Training Videos - Trans (90,056)

Stretching my Pussy Nice and Big!!!

Stretching my Pussy Nice and Big!!!

xHamster 2 years ago

Becky Scolds Sissy Slut Michel for Not Cleaning the Kitchen Properly

65% HD 1:01 / 50:55

Becky Scolds Sissy Slut Michel for Not Cleaning the Kitchen Properly

FapHouse 1 year ago

Chastity Sissys Desperate Dildo Training Captivating Caption Story

Chastity Sissys Desperate Dildo Training Captivating Caption Story

xHamster 10 months ago

Jizzing from shagging plums

Jizzing from shagging plums

Gayhub 3 months ago

Mama Studio on Training my step nephew how to munch a trans for the very first time

Mama Studio on Training my step nephew how to munch a trans for the very first time

KeekAss 2 months ago

Sabrinna Naughty Private Show

Sabrinna Naughty Private Show

Flirt4Free 7 years ago

Corporate training part 1 to 4

Corporate training part 1 to 4

Pornwhite 2 weeks ago

Dumb Gagged Bitch Premature Cum

Dumb Gagged Bitch Premature Cum

xHamster 6 months ago

Sissy Elise idolizes fuckpole up close

Sissy Elise idolizes fuckpole up close

TrannyGem 3 years ago

Watch Bella Roar's big boobs bounce as she obediently takes on her master's big cock

Watch Bella Roar's big boobs bounce as she obediently takes on her master's big cock

TrannyMovs 7 months ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 1 week ago

Sissy Kanisa Crossdresser Play with Anal Bead Vibrator on Her Creampie Anal

Sissy Kanisa Crossdresser Play with Anal Bead Vibrator on Her Creampie Anal

FapHouse 1 year ago

The Anal!zing Adventures of Krissy: Jake the Minotaur Pounds my Booty Sore

The Anal!zing Adventures of Krissy: Jake the Minotaur Pounds my Booty Sore

ShemaleSin 1 year ago

TRANSSEXUAL Willow Hammerz - Sissy Instructing PMV

TRANSSEXUAL Willow Hammerz - Sissy Instructing PMV

TrannyGem 5 months ago

Sissy Ass Fucked Right Over the Camera Compilation 2

Sissy Ass Fucked Right Over the Camera Compilation 2

xHamster 2 months ago

Artesca Private Show

HD 2:00 / 16:18

Artesca Private Show

Flirt4Free 6 days ago

I'm plan to turn u into my little wench and bang your mouth raw with my large, palpitating jock - FEMINIZATION ROLEPLAY - AI

I'm plan to turn u into my little wench and bang your mouth raw with my large, palpitating jock - FEMINIZATION ROLEPLAY - AI

ShemaleSin 10 months ago

Aj180 Presents: Assmr

Aj180 Presents: Assmr

FapHouse 9 months ago

cum craver

aShemaleTube 1 year ago

Bulls Paying for Your Pink Panties

Bulls Paying for Your Pink Panties

xHamster 5 months ago

Latex Doll huge dildo

Latex Doll huge dildo

Pornzona 1 day ago

The Sissy Therapie at Lou Nesbit, Lia Louise

The Sissy Therapie at Lou Nesbit, Lia Louise

Tranny.one 1 year ago

Futa Anal Training - Stronger by the day. (Sample)

Futa Anal Training - Stronger by the day. (Sample)

Eporner 1 year ago

Trans sounding and orgazm

Trans sounding and orgazm

TrannyGem 2 years ago

Lula Sissy's Sluttyfication: So Super-Cute To Be A Super-Bitch!

Lula Sissy's Sluttyfication: So Super-Cute To Be A Super-Bitch!

TrannyGem 3 years ago

Installing the fuckfest woman program GAY FLICK VERSION

Installing the fuckfest woman program GAY FLICK VERSION

TrannyGem 1 year ago

Sissy Training

xHamster 1 year ago

Bittersweetqueen Sissy Training On Live Cam

Bittersweetqueen Sissy Training On Live Cam

DrTuber 2 months ago

Lisa and t-girl Lucy anal training and chastity

Lisa and t-girl Lucy anal training and chastity

MatureTubeHere 4 years ago

Training to become a sissy cuckold

Training to become a sissy cuckold

DrTuber 2 years ago

Sissy rides dildo BUTT ASS NAKED & CUMS!

Sissy rides dildo BUTT ASS NAKED & CUMS!

xHamster 4 years ago

hole fucked pissed and cum in mouth

HD 0:23 / 40:30

hole fucked pissed and cum in mouth

PornBox 11 months ago

The Cucumber Sissygasm Session Sissy Training

The Cucumber Sissygasm Session Sissy Training

xHamster 3 months ago

sissy crossdresser piss drinking from condom and masturbating cum

sissy crossdresser piss drinking from condom and masturbating cum

PissVids 1 year ago

Voice training

SortPorn 19 hours ago

Sissy with large milk cans jacking off for the camera

Sissy with large milk cans jacking off for the camera

TrannyGem 3 years ago

Cumslut Pop Training 2

Cumslut Pop Training 2

aShemaleTube 2 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 2 years ago

Luciana Sainz Private Show

4K 2:00 / 15:59

Luciana Sainz Private Show

Flirt4Free 1 month ago

POINT OF VIEW HER DESTRYING MY CABOOSE ENTIRE WITH HER eighteen" INCH BIG BLACK COCK!

POINT OF VIEW HER DESTRYING MY CABOOSE ENTIRE WITH HER eighteen" INCH BIG BLACK COCK!

TrannyGem 2 years ago

Knot Wench Depth Training Teaser

Knot Wench Depth Training Teaser

ShemaleSin 11 months ago

Snowbunny Slut Drooling on BBC Toy

Snowbunny Slut Drooling on BBC Toy

xHamster 7 months ago

PHAT ASSED Femboy Slut Rides Dildo & CUMS

PHAT ASSED Femboy Slut Rides Dildo & CUMS

xHamster 4 years ago

Sexy Ts Girl Suck 36cm Dildo So Deep Mmmm

Sexy Ts Girl Suck 36cm Dildo So Deep Mmmm

Flirt4Free 3 years ago

New 2024 - Miss Me?

New 2024 - Miss Me?

xHamster 2 years ago

Maid Into A Slut - Erica Cherry And Sinn Sage MP4

55% 0:20 / 31:42

Maid Into A Slut - Erica Cherry And Sinn Sage MP4

Clips4sale 3 years ago

Trans caught dressed in ultra-cute undies in public

Trans caught dressed in ultra-cute undies in public

TrannyGem 10 months ago

Horny sissy Playing with her ass

Horny sissy Playing with her ass

Clips4sale 1 year ago

Deep down I know you're a girly girl

Deep down I know you're a girly girl

xHamster 11 years ago

Helpless Sissy T-girl: Tied up, Toyed with Monster Dildo & Fucked

Helpless Sissy T-girl: Tied up, Toyed with Monster Dildo & Fucked

xHamster 2 months ago

HOT Orgasms and CumShots Compilation

HOT Orgasms and CumShots Compilation

Pornzona 1 month ago

Sissy Dildo training in public

Sissy Dildo training in public

Eporner 3 months ago

”Assfucking training for two sexy sluts”

”Assfucking training for two sexy sluts”

TransHero 4 months ago

Submissive tranny whores and cumsluts get tied up and trained

Submissive tranny whores and cumsluts get tied up and trained

Tranny.one 8 years ago

Independent training No34 Tight skirt rolled up bra exposed walk

Independent training No34 Tight skirt rolled up bra exposed walk

xHamster 4 months ago

Sissy Fag Tranny Training Self Help

Sissy Fag Tranny Training Self Help

Eporner 5 years ago

Win A Bet For Me

55% HD 0:10 / 8:04

Win A Bet For Me

LoyalFans 9 months ago

Sophia Loreen Private Show

4K 2:00 / 2:00:04

Sophia Loreen Private Show

Flirt4Free 7 months ago

Tantaly : Chastity Release after a Month: Humiliating Penetration and Degradation for this Sissy - Mistress Julia

Tantaly : Chastity Release after a Month: Humiliating Penetration and Degradation for this Sissy - Mistress Julia

xHamster 1 year ago

Ashley Santos Private Show

Ashley Santos Private Show

Flirt4Free 2 years ago

Kendal Smithx Private Show

HD 2:00 / 13:41

Kendal Smithx Private Show

Flirt4Free 2 weeks ago

The Whore Cellar of VaneSsaBiTCHx. My Future 🕳GLORyHoLe PariSChienneTrvprod91

The Whore Cellar of VaneSsaBiTCHx. My Future 🕳GLORyHoLe PariSChienneTrvprod91

xHamster 2 months ago

Sissy September

52% 0:14 / 24:05

Sissy September

Clips4sale 9 months ago

Sissy Walking Training

Sissy Walking Training

xHamster 9 months ago

Spunk PERVERSITY inside your SISSY's BOOTIE

Spunk PERVERSITY inside your SISSY's BOOTIE

TransTube.tv 1 year ago

Sissy in Pink Micro Bikini Butt-Chugging 1L of Beer on Your Table

Sissy in Pink Micro Bikini Butt-Chugging 1L of Beer on Your Table

xHamster 4 months ago

Hot TS Venus Lux trains newbie Javier LoveTongue with her raw cock

Hot TS Venus Lux trains newbie Javier LoveTongue with her raw cock

UrGayPorn 10 months ago

Your Step-Sister Sissy Trains You

61% HD 0:16 / 6:31

Your Step-Sister Sissy Trains You

Clips4sale 4 years ago

Weekley Sex Machine Piss Orgasm Anal Stretching Training Crossdresser Slut 23022023

Weekley Sex Machine Piss Orgasm Anal Stretching Training Crossdresser Slut 23022023

xHamster 3 years ago

Tied to sissy-teaching-machine at total speed Taught to comply any fellows

Tied to sissy-teaching-machine at total speed Taught to comply any fellows

TrannyGem 1 year ago

Big Ass Sissy First Double Anal Toy

Big Ass Sissy First Double Anal Toy

xHamster 2 years ago

An European, Brutus Roleplays.

An European, Brutus Roleplays.

Flirt4Free 11 years ago

Cute Small Dick Trans Raven Pissing After Intense Anal Riding and Massive Creampie Cumfarts

Cute Small Dick Trans Raven Pissing After Intense Anal Riding and Massive Creampie Cumfarts

xHamster 1 month ago

sissy dildo on wall tease

sissy dildo on wall tease

xHamster 3 years ago

Jill Pill: Dildo Throat Training

Jill Pill: Dildo Throat Training

xHamster 3 months ago

Turning My Boyfriend Into Girlfriend Femdom Sissy Boy Transformation Crossdressing

Turning My Boyfriend Into Girlfriend Femdom Sissy Boy Transformation Crossdressing

FapHouse 1 month ago

Valery Brett Private Show

Valery Brett Private Show

Flirt4Free 7 months ago

Robbie Edwards Private Show

Robbie Edwards Private Show

Flirt4Free 2 years ago

Femdom Girlfriend Won’t let me take out Plug untill She’s Creampied Trans Cum Interracial BBC Femboy

Femdom Girlfriend Won’t let me take out Plug untill She’s Creampied Trans Cum Interracial BBC Femboy

ShemaleSin 4 years ago

Busty Tranny Shows Off Her Dick While Getting Her Asshole Fucked

Busty Tranny Shows Off Her Dick While Getting Her Asshole Fucked

xHamster 3 years ago

Cumslut Training Session 3A

Cumslut Training Session 3A

ShemaleSin 5 years ago

Sissy Dolly's Dildo Gauntlet Gapes Her Slut Hole Raw Attempt 1

Sissy Dolly's Dildo Gauntlet Gapes Her Slut Hole Raw Attempt 1

JuicyTrans 1 day ago

Jade Venus, recently gave his office so hes had a private session

Jade Venus, recently gave his office so hes had a private session

Sheshaft 2 years ago

DominaFire Anal Training her Sissy With Glass Dildo

DominaFire Anal Training her Sissy With Glass Dildo

xHamster 3 years ago

Sissy coming home from work

Sissy coming home from work

aShemaleTube 8 months ago

Alexxa A Private Show

HD 2:00 / 11:22

Alexxa A Private Show

Flirt4Free 21 hours ago

becomingfemme - riley jay im tired of waiting and begging porn video

becomingfemme - riley jay im tired of waiting and begging porn video

TransDoe 1 year ago

Ts Diana Deelight teaches in a sissy

Ts Diana Deelight teaches in a sissy

TransTube.tv 1 year ago

Femboy soles taunt with ample plaything

Femboy soles taunt with ample plaything

TrannyGem 2 years ago

Gothic Witch screws 3 Xxl Fake Penises

Gothic Witch screws 3 Xxl Fake Penises

TrannyGem 3 years ago

trans female getting fucked from behind and lovin’ it

trans female getting fucked from behind and lovin’ it

TrannyGem 6 months ago

Tiny Demon Romped a She-creature Angel rock-hard in the BUTT

Tiny Demon Romped a She-creature Angel rock-hard in the BUTT

TransTube.tv 1 year ago

Addonis Smith & Huber Nicols Private Show

69% HD 2:00 / 8:56

Addonis Smith & Huber Nicols Private Show

Flirt4Free 1 year ago

Sissy trainer - You are sissy

Sissy trainer - You are sissy

TransTube.tv 1 year ago

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

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

TrannyGem 3 years ago

Dad plows Trap utter video

Dad plows Trap utter video

TrannyGem 3 years ago

That babe Gets The Cum Banged Out Of Her On All Fours 4K

That babe Gets The Cum Banged Out Of Her On All Fours 4K

ShemaleSin 1 year ago

Blowjob Ends with Cum in the Mouth

66% HD 2:00 / 19:15

Blowjob Ends with Cum in the Mouth

Flirt4Free 1 year ago

Sissy Elvi Lynx Anal Dildo Fucking

Sissy Elvi Lynx Anal Dildo Fucking

xHamster 3 weeks ago

Alpha & Beta Cum load Comparison - Fag Challenge - Slave Training

Alpha & Beta Cum load Comparison - Fag Challenge - Slave Training

xHamster 1 year ago

Dimitri Caruso Private Show

4K 2:00 / 14:57

Dimitri Caruso Private Show

Flirt4Free 1 year ago

Self-training No. 98: Standing Fuck Machine Masturbation

Self-training No. 98: Standing Fuck Machine Masturbation

xHamster 2 months ago

Sissy Wife Blowjob Practice - Clara Dee JOI

HD 1:01 / 15:05

Sissy Wife Blowjob Practice - Clara Dee JOI

FapHouse 2 years ago

dreamtranny - dany mineirinha doctor delivers a hand job to this hot tranny

dreamtranny - dany mineirinha doctor delivers a hand job to this hot tranny

TransDoe 2 years ago

Nothing Better Than an Outing in the Countryside in Corn Field to Do Yourself Good

Nothing Better Than an Outing in the Countryside in Corn Field to Do Yourself Good

xHamster 6 months ago

uber-cute she-creature plumbed rigid in the bootie by fuck-a-thon machine and jism no arms

uber-cute she-creature plumbed rigid in the bootie by fuck-a-thon machine and jism no arms

TrannyGem 4 years ago

Now Her Life Has Purpose

Now Her Life Has Purpose

xHamster 6 months ago

Sandy Nell Private Show

Sandy Nell Private Show

Flirt4Free 2 years ago

Charlie Cano Private Show

61% HD 2:00 / 5:11

Charlie Cano Private Show

Flirt4Free 3 years ago

INTERRACIAL HARDCORE TRAINING WITH BBC & LARGE BUTT LALIN GIRL TS KHLOE KHALIFA

INTERRACIAL HARDCORE TRAINING WITH BBC & LARGE BUTT LALIN GIRL TS KHLOE KHALIFA

ShemaleSin 4 weeks ago

Sissygasm from rectal getting off in sissy bi-atch with closed jewel in chastity_sc.twenty-one

Sissygasm from rectal getting off in sissy bi-atch with closed jewel in chastity_sc.twenty-one

TrannyGem 3 years ago

SISSY TRAINNING CUMMING SLUT COMPILATION

Premium HD 10:16

SISSY TRAINNING CUMMING SLUT COMPILATION

Sheer 11 months ago

Assfuck hoe instructing - hefty playthings and palms-free-for-all jizz shot

Assfuck hoe instructing - hefty playthings and palms-free-for-all jizz shot

TrannyGem 4 years ago

Love fuck myself

Love fuck myself

xHamster 5 months ago

BBC Ebony Dominatrix Mounts Her Kitten & Rides Until ANAL Fisting Blows Her Mind

BBC Ebony Dominatrix Mounts Her Kitten & Rides Until ANAL Fisting Blows Her Mind

Sheshaft 2 months ago

Liam Jacobson Private Show

Liam Jacobson Private Show

Flirt4Free 6 years ago

FEMDOM FISTING ANAL TRAINING PEGGING MASTIX DOMINATION FEMBOY

FEMDOM FISTING ANAL TRAINING PEGGING MASTIX DOMINATION FEMBOY

ShemaleSin 4 years ago

Sissy Training 24 - Use a Fuck Machine

Sissy Training 24 - Use a Fuck Machine

xHamster 1 year ago

TV crossdresser Monique - On the edge of a forest

TV crossdresser Monique - On the edge of a forest

xHamster 1 year ago

Isabella Pearson Private Show

Isabella Pearson Private Show

Flirt4Free 1 week ago

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