Training Videos - Trans (8,956)

Happy She-Cock Eater

67% HD 0:36 / 13:32

Happy She-Cock Eater

Clips4sale 5 months ago

Permanent Feminization: Encouraged Estrogen

64% HD 0:10 / 8:17

Permanent Feminization: Encouraged Estrogen

LoyalFans 11 months ago

Sissy School (1080)

HD 0:21 / 10:04

Sissy School (1080)

Clips4sale 3 years ago

Ava Venom & Natalie V Double Dom SpitRoast Cowboy Strapon

Ava Venom & Natalie V Double Dom SpitRoast Cowboy Strapon

Clips4sale 1 year ago

??X??X??? Halter neck x pleated skirt x stockings

63% 0:30 / 31:52

??X??X??? Halter neck x pleated skirt x stockings

Clips4sale 1 year ago

Teacher Gets Top

HD 0:30 / 31:17

Teacher Gets Top

Clips4sale 2 years ago

Gayboi Nipples Sissy Beta Humiliation Erotic Audio by Tara Smith Gay Encouragement

50% 0:25 / 7:29

Gayboi Nipples Sissy Beta Humiliation Erotic Audio by Tara Smith Gay Encouragement

Clips4sale 2 years ago

Trans Girl Fucks Your MTF Pussy

HD 0:25 / 12:26

Trans Girl Fucks Your MTF Pussy

Clips4sale 1 month ago

Your Roommate is your Sissy Mistress for Big Black Cock

4K 0:28 / 11:49

Your Roommate is your Sissy Mistress for Big Black Cock

Clips4sale 1 year ago

Feminized Irreversibly

66% 0:11 / 8:38

Feminized Irreversibly

Clips4sale 3 years ago

THE ULTIMATE SISSY DIAPER HUMILIATION: Two Goddesses Break a Trans Domme - 1080p UHD - FT Goddess Marcy, Lucy Puddles and Goddess Rose

HD 0:30 / 22:18

THE ULTIMATE SISSY DIAPER HUMILIATION: Two Goddesses Break a Trans Domme - 1080p UHD - FT Goddess Marcy, Lucy Puddles and Goddess Rose

Clips4sale 3 months ago

Good Dolls Need Cock Training

61% 0:30 / 12:50

Good Dolls Need Cock Training

Clips4sale 1 year ago

Slut Gray Perrier used at Gloryhole

Premium HD 13:36

Slut Gray Perrier used at Gloryhole

Clips4sale 3 weeks ago

Good Girl Cum Ritual for My Sissy!

Good Girl Cum Ritual for My Sissy!

Clips4sale 7 months ago

Foot Worship Audition: Nancy Serves Dominant Cher- 1080p

Foot Worship Audition: Nancy Serves Dominant Cher- 1080p

Clips4sale 1 month ago

Another round, another level—MISTRESS FETISHTRANSEXUAL with Subs two throbbing cocks, one hungry mouth, and no breaks as encouragement fuels the nonstop

HD 0:21 / 10:17

Another round, another level—MISTRESS FETISHTRANSEXUAL with Subs two throbbing cocks, one hungry mouth, and no breaks as encouragement fuels the nonstop

Clips4sale 1 year ago

Fuck your Ass for Goddess - Sissy Anal JOI + Strapon by Goddess Nikki Kit

Fuck your Ass for Goddess - Sissy Anal JOI + Strapon by Goddess Nikki Kit

LoyalFans 1 year ago

BIMBOFICATION 101 1080p

BIMBOFICATION 101 1080p

Clips4sale 2 years ago

BBC Training the Soggy Sissy: ThePrincessLuxy Reinforces and Threatens to Expose your True Place in the Sexual Heirarchy with Shemale Affirmations, Wet Diaper Humping, and Anal Preparation

HD 0:25 / 18:00

BBC Training the Soggy Sissy: ThePrincessLuxy Reinforces and Threatens to Expose your True Place in the Sexual Heirarchy with Shemale Affirmations, Wet Diaper Humping, and Anal Preparation

Clips4sale 7 months ago

Benched and Broken In

Benched and Broken In

Clips4sale 3 months ago

Your Gender Failed at Pleasure

Your Gender Failed at Pleasure

Clips4sale 8 months ago

Pride Month Femme Encouragement

63% HD 0:11 / 11:45

Pride Month Femme Encouragement

Clips4sale 3 years ago

CHEAT WITH A SHEMALE

CHEAT WITH A SHEMALE

Clips4sale 1 year ago

Sissy Punishment

HD 0:19 / 11:40

Sissy Punishment

Clips4sale 2 years ago

PRACTICE SUCKING MY COCK

Premium HD 5:46

PRACTICE SUCKING MY COCK

Clips4sale 1 month ago

Convince Us You're a Girl - POV Pegging

58% 0:30 / 18:10

Convince Us You're a Girl - POV Pegging

Clips4sale 1 year ago

(608) Sissygasm Compilation #01: Crossdresser’s Hands-Free Orgasms - Zoulette (1080p)

(608) Sissygasm Compilation #01: Crossdresser’s Hands-Free Orgasms - Zoulette (1080p)

Clips4sale 1 year ago

End Your European Heritage

53% HD 0:30 / 14:57

End Your European Heritage

Clips4sale 11 months ago

Straight Again… Until You Press Play

Straight Again… Until You Press Play

Clips4sale 8 months ago

Welcome to the Cock Worship Cult

HD 0:30 / 35:05

Welcome to the Cock Worship Cult

Clips4sale 7 months ago

FUTA CUSTOM 4 POV: I'm Making You Surrender

FUTA CUSTOM 4 POV: I'm Making You Surrender

Clips4sale 4 years ago

Shortalls Catgirl Cutie Cosplay Cumming

64% 0:11 / 13:13

Shortalls Catgirl Cutie Cosplay Cumming

Clips4sale 3 years ago

Sissy Slave Ruining and Cum Eating

62% HD 0:10 / 25:13

Sissy Slave Ruining and Cum Eating

Clips4sale 4 years ago

EXPOSING SLUT MICHELLE

63% HD 0:10 / 10:41

EXPOSING SLUT MICHELLE

LoyalFans 3 years ago

4K - Forest elf's cum squeezing magic

68% 4K 0:16 / 30:29

4K - Forest elf's cum squeezing magic

Clips4sale 2 years ago

Sissy Fancy Princess - full version

HD 0:18 / 49:43

Sissy Fancy Princess - full version

Clips4sale 1 year ago

Body Swap with Stalker & Turned into Slut

Body Swap with Stalker & Turned into Slut

Clips4sale 1 year ago

Sissy Task for Sissies

Sissy Task for Sissies

LoyalFans 1 year ago

Tranny Porn Is Gay

Premium HD 5:01

Tranny Porn Is Gay

Clips4sale 1 month ago

Sissy Slut Dorathy Part 2 Punishment Panties

Sissy Slut Dorathy Part 2 Punishment Panties

Clips4sale 3 years ago

Not Quite Your Diaper Fairy Tale

55% 0:29 / 13:08

Not Quite Your Diaper Fairy Tale

Clips4sale 3 years ago

RENEES FOOTSLAVE(S) - PART 1

65% 0:08 / 7:39

RENEES FOOTSLAVE(S) - PART 1

Clips4sale 5 years ago

Blind Date gone wrong - Sissy seduces a BBC

57% 0:11 / 20:06

Blind Date gone wrong - Sissy seduces a BBC

Clips4sale 2 years ago

Being a Girl Is More Fun - 4K MP4

4K 0:17 / 10:29

Being a Girl Is More Fun - 4K MP4

Clips4sale 1 year ago

Sissy Shopping Rules for Good Girls – Feminization Training by Goddess Nikki Kit

63% HD 0:20 / 5:04

Sissy Shopping Rules for Good Girls – Feminization Training by Goddess Nikki Kit

Clips4sale 1 year ago

MILF1866 - Pegging the Bully: Rachel Steele & London River’s Femdom Justice P2

66% HD 0:23 / 17:21

MILF1866 - Pegging the Bully: Rachel Steele & London River’s Femdom Justice P2

Clips4sale 1 year ago

futa femdom sissy self-sucking facial and pegging - HD - wmv

57% HD 0:30 / 6:01

futa femdom sissy self-sucking facial and pegging - HD - wmv

Clips4sale 3 years ago

Maid Into A Slut - Erica Cherry And Sinn Sage WMV

60% 0:20 / 31:42

Maid Into A Slut - Erica Cherry And Sinn Sage WMV

Clips4sale 3 years ago

SheMale Evolution - Part 3

57% HD 0:15 / 21:17

SheMale Evolution - Part 3

Clips4sale 2 years ago

Get used by shemale Mistress - Latex Dominaton in VR 3D 4K

4K 0:21 / 13:35

Get used by shemale Mistress - Latex Dominaton in VR 3D 4K

Clips4sale 4 years ago

Locktober - Plap those pathetic balls

64% 0:30 / 10:52

Locktober - Plap those pathetic balls

Clips4sale 11 months ago

Never Touching Pussy Again - Craving Only BBC Mind Remolding 20 min (MaleDom)

Never Touching Pussy Again - Craving Only BBC Mind Remolding 20 min (MaleDom)

Clips4sale 1 year ago

Latex sissy tease - Ass fucked in chastity

Latex sissy tease - Ass fucked in chastity

Clips4sale 2 years ago

Misty Teases Nancy with Intense Foot Worship and Control (HD 1080p MP4)

HD 0:15 / 14:21

Misty Teases Nancy with Intense Foot Worship and Control (HD 1080p MP4)

Clips4sale 1 year ago

You are Genetically a Sissy

4K 0:29 / 14:36

You are Genetically a Sissy

Clips4sale 1 year ago

No Sissy Trany Slut of Mine!!!

No Sissy Trany Slut of Mine!!!

Clips4sale 1 year ago

5 must-have sex toys for sissies - Femdom sissy feminization

HD 0:27 / 15:34

5 must-have sex toys for sissies - Femdom sissy feminization

Clips4sale 9 months ago

SHEMALE DOMINATION - 90 - LETICIA ANTONEL & LUA - FULL VERSION

SHEMALE DOMINATION - 90 - LETICIA ANTONEL & LUA - FULL VERSION

Clips4sale 8 months ago

caged TRANS egirl fills her HOLE with TENTACLE CREAM PIES

caged TRANS egirl fills her HOLE with TENTACLE CREAM PIES

Clips4sale 4 months ago

Trans Sluts Anal Limits Unlocked: Crystal Thayer's Hole Gaped by Fuck Machine

51% HD 0:10 / 33:33

Trans Sluts Anal Limits Unlocked: Crystal Thayer's Hole Gaped by Fuck Machine

LoyalFans 5 months ago

Rubberslave fucked by TS Yakira and Mistress Susi FullHD

HD 0:34 / 15:44

Rubberslave fucked by TS Yakira and Mistress Susi FullHD

Clips4sale 4 years ago

Gangbang Slut Training - IMPOSED BI, MAKE ME GAY by Goddess Ada

65% HD 0:28 / 10:49

Gangbang Slut Training - IMPOSED BI, MAKE ME GAY by Goddess Ada

Clips4sale 1 year ago

goon your sissy clit to loser porn

61% 0:29 / 14:46

goon your sissy clit to loser porn

Clips4sale 4 years ago

Degraded By Wearing Pretty Girly Panties

Degraded By Wearing Pretty Girly Panties

Clips4sale 2 years ago

Man Catcher Part 7 *MOV*

66% HD 0:18 / 11:16

Man Catcher Part 7 *MOV*

Clips4sale 2 years ago

Femsub Therapy Fantasy

56% HD 0:13 / 18:00

Femsub Therapy Fantasy

Clips4sale 2 years ago

Futanari Pegging BJ Food Humiliation HD

51% HD 0:20 / 18:34

Futanari Pegging BJ Food Humiliation HD

Clips4sale 3 years ago

FOOT SLAVE IS A SISSY

FOOT SLAVE IS A SISSY

Clips4sale 1 year ago

Sissification And Rope Bondage For Nosey Step-Brother (low res mp4)

56% HD 0:32 / 26:57

Sissification And Rope Bondage For Nosey Step-Brother (low res mp4)

Clips4sale 2 years ago

Sorority Girls StrapOn Hazing

60% HD 0:10 / 13:01

Sorority Girls StrapOn Hazing

LoyalFans 1 year ago

You're Our Feminized Bitch

You're Our Feminized Bitch

Clips4sale 1 year ago

Dressing Sissies For Real Men To Mock (SD MP4)

4K 0:31 / 15:17

Dressing Sissies For Real Men To Mock (SD MP4)

Clips4sale 11 months ago

SPH: Feminizing You & Discovering Your SMALL DICK!

69% HD 0:15 / 10:20

SPH: Feminizing You & Discovering Your SMALL DICK!

Clips4sale 4 years ago

Sissy Chastity Tease and Styling wmv

HD 0:11 / 13:22

Sissy Chastity Tease and Styling wmv

Clips4sale 4 years ago

Double Layer Latex CBT (1080p)

HD 0:11 / 12:13

Double Layer Latex CBT (1080p)

Clips4sale 3 years ago

Suck Off Your Futa Step-Mommy & GF with CEI

62% 4K 0:30 / 10:51

Suck Off Your Futa Step-Mommy & GF with CEI

Clips4sale 1 year ago

A Slut for Her Nylon Feet (MP4)

62% 0:13 / 12:41

A Slut for Her Nylon Feet (MP4)

Clips4sale 2 years ago

Filthy Piggy Butthole - Queer Bunny Babe and Sinn Sage WMV

66% HD 0:19 / 20:25

Filthy Piggy Butthole - Queer Bunny Babe and Sinn Sage WMV

Clips4sale 4 years ago

First Time Crossdressing: Lingerie Shopping to Hotel Room JOI CEI No Humiliation Gentle Femdom Jerk Off Instructions Butt Plug Prostate Play

47% 0:30 / 17:59

First Time Crossdressing: Lingerie Shopping to Hotel Room JOI CEI No Humiliation Gentle Femdom Jerk Off Instructions Butt Plug Prostate Play

Clips4sale 1 year ago

Sissy Dream Date

HD 0:29 / 15:21

Sissy Dream Date

Clips4sale 4 years ago

Sissy Bride Wedding Day Part 1 Dressed and Locked

57% 0:11 / 6:14

Sissy Bride Wedding Day Part 1 Dressed and Locked

Clips4sale 3 years ago

Sissy Club Slut: Femdom Fisting, Pegging, Dick Sticking Part 2 of 2 (1080p)

60% HD 0:22 / 29:58

Sissy Club Slut: Femdom Fisting, Pegging, Dick Sticking Part 2 of 2 (1080p)

Clips4sale 2 years ago

Prison or a Sissy Diaper Ballerina

52% 0:30 / 16:26

Prison or a Sissy Diaper Ballerina

Clips4sale 1 year ago

Mean Stepmommy Pegs You

Mean Stepmommy Pegs You

Clips4sale 1 year ago

4K - HUGE cumshot in school swimsuit

65% 4K 0:08 / 22:09

4K - HUGE cumshot in school swimsuit

Clips4sale 3 years ago

Training Stepmommy's Sissy Faggot

58% HD 0:10 / 9:22

Training Stepmommy's Sissy Faggot

LoyalFans 1 year ago

Nara and TS Sabrina Prezotte humiliate and fuck her cuckold (720 EN-sub)

61% HD 0:30 / 20:26

Nara and TS Sabrina Prezotte humiliate and fuck her cuckold (720 EN-sub)

Clips4sale 2 years ago

Rubber Female Mask Crossdresser Gets Fucked by Strap-on in Midair! Anal Fisting!

65% HD 0:11 / 36:30

Rubber Female Mask Crossdresser Gets Fucked by Strap-on in Midair! Anal Fisting!

Clips4sale 4 years ago

Cross Examination (HD MP4) Tilly McReese: Crossdressing, Sissification, Nylon, Feminization, Femdom copy

HD 0:37 / 15:28

Cross Examination (HD MP4) Tilly McReese: Crossdressing, Sissification, Nylon, Feminization, Femdom copy

Clips4sale 1 month ago

THE GAY AWAKENING 2 PODCAST: EPISODE #17

HD 0:10 / 24:17

THE GAY AWAKENING 2 PODCAST: EPISODE #17

LoyalFans 3 years ago

Locked Pink Latex Bimbo Slut Shaking Sissygasm on Huge Dildo - SD wmv

Locked Pink Latex Bimbo Slut Shaking Sissygasm on Huge Dildo - SD wmv

Clips4sale 2 years ago

DommeMommy B helps your through your Sissy Girl Transformation

DommeMommy B helps your through your Sissy Girl Transformation

Clips4sale 1 year ago

READY FOR THAT REAL COCK

READY FOR THAT REAL COCK

LoyalFans 4 years ago

Feminine Etiquette Interactive (4KUHD MP4)

58% HD 0:26 / 13:50

Feminine Etiquette Interactive (4KUHD MP4)

Clips4sale 1 year ago

Reject Masculinity, Embrace Your Inner Sissy Slut!

61% HD 0:31 / 11:36

Reject Masculinity, Embrace Your Inner Sissy Slut!

Clips4sale 1 year ago

sissy bitch breakdown (WMV)

sissy bitch breakdown (WMV)

Clips4sale 1 year ago

CROSSDRESSER BONDAGE + EDGING PLAY - Bounded And Edged Erotic Play [Female Power Play] [Bondage] [Restraint] [Bounded]

CROSSDRESSER BONDAGE + EDGING PLAY - Bounded And Edged Erotic Play [Female Power Play] [Bondage] [Restraint] [Bounded]

Clips4sale 1 year ago

Sissy Trapped in my Basement

HD 0:30 / 11:29

Sissy Trapped in my Basement

Clips4sale 1 month ago

Fuckdoll Learns Endurance (4k)

65% 4K 0:30 / 30:36

Fuckdoll Learns Endurance (4k)

Clips4sale 1 year ago

Working My trannies Tight Hole

Working My trannies Tight Hole

Clips4sale 1 week ago

Full Sissy Play - G041 2K

Full Sissy Play - G041 2K

Clips4sale 7 months ago

Bisexual encouragement blowing Sissy Doll whore from Prague

Premium 4K 8:02

Bisexual encouragement blowing Sissy Doll whore from Prague

Clips4sale 2 months ago

Sybian Slut Overload – Fisting, Pegging & Strap-On Domination Orgy

55% 0:30 / 28:23

Sybian Slut Overload – Fisting, Pegging & Strap-On Domination Orgy

Clips4sale 1 year ago

Luna takes it deep in both ends

Premium HD 5:04

Luna takes it deep in both ends

Clips4sale 3 months ago

Take My Girl Cock Fucked By Your Futa Mistress

66% 4K 0:30 / 11:46

Take My Girl Cock Fucked By Your Futa Mistress

Clips4sale 8 months ago

SISSY THERAPY-FANTASY: Your First Dress Sensual Feminization

SISSY THERAPY-FANTASY: Your First Dress Sensual Feminization

Clips4sale 1 year ago

Bnwo Ai Training - Mistress Shows you the Future

63% 0:30 / 13:20

Bnwo Ai Training - Mistress Shows you the Future

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

4K - DECENT HANDJOB DIRTY CUMSHOT with LEWD ASMR

4K 0:08 / 33:16

4K - DECENT HANDJOB DIRTY CUMSHOT with LEWD ASMR

Clips4sale 2 years ago

Slut Academy Pegging and Strap-on blowjob with TS girl - 4K | Demoness Luna, JuliaTS

63% 4K 0:30 / 17:46

Slut Academy Pegging and Strap-on blowjob with TS girl - 4K | Demoness Luna, JuliaTS

Clips4sale 10 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

StepMommys Little Fuckpup: Cute Puppy Play Anal Sex and Blowjob Deepthroat with Petite Furry Little and Amazon Trans Woman Stepmom

61% 0:10 / 15:08

StepMommys Little Fuckpup: Cute Puppy Play Anal Sex and Blowjob Deepthroat with Petite Furry Little and Amazon Trans Woman Stepmom

Clips4sale 1 year 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

Piss Hole Training

Piss Hole Training

Clips4sale 6 months ago

Sissy Tgirl Kassandra gets bullied and trained at BBCU with Lady Anaconda and Lady Viper 🖤🎀

63% HD 0:10 / 25:59

Sissy Tgirl Kassandra gets bullied and trained at BBCU with Lady Anaconda and Lady Viper 🖤🎀

LoyalFans 6 months ago

Truth or Dare

61% HD 0:11 / 38:27

Clips4sale 4 years 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

FemDaddy's Biggest Dicks Gangbang POV by Goddess Kyaa - 720p MP4

HD 0:17 / 20:06

FemDaddy's Biggest Dicks Gangbang POV by Goddess Kyaa - 720p MP4

Clips4sale 3 years ago

My New Sissy Anal Slut

HD 0:10 / 25:13

My New Sissy Anal Slut

LoyalFans 3 years ago

Brainless Bimbo Sissy Obsession

Brainless Bimbo Sissy Obsession

Clips4sale 2 years ago

8 9 10 11 12

8,956 results found

Related categories

Edging Leashed Collar Cage Goon Chastity Spandex Master Chastity Cage Slave Training CMNF Spanked Handcuffed Dungeon Suspension Maledom Submissive Mud Bondage Mask

Narrow your search

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

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.