Training Videos - Trans (119,347)

Sissy Slut Adventures Volume 1

Sissy Slut Adventures Volume 1

Pornzona 2 weeks ago

Sissy teasing in shiny leggings and new inverted chastity

Sissy teasing in shiny leggings and new inverted chastity

XHamster 10 months ago

Amber Mei Neil - Sissy CD Deep Facehole & Face Smashed Instructing Compilation

Amber Mei Neil - Sissy CD Deep Facehole & Face Smashed Instructing Compilation

TrannyGem 5 years ago

Top 10 Femdom Ideas 2022

Top 10 Femdom Ideas 2022

XHamster 2 years ago

Caged Sissy Cums with Inverted Chastity Still On

Caged Sissy Cums with Inverted Chastity Still On

XHamster 6 months ago

A ultra-nasty chick strokes as soon as she gets home????chinese crossdresser getting off

A ultra-nasty chick strokes as soon as she gets home????chinese crossdresser getting off

Transvids.tv 1 year ago

Anal Update two: Princess Edition!

Anal Update two: Princess Edition!

ShemaleSin 1 year ago

Sissy pegs her caged balls

Sissy pegs her caged balls

ShemaleSin 2 days ago

Femboy with black nails pounds gaping ass and cums from riding a dildo

Femboy with black nails pounds gaping ass and cums from riding a dildo

XHamster 1 year ago

GAY for WHITE Dicks

55% 0:27 / 14:11

GAY for WHITE Dicks

Clips4sale 1 year ago

sentindo no pelo o cuzinho delicioso da Solzinha

Premium HD 21:44

sentindo no pelo o cuzinho delicioso da Solzinha

XNXXGold 6 months ago

Alexxa & Francesco Private Show

55% HD 2:00 / 4:56

Alexxa & Francesco Private Show

Flirt4Free 3 years ago

Femboy in chastity belt gets fucked so hard his bussy drips cum until he screams

Femboy in chastity belt gets fucked so hard his bussy drips cum until he screams

GayPornWatch 6 days ago

Trans Slut Will Receive Anal Training From a Dominant Woman

Trans Slut Will Receive Anal Training From a Dominant Woman

XHamster 7 months ago

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

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

429Men 5 months ago

Bondage Sissy Bitch - 720HD

Bondage Sissy Bitch - 720HD

Clips4sale 3 years ago

Your Thanksgiving hole stuffed by a Futa MILF for the first time

Your Thanksgiving hole stuffed by a Futa MILF for the first time

AveXXX 2 weeks ago

blowing pricks compliation and getting a facial cumshot

blowing pricks compliation and getting a facial cumshot

TransTube.tv 1 year ago

NA055 Two mistress , training slave and riding on his face -双女王-调教奴隶,拘束,剃毛,颜面骑乘,虐屌,惨叫

NA055 Two mistress , training slave and riding on his face -双女王-调教奴隶,拘束,剃毛,颜面骑乘,虐屌,惨叫

AShemaleTube 6 years ago

Sissy cosplay anal Chinese femboy destroyed on camera

Sissy cosplay anal Chinese femboy destroyed on camera

JuicyTrans 6 days ago

Sissy armpit worship ruined her nipples while crossdresser fucked her raw

Sissy armpit worship ruined her nipples while crossdresser fucked her raw

JuicyTrans 4 weeks ago

I squirted by doing some anal training and get up to 6 pumps

I squirted by doing some anal training and get up to 6 pumps

Pornzona 1 week ago

Creaming on my new dildo

Creaming on my new dildo

XHamster 4 years ago

PARTICULAR: Bloopers and Deleted Scenes of Anal Gaped Femboy in Cosplay Screwing His Booty and Jerking Off Until this babe Cums

PARTICULAR: Bloopers and Deleted Scenes of Anal Gaped Femboy in Cosplay Screwing His Booty and Jerking Off Until this babe Cums

ShemaleSin 3 months ago

Sexy Gal Screws Tranny Booty Until This guy Cums!!!

Sexy Gal Screws Tranny Booty Until This guy Cums!!!

ShemaleSin 1 year ago

Italian Sissy Gaped Raw by Huge Dildo Then Explodes Cum Gush

Italian Sissy Gaped Raw by Huge Dildo Then Explodes Cum Gush

JuicyTrans 3 months ago

The Tutor E01 Showing a Virgin the Ropes - MILF Stella

71% HD 0:39 / 41:15

The Tutor E01 Showing a Virgin the Ropes - MILF Stella

FapHouse 2 years ago

THE TRAINING OF MY TS SERF ANGEL

THE TRAINING OF MY TS SERF ANGEL

ShemaleSin 5 years ago

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

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

Pornzona 4 months ago

Sissy caught with dancing dildo outdoors seduces the voyeur

Sissy caught with dancing dildo outdoors seduces the voyeur

JuicyTrans 1 month ago

Sophia Loreen Private Show

4K 2:00 / 10:47

Sophia Loreen Private Show

Flirt4Free 1 week ago

Sissy boi gets his cock & balls pulled whilst his ass being pounded

Sissy boi gets his cock & balls pulled whilst his ass being pounded

XHamster 2 years ago

SisK play with her clitty whilst watching porn

SisK play with her clitty whilst watching porn

ShemaleSin 1 week ago

My sex tool makes me squirt and discharges cum in my obese booty

My sex tool makes me squirt and discharges cum in my obese booty

ShemaleSin 4 months ago

FLUNY FAGGOT PROFESSOR

HD 0:10 / 10:51

FLUNY FAGGOT PROFESSOR

LoyalFans 3 years ago

Edging My Sissy Slut With A Fleshlight (He Begs To Cum)

Edging My Sissy Slut With A Fleshlight (He Begs To Cum)

Pornfact 1 day ago

Charlie Cano Private Show

67% HD 2:00 / 15:20

Charlie Cano Private Show

Flirt4Free 3 years ago

Glasses Pressed to Your Forehead - Asmr Into My Femme Clip by Findom Goaldigger

Glasses Pressed to Your Forehead - Asmr Into My Femme Clip by Findom Goaldigger

XHamster 8 months ago

Sissy Booty Bitch Pt2 Preview

Sissy Booty Bitch Pt2 Preview

ShemaleSin 3 years ago

Anabelle and Brianna - Stepmom and Auntie Make Beta Wear a Dress

49% 0:45 / 9:13

Anabelle and Brianna - Stepmom and Auntie Make Beta Wear a Dress

Clips4sale 2 years ago

Sissy rides BBC until cum drips from every hole

Sissy rides BBC until cum drips from every hole

JuicyTrans 1 month ago

Trans Sissy Floozy disciplined by Mistresse Murmur compilation

Trans Sissy Floozy disciplined by Mistresse Murmur compilation

BigTitsLust 7 months ago

Routine Inspection Pt 1

66% HD 0:26 / 11:42

Routine Inspection Pt 1

Clips4sale 1 year ago

A horny bitch riding a huge dildo experienced her first sissygasm, squirted massively and sucked all fluid and cum from herself

A horny bitch riding a huge dildo experienced her first sissygasm, squirted massively and sucked all fluid and cum from herself

XHamster 10 months ago

Sissy Intro at home and pleasing BBC Dildo

Sissy Intro at home and pleasing BBC Dildo

AShemaleTube 1 year ago

Jessica Kat Gets a Handjob During the Tennis Endurance Training

49% 0:30 / 13:28

Jessica Kat Gets a Handjob During the Tennis Endurance Training

Clips4sale 1 year ago

Fag Instructing Princess domme ❤️?

Fag Instructing Princess domme ❤️?

Transvids.tv 9 months ago

Edging JOI Ryley Rails

65% HD 0:39 / 5:27

Edging JOI Ryley Rails

FapHouse 7 months ago

Sissy Is Punished

Sissy Is Punished

FapHouse 2 years ago

Sissy Femboy Slavery Feminization Training

Sissy Femboy Slavery Feminization Training

ShemaleSin 1 year ago

A Show in My Native Language :)

A Show in My Native Language :)

Flirt4Free 4 months ago

sissy ass training woman penetrates husband in the ass PEGGING #88

sissy ass training woman penetrates husband in the ass PEGGING #88

Pornfact 2 weeks ago

Trans girl does extreme deepthroat training while in bondage Clip 1

Trans girl does extreme deepthroat training while in bondage Clip 1

XHamster 8 months ago

Roxy Park Private Show

HD 2:00 / 17:37

Roxy Park Private Show

Flirt4Free 2 years ago

On-the-job Training: Shemale hentai Jenny Cums A Biggest Load in My Throat Beneath Coffee Counter

On-the-job Training: Shemale hentai Jenny Cums A Biggest Load in My Throat Beneath Coffee Counter

ShemaleSin 9 months ago

Sexy Jade, Chad Rock

HD 1:01 / 39:54

Sexy Jade, Chad Rock

FapHouse 1 year ago

Feminization with chastity cage - task

Feminization with chastity cage - task

Clips4sale 4 years ago

Sophia Loreen Private Show

66% 4K 2:00 / 5:10

Sophia Loreen Private Show

Flirt4Free 1 year ago

Dimitri Caruso Private Show

4K 2:00 / 14:56

Dimitri Caruso Private Show

Flirt4Free 1 year ago

An Obedient Pet

An Obedient Pet

XHamster 6 months ago

DIAPER and PISS ENEMA treatment for SISSY husband

DIAPER and PISS ENEMA treatment for SISSY husband

Pornfact 3 months ago

I Love Lucy. Essex Girl Lisa catches Spike Watching Pegging Porn So She Feminises Him

I Love Lucy. Essex Girl Lisa catches Spike Watching Pegging Porn So She Feminises Him

Pornzona 4 months ago

Alejandra Fox Private Show

HD 2:00 / 11:51

Alejandra Fox Private Show

Camster 3 weeks ago

Training The Boot Slave

Training The Boot Slave

Clips4sale 1 year ago

”Those are five nasty creampies!”

”Those are five nasty creampies!”

TransHero 6 months ago

Sissy slave fuck and piss comp.

Sissy slave fuck and piss comp.

XHamster 1 year ago

Japanese mistress set your sissy goals to embrace feminization - JOI ROLEPLAY

Japanese mistress set your sissy goals to embrace feminization - JOI ROLEPLAY

XHamster 1 year ago

Prove me that you want my futa cock - JOI

Prove me that you want my futa cock - JOI

Clips4sale 2 years ago

She Is Going to Punish This Submissive Brat and Give Her a Red Ass

HD 0:39 / 19:41

She Is Going to Punish This Submissive Brat and Give Her a Red Ass

FapHouse 7 months ago

Slut flows and drips Queen of Precum 3

Slut flows and drips Queen of Precum 3

Pornzona 1 week ago

Im Gonna Turn You Into a Cocksucker and Put You on the Street Sissy Boi Shemale Version

Im Gonna Turn You Into a Cocksucker and Put You on the Street Sissy Boi Shemale Version

XHamster 1 month ago

SISSY TRAINNING by TWO DICKS

Premium HD 8:04

SISSY TRAINNING by TWO DICKS

XNXXGold 1 year ago

SKINNY SUBMISSIVE LADYBOY SELF ANAL FISTING AND SLAVE TRAINING

Premium HD 24:01

SKINNY SUBMISSIVE LADYBOY SELF ANAL FISTING AND SLAVE TRAINING

Sheer 1 year ago

Crossdresser in spandex catsuit practices sucking cock with a dildo

Crossdresser in spandex catsuit practices sucking cock with a dildo

XHamster 3 years ago

Travesti safada fica se alisando na pausa do trabalho mostrando seu cl&iacute_toris

Premium HD 10:01

Travesti safada fica se alisando na pausa do trabalho mostrando seu cl&iacute_toris

XNXXGold 1 week ago

Truth or Dare Game Turns Wild with the Bros!

Truth or Dare Game Turns Wild with the Bros!

XPornPlay 5 months ago

Bedtime for Sissy Taylor

Bedtime for Sissy Taylor

XHamster 5 months ago

Dirty Anal Training. CENSORED! Something was blocking my tight asshole but in the end I took it all.

Dirty Anal Training. CENSORED! Something was blocking my tight asshole but in the end I took it all.

Pornfact 2 weeks ago

STICKY n SWEET: Black Couples Motivation

STICKY n SWEET: Black Couples Motivation

AShemaleTube 9 years ago

Training Session, Cock Lifting and Hairy Armpits

Training Session, Cock Lifting and Hairy Armpits

AShemaleTube 1 month ago

Bondage blowjob training

Bondage blowjob training

XHamster 2 months ago

Homemade sissy training strapon madam reads the newspaper

Homemade sissy training strapon madam reads the newspaper

XHamster 1 year ago

My Femboy Roommate #1 - Helping My Femboy Lover Moving Into Our New Flat

My Femboy Roommate #1 - Helping My Femboy Lover Moving Into Our New Flat

XHamster 7 months ago

Sandy Lee Private Show

HD 2:00 / 14:58

Sandy Lee Private Show

Camster 10 years ago

You're only good for eating my BBC bull's cum and drinking ALL my piss!

You're only good for eating my BBC bull's cum and drinking ALL my piss!

Pornzona 1 week ago

Alejandra Fox Private Show

Alejandra Fox Private Show

Flirt4Free 4 years ago

jumping on a rubber knob aleksa Fantasies

jumping on a rubber knob aleksa Fantasies

ShemaleSin 2 months ago

Shemale Porn Video Lucas's Bi Slave Training

Shemale Porn Video Lucas's Bi Slave Training

Tranny.one 1 year ago

Sexy redhead tranny trains her ass for painal

Sexy redhead tranny trains her ass for painal

AShemaleTube 1 year ago

Allie North fresh toys

Allie North fresh toys

ShemaleSin 2 days ago

Sophia Loreen Private Show

HD 2:00 / 15:44

Sophia Loreen Private Show

Camster 3 weeks ago

Sissy Slut Adventures Volume 2

Sissy Slut Adventures Volume 2

Pornzona 2 weeks ago

Asian Sissy Femboy Training In Public

Asian Sissy Femboy Training In Public

Eporner 5 months ago

Sissy Bunny Training

HD 0:39 / 13:05

Sissy Bunny Training

FapHouse 1 year ago

Skitty in The Hypnogasm (Long)

Skitty in The Hypnogasm (Long)

XHamster 4 years ago

Sissy with flat chastity and highheels is fucked hard

Sissy with flat chastity and highheels is fucked hard

XHamster 1 year 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

Anal training with huge pump up butt plug

Anal training with huge pump up butt plug

Pornfact 2 weeks ago

Lick Cummies Movie

Lick Cummies Movie

Transvids.tv 1 year ago

SLIM LADYBOY ANAL CASTING, THRALL TRAINING AND CREAM ENEMA

SLIM LADYBOY ANAL CASTING, THRALL TRAINING AND CREAM ENEMA

ShemaleSin 1 year ago

[ Full Version ] Serve My Ladyboy Friend 2 ft Mari Ayanami

65% HD 0:30 / 54:29

[ Full Version ] Serve My Ladyboy Friend 2 ft Mari Ayanami

Clips4sale 8 months ago

Trans Mistress Trains Your Throat & Ass at Sissy School

63% 0:30 / 11:13

Trans Mistress Trains Your Throat & Ass at Sissy School

Clips4sale 1 year ago

Spanish audio rol JOI. They feminize you in a public bathroom. Obey!

Spanish audio rol JOI. They feminize you in a public bathroom. Obey!

XHamster 3 months ago

The Making Of A Sissy

HD 0:22 / 10:10

The Making Of A Sissy

IWantClips 1 month ago

Beg for his big cock like a good sissy boy

Beg for his big cock like a good sissy boy

XHamster 11 years ago

Feminized and Love It -- You Will Too

Feminized and Love It -- You Will Too

Pornzona 3 months ago

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

55% HD 0:39 / 47:11

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

FapHouse 7 months ago

Big Model Muscled Bodybuilder Flexing Show

43% HD 2:00 / 10:24

Big Model Muscled Bodybuilder Flexing Show

Flirt4Free 10 years ago

Sissy coming home from work

Sissy coming home from work

2BGay 11 months ago

Sissy Dreamland - Femdom Mistress pegs submissive femboy sluts ass doggy style with a BBC! Pegging cuck Part 3

Sissy Dreamland - Femdom Mistress pegs submissive femboy sluts ass doggy style with a BBC! Pegging cuck Part 3

XHamster 1 year ago

Accomplishments in your Mistress's name [1080p, mp4]

71% HD 0:14 / 10:03

Accomplishments in your Mistress's name [1080p, mp4]

Clips4sale 3 years ago

Cute Trans Teen Struggles in Bondage

Cute Trans Teen Struggles in Bondage

FapHouse 4 months ago

Training the Slut Inside You: Mesmerizing HFO [Erotic ASMR] [Training Series Part 2]

Training the Slut Inside You: Mesmerizing HFO [Erotic ASMR] [Training Series Part 2]

Pornzona 1 month ago

Sissy gets wedgie in public park

Sissy gets wedgie in public park

Pornzona 4 days ago

The Truth About Your Waiters

The Truth About Your Waiters

Some.Porn 10 months ago

Look what happened in this room, among those trans cuties.

Look what happened in this room, among those trans cuties.

ShemaleSin 2 years ago

Femmes Pub Gig six: A Sissy Feminization Series

Femmes Pub Gig six: A Sissy Feminization Series

TrannyGem 5 years ago

Dirty Mistress Sissy JOI Training Jerk Off Instruction by Iskra Electrical Clip 1

Dirty Mistress Sissy JOI Training Jerk Off Instruction by Iskra Electrical Clip 1

XHamster 9 months ago

Cuckold, sph, degrading, hot wife!

Cuckold, sph, degrading, hot wife!

XHamster 7 months ago

large collection of all femboy anal penetrations from 2025.

large collection of all femboy anal penetrations from 2025.

ShemaleSin 6 months ago

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