Training Videos - Trans (123,867)

Sissy Slut, are U ready to be Fucked by your Domme Girlfriend? JOI & CEI POV Clip 1

Sissy Slut, are U ready to be Fucked by your Domme Girlfriend? JOI & CEI POV Clip 1

XHamster 4 months ago

Sabrina Smiith Private Show

Sabrina Smiith Private Show

Flirt4Free 10 months ago

beta loser boy gets pegging assfuck by german mistress. Hardcore Anal Orgasm.sissygasm Clip 1

beta loser boy gets pegging assfuck by german mistress. Hardcore Anal Orgasm.sissygasm Clip 1

XHamster 6 months ago

Slut Training Of Milla By Leash Holder Xaevynne

Slut Training Of Milla By Leash Holder Xaevynne

IcePorn 6 months ago

”Sissy Fucker (Strap-on Sex) #FemdomRAW”

”Sissy Fucker (Strap-on Sex) #FemdomRAW”

Trashreality 1 year ago

Bluee & Jayce Private Show

Bluee & Jayce Private Show

Flirt4Free 3 years ago

AB006 Sexy fox Mistress training with Kigurumi mask sissy 性感狐狸女王调教戴着面具的下賤人妖

AB006 Sexy fox Mistress training with Kigurumi mask sissy 性感狐狸女王调教戴着面具的下賤人妖

YouPorn Unknown

Lola Crystals getting mouth pulverized and dicked down nut sack deep by BIG BLACK COCK

Lola Crystals getting mouth pulverized and dicked down nut sack deep by BIG BLACK COCK

TrannyGem 1 year ago

”Naturally Stacked: Breast Exam Training - Riley Nixon, Chloe Surreal”

”Naturally Stacked: Breast Exam Training - Riley Nixon, Chloe Surreal”

TransHero 9 months ago

Sissy Crossdresser Amanda Kiss Bound Up, Teased and Denied By Femdom Girlfriend

Sissy Crossdresser Amanda Kiss Bound Up, Teased and Denied By Femdom Girlfriend

ShemaleSin 2 years ago

P4 VIRGIN RIMMING FUCKING ANAL HOOK CUMSHOT BENCH BONDAGE

65% HD 0:21 / 10:03

P4 VIRGIN RIMMING FUCKING ANAL HOOK CUMSHOT BENCH BONDAGE

Clips4sale 1 year ago

TGIRLHOOKUP Every Hole Is Trained

TGIRLHOOKUP Every Hole Is Trained

DrTuber 1 year ago

THICK LOLLIPOP GRINDR DAD JIZZES DEEP IN SUPER-HOT CROSSDRESSERs SISSY CUNT

THICK LOLLIPOP GRINDR DAD JIZZES DEEP IN SUPER-HOT CROSSDRESSERs SISSY CUNT

TrannyGem 4 years ago

Госпожа захотела попить колы

Госпожа захотела попить колы

TrannyGem 1 year ago

Trannies in Training - EPISODE #03

Trannies in Training - EPISODE #03

Tranny.one 4 years ago

Cattleya Exposito Private Show

Cattleya Exposito Private Show

Flirt4Free 1 year ago

MistressAe &amp_ Miss Hannah Blake Host a Bisexual Orgy: Part 2

MistressAe &amp_ Miss Hannah Blake Host a Bisexual Orgy: Part 2

XVideos 1 year ago

Feminised, Spanked and Jerked off by my Step Aunt!!! - mobile friendly version

Feminised, Spanked and Jerked off by my Step Aunt!!! - mobile friendly version

Clips4sale 10 months ago

Mistress Plays with Her Futanari Dolls

51% 1:01 / 41:16

Mistress Plays with Her Futanari Dolls

FapHouse 1 year ago

Latex Woman Pegging Sissy slut

HD 0:11 / 21:12

Latex Woman Pegging Sissy slut

Clips4sale 4 years ago

Beauty Royalty

Some.Porn 2 years ago

Becoming Candy: Permanent Sissy Identity Imprint

62% HD 0:30 / 42:17

Becoming Candy: Permanent Sissy Identity Imprint

Clips4sale 7 months ago

Hands free sissygasm in chastity bbc anal

Hands free sissygasm in chastity bbc anal

XHamster 3 years ago

Adorable femboy jizzes and loves his fresh Honeykissme plaything

Adorable femboy jizzes and loves his fresh Honeykissme plaything

TrannyGem 3 years ago

Kristy Butty Party on Jun 26, 2026 - Part 2

4K 2:00 / 2:45:21

Kristy Butty Party on Jun 26, 2026 - Part 2

Camster 2 months ago

3D Muscular Mature Woman Heavy Squats & Ass Workout - Classic Gym Tease Clip 1

3D Muscular Mature Woman Heavy Squats & Ass Workout - Classic Gym Tease Clip 1

XHamster 5 months ago

True sissy's must know my secret

True sissy's must know my secret

XHamster 5 months ago

”Butt In Training - Tommy Trains Haley Reed's Butt For Cum Draining”

”Butt In Training - Tommy Trains Haley Reed's Butt For Cum Draining”

TransHero 8 months ago

Dominant Princess Sensually Uses Trans Girl Sextoy Creampie

65% HD 0:26 / 27:09

Dominant Princess Sensually Uses Trans Girl Sextoy Creampie

Clips4sale 1 year ago

entrenamiento de mariquita femboy training ass profundo

entrenamiento de mariquita femboy training ass profundo

SleazyNEasy 5 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

Celeste Darell Private Show

HD 2:00 / 14:22

Celeste Darell Private Show

Flirt4Free 2 years ago

Barbie: Belle

Some.Porn 1 year ago

Charlie Monaco has you Bound Gagged and Made to watch! HD

Charlie Monaco has you Bound Gagged and Made to watch! HD

Clips4sale 1 year ago

Luciana Sainz Private Show

4K 2:00 / 10:55

Luciana Sainz Private Show

Flirt4Free 5 months ago

korean femboy kimono banged

korean femboy kimono banged

4Gay 8 months ago

TRANSSEXUAL Willow Hammerz - 2023 Mega-Bitch of the Yr

TRANSSEXUAL Willow Hammerz - 2023 Mega-Bitch of the Yr

TrannyGem 11 months ago

TRANSGENDER SISSY DROWNS IN DEEPTHROAT FUN AND URINATE

TRANSGENDER SISSY DROWNS IN DEEPTHROAT FUN AND URINATE

ShemaleSin 3 months ago

Trans Deepthroat Training Webcam - Robyn and Amelia Greene

Trans Deepthroat Training Webcam - Robyn and Amelia Greene

XXXShemalePorn 9 years ago

Instructing a lil' trans nymph - Going Knuckle Deep and Glass Fake Penis

Instructing a lil' trans nymph - Going Knuckle Deep and Glass Fake Penis

TrannyGem 1 year ago

Hard Trening Excited Sissy Gap COMPILATION

Hard Trening Excited Sissy Gap COMPILATION

ShemaleSin 5 years ago

Blonde with small tits and scissoring gets a good workout in the gym with ass licking and pussy licking

Blonde with small tits and scissoring gets a good workout in the gym with ass licking and pussy licking

Some.Porn 2 years ago

Order From the Trainer No. 27 Exposure Walk During My Period

Order From the Trainer No. 27 Exposure Walk During My Period

XHamster 9 months ago

Sissy in Office-Outside

Sissy in Office-Outside

XVideos 9 months ago

CEI Cumtrainer Cumfast in 60 Seconds Prejac Cuckold Cumeater Paypig EAT YOUR OWN CUM NOW !

CEI Cumtrainer Cumfast in 60 Seconds Prejac Cuckold Cumeater Paypig EAT YOUR OWN CUM NOW !

ShemaleSin 11 months ago

Axel Russo Private Show

Axel Russo Private Show

Flirt4Free 9 months ago

DIAPER AS BONDAGE - Diaper And Bondage, ABDL Sissy Mind Fuck

57% 0:30 / 30:33

DIAPER AS BONDAGE - Diaper And Bondage, ABDL Sissy Mind Fuck

Clips4sale 1 year ago

”Tranny Sergeant Jessy Dubai Trains Her New Recruits”

”Tranny Sergeant Jessy Dubai Trains Her New Recruits”

Zatube 2 years ago

Lady in Red Stacy Blow off Here Ass by Fuckmashine with Huge Pink Dildo

65% 1:01 / 11:51

Lady in Red Stacy Blow off Here Ass by Fuckmashine with Huge Pink Dildo

FapHouse 11 months ago

Sissy to the Headmistress' Office 4K

36% 4K 0:26 / 11:06

Sissy to the Headmistress' Office 4K

Clips4sale 3 years ago

FLUNY FAGGOT PROFESSOR

HD 0:10 / 10:51

FLUNY FAGGOT PROFESSOR

LoyalFans 3 years ago

Flexible Teen - S17:E8

Flexible Teen - S17:E8

Some.Porn 1 year ago

I Want to Have You Below Me

HD 2:00 / 19:48

I Want to Have You Below Me

Flirt4Free 7 years ago

Submissive Asian Ladyboy Slave Training & Anal Casting

Submissive Asian Ladyboy Slave Training & Anal Casting

XHamster 3 months ago

meeke me hader meke m e cum(d) (sexy) (jerk) (umbrella) (buttspank) (a) (y) (devil) (yummy) (sweating) (drool) (k) (c) (s) (h) (d) (superstud)

meeke me hader meke m e cum(d) (sexy) (jerk) (umbrella) (buttspank) (a) (y) (devil) (yummy) (sweating) (drool) (k) (c) (s) (h) (d) (superstud)

Flirt4Free 5 years ago

Outrageous ejaculation 电击排精

Outrageous ejaculation 电击排精

TrannyGem 9 months ago

White Sissy Virginity Instructing (Smash Machine)

White Sissy Virginity Instructing (Smash Machine)

TrannyGem 10 months ago

［ Asian Sissy Femboy ］Femboy killer who cums only with buttfuck vibration ♡

［ Asian Sissy Femboy ］Femboy killer who cums only with buttfuck vibration ♡

TrannyGem 3 years ago

Anastasia Mistress fucking a slave with strapon anal submission man amateur homemade Sasha Earth

Anastasia Mistress fucking a slave with strapon anal submission man amateur homemade Sasha Earth

XHamster 4 months ago

Goon for Manga Shemale hentai Rods And Their Cum

Goon for Manga Shemale hentai Rods And Their Cum

Lesbian8 1 month ago

Sucking Cock Training Session

Sucking Cock Training Session

AShemaleTube 8 months ago

Alana Lopez Private Show

Alana Lopez Private Show

Flirt4Free 4 years ago

Cialis Dick Leaking Like a Bitch

Cialis Dick Leaking Like a Bitch

XHamster 5 months ago

Hard Sissy Training and SissyGasm Compilation

Hard Sissy Training and SissyGasm Compilation

BeMyHole 6 years ago

Chinese sissy Femboy GOKKUN messy milk Mushy core swim suits

Chinese sissy Femboy GOKKUN messy milk Mushy core swim suits

TrannyGem 9 months ago

Restrained and Deep Fisted – Mistress AE Deep Fists Bound Shemale Jasmine_Dlight Without Mercy

65% 0:30 / 9:22

Restrained and Deep Fisted – Mistress AE Deep Fists Bound Shemale Jasmine_Dlight Without Mercy

Clips4sale 1 year ago

Transgender Princess with ample sausage and donk having joy

Transgender Princess with ample sausage and donk having joy

TrannyGem 4 years ago

Suck me off 100 Times a Day

Suck me off 100 Times a Day

XHamster 1 year ago

Trans-Dimensional Super Girl Is At It Again FULL - Lil Mizz Unique, Autumn Bodell And Sinn Sage 4k

4K 0:30 / 41:20

Trans-Dimensional Super Girl Is At It Again FULL - Lil Mizz Unique, Autumn Bodell And Sinn Sage 4k

Clips4sale 7 months ago

Sissy Obsessed with Panties

Sissy Obsessed with Panties

Clips4sale 2 years ago

Alpha couple releases slave couple from chastity and play with their pleasure (720 EN-sub)

4K 0:38 / 20:40

Alpha couple releases slave couple from chastity and play with their pleasure (720 EN-sub)

Clips4sale 3 years ago

Samu Seanz Private Show

50% HD 2:00 / 4:30

Samu Seanz Private Show

Flirt4Free 3 years ago

Hard No Matter What – Turning You Bi

Hard No Matter What – Turning You Bi

LoyalFans 4 weeks ago

bbc vs. pathetic sissy clitty

bbc vs. pathetic sissy clitty

XHamster 4 years ago

Sissy training from Katy Koroleva

Sissy training from Katy Koroleva

XHamster 2 years ago

Instructions on how to cum for mama

Instructions on how to cum for mama

ShemaleSin 6 months ago

ryu Female takes glowing Sinnovator 20in deep

ryu Female takes glowing Sinnovator 20in deep

TransTube.tv 2 years ago

SISSY SPITROAST

SISSY SPITROAST

Clips4sale 11 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

TrannyGem 10 months ago

Paola Balconi Private Show

63% HD 2:00 / 9:30

Paola Balconi Private Show

Flirt4Free 2 years ago

”Hot Spanish hot girl trains her body for more sexual experiences”

”Hot Spanish hot girl trains her body for more sexual experiences”

ThePornstar 2 years ago

Solo Serf Training Gone Likewise Far (Nearly)

Solo Serf Training Gone Likewise Far (Nearly)

ShemaleSin 10 months ago

Tiara Rossi Private Show

HD 2:00 / 10:03

Tiara Rossi Private Show

Camster 1 year ago

clothespins from my elder smartphone five

clothespins from my elder smartphone five

TrannyGem 2 years ago

Sissy slut training hipnotic

Sissy slut training hipnotic

AShemaleTube 11 years ago

CROSSDRESSING PUPPET MESMERIZE - Made To Crossdressing, Crossdressing Mind Melt

CROSSDRESSING PUPPET MESMERIZE - Made To Crossdressing, Crossdressing Mind Melt

Clips4sale 1 year ago

Military PolicePenis

Military PolicePenis

Some.Porn 2 years ago

Easter Egg Hunt Pt1

68% 0:37 / 4:10

Easter Egg Hunt Pt1

Clips4sale 3 years ago

Cutie-pie Florence Loves Humiliation

Cutie-pie Florence Loves Humiliation

FapHouse 1 year ago

Facesitting Puny Dick Slaves

Facesitting Puny Dick Slaves

Clips4sale 2 years ago

Smoke Sub to a Shemale

Smoke Sub to a Shemale

TrannyGem 1 year ago

Sadie Slime's Sissygasm in Gothic French Maid Getup

Sadie Slime's Sissygasm in Gothic French Maid Getup

TatBabes 2 months ago

Sissy motivation 5: cum with a jock in your booty (sissy coach, sissy instruction, sissification)

Sissy motivation 5: cum with a jock in your booty (sissy coach, sissy instruction, sissification)

ShemaleSin 2 years ago

Luciana Sainz Private Show

Luciana Sainz Private Show

Camster 6 months ago

Emmily Siete Private Show

HD 2:00 / 16:48

Emmily Siete Private Show

Flirt4Free 2 years ago

Luciana Sainz Private Show

Luciana Sainz Private Show

Flirt4Free 6 months ago

Mistress Lady Renee - Prepping the whore for action - wmv

55% 0:16 / 11:33

Mistress Lady Renee - Prepping the whore for action - wmv

Clips4sale 1 year ago

Sissy nurse does assfucking with a orgy machine and jizm with faux-cock in the culo . Sissyfication crossdresser

Sissy nurse does assfucking with a orgy machine and jizm with faux-cock in the culo . Sissyfication crossdresser

TrannyGem 3 years ago

FUCKED WITH MY HIGH HEEL

FUCKED WITH MY HIGH HEEL

XHamster 2 years ago

Dutch tgirl annete toy playing

Dutch tgirl annete toy playing

XHamster 1 year ago

Protect The Virgin Sissy Part 2 Butt Plug and Suck

Protect The Virgin Sissy Part 2 Butt Plug and Suck

Clips4sale 3 years ago

Dildo Dolly 4

58% 0:11 / 11:52

Clips4sale 3 years ago

Sissy Verwandlung

Sissy Verwandlung

Tranny.one 3 years ago

Sissy Load for Obedient Girl Training

Sissy Load for Obedient Girl Training

FapHouse 2 weeks ago

Sissy Outfit Test

Sissy Outfit Test

XHamster 1 year ago

AB082 Bad Girl Miss 3 be spanking and training - deep throat crmpie (Chinese and English subtitles)

AB082 Bad Girl Miss 3 be spanking and training - deep throat crmpie (Chinese and English subtitles)

RedTube Unknown

TS Sissy in Sexy Black Overnees Enjoys Frontal Fisting!

TS Sissy in Sexy Black Overnees Enjoys Frontal Fisting!

FapHouse 1 year ago

Femdom rims my sissy ass while ATM dildo sploshes messy amateur

Femdom rims my sissy ass while ATM dildo sploshes messy amateur

AveXXX 1 month ago

Daddy's sissy in training as Pony Girl with Master

Daddy's sissy in training as Pony Girl with Master

AbTranny 7 years ago

”Big cock gimp fucking tied blonde”

”Big cock gimp fucking tied blonde”

TransHero 8 months ago

AnalQueenTs Sizzles Solo in Tranquil Transexuality

AnalQueenTs Sizzles Solo in Tranquil Transexuality

BallsAndBoobs 2 months ago

Miruplanttt Anal Training With Big Dildo

Miruplanttt Anal Training With Big Dildo

VipTube 7 months ago

Petra.s porno marathon part 2-3

Petra.s porno marathon part 2-3

XHamster 1 year ago

The Pride Parade in Sissy City

66% 0:30 / 11:35

The Pride Parade in Sissy City

Clips4sale 4 months ago

Sissy Femboy Bondage Feminization Training

Sissy Femboy Bondage Feminization Training

XHamster 1 year ago

Shemales Made You Gay

HD 0:20 / 34:25

Shemales Made You Gay

Clips4sale 2 years ago

Training with king cock 12

Training with king cock 12

XHamster 4 years ago

Tarzan Belts His Ass, Combs His Hair, and Fingers His Hole

HD 2:00 / 10:21

Tarzan Belts His Ass, Combs His Hair, and Fingers His Hole

Flirt4Free 9 years ago

Sissy Training Challenge: Can You Handle These Tasks?

Premium HD 9:30

Sissy Training Challenge: Can You Handle These Tasks?

Clips4sale 1 year ago

Bella Hart's Sissygasm Training

Bella Hart's Sissygasm Training

ShemaleSin 4 years ago

95 96 97 98 99

123,867 results found

Related categories

Edging Leashed Collar Goon Cage Chastity Master Chastity Cage Spandex Slave Training CMNF Handcuffed Suspension Mud Spanked POV Femdom Submissive Chastity Belt Mask Flexing

Narrow your search

sissy training dildo training anal training bdsm training faggot training bbc training shemale training cock training deepthroat training blowjob training cum training sissy anal training throat training slut training bi training slave training training anal anal training joi femboy training 18+ training slave

Categories Pornstars

Parents

Pornmd.com uses the “Restricted To Adults” (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Pornmd.com. All rights reserved.

© 2026 Pornmd.com. All rights reserved.