Training Videos - Trans (123,883)

Honey, TransMommy needs your rump again

Honey, TransMommy needs your rump again

TransTube.tv 1 year ago

Summer Rayne - Training

Summer Rayne - Training

Some.Porn 1 year ago

Lika Kai Private Show

Lika Kai Private Show

Camster 3 days ago

Step-Mom instruct a significant lesson to her fresh step daughter-in-law (How to be a tramp)

Step-Mom instruct a significant lesson to her fresh step daughter-in-law (How to be a tramp)

TrannyGem 2 years ago

Piss Enema Release and Fisting for Sissy Slut

65% HD 0:32 / 17:11

Piss Enema Release and Fisting for Sissy Slut

Clips4sale 10 months ago

Booty Call with Thad Maxxx

Booty Call with Thad Maxxx

XHamster 5 months ago

PMV Cockslut Pop - Sissy Peach pulverize along

PMV Cockslut Pop - Sissy Peach pulverize along

TransTube.tv 2 years ago

Step-Daddy Praises & Destroys His Trans Femboy - Rough Painful Fuck, Humiliation, Boy Pussy Stretching & Explosive Clear Cum

Step-Daddy Praises & Destroys His Trans Femboy - Rough Painful Fuck, Humiliation, Boy Pussy Stretching & Explosive Clear Cum

Clips4sale 4 months ago

Bonnie Boombelle Private Show

Bonnie Boombelle Private Show

Camster 1 month ago

Size Matters Hughe toys for naughty Crossdresser

Size Matters Hughe toys for naughty Crossdresser

XHamster 1 year ago

Trannies in training

Trannies in training

ShemaleSex 3 days ago

BBW Trans Slut Anal and Oral Training

BBW Trans Slut Anal and Oral Training

Itsrealamateurs 3 months ago

The Sissygasm

XHamster 1 year ago

Blowjob after workout! Great tranny number in the gym!

Blowjob after workout! Great tranny number in the gym!

XHamster 4 years ago

Red-Hot Arab Crossdresser DEEP THROAT in Greece

Red-Hot Arab Crossdresser DEEP THROAT in Greece

TrannyGem 3 years ago

MILF1852 - Hardcore FemDom: Billionaire to Bitch

HD 0:30 / 43:38

MILF1852 - Hardcore FemDom: Billionaire to Bitch

Clips4sale 2 years ago

Big caged & uncaged prostate milking & sissygasms Jessica Bloom

HD 0:39 / 23:54

Big caged & uncaged prostate milking & sissygasms Jessica Bloom

FapHouse 4 years ago

Get Fit with Kira Liv

Get Fit with Kira Liv

Some.Porn 1 year ago

Sissy riding dildo in escort appartment

Sissy riding dildo in escort appartment

GayJaVu 11 months ago

Shaved humiliated and Sissified by 4 Ladies Full HD

57% HD 0:30 / 14:13

Shaved humiliated and Sissified by 4 Ladies Full HD

Clips4sale 1 year ago

Sissification Lecture "The MEANING of SISSY LIFE" by Mastix Veronica Taboo at Online Sissy Academy

Sissification Lecture "The MEANING of SISSY LIFE" by Mastix Veronica Taboo at Online Sissy Academy

SortPorn 3 years ago

Straight BWC Gets Drank by Sissy Floozy

Straight BWC Gets Drank by Sissy Floozy

ShemaleSin 5 years ago

Hercules & Matt & Lance Private Show

Hercules & Matt & Lance Private Show

Flirt4Free 3 years ago

Tattooed Sissy Slut in Fishnets Chugs Two Beers Straight Up Her Ass

Tattooed Sissy Slut in Fishnets Chugs Two Beers Straight Up Her Ass

AShemaleTube 1 week ago

Immense dark-hued weenie banging sissy mega-tart Lola Crystals

Immense dark-hued weenie banging sissy mega-tart Lola Crystals

TransTube.tv 1 year ago

Sissy's Chastity - Pegged & Teased Edging ASMR Experience

Sissy's Chastity - Pegged & Teased Edging ASMR Experience

ShemaleSin 1 year ago

Ts Diana Deelight sucking on and bouncing on a big black dick compilation

61% HD 0:39 / 12:21

Ts Diana Deelight sucking on and bouncing on a big black dick compilation

FapHouse 1 month ago

Sissy Cums with Inverted Chastity Cage on

Sissy Cums with Inverted Chastity Cage on

FapHouse 1 year ago

Insatiable trans nymph is predominated with restraints and fucktoys

Insatiable trans nymph is predominated with restraints and fucktoys

TrannyGem 3 years ago

Sissy Zone Cycle 3

63% 0:20 / 21:12

Sissy Zone Cycle 3

Clips4sale 1 year ago

Futanari Muscle Growth World [ Femboy Hentai Game ] Ep.3 training our petite step sister in the living room !

Premium HD 32:26

Futanari Muscle Growth World [ Femboy Hentai Game ] Ep.3 training our petite step sister in the living room !

XVideosRed 1 year ago

Luna Florez Private Show

4K 2:00 / 10:40

Luna Florez Private Show

Flirt4Free 1 month ago

Extended Cut of Bubble but Trans Girl in Dva Cosplay Blacked by BBC Creampie and Cum Farts

Extended Cut of Bubble but Trans Girl in Dva Cosplay Blacked by BBC Creampie and Cum Farts

XHamster 11 months ago

Rot Couch

XHamster 4 months ago

Pretty glasses tv anal training 2

Pretty glasses tv anal training 2

XXXShemalePorn 3 years ago

Liam & Jacob Private Show

62% HD 2:00 / 5:51

Liam & Jacob Private Show

Flirt4Free 2 years ago

Mesmerized Painslut

HD 0:29 / 40:07

Mesmerized Painslut

Clips4sale 4 years ago

Taboo CBT Confession

54% HD 0:39 / 19:48

Taboo CBT Confession

FapHouse 3 years ago

Cyberpunk Crossdresser toys her cunt and eats cum

Cyberpunk Crossdresser toys her cunt and eats cum

ShemaleSin 10 months ago

Guy Irani

XHamster 6 months ago

Uncovered CD Sissy Katie Does Live Showcase In Purity Cell

Uncovered CD Sissy Katie Does Live Showcase In Purity Cell

TrannyGem 1 year ago

Some Other self facial :three

Some Other self facial :three

ShemaleSin 4 years ago

THREESOME with Salome Salvi and Tantaly Sex Doll

60% 4K 0:30 / 30:54

THREESOME with Salome Salvi and Tantaly Sex Doll

Clips4sale 2 years ago

sissy-fuckslut hatch and butt instructing

sissy-fuckslut hatch and butt instructing

TrannyGem 11 months ago

Pegging dominas spank crossdresser sissy in group

Pegging dominas spank crossdresser sissy in group

Some.Porn 2 years ago

Your Dickgayification

Your Dickgayification

Clips4sale 8 months ago

Horny TS Skips School

63% HD 0:39 / 10:44

Horny TS Skips School

FapHouse 2 years ago

Astolfo's Sissy Training (Hentai JOI) (Sissification, breathplay, Assplay,CEI, Fap the beat)Reupload

Astolfo's Sissy Training (Hentai JOI) (Sissification, breathplay, Assplay,CEI, Fap the beat)Reupload

Fapcat 4 years ago

Ass-fuck Training Sissy Asspussy Masturbation Sissygasm Ample Fake-manmeat Ass-fuck gape Crossdresser Femboy T-model

Ass-fuck Training Sissy Asspussy Masturbation Sissygasm Ample Fake-manmeat Ass-fuck gape Crossdresser Femboy T-model

TransTube.tv 2 years ago

”Goddess Kyaa & River Enza in Gape Training 1”

”Goddess Kyaa & River Enza in Gape Training 1”

Faptor 1 year ago

”My Ass Tastes Sweet - I Get All My 3 Holes Screwed for the Very First Time”

”My Ass Tastes Sweet - I Get All My 3 Holes Screwed for the Very First Time”

TransHero 9 months ago

Sissy Nipples in Training

Sissy Nipples in Training

XHamster 10 months ago

Vicky Katherine Private Show

63% HD 2:00 / 8:41

Vicky Katherine Private Show

Flirt4Free 3 years ago

public park whore hoe looking for mass ejaculation by strangers

public park whore hoe looking for mass ejaculation by strangers

TrannyGem 1 year ago

Tiny Knob Crossdresser Pissing and Extraordinary Anal Gaping her Overweight Booty with Large Cucumber

Tiny Knob Crossdresser Pissing and Extraordinary Anal Gaping her Overweight Booty with Large Cucumber

ShemaleSin 1 month ago

You SISSY Slut Training Video :CAROLYNFOREST

You SISSY Slut Training Video :CAROLYNFOREST

TrannyGem 7 years ago

Viky & Emma Private Show

62% HD 2:00 / 8:31

Viky & Emma Private Show

Flirt4Free 7 months ago

Sissy Slut Toy Training

50% 0:20 / 11:22

Sissy Slut Toy Training

Clips4sale 4 years ago

I Train Sweet Sissy Hole with My Strap-on

HD 0:39 / 11:11

I Train Sweet Sissy Hole with My Strap-on

FapHouse 3 weeks ago

Sandy Lee Private Show

63% HD 2:00 / 4:30

Sandy Lee Private Show

Camster 10 years ago

Sissy Anal training

Sissy Anal training

AShemaleTube 1 week ago

The Sissy Hospital

65% HD 0:29 / 8:18

The Sissy Hospital

Clips4sale 2 years ago

Sissy whores public humiliation task #1

Sissy whores public humiliation task #1

ShemaleSin 4 years ago

Sasha Miro Private Show

HD 2:00 / 26:56

Sasha Miro Private Show

Camster 3 years ago

Daniel Wet T-shirt Anal Banging

Daniel Wet T-shirt Anal Banging

Flirt4Free 3 years ago

Corrine Dittmann Private Show

4K 2:00 / 30:47

Corrine Dittmann Private Show

Camster 1 year ago

”Tranny Natalie Mars trains Dr Pierce Paris how to be used like a hoe”

”Tranny Natalie Mars trains Dr Pierce Paris how to be used like a hoe”

StarWank 1 year ago

Bound Nuru massage leads to creampie

Bound Nuru massage leads to creampie

XHamster 1 year ago

Cute puppy in corset

Cute puppy in corset

XHamster 1 year ago

Ebony TS Anal Training and Dirty Talk

66% HD 0:39 / 4:25

Ebony TS Anal Training and Dirty Talk

FapHouse 1 year ago

4-way Flip Fuck Show

63% HD 2:00 / 12:16

4-way Flip Fuck Show

Flirt4Free 9 years ago

In For the Evening: Ryley and Ava Holt

65% HD 0:29 / 25:02

In For the Evening: Ryley and Ava Holt

Clips4sale 4 years ago

My Hotwife Gameplay - Part 6 - the Book of Cuckolding

My Hotwife Gameplay - Part 6 - the Book of Cuckolding

XHamster 10 months ago

Allie North fresh toys

Allie North fresh toys

ShemaleSin 1 month ago

Big Black Cock Training Day

Big Black Cock Training Day

XHamster 3 years ago

MPREG labor during workout - Lalo Cortez

66% HD 0:14 / 8:39

MPREG labor during workout - Lalo Cortez

Clips4sale 1 year ago

Aliens Making Gender Bender Sex

Aliens Making Gender Bender Sex

Fapcat 4 years ago

turned into a trained sissy

turned into a trained sissy

FapHouse 3 years ago

REBECCA VOLPETTI

REBECCA VOLPETTI

Some.Porn 1 year ago

BNWO Snowbunny Diaper Costume for the Party

4K 0:30 / 14:32

BNWO Snowbunny Diaper Costume for the Party

Clips4sale 10 months ago

Unfathomable Anal Horse Rod Sextoy Banging Machine - Jessica Bloom

Unfathomable Anal Horse Rod Sextoy Banging Machine - Jessica Bloom

ShemaleSin 2 years ago

Matt & Sergio & Hercules Private Show

HD 2:00 / 17:13

Matt & Sergio & Hercules Private Show

Flirt4Free 3 years ago

Femmes Pub Gig six: A Sissy Feminization Series

Femmes Pub Gig six: A Sissy Feminization Series

TrannyGem 5 years ago

Feet First, Duo Domme with TS Mesha Klink

66% 0:11 / 6:09

Feet First, Duo Domme with TS Mesha Klink

Clips4sale 2 years ago

Mistress And Chastity Sissy Slut Anal Training 5 Min

Mistress And Chastity Sissy Slut Anal Training 5 Min

AbTranny 4 years ago

Sissy wench cums into her own wide open throat

Sissy wench cums into her own wide open throat

ShemaleSin 1 year ago

Pantyhose Bet Loser

Pantyhose Bet Loser

Clips4sale 3 years ago

Your Personality Test Results: Sissy!

Your Personality Test Results: Sissy!

Clips4sale 3 years ago

Sissy in Cow Micro Bikini Butt-Chugs 1L of Beer in Her Carport and Pushes It Out

Sissy in Cow Micro Bikini Butt-Chugs 1L of Beer in Her Carport and Pushes It Out

XHamster 9 months ago

Lily Eden Gags on a Sex-toy Whilst Caged, Cuffed, and Clamped

Lily Eden Gags on a Sex-toy Whilst Caged, Cuffed, and Clamped

ShemaleSin 1 year ago

Monica Farell Private Show

HD 2:00 / 27:47

Monica Farell Private Show

Flirt4Free 2 years ago

Sissy Fisting Booty Hard in Chastity

Sissy Fisting Booty Hard in Chastity

ShemaleSin 3 years ago

Crossdresser anal stretching and training with huge butt plugs, corsage, mini skirt, and latex stockings

Crossdresser anal stretching and training with huge butt plugs, corsage, mini skirt, and latex stockings

SexTubeSpot 9 months ago

Sandy Lee Private Show

Sandy Lee Private Show

Camster 10 years ago

Corporate Training 2 - 3D Futanari Animation

Corporate Training 2 - 3D Futanari Animation

3DPornDude 2 years ago

Yes Daddy - A sissy femboy ass to mouth training story

Yes Daddy - A sissy femboy ass to mouth training story

XHamster 6 years ago

HOTTEST Femboy Sissygasm Compilation #1

HOTTEST Femboy Sissygasm Compilation #1

TrannyGem 1 year ago

SUBMISSIVE ASIAN LADYBOY SLAVE TRAINING &amp_ ANAL CASTING

Premium HD 35:32

SUBMISSIVE ASIAN LADYBOY SLAVE TRAINING &amp_ ANAL CASTING

XVideosRed 1 month ago

Sissy Candy fake penis post restrain bondage compilation

Sissy Candy fake penis post restrain bondage compilation

TrannyGem 3 years ago

Using the sissy's slut holes - Part One

47% HD 0:30 / 7:53

Using the sissy's slut holes - Part One

Clips4sale 1 year ago

Diapers and Unspeakable Thoughts

HD 0:28 / 16:06

Diapers and Unspeakable Thoughts

Clips4sale 10 months ago

Big Cock Tranny Yasmin Dornelles Trains Her Booty Hole Using The Machine

Big Cock Tranny Yasmin Dornelles Trains Her Booty Hole Using The Machine

GetTranny 2 years ago

Get railed screwing hard by your futa girlfriend (Sextoy JOI)

Get railed screwing hard by your futa girlfriend (Sextoy JOI)

ShemaleSin 3 months ago

Feminization slumber party punishment

HD 0:30 / 10:13

Feminization slumber party punishment

Clips4sale 2 years ago

Cute Sissy Receives Facial from Dad's Large Ramrod

Cute Sissy Receives Facial from Dad's Large Ramrod

ShemaleSin 4 years ago

Sex Tool Hero Games - U get screwed at the gym after a workout

Sex Tool Hero Games - U get screwed at the gym after a workout

ShemaleSin 3 years ago

Sissy cock sucking competition - Miss Honour May - MP4 SD

Premium HD 8:25

Sissy cock sucking competition - Miss Honour May - MP4 SD

Clips4sale 4 years ago

Bisexual Foursome Two Sissy and Two Dominant Princesses

Bisexual Foursome Two Sissy and Two Dominant Princesses

XHamster 2 years ago

Roommate transformed you in a sissy and fucked your virgin ass with a strap on (FEMINIZATION ROLEPLAY - AI GENERATED)

Roommate transformed you in a sissy and fucked your virgin ass with a strap on (FEMINIZATION ROLEPLAY - AI GENERATED)

XHamster 1 year ago

Sissy maid slut training with my bestie Tsgirl Dani Marks how to fuck and learn with me

63% 0:54 / 11:02

Sissy maid slut training with my bestie Tsgirl Dani Marks how to fuck and learn with me

Clips4sale 11 months ago

Upskirt white undies

Upskirt white undies

TrannyGem 2 years ago

Obedience Training

Obedience Training

BeMyHole 3 years ago

Kept by Jessica Blake Part 4

Kept by Jessica Blake Part 4

ShemaleSin 6 months ago

Titillating My Inner Pussy While Stretching My Asshole to New Limits!!

HD 1:01 / 13:58

Titillating My Inner Pussy While Stretching My Asshole to New Limits!!

FapHouse 2 years ago

Tatiana & Andres Private Show

Tatiana & Andres Private Show

Camster 1 year ago

TRANSSEXUAL Willow Hammerz - Sissy PMV

TRANSSEXUAL Willow Hammerz - Sissy PMV

TrannyGem 1 year ago

Big Ass Trans Dva Ass Clapping, Wedgie and Anal Gape with Inflatable Dildo after Spanking her Butt

Big Ass Trans Dva Ass Clapping, Wedgie and Anal Gape with Inflatable Dildo after Spanking her Butt

XHamster 1 month ago

Encaged sissy pulverizes BIG BLACK COCK Fake Penis

Encaged sissy pulverizes BIG BLACK COCK Fake Penis

TrannyGem 1 year ago

Riding Big Dildo Deep Anal

Riding Big Dildo Deep Anal

XHamster 7 months ago

Hattabi4ik Sissy Femboy Trap Jizz Compilation

Hattabi4ik Sissy Femboy Trap Jizz Compilation

TrannyGem 1 year ago

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