Challenge Videos - Trans (4,331)

Dont Blow It Defiance Can - TS Jenby Doll Finish Me in Time

Dont Blow It Defiance Can - TS Jenby Doll Finish Me in Time

ShemaleSin 2 weeks ago

ANNA 24 cm VS Miss JULI 23 cm - (TGIRLS CHALLENGE 166)

ANNA 24 cm VS Miss JULI 23 cm - (TGIRLS CHALLENGE 166)

xHamster 3 years ago

[Trans] Melody of Loyalty

68% VR 1:25 / 50:21

[Trans] Melody of Loyalty

VRPorn 1 year ago

Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

Pornzona 2 weeks ago

Shy Girl Learns All About a Weird American Tradition

Shy Girl Learns All About a Weird American Tradition

Some.Porn 1 year ago

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

61% HD 0:25 / 11:21

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

IWantClips 1 year ago

onlyfans - pietra radi yasmine de castro bianca lima tgirlplayhouse transgirl orgy

onlyfans - pietra radi yasmine de castro bianca lima tgirlplayhouse transgirl orgy

TransDoe 2 years ago

JOI Secretary Trans Anal Whore

JOI Secretary Trans Anal Whore

xHamster 2 years ago

Here we goes the CHALLENGE FIGHT 183, on ring Anna VS Elen

Here we goes the CHALLENGE FIGHT 183, on ring Anna VS Elen

xHamster 3 years ago

TGilrs CHALLENGE (round 47) - Kiara 22 cm VS Keylla Marques

TGilrs CHALLENGE (round 47) - Kiara 22 cm VS Keylla Marques

xHamster 3 years ago

Kink Trans Danni Daniels Gia DiMarco Primary Evolution Quest Human TS Seduce Destroy

Kink Trans Danni Daniels Gia DiMarco Primary Evolution Quest Human TS Seduce Destroy

Eporner 1 day ago

Unveiled Desires: A Tale of Cuckold, Hotwife

Unveiled Desires: A Tale of Cuckold, Hotwife

xHamster 2 years ago

T-Girl in Rod Cell Heads Wild Wanting to Jizm // Climax Denial

T-Girl in Rod Cell Heads Wild Wanting to Jizm // Climax Denial

TrannyGem 4 years ago

Penny Peacock – Takes Smash Challenge

Penny Peacock – Takes Smash Challenge

AbTranny 4 years ago

Trans Foxxy fucks challenging the juicy mouth and ASSHOLE

Trans Foxxy fucks challenging the juicy mouth and ASSHOLE

ALOTPorn 9 months ago

Here we goes the CHALLENGE FIGHT 218, on ring Luana VS Ingrid

Here we goes the CHALLENGE FIGHT 218, on ring Luana VS Ingrid

xHamster 3 years ago

shemale dildo hero - edging challenge

shemale dildo hero - edging challenge

Tranny.one 4 years ago

Sissy Minahyde and the sweet challenge Sweets

Sissy Minahyde and the sweet challenge Sweets

aShemaleTube 1 month ago

Stefani Suspended - Stefani Special and Elise Graves - subby Stefani completely submits to the rope suspension experience!

66% 4K 0:59 / 21:05

Stefani Suspended - Stefani Special and Elise Graves - subby Stefani completely submits to the rope suspension experience!

Clips4sale 1 year ago

Sissification Lecture "Ultimate Guide to Sissy Lovemaking Playthings" Veronica Taboo invites you to Sissy Academy

Sissification Lecture "Ultimate Guide to Sissy Lovemaking Playthings" Veronica Taboo invites you to Sissy Academy

TransTube.tv 1 year ago

TGIRLSEX XXX - Ashley and Brooklyn Challenge For Wild Fuck

TGIRLSEX XXX - Ashley and Brooklyn Challenge For Wild Fuck

Fapnado 1 year ago

SISSY ANAL challenge trying to take 15 INCHES dildo in the ass!!

SISSY ANAL challenge trying to take 15 INCHES dildo in the ass!!

xHamster 3 years ago

TSSexual.com - Eva Maxim's athletic spit roast challenge

TSSexual.com - Eva Maxim's athletic spit roast challenge

UrGayPorn 2 weeks ago

Obedient Femboy Sissy is getting desperate to jizz - Day three

Obedient Femboy Sissy is getting desperate to jizz - Day three

TransTube.tv 1 year 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

Here we goes the CHALLENGE FIGHT, on ring Bianca VS

Here we goes the CHALLENGE FIGHT, on ring Bianca VS

xHamster 3 years ago

Here we goes the CHALLENGE FIGHT 222, on ring Mary VS Letizia

Here we goes the CHALLENGE FIGHT 222, on ring Mary VS Letizia

xHamster 3 years ago

Georgia Koneva - Had A Big Challenge Ahead Of Her

Georgia Koneva - Had A Big Challenge Ahead Of Her

Eporner 11 months ago

Muddy Chatting Stroke Compete - Straight, Trans or Homo

Muddy Chatting Stroke Compete - Straight, Trans or Homo

2BGay 2 years ago

It's anal time, wake up! - Eva Maxim and Jade Venus

It's anal time, wake up! - Eva Maxim and Jade Venus

Fapnado 3 years ago

Ruby Faith Spermicide Challenge

Ruby Faith Spermicide Challenge

FukXL 1 year ago

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

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

BeMyHole 2 years ago

Sissygasm Challenge Day 2 - Femboy in Chastity Riding Dildo

Sissygasm Challenge Day 2 - Femboy in Chastity Riding Dildo

Itsrealamateurs 3 weeks ago

Brazilian And Big Tits TGilrs CHALLENGE - Daniela Colucci 20 Cm VS Luana

Brazilian And Big Tits TGilrs CHALLENGE - Daniela Colucci 20 Cm VS Luana

BeMyHole 3 years ago

Tatted TS Kelly Lovely rammed shemale Cassie Cummings in the kitchen

Tatted TS Kelly Lovely rammed shemale Cassie Cummings in the kitchen

UrGayPorn 6 months ago

Erika VS Victoria (Tgirls Extreme Challenge)

Erika VS Victoria (Tgirls Extreme Challenge)

xHamster 3 years 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 11 months ago

Juliana VS Lohara (Tgirls Extreme Challenge)

Juliana VS Lohara (Tgirls Extreme Challenge)

xHamster 3 years ago

Asia Devil Mireja Vs Flavia Da Monza (ts Challenge New

Asia Devil Mireja Vs Flavia Da Monza (ts Challenge New

getTranny 3 years ago

Gamers Battle For The Butt

Gamers Battle For The Butt

Some.Porn 9 months ago

Maha the Russian Trans MILF (part 1 of 2)

63% 1:01 / 12:35

Maha the Russian Trans MILF (part 1 of 2)

FapHouse 3 weeks ago

Teacher Hex’s practical class of biology with TS student girl Sophie (1080p ENG-sub) Trans Woman - Trans Blowjob - Trans Fucking

66% HD 0:32 / 56:20

Teacher Hex’s practical class of biology with TS student girl Sophie (1080p ENG-sub) Trans Woman - Trans Blowjob - Trans Fucking

Clips4sale 1 year ago

Krissy Lynn dares her holes to welcome TS Michelle Firestones cock

Krissy Lynn dares her holes to welcome TS Michelle Firestones cock

UrGayPorn 10 months ago

Stefani Pulled and Prodded - Stefani Special and Elise Graves - Tied in an exhausting back-arching position, Stefani has her nipples, hair, neck, waist, and mouth pushing and pulling her in all directions, rendering her quite STUCK

72% HD 0:52 / 16:48

Stefani Pulled and Prodded - Stefani Special and Elise Graves - Tied in an exhausting back-arching position, Stefani has her nipples, hair, neck, waist, and mouth pushing and pulling her in all directions, rendering her quite STUCK

Clips4sale 1 year ago

Laure Raccuzo In Unknown Challenge - I Trap The Pizza Delivery Man! I Offer Him My Ass And He Gives Me A Huge Facial!

Laure Raccuzo In Unknown Challenge - I Trap The Pizza Delivery Man! I Offer Him My Ass And He Gives Me A Huge Facial!

AbTranny 3 days ago

Here we goes the CHALLENGE FIGHT, on ring Melissa VS Helly

Here we goes the CHALLENGE FIGHT, on ring Melissa VS Helly

xHamster 3 years ago

Lovely TRANSSEXUAL Challenges A Pump Her Butt Utter Of Jizz

Lovely TRANSSEXUAL Challenges A Pump Her Butt Utter Of Jizz

TrannyGem 4 weeks ago

”TS Stars : 5 Hung Latinas vs 1 Guy Raw Orgy 4k”

”TS Stars : 5 Hung Latinas vs 1 Guy Raw Orgy 4k”

TransHero 6 years ago

Brat Perversions Freaky Sissy Training POV

Brat Perversions Freaky Sissy Training POV

xHamster 2 years ago

Here we goes the CHALLENGE FIGHT 179, on ring Rebecca Vs Vivian

Here we goes the CHALLENGE FIGHT 179, on ring Rebecca Vs Vivian

xHamster 3 years ago

Slap and stroke JOI game B version - CBT

HD 0:10 / 10:48

Slap and stroke JOI game B version - CBT

LoyalFans 2 years ago

SUSANNA 25 cm VS TAMPIRES 21 cm - (TGIRLS CHALLENGE 139)

SUSANNA 25 cm VS TAMPIRES 21 cm - (TGIRLS CHALLENGE 139)

xHamster 3 years ago

Ts babe reach orgasm by jerking her stiff cock

Ts babe reach orgasm by jerking her stiff cock

FetishShrine 8 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

Hellish Aroma Trapdoor Part 2

Hellish Aroma Trapdoor Part 2

Clips4sale 9 months ago

The Howard Stern Display, Finest Transgirl challenge part two

The Howard Stern Display, Finest Transgirl challenge part two

KeekAss 5 years ago

Futa Shehulk fucks Spiderman after battle – Futa on Male

Futa Shehulk fucks Spiderman after battle – Futa on Male

xHamster 4 years ago

Big Big Boobs Gloria VS Melissa (Tgirls Extreme Challenge)

Big Big Boobs Gloria VS Melissa (Tgirls Extreme Challenge)

BeMyHole 3 years ago

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

71% 0:30 / 43:34

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

Clips4sale 1 year ago

Foreskin Covered Cum & Piss Challenge - Never Retracting

48% HD 1:01 / 6:16

Foreskin Covered Cum & Piss Challenge - Never Retracting

FapHouse 6 months ago

Anal riding with some big black and huge dildos wich fill me and pound my ass even deeper and harder

Anal riding with some big black and huge dildos wich fill me and pound my ass even deeper and harder

xHamster 4 months ago

thirty minutes no break deepthroat spitroast defiance!

thirty minutes no break deepthroat spitroast defiance!

ShemaleSin 3 years ago

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

70% HD 1:01 / 31:22

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

FapHouse 8 months ago

Giant anal dildo depth record

Giant anal dildo depth record

xHamster 1 year ago

”Fresh widow tested a tgirl shaft”

”Fresh widow tested a tgirl shaft”

HQBang 2 years ago

Fucking a fat mature lady can be very challenging especially when she is horny

Fucking a fat mature lady can be very challenging especially when she is horny

xHamster 2 years ago

Independent Training No98 Standing Machine Masturbation

Independent Training No98 Standing Machine Masturbation

xHamster 4 months ago

AB072 Crazy edging and tickling play

AB072 Crazy edging and tickling play

Fapcat 3 years ago

Super intense anal sex with TS Leah Hayes

Super intense anal sex with TS Leah Hayes

Yeswegays 2 weeks ago

Here we goes the CHALLENGE FIGHT, on ring Raissa VS Bianca

Here we goes the CHALLENGE FIGHT, on ring Raissa VS Bianca

xHamster 3 years ago

The Janitor's Naughty Break

The Janitor's Naughty Break

Slutr 5 months ago

DEVILS FILM - Wild Bisexual Threesome With Wife Adira Allure And Two Big Cocks

DEVILS FILM - Wild Bisexual Threesome With Wife Adira Allure And Two Big Cocks

Some.Porn 1 year ago

”GROOBYVR - The Fan Fuck With Lola”

”GROOBYVR - The Fan Fuck With Lola”

HQBang 1 month ago

Gamer Girl [Part 1]

4K 0:11 / 15:44

Gamer Girl [Part 1]

Clips4sale 4 years ago

TGilrs CHALLENGE (round 05) - Daniela Colucci 20 cm VS Luana

TGilrs CHALLENGE (round 05) - Daniela Colucci 20 cm VS Luana

xHamster 3 years ago

two Lesbian Cuties Sucking Tgirl Huge Rod Cumming

two Lesbian Cuties Sucking Tgirl Huge Rod Cumming

PornFreeNow 1 day ago

Here we goes the CHALLENGE FIGHT, on ring Ingrid Vs Marcella

Here we goes the CHALLENGE FIGHT, on ring Ingrid Vs Marcella

xHamster 3 years ago

Foreskin Covered Cum & Piss Challenge - Never Retracting

51% HD 0:39 / 6:16

Foreskin Covered Cum & Piss Challenge - Never Retracting

FapHouse 6 months ago

Gloria VS Melissa (Tgirls Extreme Challenge)

Gloria VS Melissa (Tgirls Extreme Challenge)

xHamster 3 years ago

This Whore Got Nailed

This Whore Got Nailed

xHamster 3 months ago

Bikers

LesbianBliss 6 months ago

Fresh widow tested a tgirl cock

Fresh widow tested a tgirl cock

Fapnado 4 years ago

TS Jessy Dubai moans with every hard thrust her BBC dom gives

TS Jessy Dubai moans with every hard thrust her BBC dom gives

Sheshaft 1 year 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

XVideosRed 1 month ago

A Dance with Curiosity Unveiling the Unknown

A Dance with Curiosity Unveiling the Unknown

xHamster 1 year ago

extreme market challenge: part 2 — huge ball limit and pumpkin for dumb sissy [3-part series]

extreme market challenge: part 2 — huge ball limit and pumpkin for dumb sissy [3-part series]

PornBox 1 week ago

Deborah VS Samara (Tgirls Extreme Challenge)

Deborah VS Samara (Tgirls Extreme Challenge)

xHamster 3 years ago

September through December 2025 Cumpilation

September through December 2025 Cumpilation

xHamster 6 months ago

Big Tits Latina Teen Loves Hardcore Fucking and Hair Pulling

Big Tits Latina Teen Loves Hardcore Fucking and Hair Pulling

Fapcat 1 year ago

Sexu trans girl Krystall Cox in pink fishnets riding a huge dildo

Sexu trans girl Krystall Cox in pink fishnets riding a huge dildo

xHamster 2 years ago

Kiss The Ball

xHamster 3 months ago

DEVILS TGIRLS - Hot Trans Olivia Accepts Booty Call From Her Friend Ana Foxxx

DEVILS TGIRLS - Hot Trans Olivia Accepts Booty Call From Her Friend Ana Foxxx

Some.Porn 2 months ago

wichsanleitung an tgirl wendy für dich ich zeig dir wie dude wichst! sexdoll realistic doll

wichsanleitung an tgirl wendy für dich ich zeig dir wie dude wichst! sexdoll realistic doll

Lesbian8 7 months ago

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

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

BeMyHole 2 years ago

Cursed Desires: Boy-Girl Transformation

59% 0:16 / 9:35

Cursed Desires: Boy-Girl Transformation

Clips4sale 2 years ago

ADULT TIME Sexy T Chick Izzy Wilde Challenges Her GF Cam

ADULT TIME Sexy T Chick Izzy Wilde Challenges Her GF Cam

Sheshaft 3 days ago

”Katy Leon - Monstercocking Katy Leon - Tranny Porn”

”Katy Leon - Monstercocking Katy Leon - Tranny Porn”

TransHero 3 years ago

Rope Tied Oil Catfight and Trib Fight

61% 0:30 / 10:08

Rope Tied Oil Catfight and Trib Fight

Clips4sale 1 year ago

Kink Trans Top Chef Jessica Host Kurt Connors TS Cock Challenge Anal Fuck Academy

Kink Trans Top Chef Jessica Host Kurt Connors TS Cock Challenge Anal Fuck Academy

aShemaleTube 1 week ago

Edging your hard dong until cum - Countdown

Edging your hard dong until cum - Countdown

ShemaleSin 4 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

FTM transman's double holes penetration stuffing dildos for intense orgasm

HD 1:01 / 13:51

FTM transman's double holes penetration stuffing dildos for intense orgasm

FapHouse 7 years ago

Here we goes the CHALLENGE FIGHT, on ring Alessandra VS

Here we goes the CHALLENGE FIGHT, on ring Alessandra VS

xHamster 3 years ago

Super intense anal sex with TS Leah Hayes

Super intense anal sex with TS Leah Hayes

Sheshaft 3 weeks ago

I need big cock to my pussy I am so hot

I need big cock to my pussy I am so hot

Pornzona 2 weeks ago

Transexual anal challenge - Episode #10

Transexual anal challenge - Episode #10

xHamster 2 years ago

Front view challenge with Dick Rambone - This dildo is kinda long enough Clip 1

Front view challenge with Dick Rambone - This dildo is kinda long enough Clip 1

xHamster 9 months ago

Here we goes the CHALLENGE FIGHT 189, on ring Andrea VS Vanity

Here we goes the CHALLENGE FIGHT 189, on ring Andrea VS Vanity

xHamster 3 years ago

Tgilrs Challenge (round 44) - Jade 24 Cm Vs Renata Molina 23

Tgilrs Challenge (round 44) - Jade 24 Cm Vs Renata Molina 23

getTranny 3 years ago

Spitroasted in wondrous underwear by two big fake-jizz-shotguns

Spitroasted in wondrous underwear by two big fake-jizz-shotguns

TransTube.tv 1 year ago

Big Dick Trans Domme Stroke-for-stroke Masturbation Challenge 10-minutes With Explosive Finish

Big Dick Trans Domme Stroke-for-stroke Masturbation Challenge 10-minutes With Explosive Finish

AbTranny 1 week ago

3 HOUR TRY NOT TO CUM EDGING CHALLENGE FULL MOVIE

3 HOUR TRY NOT TO CUM EDGING CHALLENGE FULL MOVIE

Itsrealamateurs 3 weeks ago

JUDE LYNX — SEDUCING AND FUCKING HARD HIS BIG CLIT FTM INSIDE THE PANTIES

JUDE LYNX — SEDUCING AND FUCKING HARD HIS BIG CLIT FTM INSIDE THE PANTIES

Pornzona 2 days 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 3 months ago

Tgilrs Challenge (round 35) - Veronica Havenna 24 Cm Vs - Teaser Video

Tgilrs Challenge (round 35) - Veronica Havenna 24 Cm Vs - Teaser Video

getTranny 3 years ago

Secretary Caught Shemale Boss Fucking Sexy Girl In Office

Secretary Caught Shemale Boss Fucking Sexy Girl In Office

xHamster 5 days ago

Real Gamers Only Pause For Cock

Real Gamers Only Pause For Cock

Some.Porn 1 year ago

Ariadny Oliver Vs Sabrina Vienna (ts Challenge New Edition)

Ariadny Oliver Vs Sabrina Vienna (ts Challenge New Edition)

getTranny 3 years ago

”BLACK TGIRLS - The Japanese Kitten Unleashed”

”BLACK TGIRLS - The Japanese Kitten Unleashed”

LesbianBliss 5 months ago

ABT250116 20cm Dildo Challenge Clip 1

ABT250116 20cm Dildo Challenge Clip 1

xHamster 2 months ago

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