Contest Videos - Trans (3,600)

ADULT TIME - Sexy T-Girl Izzy Wilde Challenges Her GF Cami Strella To Sex Battle To Settle Argument!

ADULT TIME - Sexy T-Girl Izzy Wilde Challenges Her GF Cami Strella To Sex Battle To Settle Argument!

Fapcat 1 year ago

TGilrs CHALLENGE (round 22) - Valesca Sargentely 23 cm VS

TGilrs CHALLENGE (round 22) - Valesca Sargentely 23 cm VS

xHamster 3 years ago

Competitive Shemale Ballerinas Having Sex With Bio-girl Dancer - Rubi Maxim, Jenna Noelle And Natalie Mars

Competitive Shemale Ballerinas Having Sex With Bio-girl Dancer - Rubi Maxim, Jenna Noelle And Natalie Mars

PePorn 8 months ago

”TBabe Khloe Kay's Having Anal Sex At Marilyn Monroe Audition”

”TBabe Khloe Kay's Having Anal Sex At Marilyn Monroe Audition”

Rainblow 1 year ago

Hermaphroditism Milk Contest 1

Hermaphroditism Milk Contest 1

HentaiGem 8 months ago

Sissygasm Contest 14 days sans kneading it.

Sissygasm Contest 14 days sans kneading it.

TrannyGem 1 year ago

Blowjob Contest ends in Intense Orgy - See Moore in XVIDEOS RED

Blowjob Contest ends in Intense Orgy - See Moore in XVIDEOS RED

aShemaleTube 3 months ago

Kira's latest contest Is Getting bashed By A shelady And And father lad!

Kira's latest contest Is Getting bashed By A shelady And And father lad!

Transvids.tv 8 months ago

TGilrs CHALLENGE (round 20) - Veronika Havenna 25 cm VS

TGilrs CHALLENGE (round 20) - Veronika Havenna 25 cm VS

xHamster 3 years ago

Casey and Kat Take Everything Part 1

49% HD 0:12 / 14:15

Casey and Kat Take Everything Part 1

AdultPrime 6 years ago

Bokd-280 A Dream Competition! We Look Like Boys, Tsumug

Bokd-280 A Dream Competition! We Look Like Boys, Tsumug

AbTranny 2 years ago

TGilrs CONTEST (plump 12) - Debora Vasques twenty one cm VS

TGilrs CONTEST (plump 12) - Debora Vasques twenty one cm VS

KeekAss 3 years ago

”Fresh widow tested a tgirl shaft”

”Fresh widow tested a tgirl shaft”

HQBang 2 years ago

The Girls Who Loved Cock Fighting wmv

49% HD 0:30 / 5:56

The Girls Who Loved Cock Fighting wmv

Clips4sale 1 year ago

Behind the Scenes Porn: Trans Vs. Woman

62% HD 1:01 / 9:12

Behind the Scenes Porn: Trans Vs. Woman

FapHouse 1 year ago

”These powersluts needs a real sword to play with - VIXEN”

”These powersluts needs a real sword to play with - VIXEN”

ThePornstar 1 year ago

”Fresh widow tested a tgirl prick”

”Fresh widow tested a tgirl prick”

TransHero 4 years ago

Wrestling amateur lez facesits loser after match

Wrestling amateur lez facesits loser after match

Some.Porn 2 years ago

Excellent snatch for trannies

Excellent snatch for trannies

4Gay 10 months ago

Chastity Sissy Marissa Nicole Wins a Free Bondage Lesson!

Chastity Sissy Marissa Nicole Wins a Free Bondage Lesson!

Clips4sale 8 months ago

Interracial Wife Swap Foursome With Shemales Bianca Meirelles and India Taina DT729

Premium HD 46:37

Interracial Wife Swap Foursome With Shemales Bianca Meirelles and India Taina DT729

Sheer 4 years ago

Hot Cassidy Quinn has big tits fucking contest with tranny

Hot Cassidy Quinn has big tits fucking contest with tranny

BeMyHole 5 years ago

HotHouse: Thick coach wants gagging

HotHouse: Thick coach wants gagging

GayTube.site 4 years ago

”Kendra Spade & Maria Jade deepthroating”

”Kendra Spade & Maria Jade deepthroating”

TransHero 6 months ago

Female Body Building Competition Stalker Ass Fucked For Being Creepy

Female Body Building Competition Stalker Ass Fucked For Being Creepy

PornUse 11 months ago

contest winner rewarded by bottoming for a cute ts

contest winner rewarded by bottoming for a cute ts

PornOne 2 months ago

Leona Ferrara and Carla Ferri and Alex Victor in Two Super Hot Trannies Versus One Penis Tranny

Leona Ferrara and Carla Ferri and Alex Victor in Two Super Hot Trannies Versus One Penis Tranny

AbTranny 9 years ago

Almost Took My Soul: The Bondage & Discipline Contest That Almost Destroyed My Life Proceeds

Almost Took My Soul: The Bondage & Discipline Contest That Almost Destroyed My Life Proceeds

GayVD 4 weeks ago

TranssexualNetwork.com - Cassidy Quinn's big tits in tranny fucking contest

TranssexualNetwork.com - Cassidy Quinn's big tits in tranny fucking contest

KeekAss 1 month ago

Jade Venus In Three Friends Have A Pussy Licking Competition Who Leads To A Lustful Threesome!

Jade Venus In Three Friends Have A Pussy Licking Competition Who Leads To A Lustful Threesome!

AbTranny 1 month ago

oopsie - codi vore rocky emerson gracie jane shemale threesome hardcore

oopsie - codi vore rocky emerson gracie jane shemale threesome hardcore

TransDoe 2 years ago

Janet Mason's hardbody striptease

58% HD 0:39 / 3:49

Janet Mason's hardbody striptease

FapHouse 4 years ago

Wedgie Competition

Wedgie Competition

Some.Porn 1 year ago

”Ebony babes battle in 100% real competitive erotic wrestling match”

”Ebony babes battle in 100% real competitive erotic wrestling match”

TransHero 6 months ago

Futanari Biggest Cock Street Contest – AI Generated Porn Video

Premium HD 1:22

Futanari Biggest Cock Street Contest – AI Generated Porn Video

Sheer 3 weeks ago

Professional Blowjob Queen: My Wife and the Trans Sucking My Cock Together!

Professional Blowjob Queen: My Wife and the Trans Sucking My Cock Together!

xHamster 1 month ago

Are you ready for my big black tranny cock

Are you ready for my big black tranny cock

xHamster 4 years ago

Wrestle for the Milk- lactating tits and the hard cock

HD 0:10 / 19:52

Wrestle for the Milk- lactating tits and the hard cock

LoyalFans 1 year ago

2 Sluts, 2 Mistresses - Extreme Deep & Double Fisting Race - Jasmine_dlight, Mistress Luciana, Adelina Noir & Fist Dude

2 Sluts, 2 Mistresses - Extreme Deep & Double Fisting Race - Jasmine_dlight, Mistress Luciana, Adelina Noir & Fist Dude

FapHouse 2 months ago

Femdom Ts Pool Party Fuck Fest

58% HD 0:11 / 26:16

Femdom Ts Pool Party Fuck Fest

Clips4sale 4 years ago

Team Effort

Some.Porn 2 years ago

The Honor Is Ours

The Honor Is Ours

Some.Porn 7 months ago

Wrestle for the Milk- Titties and Cock Milk

56% HD 0:39 / 19:56

Wrestle for the Milk- Titties and Cock Milk

FapHouse 1 year ago

Wrestle for the Milk- Titties and Cock Milk

60% HD 1:01 / 19:56

Wrestle for the Milk- Titties and Cock Milk

FapHouse 1 year ago

”Transgender babes Selene Santos & Jessy Dubai sharing a cunt feat. Marilyn Johnson”

”Transgender babes Selene Santos & Jessy Dubai sharing a cunt feat. Marilyn Johnson”

Faptor 2 years ago

Luna t-girl bi-atch summons you to an edging contest #1

Luna t-girl bi-atch summons you to an edging contest #1

TrannyGem 4 years ago

AFRO LESBOS - Black Pillow Fight Turns Into Squirts Competition

AFRO LESBOS - Black Pillow Fight Turns Into Squirts Competition

Ebony8 2 years ago

Competitive Shemale Ballerinas Having Sex With Bio-girl Dancer

Competitive Shemale Ballerinas Having Sex With Bio-girl Dancer

Eporner 1 year ago

belt On anal, suck Jobs, Face Sitting. Competitive Wrestling

belt On anal, suck Jobs, Face Sitting. Competitive Wrestling

AbTranny 7 years ago

Brazilian Beaty Contest 1999

Brazilian Beaty Contest 1999

getTranny 3 years ago

interracial wife swap foursome with shemales bianca meirelles and india taina dt729

interracial wife swap foursome with shemales bianca meirelles and india taina dt729

SukaPorn 2 years ago

Blowjob contest (captions TG story)

Blowjob contest (captions TG story)

Tranny.one 4 years ago

Blowjob Contest with the Literal Soccer Milf and Chef Clayton

Blowjob Contest with the Literal Soccer Milf and Chef Clayton

xHamster 2 months ago

”Perfect Assed Wet Teens Win A Swimming Competition & Reward Their Lustful Coach With A Triple Fuck”

”Perfect Assed Wet Teens Win A Swimming Competition & Reward Their Lustful Coach With A Triple Fuck”

ThePornstar 11 months ago

Izzy Wilde dominates her rival with rough sex after the game

Izzy Wilde dominates her rival with rough sex after the game

WeGotDicks 3 months ago

Girl On TS Girl Wrestling And Fucking

Girl On TS Girl Wrestling And Fucking

FreePorn8 5 years ago

”BLACKEDRAW 2 Blonde Sluts Twerk on Giant big black cocks”

”BLACKEDRAW 2 Blonde Sluts Twerk on Giant big black cocks”

ThePornstar 1 year ago

LETSDOEIT (CONTEST) - Huge Tits MILF Maid Chloe Lamour Perfect Anal Room Service

LETSDOEIT (CONTEST) - Huge Tits MILF Maid Chloe Lamour Perfect Anal Room Service

Fapcat 3 years ago

How Hot Can You Handle?

How Hot Can You Handle?

Some.Porn 1 year ago

Description for a FUTA Fight

58% HD 0:27 / 9:27

Description for a FUTA Fight

Clips4sale 1 year ago

Bells Rings Our

Bells Rings Our

Some.Porn 1 year ago

Miss Shemale America #3 - Sexy trannies are putting their best cock forward for the talent portion of the competition

Miss Shemale America #3 - Sexy trannies are putting their best cock forward for the talent portion of the competition

XVideos 4 years ago

”Sluts Compete who is the Better Pro Cocksucker”

”Sluts Compete who is the Better Pro Cocksucker”

ThePornstar 10 months ago

Goth Study Buddy's Self Sucking Contest (CEI)

67% 0:30 / 33:30

Goth Study Buddy's Self Sucking Contest (CEI)

Clips4sale 2 years ago

TGilrs CHALLENGE (round 30) - Keyla Marquesi 24 cm VSTauana

TGilrs CHALLENGE (round 30) - Keyla Marquesi 24 cm VSTauana

xHamster 3 years ago

DevilsFilm Hard Threesome Competition Turns Into Cum Mouth Sharing

DevilsFilm Hard Threesome Competition Turns Into Cum Mouth Sharing

BallsNBoobs 1 month ago

Lussuria Senza Freni - Episode 5

Lussuria Senza Freni - Episode 5

BallsNBoobs 3 months ago

”REALITY KINGS No Wanking Contest Pays off XXX”

”REALITY KINGS No Wanking Contest Pays off XXX”

ThePornstar 1 year ago

Slap my juicy ass!

Slap my juicy ass!

Some.Porn 1 year ago

Goth Tgirl Plays With Toys And Gets Creampied By A Dildo (selfcare Contest 2024)

Goth Tgirl Plays With Toys And Gets Creampied By A Dildo (selfcare Contest 2024)

AbTranny 5 days ago

Trans Poolgirl Rails The Fuck Out of Big Tittied Slut - GenderXFilms

Trans Poolgirl Rails The Fuck Out of Big Tittied Slut - GenderXFilms

BallsNBoobs 4 months ago

Super Stretcher

Super Stretcher

Some.Porn 1 year ago

Hot Sex With Her Slim Brunette Roommate Helps Busty Blonde Tranny Cope With Losing In Competitions

Hot Sex With Her Slim Brunette Roommate Helps Busty Blonde Tranny Cope With Losing In Competitions

AnySex 2 years ago

Ladyboy beauties jerks off faster and faster like a contest

Ladyboy beauties jerks off faster and faster like a contest

aShemaleTube 8 years ago

Tabatha Jordan: The Anal Cum-Back

Tabatha Jordan: The Anal Cum-Back

Some.Porn 1 year ago

”Win Minka's Bra, Tits & Muff!”

”Win Minka's Bra, Tits & Muff!”

TransHero 6 months ago

Love competitive swimsuits! The ninth installment in the series!

Love competitive swimsuits! The ninth installment in the series!

xHamster 3 weeks ago

”No Tipping Needed”

”No Tipping Needed”

ThePornstar 1 year ago

Cv Blonde Elf Burping

Cv Blonde Elf Burping

xHamster 1 year ago

Angel Allwood gets cocky, thinks she can take Ariel X down

Premium 44% HD 50:46

Angel Allwood gets cocky, thinks she can take Ariel X down

Kink 10 years 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”

429Men 1 month ago

Milky Moo Farms - Two Futanari Heifers Compete In a Milking Competition!

55% 0:11 / 3:11

Milky Moo Farms - Two Futanari Heifers Compete In a Milking Competition!

Clips4sale 3 years ago

TGilrs CHALLENGE (round 28) - Cris 20 cm VS Luana Pacheco 16

TGilrs CHALLENGE (round 28) - Cris 20 cm VS Luana Pacheco 16

xHamster 3 years ago

Kimber james sheboy

Kimber james sheboy

XVideos 9 years ago

VIP4K. Black stylist rewarded after helping white girl win the contest

VIP4K. Black stylist rewarded after helping white girl win the contest

Some.Porn 2 years ago

FalconStudios: Lustful really enjoys hard nailining

FalconStudios: Lustful really enjoys hard nailining

GayTube.site 4 years ago

Trans Male Jade Venus Fucks His Female GFs Olivia Jay And Little Puck

Trans Male Jade Venus Fucks His Female GFs Olivia Jay And Little Puck

Pornwhite 1 week ago

”Ryan can't wait to fuck Manuel guilt-free, but Kayley catches them in the act, leading to a wild threesome!”

”Ryan can't wait to fuck Manuel guilt-free, but Kayley catches them in the act, leading to a wild threesome!”

TransHero 6 months ago

Shemale hentai cuties bang cute angels / pleasing competition / cute bang / large rod / hot body / 25cminpussy

Shemale hentai cuties bang cute angels / pleasing competition / cute bang / large rod / hot body / 25cminpussy

SortPorn 10 months ago

SCORE Magazine Model of the Year Winners 2002-2021

SCORE Magazine Model of the Year Winners 2002-2021

Some.Porn 1 year ago

Shemale cock to cock wrestle and sexfight LOW

Shemale cock to cock wrestle and sexfight LOW

Clips4sale 2 years ago

Stiff Competition TS Tiffany Star Fucks the Living Cow Girl Hell Out of a Hot Southern Girl

Stiff Competition TS Tiffany Star Fucks the Living Cow Girl Hell Out of a Hot Southern Girl

aShemaleTube 4 months ago

Solo Competition Hard vs Slow Who Cums Harder Lonely Girlfriend Challenge

Solo Competition Hard vs Slow Who Cums Harder Lonely Girlfriend Challenge

xHamster 6 months ago

Now That's Hairy Ass Crack

Now That's Hairy Ass Crack

Some.Porn 1 year ago

cocotranse - jerk contest PMV - wondrous crossdressers

cocotranse - jerk contest PMV - wondrous crossdressers

TrannyGem 4 years ago

”SOUTHERNSTROKES Jamie Kelvin & Roman Schneider Raw Fuck”

”SOUTHERNSTROKES Jamie Kelvin & Roman Schneider Raw Fuck”

TransHero 6 months ago

Onlyfans contest winner screws Roxiexxx and gives her a creampie full of nut

Onlyfans contest winner screws Roxiexxx and gives her a creampie full of nut

ShemaleSin 4 years ago

Princesses Cock GROWTH contest - preview

Princesses Cock GROWTH contest - preview

aShemaleTube 8 years ago

A sensual competition

A sensual competition

aShemaleTube 12 years ago

Sissies&#039_ Anal Competition: Who&#039_ll Stay in the Cage? Who&#039_s in the Basement? Mistress Julia

Premium HD 15:01

Sissies&#039_ Anal Competition: Who&#039_ll Stay in the Cage? Who&#039_s in the Basement? Mistress Julia

xnxxGold 8 months ago

Find Me To Please Me

Find Me To Please Me

Some.Porn 1 year ago

”Alix Lynx & Aria Alexander's Fiery Double penetration Showdown”

”Alix Lynx & Aria Alexander's Fiery Double penetration Showdown”

TransHero 6 months ago

Kimber james ladyman

Kimber james ladyman

XVideos 8 years ago

Hot Doctor Gets Dominated

Hot Doctor Gets Dominated

Some.Porn 9 months ago

Measuring Contest

Measuring Contest

Eporner 6 months ago

”Mesmerizing Raven-Haired Beauties Compete in a Steamy Widow's Showdown”

”Mesmerizing Raven-Haired Beauties Compete in a Steamy Widow's Showdown”

StarWank 2 years ago

Game on! - the ultimate gaming challenge #gaming #competition

Game on! - the ultimate gaming challenge #gaming #competition

XXXShemalePorn 3 years ago

Hot-gangbang Without Condom

68% HD 1:01 / 18:54

Hot-gangbang Without Condom

FapHouse 1 year ago

Lucid Grows A Dick

52% 0:07 / 13:53

Lucid Grows A Dick

Clips4sale 3 years ago

Futa cock to cock battle and sexfight: Lana vs Nima LOW

Futa cock to cock battle and sexfight: Lana vs Nima LOW

Clips4sale 5 months ago

Kendra & Maria Get Down

Kendra & Maria Get Down

Some.Porn 1 year ago

Sissies' Anal Competition: Who'll Stay in the Cage? Who's in the Basement? Mastix Julia

Sissies' Anal Competition: Who'll Stay in the Cage? Who's in the Basement? Mastix Julia

ShemaleSin 8 months ago

Horny Crossdresser squirts on a dildo hands free then sucks it talks dirty to the camera

Horny Crossdresser squirts on a dildo hands free then sucks it talks dirty to the camera

xHamster 5 months ago

Orgasm Contest

Premium HD 17:54

Kink 16 years ago

Part 1 Sissies’ Anal Competition: Who's Going in the Cage? Who in the Basement? Mistress Julia

65% HD 1:01 / 7:38

Part 1 Sissies’ Anal Competition: Who's Going in the Cage? Who in the Basement? Mistress Julia

FapHouse 10 months ago

Horny Crossdresser Squirts on a Dildo Hands Free Then Sucks It Talks Dirty to the Camera

HD 0:39 / 16:04

Horny Crossdresser Squirts on a Dildo Hands Free Then Sucks It Talks Dirty to the Camera

FapHouse 5 months ago

This was the WINNING scene for BEST POV contest. Let&#039_s face it, it wasn&#039_t for nothing, right? I hope you like it _)

This was the WINNING scene for BEST POV contest. Let&#039_s face it, it wasn&#039_t for nothing, right? I hope you like it _)

XVideos 9 months ago

Part 2 Anal Competition Between Sissy: Barbie in the Cellar Mistress Julia

Part 2 Anal Competition Between Sissy: Barbie in the Cellar Mistress Julia

FapHouse 10 months ago

Lena Moon's Dirty Training for TS Bikini Comp

Lena Moon's Dirty Training for TS Bikini Comp

Jizzberry 2 years ago

TGilrs CHALLENGE (round 38) - Natalia De Robrus 20 cm VS

TGilrs CHALLENGE (round 38) - Natalia De Robrus 20 cm VS

xHamster 3 years ago

1 2 3 4 5

3,600 results found

Related categories

Competition Challenge Poker Hazing Locker Room Game Show Dare Amazon Stripper Lifeguard Exhibitionist Game Strip Club Swimming Aerobics Athletic Spin The Bottle Dancing lap dance Festival

Narrow your search

blowjob contest cum contest jerk off contest bikini contest wet t shirt contest handjob contest deepthroat contest strip contest nude contest nudist contest orgasm contest fuck contest piss contest anal contest lesbian contest squirt contest sex contest masturbation contest penis contest big butt contest

Categories Pornstars

Categories Pornstars

Parents

Pornmd.com uses the "Restricted To Adults" (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Pornmd.com. All rights reserved.

© 2026 Pornmd.com. All rights reserved.