Training Videos - Trans (50,218)

Sissy Scarlet Sky Spunk Compilation!

Sissy Scarlet Sky Spunk Compilation!

TrannyGem 1 year ago

Sarah and Lucy Feminize You and Mega-breezy You Out

Sarah and Lucy Feminize You and Mega-breezy You Out

TransTube.tv 1 year ago

Slut in transparent clothing ball gag and LED dog collar caught in public

Slut in transparent clothing ball gag and LED dog collar caught in public

XHamster 3 years ago

PHAT ASSED Femboy Slut Rides Dildo & CUMS

PHAT ASSED Femboy Slut Rides Dildo & CUMS

XHamster 4 years ago

BLOWBANG 2 fag dirty talk 33

BLOWBANG 2 fag dirty talk 33

Eporner 6 years ago

Anal make me Squirt in chastity

Anal make me Squirt in chastity

XHamster 6 months ago

Watch these Big Veiny Dildos Destroy and Ruin my Sissy Asshole until I get Thick Cum Anal Creampies

Watch these Big Veiny Dildos Destroy and Ruin my Sissy Asshole until I get Thick Cum Anal Creampies

XHamster 10 months ago

GRINDR FATHER POUNDS CD RIGID & FEEDS her a XXL MAMMARY FOUNTAIN of STEAMING JISM

GRINDR FATHER POUNDS CD RIGID & FEEDS her a XXL MAMMARY FOUNTAIN of STEAMING JISM

TrannyGem 4 years ago

Kendal Smithx Private Show

HD 2:00 / 30:46

Kendal Smithx Private Show

Camster 2 months ago

Sissy Yu Doll gets her ass lubed and fucked by bad dragon on a fuck machine

Sissy Yu Doll gets her ass lubed and fucked by bad dragon on a fuck machine

TrannyMovs 11 months ago

【コスプレ】リゼロのレムちゃん「コスプレイヤー」アナル調教！part.two

【コスプレ】リゼロのレムちゃん「コスプレイヤー」アナル調教！part.two

TrannyGem 1 year ago

Kendal Smithx Private Show

Kendal Smithx Private Show

Camster 3 months ago

He Slowly Became a Very Good Girl

He Slowly Became a Very Good Girl

XHamster 7 months ago

Submissive Ladyboy Anal Casting & Slave Training

Submissive Ladyboy Anal Casting & Slave Training

XHamster 9 months ago

Training My Throat

Training My Throat

XHamster 1 month ago

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 11

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 11

XHamster 2 months ago

Big Black Cock bull use femboy sissy phat culo rear end then breed it missionary noisy screaming tramp firm moist romping

Big Black Cock bull use femboy sissy phat culo rear end then breed it missionary noisy screaming tramp firm moist romping

Gay4Porn 2 years ago

Punished Slaves BDSM Bondage Gay Amador Big Dick 2

Punished Slaves BDSM Bondage Gay Amador Big Dick 2

XHamster 4 months ago

Turning Him Into A Sissy Slut

Turning Him Into A Sissy Slut

Tranny.one 2 years ago

Denise Humain works on her Asshole for 45 Minutes straight and to the limit.

Denise Humain works on her Asshole for 45 Minutes straight and to the limit.

XHamster 3 years ago

BlueCrow42's crossdressing adventure: double cumming on belly & ass while playing with long dildo

BlueCrow42's crossdressing adventure: double cumming on belly & ass while playing with long dildo

TrannyMovs 11 months ago

Kendal Smithx Private Show

HD 2:00 / 14:34

Kendal Smithx Private Show

Camster 8 months ago

Pussy Wrecking Vol.1

Pussy Wrecking Vol.1

XHamster 4 weeks ago

Hattabi4ik Insane Sissy Man Gold Rain Super Hot Gigantic Booty

Hattabi4ik Insane Sissy Man Gold Rain Super Hot Gigantic Booty

TrannyGem 1 year ago

Luna Florez Private Show

HD 2:00 / 14:45

Luna Florez Private Show

Camster 1 year ago

DaddyJayDee Training TSMolly

DaddyJayDee Training TSMolly

AShemaleTube 2 years ago

Ts Isabella loves sissy training for English Mistresses

Ts Isabella loves sissy training for English Mistresses

XHamster 3 years ago

Emma Devereaux Private Show

Emma Devereaux Private Show

Camster 2 years ago

Sissy Hope Compilation 4

Sissy Hope Compilation 4

XHamster 4 years ago

Sissy whiteboi in stockings enjoys deep slow strokes on a veiny BBC dildo stretching his ass

Sissy whiteboi in stockings enjoys deep slow strokes on a veiny BBC dildo stretching his ass

XHamster 3 years ago

TheArtemixx - Jayla's 1st Monster Schlong Training - Thick Trans Latin babe Takes ArtemiXXX's BBC and Sexy Load

TheArtemixx - Jayla's 1st Monster Schlong Training - Thick Trans Latin babe Takes ArtemiXXX's BBC and Sexy Load

Amateur8 1 week ago

Spandexfemboy - Anal Destruction Part 2 BBC Dildo

Spandexfemboy - Anal Destruction Part 2 BBC Dildo

XHamster 11 months ago

Sticking It Balls Deep in My Ass

Sticking It Balls Deep in My Ass

XHamster 3 days ago

Sissy Slut Fuck Doll Takes Anal Fisting, Pegging & Fuck Machine with HUGE DILDO Hardcore Femdom Porn!

Sissy Slut Fuck Doll Takes Anal Fisting, Pegging & Fuck Machine with HUGE DILDO Hardcore Femdom Porn!

Lesbian8 1 year ago

Happy sissy perplexed by multiple sissygasms riding enormous 12.5”/32cm Yam-sized Father faux shaft

Happy sissy perplexed by multiple sissygasms riding enormous 12.5”/32cm Yam-sized Father faux shaft

Transvids.tv 1 year ago

insatiable Milky twunk bonks dark Fem W Facial Cumshot

insatiable Milky twunk bonks dark Fem W Facial Cumshot

Gay4Porn 5 years ago

Sissy Whiteboy takes 8 inch BBC dildo balls-deep

Sissy Whiteboy takes 8 inch BBC dildo balls-deep

XHamster 3 years ago

Facefuck Training of my compliant girlfriend

Facefuck Training of my compliant girlfriend

Amateur8 2 months ago

Time to Submit Sissy

Time to Submit Sissy

XHamster 3 weeks ago

restrain bondage and kittling my sissy trip week four

restrain bondage and kittling my sissy trip week four

TrannyGem 3 years ago

PULVERIZING CREVICE!! DOMINA TRAINING PROSTATE EJACULATION COMPILATION

PULVERIZING CREVICE!! DOMINA TRAINING PROSTATE EJACULATION COMPILATION

TransTube.tv 1 year ago

Cumslut Training Jessica Bloom Self Suck Cumplay CEI Cu

Cumslut Training Jessica Bloom Self Suck Cumplay CEI Cu

Sheshaft 1 week ago

PMV Tart Pop - Sissy Peach plow along

PMV Tart Pop - Sissy Peach plow along

TrannyGem 3 years ago

Sissy in Lingerie Bounces on My Cock and Cums on My Tits

Sissy in Lingerie Bounces on My Cock and Cums on My Tits

XHamster 10 months ago

Brides Hands-free BBC Cumshots

Brides Hands-free BBC Cumshots

XHamster 2 months ago

Femboy Sounding in Chastity

Femboy Sounding in Chastity

XHamster 2 years ago

Sofia Rossi Intense Training With Dildo

Sofia Rossi Intense Training With Dildo

IcePorn 5 months ago

get on your knees sissy

get on your knees sissy

ShemaleSin 1 year ago

Rectal Screw with Pound Machine 1

Rectal Screw with Pound Machine 1

TrannyGem 2 years ago

flat caged sissygasm

flat caged sissygasm

ShemaleSin 1 year ago

Fucking Machine with Big Dildo Fucks Me Fast and Hard to Orgasm!

Fucking Machine with Big Dildo Fucks Me Fast and Hard to Orgasm!

XHamster 2 months ago

Sissy very first vid

Sissy very first vid

TrannyGem 2 years ago

Трахаю рукой и кабачком свою sissy шлюху. После чего она лижет жопу и пьет мочу со своей спермой

Трахаю рукой и кабачком свою sissy шлюху. После чего она лижет жопу и пьет мочу со своей спермой

TrannyGem 3 years ago

Trans Pup Prays for Dinky Instead of Handles – 4K Slow Edging Instructing

Trans Pup Prays for Dinky Instead of Handles – 4K Slow Edging Instructing

Gayhub 8 months ago

anal rides cowgirl and hands free climax carnal femboy gets enjoyment

anal rides cowgirl and hands free climax carnal femboy gets enjoyment

ShemaleSin 2 weeks ago

CEI Sissy Training - Hentai Tranced JOI

CEI Sissy Training - Hentai Tranced JOI

HentaiGem 1 year ago

AB112 Maid human toy instructing - splooging,jizz flow (Asian and English subtitles)

AB112 Maid human toy instructing - splooging,jizz flow (Asian and English subtitles)

TrannyGem 1 year ago

Training juicy ass to fist and BBC dildo

Training juicy ass to fist and BBC dildo

XHamster 1 year ago

Sissy Slut Pegging Compilation Vol.1

Sissy Slut Pegging Compilation Vol.1

XHamster 11 months ago

Random Captions

Random Captions

XHamster 4 months ago

Teen shemale training her asshole with big dildo

Teen shemale training her asshole with big dildo

Eporner 6 days ago

having a gorgeous sissy time

having a gorgeous sissy time

TransTube.tv 1 year ago

Girly Sissy Bitch! Jes Brinch Is a Weak Loser!

Girly Sissy Bitch! Jes Brinch Is a Weak Loser!

XHamster 3 months ago

Huge cock dildo destroyed my ass

Huge cock dildo destroyed my ass

XHamster 2 months ago

Stretching My Femboy Ass for a Big Plug

Stretching My Femboy Ass for a Big Plug

XHamster 2 weeks ago

Sasha Earth fuck her ass with sex toys anal massage

Sasha Earth fuck her ass with sex toys anal massage

XVideos 4 years ago

TRANSSEXUAL Carmen Masters Fucks Wordy Dreaded DL Thug A Fresh Fuckhole! He Falls In Love!

TRANSSEXUAL Carmen Masters Fucks Wordy Dreaded DL Thug A Fresh Fuckhole! He Falls In Love!

MyTransfix 2 months ago

Fucking my buttplug and gaping my sissy hole

Fucking my buttplug and gaping my sissy hole

XHamster 3 years ago

”Sarah Arabic is more interested in selfies than workouts, disrupting Nicole Aria's training sessions”

”Sarah Arabic is more interested in selfies than workouts, disrupting Nicole Aria's training sessions”

TransHero 6 months ago

Feminized sissy out for a walk

Feminized sissy out for a walk

GayDudesFucking 7 months ago

femboy maidboy and sissy maidgirl breeding (tough assfucking innocence plow with cassie coyote!)

femboy maidboy and sissy maidgirl breeding (tough assfucking innocence plow with cassie coyote!)

Transvids.tv 1 year ago

Assfuck Drilling Machine - Compil 14

Assfuck Drilling Machine - Compil 14

TrannyGem 2 years ago

Sissy Candy Rides Her Huge 16 Inch Dildo and Squirts a Little

Sissy Candy Rides Her Huge 16 Inch Dildo and Squirts a Little

XHamster 4 months ago

Anal Invasion Foray!zing Adventures of Krissy; Mr. Hankey’s Cutler X is, PERFUCKION ;)

Anal Invasion Foray!zing Adventures of Krissy; Mr. Hankey’s Cutler X is, PERFUCKION ;)

2BGay 3 years ago

Trans determined to dilute the gulp with his succulent nut nectar

Trans determined to dilute the gulp with his succulent nut nectar

TrannyGem 1 year ago

Pay your Slaver Girlfriend

Pay your Slaver Girlfriend

ShemaleSin 4 years ago

Sissy Gooner Goes Unfathomable on Bang Machine

Sissy Gooner Goes Unfathomable on Bang Machine

ShemaleSin 5 days ago

sissypov - mature sissy kati finnish swallowed all his cum

sissypov - mature sissy kati finnish swallowed all his cum

TransDoe 2 years ago

Trans Anal Training with Dildo

Trans Anal Training with Dildo

XHamster 1 year ago

Sissy fuckslut Creampied by BIG BLACK COCK onlyfans alexiakessel1

Sissy fuckslut Creampied by BIG BLACK COCK onlyfans alexiakessel1

TransTube.tv 1 year ago

Sissy Slut Michelle Morning Wake-up in Bangkok Hotel and Web Show

Sissy Slut Michelle Morning Wake-up in Bangkok Hotel and Web Show

XHamster 6 months ago

Sidney Puff Private Show

Sidney Puff Private Show

Camster 1 week ago

So hot cumming after 7 days in chastity and anal training

So hot cumming after 7 days in chastity and anal training

XHamster 1 year ago

Sissy Candy's Gets Used by Her Fucking Machine and Has Her Very First Sissygasm

Sissy Candy's Gets Used by Her Fucking Machine and Has Her Very First Sissygasm

XHamster 1 year ago

Bonnie Boombelle Party on Jul 6, 2026 - Part 2

Bonnie Boombelle Party on Jul 6, 2026 - Part 2

Camster 4 weeks ago

Large Ebony Fuck-Stick bull use femboy sissy monstrous backside rear end then breed it missionary loud bellowing mega-slut rock rock hard moist humping

Large Ebony Fuck-Stick bull use femboy sissy monstrous backside rear end then breed it missionary loud bellowing mega-slut rock rock hard moist humping

2BGay 3 years ago

Crossdressing gay torn up in the bootie

Crossdressing gay torn up in the bootie

TrannyGem 1 year ago

Sissy Owned By gf (Sissy Caption Story)

Sissy Owned By gf (Sissy Caption Story)

DeegX 3 years ago

Hana Rouse Private Show

4K 2:00 / 24:45

Hana Rouse Private Show

Camster 8 months ago

Feminization Fortune

Feminization Fortune

XHamster 3 weeks ago

POV Puppygirl Training &amp_ Breeding - Jaq Quicksilver trains you to serve him - ftm, mtf, strapon, handler, roleplay, domination, praise

POV Puppygirl Training &amp_ Breeding - Jaq Quicksilver trains you to serve him - ftm, mtf, strapon, handler, roleplay, domination, praise

XVideos 11 months ago

Hammering Her

Some.Porn 2 years ago

Sissy femboy in fishnet stockings jumps on a huge ribbed dildo - Closeup with deep anal penetration

Sissy femboy in fishnet stockings jumps on a huge ribbed dildo - Closeup with deep anal penetration

XHamster 2 weeks ago

Sissy Tries Butt Plug and Chastity For The First Time - Sissy Housewife

Sissy Tries Butt Plug and Chastity For The First Time - Sissy Housewife

XHamster 1 year ago

Punk damsels adore soles & spread out each others butt, wide open butt & sole humping

Punk damsels adore soles & spread out each others butt, wide open butt & sole humping

Transvids.tv 1 year ago

Sissy pegs her caged balls

Sissy pegs her caged balls

ShemaleSin 2 weeks ago

korean femboy kimono smashed

korean femboy kimono smashed

Gay4Porn 1 year ago

Blondie TRANSSEXUAL barebacks marine

Blondie TRANSSEXUAL barebacks marine

TrannyGem 3 years ago

Anouk Tgirl Wench - Bareback Facefuck BBC Destroys her Sissy Butt and Mouth in 4 hrs - Full Clip

Anouk Tgirl Wench - Bareback Facefuck BBC Destroys her Sissy Butt and Mouth in 4 hrs - Full Clip

SortPorn 3 years ago

Checking Locked Dick and Strapon

Checking Locked Dick and Strapon

XHamster 2 years ago

becomingfemme - jessica nicole sensual sissy bunny

becomingfemme - jessica nicole sensual sissy bunny

TransDoe 2 years ago

Unedited sissy training

Unedited sissy training

ShemaleSin 5 days ago

Sissy ruined climax after lengthy denial out of a single touch on dong

Sissy ruined climax after lengthy denial out of a single touch on dong

ShemaleSin 2 weeks ago

Part 3 POV Blowjob and Viber Fucking a Sexy Witch Until Cum

Part 3 POV Blowjob and Viber Fucking a Sexy Witch Until Cum

XHamster 4 months ago

Take this fuckin' test and witness if you're a sissy (FEMINIZATION ROLEPLAY - AI GENERATED)

Take this fuckin' test and witness if you're a sissy (FEMINIZATION ROLEPLAY - AI GENERATED)

HentaiGem 1 year ago

Latex gimp pegged

Latex gimp pegged

ShemaleSin 6 months ago

Staying Plugged for a Long Time After Ruining My Pussy for 10 Hours

Staying Plugged for a Long Time After Ruining My Pussy for 10 Hours

XHamster 7 months ago

Hard Results

Some.Porn 2 years ago

Sissy Academy, Lesson#1 student Presentation

Sissy Academy, Lesson#1 student Presentation

XHamster 6 months ago

TRANSFIXED - Horny Zariah Aura Tames MILF Kenzie Taylor's Wild Pussy!ROUGH SEX

TRANSFIXED - Horny Zariah Aura Tames MILF Kenzie Taylor's Wild Pussy!ROUGH SEX

Some.Porn 1 year ago

becoming femme - gwen how could you look at this and want a pussy after porn video

becoming femme - gwen how could you look at this and want a pussy after porn video

TransDoe 1 year ago

Sissy in the jacuzzi

Sissy in the jacuzzi

ShemaleSin 11 months ago

Hairy Tranny Fucked Hard

Hairy Tranny Fucked Hard

Eporner 1 year ago

most good riding hot femboy large compilation amateur anal

most good riding hot femboy large compilation amateur anal

ShemaleSin 1 year ago

Luna Florez Private Show

4K 2:00 / 12:25

Luna Florez Private Show

Camster 3 months ago

Nymph TEAR UP T-MODEL NUN compilation

Nymph TEAR UP T-MODEL NUN compilation

TransTube.tv 1 year ago

Dropped My Stretched Anal On a Biggest Ribbed Cone Sex-toy - Chastity Cage Hands Free Ejaculation

Dropped My Stretched Anal On a Biggest Ribbed Cone Sex-toy - Chastity Cage Hands Free Ejaculation

ShemaleSin 2 months ago

Blacked Big Ass Trans Samus Anal Creampie and Huge Cumfarts

Blacked Big Ass Trans Samus Anal Creampie and Huge Cumfarts

XHamster 6 months ago

Female Dom Smacks and Cages 2 TRANSSEXUAL Subjugated Sissy Fucksluts

Female Dom Smacks and Cages 2 TRANSSEXUAL Subjugated Sissy Fucksluts

TrannyGem 5 years ago

Rough prostate massage with hottest cumshot for twink femboy

Rough prostate massage with hottest cumshot for twink femboy

XHamster 2 years ago

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