Challenge Videos - Trans (1,303)

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

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

FapHouse 8 months ago

Foreskin Covered Cum & Piss Challenge - Never Retracting

51% HD 0:39 / 6:16

Foreskin Covered Cum & Piss Challenge - Never Retracting

FapHouse 10 months ago

Let's See How Good You Are, My Little Wanker! Now You Have to Cum Twice! German - Wichsanleitung

47% HD 1:01 / 6:52

Let's See How Good You Are, My Little Wanker! Now You Have to Cum Twice! German - Wichsanleitung

FapHouse 8 months ago

sissy anal endurance test: holding massive dildo deep inside until full gape / intense slow anal stretch: sissy accommodation challenge with thick toy

63% 0:21 / 7:00

sissy anal endurance test: holding massive dildo deep inside until full gape / intense slow anal stretch: sissy accommodation challenge with thick toy

AnalVids 5 days ago

Cock vs Pussy Goon Challenge PMV

Cock vs Pussy Goon Challenge PMV

Clips4sale 1 month ago

The Stepsister’s Unexpected Discovery

65% 0:30 / 32:49

The Stepsister’s Unexpected Discovery

Clips 2 weeks ago

30 Days to Become a Barbie - Sissy Transformation

60% HD 0:24 / 12:54

30 Days to Become a Barbie - Sissy Transformation

Clips4sale 2 months ago

Cum Challenge! Who Comes First???

69% HD 0:39 / 4:12

Cum Challenge! Who Comes First???

FapHouse 2 years ago

Sissy Quiz

45% HD 0:18 / 24:11

IWantClips 3 years ago

Sweaty Dirty Creamy Black Panty Cardio

HD 1:01 / 47:13

Sweaty Dirty Creamy Black Panty Cardio

FapHouse 1 year ago

Eva Turned a Top Guy Into a Bottom

60% HD 1:01 / 16:41

Eva Turned a Top Guy Into a Bottom

FapHouse 7 months ago

Feminized by the Chef: A Locktober Tale

45% 4K 0:30 / 35:05

Feminized by the Chef: A Locktober Tale

Clips4sale 2 years ago

Maha the Russian Trans MILF (part 1 of 2)

53% 0:39 / 12:35

Maha the Russian Trans MILF (part 1 of 2)

FapHouse 4 months ago

Pool Hall Hustle

65% HD 1:01 / 5:41

Pool Hall Hustle

FapHouse 4 years ago

Pounded by Tammy10Inch & left a TS Cock-Craving Mess

45% HD 0:10 / 43:48

Pounded by Tammy10Inch & left a TS Cock-Craving Mess

LoyalFans 2 months ago

Cheating women fucking with strangers for their own pleasure. Sally Torres is up to the challenge: Banging Cris while calling her boyfriend

63% HD 2:38 / 58:40

Cheating women fucking with strangers for their own pleasure. Sally Torres is up to the challenge: Banging Cris while calling her boyfriend

FaKings 1 year ago

Restrained Orgasm Challenge

65% HD 0:11 / 27:40

Restrained Orgasm Challenge

Clips4sale 3 years ago

Punished JOI POV - Hands free climax challenge

66% 0:30 / 18:06

Punished JOI POV - Hands free climax challenge

Clips4sale 1 year ago

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

64% 1:01 / 6:37

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

FapHouse 3 months ago

Flashing in a Busy Carpark

68% HD 1:01 / 6:28

Flashing in a Busy Carpark

FapHouse 2 years ago

Post Orgasm Cum Milking Jessica Bloom Big Trans Dick Milking Machine

71% HD 1:01 / 24:34

Post Orgasm Cum Milking Jessica Bloom Big Trans Dick Milking Machine

FapHouse 2 years ago

Cum in Panties CEI JOI- Cum Eating Instructions by Goddess Nikki Kit

66% HD 0:25 / 11:21

Cum in Panties CEI JOI- Cum Eating Instructions by Goddess Nikki Kit

IWantClips 2 years ago

Sissy Task for Sissies

57% HD 0:20 / 6:11

Sissy Task for Sissies

Clips4sale 2 years ago

She Noticed Me Touching Myself and Didn’t Stop Me

72% 0:39 / 21:30

She Noticed Me Touching Myself and Didn’t Stop Me

FapHouse 2 months ago

Set of Pool Balls Inserted & Pulled Out by Valentinarosa89 Stretch

72% HD 1:01 / 9:03

Set of Pool Balls Inserted & Pulled Out by Valentinarosa89 Stretch

FapHouse 1 year ago

fart challenge two girls pvc leggings big ass and bloated belly

HD 0:25 / 17:31

fart challenge two girls pvc leggings big ass and bloated belly

PornBox 3 weeks ago

Letting 30 Gel Balls Grow Inside My Dick Then Shooting Them Out with Loads of Cum

HD 1:01 / 45:50

Letting 30 Gel Balls Grow Inside My Dick Then Shooting Them Out with Loads of Cum

FapHouse 5 days ago

Pounded by Tammy 10 Inches & left a TS Cock-Craving Mess

Premium 4K 43:48

Pounded by Tammy 10 Inches & left a TS Cock-Craving Mess

Clips4sale 2 months ago

Stunning Asian Trans Babe Teacher Praew Loves Foreign Cock

64% HD 1:01 / 27:04

Stunning Asian Trans Babe Teacher Praew Loves Foreign Cock

FapHouse 8 months ago

Boss Roberta Cortes demands sex from job applicant Hex - PT 02 (1080p English)

57% HD 0:28 / 15:23

Boss Roberta Cortes demands sex from job applicant Hex - PT 02 (1080p English)

Clips4sale 1 year ago

Let's See How Good You Are, My Little Wanker! Now You Have to Cum Twice! German - Wichsanleitung

63% HD 0:39 / 6:52

Let's See How Good You Are, My Little Wanker! Now You Have to Cum Twice! German - Wichsanleitung

FapHouse 8 months ago

Group Sex with a Shemale and the Guy Is Fucking Me

53% HD 0:39 / 9:41

Group Sex with a Shemale and the Guy Is Fucking Me

FapHouse 5 months ago

Arm Strength Challenge

Arm Strength Challenge

FapHouse 1 year ago

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

64% HD 0:10 / 43:34

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

LoyalFans 1 year ago

The Tight Hole of the Banana Tree Is Delicious

61% HD 0:39 / 6:05

The Tight Hole of the Banana Tree Is Delicious

FapHouse 1 year ago

INNER DEMONS

4K 0:30 / 27:58

Clips4sale 3 weeks ago

Discode 1

52% HD 0:39 / 20:13

FapHouse 6 months ago

30 Days to Become a Barbie - Sissy Transformation - sissy training - sissy slut - femdom pov - encouraged bi - crossdresser - cock worship - MTF

46% HD 0:10 / 12:55

30 Days to Become a Barbie - Sissy Transformation - sissy training - sissy slut - femdom pov - encouraged bi - crossdresser - cock worship - MTF

LoyalFans 2 months ago

Black Silk Pantyhose Escape Challenge! Sissy in Tight White Rope Frog Tie Struggles for Scissors & Milking!

Premium 4K 53:40

Black Silk Pantyhose Escape Challenge! Sissy in Tight White Rope Frog Tie Struggles for Scissors & Milking!

Clips4sale 4 months ago

This Will Blow Your Mind: Vaniity Is Back

67% HD 1:01 / 35:43

This Will Blow Your Mind: Vaniity Is Back

FapHouse 6 months ago

Cock Ring Challenge Hands-free Orgasm

71% 1:01 / 7:06

Cock Ring Challenge Hands-free Orgasm

FapHouse 1 week ago

She Noticed Me Touching Myself and Didn’t Stop Me

60% 1:01 / 21:30

She Noticed Me Touching Myself and Didn’t Stop Me

FapHouse 2 months ago

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

55% 0:39 / 6:37

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

FapHouse 3 months ago

Cum Challenge! Who Comes First???

61% HD 0:39 / 4:12

Cum Challenge! Who Comes First???

FapHouse 2 years ago

Presenting a Challenge

74% 1:29 / 21:46

Presenting a Challenge

QueerCrush 7 months ago

Aubrey Kate - I Am Aubrey

4K 1:00 / 37:16

Aubrey Kate - I Am Aubrey

Erotik 5 years ago

Award Winning - Neon Vampire - Evolution Scene Ii

61% 1:01 / 29:15

Award Winning - Neon Vampire - Evolution Scene Ii

FapHouse 1 year ago

Jasmine_dlight & Ava Black - Extreme Anal Footing Huge Foot Fills Me up 4th Times a Charm

HD 1:01 / 34:02

Jasmine_dlight & Ava Black - Extreme Anal Footing Huge Foot Fills Me up 4th Times a Charm

FapHouse 5 days ago

You Can Tame the Monster, Do You Accept the Challenge?

65% HD 0:39 / 2:59

You Can Tame the Monster, Do You Accept the Challenge?

FapHouse 1 month ago

Cock Ring Challenge Hands-free Orgasm

Cock Ring Challenge Hands-free Orgasm

FapHouse 1 week ago

For her, a MASSIVE DONG, for him HUGE TITS AND ASS... but what if they are the same person's? 1st SHEMALE EXPERIENCE: ¡DALMITA RETURNS!

57% HD 3:06 / 51:56

For her, a MASSIVE DONG, for him HUGE TITS AND ASS... but what if they are the same person's? 1st SHEMALE EXPERIENCE: ¡DALMITA RETURNS!

FaKings 7 years ago

Liquid Silicone Encasement Bondage

HD 1:01 / 1:01:39

Liquid Silicone Encasement Bondage

FapHouse 1 month ago

Hot Sissy Extreme 16cm High Heel Shoe Removal Challenge + Milking

66% 4K 0:27 / 1:12:41

Hot Sissy Extreme 16cm High Heel Shoe Removal Challenge + Milking

Clips4sale 3 months ago

Fisting for Nutt: Bee Masterfully Fists Her Ass to Orgasm

Fisting for Nutt: Bee Masterfully Fists Her Ass to Orgasm

FapHouse 1 month ago

Aubrey Kate - I Am Aubrey

Aubrey Kate - I Am Aubrey

Erotik 5 years ago

Eva Turned a Top Guy Into a Bottom

74% HD 0:39 / 16:41

Eva Turned a Top Guy Into a Bottom

FapHouse 7 months ago

30 years of difference. Gerontophilia in porn videos. But doesn't anyone here watch FAKings? Victoria Arias vs. Don Jorge

64% HD 3:33 / 47:51

30 years of difference. Gerontophilia in porn videos. But doesn't anyone here watch FAKings? Victoria Arias vs. Don Jorge

FaKings 1 year ago

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

Premium HD 25:11

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

Sheer 8 months ago

Post Orgasm Cum Milking Jessica Bloom Big Trans Dick Milking Machine

HD 0:39 / 24:34

Post Orgasm Cum Milking Jessica Bloom Big Trans Dick Milking Machine

FapHouse 2 years ago

Foreskin Covered Cum & Piss Challenge - Never Retracting

48% HD 1:01 / 6:16

Foreskin Covered Cum & Piss Challenge - Never Retracting

FapHouse 10 months ago

TS Ria Bentley Fucks TS Gray Perrier in Every Room of Her House!

70% HD 0:39 / 31:22

TS Ria Bentley Fucks TS Gray Perrier in Every Room of Her House!

FapHouse 1 year 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 8 months ago

Lesbian Fart Challenge Who Farts More with Face Farts and Ass Sniffing 4K

Premium 4K 15:45

Lesbian Fart Challenge Who Farts More with Face Farts and Ass Sniffing 4K

Sheer 5 months ago

I might’ve met my match

59% HD 0:10 / 21:19

I might’ve met my match

LoyalFans 5 months ago

Fisting for Nutt: Bee Masterfully Fists Her Ass to Orgasm

61% HD 1:01 / 6:08

Fisting for Nutt: Bee Masterfully Fists Her Ass to Orgasm

FapHouse 1 month ago

Desperate Ftm Edging Handcuffed

HD 1:01 / 49:09

Desperate Ftm Edging Handcuffed

FapHouse 1 day ago

Cum Challenge ! Who comes first???

69% HD 0:10 / 4:07

Cum Challenge ! Who comes first???

LoyalFans 2 years ago

Fart Challenge Two Girls PVC Leggings Big ass and Bloated Belly

Premium HD 17:31

Fart Challenge Two Girls PVC Leggings Big ass and Bloated Belly

Sheer 3 weeks ago

Rescued Tiny's Reward: Thanking a Friendly FtM Giant by Worshipping His Pussy and Clit - POV - Jaq Quicksilver - 4k mp4

63% 4K 0:27 / 10:57

Rescued Tiny's Reward: Thanking a Friendly FtM Giant by Worshipping His Pussy and Clit - POV - Jaq Quicksilver - 4k mp4

Clips4sale 1 year ago

Sex Addiction

56% 4K 1:00 / 59:12

Futanari 1 year ago

Stunning Asian Trans Babe Teacher Praew Loves Foreign Cock

63% HD 0:39 / 27:04

Stunning Asian Trans Babe Teacher Praew Loves Foreign Cock

FapHouse 8 months 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

Sheer 6 days ago

Wanking Machine Challenge T-girl v machine

58% HD 0:10 / 13:33

Wanking Machine Challenge T-girl v machine

LoyalFans 5 years ago

I want my MONSTERCOCK CHALLENGE too, I'm Alexia and I love giant dicks

51% HD 3:06 / 43:22

I want my MONSTERCOCK CHALLENGE too, I'm Alexia and I love giant dicks

FaKings 6 years ago

Maha the Russian Trans MILF (part 2 of 2)

63% 1:01 / 12:09

Maha the Russian Trans MILF (part 2 of 2)

FapHouse 4 months ago

Pierce'd to Her Limit!

64% VR 0:39 / 27:07

Pierce'd to Her Limit!

FapHouse 1 year 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

Extreme Hogtie Punishment: Lift Your Head or Get Shocked! Drooling and Leaking in Collapse

Extreme Hogtie Punishment: Lift Your Head or Get Shocked! Drooling and Leaking in Collapse

Clips4sale 10 months ago

Dana Delvey's Epic Dragon Ride

58% HD 0:10 / 25:10

Dana Delvey's Epic Dragon Ride

LoyalFans 7 months 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 11 months ago

Ts Babi Antonella traps and blindfold Hex and have lots of fun with him (720p ENG-sub) Trans Woman - Trans Fucking - Trans Anal - Trans Domination - Trans Blowjob - Trans Ass Licking

70% HD 0:25 / 22:57

Ts Babi Antonella traps and blindfold Hex and have lots of fun with him (720p ENG-sub) Trans Woman - Trans Fucking - Trans Anal - Trans Domination - Trans Blowjob - Trans Ass Licking

Clips4sale 1 year ago

Latex Gloved Throat Exam Under Bondage: Gag Reflex Challenge

Premium HD 6:47

Latex Gloved Throat Exam Under Bondage: Gag Reflex Challenge

Clips4sale 3 months ago

Set of Pool Balls Inserted & Pulled Out by Valentinarosa89 Stretch

53% HD 0:39 / 9:03

Set of Pool Balls Inserted & Pulled Out by Valentinarosa89 Stretch

FapHouse 1 year ago

gdgdg

AdultPrime 7 months ago

Shakira Brazil's Bareback Anal Feast with Alana Duarte

61% VR 0:08 / 35:09

Shakira Brazil's Bareback Anal Feast with Alana Duarte

FapHouse 1 month ago

Car Foot Fetish

Car Foot Fetish

FapHouse 1 year ago

[Trans] Pierce'd to Her Limit!

58% VR 1:30 / 27:11

[Trans] Pierce'd to Her Limit!

VRPorn 2 years ago

[Trans] The Fan Fuck

VR 1:11 / 28:24

[Trans] The Fan Fuck

VRPorn 4 months ago

Jenby Doll – Don’t Blow It Challenge PAYOFF (She Fails… I Take Over)(11mins)

4K 0:10 / 12:31

Jenby Doll – Don’t Blow It Challenge PAYOFF (She Fails… I Take Over)(11mins)

LoyalFans 3 months ago

Mrs Nara and 4 TS uses a guy and a girl as fuck holes - Complete (1080 EN-sub)

48% 4K 0:29 / 42:03

Mrs Nara and 4 TS uses a guy and a girl as fuck holes - Complete (1080 EN-sub)

Clips4sale 3 years ago

Boss Roberta Cortes demands sex from job applicant Hex - FULL (1080p English)

51% HD 0:38 / 30:37

Boss Roberta Cortes demands sex from job applicant Hex - FULL (1080p English)

Clips4sale 1 year ago

Boss Roberta Cortes demands sex from job applicant Hex - FULL (720p English)

66% HD 0:38 / 30:37

Boss Roberta Cortes demands sex from job applicant Hex - FULL (720p English)

Clips4sale 1 year ago

brazilian bombshell luna alvier loves bbc

55% HD 0:30 / 34:09

brazilian bombshell luna alvier loves bbc

AnalVids 2 years ago

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

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

FapHouse 4 months ago

The Cum Cookie Challenge

61% 0:28 / 13:59

The Cum Cookie Challenge

Clips4sale 3 years ago

GlitterGiiiirl´s Nike Pro Leggings Check

63% HD 0:30 / 1:43

GlitterGiiiirl´s Nike Pro Leggings Check

Clips4sale 1 year ago

20 Spurts of Semen..3 Cumshots in a row!

20 Spurts of Semen..3 Cumshots in a row!

Clips4sale 9 months ago

Sissy training task September 26

55% HD 0:30 / 2:51

Sissy training task September 26

Clips4sale 3 weeks ago

Cum in Panties - CEI JOI

56% HD 0:25 / 11:21

Cum in Panties - CEI JOI

Clips4sale 2 years ago

You can have a sandwich if you fuck me

4K 0:12 / 33:36

You can have a sandwich if you fuck me

AdultPrime 2 years ago

Chastity Release Challenge by Tranny Girl! You have to cum in one minute!! GERMAN

57% HD 0:30 / 6:34

Chastity Release Challenge by Tranny Girl! You have to cum in one minute!! GERMAN

Clips4sale 3 years ago

Try Not to Cum Challenge Part X

53% HD 1:01 / 18:52

Try Not to Cum Challenge Part X

FapHouse 2 months ago

We're Still Here with the Chinese Balls. Eater-ass

44% HD 0:39 / 8:27

We're Still Here with the Chinese Balls. Eater-ass

FapHouse 9 months ago

Starting My Day in the Best Mood Can You Tell?

66% 1:01 / 6:03

Starting My Day in the Best Mood Can You Tell?

FapHouse 8 months ago

We're looking for the new 'Young Polla.' Crow, are you up for casting some new talents?

HD 3:08 / 1:26:52

We're looking for the new 'Young Polla.' Crow, are you up for casting some new talents?

FaKings 3 years ago

Busty Latina TS Angela Bratz takes down a big dick stud

70% HD 1:01 / 30:58

Busty Latina TS Angela Bratz takes down a big dick stud

FapHouse 4 years ago

Cute Maid Femboy in Extreme Suspension Shibari Torment - Frilly Outfit, Black Stockings, High Heels, Rope Hoist & Vibrator Tease During Intense Hanging Struggle

65% 0:30 / 2:04:22

Cute Maid Femboy in Extreme Suspension Shibari Torment - Frilly Outfit, Black Stockings, High Heels, Rope Hoist & Vibrator Tease During Intense Hanging Struggle

Clips4sale 9 months ago

Anal Fuck Machine Solo Pornstar Jamie French

69% HD 1:01 / 20:16

Anal Fuck Machine Solo Pornstar Jamie French

FapHouse 6 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

Blake Lovely - Extreme Deepthroat - Swallowing Rodrigo Amor's Thick 10 Inch Monster Cock Gag Challenge

Blake Lovely - Extreme Deepthroat - Swallowing Rodrigo Amor's Thick 10 Inch Monster Cock Gag Challenge

Clips4sale 7 months ago

Secret Sissy Winter Challenge

Secret Sissy Winter Challenge

LoyalFans 1 year ago

Pool Hall Hustle

69% HD 0:39 / 5:41

Pool Hall Hustle

FapHouse 4 years ago

Il contratto di Sissy - The Sissy's slut contract #2 ( PART 1) (MOBILE VERSION MP4)

44% HD 0:11 / 35:01

Il contratto di Sissy - The Sissy's slut contract #2 ( PART 1) (MOBILE VERSION MP4)

Clips4sale 2 years ago

Frankie Catalyst's Air Tight Fantasy with Countdown

HD 0:34 / 12:00

Frankie Catalyst's Air Tight Fantasy with Countdown

Clips4sale 1 month ago

I Oil Up My Trans Cock and Masturbate

I Oil Up My Trans Cock and Masturbate

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

TS Counselor Fantasy Weaver

59% 0:11 / 13:25

TS Counselor Fantasy Weaver

Clips4sale 3 years ago

ABDL Marshmallow Challenge!

HD 0:25 / 28:09

ABDL Marshmallow Challenge!

Clips4sale 1 day ago

Self-training No. 95: Wearing Sanitary Napkins and Tampons for an Exposure Walk - Part 2

HD 1:01 / 17:47

Self-training No. 95: Wearing Sanitary Napkins and Tampons for an Exposure Walk - Part 2

FapHouse 8 months ago

Chanel Santini Joins Three Studs

Chanel Santini Joins Three Studs

ShemalesTube 6 years ago

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