Challenge Videos - Trans (1,315)

Astolfo - Ahegao hand job challenge

HD 1:01 / 11:45

Astolfo - Ahegao hand job challenge

FapHouse 3 years ago

Transsexual Anal Challenge in Brazil - Episode #08

HD 1:01 / 23:12

Transsexual Anal Challenge in Brazil - Episode #08

FapHouse 5 years ago

Blonde with a Big Ass Accepted the Challenge of Fucking Two

HD 0:39 / 23:40

Blonde with a Big Ass Accepted the Challenge of Fucking Two

FapHouse 1 year ago

Oral Fixation Device Bondage Deepthroat Challenge Submissive Tgirl Slut

Premium HD 28:01

Oral Fixation Device Bondage Deepthroat Challenge Submissive Tgirl Slut

Sheer 1 year ago

Transsexual Anal Challenge in Brazil - Episode #13

HD 1:01 / 17:49

Transsexual Anal Challenge in Brazil - Episode #13

FapHouse 5 years ago

The Princess Udders Six Minute Skittle Spank Challenge

The Princess Udders Six Minute Skittle Spank Challenge

FapHouse 6 months ago

Stunning Pietra Raw Fucks Her Lucky Fella

63% HD 1:01 / 25:08

Stunning Pietra Raw Fucks Her Lucky Fella

FapHouse 4 months ago

Self-training 49: M-leg Split Challenge at a Beach

Self-training 49: M-leg Split Challenge at a Beach

FapHouse 9 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 9 months ago

Feminization challenge joi $10

Feminization challenge joi $10

Clips4sale 8 months 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 3 years ago

CUM EATING CHALLENGE, CEI - Stepmom Helps You eat Cum Comfortably like A Pro, ABDL Mind Fuck

CUM EATING CHALLENGE, CEI - Stepmom Helps You eat Cum Comfortably like A Pro, ABDL Mind Fuck

Clips4sale 2 years ago

I Ruined Your Nnn

HD 0:39 / 17:37

I Ruined Your Nnn

FapHouse 9 months ago

Taking the Next Step 4K

Taking the Next Step 4K

Clips4sale 1 year ago

LARISSA WIN VS ME ?, PART1

LARISSA WIN VS ME ?, PART1

Clips4sale 10 months ago

BOOT_COCKCORE: Gay System Override

BOOT_COCKCORE: Gay System Override

Clips4sale 11 months ago

INTENSIFY DICKLOOP Y - N

INTENSIFY DICKLOOP Y - N

Clips4sale 11 months ago

Two Lesbian Girls Sucking Shemale Huge Cock Cumming

Two Lesbian Girls Sucking Shemale Huge Cock Cumming

FapHouse 2 months ago

Cross Examination (4K MP4) Tilly McReese: Crossdressing, Sissification, Nylon, Feminization, Femdom

Premium 4K 15:28

Cross Examination (4K MP4) Tilly McReese: Crossdressing, Sissification, Nylon, Feminization, Femdom

Clips4sale 2 months ago

Michelle Ernandes Fun in Hurghada Hotel - Episode Ii - Total Morning Satisfaction

HD 0:39 / 24:55

Michelle Ernandes Fun in Hurghada Hotel - Episode Ii - Total Morning Satisfaction

FapHouse 2 months ago

Selfie Mountain Day, so I Tried the Challenge of Showing My Boobs!

Selfie Mountain Day, so I Tried the Challenge of Showing My Boobs!

FapHouse 2 months ago

Monster Dildo Challenge Depth Training

Monster Dildo Challenge Depth Training

FapHouse 1 month ago

Self-training No. 96: Exhibitionist Walk with Visible Used Sanitary Napkin

HD 1:01 / 25:14

Self-training No. 96: Exhibitionist Walk with Visible Used Sanitary Napkin

FapHouse 8 months ago

Foot Focused Tickling Bundle - Tomboy Jaq Quicksilver Tickled 3x on Armpits and Feet in Bondage and Predicaments - oiled feet, sensual tickle - 1080p mp4

HD 0:30 / 39:34

Foot Focused Tickling Bundle - Tomboy Jaq Quicksilver Tickled 3x on Armpits and Feet in Bondage and Predicaments - oiled feet, sensual tickle - 1080p mp4

Clips4sale 7 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 2 years ago

Three Friends Get Locked In Sunroom Butt Naked

Three Friends Get Locked In Sunroom Butt Naked

Clips4sale 8 months ago

Self-training No. 94: Wearing Sanitary Pads and Tampons for an Exposure Walk - Part 1

HD 0:39 / 19:36

Self-training No. 94: Wearing Sanitary Pads and Tampons for an Exposure Walk - Part 1

FapHouse 8 months ago

Human Pretzel Challenge

Human Pretzel Challenge

FapHouse 6 months ago

Desperate FTM Edging Handcuffed | Trans Twink Cobalt FTM Edging With Vibrator While Restrained, Clothed Masturbation, Orgasm Control

Desperate FTM Edging Handcuffed | Trans Twink Cobalt FTM Edging With Vibrator While Restrained, Clothed Masturbation, Orgasm Control

Clips4sale 7 months ago

No. 262 Posing as if Laying Eggs

No. 262 Posing as if Laying Eggs

FapHouse 2 months ago

Fashion Show: Our Sissy in Front of 2 Sexy Judges!

57% HD 0:39 / 16:24

Fashion Show: Our Sissy in Front of 2 Sexy Judges!

FapHouse 3 months ago

Eating Donuts on all fours challenge! No Hands!

Premium 4K 4:39

Eating Donuts on all fours challenge! No Hands!

Clips4sale 3 months ago

Gym Twink Bathroom Fuck - Monster Hard Positions

63% 1:01 / 15:10

Gym Twink Bathroom Fuck - Monster Hard Positions

FapHouse 3 months ago

Sissy Training Day 1 - First Steps of Transformation

Sissy Training Day 1 - First Steps of Transformation

FapHouse 4 months ago

Stricttoxxx

Premium HD 26:18

Clips4sale 4 months ago

So You're an Exhibitionist huh?!

HD 0:27 / 10:50

So You're an Exhibitionist huh?!

Clips4sale 2 years ago

Asmr Closeup of My Pussy Being Edged with My Vibrator

Asmr Closeup of My Pussy Being Edged with My Vibrator

FapHouse 3 weeks ago

Fart Challenge Two Girls PVC Leggings Big ass and Bloated Belly

Premium 4K 17:31

Fart Challenge Two Girls PVC Leggings Big ass and Bloated Belly

Clips4sale 3 weeks ago

Cocomelon Ragga Challenge Dark Vibes & Wild Moves Lunar Body (full)

Cocomelon Ragga Challenge Dark Vibes & Wild Moves Lunar Body (full)

FapHouse 2 weeks ago

Cocomelon Ragga Challenge Dark Vibes & Wild Moves Lunar Body (full)

Cocomelon Ragga Challenge Dark Vibes & Wild Moves Lunar Body (full)

FapHouse 1 week ago

Sissy Anal Endurance Test: Holding Massive Dildo Deep Inside Until Full Gape / Intense Slow Anal Stretch: Sissy Accommodation Challenge with Thick Toy

Premium HD 7:00

Sissy Anal Endurance Test: Holding Massive Dildo Deep Inside Until Full Gape / Intense Slow Anal Stretch: Sissy Accommodation Challenge with Thick Toy

XVideosRed 1 week ago

Emy Milks Her Tourist Trainer

HD 0:10 / 39:46

Emy Milks Her Tourist Trainer

LoyalFans 1 day ago

I Hit It Last

Premium HD 24:01

TransAngels 6 years ago

Transexual Anal Challenge in Brazil - Episode #19

HD 0:39 / 20:55

Transexual Anal Challenge in Brazil - Episode #19

FapHouse 5 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

4K - Femcock vs Vibrator Round 2

4K 0:24 / 11:32

4K - Femcock vs Vibrator Round 2

Clips4sale 2 years ago

Sweaty Dirty Creamy Black Panty Cardio

HD 0:39 / 47:13

Sweaty Dirty Creamy Black Panty Cardio

FapHouse 1 year ago

Ladyboys Uncovered (Katoey) Scene 1

Ladyboys Uncovered (Katoey) Scene 1

Erotik 4 years ago

Become His Hungry Cocksucker

Become His Hungry Cocksucker

Clips4sale 9 months ago

Manhandled and Milked

Manhandled and Milked

Clips4sale 9 months ago

Stunning Sissy Garage DID Chair Bondage Struggle Session

Premium 4K 49:55

Stunning Sissy Garage DID Chair Bondage Struggle Session

Clips4sale 3 months ago

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

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

Clips4sale 10 months ago

Self-training No. 26: Exposure Walk with Urination

Self-training No. 26: Exposure Walk with Urination

FapHouse 10 months ago

Mirella likes to deal with big men

Mirella likes to deal with big men

Clips4sale 1 year ago

Danika Deep vs KaneVision Competitive Wrestling

Danika Deep vs KaneVision Competitive Wrestling

Clips4sale 4 years ago

Sissy cutie tackles a big dick

Sissy cutie tackles a big dick

FapHouse 3 years ago

Femdom pegging with huge dildo for big cock sissy Lucy

HD 0:39 / 18:04

Femdom pegging with huge dildo for big cock sissy Lucy

FapHouse 4 years ago

Blonde Slender Slut Happy Ending in Her Mouth

66% HD 0:30 / 13:39

Blonde Slender Slut Happy Ending in Her Mouth

Clips4sale 3 years 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

The Katie Fox interactive anal challenge

4K 0:29 / 23:48

The Katie Fox interactive anal challenge

Clips4sale 3 years ago

Big dick, big ass, big tits, big cum!

HD 1:01 / 13:42

Big dick, big ass, big tits, big cum!

FapHouse 8 years ago

Cum Injection and Big Toys for the Perfect Pegging Sissygasm

57% HD 1:01 / 17:34

Cum Injection and Big Toys for the Perfect Pegging Sissygasm

FapHouse 1 year ago

cum play with me interactive challenge joi

HD 0:30 / 23:48

cum play with me interactive challenge joi

PornBox 3 years ago

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

Clips4sale 1 year ago

Futanari Milk Challenge 1

Premium HD 5:04

Futanari Milk Challenge 1

Sheer 1 year ago

Vanessa vs JC: Arm Wrestling

58% 0:07 / 6:25

Vanessa vs JC: Arm Wrestling

Clips4sale 1 year ago

GlitterGiiiirl´s Deepthroat Challenge: Intense Vibrator Gagging & Gag Reflex Play

GlitterGiiiirl´s Deepthroat Challenge: Intense Vibrator Gagging & Gag Reflex Play

Clips4sale 1 year ago

Best Boys Only- Streaming Only

HD 0:10 / 14:43

Best Boys Only- Streaming Only

LoyalFans 1 year ago

Submit to Daddy's Edging Challenge: POV JOI Cum Command Session!

Premium HD 12:14

Submit to Daddy's Edging Challenge: POV JOI Cum Command Session!

Sheer 1 year ago

oral fixation device bondage deepthroat challenge submissive tgirl slut

HD 0:29 / 28:01

oral fixation device bondage deepthroat challenge submissive tgirl slut

PornBox 1 year ago

Stepmommys Dirtiest BBC Faggot

57% 0:21 / 11:40

Stepmommys Dirtiest BBC Faggot

Clips4sale 2 years ago

Wedgie wrestling-mobile friendly

Wedgie wrestling-mobile friendly

Clips4sale 2 years ago

Submissive BBW bimbo secretary becomes dominant FUTA CEO

Submissive BBW bimbo secretary becomes dominant FUTA CEO

Clips4sale 2 years 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 2 years ago

Francis Malice Cheerleader 1h Anal Casting Part 1

HD 1:01 / 1:01:39

Francis Malice Cheerleader 1h Anal Casting Part 1

FapHouse 2 years 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 3 years ago

Part 1/4 Chastity Release After a Month: Humiliating Penetration and Degradation

47% HD 1:01 / 6:03

Part 1/4 Chastity Release After a Month: Humiliating Penetration and Degradation

FapHouse 1 year ago

Ariana Slim Has a Big Tool for You

Ariana Slim Has a Big Tool for You

Flirt4Free 9 years ago

Alexa Readman Loves Taking BBC All the Way

Alexa Readman Loves Taking BBC All the Way

FapHouse 2 years ago

Transsexual anal challenge in Brazil - Episode #08

Transsexual anal challenge in Brazil - Episode #08

FapHouse 1 year ago

Part 2/4 Chastity Release After a Month: Humiliating Penetration and Degradation

65% HD 0:39 / 4:37

Part 2/4 Chastity Release After a Month: Humiliating Penetration and Degradation

FapHouse 1 year ago

Transsexual anal challenge in Brazil - Episode #09

Transsexual anal challenge in Brazil - Episode #09

FapHouse 1 year ago

Ari's First Self-Fisting

HD 0:11 / 25:38

Ari's First Self-Fisting

Clips4sale 4 years ago

Redhead Transhappy Snip

4K 0:20 / 17:18

Redhead Transhappy Snip

AdultPrime 15 years ago

Big cock transsexual gives deep anal to big tits MILF

63% 0:39 / 33:27

Big cock transsexual gives deep anal to big tits MILF

FapHouse 4 years ago

britney assfucked & big facial nr174

britney assfucked & big facial nr174

PornBox 10 years ago

The Cross-dresser Puts a Glass Ball in Her Anus and Writhes

The Cross-dresser Puts a Glass Ball in Her Anus and Writhes

FapHouse 1 year ago

Humiliation & Mud Play – Boo Hoo Crybaby Training Femdom – Sara Desire XO – HD MP4 1080p

Humiliation & Mud Play – Boo Hoo Crybaby Training Femdom – Sara Desire XO – HD MP4 1080p

Clips4sale 1 year ago

Sissy Jessica Bloom Eats Her Own Cum off a Cake! - Edging Sounding and Cumplay

57% HD 0:39 / 19:46

Sissy Jessica Bloom Eats Her Own Cum off a Cake! - Edging Sounding and Cumplay

FapHouse 1 year ago

SISSY THINGS: 3 panties challenge

SISSY THINGS: 3 panties challenge

Clips4sale 1 year ago

Oral Fixation Device Bondage Deepthroat Challenge Submissive Tgirl Slut

Premium HD 28:02

Oral Fixation Device Bondage Deepthroat Challenge Submissive Tgirl Slut

XNXXGold 1 year ago

Fuck machine and videogames

Fuck machine and videogames

FapHouse 5 years ago

BE A GOOD SUB

HD 0:10 / 11:55

LoyalFans 4 years ago

snack challenge

snack challenge

Clips4sale 2 years ago

Shemale cock to cock wrestle and sexfight 720p

Shemale cock to cock wrestle and sexfight 720p

Clips4sale 2 years ago

Crossdresser Streamer Fail!

HD 0:11 / 10:08

Crossdresser Streamer Fail!

Clips4sale 4 years ago

lesbian pee swallowing girls - threesome pee challenge

HD 0:30 / 35:35

lesbian pee swallowing girls - threesome pee challenge

PornBox 1 year ago

FtM Trans Bussy Fuck with Inflatable Dildo - Jaq Quicksilver Fucks His Ass with Huge Rubber Dildo on the Quest for an Anal Gape - 4k mp4

4K 0:30 / 14:32

FtM Trans Bussy Fuck with Inflatable Dildo - Jaq Quicksilver Fucks His Ass with Huge Rubber Dildo on the Quest for an Anal Gape - 4k mp4

Clips4sale 1 year ago

No Nut Challenge Fail

Premium 4K 30:09

No Nut Challenge Fail

Freeuse 5 years ago

No Nut Challenge Fail

Premium 4K 30:09

No Nut Challenge Fail

Pervz 5 years ago

Monster Dildo Challenge Depth Training

Monster Dildo Challenge Depth Training

FapHouse 1 month ago

This Will Blow Your Mind: Vaniity Is Back

HD 0:39 / 35:43

This Will Blow Your Mind: Vaniity Is Back

FapHouse 6 months ago

My Playlist Challenge

My Playlist Challenge

FapHouse 6 months ago

Playlist Edging Challenge

Playlist Edging Challenge

FapHouse 6 months ago

Edging Challenge

HD 1:01 / 13:24

Edging Challenge

FapHouse 1 month ago

Tgirl gets fucked while playing console

Tgirl gets fucked while playing console

Clips4sale 1 month ago

Tiktok Naked Challenge Gay Twink Femboy Blonde

Tiktok Naked Challenge Gay Twink Femboy Blonde

FapHouse 1 month ago

Pussy Stretching With Huge Dildo

Pussy Stretching With Huge Dildo

Clips4sale 10 months ago

Sucky Tekken battle : Futanari, ANAL, POV

Sucky Tekken battle : Futanari, ANAL, POV

LoyalFans 10 months ago

Lilium - My submissive ex tries tape bondage escape challenge - 4K

Premium 4K 14:22

Lilium - My submissive ex tries tape bondage escape challenge - 4K

Clips4sale 2 months ago

Competing with My Trans Stepsister to See Who Cums First

65% HD 0:39 / 11:58

Competing with My Trans Stepsister to See Who Cums First

FapHouse 2 months ago

Dirty pig's best cbt adventure

HD 0:10 / 13:06

Dirty pig's best cbt adventure

LoyalFans 3 months ago

Sissy Training Day 1 - First Steps of Transformation

Sissy Training Day 1 - First Steps of Transformation

FapHouse 4 months ago

Sissy Goes to Work in Heels! Pantsuit + Thong

Sissy Goes to Work in Heels! Pantsuit + Thong

Clips4sale 3 months ago

300 Millimeters the Great Challenge

300 Millimeters the Great Challenge

FapHouse 10 months ago

Extreme Hogtie with Rear High-Arm Binder, 12cm Heels, 5-Egg Trainer, Intense Electro & Vibrator Overload, Overnight Suspension Placement

Premium 1:38:31

Extreme Hogtie with Rear High-Arm Binder, 12cm Heels, 5-Egg Trainer, Intense Electro & Vibrator Overload, Overnight Suspension Placement

Clips4sale 9 months ago

The 34 Centimetre Rigid Challenge Taken up

The 34 Centimetre Rigid Challenge Taken up

FapHouse 9 months ago

My playlist challenge

Premium HD 4:09

My playlist challenge

XVideosRed 7 months ago

Ponygirl omocha - Orgasm and Pain Training

Ponygirl omocha - Orgasm and Pain Training

Clips4sale 10 months ago

His stick is very big, and he challenged me to try it.

Premium HD 25:12

His stick is very big, and he challenged me to try it.

XNXXGold 8 months ago

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