Training Anal Videos (91,216)

Kink Studios Tour Guide Porn

Kink Studios Tour Guide Porn

XHamster 2 months ago

SADISM & MASOCHISM Sissy fellate instructing with clyster!

SADISM & MASOCHISM Sissy fellate instructing with clyster!

TrannyGem 11 months ago

Rebeccah Gibson Private Show

Rebeccah Gibson Private Show

Flirt4Free 4 days ago

Sex Education- Preparing to Get Fucked in the Ass

Sex Education- Preparing to Get Fucked in the Ass

FapHouse 5 years ago

I was Feminized and become a Creampie and Breeding Shemale Whore!

I was Feminized and become a Creampie and Breeding Shemale Whore!

XHamster 9 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 2 years ago

Long, deliberate pulls. hips thrusting into my fist.

Long, deliberate pulls. hips thrusting into my fist.

XHamster 3 months ago

Hentai Queen Trains Me Hard in Futanari Tennis Roleplay

Hentai Queen Trains Me Hard in Futanari Tennis Roleplay

BallsAndBoobs 1 month ago

Dominic Carmine Private Show

Dominic Carmine Private Show

Flirt4Free 1 week ago

Do You Want to See a Ripped and Muscular Body?

60% HD 2:00 / 12:33

Do You Want to See a Ripped and Muscular Body?

Flirt4Free 4 years ago

Sissy femboy makes chastity content and streams on chaturbate

Sissy femboy makes chastity content and streams on chaturbate

ShemaleSin 1 year ago

Mey Evanson Private Show

Mey Evanson Private Show

Flirt4Free 4 years ago

Hairy Chest and Very Hairy Cock

HD 2:00 / 30:48

Hairy Chest and Very Hairy Cock

Flirt4Free 2 years ago

Harris Morrison Private Show

69% HD 2:00 / 9:10

Harris Morrison Private Show

Flirt4Free 2 years ago

Sissy Breezy is a rough, beautiful sissy who loves to be dominated and trained to a lifetime of bondage and cum

Sissy Breezy is a rough, beautiful sissy who loves to be dominated and trained to a lifetime of bondage and cum

TrannyMovs 3 months ago

Instructions from the trainer No 11 Daily exposure walks

Instructions from the trainer No 11 Daily exposure walks

XHamster 9 months ago

Sissy Milana dominates and milks her lesbian partner's ass with her strap-on

Sissy Milana dominates and milks her lesbian partner's ass with her strap-on

TrannyMovs 3 months ago

Brutus K Private Show

HD 2:00 / 13:21

Brutus K Private Show

Flirt4Free 8 years ago

Greedy Cock Taking Slut Gets Her Sissy Ass Destroyed!

HD 0:39 / 28:18

Greedy Cock Taking Slut Gets Her Sissy Ass Destroyed!

FapHouse 6 months ago

Training Zero Femdom Sissy Slave Slut Photoshoot Humiliation

Training Zero Femdom Sissy Slave Slut Photoshoot Humiliation

XHamster 1 month ago

Alejandra Fox Private Show

Alejandra Fox Private Show

Flirt4Free 3 weeks ago

Lola Crystals presents a BIG BLACK COCK Sissy Whore to Ali Da Reaper

Lola Crystals presents a BIG BLACK COCK Sissy Whore to Ali Da Reaper

TrannyGem 1 year ago

Bedtime for Sissy Taylor

Bedtime for Sissy Taylor

XHamster 6 months ago

Kink Studios Tour Guide Porn

Kink Studios Tour Guide Porn

XHamster 2 months ago

Susan is playing with Cameron's bum

Susan is playing with Cameron's bum

TransTube.tv 2 years ago

ts ria bentley gets pegged and pissed on by gothess bri

ts ria bentley gets pegged and pissed on by gothess bri

PissVids 2 years ago

Femboy Missionary Feminization on the Ladder of a Sex Dungeon

Femboy Missionary Feminization on the Ladder of a Sex Dungeon

XHamster 3 weeks ago

Sophia Loreen Party on Jun 3, 2026 - Part 3

66% HD 2:00 / 21:53

Sophia Loreen Party on Jun 3, 2026 - Part 3

Flirt4Free 2 months ago

Lana Page gape training - amateur crossdresser debut (part2)

Lana Page gape training - amateur crossdresser debut (part2)

XHamster 5 years ago

Happy sissy perplexed by multiple sissygasms riding enormous 12.5”/32cm Yam-sized Father faux shaft

Happy sissy perplexed by multiple sissygasms riding enormous 12.5”/32cm Yam-sized Father faux shaft

Transvids.tv 1 year ago

TGIRL IN A HOODIE HUMPS A UNSHAVED RAVE FEMBOY

TGIRL IN A HOODIE HUMPS A UNSHAVED RAVE FEMBOY

TrannyGem 10 months ago

College jock bangs his trans gym coach Brittney Kade in raw anal action

College jock bangs his trans gym coach Brittney Kade in raw anal action

WeGotDicks 3 weeks ago

TANGENTOD - Stretching and Filling Fuckpet Holes With Belt

TANGENTOD - Stretching and Filling Fuckpet Holes With Belt

PornFreeNow 3 weeks ago

Fucking Machine Dildo Test ft. Sissy Rosie

44% HD 0:39 / 6:45

Fucking Machine Dildo Test ft. Sissy Rosie

FapHouse 4 months ago

mmd r18 cute Haku was trained to be king dick vacuum cleaner 3d hentai

mmd r18 cute Haku was trained to be king dick vacuum cleaner 3d hentai

HentaiGem 4 years ago

Lucky Big Ass Sissy Slut Fucked by Mistress Jenna Until He Cums Over Her Fat Strapon Cock!

Lucky Big Ass Sissy Slut Fucked by Mistress Jenna Until He Cums Over Her Fat Strapon Cock!

XHamster 1 year ago

Sissy Jessica Bloom Spitroast Training With Fucking Machine And Dildos - Anal Sissygasms and Cumswallow

Sissy Jessica Bloom Spitroast Training With Fucking Machine And Dildos - Anal Sissygasms and Cumswallow

XHamster 4 months ago

Reina Hanno Anal Kegel Training Trailer

Reina Hanno Anal Kegel Training Trailer

XHamster 3 years ago

Elias & Elix Private Show

51% HD 2:00 / 37:58

Elias & Elix Private Show

Flirt4Free 1 year ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Camster 1 month ago

Real life sissy training

Real life sissy training

XHamster 5 years ago

Colombian Boys Party on May 26, 2026 - Part 2

63% HD 2:00 / 49:43

Colombian Boys Party on May 26, 2026 - Part 2

Flirt4Free 3 months ago

Masturbation pantyhose trans

Masturbation pantyhose trans

XHamster 3 years ago

Shemale in fishnets rides dildo till she cums - Amateur Solo

Shemale in fishnets rides dildo till she cums - Amateur Solo

AnySex 2 years ago

QOS Sissy Lola Crystals gets 2nd internal cumshot from SUPREME-SIZED BIG BLACK COCK Fuckbuddy

QOS Sissy Lola Crystals gets 2nd internal cumshot from SUPREME-SIZED BIG BLACK COCK Fuckbuddy

TransTube.tv 1 year ago

Mesmeriza Compilation 11 Island of Desires

Mesmeriza Compilation 11 Island of Desires

XHamster 1 year ago

AB110 New Year Furniture Human Table blowjow cumshot,squirting

AB110 New Year Furniture Human Table blowjow cumshot,squirting

XHamster 2 years ago

Alejandra Fox Private Show

Alejandra Fox Private Show

Camster 3 weeks ago

Lizz_ss25 changed sissy play

Lizz_ss25 changed sissy play

XHamster 2 years ago

FAT BOOTY Sissy rides dildo HARD with CREAMY GAPE

FAT BOOTY Sissy rides dildo HARD with CREAMY GAPE

XHamster 4 years ago

Jessica Simpsin Party on Dec 29, 2019

65% HD 2:00 / 1:15:26

Jessica Simpsin Party on Dec 29, 2019

Camster 6 years ago

Sissy Slut Anal Destruction

49% HD 1:01 / 19:58

Sissy Slut Anal Destruction

FapHouse 1 year ago

Orgy and trains of the CentoXCento with the trans Sabrina Pa

Orgy and trains of the CentoXCento with the trans Sabrina Pa

Tranny.one 3 years ago

Sean Collinss Private Show

64% HD 2:00 / 7:51

Sean Collinss Private Show

Flirt4Free 9 months ago

Femdom Dildo Encouragement Suck my Dick Sissy POV Rollplay

Femdom Dildo Encouragement Suck my Dick Sissy POV Rollplay

XHamster 3 years ago

becomingfemme - bunny summers tranny pimped out and fucked hard

becomingfemme - bunny summers tranny pimped out and fucked hard

TransDoe 2 years ago

Lily Wow Party on Aug 26, 2026 - Part 3

4K 2:00 / 17:08

Lily Wow Party on Aug 26, 2026 - Part 3

Camster 18 hours ago

”A Gym Just For Us 2”

”A Gym Just For Us 2”

TransHero 8 months ago

BBC Ebony Dominatrix Mounts Her Kitten & Rides Until ANAL Fisting Blows Her Mind

BBC Ebony Dominatrix Mounts Her Kitten & Rides Until ANAL Fisting Blows Her Mind

TransTube.tv 2 months ago

Asian Submissive Ladyboy First Anal Casting & Slave Training

Asian Submissive Ladyboy First Anal Casting & Slave Training

XHamster 1 month ago

Sissy In Blue Riding Her Dildos

Sissy In Blue Riding Her Dildos

XHamster 7 months ago

Ring Gag Mouth Nail Instructing by latexslavecgn

Ring Gag Mouth Nail Instructing by latexslavecgn

MenGem 2 years ago

Slave fucking and dick locked in chastity belt

Slave fucking and dick locked in chastity belt

XHamster 1 year ago

Aleex & Paulo Private Show

52% HD 2:00 / 8:12

Aleex & Paulo Private Show

Flirt4Free 1 year ago

Sissy - Feminization - Sissy Trainer - Sissification

Sissy - Feminization - Sissy Trainer - Sissification

TrannyGem 3 years ago

No.292 Nighttime Punishment Training

No.292 Nighttime Punishment Training

XHamster 1 week ago

BBC Anal in Doggy with Sissy Hotty KimsaTrans

BBC Anal in Doggy with Sissy Hotty KimsaTrans

ShemaleSin 5 years ago

Drivers class ends with a hard anal - Finn Harding , Amanda Riley

Drivers class ends with a hard anal - Finn Harding , Amanda Riley

Fapnado 3 years ago

Sissy Training by Queen Daralis Part 3

Sissy Training by Queen Daralis Part 3

XHamster 6 months ago

Crossdresser gets machined and gaped by huge dildo on fuckingmachine, leaking cock.

Crossdresser gets machined and gaped by huge dildo on fuckingmachine, leaking cock.

XHamster 1 year ago

Bimbo Slut Training, Part 4: Anal Training - Goddess Lilith

61% HD 0:10 / 11:40

Bimbo Slut Training, Part 4: Anal Training - Goddess Lilith

LoyalFans 5 months ago

tgirl in fishnet plows herself with her toy until she spunks - Emily Adaire's ass fucking training - day 5

tgirl in fishnet plows herself with her toy until she spunks - Emily Adaire's ass fucking training - day 5

TransTube.tv 2 years 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

Sissy College girl Gets Destroyed and Creampied by BIG BLACK COCK

Sissy College girl Gets Destroyed and Creampied by BIG BLACK COCK

TransTube.tv 1 year 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 1 year ago

Young Trans Girl Is Dancing On A 11-inch BBC Dildo

Young Trans Girl Is Dancing On A 11-inch BBC Dildo

XHamster 3 years ago

becomingfemme - aliza breeze black transgirl trained to be subservient

becomingfemme - aliza breeze black transgirl trained to be subservient

TransDoe 2 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

PissVids 1 year ago

Luna Completes Entire Anal Training Faproulette And Destroys Her Hole!! [full]

Luna Completes Entire Anal Training Faproulette And Destroys Her Hole!! [full]

AbTranny 3 months ago

Celeste & Liz Private Show

63% HD 2:00 / 4:37

Celeste & Liz Private Show

Flirt4Free 3 years ago

booty total of meaty stud-meat sissy fag supah-slut riding huge humungous manmeat

booty total of meaty stud-meat sissy fag supah-slut riding huge humungous manmeat

Gay4Porn 10 months ago

Two creampies in one morning from two strangers! Filling up Sonya&#039;s hole in a rented apartment. Clip 1

Two creampies in one morning from two strangers! Filling up Sonya&#039;s hole in a rented apartment. Clip 1

XHamster 5 months ago

Tranny camgirl training her butt and throat

Tranny camgirl training her butt and throat

XXXShemalePorn 4 years ago

The Only Way A Sissy Should Be Instructed To Jizz

The Only Way A Sissy Should Be Instructed To Jizz

TrannyGem 2 years ago

Bigass MILF fucked by petite Trans

Bigass MILF fucked by petite Trans

Some.Porn 11 months ago

2B gives special 9S training

2B gives special 9S training

XHamster 2 months ago

Extremes Sissy ANAL Training

Extremes Sissy ANAL Training

XHamster 1 year ago

Kitty training her ass💗

Kitty training her ass💗

AShemaleTube 1 year ago

Long intense machine fuck for crossdresser anal cunt Clip 1

Long intense machine fuck for crossdresser anal cunt Clip 1

XHamster 8 months ago

Nastya Blue Private Show

HD 2:00 / 16:38

Nastya Blue Private Show

Flirt4Free 2 years ago

Personal Trainer Fucks The Hell Out Of A T-Gal

Personal Trainer Fucks The Hell Out Of A T-Gal

Sheshaft 6 years ago

”GENDER X Shemale cheerleader rides on big black cock - Smash Thompson,Ella Hollywood”

”GENDER X Shemale cheerleader rides on big black cock - Smash Thompson,Ella Hollywood”

Fapnow 4 years ago

Two Shemales Wrestling Training Turns In To Domination Anal Sex Clip 1

Two Shemales Wrestling Training Turns In To Domination Anal Sex Clip 1

XHamster 4 months ago

Domme Feminizes Then Fucks Sissy

Domme Feminizes Then Fucks Sissy

XHamster 1 month ago

Luke Hardy & Cristian Ford Private Show

65% 4K 2:00 / 9:29

Luke Hardy & Cristian Ford Private Show

Flirt4Free 4 months ago

Mooc-022 I Captivated The Frustrated Penis Of The Fair-skinned Trans Woman Who Lives Nearby And Whom I Admired, By Restraining Her And Training Her With A Sex Toy Machine, Leaving Her To Orgasm And Ejaculate Repeatedly, Making Her Fall In Love With Me. (s

Mooc-022 I Captivated The Frustrated Penis Of The Fair-skinned Trans Woman Who Lives Nearby And Whom I Admired, By Restraining Her And Training Her With A Sex Toy Machine, Leaving Her To Orgasm And Ejaculate Repeatedly, Making Her Fall In Love With Me. (s

GetTranny 1 month ago

Sophia Loreen Party on Aug 24, 2026 - Part 3

4K 2:00 / 59:20

Sophia Loreen Party on Aug 24, 2026 - Part 3

Flirt4Free 2 days ago

BBC GIFTED GYM PERSONAL FUCKED MY ASS AFTER TRAINING

BBC GIFTED GYM PERSONAL FUCKED MY ASS AFTER TRAINING

AShemaleTube 4 months ago

*Trailer* Sissy Instructing Basics With Kelli Frost

*Trailer* Sissy Instructing Basics With Kelli Frost

TrannyGem 4 years ago

Adorable Yam-Sized Culo Trans Doll Assfuck Gaped Open

Adorable Yam-Sized Culo Trans Doll Assfuck Gaped Open

TrannyGem 4 years ago

Nun Cums on Sex Machine

Nun Cums on Sex Machine

XHamster 2 years ago

Emily Leah Party on Apr 22, 2025

4K 2:00 / 1:50:07

Emily Leah Party on Apr 22, 2025

Camster 1 year ago

TS Nadia Love dominated by Goddess Tangent

TS Nadia Love dominated by Goddess Tangent

XHamster 3 months ago

Mesmeriza Compilation 11 Island of Desires

Mesmeriza Compilation 11 Island of Desires

XHamster 1 year ago

my homework six

my homework six

TrannyGem 4 years ago

Crossdresser slut anal training with nipple pumps and big dildos

Crossdresser slut anal training with nipple pumps and big dildos

ManPorn 2 years ago

Blonde Femboy Crossdresser In An Abandoned Hospital

Blonde Femboy Crossdresser In An Abandoned Hospital

XHamster 4 months ago

Extreme anal gape with pig hole, dildo and inflatable plug

Extreme anal gape with pig hole, dildo and inflatable plug

XGroovy 3 years ago

sex machine and anal, cute femboy cums hands free from hard butt banging

sex machine and anal, cute femboy cums hands free from hard butt banging

ShemaleSin 4 years ago

brazilian trans slave training & anal creampie fisting

64% 1:59 / 20:00

brazilian trans slave training & anal creampie fisting

AnalVids 7 months ago

Margaux Fox Private Show

HD 2:00 / 14:58

Margaux Fox Private Show

Flirt4Free 4 years ago

Daily Routine with the Machine

Daily Routine with the Machine

XHamster 1 year ago

Hot Ass Sissy. Riding Big Long Toy Deep and Good

Hot Ass Sissy. Riding Big Long Toy Deep and Good

XHamster 1 week ago

Bashful Lara plays with 2 PLAYTHINGS and CRAMS FUCKHOLE with UNDIES

Bashful Lara plays with 2 PLAYTHINGS and CRAMS FUCKHOLE with UNDIES

5Gays 10 months ago

Long intense machine fucking for sexy Crossdresser

Long intense machine fucking for sexy Crossdresser

XHamster 2 years ago

Domina makes sissy from girlz professional gargle fake penis and then plows her rear end fashion

Domina makes sissy from girlz professional gargle fake penis and then plows her rear end fashion

TrannyGem 2 years ago

Latex Domination and Sissy Training

Latex Domination and Sissy Training

TransTube.tv 2 months ago

Sissy Mega-slut Lola Crystals in BIG BLACK COCK Heaven

Sissy Mega-slut Lola Crystals in BIG BLACK COCK Heaven

TransTube.tv 1 year ago

Pretty Ebony TS Teen TGND Trains Her Sweet Asshole

Pretty Ebony TS Teen TGND Trains Her Sweet Asshole

Eporner 6 months ago

Big Dick Man Fuck with Dildo

Big Dick Man Fuck with Dildo

FapHouse 3 days ago

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