:43

Best Boys Only- Streaming Only

LoyalFans 8 months ago

Chained up slave's 30cm deepthroat challenge

HD 0:13 / 22:10

Chained up slave's 30cm deepthroat challenge

Clips4sale 8 months ago

Sucking Off Three Futa Dick Girls - A Futanari Scene featuring Big Dicks, Femdom POV, and POV Face Fucking - 720 MP4

HD 0:29 / 11:18

Sucking Off Three Futa Dick Girls - A Futanari Scene featuring Big Dicks, Femdom POV, and POV Face Fucking - 720 MP4

Clips4sale 3 years ago

BE A GOOD SUB

HD 0:10 / 11:55

LoyalFans 3 years ago

Earn the Strap: Jaq Quicksilver Pegs PonyBoyXXX featuring boot and leather worship, ass eating, and strap-on deepthroat - 1080p

HD 0:30 / 17:15

Earn the Strap: Jaq Quicksilver Pegs PonyBoyXXX featuring boot and leather worship, ass eating, and strap-on deepthroat - 1080p

Clips4sale 2 years ago

Hood Vibrator with Latex Layers - Mobile

HD 0:27 / 15:50

Hood Vibrator with Latex Layers - Mobile

Clips4sale 9 months ago

EXTREME SISSY MENTAL CONDITIONING - Want To Unlock Confidence and Self-Expression? Complete Mental Sissy Training

EXTREME SISSY MENTAL CONDITIONING - Want To Unlock Confidence and Self-Expression? Complete Mental Sissy Training

Clips4sale 1 year ago

No Nut November Spoiler!

No Nut November Spoiler!

Clips4sale 3 years ago

Goddess JOI with Muscle worship and Latex ASMR

HD 0:10 / 11:22

Goddess JOI with Muscle worship and Latex ASMR

LoyalFans 5 months ago

COCKLOADER_ v2. 0: Drain > Deny > Need

COCKLOADER_ v2. 0: Drain > Deny > Need

Clips4sale 5 months ago

5 Star Dick

HD 0:10 / 10:03

LoyalFans 1 month ago

Sissy Task Of The Day #2

Sissy Task Of The Day #2

Clips4sale 3 years ago

Sissy Task Of The Day #4

Sissy Task Of The Day #4

LoyalFans 3 years ago

Slutty Faggot For BBC

Slutty Faggot For BBC

Clips4sale 3 years ago

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

55% 0:18 / 7:26

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

Clips4sale 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

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - CLIP 4 OF 5 - MP4

68% 0:18 / 5:05

SHEMALE DOMINATION - 60 - AGATHA MELO & VICK MENAGE - CLIP 4 OF 5 - MP4

Clips4sale 1 year ago

Stepmommy's Dirtiest BBC Faggot

65% 0:21 / 11:40

Stepmommy's Dirtiest BBC Faggot

Clips4sale 1 year 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

Beautiful Post-Op Swallows My Seed

46% HD 0:30 / 13:39

Beautiful Post-Op Swallows My Seed

Clips4sale 3 years ago

Step-Sis is Definitively The Strongest with The Biggest Cock (ID # 1781 HD 1080rez)

HD 0:11 / 15:26

Step-Sis is Definitively The Strongest with The Biggest Cock (ID # 1781 HD 1080rez)

Clips4sale 2 years ago

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

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

Clips4sale 1 year ago

Futa cock to cock battle and fucking: Poolside Showdown 720p

Futa cock to cock battle and fucking: Poolside Showdown 720p

Clips4sale 10 months ago

Submit to Daddy's Edging Challenge: POV JOI Cum Command Session! - Jaq Quicksilver - strapon, game, ftm, praise - 1080p mp4

HD 0:29 / 12:14

Submit to Daddy's Edging Challenge: POV JOI Cum Command Session! - Jaq Quicksilver - strapon, game, ftm, praise - 1080p mp4

Clips4sale 10 months 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

Secret Sissy Winter Challenge

Secret Sissy Winter Challenge

Clips4sale 1 year ago

Beachball challenge

Beachball challenge

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 - 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

Sissy Femboy Secretary Interview

61% 0:30 / 15:40

Sissy Femboy Secretary Interview

Clips4sale 1 year ago

flawless and fantastic femboi

53% 0:11 / 27:13

flawless and fantastic femboi

Clips4sale 1 year ago

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

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

Clips4sale 1 year ago

Banana Challenge [ft. Goddess Euphonia]

4K 0:44 / 13:36

Banana Challenge [ft. Goddess Euphonia]

Clips4sale 2 years ago

Sissy Karja in trouble (part: 'Selfbondage')

55% 0:11 / 8:18

Sissy Karja in trouble (part: 'Selfbondage')

Clips4sale 2 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

Femboy Pro-Wrestling Jobber Defeated and Sexually Humiliated

48% 0:30 / 18:00

Femboy Pro-Wrestling Jobber Defeated and Sexually Humiliated

Clips4sale 1 year ago

Anal Stretching with Kalin - part 2

HD 0:57 / 20:38

Anal Stretching with Kalin - part 2

Clips4sale 4 years ago

HUGE MONSTERS CHALLENGE FOR THE SISSY SLUT

HUGE MONSTERS CHALLENGE FOR THE SISSY SLUT

Clips4sale 2 years ago

Sip, Sip Sissy!!!

Sip, Sip Sissy!!!

Clips4sale 6 months ago

Taking the Next Step HD

Taking the Next Step HD

Clips4sale 8 months ago

Sissy Task 6 Sissification and Service training Feminization and Beta Mind Fuck Each Task is one step closer to obedience to Princess VivienVee Become the woman you always knew you could be Femdom Crossdresser

Sissy Task 6 Sissification and Service training Feminization and Beta Mind Fuck Each Task is one step closer to obedience to Princess VivienVee Become the woman you always knew you could be Femdom Crossdresser

Clips4sale 2 years ago

Sissy Photoshoot Challenge

HD 0:25 / 11:34

Sissy Photoshoot Challenge

Clips4sale 2 years ago

Delia Releases a Kept Man From Chastity Then Locks Him Down with Her Cock!

Delia Releases a Kept Man From Chastity Then Locks Him Down with Her Cock!

C4S 2 years ago

Week 22: A Naughty Task for Sissy Sluts (MP4)

Week 22: A Naughty Task for Sissy Sluts (MP4)

Clips4sale 2 years ago

Futa Wife's Growing Bulge - 1080 WMV

HD 0:16 / 27:28

Futa Wife's Growing Bulge - 1080 WMV

Clips4sale 3 years ago

Chun Li Cosplayer Escape Challenge Part 2

Chun Li Cosplayer Escape Challenge Part 2

Clips4sale 3 years ago

Rope Tied Oil Catfight and Trib Fight 3 wmv

66% 0:30 / 12:27

Rope Tied Oil Catfight and Trib Fight 3 wmv

Clips4sale 1 year ago

EXTREME FUCKING MACHINE - Part 2 - Vivienne l'Amour and Sadie Katinka continue their anal stretching adventure, fisting, pegging and fucking their wide open slaves (720p)

HD 0:28 / 14:49

EXTREME FUCKING MACHINE - Part 2 - Vivienne l'Amour and Sadie Katinka continue their anal stretching adventure, fisting, pegging and fucking their wide open slaves (720p)

Clips4sale 1 year ago

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

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

Clips4sale 1 year ago

Futa Story: Insubordination - Ft Imilia Audley

4K 0:29 / 12:27

Futa Story: Insubordination - Ft Imilia Audley

Clips4sale 1 year ago

1 2 3 4

364 results found

Related categories

Competition Tease Training WTF Edging See Through Contest Hazing Encouragement Nipple Piercing Stripper Milking Table CFNM Instructions Submissive Jerk Off Encouragement Freak Submissive Teen 18+ Stripping Kinky

Narrow your search

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