Training Videos - Trans (9,048)

SISSIES DESERVE THIS

HD 0:11 / 12:54

SISSIES DESERVE THIS

Clips4sale 6 months ago

Feminized Sissy Slave BATTERED - Full Version

HD 0:30 / 27:43

Feminized Sissy Slave BATTERED - Full Version

Clips4sale 8 months ago

Papers NOW Sissy

Papers NOW Sissy

Clips4sale 6 months ago

SISSY NEEDS PRACTICE

SISSY NEEDS PRACTICE

Clips4sale 9 months ago

Sissified blowjob training WMV

HD 0:25 / 13:15

Sissified blowjob training WMV

Clips4sale 6 months ago

Sissy Training - Relax, Its Just A Little Dress Up - Mari Merlowe

Sissy Training - Relax, Its Just A Little Dress Up - Mari Merlowe

Clips4sale 6 months ago

ULTIMATE EXTREME SISSIFICATION - Sissy Training [Sissified] [Sissy Mesmerize] [Sissymaid] [Sissy]

HD 0:30 / 53:58

ULTIMATE EXTREME SISSIFICATION - Sissy Training [Sissified] [Sissy Mesmerize] [Sissymaid] [Sissy]

Clips4sale 2 months ago

My Vagina POV Trance Jealousy Mind Fuck

My Vagina POV Trance Jealousy Mind Fuck

Clips4sale 2 months ago

SISSY STAR BATTLES S155Y Diaper Mission Lunar Legion Campaign Part 2

HD 0:41 / 20:21

SISSY STAR BATTLES S155Y Diaper Mission Lunar Legion Campaign Part 2

Clips4sale 2 months ago

FTM Training To Take Big Cocks Level 3 | Trans Twink Cobalt FTM Fucks His Creamy Boy Pussy With HUGE Dildo Using Vibrator On His Big Clit Until Orgasm

Premium HD 7:57

FTM Training To Take Big Cocks Level 3 | Trans Twink Cobalt FTM Fucks His Creamy Boy Pussy With HUGE Dildo Using Vibrator On His Big Clit Until Orgasm

Clips4sale 2 months ago

Anal Speculum & Eggs Insertion

Premium HD 10:24

Anal Speculum & Eggs Insertion

Clips4sale 2 months ago

The Natural Order: Asian Brat Girl ThePrincessLuxy walks a Married husband through his first Bull night and coaxes him down into a Sissy maid while showing his Wife how to Worship a real man with Cuckold humiliation, Hotwife awakening

Premium HD 11:04

The Natural Order: Asian Brat Girl ThePrincessLuxy walks a Married husband through his first Bull night and coaxes him down into a Sissy maid while showing his Wife how to Worship a real man with Cuckold humiliation, Hotwife awakening

Clips4sale 3 months ago

Bianca Reis - TGirls Experience 33

Bianca Reis - TGirls Experience 33

Erotik 4 years ago

Providing a Break from the Grind

Providing a Break from the Grind

Clips4sale 2 weeks ago

Crate Training Day 2 - Mindfuck JOI

Premium HD 18:10

Crate Training Day 2 - Mindfuck JOI

Clips4sale 1 month ago

Humiliation 280-wmv

HD 0:25 / 17:27

Humiliation 280-wmv

Clips4sale 3 weeks ago

Such a Good T-Girl Plaything! (Ryley Rails Fucks Piper XO)

Such a Good T-Girl Plaything! (Ryley Rails Fucks Piper XO)

Clips4sale 1 week ago

Brittany Andrews Teaches You How To Become A Naughty Cock Sucker!

Brittany Andrews Teaches You How To Become A Naughty Cock Sucker!

Clips 2 weeks ago

Taming the Pony: A Kinky Queer 18-Person Orgy

4K 0:25 / 33:52

Taming the Pony: A Kinky Queer 18-Person Orgy

Clips4sale 2 years ago

Throat Dominator 2

66% 0:05 / 2:13

Throat Dominator 2

Clips4sale 2 years ago

Fuck machine anal training

Fuck machine anal training

Clips4sale 2 years ago

Stretching a Sissy with a 10" Dildo Before I Fuck Him with My Fist

Stretching a Sissy with a 10" Dildo Before I Fuck Him with My Fist

Clips4sale 2 years ago

Day 23 Sissy training programme: Choosing clothes as a sissy

HD 0:30 / 21:51

Day 23 Sissy training programme: Choosing clothes as a sissy

Clips4sale 1 year 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

Full Sissy Play - G041 2K

Full Sissy Play - G041 2K

Clips4sale 7 months ago

TS Sucker For Ebony Feet Receive Tease & Ballbusting | MahoganyQen with Julia Masakova

57% 4K 0:18 / 14:12

TS Sucker For Ebony Feet Receive Tease & Ballbusting | MahoganyQen with Julia Masakova

Clips4sale 7 months ago

Jasmine Dlight Mistress Luciana Warming up with a giant Butt Plug

Jasmine Dlight Mistress Luciana Warming up with a giant Butt Plug

Clips4sale 7 months ago

BBW Goddess Destroys Jade Storm's Ass in Fuckbox- Finger Stretching, Multi-Angle Big Cock Pounding, Shaking Moans

HD 0:10 / 13:09

BBW Goddess Destroys Jade Storm's Ass in Fuckbox- Finger Stretching, Multi-Angle Big Cock Pounding, Shaking Moans

LoyalFans 7 months ago

FUTA ADDICTION

Clips4sale 10 months ago

TURNED OUT - Sissification Mesmerize [Sissy] [Sissy Training] [Gender Transformation] Mind Fuck

TURNED OUT - Sissification Mesmerize [Sissy] [Sissy Training] [Gender Transformation] Mind Fuck

Clips4sale 2 years ago

Wander Into The VORE Goddess Belly - Erotic Vore Mind Melt

Wander Into The VORE Goddess Belly - Erotic Vore Mind Melt

Clips4sale 2 years ago

SISSY PET PUNISHED WITH BONDAGE RESTRAINTS + BALLS DRAINED [Sissy Punishment] [Pet Play] [Sissy Pet] [Bondage] [Sissy Bondage] [Sissy Bounded] [Ball Gagged] [Gagged] [Bondage Play] [CBT] [Boundage Restraint]

60% 0:30 / 17:11

SISSY PET PUNISHED WITH BONDAGE RESTRAINTS + BALLS DRAINED [Sissy Punishment] [Pet Play] [Sissy Pet] [Bondage] [Sissy Bondage] [Sissy Bounded] [Ball Gagged] [Gagged] [Bondage Play] [CBT] [Boundage Restraint]

Clips4sale 2 years ago

INSTANT WEIGHT LOSS FOR SISSIES - Sissy Weight Loss Transformation, Sissy Training

INSTANT WEIGHT LOSS FOR SISSIES - Sissy Weight Loss Transformation, Sissy Training

Clips4sale 1 year ago

Cuckold Husband gets Fucked by his Wife's Lover Sissy Crossdresser Cuck Fiona Fortune

Cuckold Husband gets Fucked by his Wife's Lover Sissy Crossdresser Cuck Fiona Fortune

Clips4sale 1 year ago

Training Pipers Ass

HD 0:10 / 18:03

Training Pipers Ass

LoyalFans 7 months ago

Room mate catches me and craves my white socks and feet

Room mate catches me and craves my white socks and feet

Clips4sale 9 months ago

Lola bondage dildo blowjob, face fuck and gag reflex training

Lola bondage dildo blowjob, face fuck and gag reflex training

Clips4sale 7 months ago

BBW Goddess Destroys Jade Storm's Ass in Fuckbox- Finger Stretching, Multi-Angle Big Cock Pounding, Shaking Moans

BBW Goddess Destroys Jade Storm's Ass in Fuckbox- Finger Stretching, Multi-Angle Big Cock Pounding, Shaking Moans

Clips4sale 8 months ago

Sissy Humiliation, Pathetic Crossdresser begs for a Strapon

Sissy Humiliation, Pathetic Crossdresser begs for a Strapon

Clips4sale 10 months ago

Sissys heel practice

Sissys heel practice

Clips4sale 10 months ago

YOUR MEDICAL RESULTS PROVE YOU ARE A GIRL WITH A TINY CLITTY - FEMINIZATION

YOUR MEDICAL RESULTS PROVE YOU ARE A GIRL WITH A TINY CLITTY - FEMINIZATION

Clips4sale 9 months ago

Gggghhhhhh

Clips4sale 1 year ago

Pegged Anal Whore Jasmine *4K*

Pegged Anal Whore Jasmine *4K*

LoyalFans 7 months ago

Your Weird Tranny Obsession

HD 0:30 / 10:55

Your Weird Tranny Obsession

Clips4sale 10 months ago

Mistress Baton’s Sissy Finishing School guest starring Mistress Vixen: Sissy Caning & BJ Training

HD 0:10 / 24:01

Mistress Baton’s Sissy Finishing School guest starring Mistress Vixen: Sissy Caning & BJ Training

LoyalFans 9 months ago

Our Greedy Sissy Hole: Part III

Our Greedy Sissy Hole: Part III

Clips4sale 9 months ago

RUBBERSLUT HIGH HEELS TRAINING - Hard Bondage & Humiliation for my LatexToy FULL SESSION HD

Premium HD 31:26

RUBBERSLUT HIGH HEELS TRAINING - Hard Bondage & Humiliation for my LatexToy FULL SESSION HD

Clips4sale 9 months ago

Latex Doll Milking Training Chapter 2 1080p

Premium HD 13:52

Latex Doll Milking Training Chapter 2 1080p

Clips4sale 8 months ago

Year of Futanari - COCK WORSHIP , MAKE ME BI , FUTA

Year of Futanari - COCK WORSHIP , MAKE ME BI , FUTA

Clips4sale 8 months ago

Sissy Maid Lola Deepthroats Trans Mistress Jade Storm

Sissy Maid Lola Deepthroats Trans Mistress Jade Storm

Clips4sale 8 months ago

No More Dominance

No More Dominance

Clips4sale 8 months ago

You Want Sissy Sex

You Want Sissy Sex

Clips4sale 8 months ago

I Like My Pretty Girls Slutty

I Like My Pretty Girls Slutty

Clips4sale 9 months ago

MistressAe Sessions with Princess Latex Rubber Doll: Impact & Spit Roast Training

66% HD 0:10 / 31:14

MistressAe Sessions with Princess Latex Rubber Doll: Impact & Spit Roast Training

LoyalFans 9 months ago

Bisexual Instructions 1 AUDIO ONLY

Bisexual Instructions 1 AUDIO ONLY

Clips4sale 8 months ago

Ria Bentley Fleshlight Throat Princess

Ria Bentley Fleshlight Throat Princess

Clips4sale 8 months ago

Don't Pick Up Hitchhikers Part 3 written by feminization author Kylie Gable Narrated by Shayla Aspsia

HD 0:30 / 41:28

Don't Pick Up Hitchhikers Part 3 written by feminization author Kylie Gable Narrated by Shayla Aspsia

Clips4sale 8 months ago

Guided Crossdressing Feminization : Pretty In Pink | Supportive Dress Up Instructions, Makeup, Panties & Lingerie Transformation

Guided Crossdressing Feminization : Pretty In Pink | Supportive Dress Up Instructions, Makeup, Panties & Lingerie Transformation

Clips4sale 8 months ago

Her first fuck with a big cock Sissy *HD*

Her first fuck with a big cock Sissy *HD*

Clips4sale 8 months ago

Obey the Bulge Goddess Dick Futanari with Femdom Goddess Vivien

Obey the Bulge Goddess Dick Futanari with Femdom Goddess Vivien

Clips4sale 8 months ago

futadom does sissy’s makeup then ruins it with facefucking and facial - HD

62% HD 0:30 / 8:14

futadom does sissy’s makeup then ruins it with facefucking and facial - HD

Clips4sale 8 months ago

RESOLVE GENDER MISMATCH PROGRAMMING - Transgender Training [Sissy] [Femme] [Crossdressing]

RESOLVE GENDER MISMATCH PROGRAMMING - Transgender Training [Sissy] [Femme] [Crossdressing]

Clips4sale 2 years ago

Eddy and Dani WT

Eddy and Dani WT

Clips4sale 2 years ago

me dressed as a unconvincing girl

me dressed as a unconvincing girl

Clips4sale 2 years ago

SISSY CUCKOLD COCK SUCKING TRAINING - Cuckold Training, Erotic Mind Fuck

SISSY CUCKOLD COCK SUCKING TRAINING - Cuckold Training, Erotic Mind Fuck

Clips4sale 2 years ago

COCK DEPENDENT SISSY SLUT MIND FUCK - BIG BLACK COCK, BBC, Sissy Slut Training

COCK DEPENDENT SISSY SLUT MIND FUCK - BIG BLACK COCK, BBC, Sissy Slut Training

Clips4sale 1 year ago

Panty bitch part 13 RELAPSE with MistressVictoria (EROTIC AUDIO MP3) (SISSY TRAINING) (SHOPPING) (PANTY FETISH)

Panty bitch part 13 RELAPSE with MistressVictoria (EROTIC AUDIO MP3) (SISSY TRAINING) (SHOPPING) (PANTY FETISH)

Clips4sale 1 year ago

HIGH HEELS VIBRATOR BONDAGE TRAINING RETURNS - SHAKING & TREMBLING RUBBERSLAVE MILKED WITH NO SAFEWORD 720

Premium HD 41:51

HIGH HEELS VIBRATOR BONDAGE TRAINING RETURNS - SHAKING & TREMBLING RUBBERSLAVE MILKED WITH NO SAFEWORD 720

Clips4sale 8 months ago

Sissy Slut Training with Helena Price part 2

HD 0:10 / 29:07

Sissy Slut Training with Helena Price part 2

LoyalFans 8 months ago

Your Sissy Resolution: Suck More Cock

Your Sissy Resolution: Suck More Cock

Clips4sale 8 months ago

Year of shemale - FUTA, FUTANARI, MAKE ME BI , COCK WORSHIP

Year of shemale - FUTA, FUTANARI, MAKE ME BI , COCK WORSHIP

Clips4sale 8 months ago

Glam Slut Milking Training 2 (1080p)

Premium HD 20:20

Glam Slut Milking Training 2 (1080p)

Clips4sale 8 months ago

SISSY TRAINING: BUY A WIG Goddess Alexa Bimbofication Captivate

SISSY TRAINING: BUY A WIG Goddess Alexa Bimbofication Captivate

Clips4sale 8 months ago

Good Girl ASMR Sissy Programming - Audio File - The Goddess Clue, Good Girl Programmed By My Soft Whispering, Princess Dress Up Encouragement, Gentle MommyDomme Mistress, Sissy Mind Play

Good Girl ASMR Sissy Programming - Audio File - The Goddess Clue, Good Girl Programmed By My Soft Whispering, Princess Dress Up Encouragement, Gentle MommyDomme Mistress, Sissy Mind Play

Clips4sale 8 months ago

The Cuckold Sissy Holiday Package

HD 0:30 / 11:03

The Cuckold Sissy Holiday Package

Clips4sale 10 months ago

Romantic Dominant Partner Impregnates You - Jaq Quicksilver fills you with cum and makes you pregnant - soft dom, mpreg, impregnation fantasy, roleplay, muscles, eye contact - 4k mp4

Premium 4K 8:00

Romantic Dominant Partner Impregnates You - Jaq Quicksilver fills you with cum and makes you pregnant - soft dom, mpreg, impregnation fantasy, roleplay, muscles, eye contact - 4k mp4

Clips4sale 10 months ago

4K - 2 CUMSHOT PRESENTS from SANTA FEMBOY

4K 0:18 / 38:30

4K - 2 CUMSHOT PRESENTS from SANTA FEMBOY

Clips4sale 9 months ago

be my ashtray, my little sissy bitch: tied up sissy with anal plug ashtray is a useful slut for asian goddess Asuna Bloom (german language video)

be my ashtray, my little sissy bitch: tied up sissy with anal plug ashtray is a useful slut for asian goddess Asuna Bloom (german language video)

Clips4sale 10 months ago

I Want You Pretty and in Diapers

I Want You Pretty and in Diapers

Clips4sale 9 months ago

Ts Slut Training - Episode III

61% HD 0:10 / 14:21

Ts Slut Training - Episode III

LoyalFans 9 months ago

Wife gives sissy cuck ruined orgasm at bedtime

Wife gives sissy cuck ruined orgasm at bedtime

Clips4sale 7 months ago

Tgirl fucked and slapped sex in swing

Tgirl fucked and slapped sex in swing

Clips4sale 8 months ago

Trans Roommate Part 2: Trans Roommate Caught Throat Training

Trans Roommate Part 2: Trans Roommate Caught Throat Training

Clips4sale 6 months ago

(624) Sissygasm: Chubby Crossdresser in Pink Outfit Reaches Hand-Free Orgasm with Sex Toys - Zoulette (1080p)

4K 0:30 / 13:03

(624) Sissygasm: Chubby Crossdresser in Pink Outfit Reaches Hand-Free Orgasm with Sex Toys - Zoulette (1080p)

Clips4sale 11 months ago

Hot Trans Slut Ria Bentley Gets Help with Some Bedroom Repairs Pt. 1

Hot Trans Slut Ria Bentley Gets Help with Some Bedroom Repairs Pt. 1

Clips4sale 6 months ago

Elf trains her throat! ^^

Elf trains her throat! ^^

Skyprivate 3 years ago

The Sissy Mind Virus

HD 0:29 / 12:02

The Sissy Mind Virus

Clips4sale 4 months ago

12 sissy training tasks - 2025 edition

HD 0:25 / 46:49

12 sissy training tasks - 2025 edition

Clips4sale 3 months ago

Nylon Foot Worship 1044

Nylon Foot Worship 1044

Clips4sale 5 months ago

A lengthly degrading, Humiliating and embarassing video of me putting you in your place

4K 0:34 / 25:02

A lengthly degrading, Humiliating and embarassing video of me putting you in your place

Clips4sale 5 months ago

Cock OBSESSED

Clips4sale 4 months ago

FVR - 41 - Feminize Him - Last Date - Riley

FVR - 41 - Feminize Him - Last Date - Riley

Clips4sale 5 months ago

Inside Jasmine DLight : Mistress Why does SHOULDER DEEP **** & Rose Punching

65% HD 0:10 / 12:21

Inside Jasmine DLight : Mistress Why does SHOULDER DEEP **** & Rose Punching

LoyalFans 6 months ago

Spanking and Facesitting Trans slave girl training (HD1080p)

HD 0:10 / 12:02

Spanking and Facesitting Trans slave girl training (HD1080p)

LoyalFans 5 months ago

Red Pill Alpha to Sissy Whore

Premium HD 18:26

Red Pill Alpha to Sissy Whore

Clips4sale 3 months ago

Mistress fucked hard her rubber sissy

Premium HD 8:04

Mistress fucked hard her rubber sissy

Clips4sale 3 months ago

The Wild Diaper West

The Wild Diaper West

Clips4sale 5 months ago

[4K] Lime gets pegged & ass slapped on spanking horse

4K 0:24 / 11:18

[4K] Lime gets pegged & ass slapped on spanking horse

Clips4sale 5 months ago

My slutty whorish sissy for sale ITA

My slutty whorish sissy for sale ITA

Clips4sale 4 months ago

Our Perfect Match Nympho Futa + Sissy Slut: FemDomme Taboo Breeding

HD 0:10 / 41:24

Our Perfect Match Nympho Futa + Sissy Slut: FemDomme Taboo Breeding

LoyalFans 7 months ago

Bimbo Slut Training, FULL SERIES - Goddess Lilith

57% HD 0:10 / 47:40

Bimbo Slut Training, FULL SERIES - Goddess Lilith

LoyalFans 6 months ago

Sissy Lingerie Training

HD 0:10 / 13:04

Sissy Lingerie Training

LoyalFans 10 months ago

TGIRL DEEPTHROAT TRAINING

TGIRL DEEPTHROAT TRAINING

Clips4sale 1 year ago

FUCKED BY A NIGHT PARALYSIS FUTA DEMON - Futa Fantasy, Futanari Fantasy, Futanari Cumshots

FUCKED BY A NIGHT PARALYSIS FUTA DEMON - Futa Fantasy, Futanari Fantasy, Futanari Cumshots

Clips4sale 1 year ago

Training You to Take Real Cock: Domina Andrea Rosu And Holland Of Chicago Start by Sucking my Strap On Before Sucking Her Real Cock 1080

HD 0:10 / 11:51

Training You to Take Real Cock: Domina Andrea Rosu And Holland Of Chicago Start by Sucking my Strap On Before Sucking Her Real Cock 1080

LoyalFans 1 month ago

Pussy Is Superior To Cock Envy Affirmations

HD 0:36 / 11:09

Pussy Is Superior To Cock Envy Affirmations

Clips4sale 1 month ago

Glamour Girls Humiliation 269 wmv

Glamour Girls Humiliation 269 wmv

Clips4sale 1 month ago

FULL MOVIE SISSY STAR BATTLES Full Campaign Cult of the Goddess

HD 0:30 / 50:32

FULL MOVIE SISSY STAR BATTLES Full Campaign Cult of the Goddess

Clips4sale 1 month ago

FULL MOVIE SISSY STAR BATTLES Full Campaign Lunar Legion

Premium HD 49:47

FULL MOVIE SISSY STAR BATTLES Full Campaign Lunar Legion

Clips4sale 1 month ago

Our Cock Sucking Street Whore *FULL-HD*

Our Cock Sucking Street Whore *FULL-HD*

Clips4sale 3 weeks ago

Diaper Dolly in the Toybox

HD 0:46 / 15:30

Diaper Dolly in the Toybox

Clips4sale 1 month ago

My daily training with my dildo 25 cm

Premium HD 3:12

My daily training with my dildo 25 cm

Clips4sale 2 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

Mature Sissy Fucked by Rapper

Premium 4K 8:13

Mature Sissy Fucked by Rapper

Clips4sale 3 months ago

Goth Sissy Jade Madison Sucking Dick Compilation 1

Premium HD 20:04

Goth Sissy Jade Madison Sucking Dick Compilation 1

Clips4sale 3 months ago

she left me and forgot her fishnets…so I wear them to humiliate my ego (cute femboy)

Premium 4K 7:06

she left me and forgot her fishnets…so I wear them to humiliate my ego (cute femboy)

Clips4sale 3 months ago

Petite Trans Woman Deepthroating Bailey Wilde's Cock and BDSM Compilation

Petite Trans Woman Deepthroating Bailey Wilde's Cock and BDSM Compilation

Clips4sale 5 months ago

PLUGGED + LOCKED = THE SISSY WHORE [Sissy Training Reinforcement] [Sissy] [Chastity] [Chastity Device] [ButtPlug] [Plugged] [Plugged in Chastity] [Plug] [Butt] [Chastity Training] [Locked in Chastity] [Chastity Cage]

HD 0:30 / 17:10

PLUGGED + LOCKED = THE SISSY WHORE [Sissy Training Reinforcement] [Sissy] [Chastity] [Chastity Device] [ButtPlug] [Plugged] [Plugged in Chastity] [Plug] [Butt] [Chastity Training] [Locked in Chastity] [Chastity Cage]

Clips4sale 2 months ago

Goth Sissy Jade Madison Sucking Dick Compilation 3

Premium HD 20:03

Goth Sissy Jade Madison Sucking Dick Compilation 3

Clips4sale 3 months ago

Sissy maid has the best boipussy

Sissy maid has the best boipussy

Clips4sale 7 months ago

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