Training Videos - Trans (87,192)

hard crossdresser pegging. fuck anal with two dildo and fisting. big dildo sissy humiliation

HD 0:30 / 15:09

hard crossdresser pegging. fuck anal with two dildo and fisting. big dildo sissy humiliation

PornBox 3 years ago

Daddy Teaches You LIFE with Huge Load of Cum - Obedience Training

Daddy Teaches You LIFE with Huge Load of Cum - Obedience Training

xHamster 2 years ago

Fuck Stick getting off with figure corset crossdresser

Fuck Stick getting off with figure corset crossdresser

TrannyGem 3 years ago

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onlyfans - emma rose birthday ts orgy party with jade venus kasey kei tori easton and zariah aura

TransDoe 2 years ago

Master & Ithan Private Show

62% HD 2:00 / 20:20

Master & Ithan Private Show

Flirt4Free 9 months ago

Training my cool trans ass for real knob during the time that my caged, pathetic girldick drips precum

Training my cool trans ass for real knob during the time that my caged, pathetic girldick drips precum

ShemaleSin 1 year ago

Femboy in thong pounding gaping ass with real dildo and jerking off big cock

Femboy in thong pounding gaping ass with real dildo and jerking off big cock

xHamster 1 year ago

Torrid Getting Off from Sissy Nymph in Glorious Cut-Offs!

Torrid Getting Off from Sissy Nymph in Glorious Cut-Offs!

TrannyGem 4 years ago

Tatiana & Seline Private Show

Tatiana & Seline Private Show

Flirt4Free 3 years ago

Elvis Rey & Andres & Aron Private Show

67% HD 2:00 / 23:08

Elvis Rey & Andres & Aron Private Show

Flirt4Free 2 years ago

Beverly Campbell Private Show

Beverly Campbell Private Show

Flirt4Free 2 weeks ago

Redhead Latina Twerk Ass While Playing with Your Thong

Redhead Latina Twerk Ass While Playing with Your Thong

xHamster 1 month ago

Leyla Steel Private Show

63% 4K 2:00 / 13:29

Leyla Steel Private Show

Flirt4Free 8 months ago

Petra back in the boom room

Petra back in the boom room

xHamster 4 months ago

Sissy's butt filled and diapered sextoy training

Sissy's butt filled and diapered sextoy training

ShemaleSin 1 week ago

SISSY NAPPY gimp gets PEGGED after whipping out URINATE CLYSTER

SISSY NAPPY gimp gets PEGGED after whipping out URINATE CLYSTER

TrannyGem 2 years ago

Jude Hanan Private Show

58% 4K 2:00 / 5:47

Jude Hanan Private Show

Flirt4Free 7 months ago

Threesome Sharing Is Caring Sharing My BF with Slut Trainign Student

Threesome Sharing Is Caring Sharing My BF with Slut Trainign Student

xHamster 2 months ago

Turkish trans slut in red lingerie and heels gets her ass oiled up and fucked hard

Turkish trans slut in red lingerie and heels gets her ass oiled up and fucked hard

XGroovy 2 years ago

”Sarah Arabic is more interested in selfies than workouts, disrupting Nicole Aria's training sessions”

”Sarah Arabic is more interested in selfies than workouts, disrupting Nicole Aria's training sessions”

ThePornstar 5 months ago

Cute tamil Indian sissy femboy in fishnets rides and fucks 7 inch white dildo and creampie's ass

Cute tamil Indian sissy femboy in fishnets rides and fucks 7 inch white dildo and creampie's ass

xHamster 1 year ago

【No arm orgasm】Japanese sissy 「orgasm only Nipples」with gym uniform.【crossdresser 男の娘女装男子偽娘】

【No arm orgasm】Japanese sissy 「orgasm only Nipples」with gym uniform.【crossdresser 男の娘女装男子偽娘】

TrannyGem 2 years ago

Patric & Oliver Private Show

48% HD 2:00 / 7:39

Patric & Oliver Private Show

Flirt4Free 3 years 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

Best Post Orgasm Torture of All Time! - Luxie Pink

Best Post Orgasm Torture of All Time! - Luxie Pink

xHamster 4 years ago

Lady Alice compilation 10 Lady Alice's Secret (mesmerize version) View originals by subscription 4K UHD 60 FPS HDR

Lady Alice compilation 10 Lady Alice's Secret (mesmerize version) View originals by subscription 4K UHD 60 FPS HDR

xHamster 1 year ago

Please Let Me Cum on You🤤

Please Let Me Cum on You🤤

Flirt4Free 6 months ago

Solo Anal pleasure and gaping in Hotel

Solo Anal pleasure and gaping in Hotel

xHamster 1 year ago

The maid whore

xHamster 1 year ago

Sudden Ejaculation In Her Fufu Pinch

Sudden Ejaculation In Her Fufu Pinch

TrannyGem 1 year ago

Anal Training Night

Anal Training Night

xHamster 7 months ago

TURNING YOU INTO A BIMBO WHORE

55% HD 0:10 / 16:29

TURNING YOU INTO A BIMBO WHORE

LoyalFans 2 years ago

A Dominant Granny Trains These Little Whores

A Dominant Granny Trains These Little Whores

xHamster 4 months ago

The English Building - mistresse Sophia - Secret Sissy Bf Pt2 - Conclude vid sequence

The English Building - mistresse Sophia - Secret Sissy Bf Pt2 - Conclude vid sequence

TransTube.tv 6 months ago

Crossdresser big anal pussy with tunnel plug

Crossdresser big anal pussy with tunnel plug

xHamster 1 year ago

Alexxa A Private Show

Alexxa A Private Show

Flirt4Free 3 weeks ago

Dripping caged sissy trying to cum

Dripping caged sissy trying to cum

xHamster 3 days ago

Cute machine fuck for crossdressers with big fake tits and latex mask

Cute machine fuck for crossdressers with big fake tits and latex mask

xHamster 1 year ago

Hot shemale in mask gives BBC best blowjob ever

Hot shemale in mask gives BBC best blowjob ever

MyLust 8 months ago

Michel Andrade & Steven Andersson Private Show

65% HD 2:00 / 23:46

Michel Andrade & Steven Andersson Private Show

Flirt4Free 2 years ago

Sissy bitch crossdresser get screwed

Sissy bitch crossdresser get screwed

2BGay 2 years ago

Liam Jacobson Private Show

61% HD 2:00 / 8:50

Liam Jacobson Private Show

Flirt4Free 3 months ago

”Best workout ever”

”Best workout ever”

429Men 12 hours ago

Sissy pluged riding BBC Dildo at desk

Sissy pluged riding BBC Dildo at desk

xHamster 4 months ago

Khalifa Gold & Lissa Hamilton Private Show

HD 2:00 / 29:10

Khalifa Gold & Lissa Hamilton Private Show

Flirt4Free 6 months ago

Hot Four Way Fuck Fest

HD 2:00 / 19:39

Hot Four Way Fuck Fest

Flirt4Free 8 years ago

Trixxy Trains u How To taskmaster tgirl whore

Trixxy Trains u How To taskmaster tgirl whore

TransTube.tv 5 months 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

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

TrannyGem 1 year ago

TS treated like Dog by Dominant Owner - Sasha de Sade & Mistress Murmur

TS treated like Dog by Dominant Owner - Sasha de Sade & Mistress Murmur

aShemaleTube 6 years ago

Gimp Jizm Latrine in Public Rest Room.

Gimp Jizm Latrine in Public Rest Room.

TrannyGem 2 years ago

Golden Shower wets my SISSY gurlfriend before FISTING cumshot

Golden Shower wets my SISSY gurlfriend before FISTING cumshot

xHamster 9 months ago

Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 3

Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 3

xHamster 2 months ago

Piss drinking small penis bisexual sissy cuckold

Piss drinking small penis bisexual sissy cuckold

xHamster 1 year ago

The sissy competition

The sissy competition

TransTube.tv 1 year ago

Jennifer Jen Private Show

Jennifer Jen Private Show

Flirt4Free 1 week ago

RoxieXXX Unleashed: Big Ass, Big Tits, & Black Cock Domination!

RoxieXXX Unleashed: Big Ass, Big Tits, & Black Cock Domination!

XXXShemalePorn 3 years ago

Femboy training part 1: The Back Arch

Femboy training part 1: The Back Arch

Gayhub 1 year ago

Milky Bois merely! Sissy Trainer! WARNING Y

Milky Bois merely! Sissy Trainer! WARNING Y

TrannyGem 5 years ago

A Dominant Granny Trains These Little Whores

A Dominant Granny Trains These Little Whores

xHamster 3 months 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 Gay Awakening Podcast Episode #58 - Sissy Asshole Completely Owned

41% HD 0:20 / 29:43

The Gay Awakening Podcast Episode #58 - Sissy Asshole Completely Owned

Clips4sale 1 year ago

Sissy oral-sex-job training with make up filter

Sissy oral-sex-job training with make up filter

ShemaleSin 1 year ago

head and eyebrows shave for obedient slave

head and eyebrows shave for obedient slave

xHamster 2 years ago

Feeding My Sissy With Custard, Bananas And A Warm Piss Finish

Feeding My Sissy With Custard, Bananas And A Warm Piss Finish

xHamster 3 months ago

Helpless Sissy T-girl: Tied up, Toyed with Monster Dildo & Fucked

55% HD 1:01 / 14:28

Helpless Sissy T-girl: Tied up, Toyed with Monster Dildo & Fucked

FapHouse 3 weeks ago

Crhistian Fucked by a Friend

Crhistian Fucked by a Friend

Flirt4Free 7 years ago

Yam-sized White CD Sissy get boinked out and spunked on by BIG BLACK COCK

Yam-sized White CD Sissy get boinked out and spunked on by BIG BLACK COCK

4Gay 4 months ago

Latex gimp pegged

Latex gimp pegged

ShemaleSin 1 month ago

Liam & Jacob Private Show

63% HD 2:00 / 5:51

Liam & Jacob Private Show

Flirt4Free 1 year ago

Sissy in Lingerie Bounces on My Cock and Cums on My Tits

Sissy in Lingerie Bounces on My Cock and Cums on My Tits

xHamster 5 months ago

Rubber slave anal training

Rubber slave anal training

xHamster 3 weeks ago

Exposed Sissy Bitch Cums Garter Belt Silk Satin

56% 1:01 / 7:11

Exposed Sissy Bitch Cums Garter Belt Silk Satin

FapHouse 1 year ago

Cute Femboy and Trans Gal Bang a Real Doll

Cute Femboy and Trans Gal Bang a Real Doll

BigTitsLust 1 month ago

Bdsm Show

51% HD 2:00 / 5:13

Flirt4Free 8 months ago

Mistress Rides and Sucks Sissys Strap-on - Cock in Chastity Cage, Useless and Denied

Mistress Rides and Sucks Sissys Strap-on - Cock in Chastity Cage, Useless and Denied

xHamster 5 months ago

becomingfemme - doja brat sissy maid to order

becomingfemme - doja brat sissy maid to order

TransDoe 2 years ago

Nastya Blue Private Show

Nastya Blue Private Show

Flirt4Free 2 years ago

Sissy Wench Jessica Bloom Plowd Hard By Biggest Ebony Weenie On Bang Machine Multiple Anal Sissygasms

Sissy Wench Jessica Bloom Plowd Hard By Biggest Ebony Weenie On Bang Machine Multiple Anal Sissygasms

ShemaleSin 3 weeks ago

GIFT FOR A FAGGOT SLAVE - Hardcore Obedience Training

GIFT FOR A FAGGOT SLAVE - Hardcore Obedience Training

xHamster 2 years ago

Sissy Vanessa comes home after a night at the disco and trains anally with her dildos

Sissy Vanessa comes home after a night at the disco and trains anally with her dildos

ShemaleSin 6 months ago

Good Girl Fucked, Bad Girl Cucked

68% HD 1:00 / 29:25

Good Girl Fucked, Bad Girl Cucked

Clips4sale 3 years ago

SADISM & MASOCHISM Sissy fellate instructing with clyster!

SADISM & MASOCHISM Sissy fellate instructing with clyster!

TrannyGem 5 months ago

Two Slices Of Love - ep 13 - Train Your Bitchy by MissKitty2K

Two Slices Of Love - ep 13 - Train Your Bitchy by MissKitty2K

xHamster 1 year ago

Sophia Loreen Slaps Butt with Enthusiasm

Sophia Loreen Slaps Butt with Enthusiasm

Flirt4Free 4 years ago

Good morning, yoga class with handsome trainer

55% HD 0:39 / 22:32

Good morning, yoga class with handsome trainer

FapHouse 3 years ago

Hot Hung Latin Threeway

55% HD 2:00 / 7:17

Hot Hung Latin Threeway

Flirt4Free 8 years ago

WVM - PART 33 - CONFESSION By MissKitty2K

WVM - PART 33 - CONFESSION By MissKitty2K

xHamster 1 year ago

My little beta boy is a femmeboy

My little beta boy is a femmeboy

xHamster 6 months ago

Liam Jacobson Private Show

HD 2:00 / 12:37

Liam Jacobson Private Show

Flirt4Free 2 months ago

Ruby Astrom Private Show

HD 2:00 / 12:27

Ruby Astrom Private Show

Flirt4Free 1 year ago

Neomie Thompson Private Show

4K 2:00 / 34:21

Neomie Thompson Private Show

Flirt4Free 6 months ago

TouchedFetish - Latex Sissy Training - Rubber Crossdresser Husband is humiliated by femdom domina with strapon & paddel - Couple

TouchedFetish - Latex Sissy Training - Rubber Crossdresser Husband is humiliated by femdom domina with strapon & paddel - Couple

xHamster 2 years ago

Brutus K Private Show

Brutus K Private Show

Flirt4Free 9 years ago

Luke Hardy & Cristian Ford Private Show

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 week ago

Advanced Anal Stretching with Jasmine-Dlight: Part 4 - Miss Hannah Blake Joins The Training

Advanced Anal Stretching with Jasmine-Dlight: Part 4 - Miss Hannah Blake Joins The Training

XVideos 3 months ago

Mey Evanson Private Show

Mey Evanson Private Show

Flirt4Free 4 years ago

Mistress Baton's Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training

Mistress Baton's Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training

xHamster 1 month ago

Lorens Valiant Private Show

HD 2:00 / 24:15

Lorens Valiant Private Show

Flirt4Free 4 years ago

Prostate Stress Test! Simultaneous Dildo Sounding Fun!

Prostate Stress Test! Simultaneous Dildo Sounding Fun!

xHamster 5 months ago

Eat My FuckDoll's Hole

Eat My FuckDoll's Hole

LoyalFans 4 months ago

Shemale sissy slave ball busting

Shemale sissy slave ball busting

xHamster 1 month ago

Luke Hardy & Cristian Ford Party on Jan 16, 2026 - Part 3

57% 4K 2:00 / 1:55:10

Luke Hardy & Cristian Ford Party on Jan 16, 2026 - Part 3

Flirt4Free 1 month ago

Extra: Gaping My Femboy Fat Ass so Wide with a Cucumber!

Extra: Gaping My Femboy Fat Ass so Wide with a Cucumber!

FapHouse 2 months ago

Japanese tranny shamelessly faps in motel lobby

Japanese tranny shamelessly faps in motel lobby

TrannyGem 2 years ago

Anny Harley Private Show

HD 2:00 / 59:58

Anny Harley Private Show

Flirt4Free 3 years ago

Dustin & Angel & Bayron Private Show

70% HD 2:00 / 4:45

Dustin & Angel & Bayron Private Show

Flirt4Free 1 year ago

Brunette TS Saki Cruise broken in by Charlotte Sartre with rough fucking

Brunette TS Saki Cruise broken in by Charlotte Sartre with rough fucking

Pornicom 8 months ago

Elia Blaine Sissy Training With Dildo On The Wall

Elia Blaine Sissy Training With Dildo On The Wall

Nuvid 3 weeks ago

Violeta Watson Private Show

Violeta Watson Private Show

Flirt4Free 2 years ago

Destroying my Sissy Fat Ass with a Huge Inflatable Dildo and an Anal Butt Plug

Destroying my Sissy Fat Ass with a Huge Inflatable Dildo and an Anal Butt Plug

xHamster 3 months ago

November 2025 Video Trailers - Katy Churchill farting, pissing, balloons, simp, smoking, facesitting

November 2025 Video Trailers - Katy Churchill farting, pissing, balloons, simp, smoking, facesitting

xHamster 3 months ago

Cutie Trans Hucow Melody Teaches Us How to Milk a Cock with Your Butt

67% HD 1:01 / 26:52

Cutie Trans Hucow Melody Teaches Us How to Milk a Cock with Your Butt

FapHouse 1 year ago

Feminization and Pegging of My Chastity Slave: Teaser Live Cam Replay: Mistress Julia

Feminization and Pegging of My Chastity Slave: Teaser Live Cam Replay: Mistress Julia

xHamster 1 year ago

Lance & Christian & Master Private Show

HD 2:00 / 18:12

Lance & Christian & Master Private Show

Flirt4Free 3 years ago

Fuck Pussy

63% 4K 2:00 / 29:58

Flirt4Free 1 month ago

Bryan is Pantied and Plugged

57% HD 0:30 / 11:04

Bryan is Pantied and Plugged

OnlyPornVideo 1 month ago

Ebony TS Anal Training and Dirty Talk

50% HD 0:08 / 0:39

Ebony TS Anal Training and Dirty Talk

FapHouse 1 year ago

Sissy Roommate Girly JOI

42% 0:14 / 10:33

Sissy Roommate Girly JOI

Clips4sale 1 year ago

Viktor Renaldi Private Show

HD 2:00 / 59:29

Viktor Renaldi Private Show

Flirt4Free 4 years ago

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