Training Videos - Trans (118,994)

Mommy ASS Fucking her FemBoy SISSY Crossdresser try hard Tranny Shemale with HUGE fake TITS and very Big Cock

Mommy ASS Fucking her FemBoy SISSY Crossdresser try hard Tranny Shemale with HUGE fake TITS and very Big Cock

XHamster 3 months ago

Bimbo Slut Training, Part 4: Anal Training - Goddess Lilith

61% HD 0:10 / 11:40

Bimbo Slut Training, Part 4: Anal Training - Goddess Lilith

LoyalFans 5 months ago

All that mouth training pays off : facefucking marvelous transwife Melody

All that mouth training pays off : facefucking marvelous transwife Melody

ShemaleSin 2 years ago

Trained and Dominated TV & TS

Trained and Dominated TV & TS

Tranny.one 4 years ago

TS Jasmine Lotus Spit Roasted and trained to a anal

TS Jasmine Lotus Spit Roasted and trained to a anal

IcePorn 1 week ago

Ryu Nymph Stretches her Arse with a Monster can

Ryu Nymph Stretches her Arse with a Monster can

TrannyGem 4 years ago

Sissy Institute Mistress Bailey Trains SISSYSLUTS - Lily DeMure + Nyxi Leon

Sissy Institute Mistress Bailey Trains SISSYSLUTS - Lily DeMure + Nyxi Leon

BeMyHole 5 years ago

Femboy stretches his hole with a big dildo

Femboy stretches his hole with a big dildo

XHamster 4 years ago

Trannies in training - (Episode #01)

Trannies in training - (Episode #01)

XHamster 9 months ago

Nasty swinger couples enjoy anal train

Nasty swinger couples enjoy anal train

Some.Porn 8 months ago

Hottest Cock Milking Ever

Hottest Cock Milking Ever

XHamster 6 months ago

Trans Lady trains you to suck dick, beginning gentle but then predominant you and fucking your face

Trans Lady trains you to suck dick, beginning gentle but then predominant you and fucking your face

MyTransfix 1 week ago

head and eyebrows shave for obedient slave

head and eyebrows shave for obedient slave

XHamster 2 years ago

Pegging femboy with massive strapon!

Pegging femboy with massive strapon!

EpicGFs 3 years ago

Sissy Joyce guides you through the ultimate chastity cage experience - A Tranny's guide to domination and humiliation!

Sissy Joyce guides you through the ultimate chastity cage experience - A Tranny's guide to domination and humiliation!

TrannyMovs 11 months ago

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

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

XHamster 6 months ago

Sissy Trained And Owned By BIG BLACK PENIS Bull

Sissy Trained And Owned By BIG BLACK PENIS Bull

Analdin 4 years ago

Your Futa Anal Trainer guides you through TOUGH FUTA SESSION [SAMPLE]

Your Futa Anal Trainer guides you through TOUGH FUTA SESSION [SAMPLE]

Eporner 1 year ago

TOTK-010 Shemale cock is hard!! Restraint training anal FUCK Shiori Hirate - Shiho

TOTK-010 Shemale cock is hard!! Restraint training anal FUCK Shiori Hirate - Shiho

Eporner 1 month ago

Master trains his sissy in -Censored- He uses her mouth a

Master trains his sissy in -Censored- He uses her mouth a

FetishShrine 2 months ago

Feminization Sissification Sissy Threesome Training Blowjob

Feminization Sissification Sissy Threesome Training Blowjob

BeMyHole 1 year ago

It’s Just Curiosity, Right? Confused? Not Anymore

58% 0:38 / 14:00

It’s Just Curiosity, Right? Confused? Not Anymore

Clips4sale 7 months ago

Playtime 69

XHamster 9 months ago

TRANSSEXUAL Sissy Super-Bitch Raunchy Pound inbetween Honeypot and Weenie

TRANSSEXUAL Sissy Super-Bitch Raunchy Pound inbetween Honeypot and Weenie

TrannyGem 5 years ago

Deep training final, 19 inch long anal ball toy

Deep training final, 19 inch long anal ball toy

XHamster 4 years ago

Ginger tgirl edging & blowjob training💗

Ginger tgirl edging & blowjob training💗

AShemaleTube 1 year ago

Feminized and Love It -- You Will Too

Feminized and Love It -- You Will Too

TrannyGem 4 years ago

Femboy Viii punished

Femboy Viii punished

Transvids.tv 1 year ago

Sissy Jessica Bloom Teaches You How To Suck Cock And Swallow Cum

Sissy Jessica Bloom Teaches You How To Suck Cock And Swallow Cum

XHamster 1 year ago

Sissy in shiny bodystocking Using Fuck Machine - R..a..c..h..a..e..l B..e..l..l..e

Sissy in shiny bodystocking Using Fuck Machine - R..a..c..h..a..e..l B..e..l..l..e

PornoXO 9 months ago

GETTING RID OF MY SEX TOY

GETTING RID OF MY SEX TOY

AShemaleTube 4 months ago

Becoming Anal Slut Training For Newbies

Becoming Anal Slut Training For Newbies

BeMyHole 4 years ago

Trans Slut Gets Trained To Become Puppy Slapped And Humiliated Short

Trans Slut Gets Trained To Become Puppy Slapped And Humiliated Short

BeMyHole 3 years ago

Sissy Dreams - 3 (eng)

Sissy Dreams - 3 (eng)

XXXShemalePorn 11 years ago

Experienced shemale training her Sissy friend @ BeautizOnCam

Experienced shemale training her Sissy friend @ BeautizOnCam

AShemaleTube 4 years ago

Sissy Slut Trained and Spit Roasted

Sissy Slut Trained and Spit Roasted

Pornwhite 1 year ago

Anal Training That Will Make You Squirm

Anal Training That Will Make You Squirm

AShemaleTube 5 years ago

Trans gets Manacled and Jammed by Hefty Lollipop

Trans gets Manacled and Jammed by Hefty Lollipop

TrannyGem 3 years ago

Serving Mr. Maxxx (thad Fucks Brie Lovely and Ryley Rails)

Serving Mr. Maxxx (thad Fucks Brie Lovely and Ryley Rails)

ShemaleSex 2 weeks ago

Mitsuha's Anal Sex Training

Mitsuha's Anal Sex Training

XHamster 1 year ago

Shemale Training Her Sissy Friend.. Who May Become One Of Them

Shemale Training Her Sissy Friend.. Who May Become One Of Them

GetTranny 3 years ago

2032 - the Bwno Future

2032 - the Bwno Future

XHamster 10 months ago

Wifey Taunts you about locking you in innocence like her TRANSSEXUAL Buddy POINT OF VIEW HAND JOB SISSY TEACHING

Wifey Taunts you about locking you in innocence like her TRANSSEXUAL Buddy POINT OF VIEW HAND JOB SISSY TEACHING

TrannyGem 5 years ago

Lola Crystals (TrulyByL) gets BIG BLACK COCK special from Ali Da Reaper on Dark-hued Friday

Lola Crystals (TrulyByL) gets BIG BLACK COCK special from Ali Da Reaper on Dark-hued Friday

TransTube.tv 1 year ago

Sissy Fuckdoll Delivery

Sissy Fuckdoll Delivery

TransTube.tv 1 year ago

G094 - Back to Back Swallows!

72% HD 0:39 / 4:38

G094 - Back to Back Swallows!

FapHouse 7 months ago

Training Sissy Throat and Pussy 3

Training Sissy Throat and Pussy 3

BoyFriendTV 11 months ago

Cock Worship Boy Training

Cock Worship Boy Training

Tranny.one 3 years ago

Cumming while fucking

Cumming while fucking

XHamster 3 years ago

Patiently Waiting for Her Man

Patiently Waiting for Her Man

XHamster 8 months ago

Double Stuffed w Girl Cock feat Ava Venom & Giselle Driller

76% 0:25 / 12:06

Double Stuffed w Girl Cock feat Ava Venom & Giselle Driller

Clips4sale 1 year ago

2 Mommies Training Their TS Slut - Lucy Hart - Penny Barber - Mira Maven

2 Mommies Training Their TS Slut - Lucy Hart - Penny Barber - Mira Maven

XHamster 1 year ago

A Dominant Granny Trains These Little Whores

A Dominant Granny Trains These Little Whores

XHamster 8 months ago

Instructing Your Sissy

Instructing Your Sissy

TransTube.tv 1 month ago

CHASTITY slave CUMS while PEGGING after training with some XXL toys

CHASTITY slave CUMS while PEGGING after training with some XXL toys

XHamster 1 year ago

Rianna James teaches you how to worship her ass with a kinky twist

Rianna James teaches you how to worship her ass with a kinky twist

TrannyMovs 7 months ago

Between the Lines & Between My Legs

Between the Lines & Between My Legs

XHamster 9 months ago

Wifey Instructs Flawless Bi-Atch for her Hubby. Me, A Sissy.

Wifey Instructs Flawless Bi-Atch for her Hubby. Me, A Sissy.

TrannyGem 5 years ago

Sissy Kate learns how to use the anal fucking machine with Lisa

Sissy Kate learns how to use the anal fucking machine with Lisa

XHamster 2 years ago

Mistress fingering and giving prostate massage to her Sissy

Mistress fingering and giving prostate massage to her Sissy

XHamster 6 months ago

Long machine for worn out crossdresser anal

Long machine for worn out crossdresser anal

XHamster 1 year ago

Sissy motivation,sissy teaching,sissy biotch

Sissy motivation,sissy teaching,sissy biotch

TrannyGem 8 months ago

ME WAS SO RANDY THAT ME MASTURBATED AMID THE MIDDLE BELONGING WAXING AND FILLED EVERYTHING ACCOMPANYING MINE WARM SEMEN.

ME WAS SO RANDY THAT ME MASTURBATED AMID THE MIDDLE BELONGING WAXING AND FILLED EVERYTHING ACCOMPANYING MINE WARM SEMEN.

WebcamBros 1 year ago

TS Anna Katt Prepares Lily's Ass for Cock

TS Anna Katt Prepares Lily's Ass for Cock

TrannyGem 7 years ago

thirty minutes no break deepthroat spitroast defiance!

thirty minutes no break deepthroat spitroast defiance!

ShemaleSin 3 years ago

Natalie Mars In Training The Little-gimp#2

Natalie Mars In Training The Little-gimp#2

AbTranny 2 years ago

Crossdressing fucked in the butt

Crossdressing fucked in the butt

MyTransfix 2 months ago

Two dominating girlfriends and fucking a common sissy slut

Two dominating girlfriends and fucking a common sissy slut

XHamster 1 year ago

Training day 04 - 2023-02-21 - quite the fulfilled day

Training day 04 - 2023-02-21 - quite the fulfilled day

XHamster 3 years ago

The slave girl fixed in the ground pillory

The slave girl fixed in the ground pillory

XHamster 8 months ago

louise88 best sissy training ever

louise88 best sissy training ever

AShemaleTube 5 years ago

Humiliating Cock Sucking Training for Sissy

Humiliating Cock Sucking Training for Sissy

Tranny.one 4 years ago

Obedience Training With Kendall Penny

Obedience Training With Kendall Penny

Nuvid 6 months ago

LUCA FERRERO TRAINS HIS TRANNY

LUCA FERRERO TRAINS HIS TRANNY

Eporner 11 months ago

W*A*A*A- 223 Masochistic Trans Boy and Lesbian Slut - Female Orgasmic Erotic Anal FUCK - Mao Hamasaki, Yui Hatano, Chibitori Decensored

W*A*A*A- 223 Masochistic Trans Boy and Lesbian Slut - Female Orgasmic Erotic Anal FUCK - Mao Hamasaki, Yui Hatano, Chibitori Decensored

Eporner 1 year ago

Feminization Sissification Sissy training - BE ENSLAVED FAG

Feminization Sissification Sissy training - BE ENSLAVED FAG

TransTube.tv 1 year ago

White Sissy Floozy Gets Mouth DESTROYED & dominated By Uncut TS BBC GIANT LOAD TS Carmen Masters

White Sissy Floozy Gets Mouth DESTROYED & dominated By Uncut TS BBC GIANT LOAD TS Carmen Masters

ShemaleSin 5 months ago

Sissy Slave - Gf Lindse Is Training Her To Suck And Take Dick How Humiliatting (1440)

Sissy Slave - Gf Lindse Is Training Her To Suck And Take Dick How Humiliatting (1440)

AbTranny 4 weeks ago

Lucas's Bi Slave Training

Lucas's Bi Slave Training

BeMyHole 2 years ago

Feminization Sissification Sissy three-some training oral-job

Feminization Sissification Sissy three-some training oral-job

ShemaleSin 2 years ago

Emily Adaire gets a helping hand to open up her pinkish crevice - Trailer

Emily Adaire gets a helping hand to open up her pinkish crevice - Trailer

TransTube.tv 2 years ago

Deepthroat Training While Hard Like A Good Trans Girl S

Deepthroat Training While Hard Like A Good Trans Girl S

Eporner 1 year ago

Futa teaches you to take two in the ass. Double anal penetration training part 2 [Sample Version]

Futa teaches you to take two in the ass. Double anal penetration training part 2 [Sample Version]

Eporner 3 months ago

Tgirl Sasha De Sade - Advanced Slut Training

Tgirl Sasha De Sade - Advanced Slut Training

GetTranny 3 years ago

Who wants to be a real Sissy bitch

Who wants to be a real Sissy bitch

AShemaleTube 4 years ago

Petra the little pink whore

Petra the little pink whore

ShemaleSin 3 months ago

Training The Secretary

Training The Secretary

AShemaleTube 1 week ago

Bound Orgasms and Anal in Sundresses and Ropes Ft Aerie Rei

Bound Orgasms and Anal in Sundresses and Ropes Ft Aerie Rei

XHamster 1 month ago

Slave Training

XHamster 4 years ago

Rigid Ass-Fuck Penetrate - Sissy - Female Dominance

Rigid Ass-Fuck Penetrate - Sissy - Female Dominance

TrannyGem 4 years ago

Petite Trans Kawaii Fiona Fucks a Submissive Trans Puppy-Girl

Petite Trans Kawaii Fiona Fucks a Submissive Trans Puppy-Girl

XHamster 1 year ago

Mistress Trains Slave To Take Cock

Mistress Trains Slave To Take Cock

BeMyHole 1 year ago

Sissy Sucks Alpha's Wang and Takes a Smutty Facial during the time that Female-Dominant Whispers Encouragement

Sissy Sucks Alpha's Wang and Takes a Smutty Facial during the time that Female-Dominant Whispers Encouragement

ShemaleSin 5 years ago

A Girl Is Going to Get Her Ass Fisted

A Girl Is Going to Get Her Ass Fisted

ShemaleSex 3 weeks ago

Sissy Anal Training

Sissy Anal Training

AShemaleTube 6 years ago

Sui Mizumori Riku Mukai, A Beautiful Female Teacher Who Is Excited About The Transvestite Habits Of Her Students And Trains Her Pets

Sui Mizumori Riku Mukai, A Beautiful Female Teacher Who Is Excited About The Transvestite Habits Of Her Students And Trains Her Pets

Eporner 1 year ago

Ex-Twitch Star Gaming As Usual

Ex-Twitch Star Gaming As Usual

Eporner 2 weeks ago

ryu Girl wedges dragon nut sack, pony fuck stick and monster can

ryu Girl wedges dragon nut sack, pony fuck stick and monster can

TrannyGem 3 years ago

Transsexual training - bukkake gokkun! Shemale anal fuck orgy

Transsexual training - bukkake gokkun! Shemale anal fuck orgy

XHamster 1 year ago

Petra back in the boom room

Petra back in the boom room

XHamster 10 months ago

Feminization Instructing to Turn You into a Obedient Sissy Foolish #0

Feminization Instructing to Turn You into a Obedient Sissy Foolish #0

TrannyGem 3 weeks ago

Transformed husband into a slut and four more cocks and two dominatrixes

Transformed husband into a slut and four more cocks and two dominatrixes

XHamster 2 years ago

CUM SISSY TRAINING

CUM SISSY TRAINING

AShemaleTube 1 month ago

Mistress Flo Fists the Ass of Two Mature Transvestites

Mistress Flo Fists the Ass of Two Mature Transvestites

XHamster 8 months ago

A trans gostosa emyfibmaB anal training session

A trans gostosa emyfibmaB anal training session

Eporner 1 year ago

Training the 18 yrs boy slut from Iowa

Training the 18 yrs boy slut from Iowa

AShemaleTube 4 years ago

Stretching and wrecking a femboy's asshole (full video on OF or Fansly)

Stretching and wrecking a femboy's asshole (full video on OF or Fansly)

XHamster 2 years ago

how to use a fufu pinch

how to use a fufu pinch

TrannyGem 2 years ago

Chastity cage after a week of sissy training, dreaming of a daddy's cock

Chastity cage after a week of sissy training, dreaming of a daddy's cock

XHamster 3 years ago

Spandex Sissy Punished by V-Card Fuckmachine Smacking Dickblowing Pegging by Domina Mercer

Spandex Sissy Punished by V-Card Fuckmachine Smacking Dickblowing Pegging by Domina Mercer

TrannyGem 4 years ago

GONZO - Senso Unico Peccati Trans Italiani

GONZO - Senso Unico Peccati Trans Italiani

TrannyGem 6 years ago

Sex Training

XHamster 6 months ago

TRANSSEXUAL Sissy Jism Hoe Extraordinary Face Pummel

TRANSSEXUAL Sissy Jism Hoe Extraordinary Face Pummel

TrannyGem 5 years ago

Trained and Dominated TV & TS

Trained and Dominated TV & TS

Tranny.one 4 years ago

Girls playing before going out

Girls playing before going out

XHamster 2 years ago

Chained Innocence Sissy Marionette takes Supah-Sized Faux-Cock and female dominance Spandex Going Knuckle Deep by Domina Mercer

Chained Innocence Sissy Marionette takes Supah-Sized Faux-Cock and female dominance Spandex Going Knuckle Deep by Domina Mercer

TrannyGem 9 months ago

Sissy Training by Queen Daralis Part 2

52% HD 1:01 / 7:16

Sissy Training by Queen Daralis Part 2

FapHouse 6 months ago

Thick Cock Charlotte Sins Lesbian In Training

Thick Cock Charlotte Sins Lesbian In Training

BeMyHole 1 month ago

Ball-Gagged Sissy Hoe phat Belt Cock Pegging by little female dominance Princess in Spandex apparel by Domme Mercer

Ball-Gagged Sissy Hoe phat Belt Cock Pegging by little female dominance Princess in Spandex apparel by Domme Mercer

TrannyGem 3 years ago

Miss Abernathys Maid training

Miss Abernathys Maid training

AShemaleTube 10 months ago

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