Training Videos - Trans (124,133)

Becoming A Sissy (Jerk Off Instructions) w/ Raven Gray

Becoming A Sissy (Jerk Off Instructions) w/ Raven Gray

TrannyGem 4 years ago

Adell Goddess Private Show

Adell Goddess Private Show

Camster 2 years ago

Sophia Loreen Party on Sep 10, 2026 - Part 3

4K 2:00 / 23:02

Sophia Loreen Party on Sep 10, 2026 - Part 3

Camster 1 week ago

4 Fingers Inside My Pussy, Squirt and Finish

59% 4K 2:00 / 1:20:13

4 Fingers Inside My Pussy, Squirt and Finish

Flirt4Free 5 months ago

Lick the taste of ass from my finger KellyAErick

Lick the taste of ass from my finger KellyAErick

Tranny.one 3 years ago

Ultra-cute Femboy in Fishnets Instructs his Rear entrance until he Ejaculates on Himself

Ultra-cute Femboy in Fishnets Instructs his Rear entrance until he Ejaculates on Himself

4Gay 8 months ago

Chastity stepson Dilon Cum on his Horny Stepmother flesh Stockings Feet - Cock Teasing Shoe High Heels, Lot of Cum on Toes, Pantyhose Footjobs, Cum on Belly, Dangling her Sexy Long Toes, ToeJobs close up, Highly arched soles

64% 4K 0:25 / 16:22

Chastity stepson Dilon Cum on his Horny Stepmother flesh Stockings Feet - Cock Teasing Shoe High Heels, Lot of Cum on Toes, Pantyhose Footjobs, Cum on Belly, Dangling her Sexy Long Toes, ToeJobs close up, Highly arched soles

Clips4sale 11 months ago

Fag Teaching

Transvids.tv 11 months ago

Sissy Shiera Anal Fingering Goon Session - Webcam

Sissy Shiera Anal Fingering Goon Session - Webcam

XHamster 6 days ago

Winter Rae's Busty Sex Training

Winter Rae's Busty Sex Training

Some.Porn 2 years ago

Double Enemas, Custard, Bananas And A Sweet Mess All Over Us Clip 1

Double Enemas, Custard, Bananas And A Sweet Mess All Over Us Clip 1

XHamster 9 months ago

Tiara Rossi Private Show

Tiara Rossi Private Show

Flirt4Free 2 years 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 1 year ago

Sophia Loreen Party on Jul 29, 2026 - Part 3

62% 4K 2:00 / 1:17:55

Sophia Loreen Party on Jul 29, 2026 - Part 3

Flirt4Free 1 month ago

Wondrous Fem Dom and Mature Shemale Predominate and Fem a Sissy

Wondrous Fem Dom and Mature Shemale Predominate and Fem a Sissy

TrannyGem 5 years ago

Whimper and Beg Obedience Training JOI

Whimper and Beg Obedience Training JOI

XHamster 2 weeks ago

Latino Studs Go At It

58% HD 2:00 / 38:43

Latino Studs Go At It

Flirt4Free 8 years ago

Mistress Training Sissy Femboy

Mistress Training Sissy Femboy

Tranny.one 3 years ago

Jewel Selfsucker Private Show

58% HD 2:00 / 8:28

Jewel Selfsucker Private Show

Flirt4Free 1 week ago

Kendal Smithx Private Show

HD 2:00 / 28:08

Kendal Smithx Private Show

Flirt4Free 9 months ago

Master & Ithan & Aleex Private Show

52% HD 2:00 / 38:32

Master & Ithan & Aleex Private Show

Flirt4Free 1 year ago

Etéreo SissyClown in Puppy Posture using Fake Penis

Etéreo SissyClown in Puppy Posture using Fake Penis

GayCK 4 years ago

Anal Training #14 Tanned Femboy Fucks Himself in the Ass and Cums

HD 1:01 / 39:01

Anal Training #14 Tanned Femboy Fucks Himself in the Ass and Cums

FapHouse 1 year ago

Tantaly : Chastity Release: The Last Penetration of your Life? Mistress Julia

Tantaly : Chastity Release: The Last Penetration of your Life? Mistress Julia

XHamster 2 years ago

Submissive male slave pegged by his dominating mistress

Submissive male slave pegged by his dominating mistress

XGroovy 2 years 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!

XHamster 1 year ago

Harris Morrison Private Show

HD 2:00 / 45:59

Harris Morrison Private Show

Flirt4Free 2 years ago

She's Going to Get Her Ass Fucked in the Kitchen

She's Going to Get Her Ass Fucked in the Kitchen

XHamster 1 year ago

Female Dominance Domme tears up fuckslut sissy backside, dual jism rectal ejaculation

Female Dominance Domme tears up fuckslut sissy backside, dual jism rectal ejaculation

TrannyGem 3 years ago

Handsome Muscle Hunk Brad Knox Reclines on Bed

HD 2:00 / 21:17

Handsome Muscle Hunk Brad Knox Reclines on Bed

Flirt4Free 11 years ago

Bella Joie Takes Control: Throat Training & Ass Wrecking till she cums

Bella Joie Takes Control: Throat Training & Ass Wrecking till she cums

Clips4sale 1 year ago

Tiara Rossi Private Show

Tiara Rossi Private Show

Camster 2 years ago

My BBC for you and your wife, sissy cuck! 28 min (MaleDom)

50% HD 0:30 / 27:46

My BBC for you and your wife, sissy cuck! 28 min (MaleDom)

Clips4sale 1 year ago

I Cumming on the Top!!!! Free Hands Sissygasm

69% HD 0:39 / 3:17

I Cumming on the Top!!!! Free Hands Sissygasm

FapHouse 3 months ago

Slap My Horny Ass ^^

Slap My Horny Ass ^^

Camster 1 year ago

Sandy Nell Private Show

62% HD 2:00 / 4:19

Sandy Nell Private Show

Flirt4Free 5 years ago

BNWO Prisoner Orientation Video

60% 4K 0:26 / 12:53

BNWO Prisoner Orientation Video

Clips4sale 1 year ago

Big ass teen latinaccompilation

Big ass teen latinaccompilation

XHamster 9 months ago

FUCK PUSSY BOY - Part 3

60% 4K 2:00 / 9:48

FUCK PUSSY BOY - Part 3

Flirt4Free 6 months ago

”A Gym Just For Us 2”

”A Gym Just For Us 2”

TransHero 9 months ago

Are you really wearing my Swimsuit and Stockings

Are you really wearing my Swimsuit and Stockings

XHamster 2 years ago

I collected 2 SISSYGASMS after PEGGING

I collected 2 SISSYGASMS after PEGGING

XHamster 1 year ago

Extreme Games in Hot Clothes!

Extreme Games in Hot Clothes!

XHamster 3 months ago

White High Heels And Playing With Dildos

White High Heels And Playing With Dildos

XHamster 1 year ago

PissMop Sissy Pissy Kitten Dbl Vision Ahegao Cougar

PissMop Sissy Pissy Kitten Dbl Vision Ahegao Cougar

AShemaleTube 2 weeks ago

Femdom POV: Sissy

Femdom POV: Sissy

XHamster 3 months ago

Angie Mendoza Private Show

Angie Mendoza Private Show

Flirt4Free 4 years ago

BIG BOOTY Sissy Slut Fucks Eager Hole With Dildo & CUMS

BIG BOOTY Sissy Slut Fucks Eager Hole With Dildo & CUMS

XHamster 3 years ago

Shemale in fishnets rides dildo till she cums - Amateur Solo

Shemale in fishnets rides dildo till she cums - Amateur Solo

AnySex 2 years ago

Sloppy wet anal pussy gets machine fucked until anal orgasm Clip 1

Sloppy wet anal pussy gets machine fucked until anal orgasm Clip 1

XHamster 1 year ago

While His Boyfriend Isn't Watching, He Gets on His Knees and Swallows

While His Boyfriend Isn't Watching, He Gets on His Knees and Swallows

XHamster 1 year ago

Hard Sissy Trainning Milking Cumshots Sissygasm

Hard Sissy Trainning Milking Cumshots Sissygasm

XHamster 4 months ago

IMMENSE DARK-HUED TRUNK PARENT USES CAGED YT SISSYBOY : your Black neighbor gets your sonny high and teaches him to conform

IMMENSE DARK-HUED TRUNK PARENT USES CAGED YT SISSYBOY : your Black neighbor gets your sonny high and teaches him to conform

2BGay 3 years ago

Suck It For Futa Step-Mommy

Suck It For Futa Step-Mommy

Clips4sale 1 year ago

Maya Spring Party on Aug 24, 2026 - Part 4

4K 2:00 / 37:31

Maya Spring Party on Aug 24, 2026 - Part 4

Flirt4Free 1 month ago

What a Slutty Sissy You Are

What a Slutty Sissy You Are

XHamster 8 months ago

”Daisy Taylor wears miniskirt without panties on the train! This makes Johnny lustful as fuck!”

”Daisy Taylor wears miniskirt without panties on the train! This makes Johnny lustful as fuck!”

Rainblow 2 years ago

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

XHamster 1 year ago

Mommy Mari NSFW - Mommy Mari's Sissy Lessons: Anal & Blowjob Training with a Milf

Mommy Mari NSFW - Mommy Mari's Sissy Lessons: Anal & Blowjob Training with a Milf

EpicGFs 4 weeks ago

Facessiting Bullying Sissy Session - Feat Goddess Marcy, Lucy Puddles and Trans Goddess Rose (1080p)

HD 0:31 / 10:32

Facessiting Bullying Sissy Session - Feat Goddess Marcy, Lucy Puddles and Trans Goddess Rose (1080p)

Clips4sale 1 week ago

Crhistian & Dereckk & Friends Party on Mar 24, 2019

HD 2:00 / 25:33

Crhistian & Dereckk & Friends Party on Mar 24, 2019

Flirt4Free 7 years ago

My man wore sexy underwear for me, he left them here and I am sniffing them!

My man wore sexy underwear for me, he left them here and I am sniffing them!

XHamster 2 months ago

Cameron Minx

Some.Porn 1 year ago

JOI Jerk off Instruction and Sissification for Newbie Slut

JOI Jerk off Instruction and Sissification for Newbie Slut

XHamster 1 year ago

Big Ass Shemale Mating Press with Bbc and HUGE Creampie

Big Ass Shemale Mating Press with Bbc and HUGE Creampie

XHamster 9 months ago

Angie Mendoza Private Show

Angie Mendoza Private Show

Flirt4Free 1 year ago

Ladyboy Peeing Compilation - A Wild Ladyboy's Trained Adventure

Ladyboy Peeing Compilation - A Wild Ladyboy's Trained Adventure

TrannyMovs 5 months ago

fat lucky guy fucks a latin shemale lima peru venezuela ambar

fat lucky guy fucks a latin shemale lima peru venezuela ambar

PornBox 6 years ago

She-Cock Cuckold Wedding Desecration

HD 0:30 / 12:21

She-Cock Cuckold Wedding Desecration

Clips4sale 4 months ago

Master & Christian & Nicco Private Show

Master & Christian & Nicco Private Show

Flirt4Free 2 years ago

Fisting my Ass with a full Bladder until I Squirt

Fisting my Ass with a full Bladder until I Squirt

XHamster 1 year ago

Feminizing and Pissing on a Sissy Slut MOV

HD 0:13 / 14:57

Feminizing and Pissing on a Sissy Slut MOV

Clips4sale 4 months ago

TRANSFIXED - Casey Kisses Trains Friend To Pleasure Trans Girls With Hot Anal And Double Cumshot

TRANSFIXED - Casey Kisses Trains Friend To Pleasure Trans Girls With Hot Anal And Double Cumshot

AShemaleTube 1 week ago

Rubidoll Anal Sex After Work

Rubidoll Anal Sex After Work

XHamster 1 week ago

Sissy Jessica Bloom Spitroast Training With Fucking Machine And Dildos - Anal Sissygasms and Cumswallow

Sissy Jessica Bloom Spitroast Training With Fucking Machine And Dildos - Anal Sissygasms and Cumswallow

XHamster 5 months ago

Black King's Sissy Jizm Squirt SISSY TEACHING ASMR Jerk Off Instructions

Black King's Sissy Jizm Squirt SISSY TEACHING ASMR Jerk Off Instructions

HentaiGem 6 months ago

Feminized for Girls Night Out (full Movie)

Feminized for Girls Night Out (full Movie)

XHamster 4 months ago

Cute 18 Year Old Virgin Trans Girl Dessietsa Takes Big Ass Anal Toys

Cute 18 Year Old Virgin Trans Girl Dessietsa Takes Big Ass Anal Toys

XGroovy 1 year ago

Fuck-Fest Gimps sixty-nine Dual female domination Pegging and Sissy Jizzing with Face-Sitting on the Fuckmachine

Fuck-Fest Gimps sixty-nine Dual female domination Pegging and Sissy Jizzing with Face-Sitting on the Fuckmachine

TrannyGem 11 months ago

QOS BBC Whiteboi Training [Part3]

QOS BBC Whiteboi Training [Part3]

Tranny.one 1 year ago

Sophia Loreen Private Show

62% 4K 2:00 / 9:47

Sophia Loreen Private Show

Camster 1 month ago

Tranny Gwen Tennyson Destroying Her Ass with BBC Fat Dildo for the First Time (round 1)

Tranny Gwen Tennyson Destroying Her Ass with BBC Fat Dildo for the First Time (round 1)

XHamster 1 month ago

Dress Up Sissy Costume Tasks

HD 0:29 / 10:44

Dress Up Sissy Costume Tasks

Clips4sale 11 months ago

Paulo & Jose & Sander Private Show

59% HD 2:00 / 7:57

Paulo & Jose & Sander Private Show

Flirt4Free 3 months ago

🎬 Sissy Squirting (RUS lang.) - SissyGasms Handsfree Cum Trainer (2026)

🎬 Sissy Squirting (RUS lang.) - SissyGasms Handsfree Cum Trainer (2026)

Pornicom 1 day ago

Unfathomable anal fisting my hunk toy with mother I'd like to fuck Lisa and tranny Charlotte

Unfathomable anal fisting my hunk toy with mother I'd like to fuck Lisa and tranny Charlotte

MatureTubeHere 2 years ago

World Record Climax - nine Seconds Cum-shot Lil Bone in Innocence

World Record Climax - nine Seconds Cum-shot Lil Bone in Innocence

2BGay 1 year ago

Anal Slut fisting training dildo

Anal Slut fisting training dildo

XHamster 1 year ago

Sissy White T-Woman Lucy in V-Card Anal Invasion Nail by ten Inch BIG BLACK COCK Black Bull

Sissy White T-Woman Lucy in V-Card Anal Invasion Nail by ten Inch BIG BLACK COCK Black Bull

TrannyGem 4 years ago

Nettle spanking

Nettle spanking

XHamster 3 years ago

Sissy Femboy in Body Stocking Riding Huge Anal Dildo

Sissy Femboy in Body Stocking Riding Huge Anal Dildo

XHamster 3 months ago

Your Trans BFF Wants to Make You Her Boyfriend's Mall Slut!

Your Trans BFF Wants to Make You Her Boyfriend's Mall Slut!

XHamster 2 years ago

Rubidoll penetrates her small pussy with a BBC dildo

Rubidoll penetrates her small pussy with a BBC dildo

XHamster 2 weeks ago

Pissy Sissy

65% HD 0:25 / 18:02

Clips4sale 1 year ago

Jacob Malik Private Show

33% HD 2:00 / 8:51

Jacob Malik Private Show

Flirt4Free 1 year ago

Caged femboy trains ass & cums💦

Caged femboy trains ass & cums💦

AShemaleTube 1 year ago

Sex Slave, Submissive In Front Of A Beautiful Cock In FACeFuckiNg For The St❤️ 🔥ValenTin VaneSsaBiTCHx PariSChienneTrvprod⁹¹

Sex Slave, Submissive In Front Of A Beautiful Cock In FACeFuckiNg For The St❤️ 🔥ValenTin VaneSsaBiTCHx PariSChienneTrvprod⁹¹

XHamster 7 months 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

Desire Sweet Private Show

HD 2:00 / 12:08

Desire Sweet Private Show

Flirt4Free 1 year ago

Brides Hands-free BBC Cumshots

63% HD 0:39 / 4:53

Brides Hands-free BBC Cumshots

FapHouse 4 months ago

onlyfans - yasmine lee wanna play with this milf girldick porn video

onlyfans - yasmine lee wanna play with this milf girldick porn video

TransDoe 1 year ago

Angie Mendoza Private Show

Angie Mendoza Private Show

Flirt4Free 6 months ago

Fetish foolish Marilyn Monroe like transvestite banging thick black fuck stick

Fetish foolish Marilyn Monroe like transvestite banging thick black fuck stick

TrannyGem 3 years ago

Trans Gwen Tennyson Extreme Massive Anal Creampies and Cumfarts After Being Ass Fucked with Inflatable Dildo

Trans Gwen Tennyson Extreme Massive Anal Creampies and Cumfarts After Being Ass Fucked with Inflatable Dildo

XHamster 7 months ago

Big Ass Samus Femboy Anal Pounded by Two Big Black Cocks

Big Ass Samus Femboy Anal Pounded by Two Big Black Cocks

XHamster 8 months ago

Sophia Loreen Party on Sep 4, 2026 - Part 2

4K 2:00 / 54:21

Sophia Loreen Party on Sep 4, 2026 - Part 2

Camster 2 weeks ago

Anal Fuck Sissygasm Practice

Anal Fuck Sissygasm Practice

XHamster 5 months ago

Chunky Butt Femboy Raven Backdoor Gaped, Creampie and Cuming After Intensive Anal Sex with BBC Vibrator

Chunky Butt Femboy Raven Backdoor Gaped, Creampie and Cuming After Intensive Anal Sex with BBC Vibrator

ShemaleSin 2 months ago

Mistress Makes Crossdresser Masochist Suck Her Strap-on Dick and Inserts Her Finger Into His Anus and Stirring It Around

Mistress Makes Crossdresser Masochist Suck Her Strap-on Dick and Inserts Her Finger Into His Anus and Stirring It Around

XHamster 5 months ago

AB112 Maid human fucktoy training - squirting,cumshot (Chinese and English subtitles)

AB112 Maid human fucktoy training - squirting,cumshot (Chinese and English subtitles)

XHamster 2 years ago

Gag Slut Training

Gag Slut Training

Eporner 4 years ago

Kinky Bitch - sissy training part 1

68% 4K 0:43 / 12:10

Kinky Bitch - sissy training part 1

Clips4sale 4 months ago

AB140 Mimi Bao's Introduction to BDSM Training -Blowjob,Sex (Chinese and English subtitles)

AB140 Mimi Bao's Introduction to BDSM Training -Blowjob,Sex (Chinese and English subtitles)

XHamster 1 year ago

Caged sissy begs for release while teased by Magic Wand

Caged sissy begs for release while teased by Magic Wand

XXXXCum 1 year ago

trans in chastity extreme gape with inflateable butt plug

73% 0:13 / 7:16

trans in chastity extreme gape with inflateable butt plug

Clips4sale 1 year ago

Interactive Sissy Quiz - How Big of a Sissy Slut Are You?

HD 1:00 / 13:23

Interactive Sissy Quiz - How Big of a Sissy Slut Are You?

Clips4sale 5 months ago

Arab Sissy Crossdresser POINT OF VIEW ASS FUCKING Mikah BONED by BIG BLACK COCK Parent - Jaw-dropping CD POINT OF VIEW Rectal

Arab Sissy Crossdresser POINT OF VIEW ASS FUCKING Mikah BONED by BIG BLACK COCK Parent - Jaw-dropping CD POINT OF VIEW Rectal

TransTube.tv 2 years ago

POV Hard Pegging Jasmine Dlight From Mistress

POV Hard Pegging Jasmine Dlight From Mistress

XHamster 10 months ago

My gape anal pic colections

My gape anal pic colections

XHamster 9 months ago

Black BBW TRANSSEXUAL Threesome With TRANSSEXUAL Carmen Masters & TRANSSEXUAL Patra.. Uncircumcised BIG BLACK DICK Dual Internal cum shot!

Black BBW TRANSSEXUAL Threesome With TRANSSEXUAL Carmen Masters & TRANSSEXUAL Patra.. Uncircumcised BIG BLACK DICK Dual Internal cum shot!

MyTransfix 1 month ago

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