Training Videos - Trans (118,341)

Ms Marceau's Bondage Model Training Manual pt 2

61% HD 0:08 / 10:24

Ms Marceau's Bondage Model Training Manual pt 2

Clips4sale 2 years ago

Chief (ASMR) gets angry and trains you how to immense jizm!

Chief (ASMR) gets angry and trains you how to immense jizm!

TrannyGem 1 year ago

MISTRESS TALKS YOU INTO MAKEUP TRANSFORMATION DEPENDENCY MIND FUCK - Sissy Makeup Training

MISTRESS TALKS YOU INTO MAKEUP TRANSFORMATION DEPENDENCY MIND FUCK - Sissy Makeup Training

Clips4sale 1 year ago

The Shadow Cleric Reveals Her Secret

The Shadow Cleric Reveals Her Secret

XHamster 5 months ago

SUBMISSIVE TRANS LADYBOY ANAL CASTING, FISTING & SLAVE TRAINING

63% HD 0:24 / 45:15

SUBMISSIVE TRANS LADYBOY ANAL CASTING, FISTING & SLAVE TRAINING

Clips4sale 1 year ago

RENEES FOOTSLAVES - THE COMPLETE STORY

61% HD 0:16 / 20:19

RENEES FOOTSLAVES - THE COMPLETE STORY

Clips4sale 4 years ago

Happy Ending of the Training

HD 1:01 / 15:15

Happy Ending of the Training

FapHouse 1 year ago

Big tits MILF stepmom sucked big cock

Big tits MILF stepmom sucked big cock

Fapcat 2 years ago

Julieta Shayk Private Show

Julieta Shayk Private Show

Flirt4Free 4 years ago

Sissy Motivation 4: Sex Machine Sissy Trainer, Sissy Instruction, Sissification, Femboy

Sissy Motivation 4: Sex Machine Sissy Trainer, Sissy Instruction, Sissification, Femboy

XHamster 1 year ago

tennis club sissy

tennis club sissy

Clips4sale 2 years ago

Bennie Bunny Deep Training With Dildo

Bennie Bunny Deep Training With Dildo

DrTuber 5 months ago

TV slut anal depth training

TV slut anal depth training

XHamster 6 months ago

Reinforced Chastity Training - Breaking My Key~

Reinforced Chastity Training - Breaking My Key~

SortPorn 3 months ago

TRANSVESTITE CROSSDRESSER SLUT SPIT ROASTED BAREBACK BY 2 TOP FETISHTRANSEXUALS FRIENDS P1

HD 0:21 / 10:24

TRANSVESTITE CROSSDRESSER SLUT SPIT ROASTED BAREBACK BY 2 TOP FETISHTRANSEXUALS FRIENDS P1

Clips4sale 1 year ago

Hercules & Lance & Lian Miller Private Show

58% HD 2:00 / 8:05

Hercules & Lance & Lian Miller Private Show

Flirt4Free 3 years ago

Weak Willed Sissy In Chastity

HD 0:10 / 15:12

Weak Willed Sissy In Chastity

LoyalFans 1 year ago

Blasphemy Pump

Premium HD 14:56

Clips4sale 3 months ago

Crystal Blues Private Show

Crystal Blues Private Show

Flirt4Free 1 year ago

Cock Sucking Sissy Trans-Formed! Part 2!

57% 0:11 / 26:46

Cock Sucking Sissy Trans-Formed! Part 2!

Clips4sale 3 years ago

Femboy sissy in innocence cell plap plap plap in the shower

Femboy sissy in innocence cell plap plap plap in the shower

TrannyGem 2 years ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 2 years ago

Triple pegging for my slut

57% HD 0:16 / 9:16

Triple pegging for my slut

Clips4sale 2 years ago

Master's Training Session No. 101: Outdoor Blindfolded Vibrator Training

Master's Training Session No. 101: Outdoor Blindfolded Vibrator Training

XHamster 5 months ago

Vanessabitchx the Cock Drainer

Vanessabitchx the Cock Drainer

XHamster 1 year ago

Sandra Palmer Private Show

Sandra Palmer Private Show

Camster 3 weeks ago

Perseo & Dafne Private Show

HD 2:00 / 10:58

Perseo & Dafne Private Show

Flirt4Free 1 year ago

Training Comp

AShemaleTube 6 years ago

Shemale Hentai tdi [Eva´s secret training game]

Shemale Hentai tdi [Eva´s secret training game]

SortPorn 5 years ago

Brutus K Private Show

Brutus K Private Show

Flirt4Free 6 years ago

Headmistress Mercer Cumming on FuckMachine Latex Sissy Chastity Release

Headmistress Mercer Cumming on FuckMachine Latex Sissy Chastity Release

ShemaleSin 11 months ago

Carla F Coxx Private Show

Carla F Coxx Private Show

Camster 3 years ago

Neomie Thompson Private Show

HD 2:00 / 45:13

Neomie Thompson Private Show

Flirt4Free 9 months ago

THE TRAINING OF MY TS THRALL ANGEL PT two

THE TRAINING OF MY TS THRALL ANGEL PT two

ShemaleSin 5 years ago

Don't Pick Up Hitchhikers

62% HD 0:30 / 43:37

Don't Pick Up Hitchhikers

Clips4sale 1 year ago

Nightmare of Sissy Slut Ball Plapping for the BNWO

Nightmare of Sissy Slut Ball Plapping for the BNWO

XHamster 10 months ago

Angel Moran Private Show

Angel Moran Private Show

Camster 3 years ago

Her Slave Uncaged - Chelsea Poe and Sinn Sage Trans Lesbian Domination With BDSM and Strapon Fucking MOV

HD 0:19 / 32:41

Her Slave Uncaged - Chelsea Poe and Sinn Sage Trans Lesbian Domination With BDSM and Strapon Fucking MOV

Clips4sale 9 months ago

LAURA's CROSSDRESSING - wmv SD

LAURA's CROSSDRESSING - wmv SD

Clips4sale 3 years ago

Sissy Training Sissygasm Encouragement Jessica Bloom xh

Sissy Training Sissygasm Encouragement Jessica Bloom xh

Eporner 1 year ago

Jill Pill: Mouth Training

Jill Pill: Mouth Training

ShemaleSin 2 months ago

Angie Mendoza Private Show

Angie Mendoza Private Show

Flirt4Free 4 years ago

depth training with double sided sextoy

depth training with double sided sextoy

ShemaleSin 3 weeks ago

Senpai Trains TS Doxy

Senpai Trains TS Doxy

ShemaleSin 4 years ago

Husband Gets Cucked by Neighbor at Spring Picnic Festival

37% 0:09 / 14:05

Husband Gets Cucked by Neighbor at Spring Picnic Festival

Clips4sale 3 years ago

Femdom Mommy Mistress Milks Bound Sissy Crossdresser

Femdom Mommy Mistress Milks Bound Sissy Crossdresser

Eporner 7 years ago

Master & Christian Mckenzie & Christian Rey Private Show

HD 2:00 / 26:46

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 3 years ago

committed to pleasing him

committed to pleasing him

Clips4sale 2 years ago

Wild Sabrina Private Show

Wild Sabrina Private Show

Flirt4Free 6 years ago

Samantha & Alisha Private Show

HD 2:00 / 1:20:28

Samantha & Alisha Private Show

Flirt4Free 1 year ago

Amy Cums Hard for (D)addy

Amy Cums Hard for (D)addy

ShemaleSin 3 years ago

Julieta Shayk Private Show

HD 2:00 / 12:51

Julieta Shayk Private Show

Flirt4Free 5 years ago

after the gloryhole: futa femdom sissy chastity & diaper fetish blowjob - HD wmv

61% HD 0:30 / 5:13

after the gloryhole: futa femdom sissy chastity & diaper fetish blowjob - HD wmv

Clips4sale 2 years ago

Sissy Toy - Gummispielzeug aufgeblasen

Sissy Toy - Gummispielzeug aufgeblasen

Clips4sale 1 year ago

Diabla Rivers & Rouse Morgan Private Show

66% HD 2:00 / 5:07

Diabla Rivers & Rouse Morgan Private Show

Flirt4Free 3 years ago

Instructions for advanced or beginner sissy, very hot and beautiful (sissy, femboy)

Instructions for advanced or beginner sissy, very hot and beautiful (sissy, femboy)

MyTransfix 2 months ago

Turning My Boyfriend Into Girlfriend Femdom Sissy Boy Transformation Crossdressing

Turning My Boyfriend Into Girlfriend Femdom Sissy Boy Transformation Crossdressing

FapHouse 4 months ago

Mistress Amber beats Amy angle 1

Mistress Amber beats Amy angle 1

Clips4sale 3 years ago

Training to become a sissy cuckold

Training to become a sissy cuckold

DrTuber 2 years ago

femboy locked in chastity thong banged by bbc sex-toy

femboy locked in chastity thong banged by bbc sex-toy

ShemaleSin 2 years ago

Super TS Star Jade Venus Anal Masturbating

Super TS Star Jade Venus Anal Masturbating

Eporner 9 months ago

Purple Hair Femboy doing Ass to Throat in Stockings

Purple Hair Femboy doing Ass to Throat in Stockings

XHamster 1 year ago

Talking About Some of My Armwrestling Challenges

57% HD 2:00 / 4:02

Talking About Some of My Armwrestling Challenges

Flirt4Free 2 years ago

Boot Bitch for Lezdoms - Goddess Kyaa Goddess Nyx + Haskell Holland - 4K MP4

4K 0:45 / 12:49

Boot Bitch for Lezdoms - Goddess Kyaa Goddess Nyx + Haskell Holland - 4K MP4

Clips4sale 1 year ago

Danna Wright Private Show

Danna Wright Private Show

Flirt4Free 1 year ago

Alizzz Storm Private Show

4K 2:00 / 32:57

Alizzz Storm Private Show

Camster 11 months ago

Carla F Coxx Private Show

Carla F Coxx Private Show

Camster 3 years ago

Ricardo Acosta Private Show

HD 2:00 / 25:50

Ricardo Acosta Private Show

Flirt4Free 4 years ago

Trainer's Order No 15 Tuck Cooking Lunch

Trainer's Order No 15 Tuck Cooking Lunch

XHamster 8 months ago

Meinu Trains Me in Ninja Costume - Sissy Dream

61% HD 0:39 / 10:07

Meinu Trains Me in Ninja Costume - Sissy Dream

FapHouse 1 year ago

Lovely she-male gives the most sloppiest strong oral to a gamer with a fat man rod

Lovely she-male gives the most sloppiest strong oral to a gamer with a fat man rod

TrannyGem 1 year ago

Nylon Teased Chastity Slut (MP4)

57% 0:30 / 17:27

Nylon Teased Chastity Slut (MP4)

Clips4sale 2 years ago

Dominated By OSHA Inspector Princess Donna - TRAILER

Dominated By OSHA Inspector Princess Donna - TRAILER

AShemaleTube 3 months ago

Hot Thick Trans Booty Plug Play

Hot Thick Trans Booty Plug Play

ShemaleSin 6 months ago

Carla F Coxx Private Show

Carla F Coxx Private Show

Flirt4Free 3 years ago

Skarlet Fluff Private Show

Skarlet Fluff Private Show

Camster 2 years ago

Jan Fernandez Private Show

Jan Fernandez Private Show

Flirt4Free 2 years ago

Cloe & Charlotte Private Show

HD 2:00 / 13:22

Cloe & Charlotte Private Show

Flirt4Free 3 years ago

Sissy Training 101 W/ CumSlutAmee

HD 0:10 / 11:48

Sissy Training 101 W/ CumSlutAmee

LoyalFans 3 years ago

Indian Crossdresser Trans Girl Jasmin - Full Dressing & Gorgeous Webcam Shoot

Indian Crossdresser Trans Girl Jasmin - Full Dressing & Gorgeous Webcam Shoot

XHamster 6 months ago

Allie North being nice and wide open

Allie North being nice and wide open

TrannyGem 3 years ago

Australian crossdresser toying his sexy ass

Australian crossdresser toying his sexy ass

XHamster 3 years ago

Shemale dominates chu including massive penis

Shemale dominates chu including massive penis

KAMS 1 year ago

Porno training with Amy Amore

Porno training with Amy Amore

AShemaleTube 3 years ago

Feminized By Fresh Stepfather - A Sissy Caption Story ????????????

Feminized By Fresh Stepfather - A Sissy Caption Story ????????????

ShemaleSin 2 years ago

QOS Sissy Bi-atch Lola Crystals get a BIG BLACK COCK Internal ejaculation

QOS Sissy Bi-atch Lola Crystals get a BIG BLACK COCK Internal ejaculation

Transvids.tv 1 year ago

Fuckfest and trains of the CentoXCento with the trans Sabrina Pa

Fuckfest and trains of the CentoXCento with the trans Sabrina Pa

MatureTubeHere 4 years ago

Lorens Tyler Private Show

Lorens Tyler Private Show

Flirt4Free 2 years ago

Teen Oiled Fat Ass Shemale Anal Fucked Lying Down and Getting Farting Anal Creampies

Teen Oiled Fat Ass Shemale Anal Fucked Lying Down and Getting Farting Anal Creampies

XHamster 4 months ago

Sissy Slutty Kitty wants Daddy to fill her holes Clip 1

Sissy Slutty Kitty wants Daddy to fill her holes Clip 1

XHamster 4 months ago

LIVE-IN SISSYMAID TRAINING BETA - Sissymaid Course [Sissymaids] [HouseMaid] [Sissymaid School] [Sissies]

LIVE-IN SISSYMAID TRAINING BETA - Sissymaid Course [Sissymaids] [HouseMaid] [Sissymaid School] [Sissies]

Clips4sale 1 year ago

Ambar Wyne Private Show

Ambar Wyne Private Show

Flirt4Free 4 years ago

Advanced Sissy Training - Not for Beginners

Advanced Sissy Training - Not for Beginners

AbTranny 7 years ago

skinny ladyboy anal casting, slave training and cream enema

53% HD 1:01 / 32:05

skinny ladyboy anal casting, slave training and cream enema

PornBox 1 year ago

Hot and Sexy Big Cock Latina

65% HD 2:00 / 11:19

Hot and Sexy Big Cock Latina

Flirt4Free 8 years ago

Emma & Zayden Private Show

HD 2:00 / 15:56

Emma & Zayden Private Show

Flirt4Free 2 weeks ago

Hard anal fisting a gaping assholed cross dresser slave with loud farts hd

Hard anal fisting a gaping assholed cross dresser slave with loud farts hd

SexTubeSpot 4 years ago

JUDE LYNX — OMEGA MAN IN FEVER: GIANT COOCHIE NUTTING

JUDE LYNX — OMEGA MAN IN FEVER: GIANT COOCHIE NUTTING

TrannyGem 8 months ago

Blonde Bimbo Gets Deep Anal Training from Tall Redhead Futanari in Standing Fuck Lift

Blonde Bimbo Gets Deep Anal Training from Tall Redhead Futanari in Standing Fuck Lift

AnimeHentaiXHub 9 months ago

Crossdressing for Dessert: POV Dominant Girlfriend Dresses You up

Crossdressing for Dessert: POV Dominant Girlfriend Dresses You up

XHamster 2 years ago

Seductive Layla Private Show

Seductive Layla Private Show

Camster 9 months ago

BLACKED Sexy Blonde Ash Hollywood Cheats with Her BBC Trainer

BLACKED Sexy Blonde Ash Hollywood Cheats with Her BBC Trainer

FreePorn8 6 years ago

BLACKED Hawt Golden-Haired Ash Hollywood Cheats with Her BBC Tutor

BLACKED Hawt Golden-Haired Ash Hollywood Cheats with Her BBC Tutor

SortPorn 5 years ago

Turning You Bi - Sydney Screams & FtM Jaq Quicksilver Teach You How to Suck Cock & Make You Bi for Fxxk Buck's Large Load - Bisexual Encouragement, Make Me Bi, Handjobs - HD 720 WMV

HD 0:22 / 11:39

Turning You Bi - Sydney Screams & FtM Jaq Quicksilver Teach You How to Suck Cock & Make You Bi for Fxxk Buck's Large Load - Bisexual Encouragement, Make Me Bi, Handjobs - HD 720 WMV

Clips4sale 1 year ago

Relentless Sissy Gooner Mockery

Relentless Sissy Gooner Mockery

Clips4sale 3 years ago

Latex Nurse Pegging Her Servitude Sissy Floozy. Essex Beauty Lisa & Tranny Lucy

Latex Nurse Pegging Her Servitude Sissy Floozy. Essex Beauty Lisa & Tranny Lucy

SortPorn 4 years ago

Womanhood 101: Bras

HD 0:30 / 16:47

Womanhood 101: Bras

Clips4sale 4 years ago

Master Collins Private Show

HD 2:00 / 28:46

Master Collins Private Show

Flirt4Free 4 years ago

Qrle-003 Lesbian Sm Series Cross-dressing Beauty Lesbian Sm Slave Training Kikyo

Qrle-003 Lesbian Sm Series Cross-dressing Beauty Lesbian Sm Slave Training Kikyo

BDSMX 9 months ago

Feminization punishment from teacher

53% HD 0:20 / 12:25

Feminization punishment from teacher

Clips4sale 1 year ago

Emmily Siete Private Show

HD 2:00 / 16:48

Emmily Siete Private Show

Flirt4Free 2 years ago

Cd mandy 5 sextoy anal training

Cd mandy 5 sextoy anal training

XXXShemalePorn 5 years ago

Luke Hardy & Cristian Ford Private Show

34% HD 2:00 / 11:36

Luke Hardy & Cristian Ford Private Show

Flirt4Free 2 years ago

sissy stud's very first steps nutting from a fuckpole in the bootie opening up sissy's taut bum

sissy stud's very first steps nutting from a fuckpole in the bootie opening up sissy's taut bum

TrannyGem 3 years ago

Convincing You To Become A Controlled Sissy-Girl (HD MP4)

62% 4K 0:31 / 14:50

Convincing You To Become A Controlled Sissy-Girl (HD MP4)

Clips4sale 2 years ago

Sandy Lee Private Show

HD 2:00 / 11:14

Sandy Lee Private Show

Flirt4Free 11 years ago

Tatiana & Seline Private Show

HD 2:00 / 12:19

Tatiana & Seline Private Show

Flirt4Free 3 years ago

Sissy Pluged Vibrator Training

Sissy Pluged Vibrator Training

ShemaleSin 7 months ago

Kristel Zafiro Private Show

Kristel Zafiro Private Show

Flirt4Free 2 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

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118,341 results found

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