Challenge Videos - Trans (1,266)

Cruising in Illescas Toledo Spain Are Panties Black

64% HD 1:01 / 5:54

Cruising in Illescas Toledo Spain Are Panties Black

FapHouse 3 months ago

Extreme Deepthroat Challenge of the Gagging Reflex - Pig Pushes Its Limits

66% 1:01 / 9:58

Extreme Deepthroat Challenge of the Gagging Reflex - Pig Pushes Its Limits

FapHouse 4 months ago

TS Takes 3-Inch Anal Beads & Glass Dildo O

HD 0:30 / 28:03

TS Takes 3-Inch Anal Beads & Glass Dildo O

Clips4sale 4 months ago

Monster Dildo Challenge Depth Training

65% 0:39 / 10:37

Monster Dildo Challenge Depth Training

FapHouse 1 month ago

Straight Moroccan Guy Enjoys His First Time with a Sexy Transgender Woman

Premium HD 20:29

Straight Moroccan Guy Enjoys His First Time with a Sexy Transgender Woman

GayArabClub 5 years ago

Fart Challenge Two Girls PVC Leggings Big ass and Bloated Belly

Premium HD 17:32

Fart Challenge Two Girls PVC Leggings Big ass and Bloated Belly

XVideosRed 1 week ago

Selfie #tell Me Your Favorite Lingerie Brand! I Challenged Myself to Tell Me My Favorite Lingerie Brand!

FapHouse 4 days ago

Rogue Adventures 44 (Evil Angel - Joey Silvera) Scene 4

Rogue Adventures 44 (Evil Angel - Joey Silvera) Scene 4

Erotik 9 years ago

Cucked By The Pole Dancer

Premium HD 33:25

Cucked By The Pole Dancer

TransAngels 4 years ago

Upside Down BJ & Facefuck

Upside Down BJ & Facefuck

APClips 3 months ago

Slutty Sissy Kitchen Cleaning in High Heel Pumps and Ankle Cuffs plus Cock Teasing

Slutty Sissy Kitchen Cleaning in High Heel Pumps and Ankle Cuffs plus Cock Teasing

Clips4sale 1 year ago

Futa cock to cock battle and fucking: Poolside Showdown LOW

65% HD 0:30 / 6:45

Futa cock to cock battle and fucking: Poolside Showdown LOW

Clips4sale 1 year ago

Submit to Daddy&#039_s Edging Challenge: POV JOI Cum Command Session!

Premium HD 12:14

Submit to Daddy&#039_s Edging Challenge: POV JOI Cum Command Session!

XNXXGold 1 year ago

Sissy Task for Sissies

Sissy Task for Sissies

LoyalFans 2 years ago

Drink Your Favorite Beverage!

Drink Your Favorite Beverage!

FapHouse 5 months ago

Secretary Caught Shemale Boss Fucking Sexy Girl In Office

Secretary Caught Shemale Boss Fucking Sexy Girl In Office

FapHouse 2 months ago

Trainer's Training Session No. 91: Relaxing in a Hammock with an Open Crotch

Trainer's Training Session No. 91: Relaxing in a Hammock with an Open Crotch

FapHouse 7 months ago

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

HD 0:39 / 25:14

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

FapHouse 7 months ago

The Queen Is Waiting for Someone to Come to Her Place.

HD 1:01 / 20:43

The Queen Is Waiting for Someone to Come to Her Place.

FapHouse 1 year ago

Sexy Jade Trolling for Poling

HD 0:39 / 44:42

Sexy Jade Trolling for Poling

FapHouse 1 year ago

Nancy Thompson's Burping Tease – Dominant Gassy Play (SD 720p WMV)

Nancy Thompson's Burping Tease – Dominant Gassy Play (SD 720p WMV)

Clips4sale 1 year ago

30 Minutes On The Elliptical While Getting Vibed With a Remote Controlled Butt Plug Challenge

Premium HD 28:15

30 Minutes On The Elliptical While Getting Vibed With a Remote Controlled Butt Plug Challenge

Sheer 2 years 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 1 year ago

Dominant Big Dick Trans Woman&#039_s Stroke Challenge &ndash_ 10-Minute Masturbation with Explosive Cumshot

Premium HD 11:56

Dominant Big Dick Trans Woman&#039_s Stroke Challenge &ndash_ 10-Minute Masturbation with Explosive Cumshot

XVideosRed 2 years ago

Futanari Milk Challenge 3

Premium HD 6:03

Futanari Milk Challenge 3

XNXXGold 1 year ago

Sissy Katja is no longer an anal virgin!

Sissy Katja is no longer an anal virgin!

Clips4sale 3 years ago

Femdom pegging with huge dildo for big cock sissy Lucy

HD 1:01 / 18:04

Femdom pegging with huge dildo for big cock sissy Lucy

FapHouse 4 years ago

Transsexual Anal Challenge in Brazil - Episode #07

65% HD 1:01 / 19:37

Transsexual Anal Challenge in Brazil - Episode #07

FapHouse 5 years 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

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 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

Transsexual anal challenge in Brazil - Episode #12

Transsexual anal challenge in Brazil - Episode #12

FapHouse 1 year ago

My SISSY's anal dildo training

My SISSY's anal dildo training

Clips4sale 2 years ago

Girl in pantyhose will open her legs to Sit on an erected bazooka

Girl in pantyhose will open her legs to Sit on an erected bazooka

FapHouse 8 years ago

Transsexual Anal Challenge in Brazil - Episode #04

HD 1:01 / 26:32

Transsexual Anal Challenge in Brazil - Episode #04

FapHouse 5 years 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

Trans Girl Gives Step Sis a Big Dick Ride Challenge

Trans Girl Gives Step Sis a Big Dick Ride Challenge

FapHouse 1 year ago

Transsexual anal challenge in Brazil - Episode #16

Transsexual anal challenge in Brazil - Episode #16

FapHouse 1 year ago

Challenge to a new huge dildo -Part 5

HD 1:01 / 19:59

Challenge to a new huge dildo -Part 5

FapHouse 4 years ago

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

HD 0:39 / 18:03

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

FapHouse 1 year 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

Transexual Anal Challenge in Brazil - Episode #19

HD 1:01 / 20:55

Transexual Anal Challenge in Brazil - Episode #19

FapHouse 5 years ago

Got Punished by 10 Huge Men BDSM Challenge

Got Punished by 10 Huge Men BDSM Challenge

FapHouse 1 year ago

Transsexual Anal Challenge in Brazil - Episode #13

HD 0:39 / 17:49

Transsexual Anal Challenge in Brazil - Episode #13

FapHouse 5 years ago

Surrounded by shemale cock

HD 0:39 / 26:10

Surrounded by shemale cock

FapHouse 8 years ago

Transsexual Anal Challenge in Brazil - Episode #10

Transsexual Anal Challenge in Brazil - Episode #10

FapHouse 5 years ago

Transsexual Anal Challenge in Brazil - Episode #20

HD 0:39 / 33:33

Transsexual Anal Challenge in Brazil - Episode #20

FapHouse 5 years ago

Crossdress cosplay Rosalina dildos and panties

Crossdress cosplay Rosalina dildos and panties

FapHouse 7 years ago

Outlaw in: Maid Outfit Escape Challenge 1080p

HD 0:30 / 14:29

Outlaw in: Maid Outfit Escape Challenge 1080p

Clips4sale 1 year ago

Cosplay Puv Daphne Burp Challenge with Scooby Taser

Cosplay Puv Daphne Burp Challenge with Scooby Taser

FapHouse 1 year ago

Sexu Trans Girl Krystall Cox in Pink Fishnets Riding a Huge Dildo

HD 0:39 / 19:00

Sexu Trans Girl Krystall Cox in Pink Fishnets Riding a Huge Dildo

FapHouse 1 year ago

Challenging My Neighbors - Cum Rain, Piss

HD 0:39 / 11:24

Challenging My Neighbors - Cum Rain, Piss

FapHouse 1 year ago

Francis Malice Cheerleader 1h Anal Casting Part 1

HD 0:39 / 1:01:39

Francis Malice Cheerleader 1h Anal Casting Part 1

FapHouse 2 years ago

4K - Femcock vs Vibrator Round 1

4K 0:20 / 12:26

4K - Femcock vs Vibrator Round 1

Clips4sale 2 years ago

Sissy Training Week 3

Sissy Training Week 3

Clips4sale 3 years ago

College Cheerleader Has an Illicit Affair

College Cheerleader Has an Illicit Affair

FapHouse 1 year ago

Step Into the Inviting Warmth of the Shower with Me, Adorned in Your Stylish One-piece Swimsuit Let's Create a Hot Wet Moment

65% HD 1:01 / 11:25

Step Into the Inviting Warmth of the Shower with Me, Adorned in Your Stylish One-piece Swimsuit Let's Create a Hot Wet Moment

FapHouse 2 years ago

Pale Beauty Memphi Hart Loves BBC Bareback

Pale Beauty Memphi Hart Loves BBC Bareback

FapHouse 2 years ago

7 Ladyboys Cum Contest

48% 1:01 / 1:03:25

7 Ladyboys Cum Contest

FapHouse 2 years ago

pale beauty memphi hart loves bbc bareback

HD 0:30 / 26:54

pale beauty memphi hart loves bbc bareback

AnalVids 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 2 years ago

Vicki's JOI Orgasm Challenge!

Vicki's JOI Orgasm Challenge!

FapHouse 2 years ago

Challenge to a new huge dildo -Part 4

HD 1:01 / 18:01

Challenge to a new huge dildo -Part 4

FapHouse 4 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 0:39 / 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

Slap and stroke JOI game B version - CBT

65% HD 0:10 / 10:48

Slap and stroke JOI game B version - CBT

LoyalFans 2 years ago

Transsexual Anal Challenge in Brazil - Episode #18

HD 1:01 / 20:20

Transsexual Anal Challenge in Brazil - Episode #18

FapHouse 5 years 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 4 years ago

Ebony beauty Brooke Morgan solo

66% HD 0:39 / 23:13

Ebony beauty Brooke Morgan solo

FapHouse 4 years ago

hot tranny kalliny nomura fucks the technician and cums in his mouth dt531

HD 0:59 / 33:37

hot tranny kalliny nomura fucks the technician and cums in his mouth dt531

PornBox 3 years ago

Cum Eating at Work CEI JOI

Cum Eating at Work CEI JOI

Clips4sale 3 years ago

Regina Twist Vs Troy Trojan

HD 0:49 / 11:27

Regina Twist Vs Troy Trojan

Clips4sale 1 year ago

30 Day's of Cum Video Challenge Video #1

30 Day's of Cum Video Challenge Video #1

FapHouse 1 year ago

Vanessa vs JC: Arm Wrestling wmv

Vanessa vs JC: Arm Wrestling wmv

Clips4sale 1 year ago

futanari milk challenge 2

futanari milk challenge 2

PornBox 1 year ago

futanari milk challenge 1

futanari milk challenge 1

PornBox 1 year ago

FULL CLIP!! Fun with two small-dick losers! Nasty suffer for their tiny cocks! Chastity SPH

62% HD 0:29 / 13:12

FULL CLIP!! Fun with two small-dick losers! Nasty suffer for their tiny cocks! Chastity SPH

Clips4sale 1 year ago

combination challenge part 1 (old skool)

combination challenge part 1 (old skool)

LoyalFans 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 2 years ago

COMPILATION OF SISSY CUMS IN CHASTITY. SISSY IN STOCKINGS AND SHINY PANTIES SHOWS HER CLIT IN A CHASTITY BELT. HER COCK IS CLOSED IN A CAGE.

Premium HD 8:18

COMPILATION OF SISSY CUMS IN CHASTITY. SISSY IN STOCKINGS AND SHINY PANTIES SHOWS HER CLIT IN A CHASTITY BELT. HER COCK IS CLOSED IN A CAGE.

XNXXGold 3 years ago

Boss Roberta Cortes demands sex from job applicant Hex (720p English) Trans Woman - Trans Cock Sucker - Trans Fucking - Trans Domination

HD 0:38 / 30:37

Boss Roberta Cortes demands sex from job applicant Hex (720p English) Trans Woman - Trans Cock Sucker - Trans Fucking - Trans Domination

Clips4sale 2 months ago

SISSY PUBLIC EXPOSURE CHALLENGE

Premium HD 22:27

SISSY PUBLIC EXPOSURE CHALLENGE

Clips4sale 3 months ago

Gym Twink Bathroom Fuck - Monster Hard Positions

63% 0:39 / 15:10

Gym Twink Bathroom Fuck - Monster Hard Positions

FapHouse 2 months ago

Ultimate Sissy Marathon

HD 0:20 / 33:23

Ultimate Sissy Marathon

Clips4sale 2 months ago

Heyaa Hope You

FapHouse 2 months ago

Heyaa Hope You

FapHouse 2 months ago

Hands Free Thigh High Removal- Starring Smokin Rose

Premium HD 3:46

Hands Free Thigh High Removal- Starring Smokin Rose

Clips4sale 1 month ago

Selfie Chikubim! Pinch and Show off Her Nipples on Both Sides! I Took on the Challenge.

Selfie Chikubim! Pinch and Show off Her Nipples on Both Sides! I Took on the Challenge.

FapHouse 1 month ago

No Angel

Premium HD 27:05

TransAngels 6 years ago

Edging Challenge

Edging Challenge

FapHouse 2 weeks ago

Fart Challenge Two Girls PVC Leggings Big ass and Bloated Belly

Premium HD 17:32

Fart Challenge Two Girls PVC Leggings Big ass and Bloated Belly

XNXXGold 1 week ago

Tiny FTM Boy Pussy vs GIANT Raw Cock – Bareback Stretch Challenge + Creampue

HD 0:25 / 16:33

Tiny FTM Boy Pussy vs GIANT Raw Cock – Bareback Stretch Challenge + Creampue

Clips4sale 1 week ago

Selfie #tell Me Your Favorite Lingerie Brand! I Challenged Myself to Tell Me My Favorite Lingerie Brand!

FapHouse 5 days ago

Ice Bucket Boobs Challenge ?

Premium HD 5:26

Ice Bucket Boobs Challenge ?

Clips4sale 1 month ago

Exposed in Park Walks and Parking Lots

65% HD 0:39 / 5:23

Exposed in Park Walks and Parking Lots

FapHouse 10 months ago

Deep Penetration of a Slut's Ass

Deep Penetration of a Slut's Ass

FapHouse 11 months ago

Cumming at the Same Moment Is Pretty Challenging! ( G075 )

Cumming at the Same Moment Is Pretty Challenging! ( G075 )

FapHouse 11 months ago

Starting Tonight

Starting Tonight

FapHouse 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 - 1080p WMV

65% HD 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 - 1080p WMV

Clips4sale 1 year ago

Exposed in Park Walks and Parking Lots

Exposed in Park Walks and Parking Lots

FapHouse 10 months ago

Edging Challenge Day 1 3 Days of Cum 1028205

HD 1:01 / 31:18

Edging Challenge Day 1 3 Days of Cum 1028205

FapHouse 10 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 10 months ago

Outdoor Workout with Vibrator for Ass and Cock! Tranny Cums Straight Into Her Shorts!

55% HD 0:39 / 5:46

Outdoor Workout with Vibrator for Ass and Cock! Tranny Cums Straight Into Her Shorts!

FapHouse 7 months ago

How Deep Can You Go? Watch Me Push a 3 Ball to the Limit

HD 0:39 / 10:25

How Deep Can You Go? Watch Me Push a 3 Ball to the Limit

FapHouse 8 months ago

Self Bondage Double Feature

Self Bondage Double Feature

Clips4sale 8 months ago

I Ruined Your Nnn

HD 1:01 / 17:37

I Ruined Your Nnn

FapHouse 8 months ago

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

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

PornBox 7 months ago

Self-training No. 48: Tackle-ass Exposure Challenge Walk

HD 1:01 / 48:29

Self-training No. 48: Tackle-ass Exposure Challenge Walk

FapHouse 9 months ago

Part 3 of a Live Stream, Sean More Camming Online. Double Penetration, From the Same Session & Getting DP for the First Time!

HD 0:39 / 13:21

Part 3 of a Live Stream, Sean More Camming Online. Double Penetration, From the Same Session & Getting DP for the First Time!

FapHouse 9 months ago

Big Cock Transsexual Gives Deep Anal To Big Tits MILF

Big Cock Transsexual Gives Deep Anal To Big Tits MILF

HoneyTrans 4 years ago

Selfie Chikubim! Pinch and Show off Her Nipples on Both Sides! I Took on the Challenge.

Selfie Chikubim! Pinch and Show off Her Nipples on Both Sides! I Took on the Challenge.

FapHouse 1 month ago

Monster Dildo Challenge Depth Training

Monster Dildo Challenge Depth Training

FapHouse 1 month ago

Femboy MILF in the Ultimate Gooner Boy Challenge

Femboy MILF in the Ultimate Gooner Boy Challenge

FapHouse 6 months ago

Open Challenge (Early Access)

Premium HD 33:43

Open Challenge (Early Access)

XNXXGold 6 months ago

CD Double Cum after Gaping with Bam & Great American Challenge

CD Double Cum after Gaping with Bam & Great American Challenge

Clips4sale 5 months ago

Mark Davis and Dana Dearmond

Mark Davis and Dana Dearmond

FapHouse 7 months ago

No Nut Challenge Fail

Premium 4K 30:09

No Nut Challenge Fail

TeamSkeet 5 years ago

Self-training No. 48: Tackle-ass Exposure Challenge Walk

Self-training No. 48: Tackle-ass Exposure Challenge Walk

FapHouse 9 months ago

Sissy Squat Endurance Training in Tight Red Rope & Locked Chastity

4K 0:29 / 47:17

Sissy Squat Endurance Training in Tight Red Rope & Locked Chastity

Clips4sale 3 months ago

Fabulous Femboy Adventures

Fabulous Femboy Adventures

Clips4sale 5 months ago

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1,266 results found

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