Training Videos - Trans (89,854)

Stivens & Fredy & Stuard Private Show

66% HD 2:00 / 9:52

Stivens & Fredy & Stuard Private Show

Flirt4Free 2 years ago

”TS Stunning Aubrey Kate's Seductive Training & Passionate Pleasure”

”TS Stunning Aubrey Kate's Seductive Training & Passionate Pleasure”

ThePornstar 1 year ago

Thick crossdresser gets by machine

Thick crossdresser gets by machine

xHamster 1 year ago

femboy in innocence cell w restrain bondage getup getting plowed on couch

femboy in innocence cell w restrain bondage getup getting plowed on couch

TrannyGem 3 years ago

Sissys Pussy Clit Teased N Dildo Destroyed Gushing Cum

Sissys Pussy Clit Teased N Dildo Destroyed Gushing Cum

JuicyTrans 2 weeks ago

Hot Crossdresser Cums Hand in Chastity on White Nylons

Hot Crossdresser Cums Hand in Chastity on White Nylons

Amateur8 1 week ago

Sissy , virginity , utter ball and humping machine

Sissy , virginity , utter ball and humping machine

TrannyGem 2 years ago

Spit Roast Training

Spit Roast Training

xHamster 1 year ago

Dianna Campbel Private Show

HD 2:00 / 10:44

Dianna Campbel Private Show

Flirt4Free 2 weeks ago

Melaniie Moon Private Show

Melaniie Moon Private Show

Flirt4Free 1 week ago

Horny Femboy Crossdresser Self Train and Cum Madzmoto Sun

Horny Femboy Crossdresser Self Train and Cum Madzmoto Sun

xHamster 1 year ago

Latex Mistress Training Anal Sissy in Chastity

Latex Mistress Training Anal Sissy in Chastity

xHamster 2 years ago

POV Roommate Cock Sucking Persuasion, Dirty Talk and Sph

62% HD 1:01 / 11:01

POV Roommate Cock Sucking Persuasion, Dirty Talk and Sph

FapHouse 1 year ago

Turning the Hetero you into a HOMOSEXUAL sissy Cumslut

Turning the Hetero you into a HOMOSEXUAL sissy Cumslut

TrannyGem 4 years ago

Toga Convinces You to Cross Dress

HD 0:39 / 20:11

Toga Convinces You to Cross Dress

FapHouse 3 months ago

SISSY DIAPER slave gets PEGGED after releasing PISS ENEMA

SISSY DIAPER slave gets PEGGED after releasing PISS ENEMA

xHamster 1 year ago

Margaux Fox Private Show

HD 2:00 / 15:28

Margaux Fox Private Show

Flirt4Free 4 years ago

Sklavenboy Training

Sklavenboy Training

xHamster 1 year ago

AB090 Two mistress training sissy bondage quick milking with big cumshot - BDSM -高速榨精捆绑女高校生

AB090 Two mistress training sissy bondage quick milking with big cumshot - BDSM -高速榨精捆绑女高校生

aShemaleTube 2 years ago

Sexy Sissy Gets Anal Training by Her MILF Mistress and Fucked with Huge Dildo and Cweet Cumshot

Sexy Sissy Gets Anal Training by Her MILF Mistress and Fucked with Huge Dildo and Cweet Cumshot

xHamster 1 year ago

Sissy Candy in Red Lingerie Gets Spitroasted by Her Fucking Machine and Doll

Sissy Candy in Red Lingerie Gets Spitroasted by Her Fucking Machine and Doll

xHamster 1 year ago

Wondrous CD Sissy Superslut Jacking Her Wood

Wondrous CD Sissy Superslut Jacking Her Wood

GayCK 3 years ago

Pussy Doll Having Fun

Pussy Doll Having Fun

xHamster 1 month ago

Samy Presleys Private Show

Samy Presleys Private Show

Flirt4Free 2 weeks ago

Bladder Training Time!

Bladder Training Time!

xHamster 7 months ago

Deepthroat training with a double ended dildo. It is getting deeper

Deepthroat training with a double ended dildo. It is getting deeper

xHamster 2 years ago

Anal pranks Aleksa Fantasies sexy russian crossdressing

Anal pranks Aleksa Fantasies sexy russian crossdressing

ShemaleSin 1 week ago

You're Just Some Holes, Slut!

You're Just Some Holes, Slut!

xHamster 5 months ago

Sissification lecture "Encaged Sissy" V-Card Belts, Masturbate, Sissygasm by Domina Veronica Taboo

Sissification lecture "Encaged Sissy" V-Card Belts, Masturbate, Sissygasm by Domina Veronica Taboo

TrannyGem 4 years ago

What my sissy bitch will do for a chance to cum! 49cm/nineteen.3in Booty plug! Attempt 1, two & three

What my sissy bitch will do for a chance to cum! 49cm/nineteen.3in Booty plug! Attempt 1, two & three

ShemaleSin 1 year ago

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

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

LesbianBliss 1 month ago

Day 2 Tease and Denial

Day 2 Tease and Denial

xHamster 5 months ago

Gorgeous French Maid is ready to service

Gorgeous French Maid is ready to service

xHamster 4 years ago

Slow-motion Squirting

Slow-motion Squirting

xHamster 3 weeks ago

Cucked And Clowned

63% HD 0:10 / 13:09

Cucked And Clowned

LoyalFans 2 years ago

Sissy Naomi Deepthroat Training

Sissy Naomi Deepthroat Training

aShemaleTube 3 years ago

crossdresser submissa da bunda grande humilhada aos pes do mestre que a pune com socos

65% 5:18 / 12:36

crossdresser submissa da bunda grande humilhada aos pes do mestre que a pune com socos

PornBox 1 year ago

Dildo+lovense= Real Destroy Anal... My Two Favorite Toys Together

Dildo+lovense= Real Destroy Anal... My Two Favorite Toys Together

Flirt4Free 1 year ago

loser training chastity spreading

loser training chastity spreading

Nuvid 1 month ago

Day 22 of Sissy Training - Public Panty Peril

HD 0:39 / 20:07

Day 22 of Sissy Training - Public Panty Peril

FapHouse 1 week ago

Petite Emo White Trans Girl with Big Puffy Nipples Sucks and Milks Them with a Vacuum Pump

Petite Emo White Trans Girl with Big Puffy Nipples Sucks and Milks Them with a Vacuum Pump

xHamster 5 months ago

Sissy Slut Training 4

Sissy Slut Training 4

xHamster 5 months ago

Asian Shemale Virgin Ass Anal Training and Ass to Mouth

Asian Shemale Virgin Ass Anal Training and Ass to Mouth

xHamster 4 years ago

Training Comp

aShemaleTube 6 years ago

Sexy submissive girl in sexy dress

Sexy submissive girl in sexy dress

xHamster 4 years ago

Sissy's butt filled and diapered sextoy training

Sissy's butt filled and diapered sextoy training

ShemaleSin 2 months ago

SISSY SLUT BIMBO MESMERIZE

59% HD 0:10 / 13:20

SISSY SLUT BIMBO MESMERIZE

LoyalFans 2 years ago

116 min degrading of bdsm sissy pain whore Alina

116 min degrading of bdsm sissy pain whore Alina

xHamster 1 year ago

Sissy Cora Self Facial Cum Eating

Sissy Cora Self Facial Cum Eating

xHamster 4 years ago

Premature Handsfree Sissygasm - Jizz shot in 30 Seconds!

Premature Handsfree Sissygasm - Jizz shot in 30 Seconds!

Gayhub 4 months ago

Mindless Ruined Faggot Jes Brinch from Denmark

Mindless Ruined Faggot Jes Brinch from Denmark

xHamster 5 months ago

Elix & Elias & Paulo Private Show

62% HD 2:00 / 4:57

Elix & Elias & Paulo Private Show

Flirt4Free 6 months ago

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

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

xHamster 5 months ago

Ryley Rails Edging JOI

Ryley Rails Edging JOI

xHamster 5 months ago

Paola Balconi Private Show

HD 2:00 / 20:10

Paola Balconi Private Show

Flirt4Free 2 years ago

Femboy training part 1: The Back Arch

Femboy training part 1: The Back Arch

Pornzona 14 hours ago

Lara White Sissy Enjoing herself Crossdressing and twering Femboy asspussy Crossdresser Shemale Tranny Compilation

Lara White Sissy Enjoing herself Crossdressing and twering Femboy asspussy Crossdresser Shemale Tranny Compilation

xHamster 3 years ago

SometimesNiki sissy maid oral training

SometimesNiki sissy maid oral training

xHamster 1 year ago

Entrenamiento de glúteos

Entrenamiento de glúteos

TrannyGem 8 months ago

Instructions From the Trainer No. 25 Outdoor Anal Play 2

Instructions From the Trainer No. 25 Outdoor Anal Play 2

xHamster 4 months ago

femdom futa Mommy pegs you and makes you her cocksucking sissy slut - full video on veggiebabyy Manyvids

femdom futa Mommy pegs you and makes you her cocksucking sissy slut - full video on veggiebabyy Manyvids

xHamster 3 years ago

Degraded sissy bang doll - throat vagina training

Degraded sissy bang doll - throat vagina training

ShemaleSin 4 years ago

fodendo a gostosa da luiza devil na cachoeira em taubate

fodendo a gostosa da luiza devil na cachoeira em taubate

PornBox 3 months ago

these task necessary to become pure sissy given by mistress

these task necessary to become pure sissy given by mistress

PissVids 1 year ago

Homosexual Futanari Servitude - Tgirl Trans Gal Creampies Bound Up Dude With Giant Knob

Homosexual Futanari Servitude - Tgirl Trans Gal Creampies Bound Up Dude With Giant Knob

Amateur8 4 days ago

Sissy Stacy Spread Her Legs and Powerful Bangs Her Ass

Sissy Stacy Spread Her Legs and Powerful Bangs Her Ass

FapHouse 6 months ago

Hattabi4ik warm russian femboy showcases caboose buttplug in backside and spills during going knuckle deep scorching meaty culo

Hattabi4ik warm russian femboy showcases caboose buttplug in backside and spills during going knuckle deep scorching meaty culo

TrannyGem 2 years ago

Petra,s 6th training

Petra,s 6th training

xHamster 1 year ago

sissies don't have to breed: entreat shemale hentai step-mamma to castrate u - full clip on Veggiebabyy Manyvids

sissies don't have to breed: entreat shemale hentai step-mamma to castrate u - full clip on Veggiebabyy Manyvids

Lesbian8 3 months ago

Kept In A Bimbo Mindset

Kept In A Bimbo Mindset

LoyalFans 1 year ago

Lovely lil trap rectal instructing

Lovely lil trap rectal instructing

TrannyGem 4 years ago

Amazing Blowjob to One of My Favourite Neighbours

Amazing Blowjob to One of My Favourite Neighbours

xHamster 1 year ago

Sissy Femme Sandy Anal Dildo Fuck, Ass Egg Birth and Taste Piss & Oinks

Sissy Femme Sandy Anal Dildo Fuck, Ass Egg Birth and Taste Piss & Oinks

xHamster 2 months ago

Ruslana Coval Private Show

Ruslana Coval Private Show

Flirt4Free 6 days ago

Free Hands Cumshot

62% HD 0:39 / 2:00

Free Hands Cumshot

FapHouse 11 months ago

Marionette get agonizing flagellating cock and ball torture HD

Marionette get agonizing flagellating cock and ball torture HD

GayCK 3 years ago

Good Looking Muscle Guy Flexes for You

HD 2:00 / 12:28

Good Looking Muscle Guy Flexes for You

Flirt4Free 10 years ago

Your Sissy Secret Is Safe with Me...for Now - Asmr, Task, Anal Training

HD 1:01 / 10:24

Your Sissy Secret Is Safe with Me...for Now - Asmr, Task, Anal Training

FapHouse 1 year ago

Asshole Stretching Good Time!!

Asshole Stretching Good Time!!

xHamster 3 months ago

TRANSSEXUAL Willow Hammerz - I'm a sissy mega-bitch for BIG BLACK COCK

TRANSSEXUAL Willow Hammerz - I'm a sissy mega-bitch for BIG BLACK COCK

TrannyGem 6 months ago

Sandy Nell Private Show

Sandy Nell Private Show

Flirt4Free 3 months ago

BBC Thrall Obedience Drill Femdom Sissy ASMR JOI BRAINWAVES

BBC Thrall Obedience Drill Femdom Sissy ASMR JOI BRAINWAVES

ShemaleSin 1 month ago

Jasmine_dlight & Valentina Rosa & Ava Black - the Slut Sandwich Extreme Strapon Domination - Extreme Anal Shemale Slut

HD 1:01 / 13:33

Jasmine_dlight & Valentina Rosa & Ava Black - the Slut Sandwich Extreme Strapon Domination - Extreme Anal Shemale Slut

FapHouse 10 months ago

Wanda Snake Private Show

4K 2:00 / 10:46

Wanda Snake Private Show

Flirt4Free 6 months ago

Alexxa A Private Show

HD 2:00 / 11:23

Alexxa A Private Show

Flirt4Free 5 days ago

Big Ass Trans Raven Anal Gaped and Bred after Riding Bbc Fat Dildo

Big Ass Trans Raven Anal Gaped and Bred after Riding Bbc Fat Dildo

xHamster 2 months ago

Lady Becky Teaches Sissy Slut Michelle to Masturbate in a Propper Way

HD 1:01 / 48:52

Lady Becky Teaches Sissy Slut Michelle to Masturbate in a Propper Way

FapHouse 2 years ago

Sissy Trap Gushes Self Facial Squirt Destroyed Toy Anal Fuck Cumslut Training

Sissy Trap Gushes Self Facial Squirt Destroyed Toy Anal Fuck Cumslut Training

JuicyTrans 12 hours ago

Cum in your Wife's sexy Panties (mov)

Cum in your Wife's sexy Panties (mov)

Clips4sale 4 years ago

Smallish Plaything in Brown Sphincter and Milking with Maturbator! Sissification of Quinne

Smallish Plaything in Brown Sphincter and Milking with Maturbator! Sissification of Quinne

TrannyGem 4 years ago

Jasmine Dlight - Extreme Anal Training with John Thomas Xl Depth Trainer 30inches Full Dildo

Jasmine Dlight - Extreme Anal Training with John Thomas Xl Depth Trainer 30inches Full Dildo

xHamster 2 months ago

Rebeccah Gibson Private Show

HD 2:00 / 14:47

Rebeccah Gibson Private Show

Flirt4Free 1 month ago

4K - FULL CREAM COMPILATION NEO 7

43% 4K 0:20 / 18:01

4K - FULL CREAM COMPILATION NEO 7

Clips4sale 1 year ago

Sissy Fem Princess Calls You Out

Sissy Fem Princess Calls You Out

TrannyGem 9 months ago

Hole Stretching, Spanking, and Wax Play w Mia &amp; Bia

Hole Stretching, Spanking, and Wax Play w Mia &amp; Bia

Clips4sale 2 years ago

Nathaly Rose & Lizz Grant Private Show

Nathaly Rose & Lizz Grant Private Show

Flirt4Free 6 days ago

Sissygasm From Fat Dick I the Ass

Sissygasm From Fat Dick I the Ass

xHamster 3 weeks ago

He Used to Be the Boss but Not Anymore

He Used to Be the Boss but Not Anymore

FapHouse 9 months ago

Sissyfication Feminization Hotwife Sissy instructing Lesson one - When your wifey is with her paramour

Sissyfication Feminization Hotwife Sissy instructing Lesson one - When your wifey is with her paramour

TrannyGem 7 months ago

HornyEmpressKay - TRANSSEXUAL Kay screws her BITCH in his splendid donk

HornyEmpressKay - TRANSSEXUAL Kay screws her BITCH in his splendid donk

TrannyGem 4 years ago

double end dildo compilation

double end dildo compilation

AnalVids 1 year ago

Horny TS Skips School

63% HD 0:39 / 10:44

Horny TS Skips School

FapHouse 2 years ago

Brunette hair trans is training deepthroat

Brunette hair trans is training deepthroat

ShemaleSin 4 months ago

This chab Not fast Became a Very Nice Hotty

This chab Not fast Became a Very Nice Hotty

ShemaleSin 3 months ago

Trans Domme Breaks In Sissy Slave With Cruel Cuckold Training – Full Audio

Trans Domme Breaks In Sissy Slave With Cruel Cuckold Training – Full Audio

HihentaiPorn 9 months ago

Full Video Stupid Sissy in Halloween Costume and Chastity Cage Surrenders and Jerks off to Big Black Cock

HD 0:39 / 18:35

Full Video Stupid Sissy in Halloween Costume and Chastity Cage Surrenders and Jerks off to Big Black Cock

FapHouse 5 months ago

nude lean t-girl posing luxurious arse and self facial cumshot jizz shot

nude lean t-girl posing luxurious arse and self facial cumshot jizz shot

TrannyGem 1 year ago

Tiny Femboy Training His Little Hole With HUGE Dildo

Tiny Femboy Training His Little Hole With HUGE Dildo

xHamster 3 years ago

Mikes Hanon Private Show

Mikes Hanon Private Show

Flirt4Free 5 years ago

Teaching my sissy cunt with my Xxl Black Fuck Stick

Teaching my sissy cunt with my Xxl Black Fuck Stick

TrannyGem 3 years ago

I Need It Deep

xHamster 5 months ago

Beth Kinky - Sexy got domina trains her shemale horseman pt1 HD

Beth Kinky - Sexy got domina trains her shemale horseman pt1 HD

XVideos 5 years ago

Ass-Fuck Beads Blow-Job teaching and Pulverize Machine Ejaculation

Ass-Fuck Beads Blow-Job teaching and Pulverize Machine Ejaculation

TrannyGem 3 years ago

Anal Bang Machine Compilation 1

Anal Bang Machine Compilation 1

ShemaleSin 1 year ago

pegging mistress compilation

pegging mistress compilation

AnalVids 9 months ago

Come and see the nurse, don't be afraid of it. A Taspe Ye Ye... VaneSsaBiTCHx PariSChienne Trvprod91

Come and see the nurse, don't be afraid of it. A Taspe Ye Ye... VaneSsaBiTCHx PariSChienne Trvprod91

xHamster 1 week ago

Stretching out my sissy's boipussy with my huge big black cock

Stretching out my sissy's boipussy with my huge big black cock

xHamster 2 months ago

Training of a Submissive Bitch, Fisting and Gape in the Pussy

Training of a Submissive Bitch, Fisting and Gape in the Pussy

xHamster 2 weeks ago

Phat ass crossdresser let her mistress peg her with strap on

Phat ass crossdresser let her mistress peg her with strap on

XGroovy 1 year ago

Daily cross dresser training ruined climax joi with s1monreilly

Daily cross dresser training ruined climax joi with s1monreilly

ManPorn 3 years ago

64 65 66 67 68

89,854 results found

Related categories

Chastity Cage Cage Leashed Slave Training Dungeon Chastity Slave Humiliation Bondage Dominatrix Suspension Edging Chastity Belt Latex Submissive Slave Spanked Whip Bondage Orgasm BDSM Slave Maledom

Narrow your search

sissy training anal training dildo training slave training femdom training sissy anal training cuckold training fisting training slut training chastity training deepthroat training femboy training 18+ femdom anal training stamina training training anal training slave gay training bbc training blowjob training faggot training

Categories Pornstars

Categories Pornstars

PornMD: A Porn Search Engine.

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.