Challenge Videos - Trans (4,859)

TGilrs CHALLENGE (round 27) - Priscilla Beckam 20 cm VS

TGilrs CHALLENGE (round 27) - Priscilla Beckam 20 cm VS

XHamster 4 years ago

Sissy Challenge

Sissy Challenge

IWantClips 4 months ago

Francis Malice Cheerleader 1h Anal Casting Part 1

Francis Malice Cheerleader 1h Anal Casting Part 1

XHamster 2 years ago

Transsexual Here We Goes The CHALLENGE FIGHT, On Ring Renata VS Bianca

Transsexual Here We Goes The CHALLENGE FIGHT, On Ring Renata VS Bianca

BeMyHole 3 years ago

Here we goes the CHALLENGE FIGHT 192, on ring Sandy VS Anna

Here we goes the CHALLENGE FIGHT 192, on ring Sandy VS Anna

XHamster 3 years ago

Busty Cheerleader Does the Splits, Gets Dick

Busty Cheerleader Does the Splits, Gets Dick

Some.Porn 2 years ago

Rafaella VS Isabel (Tgirls Extreme Challenge)

Rafaella VS Isabel (Tgirls Extreme Challenge)

BeMyHole 3 years ago

TGilrs CHALLENGE (round 02) - Gloria Voguel 22 cm VS

TGilrs CHALLENGE (round 02) - Gloria Voguel 22 cm VS

XHamster 4 years ago

Nylon Try Not To Cum Challenge

Nylon Try Not To Cum Challenge

Tranny.one 4 years ago

Twister Gone Wild: All-Gender Orgy Party - Cliff Media

Twister Gone Wild: All-Gender Orgy Party - Cliff Media

XHamster 1 year ago

TGilrs CHALLENGE (round 43) - Christal Christal 20 cm VS

TGilrs CHALLENGE (round 43) - Christal Christal 20 cm VS

XHamster 4 years 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 3 months ago

Finally all in with the ultimate challenge - Dick Rambone to the balls

Finally all in with the ultimate challenge - Dick Rambone to the balls

XHamster 4 years ago

A Slut Tries the Impossible

A Slut Tries the Impossible

XHamster 3 days ago

$Сhallenge - can you not touch the dick.\RUS$ 76% HD 3:48

Сhallenge - can you not touch the dick.\RUS

AShemaleTube 4 years ago

Blonde MILF Gets Her Wet For Agent's Cock

Blonde MILF Gets Her Wet For Agent's Cock

Some.Porn 2 years ago

Lisa Lawrence Takes Two Hung Studs in a Steamy Bareback Anal Threesome

Lisa Lawrence Takes Two Hung Studs in a Steamy Bareback Anal Threesome

BallsNBoobs 8 months ago

Holy fuck Scotty! It is fucking HUGE!

Holy fuck Scotty! It is fucking HUGE!

Some.Porn 1 week ago

Another Straight Boy in Conversion Challenge

Another Straight Boy in Conversion Challenge

Tranny.one 4 years ago

Here we goes the CHALLENGE FIGHT, on ring Marcella VS Amanda

Here we goes the CHALLENGE FIGHT, on ring Marcella VS Amanda

XHamster 3 years ago

Here we goes the CHALLENGE FIGHT 216, on ring Lanny VS Marcella

Here we goes the CHALLENGE FIGHT 216, on ring Lanny VS Marcella

XHamster 3 years ago

Olivia Jayy Ruins Donnie Rock's No Nut Challenge in Record Time

Olivia Jayy Ruins Donnie Rock's No Nut Challenge in Record Time

XHamster 4 months ago

Cock Confusion Challenge II

Cock Confusion Challenge II

Eporner 1 year ago

An Unforgettable Rack

An Unforgettable Rack

Some.Porn 2 years ago

FERNANDA 20 cm VS ROSY 23 cm - (TGIRLS CHALLENGE 141)

FERNANDA 20 cm VS ROSY 23 cm - (TGIRLS CHALLENGE 141)

XHamster 3 years ago

Shemale Porn Video TGilrs CHALLENGE - Valesca Sargentely 22 Cm

Shemale Porn Video TGilrs CHALLENGE - Valesca Sargentely 22 Cm

Tranny.one 2 years ago

Extreme Sissy Challenge in a Public Restroom Storytime (playbdsm.vip)

Extreme Sissy Challenge in a Public Restroom Storytime (playbdsm.vip)

XHamster 1 month ago

Here we goes the CHALLENGE FIGHT, on ring Rebecca VS

Here we goes the CHALLENGE FIGHT, on ring Rebecca VS

XHamster 3 years ago

Bigtits Here We Goes The CHALLENGE FIGHT 187, On Ring Victoria VS Andrea

Bigtits Here We Goes The CHALLENGE FIGHT 187, On Ring Victoria VS Andrea

BeMyHole 2 years ago

Watch this hot amateur contest the stroke challenge with a steamy solo session

Watch this hot amateur contest the stroke challenge with a steamy solo session

GayVD 8 months ago

TGilrs CHALLENGE (round 23) - Marla 25 Cm VS Daniela 20 Cm

TGilrs CHALLENGE (round 23) - Marla 25 Cm VS Daniela 20 Cm

BeMyHole 3 years ago

LESLIE 20 cm VS MILENA 15 cm - (TGIRLS CHALLENGE 157)

LESLIE 20 cm VS MILENA 15 cm - (TGIRLS CHALLENGE 157)

XHamster 3 years ago

Hot Korra Del Rio Challenges Her Hot Asshole with a Bat

Hot Korra Del Rio Challenges Her Hot Asshole with a Bat

XHamster 7 months ago

TGilrs CHALLENGE (round 37) - Raphaella Ferrari 22 cm VS

TGilrs CHALLENGE (round 37) - Raphaella Ferrari 22 cm VS

XHamster 4 years ago

Agatha Lila A Sexy And Mature Drag Queen Who Challenges Herself By Having Sex With A Black Man Until His Enormous Penis Rots Away

Agatha Lila A Sexy And Mature Drag Queen Who Challenges Herself By Having Sex With A Black Man Until His Enormous Penis Rots Away

Eporner 6 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 2 weeks ago

TGilrs CHALLENGE (round 31) - Hanna Rios 22 cm VSChrystal

TGilrs CHALLENGE (round 31) - Hanna Rios 22 cm VSChrystal

XHamster 4 years ago

Straight Boy Test (T-girls, Shlong)

Straight Boy Test (T-girls, Shlong)

Dafreeporn 5 years ago

Trap Hetero Synesthesia

Trap Hetero Synesthesia

BigTitsLust 2 years ago

This Will Blow Your Mind: Vaniity Is Back

This Will Blow Your Mind: Vaniity Is Back

XHamster 5 months ago

”TGIRLSEX XXX - Ashley & Brooklyn Challenge For Wild Fuck”

”TGIRLSEX XXX - Ashley & Brooklyn Challenge For Wild Fuck”

Fapnow 1 year ago

Here We Goes The CHALLENGE FIGHT 216, On Ring Lanny VS Marcella

Here We Goes The CHALLENGE FIGHT 216, On Ring Lanny VS Marcella

BeMyHole 2 months ago

Yua Mikami - Intense Sex With An Asian Girl

Yua Mikami - Intense Sex With An Asian Girl

Eporner 2 weeks ago

JOI challenge for gooners and addicts

JOI challenge for gooners and addicts

Eporner 1 year ago

”Insatiable Lana gets her beautiful face covered in cum”

”Insatiable Lana gets her beautiful face covered in cum”

ThePornstar 2 years ago

Femboy Trap Jerkoff Challenge

Femboy Trap Jerkoff Challenge

Eporner 3 months ago

cock confusion challenge

cock confusion challenge

Eporner 1 year ago

Asian TGirl Cum Challenge JOI - Strokes Her Trans Cock in Purple Lingerie

Asian TGirl Cum Challenge JOI - Strokes Her Trans Cock in Purple Lingerie

XHamster 5 months ago

Edging challenge

Edging challenge

Eporner 5 years ago

Cumshot from Compilation

Cumshot from Compilation

Some.Porn 1 year ago

Try Not to Cum Epic Challenge 2

Try Not to Cum Epic Challenge 2

Some.Porn 10 months ago

TGilrs CHALLENGE (round 40) - Valentina 23 cm VS Jade 25 cm

TGilrs CHALLENGE (round 40) - Valentina 23 cm VS Jade 25 cm

XHamster 4 years ago

Str8 Male Test (Transsexuals, Jock)

Str8 Male Test (Transsexuals, Jock)

FreePorn8 5 years ago

TGilrs CHALLENGE (round 41) - Chris Christal 22 cm VS Dafne

TGilrs CHALLENGE (round 41) - Chris Christal 22 cm VS Dafne

XHamster 4 years ago

Try to WATCH Full VIDEO WITHOUT LOOKING at any DICK Challenge SISSY Test

Try to WATCH Full VIDEO WITHOUT LOOKING at any DICK Challenge SISSY Test

Tranny.one 4 years ago

Sissy Quiz

45% HD 0:18 / 24:11

IWantClips 3 years ago

Multi Orgasm Challenge

Multi Orgasm Challenge

Eporner 5 years ago

No. 169: Tuck-up Pussy Exposure and Chain Installation

No. 169: Tuck-up Pussy Exposure and Chain Installation

XHamster 6 months ago

Multi Orgasm Challenge

Multi Orgasm Challenge

BeMyHole 4 years ago

Pop The Balloon Trans Edition - Reality Defiance With Shocking Eliminations

Pop The Balloon Trans Edition - Reality Defiance With Shocking Eliminations

ShemaleSin 4 months ago

Sissy Training Day 2. My Transformation Continues

Sissy Training Day 2. My Transformation Continues

XHamster 4 months ago

Cock vs Pussy Goon Challenge PMV

Cock vs Pussy Goon Challenge PMV

Clips4sale 2 months ago

Jerk Off challenge by Asian Transgirl

Jerk Off challenge by Asian Transgirl

Eporner 1 year ago

King Noire's trans balloon challenge features shocking dating eliminations

King Noire's trans balloon challenge features shocking dating eliminations

WeGotDicks 3 months ago

Here we goes the CHALLENGE FIGHT, on ring Keylla VS Linda

Here we goes the CHALLENGE FIGHT, on ring Keylla VS Linda

XHamster 3 years ago

Here We Goes The CHALLENGE FIGHT, On Ring Principessa Vs

Here We Goes The CHALLENGE FIGHT, On Ring Principessa Vs

BeMyHole 3 years ago

Fist only CUM challenge

Fist only CUM challenge

Sheshaft 2 months ago

Here We Goes The CHALLENGE FIGHT 219, On Ring Isabelli VS Luana

Here We Goes The CHALLENGE FIGHT 219, On Ring Isabelli VS Luana

BeMyHole 3 years ago

Not Quite Straight Vol. 2 PMV Challenge

Not Quite Straight Vol. 2 PMV Challenge

Eporner 3 years ago

Turkish TS Melis - Hallway Catwalk Challenge & Fucks 2 Customers with 9" Cock

Turkish TS Melis - Hallway Catwalk Challenge & Fucks 2 Customers with 9" Cock

AShemaleTube 5 years ago

TGilrs CHALLENGE (round 50) - Luna Marks 22 cm VS Kiara 20

TGilrs CHALLENGE (round 50) - Luna Marks 22 cm VS Kiara 20

XHamster 4 years 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 9 months ago

Hentai NNN Challenge Day 13: Fairy Brothel (Ishuzoku Reviewers)

Hentai NNN Challenge Day 13: Fairy Brothel (Ishuzoku Reviewers)

Itsrealamateurs 1 month ago

Challenging My Neighbors- Cum Rain Piss

Challenging My Neighbors- Cum Rain Piss

GetTranny 3 years ago

Hankeys Toys Tryouts - L Big Daddy

Hankeys Toys Tryouts - L Big Daddy

XHamster 1 year ago

The Howard Stern Display, Finest Transgirl challenge part two

The Howard Stern Display, Finest Transgirl challenge part two

KeekAss 6 years ago

Femboy MILF in the Ultimate Gooner Boy Challenge

Femboy MILF in the Ultimate Gooner Boy Challenge

XHamster 5 months ago

TGilrs CHALLENGE (round 10) - Tiffany Kawasaky 23 cm VS

TGilrs CHALLENGE (round 10) - Tiffany Kawasaky 23 cm VS

XHamster 4 years ago

Big Load Bianca VS Bellatrix (Tgirls Extreme Challenge)

Big Load Bianca VS Bellatrix (Tgirls Extreme Challenge)

BeMyHole 4 years ago

Fucked Here We Goes The CHALLENGE FIGHT 199, On Ring Beatrice VS Renata

Fucked Here We Goes The CHALLENGE FIGHT 199, On Ring Beatrice VS Renata

BeMyHole 3 years ago

Big Tits Latina Teen Loves Hardcore Fucking and Hair Pulling

Big Tits Latina Teen Loves Hardcore Fucking and Hair Pulling

Fapcat 2 years ago

Asian TGirl Cum Challenge JOI - Strokes Her Trans Cock in Purple Lingerie

Asian TGirl Cum Challenge JOI - Strokes Her Trans Cock in Purple Lingerie

Eporner 5 months ago

Raissa 23 Cm Vs Sabrina 22 Cm Challenge 126)

Raissa 23 Cm Vs Sabrina 22 Cm Challenge 126)

AbTranny 3 years ago

30 Days to Become a Barbie - Sissy Transformation

58% HD 0:24 / 12:54

30 Days to Become a Barbie - Sissy Transformation

Clips4sale 3 months ago

Dont Cum, Sissy! - Sissy Futa Captions Challenge - Futamaxxing

Dont Cum, Sissy! - Sissy Futa Captions Challenge - Futamaxxing

Eporner 4 months ago

”Jade Venus, Olivia Jay & Little Puck Compete to Please Her in a Thrilling Showdown”

”Jade Venus, Olivia Jay & Little Puck Compete to Please Her in a Thrilling Showdown”

TransHero 1 month ago

”T-girl Khloe Kay endures three big cocks simultaneously drilling her booty an”

”T-girl Khloe Kay endures three big cocks simultaneously drilling her booty an”

429Men 9 months ago

Try no to cum Challenge ! Futanari Edition (Hentai Fap Challenge)

Try no to cum Challenge ! Futanari Edition (Hentai Fap Challenge)

AllPornHere 3 weeks ago

CAMILLA 20 cm VS JOLIE 25 cm - (TGIRLS CHALLENGE 129)

CAMILLA 20 cm VS JOLIE 25 cm - (TGIRLS CHALLENGE 129)

XHamster 3 years ago

TRANNY CUM COMPILATION ENDURANCE DEFIANCE - Can u make it to the end ?

TRANNY CUM COMPILATION ENDURANCE DEFIANCE - Can u make it to the end ?

ShemaleSin 3 years ago

Cute Femboy with Big Ass Makes a Jerk Off Challenge Experiment

Cute Femboy with Big Ass Makes a Jerk Off Challenge Experiment

XHamster 1 year ago

SPH /CEI Hooter Taunt

SPH /CEI Hooter Taunt

TrannyGem 2 years ago

Here we goes the CHALLENGE FIGHT, on ring Linda VS Jennifer

Here we goes the CHALLENGE FIGHT, on ring Linda VS Jennifer

XHamster 3 years ago

14 Days Sissygasm Challenge handfree only Cumshots

14 Days Sissygasm Challenge handfree only Cumshots

XHamster 2 years ago

Edging Game With Trans Hotty Leads To Massive CumShots! (Greater amount On OF)

Edging Game With Trans Hotty Leads To Massive CumShots! (Greater amount On OF)

ShemaleSin 5 months ago

FapFantastika 11

FapFantastika 11

Eporner 10 months ago

Here we goes the CHALLENGE FIGHT 212, on ring Hellen VS Milla

Here we goes the CHALLENGE FIGHT 212, on ring Hellen VS Milla

XHamster 3 years ago

Nobody would have guessed I view like this under my work clothes

Nobody would have guessed I view like this under my work clothes

Gayhub 1 year ago

TGilrs CHALLENGE (round 06) - Erika Lavigne 23 cm VS Nikolly

TGilrs CHALLENGE (round 06) - Erika Lavigne 23 cm VS Nikolly

XHamster 4 years ago

Futanari Red Claw (BAS)

Futanari Red Claw (BAS)

XHamster 3 months ago

MODERN-DAY SINS - Blonde Challenges Massive Tits Trans EX To Aggressive Bareback Anal Out Of Spite

MODERN-DAY SINS - Blonde Challenges Massive Tits Trans EX To Aggressive Bareback Anal Out Of Spite

XHamster 3 years ago

Big Load TGilrs Challenge

Big Load TGilrs Challenge

BeMyHole 4 years ago

Here we goes the CHALLENGE FIGHT, on ring Allana Vs Vallesca

Here we goes the CHALLENGE FIGHT, on ring Allana Vs Vallesca

XHamster 3 years ago

HOW LONG CAN YOU RESIST? SPEED HANDJOB CHALLENGE AS FAST AS POSSIBLE WITH VIVA ATHENA

HOW LONG CAN YOU RESIST? SPEED HANDJOB CHALLENGE AS FAST AS POSSIBLE WITH VIVA ATHENA

XVideos 7 years ago

Hot PinkNymph's GF edges her massive cock until it explodes with pleasure

Hot PinkNymph's GF edges her massive cock until it explodes with pleasure

TrannyMovs 1 year ago

fart challenge two girls pvc leggings big ass and bloated belly

54% HD 0:25 / 17:31

fart challenge two girls pvc leggings big ass and bloated belly

PornBox 1 month ago

Vanniall two HOUR two JIZM SHOT Edging Web cam Flash - Huge Trans Shaft Solo Jizm Shots - Fap Off Together

Vanniall two HOUR two JIZM SHOT Edging Web cam Flash - Huge Trans Shaft Solo Jizm Shots - Fap Off Together

TransTube.tv 1 year ago

95mm Huge dildo first challenge Clip 1

95mm Huge dildo first challenge Clip 1

XHamster 1 month ago

Femboy Trap Jerkoff Challenge

Femboy Trap Jerkoff Challenge

AShemaleTube 3 months ago

Shemale Dolls Put to Test

Shemale Dolls Put to Test

FapHouse 2 days ago

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

61% 1:01 / 6:37

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

FapHouse 4 months ago

No Nut November Challenge

65% HD 1:01 / 16:04

No Nut November Challenge

FapHouse 2 years ago

Shemale Porn Video Bigtits Here We Goes The CHALLENGE FIGHT 208, On Ring Flavia VS Mireja

Shemale Porn Video Bigtits Here We Goes The CHALLENGE FIGHT 208, On Ring Flavia VS Mireja

Tranny.one 2 years ago

Transexual anal challenge - Episode #10

Transexual anal challenge - Episode #10

XHamster 2 years ago

Thicc Thighs Seal This Pumpkin's Fate!

Thicc Thighs Seal This Pumpkin's Fate!

XHamster 1 week ago

You can all tap my ass, IF you win!

You can all tap my ass, IF you win!

Some.Porn 1 year ago

Dads On Set Part 2: Pick Up Lines Lead To Val's Pussy

Dads On Set Part 2: Pick Up Lines Lead To Val's Pussy

Some.Porn 1 week ago

Natally VS Arianna (Tgirls Extreme Challenge)

Natally VS Arianna (Tgirls Extreme Challenge)

BeMyHole 3 years 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 3 months ago

Chris Caught By Her Trans Foster Sister Alex While Masturbating With 6 Inch Sex-toy

Chris Caught By Her Trans Foster Sister Alex While Masturbating With 6 Inch Sex-toy

Dafreeporn 1 week ago

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