Challenge Videos - Trans (669)

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

C4S 2 years ago

Pool Hall Hustle

69% HD 0:39 / 5:36

Pool Hall Hustle

FapHouse 3 years ago

Anubet's Femdomination Wrestling 2

Anubet's Femdomination Wrestling 2

Clips4sale 1 year ago

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

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

FapHouse 1 year ago

Transsexual Anal Challenge in Brazil - Episode #10

Transsexual Anal Challenge in Brazil - Episode #10

FapHouse 1 year ago

Challenge to a new huge dildo -Part 5

HD 0:39 / 19:53

Challenge to a new huge dildo -Part 5

FapHouse 3 years ago

Transsexual Anal Challenge in Brazil - Episode #02

HD 0:39 / 19:36

Transsexual Anal Challenge in Brazil - Episode #02

FapHouse 4 years ago

Transexual anal challenge - Episode #06

Transexual anal challenge - Episode #06

FapHouse 4 years ago

Challenge to a new huge dildo -Part 2

HD 0:39 / 16:59

Challenge to a new huge dildo -Part 2

FapHouse 3 years 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 1 year ago

Sissy Test

HD 0:10 / 24:43

LoyalFans 1 year ago

30 minutes on the elliptical while getting vibed with a remote controlled butt plug challenge

HD 0:28 / 28:15

30 minutes on the elliptical while getting vibed with a remote controlled butt plug challenge

PornBox 1 year 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 1 year 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 1 year ago

Futa fuck wrestling: Paige Fujiwara vs Petra Mizzurna HD

Futa fuck wrestling: Paige Fujiwara vs Petra Mizzurna HD

Clips4sale 1 year ago

24 Hours with My Fuck Machine: Can I Handle It?

HD 0:39 / 20:18

24 Hours with My Fuck Machine: Can I Handle It?

FapHouse 11 months ago

LP-53 Golden Chicken VS Hanzvanderkill

LP-53 Golden Chicken VS Hanzvanderkill

LoyalFans 1 year ago

Wedgie wrestling-4K

Premium 4K 8:48

Wedgie wrestling-4K

Clips4sale 1 year ago

Crossdresser vibed and made to cum 720p

HD 0:22 / 11:25

Crossdresser vibed and made to cum 720p

Clips4sale 4 months ago

Week 6: A slutty task for my sissy boys (MP4)

Week 6: A slutty task for my sissy boys (MP4)

Clips4sale 2 years ago

Hellish Aroma Trapdoor

66% 0:41 / 9:03

Hellish Aroma Trapdoor

Clips4sale 3 months ago

Sissy Task for Sissies

Sissy Task for Sissies

LoyalFans 1 year ago

The Curtain Is Now Open

The Curtain Is Now Open

FapHouse 1 year ago

No More Masculinity

HD 0:10 / 11:11

No More Masculinity

LoyalFans 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 10 months 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 5 months 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 6 months 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!

XVideosRed 6 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 5 months ago

Transexual anal challenge - Episode #10

Transexual anal challenge - Episode #10

FapHouse 4 years ago

Transsexual anal challenge in Brazil - Episode #17

Transsexual anal challenge in Brazil - Episode #17

FapHouse 1 year ago

" Juicing Game"CD Fake Girl's ejaculation challenge(Chinese model)

" Juicing Game"CD Fake Girl's ejaculation challenge(Chinese model)

Clips4sale 2 years ago

Secret Sissy Winter Challenge

Secret Sissy Winter Challenge

LoyalFans 1 year 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 7 years ago

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

HD 0:39 / 13:36

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

FapHouse 7 years ago

Girlfriend isn't Just Stronger Than You- Her Dick is Bigger Too! (ID #1832 720rez)

59% 0:11 / 10:06

Girlfriend isn't Just Stronger Than You- Her Dick is Bigger Too! (ID #1832 720rez)

Clips4sale 2 years ago

Jerk Off Encouragement In Silky Panties

Jerk Off Encouragement In Silky Panties

LoyalFans 2 years ago

LOCKTOBER Challenge

LOCKTOBER Challenge

APClips 10 months ago

Streamer Fail

HD 0:10 / 10:08

LoyalFans 9 months ago

Secretdreamsfuta Intense Ride: Curvy Beauty Takes on Massive Challenge with Passion

Secretdreamsfuta Intense Ride: Curvy Beauty Takes on Massive Challenge with Passion

FapHouse 7 months ago

Futanari Milk Challenge 1

Premium HD 5:04

Futanari Milk Challenge 1

XVideosRed 7 months ago

TGilrs CHALLENGE “FIGHT 8”, on ring Debora V. Vs Tiffany

Premium HD 41:33

TGilrs CHALLENGE “FIGHT 8”, on ring Debora V. Vs Tiffany

Sheer 3 years ago

TGilrs CHALLENGE “FIGHT 14”, on ring Fernanda V. Vs Priscilla B.

Premium HD 40:55

TGilrs CHALLENGE “FIGHT 14”, on ring Fernanda V. Vs Priscilla B.

Sheer 3 years ago

Stuffing Challenge - Hamburgers, Corn, Tea, and Ice Cream

Stuffing Challenge - Hamburgers, Corn, Tea, and Ice Cream

C4S 8 months ago

TGilrs CHALLENGE “FIGHT 13”, on ring Nicolly G Vs Carolina B.

Premium HD 39:54

TGilrs CHALLENGE “FIGHT 13”, on ring Nicolly G Vs Carolina B.

Sheer 3 years ago

Mel Fire and TS Frantiesca guide you when and how to have the best orgasm ever (engl-port)

Mel Fire and TS Frantiesca guide you when and how to have the best orgasm ever (engl-port)

Clips4sale 9 months ago

Transexual anal challenge - Episode #04

Transexual anal challenge - Episode #04

FapHouse 4 years ago

Challenge inserting long dildo

Challenge inserting long dildo

FapHouse 4 years ago

Transsexual Anal Challenge in Brazil - Episode #17

HD 0:39 / 25:21

Transsexual Anal Challenge in Brazil - Episode #17

FapHouse 4 years 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

Shemale cock to cock wrestle and sexfight HD

Shemale cock to cock wrestle and sexfight HD

Clips4sale 1 year ago

combination challenge part 3 (old skool)

HD 0:10 / 12:23

combination challenge part 3 (old skool)

LoyalFans 1 year ago

He Said He Will Challenge Those Who Want to Challenge

He Said He Will Challenge Those Who Want to Challenge

FapHouse 1 year 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

Outlaw in: Maid Outfit Escape Challenge 720p

HD 0:30 / 14:29

Outlaw in: Maid Outfit Escape Challenge 720p

Clips4sale 10 months ago

Pov Boxing - Lissa

Pov Boxing - Lissa

GF Is Better Than You At Everything Masculine, Even Fucking! (ID # 1822 HD 1080rez)

GF Is Better Than You At Everything Masculine, Even Fucking! (ID # 1822 HD 1080rez)

Clips4sale 11 months ago

Latex Sissy Anal Training

HD 0:39 / 14:02

Latex Sissy Anal Training

FapHouse 2 years ago

So You're an Exhibitionist huh?! wmv

HD 0:27 / 10:50

So You're an Exhibitionist huh?! wmv

Clips4sale 2 years ago

7 Ladyboys Cum Contest

7 Ladyboys Cum Contest

FapHouse 2 years ago

Trans Punk Noctella's Intro to Foot Tickling I

Trans Punk Noctella's Intro to Foot Tickling I

Clips4sale 1 year ago

Regina Twist Vs Troy Trojan

HD 0:49 / 11:27

Regina Twist Vs Troy Trojan

Clips4sale 5 months ago

TGilrs CHALLENGE “FIGHT 102”, on ring Bianca H. Vs Bruna B.

Premium HD 43:08

TGilrs CHALLENGE “FIGHT 102”, on ring Bianca H. Vs Bruna B.

Sheer 2 years ago

No Nut Challenge Fail

Premium 4K 30:09

No Nut Challenge Fail

TeamSkeet 4 years ago

Vanessa vs JC: Arm Wrestling wmv

Vanessa vs JC: Arm Wrestling wmv

Clips4sale 6 months 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 1 year ago

Hellish Aroma Trapdoor Part 4

Hellish Aroma Trapdoor Part 4

Clips4sale 3 months ago

Starting Tonight

Starting Tonight

FapHouse 2 months ago

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

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

FapHouse 2 months ago

Deep Penetration of a Slut's Ass

Deep Penetration of a Slut's Ass

FapHouse 2 months 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

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 1 year ago

Sissy Challenge

HD 0:11 / 12:47

Sissy Challenge

Clips4sale 3 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 2 years ago

Francis Malice Cheerleader 1h Anal Casting Part 1

HD 0:39 / 1:01:39

Francis Malice Cheerleader 1h Anal Casting Part 1

FapHouse 1 year ago

Crossdress cosplay Rosalina dildos and panties

Crossdress cosplay Rosalina dildos and panties

FapHouse 6 years ago

Slap and stroke JOI game B version - CBT

HD 0:10 / 10:48

Slap and stroke JOI game B version - CBT

LoyalFans 1 year ago

Cum Challenge ! Who comes first???

Cum Challenge ! Who comes first???

LoyalFans 1 year ago

Outlaw in: Maid Outfit Escape Challenge 1080p

HD 0:30 / 14:29

Outlaw in: Maid Outfit Escape Challenge 1080p

Clips4sale 10 months 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 1 year 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

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

Challenging My Neighbors - Cum Rain, Piss

HD 0:39 / 11:24

Challenging My Neighbors - Cum Rain, Piss

FapHouse 10 months 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 9 months ago

cum play with me interactive challenge joi

66% HD 0:30 / 23:48

cum play with me interactive challenge joi

AnalVids 2 years ago

Transsexual Anal Challenge in Brazil - Episode #13

HD 0:39 / 17:43

Transsexual Anal Challenge in Brazil - Episode #13

FapHouse 4 years ago

Transsexual Anal Challenge in Brazil - Episode #10

Transsexual Anal Challenge in Brazil - Episode #10

FapHouse 4 years ago

Transsexual Anal Challenge in Brazil - Episode #20

HD 0:39 / 33:27

Transsexual Anal Challenge in Brazil - Episode #20

FapHouse 4 years ago

Surrounded by shemale cock

HD 0:39 / 26:04

Surrounded by shemale cock

FapHouse 7 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

Transexual anal challenge - Episode #07

Transexual anal challenge - Episode #07

FapHouse 4 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

Vicki's JOI Orgasm Challenge!

Vicki's JOI Orgasm Challenge!

FapHouse 1 year ago

Sissy Task for Sissies

57% HD 0:20 / 6:11

Sissy Task for Sissies

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

My SISSY's anal dildo training

My SISSY's anal dildo training

Clips4sale 1 year 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

Futa Wife's Growing Bulge - 720 MP4

61% HD 0:16 / 27:28

Futa Wife's Growing Bulge - 720 MP4

Clips4sale 3 years ago

Sissy Training Week 3

Sissy Training Week 3

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

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.

XVideosRed 3 years ago

futanari milk challenge 1

futanari milk challenge 1

PornBox 7 months ago

TGilrs CHALLENGE “FIGHT 21”, on ring Vallesca S. Vs Luna M.

Premium HD 40:51

TGilrs CHALLENGE “FIGHT 21”, on ring Vallesca S. Vs Luna M.

Sheer 2 years ago

TWINK WARS: Exploration of the Man Cave (an FTM Star Wars parody)

61% 0:10 / 16:47

TWINK WARS: Exploration of the Man Cave (an FTM Star Wars parody)

APClips 9 months ago

futanari milk challenge 2

futanari milk challenge 2

PornBox 7 months ago

TGilrs CHALLENGE “FIGHT 75”, on ring Fialho vs Valeria P. Vs Lara M.

Premium HD 45:38

TGilrs CHALLENGE “FIGHT 75”, on ring Fialho vs Valeria P. Vs Lara M.

Sheer 2 years ago

TGilrs CHALLENGE “FIGHT 9”, on ring Luana Vs Barbara

Premium HD 39:30

TGilrs CHALLENGE “FIGHT 9”, on ring Luana Vs Barbara

Sheer 3 years ago

Futanari Milk Challenge 3

Premium HD 6:03

Futanari Milk Challenge 3

xnxxGold 7 months 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

combination challenge part 1 (old skool)

combination challenge part 1 (old skool)

LoyalFans 1 year ago

pale beauty memphi hart loves bbc bareback

HD 0:30 / 26:54

pale beauty memphi hart loves bbc bareback

AnalVids 1 year ago

Fido Futa

Clips4sale 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 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

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

Sissy Katja is no longer an anal virgin!

Sissy Katja is no longer an anal virgin!

Clips4sale 2 years ago

Got Punished by 10 Huge Men BDSM Challenge

Got Punished by 10 Huge Men BDSM Challenge

FapHouse 1 year ago

Cum play with me interactive challenge JOI

Cum play with me interactive challenge JOI

xnxxGold 2 years ago

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