Training Videos - Trans (123,897)

Lika Kai Party on Aug 16, 2026 - Part 2

4K 2:00 / 38:17

Lika Kai Party on Aug 16, 2026 - Part 2

Flirt4Free 1 month ago

Sissy's Dream 3

Sissy's Dream 3

FapHouse 1 year ago

Cock & Sole The Filthy Choice

50% 0:35 / 10:43

Cock & Sole The Filthy Choice

Clips4sale 1 year ago

Tammysissy with Cum and Piss in Face and Body

Tammysissy with Cum and Piss in Face and Body

XHamster 1 month ago

Talia Hot Private Show

Talia Hot Private Show

Flirt4Free 4 days ago

Jewel Selfsucker Party on Aug 22, 2026 - Part 2

65% HD 2:00 / 16:52

Jewel Selfsucker Party on Aug 22, 2026 - Part 2

Flirt4Free 3 weeks ago

Desire Sweet Private Show

HD 2:00 / 23:51

Desire Sweet Private Show

Camster 3 weeks ago

Filthy Piggy Butthole - Queer Bunny Babe and Sinn Sage MP4

66% HD 0:19 / 20:25

Filthy Piggy Butthole - Queer Bunny Babe and Sinn Sage MP4

Clips4sale 4 years ago

After training at the gym there is nothing better than a good cock in my ass

After training at the gym there is nothing better than a good cock in my ass

XHamster 2 years ago

Sissy Affirmation - learning my place

Sissy Affirmation - learning my place

XHamster 3 years ago

Bitch with a Big Cock

Bitch with a Big Cock

XHamster 3 weeks ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 4 days ago

Sophia Loreen Party on Aug 29, 2026 - Part 3

4K 2:00 / 14:29

Sophia Loreen Party on Aug 29, 2026 - Part 3

Flirt4Free 2 weeks ago

Thomas Jasper Private Show

HD 2:00 / 15:41

Thomas Jasper Private Show

Flirt4Free 2 days ago

Cumslut Training Session 3B

Cumslut Training Session 3B

ShemaleSin 5 years ago

Emo Trans Maid Edges and Jizzes While Jiggling

Emo Trans Maid Edges and Jizzes While Jiggling

Transvids.tv 1 year ago

Rebeccah Gibson Private Show

Rebeccah Gibson Private Show

Flirt4Free 1 day ago

Wife Sissifies You - Sissy Training with Rebelle Hart

52% 0:25 / 16:59

Wife Sissifies You - Sissy Training with Rebelle Hart

Clips4sale 1 year ago

Daddy's Cock Pig

Daddy's Cock Pig

XHamster 2 years ago

Long Intense Anal Machine Fuck with Black Fist, Crossdresser Bi Guy

Long Intense Anal Machine Fuck with Black Fist, Crossdresser Bi Guy

FapHouse 2 years ago

Look How I Play with My Tasty Ass

Look How I Play with My Tasty Ass

Flirt4Free 2 years ago

Jessica Simpsin Party on Nov 24, 2019

HD 2:00 / 45:20

Jessica Simpsin Party on Nov 24, 2019

Camster 6 years ago

You Won't Cum if You're Not GAY

61% 4K 0:30 / 15:16

You Won't Cum if You're Not GAY

Clips4sale 7 months ago

Secrets to Sissygasm Easier Every Time

HD 0:25 / 11:03

Secrets to Sissygasm Easier Every Time

IWantClips 2 years ago

BlueCrow42's crossdressing adventure: double cumming on belly & ass while playing with long dildo

BlueCrow42's crossdressing adventure: double cumming on belly & ass while playing with long dildo

TrannyMovs 1 year ago

Demonic Futa nun will fuck you and convert you to become a Satanist - FUTANARI , POV, ANAL, BLASPHEMY

62% 0:18 / 9:29

Demonic Futa nun will fuck you and convert you to become a Satanist - FUTANARI , POV, ANAL, BLASPHEMY

Clips4sale 1 year ago

Exhibitionist Domme & Humiliated Sub: Queen Elena Flashes, Then Gags & Walks Sissy Femme Sandy

44% 0:39 / 5:38

Exhibitionist Domme & Humiliated Sub: Queen Elena Flashes, Then Gags & Walks Sissy Femme Sandy

FapHouse 7 months ago

StepMommy's Futa Cock Sucker

StepMommy's Futa Cock Sucker

XHamster 7 months ago

Nonbianry sissy hubby takes jaw-pulling down all-natural tgirl bone hard af

Nonbianry sissy hubby takes jaw-pulling down all-natural tgirl bone hard af

TransTube.tv 2 years ago

He Wanted to Wreck My Sloppy Hole with a Huge Squirting Dildo

56% HD 0:39 / 43:39

He Wanted to Wreck My Sloppy Hole with a Huge Squirting Dildo

FapHouse 8 months ago

SISSYGASM WITH STEPMOMMY by Phoenix Studio

SISSYGASM WITH STEPMOMMY by Phoenix Studio

TrannyGem 1 year ago

Sissy warm up

XHamster 3 years ago

Horny crossdresser in PVC desperately trying to cum with her hands tied behind her back

Horny crossdresser in PVC desperately trying to cum with her hands tied behind her back

XHamster 3 years ago

skinny submissive ladyboy self anal fisting and slave training

skinny submissive ladyboy self anal fisting and slave training

PornBox 1 year ago

With the recent machine and my crossdresser

With the recent machine and my crossdresser

Lesbian8 1 week ago

Self Sounding and Fist Dildo Training

64% HD 1:01 / 35:32

Self Sounding and Fist Dildo Training

FapHouse 1 year ago

Amazone Lady Naina fists a students ass

Amazone Lady Naina fists a students ass

FapHouse 6 years ago

Milked Sissy Swallows

Milked Sissy Swallows

Clips4sale 5 years ago

Hot Stud Pounds a Muscle Bottom

Hot Stud Pounds a Muscle Bottom

Flirt4Free 8 years ago

Feminized Sissy Servant

HD 0:15 / 16:01

Feminized Sissy Servant

IWantClips 3 months ago

Lisan & Mine Private Show

Lisan & Mine Private Show

Camster 3 weeks ago

Sissy pegging threesome with bbc bull -make Me bi

Sissy pegging threesome with bbc bull -make Me bi

Clips4sale 2 months ago

Stepdaddy Would Wreck Me Right Now

Stepdaddy Would Wreck Me Right Now

FapHouse 3 days ago

Skinny Babe Loves Giving Blowjobs

Skinny Babe Loves Giving Blowjobs

Some.Porn 2 years ago

Hottest cumshow with my toys

HD 2:00 / 14:54

Hottest cumshow with my toys

Camster 2 years ago

Katy Ling Private Show

Katy Ling Private Show

Flirt4Free 1 week ago

Sissy Doesn't Go Toilet. Sissy Pisses in Panties.

Sissy Doesn't Go Toilet. Sissy Pisses in Panties.

XHamster 10 months ago

Sissy Trainer #0 Welcome and Feminize Yourself!

HD 0:39 / 10:24

Sissy Trainer #0 Welcome and Feminize Yourself!

FapHouse 2 months ago

Yei Vela Private Show

HD 2:00 / 12:02

Yei Vela Private Show

Flirt4Free 3 years ago

Female Dominance Wifey makes Hubby Wear her Underpants for Glamour Hj with Icecube

Female Dominance Wifey makes Hubby Wear her Underpants for Glamour Hj with Icecube

TrannyGem 5 years ago

Panty Hood and Panty Gag Instructional - Candle Boxxx BDSM Instruction Sissy Training 4k

4K 0:10 / 24:01

Panty Hood and Panty Gag Instructional - Candle Boxxx BDSM Instruction Sissy Training 4k

LoyalFans 5 months ago

Thin Femboy ass fucking trainning

Thin Femboy ass fucking trainning

4Gay 2 years ago

Shemale Ting Xuan Anal DP Training

Shemale Ting Xuan Anal DP Training

FapHouse 2 years ago

Hot blonde coach indulges in some steamy lesbian pussy eating after a workout

Hot blonde coach indulges in some steamy lesbian pussy eating after a workout

Some.Porn 2 years ago

Sandy Lee Private Show

HD 2:00 / 10:00

Sandy Lee Private Show

Flirt4Free 10 years ago

Wanda Snake Private Show

Wanda Snake Private Show

Flirt4Free 9 months ago

Femization Lesson POV Femdom with Madame Juliette

53% 0:12 / 10:04

Femization Lesson POV Femdom with Madame Juliette

Clips4sale 3 years ago

Lashing joy.

TrannyGem 1 year ago

Submissive Asian Ladyboy Slave Training & First Anal Casting

Submissive Asian Ladyboy Slave Training & First Anal Casting

XHamster 3 months ago

Carrie Emberlyn Bbc Training

Carrie Emberlyn Bbc Training

GetTranny 3 years ago

Lika Kai Private Show

Lika Kai Private Show

Flirt4Free 2 days ago

Sissy Compilation Public riding dildo

Sissy Compilation Public riding dildo

XVideos 1 year ago

Tori Anisston Private Show

HD 2:00 / 12:48

Tori Anisston Private Show

Flirt4Free 3 years ago

Sissygasm From Pegging

Sissygasm From Pegging

XHamster 1 year ago

Zayra Ross Private Show

Zayra Ross Private Show

Flirt4Free 4 days ago

Turkish trans slut in red lingerie and heels gets her ass oiled up and fucked hard

Turkish trans slut in red lingerie and heels gets her ass oiled up and fucked hard

XGroovy 2 years ago

Spank my big ass and use me hard

Spank my big ass and use me hard

XHamster 3 years ago

Time to Submit Sissy

60% 1:01 / 13:18

Time to Submit Sissy

FapHouse 3 months ago

Lily Wow Private Show

Lily Wow Private Show

Flirt4Free 1 year ago

Sissy Bound to Bed for Her Sissygasm

Sissy Bound to Bed for Her Sissygasm

FapHouse 2 months ago

Training myself for real Cocks

Training myself for real Cocks

MenGem 2 years ago

Try On My Panties - Sissification with SPH - Goddess Grace Divine

Try On My Panties - Sissification with SPH - Goddess Grace Divine

XHamster 2 years ago

Slut Training She Obeys What I Say You Wnana Be One

Slut Training She Obeys What I Say You Wnana Be One

XHamster 1 month ago

Lance & Christian & Master Private Show

63% HD 2:00 / 13:19

Lance & Christian & Master Private Show

Flirt4Free 3 years ago

Step Stepbro Stags On Me Urinating Revved Sissy Jerk Off Instructions

Step Stepbro Stags On Me Urinating Revved Sissy Jerk Off Instructions

TrannyGem 4 years ago

So Much Squirting! So Hot!

4K 2:00 / 10:28

So Much Squirting! So Hot!

Camster 1 month ago

Emma Devereaux Private Show

HD 2:00 / 26:53

Emma Devereaux Private Show

Camster 2 years ago

Maya Spring Party on Aug 24, 2026 - Part 4

4K 2:00 / 37:31

Maya Spring Party on Aug 24, 2026 - Part 4

Flirt4Free 3 weeks ago

TS Rianna James StrapOn

64% HD 0:10 / 13:26

TS Rianna James StrapOn

LoyalFans 4 years ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 2 years ago

Wild Sabrina Private Show

60% HD 2:00 / 5:31

Wild Sabrina Private Show

Flirt4Free 4 years ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 2 years ago

Training Session, Cock Lifting and Hairy Armpits

Training Session, Cock Lifting and Hairy Armpits

FapHouse 4 months ago

Alexxa A Private Show

HD 2:00 / 37:59

Alexxa A Private Show

Camster 2 days ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Camster 1 week ago

Horny Sissy Slut Training

Horny Sissy Slut Training

XHamster 5 years ago

Worthless sissy slave gets her tight ass ponded by mistress's BBC

Worthless sissy slave gets her tight ass ponded by mistress's BBC

XHamster 9 months ago

Angie Mendoza Private Show

Angie Mendoza Private Show

Flirt4Free 5 years ago

Angie Mendoza Private Show

HD 2:00 / 13:45

Angie Mendoza Private Show

Flirt4Free 5 years ago

SARINAANDROBIN - Ghost Park Final Chapter of Pleasure

SARINAANDROBIN - Ghost Park Final Chapter of Pleasure

XHamster 1 year ago

Master & Ithan Private Show

68% HD 2:00 / 28:44

Master & Ithan Private Show

Flirt4Free 1 year ago

William Raven Private Show

HD 2:00 / 23:33

William Raven Private Show

Flirt4Free 4 years ago

Desire Sweet Private Show

HD 2:00 / 10:49

Desire Sweet Private Show

Camster 1 month ago

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

HD 0:39 / 20:41

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

FapHouse 1 year ago

Nyl Amazonium Shar Training Wonder Woman and Power Girl Poundtown Intense Orgy

Nyl Amazonium Shar Training Wonder Woman and Power Girl Poundtown Intense Orgy

XHamster 1 year ago

messy homosexual pig servenaked manacled and bound up at his nuts with sex-toy in booty

messy homosexual pig servenaked manacled and bound up at his nuts with sex-toy in booty

Lesbian8 1 week ago

Tiara Rossi Private Show

Tiara Rossi Private Show

Camster 1 year ago

FUCK PUSSY BOY - Part 3

60% 4K 2:00 / 9:48

FUCK PUSSY BOY - Part 3

Flirt4Free 6 months ago

Femboy Gwen Tennyson in High Heels Massive Anal Creampie Cumfarts and Wedgie Anal Sex Through Her Torn Leggings

HD 0:39 / 19:35

Femboy Gwen Tennyson in High Heels Massive Anal Creampie Cumfarts and Wedgie Anal Sex Through Her Torn Leggings

FapHouse 2 weeks ago

Cum twice while riding huge corn

Cum twice while riding huge corn

XHamster 9 months ago

Black Boy Got Turn on by His Coach at the Training Section

63% HD 1:01 / 13:54

Black Boy Got Turn on by His Coach at the Training Section

FapHouse 7 months ago

Domme Mercer Latex Sissy Punished by Chastity, Fuckmachine, Slapping, Dicksucking, and Pegging

Domme Mercer Latex Sissy Punished by Chastity, Fuckmachine, Slapping, Dicksucking, and Pegging

TransTube.tv 1 year ago

Lingerie Sissy Gets Locked Onto Her Dildo Pole and Tries to Cum in Chastity

Lingerie Sissy Gets Locked Onto Her Dildo Pole and Tries to Cum in Chastity

XHamster 8 months ago

Serge3dx Training Tsunade Legendary Episode Creampie Inside the Sweet and Tight Pussy Dripping Cum Intense Pleasure, Buttocks

Serge3dx Training Tsunade Legendary Episode Creampie Inside the Sweet and Tight Pussy Dripping Cum Intense Pleasure, Buttocks

XHamster 2 years ago

Angelina Please Trains For Her Career

Angelina Please Trains For Her Career

BeMyHole 1 week ago

Ava Venom Double FemDom Sounded Ft Satanatrix and Mistress Celene

Ava Venom Double FemDom Sounded Ft Satanatrix and Mistress Celene

Clips4sale 1 year ago

Red Satin and Hot Cock Sucking and Masturbating with a Cloth at Step-auntie Lady Victoria Valente

HD 1:01 / 10:40

Red Satin and Hot Cock Sucking and Masturbating with a Cloth at Step-auntie Lady Victoria Valente

FapHouse 5 months ago

Enjoying One of My Favorite Plugs, Stretches My Cunt so Good, It Wants to Keep It in All Day Everyday. SDo That’s What I Did

51% HD 0:39 / 3:05

Enjoying One of My Favorite Plugs, Stretches My Cunt so Good, It Wants to Keep It in All Day Everyday. SDo That’s What I Did

FapHouse 4 months ago

Sissification - Sissy Trainer - Sissy - Feminization

Sissification - Sissy Trainer - Sissy - Feminization

TrannyGem 3 years ago

Luna Florez Private Show

Luna Florez Private Show

Camster 2 years ago

Sissy Fucks Me With a Strap On While Caged

Sissy Fucks Me With a Strap On While Caged

XHamster 3 years ago

Cindy take 18 inch dildo all the way in chastity

Cindy take 18 inch dildo all the way in chastity

XHamster 4 years ago

I Need It Deep

XHamster 8 months ago

Sissy Play

XHamster 11 months ago

Helen Monroy Private Show

HD 2:00 / 10:06

Helen Monroy Private Show

Flirt4Free 3 years ago

Sandy Nell Private Show

4K 2:00 / 22:32

Sandy Nell Private Show

Flirt4Free 1 week ago

Hot russian femboy big ass squirt orgasm self facial training compilation

Hot russian femboy big ass squirt orgasm self facial training compilation

AShemaleTube 1 year ago

Sissy Corgen gets fucked by fuck machine.

Sissy Corgen gets fucked by fuck machine.

XHamster 4 years ago

Khalifa Gold & Lissa Hamilton Private Show

Khalifa Gold & Lissa Hamilton Private Show

Camster 1 year ago

Desire Sweet Private Show

59% HD 2:00 / 18:13

Desire Sweet Private Show

Camster 6 days ago

60 61 62 63 64

123,897 results found

Related categories

Leashed Cage Humiliation Edging Challenge Master Handcuffed Maledom In Control Blindfolded Superhero Slave Training Prison Submissive Tied Up Spanked Worship Chastity Cage Collar Jail

Narrow your search

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

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.