Training Videos - Trans (87,075)

Latex Domination and Sissy Training

Latex Domination and Sissy Training

KeekAss 1 week ago

Sissy Maid Training Stage 1 (WMV)

Sissy Maid Training Stage 1 (WMV)

Clips4sale 2 years ago

Tranny Loves Cock And Cum (MP4)

HD 0:12 / 16:25

Tranny Loves Cock And Cum (MP4)

Clips4sale 4 years ago

”GENDER X TS cheerleader rides on big black cock - Smash Thompson,Ella Hollywood”

”GENDER X TS cheerleader rides on big black cock - Smash Thompson,Ella Hollywood”

TransHero 4 years ago

GIGANTIC Ding-Dong Pegging for Chastity Sissy Thrall Destroying her Sexually Excited Gap by Mastix Mercer

GIGANTIC Ding-Dong Pegging for Chastity Sissy Thrall Destroying her Sexually Excited Gap by Mastix Mercer

ShemaleSin 4 years ago

Anny Belly Private Show

HD 2:00 / 40:24

Anny Belly Private Show

Flirt4Free 3 years ago

Femdoms Spank and Peg Crossdresser Sissy

Femdoms Spank and Peg Crossdresser Sissy

Some.Porn 1 year ago

Charlie Cano Private Show

HD 2:00 / 27:25

Charlie Cano Private Show

Flirt4Free 3 years ago

Sissy Training by Queen Daralis Part 1

Sissy Training by Queen Daralis Part 1

FapHouse 3 weeks ago

I cum hands free bouncing on a 7inch dildo while my small cock flops with excitement

I cum hands free bouncing on a 7inch dildo while my small cock flops with excitement

xHamster 2 years ago

Sissy Cocksucker gets Slapped on her Big Puffy Lactating Nipples

Sissy Cocksucker gets Slapped on her Big Puffy Lactating Nipples

xHamster 4 months ago

Deepthroat Training Absolute Control

Deepthroat Training Absolute Control

FapHouse 1 month ago

who wants to play with my nipples?

who wants to play with my nipples?

xHamster 1 year ago

WRAP YOUR LIPS AROUND COCK

70% HD 0:10 / 16:17

WRAP YOUR LIPS AROUND COCK

LoyalFans 3 years ago

Sucking Cock Training Session

Sucking Cock Training Session

aShemaleTube 1 month ago

Even More Chilling Out with Some Porn..

Even More Chilling Out with Some Porn..

xHamster 9 months ago

Big Booty Femboy Cock Lover Desperately Anal Fucking Herself

Big Booty Femboy Cock Lover Desperately Anal Fucking Herself

xHamster 3 weeks ago

Bathing with stockings and thong

Bathing with stockings and thong

xHamster 2 years ago

8. bi-slave-gang-bang part 3 - anal explosion and mega cumshot

55% HD 1:01 / 6:31

8. bi-slave-gang-bang part 3 - anal explosion and mega cumshot

FapHouse 4 years ago

Play Ass Holes

67% HD 2:00 / 15:28

Flirt4Free 1 year ago

His Personal Fucktoy

His Personal Fucktoy

xHamster 3 months ago

Turned Out Sissy Interactive Toy Experience

Turned Out Sissy Interactive Toy Experience

xHamster 1 year ago

Sissykanisa, a Submissive Femboy Play with Her Mistress's Panties

Sissykanisa, a Submissive Femboy Play with Her Mistress's Panties

xHamster 1 year ago

Petra the hardcore anal slut (incl dap tap fist en huge dildo)

Petra the hardcore anal slut (incl dap tap fist en huge dildo)

xHamster 2 weeks ago

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

ShemaleSin 1 year ago

Fucking in the Great Outdoors W/ Ryley Rails and Brie Lovely

58% HD 0:39 / 18:17

Fucking in the Great Outdoors W/ Ryley Rails and Brie Lovely

FapHouse 4 months ago

Double Homework - Episode 6 Gameplay by LoveSkySan69

Double Homework - Episode 6 Gameplay by LoveSkySan69

xHamster 1 year ago

Troy Khalil Private Show

HD 2:00 / 13:19

Troy Khalil Private Show

Flirt4Free 2 years ago

Miss Rose's Slutschool - My sexy booty training

Miss Rose's Slutschool - My sexy booty training

xHamster 2 years ago

Trainer's Training Session No. 89: a Quiet Park Walk with Exposure and Peeing

HD 0:39 / 12:24

Trainer's Training Session No. 89: a Quiet Park Walk with Exposure and Peeing

FapHouse 2 weeks ago

Pussygams or anal climax? is the same for this large booty Femboy ???? Drilled by Large ebony sextoy

Pussygams or anal climax? is the same for this large booty Femboy ???? Drilled by Large ebony sextoy

ShemaleSin 1 week ago

Joven Ladyboy Tiene Orgasmo Analyoung Ladyboy Has a Sissygasm

Joven Ladyboy Tiene Orgasmo Analyoung Ladyboy Has a Sissygasm

xHamster 3 months ago

Femdom Real Pair female domination pegging & ding-dong headmistress & sissy cuck feminization FULL episode

Femdom Real Pair female domination pegging & ding-dong headmistress & sissy cuck feminization FULL episode

FreePorn8 1 year ago

Sissy Training by Queen Daralis Part 5

57% HD 0:39 / 4:59

Sissy Training by Queen Daralis Part 5

FapHouse 3 weeks ago

CAPTAIN CASTLE: Tgirl Sailor Butt Fuck Facial ABRIDGED

CAPTAIN CASTLE: Tgirl Sailor Butt Fuck Facial ABRIDGED

xHamster 4 months ago

Master Collins Private Show

Master Collins Private Show

Flirt4Free 4 weeks ago

Sissy's Ass Make a War with a Big Red Rocket Dildo

66% 1:01 / 21:39

Sissy's Ass Make a War with a Big Red Rocket Dildo

FapHouse 1 month ago

Stacked Oriental shemale trained in submission and bondage

Stacked Oriental shemale trained in submission and bondage

PornLib 3 years ago

Milky Bois merely! Sissy Trainer! WARNING Y

Milky Bois merely! Sissy Trainer! WARNING Y

TrannyGem 5 years ago

Trans Sissy Whore disciplined by Mistresse Murmur compilation

Trans Sissy Whore disciplined by Mistresse Murmur compilation

ShemaleSin 2 months ago

Stretch My Black Hole in Pink Panties

Stretch My Black Hole in Pink Panties

xHamster 1 year ago

My Shemale hentai Tennis Coach Trains Me Hard Everyday

My Shemale hentai Tennis Coach Trains Me Hard Everyday

ShemaleSin 3 weeks ago

”FEMOUT XXX - Viola Teasing With Her Smooth Hole In Sofa”

”FEMOUT XXX - Viola Teasing With Her Smooth Hole In Sofa”

LesbianBliss 1 month ago

Diversity Itsol HFO training mindfuck

Diversity Itsol HFO training mindfuck

SortPorn 1 month ago

Sissy Takes Massive BBC Dildos in Ass

Sissy Takes Massive BBC Dildos in Ass

xHamster 1 year ago

Anal orgasm, cumshots in my mouth, compilation of my hot cumshots Clip 1

Anal orgasm, cumshots in my mouth, compilation of my hot cumshots Clip 1

xHamster 2 months ago

2 Mates Plumbed Me So Rock-hard Intensively Today. I Sensed Enjoy with Them & Their Spunk Explosions

2 Mates Plumbed Me So Rock-hard Intensively Today. I Sensed Enjoy with Them & Their Spunk Explosions

Gayhub 4 months ago

Huge hands free cumshot sissygasm

Huge hands free cumshot sissygasm

xHamster 1 year ago

Bnwo Sissy Bride Gooning

72% HD 1:01 / 12:06

Bnwo Sissy Bride Gooning

FapHouse 5 months ago

Sissy Bitch Addiction (Sissy caption Story)

Sissy Bitch Addiction (Sissy caption Story)

ShemaleSin 4 years ago

Sissygasm for Domina

Sissygasm for Domina

xHamster 6 months ago

Sissy Slut Uses Cum as Lube and has Anal Sissygasms in Chastity Jessica Bloom

Sissy Slut Uses Cum as Lube and has Anal Sissygasms in Chastity Jessica Bloom

xHamster 6 months ago

I Woke up My Sissy and Fucked Her Hole with Fisting

I Woke up My Sissy and Fucked Her Hole with Fisting

xHamster 3 months ago

FAGGOT OBSESSION

FAGGOT OBSESSION

LoyalFans 2 years ago

Get rid of your cock - The Lady of Feminisation gives you sissy cunt a nice cameltoe panty

Get rid of your cock - The Lady of Feminisation gives you sissy cunt a nice cameltoe panty

xHamster 2 years ago

Insatiable Sissy Melody Sluts Out with a Huge Dildo

Insatiable Sissy Melody Sluts Out with a Huge Dildo

xHamster 1 year ago

(makingoff seen from you) valentine's day facial ejaculation 2138 on les pompeuses. vanessabitchx

(makingoff seen from you) valentine's day facial ejaculation 2138 on les pompeuses. vanessabitchx

xHamster 2 weeks ago

To Meet The Inlaws

4K 0:30 / 15:45

To Meet The Inlaws

Clips4sale 1 year ago

Sissy pluged riding BBC Dildo at desk

Sissy pluged riding BBC Dildo at desk

xHamster 4 months ago

Sissy Slut Enjoys BBC, Cums Handsfree

Sissy Slut Enjoys BBC, Cums Handsfree

xHamster 2 months ago

Doe Cosplay | Masturbation Without Panties

Doe Cosplay | Masturbation Without Panties

Flirt4Free 2 months ago

FEMALE DOMINATION HANDBALLING ASSFUCKING INSTRUCTING PEGGING DOMINATRIX PREDOMINANCE FEMBOY

FEMALE DOMINATION HANDBALLING ASSFUCKING INSTRUCTING PEGGING DOMINATRIX PREDOMINANCE FEMBOY

TrannyGem 4 years ago

Dress My Dolly

58% HD 0:10 / 16:50

LoyalFans 2 years ago

Assfucked by a Sissy

Assfucked by a Sissy

xHamster 2 months ago

The Reward for the Locked-up Sissy

The Reward for the Locked-up Sissy

xHamster 3 months ago

Hefty fake penis compete! See how this femboy ass fucking wanks using four big fake penises!

Hefty fake penis compete! See how this femboy ass fucking wanks using four big fake penises!

TrannyGem 4 years ago

trans sissy in chastity anal training by large bbc wang

trans sissy in chastity anal training by large bbc wang

ShemaleSin 1 week ago

I Fucked My New Toy, and I Left All My Cum Inside It

61% HD 2:00 / 4:00

I Fucked My New Toy, and I Left All My Cum Inside It

Flirt4Free 3 years ago

Spanking and anal dildo training for sissy shemale from her femdom mistress

Spanking and anal dildo training for sissy shemale from her femdom mistress

XCafe 2 years ago

Crhistian and his Friend Thony Go At It

HD 2:00 / 18:17

Crhistian and his Friend Thony Go At It

Flirt4Free 7 years ago

Ken Prince Gets His Ass Smashed With A 25CM Thick Cucumber

Ken Prince Gets His Ass Smashed With A 25CM Thick Cucumber

xHamster 1 month ago

milf trans submissa apanhando nas bolas e bebendo mijo

milf trans submissa apanhando nas bolas e bebendo mijo

PissVids 11 months ago

Sissy Bride Getting Fucked by Her Doll

Sissy Bride Getting Fucked by Her Doll

xHamster 6 months ago

Sissy Cascading Spunk

Sissy Cascading Spunk

TrannyGem 2 years ago

Argentinian guy humiliating Colombian Slut

Argentinian guy humiliating Colombian Slut

xHamster 1 year ago

Whorish Femboy Maid in Innocence Takes Harsh Assfucking Teaching ~oscar20xxx~

Whorish Femboy Maid in Innocence Takes Harsh Assfucking Teaching ~oscar20xxx~

GayCK 6 years ago

Lorens Valiant Private Show

HD 2:00 / 15:00

Lorens Valiant Private Show

Flirt4Free 3 years ago

Smooth Jocvk Jerks His Massive Cock

HD 2:00 / 22:50

Smooth Jocvk Jerks His Massive Cock

Flirt4Free 8 years ago

PuppyGirl Itsol heads for a walk and gets pegged

PuppyGirl Itsol heads for a walk and gets pegged

Transvids.tv 8 months ago

AB080 新春特辑-玉兔淫春(中英字幕)女王.深喉.假阳具.开高叉.手淫.射精.丝袜.高跟

AB080 新春特辑-玉兔淫春(中英字幕)女王.深喉.假阳具.开高叉.手淫.射精.丝袜.高跟

TransTube.tv 1 year ago

femboy s training compilation

femboy s training compilation

Eporner 1 year ago

Doll hard-on rubdown

Doll hard-on rubdown

TrannyGem 2 years ago

Limp clitty training Clip 1

Limp clitty training Clip 1

xHamster 1 month ago

Cross Dresser slut jenni needs bbc whore training

Cross Dresser slut jenni needs bbc whore training

SexTubeSpot 5 years ago

Sissy Girlfriend Gets a Sweet and Hard Ass Fuck

HD 1:01 / 16:00

Sissy Girlfriend Gets a Sweet and Hard Ass Fuck

FapHouse 2 months ago

Sissy teasing in shiny leggings and new inverted chastity

Sissy teasing in shiny leggings and new inverted chastity

xHamster 5 months ago

Sissies Like Us (Kimber James)

Sissies Like Us (Kimber James)

ShemaleSin 2 years ago

Beverly Campbell Private Show

Beverly Campbell Private Show

Flirt4Free 1 week ago

Riding XL Trent with hard bouncing cock

Riding XL Trent with hard bouncing cock

xHamster 3 years ago

rubber slave training ass on fucking machine

rubber slave training ass on fucking machine

xHamster 3 weeks 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 2 months ago

Training my ass pussy for the BNWO and my place in it

Training my ass pussy for the BNWO and my place in it

xHamster 1 year ago

Kayla's SISSY Sissyfication INSTRUCTING Directives

Kayla's SISSY Sissyfication INSTRUCTING Directives

TrannyGem 2 years ago

Tranny stretching her little Tight Asshole with a Massive Wide Dildo in Reverse Cowgirl

Tranny stretching her little Tight Asshole with a Massive Wide Dildo in Reverse Cowgirl

xHamster 2 years ago

He so Wants to Cum, but His Hands and Head Are Shackled!

He so Wants to Cum, but His Hands and Head Are Shackled!

xHamster 1 year ago

Str8 Trainer

49% HD 0:10 / 22:55

LoyalFans 2 months ago

Tights Purity Sissy gets Pegged Thru Torn Nylons with Big Bad Dragon Strap-on by Domme

Tights Purity Sissy gets Pegged Thru Torn Nylons with Big Bad Dragon Strap-on by Domme

Transvids.tv 7 months ago

Ali Da Reaper pummeling my taut tiny sissy crevasse with his big black cock

Ali Da Reaper pummeling my taut tiny sissy crevasse with his big black cock

TrannyGem 2 years ago

I was Feminized and become a Creampie and Breeding Shemale Whore!

I was Feminized and become a Creampie and Breeding Shemale Whore!

xHamster 3 months ago

Brutus K Private Show

59% HD 2:00 / 6:01

Brutus K Private Show

Flirt4Free 9 years ago

Toy for Both. Threesome with Trans Sex Doll, Blowjob, DP Hot Sex

Toy for Both. Threesome with Trans Sex Doll, Blowjob, DP Hot Sex

FapHouse 1 week ago

suck dick

Flirt4Free 1 year ago

Threesome Slut Training Sharing with BF Part 2

Threesome Slut Training Sharing with BF Part 2

xHamster 2 months ago

Smoking whore loves training with BBC

Smoking whore loves training with BBC

xHamster 4 months ago

Master Trains His Sissy In Chastity He Uses Her Mouth And Her Liking Making Her A Real Whore Shemal

Master Trains His Sissy In Chastity He Uses Her Mouth And Her Liking Making Her A Real Whore Shemal

aShemaleTube 1 month ago

Luke Hardy & Cristian Ford Private Show

63% 4K 2:00 / 8:35

Luke Hardy & Cristian Ford Private Show

Flirt4Free 2 days ago

OPEN UP AND SWALLOW, REAL FUTANARI TAKER POV RUSSIAN MISTRESS. EVELYN ROSE

OPEN UP AND SWALLOW, REAL FUTANARI TAKER POV RUSSIAN MISTRESS. EVELYN ROSE

Juicexxx 1 month ago

Jasmin Sissy Trans CD - Anal Dildo Masturbation & Sissygasm on Cam

Jasmin Sissy Trans CD - Anal Dildo Masturbation & Sissygasm on Cam

FapHouse 1 week ago

Fuck Stick getting off with figure corset crossdresser

Fuck Stick getting off with figure corset crossdresser

TrannyGem 3 years ago

FUCKED BY SHEMALES

59% HD 0:10 / 15:14

FUCKED BY SHEMALES

LoyalFans 6 months ago

Summer Training

62% HD 0:39 / 23:44

Summer Training

FapHouse 1 year ago

BIG ASS Sissy TWERKS, FUCKS Dildo & SQUiRTS lots of CUM

BIG ASS Sissy TWERKS, FUCKS Dildo & SQUiRTS lots of CUM

xHamster 4 years ago

Anal Training Sph Bbc

68% HD 2:00 / 26:41

Anal Training Sph Bbc

Flirt4Free 4 years ago

Dimitri Caruso Private Show

HD 2:00 / 28:47

Dimitri Caruso Private Show

Flirt4Free 2 years ago

Switch Places Sissy

59% HD 0:10 / 9:50

Switch Places Sissy

LoyalFans 1 year ago

Daddy Teaches You LIFE with Huge Load of Cum - Obedience Training

Daddy Teaches You LIFE with Huge Load of Cum - Obedience Training

xHamster 2 years ago

Crazy Sissy Big Anal Creampie and Fucked with Two Huge Dildos

Crazy Sissy Big Anal Creampie and Fucked with Two Huge Dildos

xHamster 1 month ago

Painful ruined orgasm cbt for my bondaged sub sissy whore

Painful ruined orgasm cbt for my bondaged sub sissy whore

xHamster 4 years ago

Femboy in thong pounding gaping ass with real dildo and jerking off big cock

Femboy in thong pounding gaping ass with real dildo and jerking off big cock

xHamster 1 year ago

Master & Ithan Private Show

62% HD 2:00 / 20:20

Master & Ithan Private Show

Flirt4Free 9 months ago

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