Training Videos - Trans (8,978)

sissy bitch breakdown (WMV)

sissy bitch breakdown (WMV)

Clips4sale 1 year ago

SHEMALE DOMINATION - 90 - LETICIA ANTONEL & LUA - CLIP 3 OF 6

63% 0:18 / 5:04

SHEMALE DOMINATION - 90 - LETICIA ANTONEL & LUA - CLIP 3 OF 6

Clips4sale 8 months ago

Working My trannies Tight Hole

Working My trannies Tight Hole

Clips4sale 1 week ago

Trans Doll Pumps Tits and Fucks Ass

67% HD 0:10 / 16:15

Trans Doll Pumps Tits and Fucks Ass

Clips4sale 4 years ago

4K - Girl Cock Yoga Pose 7

4K 0:30 / 33:40

4K - Girl Cock Yoga Pose 7

Clips4sale 1 year ago

TS Sissy Anal Training & Creampie for Pup Sasha De Sade

68% 0:30 / 18:03

TS Sissy Anal Training & Creampie for Pup Sasha De Sade

Clips4sale 1 year ago

Transformation of the Sissy Gimp (4k)

Premium 4K 25:25

Transformation of the Sissy Gimp (4k)

Clips4sale 9 months ago

Futanari Pegging BJ Food Humiliation HD

51% HD 0:20 / 18:34

Futanari Pegging BJ Food Humiliation HD

Clips4sale 3 years ago

Sissy Dress up humiliation part 1 - Everything pink, satin & frilly

Premium HD 16:25

Sissy Dress up humiliation part 1 - Everything pink, satin & frilly

Clips4sale 4 years ago

SISSY THERAPY-FANTASY: Your First Dress Sensual Feminization

SISSY THERAPY-FANTASY: Your First Dress Sensual Feminization

Clips4sale 1 year ago

Red Pill Alpha to Sissy Whore

Premium HD 18:26

Red Pill Alpha to Sissy Whore

Clips4sale 3 months ago

Peer Pressure Pansy

66% HD 0:10 / 15:56

Peer Pressure Pansy

LoyalFans 2 years ago

Latex Doll Toy Training (1080p)

HD 0:30 / 12:46

Latex Doll Toy Training (1080p)

Clips4sale 1 year ago

Pink Sissy Diaper world with Trans StepMommy

Pink Sissy Diaper world with Trans StepMommy

Clips4sale 9 months ago

Fuck Doll Inspection And Pussy Demonstration

Fuck Doll Inspection And Pussy Demonstration

Clips4sale 4 months ago

Luna takes it deep in both ends

Premium HD 5:04

Luna takes it deep in both ends

Clips4sale 3 months ago

Mistress Sabrina's Foot Worship Session with Lauren Holland (STANDARD WMV)

Mistress Sabrina's Foot Worship Session with Lauren Holland (STANDARD WMV)

Clips4sale 1 year ago

Amuse Me Sissy Cum Slut

HD 0:10 / 14:31

Amuse Me Sissy Cum Slut

LoyalFans 3 years ago

Feminine Etiquette Interactive (4KUHD MP4)

58% HD 0:26 / 13:50

Feminine Etiquette Interactive (4KUHD MP4)

Clips4sale 1 year ago

Bimbo FuckDoll Pegged

55% 0:25 / 11:04

Bimbo FuckDoll Pegged

Clips4sale 1 year ago

Futanari Trains Her Foot Cuck To Suck & Fuck - Ft Imilia Audley

Premium HD 14:23

Futanari Trains Her Foot Cuck To Suck & Fuck - Ft Imilia Audley

Clips4sale 3 days ago

Truth or Dare

61% HD 0:11 / 38:27

Clips4sale 4 years ago

Dominant Mistress Teases Submissive in Stockings

Dominant Mistress Teases Submissive in Stockings

Clips 4 weeks ago

Brainless Bimbo Sissy Obsession

Brainless Bimbo Sissy Obsession

Clips4sale 2 years ago

RED ROOM 1: MY PERFECT RUBBER BONDAGE SLAVE Remastered HD

58% HD 0:58 / 40:01

RED ROOM 1: MY PERFECT RUBBER BONDAGE SLAVE Remastered HD

Clips4sale 8 months ago

Panties Down & Bottoms Out - Mistress Need to Pound Some Boi Pussy

Panties Down & Bottoms Out - Mistress Need to Pound Some Boi Pussy

Clips4sale 3 years ago

Dani M Love Tied, Hogtied and Tickled in Her Japanese School Uniform

69% 0:29 / 6:41

Dani M Love Tied, Hogtied and Tickled in Her Japanese School Uniform

Clips4sale 3 years ago

OILED tgirl with HUGE COCK fucks herself with BBC and CUMS

OILED tgirl with HUGE COCK fucks herself with BBC and CUMS

Clips4sale 4 months ago

The Newlyweds: First Time Feminization - Audio

The Newlyweds: First Time Feminization - Audio

Clips4sale 1 year ago

Ep1 Kiara | From Housework Fail to Cock Love & Pegging - Mistress Julia

Ep1 Kiara | From Housework Fail to Cock Love & Pegging - Mistress Julia

Clips4sale 10 months ago

Electrified She-Male (MP4 HD)

Electrified She-Male (MP4 HD)

Clips4sale 4 months ago

4K - Lusty Shower Vol 21 - Golden Strawberry Month # 6

66% 4K 0:09 / 43:48

4K - Lusty Shower Vol 21 - Golden Strawberry Month # 6

Clips4sale 10 months ago

Compilation of sissy cuckold training - Real session with two partners - BBC - Trans woman - Sissy Chastity

HD 0:59 / 32:38

Compilation of sissy cuckold training - Real session with two partners - BBC - Trans woman - Sissy Chastity

Clips4sale 7 months ago

Erica Cherry Trains Tattooed Sub Lady Lazarus PART 1

63% 4K 0:30 / 8:19

Erica Cherry Trains Tattooed Sub Lady Lazarus PART 1

Clips4sale 3 years ago

Role Play Session DID

45% HD 0:11 / 24:05

Role Play Session DID

Clips4sale 3 years ago

THE GAY AWAKENING 2 PODCAST: EPISODE #17

HD 0:10 / 24:17

THE GAY AWAKENING 2 PODCAST: EPISODE #17

LoyalFans 3 years ago

Transformation of the Sissy Gimp (HD)

63% HD 0:30 / 25:25

Transformation of the Sissy Gimp (HD)

Clips4sale 9 months ago

Clown Girl Diaper Radio Show

HD 0:25 / 19:04

Clown Girl Diaper Radio Show

Clips4sale 2 months ago

So You Want To Be a Girl? - BBW Sydney Screams Knows You Fantasize About Transitioning Into a Woman - HD 720 WMV

66% HD 0:22 / 11:04

So You Want To Be a Girl? - BBW Sydney Screams Knows You Fantasize About Transitioning Into a Woman - HD 720 WMV

Clips4sale 1 year ago

YOU WILL BE THE PRETTIEST BOY AT THE PARTY 1080p

4K 0:40 / 11:02

YOU WILL BE THE PRETTIEST BOY AT THE PARTY 1080p

Clips4sale 3 years ago

Becky punishes her Sissy Slut Michelle for not proper kitchen cleaning

HD 1:00 / 50:49

Becky punishes her Sissy Slut Michelle for not proper kitchen cleaning

Clips4sale 2 years ago

Rub Your Clitty Like the Sissy Faggot You Are

63% 0:30 / 8:47

Rub Your Clitty Like the Sissy Faggot You Are

Clips4sale 10 months ago

A Sissy in the New Black Cock Order

66% 4K 0:30 / 15:10

A Sissy in the New Black Cock Order

Clips4sale 1 year ago

Atlanta Domme Fuck-A-Palooza (MP4 HD)

66% HD 0:30 / 9:03

Atlanta Domme Fuck-A-Palooza (MP4 HD)

Clips4sale 1 year ago

Closet Sissy, gets Caged & Tag Teamed With My Trans BFF (480 MP4)

56% HD 0:29 / 10:38

Closet Sissy, gets Caged & Tag Teamed With My Trans BFF (480 MP4)

Clips4sale 3 years ago

Extreme Pleasure W Ava Venom & Gia Aquila PT 1

HD 0:30 / 28:14

Extreme Pleasure W Ava Venom & Gia Aquila PT 1

Clips4sale 3 months ago

4K - FULL CREAM COMPILATION NEO 5

62% 4K 0:14 / 38:40

4K - FULL CREAM COMPILATION NEO 5

Clips4sale 2 years ago

Boss Bitch Secretary Trained To Be A Gape Slut In Anal BDSM

HD 0:29 / 30:57

Boss Bitch Secretary Trained To Be A Gape Slut In Anal BDSM

Clips4sale 1 year ago

BISEXUAL ENCOURAGEMENT BONDAGE It’s no longer a performance—it’s submission Two big-cocked subs in spit and lust, driven to the brink by ruthless, whispered encouragement and the overwhelming

HD 0:20 / 10:03

BISEXUAL ENCOURAGEMENT BONDAGE It’s no longer a performance—it’s submission Two big-cocked subs in spit and lust, driven to the brink by ruthless, whispered encouragement and the overwhelming

Clips4sale 1 year ago

Sissy Challenge

Sissy Challenge

Clips4sale 3 years ago

You jerk off your dick for the cocks of muscular transsexuals ITA

You jerk off your dick for the cocks of muscular transsexuals ITA

Clips4sale 9 months ago

Training his ass for the first time

Training his ass for the first time

Clips4sale 1 year ago

oiled trans with JUICY ass takes BBC fuck machine LIKE A PRO

oiled trans with JUICY ass takes BBC fuck machine LIKE A PRO

Clips4sale 8 months ago

bondage strap-on training in loveswing: sissy with ballgag in latex bodysuit gets used hard by asian goddess Asuna Bloom

bondage strap-on training in loveswing: sissy with ballgag in latex bodysuit gets used hard by asian goddess Asuna Bloom

Clips4sale 10 months ago

Femsub Therapy Fantasy

56% HD 0:13 / 18:00

Femsub Therapy Fantasy

Clips4sale 2 years ago

Cock Gobbling Slut for Mistress Kendra wmv

Cock Gobbling Slut for Mistress Kendra wmv

Clips4sale 4 years ago

Double foot fisting with Aveena

64% HD 0:28 / 41:07

Double foot fisting with Aveena

Clips4sale 4 years ago

First Date Surprise Pegging

First Date Surprise Pegging

Clips4sale 1 year ago

YOU ARE THE GIRL MIND FUCK - Becoming The Girl, Sissy Training

YOU ARE THE GIRL MIND FUCK - Becoming The Girl, Sissy Training

Clips4sale 11 months ago

Dominating My Fuck Doll TS Nikki Lilith - 1080 MP4

59% HD 0:30 / 25:22

Dominating My Fuck Doll TS Nikki Lilith - 1080 MP4

Clips4sale 4 years ago

My Rubber Feminized Hubby Stage 1 (MP4)

My Rubber Feminized Hubby Stage 1 (MP4)

Clips4sale 1 year ago

Sissy BrainFuck Compilation FULL MOVIE

63% HD 0:30 / 1:13:15

Sissy BrainFuck Compilation FULL MOVIE

Clips4sale 1 year ago

Mistress Sura masturbates Mistress Tania

Premium HD 6:36

Mistress Sura masturbates Mistress Tania

Clips4sale 2 years ago

CD Mila CBT MOV

CD Mila CBT MOV

Clips4sale 4 months ago

Step-Mommy comes home to tease her PetGirl- Variety Itsol

Step-Mommy comes home to tease her PetGirl- Variety Itsol

Clips4sale 1 year ago

POV: Sissy Bussy Training mp4

57% 0:08 / 7:21

POV: Sissy Bussy Training mp4

Clips4sale 1 year ago

Such Sloppy Anal Sluts

62% 0:11 / 9:55

Such Sloppy Anal Sluts

Clips4sale 2 years ago

Gagged Sissy Loves Drooling

70% HD 0:10 / 13:16

Gagged Sissy Loves Drooling

Clips4sale 4 years ago

POV: Your Sissy Diagnosis (And What To Do Next)

POV: Your Sissy Diagnosis (And What To Do Next)

Clips4sale 1 year ago

SISSY PRISON - New Prisoner *MOV*

4K 0:45 / 20:47

SISSY PRISON - New Prisoner *MOV*

Clips4sale 3 months ago

rave bunny gets stretched

65% 0:30 / 19:12

rave bunny gets stretched

Clips4sale 7 months ago

Making My Step-Brother A Step-Sister! Sissification, Feminization, Height Humiliation for My Short Bullied Step-Bro

Making My Step-Brother A Step-Sister! Sissification, Feminization, Height Humiliation for My Short Bullied Step-Bro

Clips4sale 4 months ago

P9 AUDITION LATEX CATSUIT RAW FUCKING SLING SUB DUNGEON WHORE

HD 0:21 / 10:14

P9 AUDITION LATEX CATSUIT RAW FUCKING SLING SUB DUNGEON WHORE

Clips4sale 2 months ago

SHEMALE DOMINATION - 90 - LETICIA ANTONEL & LUA - CLIP 2 OF 6

SHEMALE DOMINATION - 90 - LETICIA ANTONEL & LUA - CLIP 2 OF 6

Clips4sale 8 months ago

My futa dick is bigger than yours !- SPH

63% HD 0:13 / 10:48

My futa dick is bigger than yours !- SPH

Clips4sale 4 years ago

Bound And Teased Nylon Sissy Doll (MP4)

55% 0:13 / 9:54

Bound And Teased Nylon Sissy Doll (MP4)

Clips4sale 1 year ago

Sissy Cartoon Screen Saver

57% HD 0:26 / 5:48

Sissy Cartoon Screen Saver

Clips4sale 4 years ago

I know your secret - You're Just a Toy for Real Men WMV

I know your secret - You're Just a Toy for Real Men WMV

Clips4sale 2 years ago

4K - Lusty Shower Vol 20

4K 0:28 / 26:38

4K - Lusty Shower Vol 20

Clips4sale 1 year ago

P3 OLIVE GREEN LATEX CATSUIT DEEPTHROAT SUB IN STRAIGHT JACKET

77% 4K 0:23 / 10:14

P3 OLIVE GREEN LATEX CATSUIT DEEPTHROAT SUB IN STRAIGHT JACKET

Clips4sale 2 years ago

P4 SHEMALE MASTER ON SLAVE DEEPTHROAT UNBELIEVABLE HOW DEEP HE CAN TAKE IT

P4 SHEMALE MASTER ON SLAVE DEEPTHROAT UNBELIEVABLE HOW DEEP HE CAN TAKE IT

Clips4sale 3 years ago

Twice the Fists, Twice the Fun - Goddess Lilith, Lady Vi, Ava Venom anal fisting clip

53% 0:30 / 12:00

Twice the Fists, Twice the Fun - Goddess Lilith, Lady Vi, Ava Venom anal fisting clip

Clips4sale 1 year ago

SISSY SLUT BIMBO MESMERIZE

59% HD 0:10 / 13:20

SISSY SLUT BIMBO MESMERIZE

LoyalFans 2 years ago

Cum Eating Panties Slut (MP4)

66% 0:13 / 13:30

Cum Eating Panties Slut (MP4)

Clips4sale 2 years ago

Prisoner of the Matriarchy: Warrior Captured And Pegged

62% 0:11 / 15:12

Prisoner of the Matriarchy: Warrior Captured And Pegged

Clips4sale 2 years ago

Aveena slut academy E1

66% HD 0:29 / 46:01

Aveena slut academy E1

Clips4sale 4 years ago

Miss Devoras Blow Job Tips for Sluts: BBW MiLF Domme Teaches you how to suck dick POV 720 Version

Miss Devoras Blow Job Tips for Sluts: BBW MiLF Domme Teaches you how to suck dick POV 720 Version

Clips4sale 2 years ago

SHEMALE DOMINATION - 90 - LETICIA ANTONEL & LUA - CLIP 1 OF 6

SHEMALE DOMINATION - 90 - LETICIA ANTONEL & LUA - CLIP 1 OF 6

Clips4sale 8 months ago

Sub Torment 3

Clips4sale 2 years ago

Lefty Women End Patriarchy by CBT

Lefty Women End Patriarchy by CBT

Clips4sale 1 year ago

Self Sucking Cum Slut

Self Sucking Cum Slut

Clips4sale 4 months ago

SISSY STAR BATTLES Diaper Mission S155Y Lunar Legion Campaign Part 3

HD 0:46 / 22:21

SISSY STAR BATTLES Diaper Mission S155Y Lunar Legion Campaign Part 3

Clips4sale 1 month ago

SLUT MICHELLES BBC SUCKING LESSON

70% 4K 0:25 / 26:32

SLUT MICHELLES BBC SUCKING LESSON

Clips4sale 3 years ago

COCK TEASE SPH!

Premium HD 15:20

COCK TEASE SPH!

Clips4sale 2 months ago

Sizeable Dilemma1

46% HD 0:10 / 13:13

Sizeable Dilemma1

LoyalFans 5 years ago

4K What If I Had A Penis

4K 0:09 / 12:01

4K What If I Had A Penis

Clips4sale 3 months ago

Weak for Tranny's Cock and Sperm

Premium HD 11:59

Weak for Tranny's Cock and Sperm

Clips4sale 4 years ago

My friend Ts Girl Dani Marks humiliates my husband and has a Sissy

My friend Ts Girl Dani Marks humiliates my husband and has a Sissy

Clips4sale 1 year ago

sissy makeover 2 - sissification, feminisation, encouraged bi, exposure, slave task trainning, verbal humiliation

sissy makeover 2 - sissification, feminisation, encouraged bi, exposure, slave task trainning, verbal humiliation

Clips4sale 1 year ago

Immersive POV: Feminization and Bisexual Training - Mistress Julia

63% HD 0:10 / 15:36

Immersive POV: Feminization and Bisexual Training - Mistress Julia

LoyalFans 1 year ago

[ Full Version ] Serve My Ladyboy Friend 2 ft Mari Ayanami

65% HD 0:30 / 54:29

[ Full Version ] Serve My Ladyboy Friend 2 ft Mari Ayanami

Clips4sale 10 months ago

Sasha's Obedient Sissy Slave (WMV)

43% 0:12 / 17:08

Sasha's Obedient Sissy Slave (WMV)

Clips4sale 1 year ago

(517) Sissygasm: Crossdresser Anal Masturbation with Glass Dildo and Hands-Free Orgasm - Zoulette (4K, WMV)

(517) Sissygasm: Crossdresser Anal Masturbation with Glass Dildo and Hands-Free Orgasm - Zoulette (4K, WMV)

Clips4sale 1 year ago

FUTA Dommes Train your Holes - SD - featuring Cozy Gams and Jane Judge, in this femdom strapon facefuck POV scene with a real life futanari and Jane's big fat strapon training your holes to be a good slut for them on Janes Dungeon

FUTA Dommes Train your Holes - SD - featuring Cozy Gams and Jane Judge, in this femdom strapon facefuck POV scene with a real life futanari and Jane's big fat strapon training your holes to be a good slut for them on Janes Dungeon

Clips4sale 1 year ago

Girls Night Out

Premium HD 20:24

Girls Night Out

Clips4sale 4 weeks ago

Sissy Poses Become Permanent

Sissy Poses Become Permanent

LoyalFans 3 years ago

More than she Bargained For, Part 3: Girl-Girl Strapon

More than she Bargained For, Part 3: Girl-Girl Strapon

Clips4sale 8 months ago

Live Your Life As A Woman WMV

Live Your Life As A Woman WMV

Clips4sale 4 years ago

Sissy Slut Dress up and Pegging Playtime

Premium 4K 24:22

Sissy Slut Dress up and Pegging Playtime

Clips4sale 3 weeks ago

Sissy Mesmerize - kendra james, femdom, joi wmv

57% HD 0:11 / 16:20

Sissy Mesmerize - kendra james, femdom, joi wmv

Clips4sale 3 years ago

Become A Cuck Slave To A Hot Wife, Extreme Cuckold Slave Slut Programming BETA Mesmerize

55% 0:30 / 24:02

Become A Cuck Slave To A Hot Wife, Extreme Cuckold Slave Slut Programming BETA Mesmerize

Clips4sale 1 year ago

Lime squats on his big horsecock and can't hold sissygasm

Lime squats on his big horsecock and can't hold sissygasm

Clips4sale 6 months ago

First Date Sissy

42% 0:30 / 12:39

First Date Sissy

Clips4sale 1 year ago

Stepmommy's Dirtiest BBC Faggot

65% 0:21 / 11:40

Stepmommy's Dirtiest BBC Faggot

Clips4sale 1 year ago

Becoming Candy: Permanent Sissy Identity Imprint

62% HD 0:30 / 42:17

Becoming Candy: Permanent Sissy Identity Imprint

Clips4sale 7 months ago

High Heels Love Tongue Worship (1080p)

High Heels Love Tongue Worship (1080p)

Clips4sale 3 weeks ago

Shoe Worship On The Shoe Chair (WMV HD)

Shoe Worship On The Shoe Chair (WMV HD)

Clips4sale 3 years ago

The right moment to change your GENDER ! - gender transformation , transgender

The right moment to change your GENDER ! - gender transformation , transgender

Clips4sale 3 years ago

Sissy tutorial step one

HD 0:30 / 13:18

Sissy tutorial step one

Clips4sale 1 year ago

Tania training slave part 2

67% 4K 0:10 / 11:26

Tania training slave part 2

Clips4sale 2 years ago

9 10 11 12 13

8,978 results found

Related categories

Edging Leashed Goon Spandex Collar Cage Chastity Chastity Cage Master Slave Training CMNF Spanked Worship Handcuffed Suspension Mud Flexing Superhero Foreskin Mask

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 throat training slut training bi training slave training training anal anal training joi sissy anal training 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.