Training Videos - Trans (29,205)

Wife's Imposed Feminization: Hormones, Ball Removal, Permanent Makeup, Penis Reduction & More!

50% HD 1:01 / 5:38

Wife's Imposed Feminization: Hormones, Ball Removal, Permanent Makeup, Penis Reduction & More!

FapHouse 3 months ago

SADISM & MASOCHISM Sissy fellate instructing with clyster!

SADISM & MASOCHISM Sissy fellate instructing with clyster!

TrannyGem 7 months ago

Bossy wife begs her hubby while he wears lingerie - Femdom

Bossy wife begs her hubby while he wears lingerie - Femdom

Fapality 2 years ago

Transsexual Training Day

Transsexual Training Day

xHamster 3 years ago

Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 6

Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 6

xHamster 3 months ago

Sissy Maddy Blonde CD Anal Training

Sissy Maddy Blonde CD Anal Training

xHamster 5 months ago

Booty Call with Thad Maxxx

63% HD 1:01 / 17:33

Booty Call with Thad Maxxx

FapHouse 3 weeks ago

TGIRLS HOOKUP: Nyxi Deemed Worthy Enough To Cum!

TGIRLS HOOKUP: Nyxi Deemed Worthy Enough To Cum!

xHamster 4 years ago

Sissy Boi’s Tiny Cock Is Caged Whilst Spreading Their Ass Cheeks and Fucking Their Worthless Ass

63% HD 1:01 / 21:45

Sissy Boi’s Tiny Cock Is Caged Whilst Spreading Their Ass Cheeks and Fucking Their Worthless Ass

FapHouse 2 months ago

Training to become a two-hole mare

Training to become a two-hole mare

xHamster 1 month ago

Having a Hard Time 14: Anna's Handjob on Shemale Jane to Cum Swallow

61% HD 1:01 / 7:16

Having a Hard Time 14: Anna's Handjob on Shemale Jane to Cum Swallow

FapHouse 2 weeks ago

Big tit lingerie TS drilling sissy in stockings

Big tit lingerie TS drilling sissy in stockings

Some.Porn 1 year ago

Bnwo Sissy Bride Gooning

72% HD 1:01 / 12:06

Bnwo Sissy Bride Gooning

FapHouse 7 months ago

Trans Sissy Slut French Maid Service Training

Trans Sissy Slut French Maid Service Training

Katestube 21 hours ago

Latex Mistress Verbally Humiliates and Strapons Rubber Sissy Doll. Arya Grander

Latex Mistress Verbally Humiliates and Strapons Rubber Sissy Doll. Arya Grander

xHamster 5 months ago

Agent Trains Her Replacement To Eat Good Pussy - A Thong-Slinging, Leather-loving Lesbian Adventure

Agent Trains Her Replacement To Eat Good Pussy - A Thong-Slinging, Leather-loving Lesbian Adventure

Some.Porn 2 years ago

Sissy Chastity Maid Service Training With Ria Bentley

Sissy Chastity Maid Service Training With Ria Bentley

xHamster 5 months ago

Japanese mistress trains and punishes house slave who is excited by the Mistress's laundry by making him wear women's underwear

Japanese mistress trains and punishes house slave who is excited by the Mistress's laundry by making him wear women's underwear

xHamster 5 months ago

In Training With A Tran - Sinn Sage

In Training With A Tran - Sinn Sage

BeMyHole 2 years ago

Dee Williams' lustful doodling and kissing after panty tease

Dee Williams' lustful doodling and kissing after panty tease

UrGayPorn 6 months ago

Miss Whitney Morgan Succumb to Sissy

HD 1:01 / 10:45

Miss Whitney Morgan Succumb to Sissy

FapHouse 3 weeks ago

Sissy Training

xHamster 2 years ago

Making My Cock Explode

Making My Cock Explode

xHamster 5 months ago

Gagging Trans Beauty Melody Gets Throat Rammed in Intense Face Fuck

Gagging Trans Beauty Melody Gets Throat Rammed in Intense Face Fuck

Jizzberry 1 year ago

Warning on Chastity Pt. 2

77% HD 1:01 / 7:25

Warning on Chastity Pt. 2

FapHouse 1 year ago

Bunny-butler Reina Hanno Sucking Two Dildos

Bunny-butler Reina Hanno Sucking Two Dildos

xHamster 6 months ago

Crossdressing Sissy Husband gets pegged & humiliated

Crossdressing Sissy Husband gets pegged & humiliated

xHamster 1 year ago

Sissy Gimp Maid

Sissy Gimp Maid

FapHouse 4 days ago

Sissy Bi-atch Pegged by Domina

Sissy Bi-atch Pegged by Domina

TransTube.tv 1 year ago

Cruel Femdom Futanari’s Muscle Fuck

HD 1:01 / 20:59

Cruel Femdom Futanari’s Muscle Fuck

FapHouse 8 months ago

Vladasexytrans Wild Anal Play in Black Dress and in Black Stockings

Vladasexytrans Wild Anal Play in Black Dress and in Black Stockings

xHamster 1 year ago

Enema and monster dildo to DESTROY SHEMALE ass of Natalie Mars

Enema and monster dildo to DESTROY SHEMALE ass of Natalie Mars

Fapality 4 years ago

Feminization Training - Show This To Your Wife

Feminization Training - Show This To Your Wife

xHamster 1 year ago

Sissified by Lolth - Sissification, Chastity, Drow, D&d

61% HD 1:01 / 9:31

Sissified by Lolth - Sissification, Chastity, Drow, D&d

FapHouse 1 year ago

She Is Going to Punish This Submissive Brat and Give Her a Red Ass

69% HD 1:01 / 19:41

She Is Going to Punish This Submissive Brat and Give Her a Red Ass

FapHouse 4 months ago

Bisexual cuckold with wife in threesome with neighbor

Bisexual cuckold with wife in threesome with neighbor

xHamster 11 months ago

The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)

The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)

xHamster 6 months ago

Corporate Training 2 (Rikolo

Corporate Training 2 (Rikolo

Eporner 3 months ago

Gender Transformations: Magic Makes You a Free Use Big Tit Bimbo Whore and Me a Big Cock Futa

Gender Transformations: Magic Makes You a Free Use Big Tit Bimbo Whore and Me a Big Cock Futa

xHamster 4 days ago

Rikolo Corporate Training 3D animation

Rikolo Corporate Training 3D animation

XGroovy 5 years ago

Wreck in my cock-squeezing lil' nail-fuckhole!!

Wreck in my cock-squeezing lil' nail-fuckhole!!

GayDudesFucking 5 months ago

Huge cum in mouth in my obedient sissy slave's mouth

Huge cum in mouth in my obedient sissy slave's mouth

xHamster 4 years ago

Pegging Hardcore Part 1

63% HD 1:01 / 25:58

Pegging Hardcore Part 1

FapHouse 1 month ago

Sissy Slut Michelle Morning Wake-up in Bangkok Hotel and Web Show

Sissy Slut Michelle Morning Wake-up in Bangkok Hotel and Web Show

xHamster 3 months ago

Asian Beauty in College Uniform Squirts While Training Her Anal by Pushing a Huge Anal Plug Out

67% HD 0:39 / 7:47

Asian Beauty in College Uniform Squirts While Training Her Anal by Pushing a Huge Anal Plug Out

FapHouse 2 months ago

Femdom POV: Humiliating My Cuck Ex Ep 3

47% HD 1:01 / 12:34

Femdom POV: Humiliating My Cuck Ex Ep 3

FapHouse 1 month ago

*Trailer* Sissy Instructing Basics With Kelli Frost

*Trailer* Sissy Instructing Basics With Kelli Frost

TrannyGem 4 years ago

Hung Trans Mistresse Punishes Inactive Sissy Maid

Hung Trans Mistresse Punishes Inactive Sissy Maid

BigTitsLust 6 months ago

Jasmine_dlight First Footing - Extreme Anal Insertions Foot Entirely up My Butt, Deep Insertion Anal Training Butt Slut

62% HD 0:39 / 3:07

Jasmine_dlight First Footing - Extreme Anal Insertions Foot Entirely up My Butt, Deep Insertion Anal Training Butt Slut

FapHouse 1 year ago

Obedience Training - Piss Covered COCK CLEANING Deepthroat

Obedience Training - Piss Covered COCK CLEANING Deepthroat

xHamster 2 years ago

Crossdresser gets machine fucked with XXL Monster Dildos #4

Crossdresser gets machine fucked with XXL Monster Dildos #4

xHamster 1 year ago

Mama Studio introduces "Training my step nephew to lick a trans for the first-ever time" - Free-for-all

Mama Studio introduces "Training my step nephew to lick a trans for the first-ever time" - Free-for-all

TrannyGem 1 day ago

The master's piss makes me jizz and spray piss at the same time. Customized by admirers

The master's piss makes me jizz and spray piss at the same time. Customized by admirers

WebcamBros 3 months ago

Bimbo Sexy Trans Transformation

63% HD 1:01 / 10:10

Bimbo Sexy Trans Transformation

FapHouse 9 months ago

Slave for tranny girl! After beach jogging there are sweaty socks and feet for his mouth!

Slave for tranny girl! After beach jogging there are sweaty socks and feet for his mouth!

xHamster 2 years ago

Ryley Rails Dominates You

Ryley Rails Dominates You

xHamster 5 months ago

Meet Nikki the Cute Femboy. Tiny Dick Bubble Butt BBC Wild Ride

Meet Nikki the Cute Femboy. Tiny Dick Bubble Butt BBC Wild Ride

xHamster 1 month ago

Trans gf Daniela Chanel penetrates my taut crevice with her phat girlcock.

Trans gf Daniela Chanel penetrates my taut crevice with her phat girlcock.

TrannyGem 1 year ago

Summertime Saga Part 183 - My Penis by MissKitty2K

Summertime Saga Part 183 - My Penis by MissKitty2K

xHamster 7 months ago

Sissy Doll's ass gets extreme insertion by a Monster can & more!

Sissy Doll's ass gets extreme insertion by a Monster can & more!

TrannyMovs 7 months ago

Submissive Asian Trans Slave Training & Anal Creampie

HD 1:01 / 37:51

Submissive Asian Trans Slave Training & Anal Creampie

FapHouse 2 weeks ago

Useless tiny cocked sissy gets humiliated whilst her tight ass fucked

Useless tiny cocked sissy gets humiliated whilst her tight ass fucked

xHamster 5 months ago

Taking Your Ass fucking Viginity ft Trans Femdominance

Taking Your Ass fucking Viginity ft Trans Femdominance

TransTube.tv 1 year ago

Topped Playthings Capture 126 Opens Up me out

Topped Playthings Capture 126 Opens Up me out

TrannyGem 3 years ago

Jessy Reed TS

61% HD 1:01 / 36:35

FapHouse 8 months ago

How to Become a Good Girl Sucking Lesson Jobs Interview

66% HD 1:01 / 7:41

How to Become a Good Girl Sucking Lesson Jobs Interview

FapHouse 1 month ago

Hot shemale in mask gives BBC best blowjob ever

Hot shemale in mask gives BBC best blowjob ever

MyLust 9 months ago

Transsexual training - bukkake gokkun! Shemale anal fuck orgy 4

Transsexual training - bukkake gokkun! Shemale anal fuck orgy 4

xHamster 1 year ago

beta loser boy gets pegging assfuck by german mistress. Hardcore Anal Orgasm.sissygasm

beta loser boy gets pegging assfuck by german mistress. Hardcore Anal Orgasm.sissygasm

xHamster 1 month ago

Trans Sissy Whore tutored by Mastix Murmur compilation

Trans Sissy Whore tutored by Mastix Murmur compilation

Amateur8 3 months ago

Going Deep DEEP ft David Anderson

Going Deep DEEP ft David Anderson

xHamster 2 years ago

Pay Back Your Debt

Pay Back Your Debt

ShemaleSin 1 week ago

Sissy Stories Ep 3: Feminized by My Wife

63% HD 1:01 / 16:27

Sissy Stories Ep 3: Feminized by My Wife

FapHouse 1 year ago

Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm

57% HD 1:01 / 13:54

Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm

FapHouse 1 year ago

Mature Mistress teaches two sissies how to be good cocksuckers

Mature Mistress teaches two sissies how to be good cocksuckers

Tranny.one 8 years ago

A ultra-nasty chick strokes as soon as she gets home????chinese crossdresser getting off

A ultra-nasty chick strokes as soon as she gets home????chinese crossdresser getting off

Transvids.tv 1 year ago

Plugging my sweet hole before training . Slow motion

Plugging my sweet hole before training . Slow motion

xHamster 1 year ago

Massive Black Dildo Quinn Stone Destroys Her Hole In Sissy Training

Massive Black Dildo Quinn Stone Destroys Her Hole In Sissy Training

BeMyHole 3 years ago

Sissy Purity Marionette Taunted and Abased by Domme, Denied and Locked in the Vice

Sissy Purity Marionette Taunted and Abased by Domme, Denied and Locked in the Vice

TrannyGem 5 years ago

Mistress pegs & sissifies her pathetic small cocked hubby

Mistress pegs & sissifies her pathetic small cocked hubby

xHamster 2 months ago

Sissy Kanisa Maid Service Ep2: Sofa Cleaning for Her Mistress

Sissy Kanisa Maid Service Ep2: Sofa Cleaning for Her Mistress

FapHouse 5 months ago

My little beta boy is a femmeboy

My little beta boy is a femmeboy

xHamster 8 months ago

Long intense machine fuck for crossdresser anal cunt

Long intense machine fuck for crossdresser anal cunt

xHamster 7 months ago

Small Dick Trans Gwen Tennyson Pissing After Riding 3 Big Black Cocks and Getting Anal Gaped and Multiple Anal Creampies

HD 1:01 / 17:55

Small Dick Trans Gwen Tennyson Pissing After Riding 3 Big Black Cocks and Getting Anal Gaped and Multiple Anal Creampies

FapHouse 23 hours ago

Black Slut Slave in a Collar Face Fucked

51% HD 0:39 / 12:50

Black Slut Slave in a Collar Face Fucked

FapHouse 6 months ago

Double cumshot, in my mouth and anal orgasm with all my toys

Double cumshot, in my mouth and anal orgasm with all my toys

xHamster 3 months ago

Black Goddess Strap-On Seduction SISSY TRAINING ASMR JOI ENGLISH

Black Goddess Strap-On Seduction SISSY TRAINING ASMR JOI ENGLISH

xHamster 2 weeks ago

Sissy Jessica Bloom Teaches You How To Suck Cock And Swallow Cum

Sissy Jessica Bloom Teaches You How To Suck Cock And Swallow Cum

xHamster 8 months ago

Let's Jerk off Together JOI

Let's Jerk off Together JOI

xHamster 2 weeks ago

Cross Dressing My Step Stepbrother and He Cums Twice

HD 1:01 / 15:29

Cross Dressing My Step Stepbrother and He Cums Twice

FapHouse 1 year ago

Black and White Sri Lankan Lady Boy

Black and White Sri Lankan Lady Boy

FapHouse 3 weeks ago

Independent Training No67 Tampon Insertion, Wearing Bloomers, Tucking Chain Crossing

Independent Training No67 Tampon Insertion, Wearing Bloomers, Tucking Chain Crossing

xHamster 3 months ago

Her Place Is Wherever He Wants Her to Be

Her Place Is Wherever He Wants Her to Be

xHamster 1 month ago

Nylon whore Dagmar321 jerks off and squirts

Nylon whore Dagmar321 jerks off and squirts

xHamster 3 years ago

Mistress Whips Two Cross-dressing Masochists with Bell-attached Clips on Their Nipples, Makes Them Play Anal Dildo Tug-of-war

57% HD 1:01 / 30:56

Mistress Whips Two Cross-dressing Masochists with Bell-attached Clips on Their Nipples, Makes Them Play Anal Dildo Tug-of-war

FapHouse 4 months ago

See the New Slave They Humiliate, Torment & Hard Fist

66% HD 1:01 / 18:02

See the New Slave They Humiliate, Torment & Hard Fist

FapHouse 1 year ago

Sissy Feminization

Sissy Feminization

xHamster 2 years ago

Femdom Real Pair female domination pegging & ding-dong mastix & sissy cuck feminization FULL clip

Femdom Real Pair female domination pegging & ding-dong mastix & sissy cuck feminization FULL clip

SortPorn 1 year ago

The Sissygasm

xHamster 10 months ago

Amazone Lady Naina fists a students ass

67% HD 1:01 / 8:36

Amazone Lady Naina fists a students ass

FapHouse 5 years ago

Sexy sissy slut nun in chastity celebrates her slutty mass, begging to be blessed with lots of BBC to serve

Sexy sissy slut nun in chastity celebrates her slutty mass, begging to be blessed with lots of BBC to serve

xHamster 3 months ago

Sissykanisa Get Fucked by Reina in Swimming Suit

56% 1:01 / 13:36

Sissykanisa Get Fucked by Reina in Swimming Suit

FapHouse 1 year ago

ULTIMATE FOOT FETISH COMPILATION - Foot Worship, Footjobs, Smelly Socks, Femdom, Pornstars, Cum On Feet, Boot Worship

ULTIMATE FOOT FETISH COMPILATION - Foot Worship, Footjobs, Smelly Socks, Femdom, Pornstars, Cum On Feet, Boot Worship

ShemaleSin 5 days ago

POV/JOI: Your trans friend helps you jerk off to the alternative and original green light, red light game, by pulling dice out of her ass

POV/JOI: Your trans friend helps you jerk off to the alternative and original green light, red light game, by pulling dice out of her ass

xHamster 5 months ago

Marissa Minx And Sissy Tanya Ts Mistress Sissy Training

Marissa Minx And Sissy Tanya Ts Mistress Sissy Training

AbTranny 5 years ago

FULL VIDEO Lena Vesper Railed By Hankeys Seahorse Screw Machine

FULL VIDEO Lena Vesper Railed By Hankeys Seahorse Screw Machine

PornFreeNow 5 months ago

AB082 Bad Lady Miss three be slapping and instructing - deep mouth crmpie (Japanese and English subtitles)

AB082 Bad Lady Miss three be slapping and instructing - deep mouth crmpie (Japanese and English subtitles)

TrannyGem 2 months ago

W*A*A*A- 223 Masochistic Trans Boy and Lesbian Slut - Female Orgasmic Erotic Anal FUCK - Mao Hamasaki, Yui Hatano, Chibitori Decensored

W*A*A*A- 223 Masochistic Trans Boy and Lesbian Slut - Female Orgasmic Erotic Anal FUCK - Mao Hamasaki, Yui Hatano, Chibitori Decensored

Eporner 8 months ago

Getting Ready for Training

58% HD 1:01 / 8:10

Getting Ready for Training

FapHouse 2 years ago

”Daisy Taylor wears miniskirt without panties on the train! This makes Johnny horny as fuck!”

”Daisy Taylor wears miniskirt without panties on the train! This makes Johnny horny as fuck!”

429Men 2 months ago

My husband is getting used to his girly panties

My husband is getting used to his girly panties

xHamster 1 year ago

Shady Spa - Victoria Shiatsu Massage Therapist

55% HD 1:01 / 15:12

Shady Spa - Victoria Shiatsu Massage Therapist

FapHouse 1 year ago

Femdom Anal Fisting Training

84% HD 1:01 / 19:11

Femdom Anal Fisting Training

FapHouse 4 months ago

Femboy Cumdump Pushes out Gallons of Cum

Femboy Cumdump Pushes out Gallons of Cum

xHamster 2 years ago

Anal Training Jessica Bloom Caged & Uncaged Sissygasms

70% HD 1:01 / 27:07

Anal Training Jessica Bloom Caged & Uncaged Sissygasms

FapHouse 1 year ago

Blowjob service for my Dominatrix.

Blowjob service for my Dominatrix.

TransTube.tv 1 year 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 4 months ago

becomingfemme - bunny summers now her trans life has purpose

becomingfemme - bunny summers now her trans life has purpose

TransDoe 2 years ago

Sissy attempting to get caught

Sissy attempting to get caught

TrannyGem 1 year ago

Anal QueenTs' tight ass stretched by massive BBC while in chastity belt & cumming hard

Anal QueenTs' tight ass stretched by massive BBC while in chastity belt & cumming hard

TrannyMovs 6 months ago

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