Training Videos - Trans (87,258)

Egirl girlfriend finds your feminization fetish

Egirl girlfriend finds your feminization fetish

TrannyGem 2 years ago

Slut Slave Training

Slut Slave Training

xHamster 1 week ago

My Nipples So Hard^^

My Nipples So Hard^^

Flirt4Free 10 months ago

Finally all in with 15 inch King Cock dildo

Finally all in with 15 inch King Cock dildo

xHamster 3 months ago

Pegging gangbang for naughty students

62% 0:21 / 12:59

Pegging gangbang for naughty students

Clips4sale 3 years ago

Helena Price Presents - Training Her Tranny Ass With My BBC!!! Part 1 of 2 MP4

61% 0:11 / 29:07

Helena Price Presents - Training Her Tranny Ass With My BBC!!! Part 1 of 2 MP4

Clips4sale 2 years ago

Emma & Master Private Show

HD 2:00 / 11:18

Emma & Master Private Show

Flirt4Free 5 days ago

Indian tamil step daddy alone person sex

Indian tamil step daddy alone person sex

xHamster 1 year ago

Training A Sissy How To Suck Cock

Training A Sissy How To Suck Cock

BoyFriendTV 5 years ago

Margaux Fox Private Show

Margaux Fox Private Show

Flirt4Free 5 years ago

Training sissy pussy BBC

Training sissy pussy BBC

xHamster 10 months ago

Caught with My Knickers Down!

Caught with My Knickers Down!

Flirt4Free 3 years ago

In Silence, Stepsisters make Cum Slut Earn Her Keep

In Silence, Stepsisters make Cum Slut Earn Her Keep

Clips4sale 1 month ago

Sissy Surrender: Cucked and Controlled in My Whispering Chambers by Findom Goaldigger

Sissy Surrender: Cucked and Controlled in My Whispering Chambers by Findom Goaldigger

xHamster 3 months ago

Charlie Cano Private Show

63% HD 2:00 / 8:26

Charlie Cano Private Show

Flirt4Free 3 years ago

Long Bike Ride with Huge Dildo up My Ass - Caught so Many Times

60% HD 1:01 / 5:17

Long Bike Ride with Huge Dildo up My Ass - Caught so Many Times

FapHouse 1 month ago

Housewife Breeding By Super-fucking-hot She-creature Shooting Her Jizm Deep Inside My Wife Twat

Housewife Breeding By Super-fucking-hot She-creature Shooting Her Jizm Deep Inside My Wife Twat

TransTube.tv 1 year ago

Mistress Trains TS Hucow

Mistress Trains TS Hucow

aShemaleTube 8 years ago

Sissy Brainfuck Compilation Full Movie

51% HD 1:01 / 1:13:21

Sissy Brainfuck Compilation Full Movie

FapHouse 5 months ago

Nelly Gale Private Show

Nelly Gale Private Show

Flirt4Free 3 weeks ago

I cum hands free bouncing on a 7inch dildo while my small cock flops with excitement

I cum hands free bouncing on a 7inch dildo while my small cock flops with excitement

xHamster 2 years ago

Big Step Sister Girlfriend Training - Natasha Nice - Family Therapy - Alex Adams

Big Step Sister Girlfriend Training - Natasha Nice - Family Therapy - Alex Adams

XVideos 2 years ago

Troy Khalil Party on Nov 6, 2025

45% 4K 2:00 / 50:13

Troy Khalil Party on Nov 6, 2025

Flirt4Free 3 months ago

Interracial Tease & Ballbusting For Trans Woman Julia Masakova MOV | MahoganyQen

4K 0:20 / 14:58

Interracial Tease & Ballbusting For Trans Woman Julia Masakova MOV | MahoganyQen

Clips4sale 1 week ago

MY COCK IS GOING TO SQUIRTER NOW!!!

MY COCK IS GOING TO SQUIRTER NOW!!!

XVideos 1 year ago

Viktor Renaldi Private Show

HD 2:00 / 54:57

Viktor Renaldi Private Show

Flirt4Free 3 years ago

Futanari Jessie from Pokemon

Futanari Jessie from Pokemon

xHamster 5 months ago

Hotel Pegging with Sissy Sophie and My Big Black Cock

63% HD 1:01 / 25:17

Hotel Pegging with Sissy Sophie and My Big Black Cock

FapHouse 2 weeks ago

Ftm Pegging

xHamster 1 month ago

Sissy BIG BLACK COCK Agonizing Rectal Instructing

Sissy BIG BLACK COCK Agonizing Rectal Instructing

TrannyGem 4 years ago

Wanking training with Anna

Wanking training with Anna

xHamster 3 years ago

Femboy in Yoga Pants Fucking her Fat Ass with Bbc Dildo and gets an Anal Creampie

Femboy in Yoga Pants Fucking her Fat Ass with Bbc Dildo and gets an Anal Creampie

xHamster 1 month ago

PEGGING CUNSHOTS COMPILATION!!! SEXY ORGASMS of SISSY DOXY

PEGGING CUNSHOTS COMPILATION!!! SEXY ORGASMS of SISSY DOXY

ShemaleSin 6 months ago

Sissy Instructing Part two

Sissy Instructing Part two

4Gay 6 months ago

Bedtime for Sissy Taylor

Bedtime for Sissy Taylor

xHamster 1 week ago

SISIFICATION, BBC ADDICTED Submissive Training Part 2 (Your ANUS Will Receive A Big, Thick And Very Veiny Cock) Sissy Training

SISIFICATION, BBC ADDICTED Submissive Training Part 2 (Your ANUS Will Receive A Big, Thick And Very Veiny Cock) Sissy Training

BeMyHole 7 months ago

Sounding and Prostate Exam - Fisting

Sounding and Prostate Exam - Fisting

xHamster 11 months ago

Ultimate Sissy Fuck Doll Trainer

57% HD 0:39 / 7:05

Ultimate Sissy Fuck Doll Trainer

FapHouse 1 month ago

Feminization - Sissification - Sissy Training - Sissy Whore For Mom

Feminization - Sissification - Sissy Training - Sissy Whore For Mom

ShemaleSin 1 year ago

Crossdresser destroy asshole with fucking machine and BAM dildo

Crossdresser destroy asshole with fucking machine and BAM dildo

xHamster 2 years ago

Sissy Mara Jade's FULL Sissygasm Chastity Compilation!

Sissy Mara Jade's FULL Sissygasm Chastity Compilation!

ShemaleSin 4 years ago

Enormous Compilation Concerning Butthole Cumming And Solo Cumshots Collection sissygasm ( trap milking )

Enormous Compilation Concerning Butthole Cumming And Solo Cumshots Collection sissygasm ( trap milking )

KAMS 1 year ago

Christian & Nicco & Elvis Private Show

HD 2:00 / 12:18

Christian & Nicco & Elvis Private Show

Flirt4Free 1 year ago

Sissy Girlfriend Gets a Sweet and Hard Ass Fuck

HD 1:01 / 16:00

Sissy Girlfriend Gets a Sweet and Hard Ass Fuck

FapHouse 2 months ago

Pegged in Pink - Sissy Pegging POV

Pegged in Pink - Sissy Pegging POV

xHamster 1 year ago

Elia Blaine Sissy Training With Dildo On The Wall

Elia Blaine Sissy Training With Dildo On The Wall

Nuvid 2 weeks ago

Sissy Slips Hatian BBC Unfathomable down Floozy Mouth

Sissy Slips Hatian BBC Unfathomable down Floozy Mouth

ShemaleSin 4 years ago

Jhordy & Maxx Private Show

52% HD 2:00 / 53:16

Jhordy & Maxx Private Show

Flirt4Free 6 months ago

Spectacular steamy T.I.L.F training toyboy

Spectacular steamy T.I.L.F training toyboy

KeekAss 4 years ago

Goddesss Glasses - Framed Feminization Transformation for Paypig Sissies Clip by Findom Goaldigger

Goddesss Glasses - Framed Feminization Transformation for Paypig Sissies Clip by Findom Goaldigger

xHamster 3 months ago

Underwear Modelling, Mostly Speedos, Posing Suit and a Thong

Underwear Modelling, Mostly Speedos, Posing Suit and a Thong

Flirt4Free 2 years ago

Luccas & Archie & Jose Private Show

63% HD 2:00 / 52:50

Luccas & Archie & Jose Private Show

Flirt4Free 3 weeks ago

Sophia Loreen Party on Feb 6, 2026 - Part 2

4K 2:00 / 27:49

Sophia Loreen Party on Feb 6, 2026 - Part 2

Flirt4Free 1 week ago

Summertime Saga Part 210 - Pizzeria by MissKitty2K

Summertime Saga Part 210 - Pizzeria by MissKitty2K

xHamster 5 months ago

Andrea & Taty Private Show

Andrea & Taty Private Show

Flirt4Free 1 month ago

a enslaved and obedient sissy for big black cock

a enslaved and obedient sissy for big black cock

TransTube.tv 1 year ago

Pegging my sissy gimp in permanent chastity

Pegging my sissy gimp in permanent chastity

ShemaleSin 3 weeks ago

We Laugh at Your Mini Cock! Fuck a Pillow Until You Come! Loser JOI German!

55% HD 1:01 / 8:39

We Laugh at Your Mini Cock! Fuck a Pillow Until You Come! Loser JOI German!

FapHouse 3 weeks ago

Wank off While I jism on Your Face Sissy Fag - Jessica Bloom Humilation Jerk Off Instructions

Wank off While I jism on Your Face Sissy Fag - Jessica Bloom Humilation Jerk Off Instructions

TrannyGem 1 year ago

GAY Destroys my ass STRETCH BUTT PLUG FUN

GAY Destroys my ass STRETCH BUTT PLUG FUN

xHamster 3 years ago

Femboy Rectal Spreading With A Yam-Sized Node Fuck Stick

Femboy Rectal Spreading With A Yam-Sized Node Fuck Stick

Gay4Porn 11 months ago

Can I truly get this supah-long plaything all the way in my booty? Emily Adaire's assfuck-bootcamp - day three

Can I truly get this supah-long plaything all the way in my booty? Emily Adaire's assfuck-bootcamp - day three

TrannyGem 10 months ago

Cum Facial and Cock Cleaning П🍆💦🤤

45% HD 2:00 / 44:57

Cum Facial and Cock Cleaning П🍆💦🤤

Flirt4Free 8 months ago

The Sissy Latex Fuckdoll Oral and Anal by Mistress

66% 1:01 / 12:26

The Sissy Latex Fuckdoll Oral and Anal by Mistress

FapHouse 8 months ago

White Sissy Virginity Instructing (Smash Machine)

White Sissy Virginity Instructing (Smash Machine)

TrannyGem 3 months ago

Crazy Night

45% HD 2:00 / 32:38

Flirt4Free 3 years ago

Hot Girls Fucking Guys with Strapons FEMDOM PEGGING PANTYHOSE ANAL

Hot Girls Fucking Guys with Strapons FEMDOM PEGGING PANTYHOSE ANAL

FreePorn8 5 years ago

Elix & Elias & Paulo Private Show

46% HD 2:00 / 11:00

Elix & Elias & Paulo Private Show

Flirt4Free 7 months ago

Start with Average Size - Goes Deep with BBC Size - Spandexfemboy

Start with Average Size - Goes Deep with BBC Size - Spandexfemboy

xHamster 6 months ago

Cuck Gets Fucked by Wife's BBC Bull Lover CD Sissy Fiona Fortune

65% HD 0:39 / 12:18

Cuck Gets Fucked by Wife's BBC Bull Lover CD Sissy Fiona Fortune

FapHouse 7 months ago

Female domination on sissy whore in chastity cage

Female domination on sissy whore in chastity cage

xHamster 2 years ago

Skinny Ladyboy Anal Casting, Slave Training and Cream Enema

Skinny Ladyboy Anal Casting, Slave Training and Cream Enema

xHamster 10 months ago

Hardcore Gay 3-Way

HD 2:00 / 11:23

Hardcore Gay 3-Way

Flirt4Free 6 years ago

Sophia Loreen Party on Feb 2, 2026 - Part 4

4K 2:00 / 20:06

Sophia Loreen Party on Feb 2, 2026 - Part 4

Flirt4Free 2 weeks ago

DRINK *HD 720*

65% HD 0:30 / 21:39

Clips4sale 2 years ago

Tamara Sanders Private Show

HD 2:00 / 27:44

Tamara Sanders Private Show

Flirt4Free 1 month ago

Tamara Sanders Private Show

HD 2:00 / 16:48

Tamara Sanders Private Show

Flirt4Free 1 month ago

Feminising my sissy boi husband and pegging his tight hole and filling his mouth with cum

Feminising my sissy boi husband and pegging his tight hole and filling his mouth with cum

xHamster 2 years ago

Post Op Trans Woman Masturbation - Compilation 2

Post Op Trans Woman Masturbation - Compilation 2

xHamster 3 weeks ago

Step Mom Sissification JOI CEI for Panty

58% HD 0:39 / 15:45

Step Mom Sissification JOI CEI for Panty

FapHouse 1 year ago

Sissy femboy whore does it herself in the bathroom

Sissy femboy whore does it herself in the bathroom

xHamster 1 week ago

Jessica Bloom trains puppygirl Jenby part 2: knot throating, leghumping and cumfeeding

Premium HD 7:28

Jessica Bloom trains puppygirl Jenby part 2: knot throating, leghumping and cumfeeding

XVideosRed 1 year ago

Play with My Pet Evolved Fights

61% 0:39 / 11:25

Play with My Pet Evolved Fights

FapHouse 2 months ago

Patric & Alexander & Lian Private Show

42% HD 2:00 / 33:17

Patric & Alexander & Lian Private Show

Flirt4Free 3 years ago

Spoiled Daddy Double Pissing Blowjobs Rimjobs Deep Anal 2 Trans Girls in Chastity

Spoiled Daddy Double Pissing Blowjobs Rimjobs Deep Anal 2 Trans Girls in Chastity

XVideos 11 months ago

Lara White Sissy Enjoing herself Crossdressing and twering Femboy asspussy Crossdresser Shemale Tranny Compilation

Lara White Sissy Enjoing herself Crossdressing and twering Femboy asspussy Crossdresser Shemale Tranny Compilation

xHamster 3 years ago

Viktor Renaldi Private Show

HD 2:00 / 27:46

Viktor Renaldi Private Show

Flirt4Free 4 years ago

SPIT ROASTING THEIR CUM DUMP

SPIT ROASTING THEIR CUM DUMP

Clips4sale 2 years ago

Trans Gwen Tennyson Extreme Massive Anal Creampies and Cumfarts After Being Ass Fucked with Inflatable Dildo

Trans Gwen Tennyson Extreme Massive Anal Creampies and Cumfarts After Being Ass Fucked with Inflatable Dildo

xHamster 2 weeks ago

Actor’s Studio: A Sissy Caption TS story

Actor’s Studio: A Sissy Caption TS story

SortPorn 3 years ago

Sissy Training - Doctor's Diaper Footjob Dream

Sissy Training - Doctor's Diaper Footjob Dream

ShemaleSin 8 months ago

Master & Christian Mckenzie & Christian Rey Private Show

67% HD 2:00 / 7:39

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 3 years ago

Chloe Ortega Private Show

Chloe Ortega Private Show

Flirt4Free 8 months ago

ride dildo

55% HD 2:00 / 6:53

Flirt4Free 4 years ago

fodendo a gostosa da luiza devil na cachoeira em taubate

fodendo a gostosa da luiza devil na cachoeira em taubate

PornBox 4 weeks ago

Anal gape complications

Anal gape complications

xHamster 2 months ago

FemBoy caught on cam playing with Fucking machine

FemBoy caught on cam playing with Fucking machine

xHamster 10 months ago

Sissy Whore Practice Deepthroat Fellatio Training Sucking Sex toy

Sissy Whore Practice Deepthroat Fellatio Training Sucking Sex toy

ShemaleSin 1 year ago

Making My Cock Explode

62% HD 1:01 / 8:10

Making My Cock Explode

FapHouse 4 months ago

Spandexfemboy - Anal Destruction Part 2 BBC Dildo

Spandexfemboy - Anal Destruction Part 2 BBC Dildo

xHamster 4 months ago

Xxl Dildo Training Mr Hankey Toys, Greedy Cluster, Topped Toys, Kink3d and Kink_wear

Xxl Dildo Training Mr Hankey Toys, Greedy Cluster, Topped Toys, Kink3d and Kink_wear

FapHouse 1 week ago

Instruction from the trainer No6 Exposure masturbation in the parking lot in front of the store

Instruction from the trainer No6 Exposure masturbation in the parking lot in front of the store

xHamster 2 months ago

Sissy In Diaper Punished With Strict Pegging

Sissy In Diaper Punished With Strict Pegging

BallsAndBoobs 4 months ago

Pegging a Cute TS Whore 1080p ft Mistress Youko - trans strapon sissy

66% HD 0:30 / 17:40

Pegging a Cute TS Whore 1080p ft Mistress Youko - trans strapon sissy

Clips4sale 1 year ago

Zayra Ross Private Show

Zayra Ross Private Show

Flirt4Free 4 days ago

Lance & Christian & Master Private Show

62% HD 2:00 / 16:11

Lance & Christian & Master Private Show

Flirt4Free 3 years ago

Femboy Gape Compilation #2 fart-gapes

63% HD 0:39 / 6:11

Femboy Gape Compilation #2 fart-gapes

FapHouse 1 month ago

Leyla Steel Private Show

63% HD 2:00 / 28:46

Leyla Steel Private Show

Flirt4Free 1 year ago

POV changing flat chastity with urethral plug to small chastity cage

POV changing flat chastity with urethral plug to small chastity cage

xHamster 1 year ago

Turning Him Into A Sissy Slut

Turning Him Into A Sissy Slut

xHamster 2 years ago

Brandy gets extremely horny and rides fuck machine for more than twelve sissygasms

Brandy gets extremely horny and rides fuck machine for more than twelve sissygasms

aShemaleTube 1 week ago

Beauty Shemale Anal Training Using Cucumber

Beauty Shemale Anal Training Using Cucumber

xHamster 4 years ago

Cute Femboy Jessica Bloom's 1st Brilliance Gap Visit - Swallows Cum In Throat!

Cute Femboy Jessica Bloom's 1st Brilliance Gap Visit - Swallows Cum In Throat!

ShemaleSin 1 week ago

Anal Slut fisting training dildo

Anal Slut fisting training dildo

xHamster 5 months ago

Now Her Life Has Purpose

Now Her Life Has Purpose

xHamster 4 months ago

ENSEXY1: Trance Training for BBC Sissy Faggot #1 Hotwife Trains u

ENSEXY1: Trance Training for BBC Sissy Faggot #1 Hotwife Trains u

ShemaleSin 5 years ago

Eat Her Cum and Yours - CEI with Ladyboy Friend ft Mari Ayanami

59% HD 0:21 / 13:01

Eat Her Cum and Yours - CEI with Ladyboy Friend ft Mari Ayanami

Clips4sale 3 months ago

Viktor Renaldi Private Show

HD 2:00 / 58:54

Viktor Renaldi Private Show

Flirt4Free 3 years ago

Extended Cut of Big Ass Sissy in Samus Cosplay Owned, Fucked Hard, Gaped and Anal Creampie

HD 0:39 / 15:38

Extended Cut of Big Ass Sissy in Samus Cosplay Owned, Fucked Hard, Gaped and Anal Creampie

FapHouse 4 months ago

Hanna Ven Private Show

56% HD 2:00 / 2:17:23

Hanna Ven Private Show

Flirt4Free 1 year ago

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