Anal Training Videos (15,024)

Anal Stretching and Gape with a Dilator - Extreme Anal Insertions

Anal Stretching and Gape with a Dilator - Extreme Anal Insertions

xHamster 11 months ago

DOMINATION & SUBMISSION Sissy inhale training with enema!

DOMINATION & SUBMISSION Sissy inhale training with enema!

TransTube.tv 8 months ago

RIDE FISTING DILDO

RIDE FISTING DILDO

xHamster 2 years ago

Czech sissy pegging KellyAErick DianaMILF

Czech sissy pegging KellyAErick DianaMILF

Love4Porn 2 years ago

AB071 Sissy tranining and pumping out(tickle,cable on ,Ruined Climax,S/M Jizz-shotgun-head responsibility)

AB071 Sissy tranining and pumping out(tickle,cable on ,Ruined Climax,S/M Jizz-shotgun-head responsibility)

TransTube.tv 8 months ago

"Transgender Ass-Fucking Action - Anal Training For The New Guy"

"Transgender Ass-Fucking Action - Anal Training For The New Guy"

Hoes.tube 2 months ago

Sissy gets wedgie in public park

Sissy gets wedgie in public park

Gayhub 6 months ago

Ultra-kinky Sissy College Friends getting BIG BLACK COCK

Ultra-kinky Sissy College Friends getting BIG BLACK COCK

Transvids.tv 1 month ago

Isabella's Extreme Gaping Pressure's

Isabella's Extreme Gaping Pressure's

xHamster 5 months ago

Katie Fox loves a huge dick

Katie Fox loves a huge dick

xHamster 11 months ago

Sissy Stacy Bimbo Doll Facefuck

Sissy Stacy Bimbo Doll Facefuck

xHamster 3 months ago

TGIRLS XXX: White Chinaa's Massage Skills

TGIRLS XXX: White Chinaa's Massage Skills

xHamster 3 years ago

AB121 Lustful succubus extreme training

AB121 Lustful succubus extreme training

xHamster 10 months ago

She's Going to Get Her Ass Fucked in the Kitchen

She's Going to Get Her Ass Fucked in the Kitchen

xHamster 1 month ago

Big cock cums while riding

Big cock cums while riding

xHamster 11 months ago

Genitalia haircut & edging for chastity thrall

Genitalia haircut & edging for chastity thrall

ShemaleSin 2 months ago

The Sissycdmish Situation Is Out of Control!

The Sissycdmish Situation Is Out of Control!

xHamster 1 month ago

Step mom pulverizes son ass and train cum while being torn up

Step mom pulverizes son ass and train cum while being torn up

TransTube.tv 11 months ago

Lola Crystals taking BIG BLACK COCK backshots by freakymandingo

Lola Crystals taking BIG BLACK COCK backshots by freakymandingo

TransTube.tv 8 months ago

Enjoying a couple of Mr. Hankey's toys

Enjoying a couple of Mr. Hankey's toys

xHamster 1 month ago

Brazilian tgirl slut training💋💘

Brazilian tgirl slut training💋💘

aShemaleTube 1 year ago

sissy sex-toy groaning dad

sissy sex-toy groaning dad

ShemaleSin 2 years ago

Handsome Sissy Cocksluts rail and ravage a BIG BLACK COCK nads deep

Handsome Sissy Cocksluts rail and ravage a BIG BLACK COCK nads deep

TrannyGem 2 years ago

Tied up and fucked - sissy is at shemales mercy

Tied up and fucked - sissy is at shemales mercy

xHamster 3 years ago

Shemale Hanna fills her throat with her urinate

Shemale Hanna fills her throat with her urinate

SortPorn 3 days ago

Trans Ria Bentley Toys Her Ass and Gives JOI in School Uniform

Trans Ria Bentley Toys Her Ass and Gives JOI in School Uniform

xHamster 4 months ago

Big is better

xHamster 2 months ago

Sissy slut’s deep anal training for big dicks

Sissy slut’s deep anal training for big dicks

xHamster 3 years ago

Sissygasm, Slut’s Caged Training, Massive Cumshots & Anal Milking – Jessica Bloom

Sissygasm, Slut’s Caged Training, Massive Cumshots & Anal Milking – Jessica Bloom

xHamster 3 years ago

Sissy Floozy Screw Doll Takes Anal Fisting, Pegging & Bang Machine with GIANT VIBRATOR Hardcore Femdom Porn!

Sissy Floozy Screw Doll Takes Anal Fisting, Pegging & Bang Machine with GIANT VIBRATOR Hardcore Femdom Porn!

SortPorn 1 month ago

Sissy Compilation Outside drinking and twat screw in Public

Sissy Compilation Outside drinking and twat screw in Public

ShemaleSin 3 weeks ago

TS Natalie Mars trains Dr Pierce Paris how to be used like a slut

TS Natalie Mars trains Dr Pierce Paris how to be used like a slut

KeekAss 2 months ago

Sasha Earth – teen sissy slut fucks ass with anal fox tail toy

Sasha Earth – teen sissy slut fucks ass with anal fox tail toy

xHamster 3 years ago

Emily Adaire gets a helping hand to open up her pinkish crevice - Trailer

Emily Adaire gets a helping hand to open up her pinkish crevice - Trailer

TransTube.tv 1 year ago

Prompt assfuck teaching

Prompt assfuck teaching

Gayhub 2 weeks ago

A Rewarding Morning Awakening: Blowjob, Fist, Pegging, Chastity Release and Handjob : Mistress Julia

A Rewarding Morning Awakening: Blowjob, Fist, Pegging, Chastity Release and Handjob : Mistress Julia

xHamster 11 months ago

Husband gets sissified and his ass pegged

Husband gets sissified and his ass pegged

xHamster 1 year ago

I caught you crossdressed at the mall now you will enjoyment my male friends JOI CEI ANAL PLAY

I caught you crossdressed at the mall now you will enjoyment my male friends JOI CEI ANAL PLAY

Dafreeporn 2 years ago

Box-Training Face Busting + Hard-Bare-Assfuck At The End

Box-Training Face Busting + Hard-Bare-Assfuck At The End

BeMyHole 4 years ago

Tgirl Slut Training Teaser and BTS Chat

Tgirl Slut Training Teaser and BTS Chat

xHamster 3 weeks ago

Crossdressing sissy nikki rails again

Crossdressing sissy nikki rails again

TrannyGem 3 years ago

Sissy teaching: how to jizz in purity? Rail ever larger fuck sticks to sissygasm

Sissy teaching: how to jizz in purity? Rail ever larger fuck sticks to sissygasm

TrannyGem 3 years ago

Precum Pop-Shot Compilation

Precum Pop-Shot Compilation

TrannyGem 2 years ago

I want a big black

I want a big black

xHamster 1 year 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 10 months ago

Sissy Kate learns how to use the anal fucking machine with Lisa

Sissy Kate learns how to use the anal fucking machine with Lisa

xHamster 1 year ago

Crossdresser upskirt in the forest

Crossdresser upskirt in the forest

Gayhub 4 months ago

Locked Bitch Boy Cums Like Girl

Locked Bitch Boy Cums Like Girl

xHamster 3 years ago

Damsel yelling after vibrating her urethra with a toy❗bougie Getting Off

Damsel yelling after vibrating her urethra with a toy❗bougie Getting Off

TrannyGem 8 months ago

She Trains Her Sissy Friend to Receive Cocks

She Trains Her Sissy Friend to Receive Cocks

FapHouse 2 months ago

Transsexual play - bukkake chaos! Shemale anal👌 group sex

Transsexual play - bukkake chaos! Shemale anal👌 group sex

AsianRZ 9 months ago

A Boy in a Cage Trains His Boy Pussy for a Halloween Party to Get All the Dicks

A Boy in a Cage Trains His Boy Pussy for a Halloween Party to Get All the Dicks

xHamster 10 months ago

Sissy Slut getting fucked by machine

Sissy Slut getting fucked by machine

xHamster 1 month ago

BONDAGE & DISCIPLINE Sissy blow training with enema!

BONDAGE & DISCIPLINE Sissy blow training with enema!

Transvids.tv 10 months ago

Mistress Sissification | Pegging

Mistress Sissification | Pegging

FapCat 3 years ago

Crossdresser sissy fuckmachine fun

Crossdresser sissy fuckmachine fun

xHamster 2 years ago

Japanese crossdresser plays with big dildo and gives cumshot at room.

Japanese crossdresser plays with big dildo and gives cumshot at room.

xHamster 2 years ago

Buttfuck Update two: Goddess Edition!

Buttfuck Update two: Goddess Edition!

TrannyGem 9 months ago

GYM loving femboi training anal cardio

GYM loving femboi training anal cardio

Some.Porn 2 months ago

skinny ladyboy anal casting, slave training and cream enema

skinny ladyboy anal casting, slave training and cream enema

AnalVids 4 months ago

Unfathomable anal fisting my hunk toy with mother I'd like to fuck Lisa and tranny Charlotte

Unfathomable anal fisting my hunk toy with mother I'd like to fuck Lisa and tranny Charlotte

MatureTubeHere 1 year ago

Sissy Whore Fuck Doll Takes Anal Fisting, Pegging & Screw Machine with GIANT SEX-TOY Hardcore Femdom Porn!

Sissy Whore Fuck Doll Takes Anal Fisting, Pegging & Screw Machine with GIANT SEX-TOY Hardcore Femdom Porn!

Dafreeporn 4 weeks ago

Female pokes t-nymph with a bottle on a public beach

Female pokes t-nymph with a bottle on a public beach

TransTube.tv 8 months ago

Bent over sissy gets pegged whilst his balls hang like a worthless fucking bitch

Bent over sissy gets pegged whilst his balls hang like a worthless fucking bitch

xHamster 1 month ago

Sissy Mature Crossdresser in Wedding Dress SUCKS and Takes ANAL Bridal Night Training

Sissy Mature Crossdresser in Wedding Dress SUCKS and Takes ANAL Bridal Night Training

xHamster 10 months ago

Shemale Training Her Sissy Friend.. Who May Become One Of Them

Shemale Training Her Sissy Friend.. Who May Become One Of Them

getTranny 2 years ago

Sissy cums in chastity and licks it all up

Sissy cums in chastity and licks it all up

xHamster 4 months ago

Trans Lily's ass can fit her whole fist!

Trans Lily's ass can fit her whole fist!

AnySex 1 year ago

Salope Anal & Salope Faciale. Travestie Francaise Offerte, Se Fait Prendre Le Cul Dans Toutes Les Positions.

Salope Anal & Salope Faciale. Travestie Francaise Offerte, Se Fait Prendre Le Cul Dans Toutes Les Positions.

xHamster 1 month ago

korean femboy kimono smashed

korean femboy kimono smashed

Gay4Porn 8 months ago

Hot Naked Tgirl Enjoys A 11-inch BBC Dildo

Hot Naked Tgirl Enjoys A 11-inch BBC Dildo

xHamster 2 years ago

Training for Daddy

Training for Daddy

Kams.com 1 week ago

Sexy gets machine fucked till orgasmn

Sexy gets machine fucked till orgasmn

xHamster 6 months ago

Sissy Maid Rides Her Sex Doll and Gets Chained Onto It

Sissy Maid Rides Her Sex Doll and Gets Chained Onto It

xHamster 7 months ago

Tranny Training and Stretching My Ass

Tranny Training and Stretching My Ass

xHamster 4 days ago

Anal Training Night

Anal Training Night

xHamster 2 months ago

ANAL BIG DILDO RIDE

ANAL BIG DILDO RIDE

xHamster 3 years ago

Sissy Anal Needs

73% HD 1:01 / 11:39

Sissy Anal Needs

FapHouse 7 months ago

Sissy Dolly Dungeon Play Time Pegged by Giant Bad Dragon Ding-dong and Abased by Mastix Mercer

Sissy Dolly Dungeon Play Time Pegged by Giant Bad Dragon Ding-dong and Abased by Mastix Mercer

ShemaleSin 3 weeks ago

The Sissycdmish Situation Is Out of Control!

The Sissycdmish Situation Is Out of Control!

xHamster 1 month ago

Sissy Compilation Outside drinking and pussy fuck in Public

Sissy Compilation Outside drinking and pussy fuck in Public

xHamster 4 weeks ago

Arm Wrestling Shaft For A Piece Of Booty - Whitney Wright, Roman Todd, Jade Venus

Arm Wrestling Shaft For A Piece Of Booty - Whitney Wright, Roman Todd, Jade Venus

TransHero 1 year ago

Carrie Emberlyn Bbc Training

Carrie Emberlyn Bbc Training

getTranny 2 years ago

Training My Hungry Gap - Trans Anal Training With Vibrator

Training My Hungry Gap - Trans Anal Training With Vibrator

ShemaleSin 4 weeks ago

Small, Cute Sissy Slut

Small, Cute Sissy Slut

xHamster 1 week ago

Trans Sissy Femboy has fun Fuking with HUGE DILDO on Live Cam Stream - Orgasms Galore

Trans Sissy Femboy has fun Fuking with HUGE DILDO on Live Cam Stream - Orgasms Galore

XVideos 6 months ago

destruindo o cu e as bolas do femboy usando gaiola

destruindo o cu e as bolas do femboy usando gaiola

PornBox 9 months ago

Mischievous Sissy College Friends getting BIG BLACK COCK

Mischievous Sissy College Friends getting BIG BLACK COCK

TrannyGem 2 years ago

I Caught Stepdaddy Jerking Off in His Room – Oops!

I Caught Stepdaddy Jerking Off in His Room – Oops!

XXXShake 1 year ago

Lesbo Femdom Group Sex with Trans Women — Butt🍑 Play — Fisting and Pegging

Lesbo Femdom Group Sex with Trans Women — Butt🍑 Play — Fisting and Pegging

AsianBabez 1 year ago

Kitty training her ass💗

Kitty training her ass💗

aShemaleTube 11 months ago

POV Blowjob, Anal Dildo in Boots, Dirty Talk and Huge Facial

POV Blowjob, Anal Dildo in Boots, Dirty Talk and Huge Facial

xHamster 9 months ago

Fitness Guru Labelladx Faces Off With Old School Hip Hop Icon 'OG JIM BOONES'

Fitness Guru Labelladx Faces Off With Old School Hip Hop Icon 'OG JIM BOONES'

Hoes.tube 3 days ago

ideal booty and taut gap of a gorgeous femboy gets screwed hard by a sex machine and cums

ideal booty and taut gap of a gorgeous femboy gets screwed hard by a sex machine and cums

FreePorn8 1 week ago

Setsuna's training

Setsuna's training

xHamster 1 year ago

Trans Ria Bentley Trains StepDaughter Eden Espi For Anal Sex

Trans Ria Bentley Trains StepDaughter Eden Espi For Anal Sex

BeMyHole 9 months ago

Futanari Anal Training - The Stairs of the Goddess.[Anal dildo JOI}

Futanari Anal Training - The Stairs of the Goddess.[Anal dildo JOI}

Eporner 5 months ago

Sissy Bitch Screw Doll Takes Anal Fisting, Pegging & Bang Machine with MASSIVE SEX-TOY Hardcore Femdom Porn!

Sissy Bitch Screw Doll Takes Anal Fisting, Pegging & Bang Machine with MASSIVE SEX-TOY Hardcore Femdom Porn!

Amateur8 1 month ago

Sissy Bunny Training

HD 1:01 / 13:05

Sissy Bunny Training

FapHouse 5 months ago

Horny femboy fucks with a dildo and cum like a nerd without touching

Horny femboy fucks with a dildo and cum like a nerd without touching

xHamster 1 year ago

She-Maledom Domination - Anal Training For Submissive Boy's Ass

She-Maledom Domination - Anal Training For Submissive Boy's Ass

CrazyPorn 3 weeks ago

bitch gets sissified and his boi pussy pegged & destroyed

bitch gets sissified and his boi pussy pegged & destroyed

xHamster 1 year ago

Angelina Please gets a rude awakening when her roommates Jenna Creed and Ariel Demure later return,both of their dates being duds

Angelina Please gets a rude awakening when her roommates Jenna Creed and Ariel Demure later return,both of their dates being duds

TransVibe 1 year ago

S&M Sissy Whore in Chastity Spankings and Sissygasm Riding Sextoy

S&M Sissy Whore in Chastity Spankings and Sissygasm Riding Sextoy

ShemaleSin 6 months ago

Feminized Plow Fucktoy four Life

Feminized Plow Fucktoy four Life

TrannyGem 4 years ago

hottest pulverizing machine fuck-fest ever

hottest pulverizing machine fuck-fest ever

TrannyGem 1 year ago

Diaper Sex tool Moist Sissy Joy

Diaper Sex tool Moist Sissy Joy

Amateur8 1 month ago

Tiny Demon Romped a She-creature Angel rock-hard in the BUTT

Tiny Demon Romped a She-creature Angel rock-hard in the BUTT

TransTube.tv 1 year ago

TGIRLS HOOKUP: Nyxi Deemed Worthy Enough To Cum!

TGIRLS HOOKUP: Nyxi Deemed Worthy Enough To Cum!

Rainblow 1 year ago

Caged femboy trains ass & cums💦

Caged femboy trains ass & cums💦

aShemaleTube 11 months ago

French Cuckold Wife And Lesbian Anal Sissy

French Cuckold Wife And Lesbian Anal Sissy

xHamster 1 year ago

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

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

Faptor 2 years ago

Miss Gwen Dominates Sissy with Rough Anal Pegging

Miss Gwen Dominates Sissy with Rough Anal Pegging

xHamster 8 months ago

Cute Trans Beauty Screwed by Large Schlong Compilation

Cute Trans Beauty Screwed by Large Schlong Compilation

SortPorn 3 years ago

Upskirt caught in the forest

Upskirt caught in the forest

ShemaleSin 2 weeks ago

Sissy Natasha squirts & piddles out of chastity caged schlong from Lovense sex machine screwing!

Sissy Natasha squirts & piddles out of chastity caged schlong from Lovense sex machine screwing!

ShemaleSin 2 years ago

Pegging and Cum Watching, Mistress Deep Throat and Fucks Crossdresser Masochist with Strapon and Makes Him Masturbate

Pegging and Cum Watching, Mistress Deep Throat and Fucks Crossdresser Masochist with Strapon and Makes Him Masturbate

xHamster 6 months ago

Becky Scolds Sissy Slut Michel for Not Cleaning the Kitchen Properly

Becky Scolds Sissy Slut Michel for Not Cleaning the Kitchen Properly

xHamster 1 year ago

HerLimit: Misha Cross Extreme Deep Ass Pumping Stretching Training

HerLimit: Misha Cross Extreme Deep Ass Pumping Stretching Training

ThePornstar 4 months ago

Sissy Cock Cage Slutt Dildo Bitch extreme

Sissy Cock Cage Slutt Dildo Bitch extreme

xHamster 4 years ago

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