Anal Training Videos (90,534)

Sissygasm Guide & How A Good Slut Cleans Up Jessica Bloom

Sissygasm Guide & How A Good Slut Cleans Up Jessica Bloom

XHamster 4 years ago

Chastity Sissy Games: Pegging and Pleasure in Cage Mistress Julia femdom

Chastity Sissy Games: Pegging and Pleasure in Cage Mistress Julia femdom

XHamster 2 years ago

Sissy UwU solo masturbation 39 mtf British Anal Masturbation Trans flat chastity cages toys

Sissy UwU solo masturbation 39 mtf British Anal Masturbation Trans flat chastity cages toys

XHamster 3 weeks ago

Anal Beads, Buttplug and Huge Dildo - Anal Training Cumslut Jessica Bloom

Anal Beads, Buttplug and Huge Dildo - Anal Training Cumslut Jessica Bloom

XHamster 1 year ago

Blonde Stepmom Cumshot

Blonde Stepmom Cumshot

FapHouse 1 week ago

Self-Training No70 Outdoor Masturbation Machine

Self-Training No70 Outdoor Masturbation Machine

XHamster 7 months ago

Fitness training session with the hot stud turns into a hot anal fuck show with the beautiful TS chick

Fitness training session with the hot stud turns into a hot anal fuck show with the beautiful TS chick

Tranny.one 4 years ago

Milfs Anal Training - Teaser Video

Milfs Anal Training - Teaser Video

XMilf 3 years ago

Sophia Loreen Party on Aug 14, 2026 - Part 5

4K 2:00 / 49:16

Sophia Loreen Party on Aug 14, 2026 - Part 5

Camster 1 week ago

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 19

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 19

XHamster 7 months ago

Petra,s last exam (incl pis training,fist, giant sex tool and greater quantity ;-)

Petra,s last exam (incl pis training,fist, giant sex tool and greater quantity ;-)

Amateur8 8 months ago

Long Intense Anal Machine Fuck with Big Dildo, Crossdresser Bi Guy

HD 1:01 / 10:10

Long Intense Anal Machine Fuck with Big Dildo, Crossdresser Bi Guy

FapHouse 2 years ago

Anal Slut Turns His Boypussy Into a Gaping Hole

Anal Slut Turns His Boypussy Into a Gaping Hole

XHamster 1 year ago

Big booty Femboy Raven Wedgie and Big Anal Gape with Inflatable Dildo

Big booty Femboy Raven Wedgie and Big Anal Gape with Inflatable Dildo

XHamster 6 months ago

Sissy cums in chastity and licks it all up

Sissy cums in chastity and licks it all up

XHamster 1 year 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

MOAN like a woman while mistress is PEGGING your SISSY ass

MOAN like a woman while mistress is PEGGING your SISSY ass

XHamster 3 years ago

Anal Training #14 Tanned Femboy Fucks Himself in the Ass and Cums

HD 1:01 / 39:01

Anal Training #14 Tanned Femboy Fucks Himself in the Ass and Cums

FapHouse 1 year ago

Trans Girl Fucks a Pumpkin

Trans Girl Fucks a Pumpkin

XHamster 4 months ago

Archie Blossom Private Show

61% HD 2:00 / 14:11

Archie Blossom Private Show

Flirt4Free 4 months ago

My sissy femdom training

My sissy femdom training

XHamster 1 year ago

Femboy Anal Training

Femboy Anal Training

FapHouse 3 months ago

TS Mariana Lins Rides Maira's Cock

TS Mariana Lins Rides Maira's Cock

Some.Porn 1 year ago

Lesbian Shemale Making Love in Japanese School Uniform

Lesbian Shemale Making Love in Japanese School Uniform

XHamster 1 year ago

Dildo Training deutsch

Dildo Training deutsch

Tranny.one 3 years ago

Sissy Backside Screwed Right Over The Camera Compilation

Sissy Backside Screwed Right Over The Camera Compilation

TransTube.tv 1 year ago

Sissy slut’s deep anal training for big dicks

Sissy slut’s deep anal training for big dicks

XHamster 4 years ago

First time bareback gay sex with older man

First time bareback gay sex with older man

XHamster 2 years ago

Dungeon Bondage Trans Gets Anal Training

Dungeon Bondage Trans Gets Anal Training

FapHouse 4 months ago

Huge Dildo Anal Slut

Huge Dildo Anal Slut

XHamster 1 month ago

Teen Slave Blows Old Master's Hard Cock

Teen Slave Blows Old Master's Hard Cock

Some.Porn 1 year ago

TS Training

XHamster 1 year ago

Petra the hardcore anal floozy (incl dap, tap, fisting and giant sex toy)

Petra the hardcore anal floozy (incl dap, tap, fisting and giant sex toy)

ShemaleSin 6 months ago

Swallow My Farts, Pee and Cum You Dirty Slut! Trans Femdom POV Jessica Bloom

HD 0:39 / 27:15

Swallow My Farts, Pee and Cum You Dirty Slut! Trans Femdom POV Jessica Bloom

FapHouse 14 hours ago

Glam Slut Milking Training 2

62% HD 1:01 / 20:26

Glam Slut Milking Training 2

FapHouse 7 months ago

Sophia Loreen Private Show

58% HD 2:00 / 37:35

Sophia Loreen Private Show

Flirt4Free 4 months ago

Tranny Girl Fucks at Gym Lession with His Coach! Double Cumshot and Cum Into Mouth!

HD 0:39 / 12:50

Tranny Girl Fucks at Gym Lession with His Coach! Double Cumshot and Cum Into Mouth!

FapHouse 7 months 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

An extreme hole, a straight man hammers a point with a huge hand!!!

65% HD 0:39 / 3:01

An extreme hole, a straight man hammers a point with a huge hand!!!

FapHouse 3 years ago

TGIRLS XXX: White Chinaa's Massage Skills

TGIRLS XXX: White Chinaa's Massage Skills

XHamster 4 years ago

NBA All-Star Lola Bunny trains her hole before practice

Premium HD 6:52

NBA All-Star Lola Bunny trains her hole before practice

XVideosRed 5 months ago

Cum Injection and Big Toys for the Perfect Pegging Sissygasm

61% HD 0:39 / 17:34

Cum Injection and Big Toys for the Perfect Pegging Sissygasm

FapHouse 1 year ago

Anal training in chastity and plugged

Anal training in chastity and plugged

AShemaleTube 1 year ago

Charlie Cano Private Show

65% HD 2:00 / 13:13

Charlie Cano Private Show

Flirt4Free 3 years ago

Black Cuckold Sissy Gets Fucked by Wife's Lover

66% HD 0:39 / 24:05

Black Cuckold Sissy Gets Fucked by Wife's Lover

FapHouse 1 year ago

Orgy Gimps sixty nine Dual female dominance Pegging and Sissy Jizzing with Queening on the Fuckmachine

Orgy Gimps sixty nine Dual female dominance Pegging and Sissy Jizzing with Queening on the Fuckmachine

Transvids.tv 1 year ago

Celeste & Liz Private Show

62% HD 2:00 / 5:42

Celeste & Liz Private Show

Camster 3 years ago

Machine Fucking my Gay Slave Count

Machine Fucking my Gay Slave Count

XHamster 5 years ago

Rachael Belle In ass-fuck Trainer

Rachael Belle In ass-fuck Trainer

TransTube.tv 11 months ago

Sub Fan Worships My Sweaty Armpits and Takes My Load Deep

53% HD 0:39 / 33:41

Sub Fan Worships My Sweaty Armpits and Takes My Load Deep

FapHouse 11 months ago

Tatiana & Owen Private Show

Tatiana & Owen Private Show

Camster 3 weeks ago

Imagine You Are Fucking a Boy!

75% HD 1:01 / 12:06

Imagine You Are Fucking a Boy!

FapHouse 1 year ago

Femboy Gaping Her Hole with Massive Pink Buttplug.

Femboy Gaping Her Hole with Massive Pink Buttplug.

FapHouse 2 years ago

Desire Sweet Private Show

HD 2:00 / 23:51

Desire Sweet Private Show

Camster 3 days ago

Multiformity begins her Bad Dragon training with Mastix Miguire

Multiformity begins her Bad Dragon training with Mastix Miguire

SortPorn 1 year ago

Anal Exam

62% HD 1:01 / 25:02

FapHouse 6 months ago

Crossdresser in a Pink Skirt and a Shiny White Corset Fucks His Cunt

Crossdresser in a Pink Skirt and a Shiny White Corset Fucks His Cunt

FapHouse 2 years ago

Sasha de Sade Anal Training On The Leash With BBC

Sasha de Sade Anal Training On The Leash With BBC

DrTuber 6 months ago

Sissy Jessica's Weekly Hole Training 1 (4k)

4K 0:39 / 22:53

Sissy Jessica's Weekly Hole Training 1 (4k)

FapHouse 3 weeks ago

Cristal Kinky Anal Training Sissy

HD 0:39 / 32:19

Cristal Kinky Anal Training Sissy

FapHouse 1 month ago

Trans gf Daniela Chanel penetrates my taut crevice with her phat girlcock.

Trans gf Daniela Chanel penetrates my taut crevice with her phat girlcock.

TrannyGem 1 year ago

Sophia Loreen Private Show

57% HD 2:00 / 4:58

Sophia Loreen Private Show

Flirt4Free 3 months ago

Sissy Dressed up as a Mistress to Get a Sissy of Her Own but Fails

Sissy Dressed up as a Mistress to Get a Sissy of Her Own but Fails

XHamster 1 year ago

Tgirl Sasha De Sade - Advanced Slut Training

Tgirl Sasha De Sade - Advanced Slut Training

GetTranny 3 years ago

XXL dildo games and hard riding

XXL dildo games and hard riding

XHamster 3 months ago

Slutty Asian Femboy in Qipao Gets Red Ass Spanking, Deep Doggy Pounding & Merciless Fucking Machine Training

65% HD 0:39 / 12:45

Slutty Asian Femboy in Qipao Gets Red Ass Spanking, Deep Doggy Pounding & Merciless Fucking Machine Training

FapHouse 3 months ago

Trancess Triss Bended Over on her knees Strettching her Dude Cunt for You

Trancess Triss Bended Over on her knees Strettching her Dude Cunt for You

TrannyGem 4 years ago

sissy ravages herself with a faux-cock in a v-card belt using her spunk as a lube

sissy ravages herself with a faux-cock in a v-card belt using her spunk as a lube

TrannyGem 9 months ago

Sophia Loreen Party on Jun 18, 2026 - Part 4

61% HD 2:00 / 58:05

Sophia Loreen Party on Jun 18, 2026 - Part 4

Flirt4Free 2 months 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

”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

Sissy Hope is really horny, gets fucked by a huge dildo and rubs her little clitty with vibrator.

Sissy Hope is really horny, gets fucked by a huge dildo and rubs her little clitty with vibrator.

XHamster 4 years ago

korean femboy kimono smashed

korean femboy kimono smashed

Gay4Porn 1 year ago

Sissy Maid All Plugged with Huge Dildo

Sissy Maid All Plugged with Huge Dildo

FapHouse 1 month ago

Having a Hard Time 7: Shemale Jane's Full Body Massage on Anna

64% HD 1:01 / 15:36

Having a Hard Time 7: Shemale Jane's Full Body Massage on Anna

FapHouse 6 months ago

TheArtemixx - Jayla's 1st Monster Dong Training - Thick Trans Lalin girl Takes ArtemiXXX's BBC and Hawt Load

TheArtemixx - Jayla's 1st Monster Dong Training - Thick Trans Lalin girl Takes ArtemiXXX's BBC and Hawt Load

SortPorn 1 month ago

Anal slut prolapse on inflatable butt plug

Anal slut prolapse on inflatable butt plug

XHamster 7 months ago

Sissy Trainer - Sissy - Feminization - Sissification

Sissy Trainer - Sissy - Feminization - Sissification

TrannyGem 3 years ago

SUBMISSIVE ASIAN LADYBOY SLAVE TRAINING &amp_ ANAL CASTING

Premium HD 35:32

SUBMISSIVE ASIAN LADYBOY SLAVE TRAINING &amp_ ANAL CASTING

XVideosRed 4 weeks ago

I fucked his Manpussy with my strap on

I fucked his Manpussy with my strap on

XHamster 1 year ago

Deep Sissy Fisting

71% HD 0:39 / 3:16

Deep Sissy Fisting

FapHouse 1 year ago

transgirl yasmin lee from movie hangover 2 hardcore sextape

transgirl yasmin lee from movie hangover 2 hardcore sextape

TransDoe 2 years ago

Femboy Ben Tennyson Massive Anal Creampie Cumfarts and Wedgie with High Heels

HD 0:39 / 21:56

Femboy Ben Tennyson Massive Anal Creampie Cumfarts and Wedgie with High Heels

FapHouse 2 days ago

Tv Isabella's Compilation Y-Training Scheme

Tv Isabella's Compilation Y-Training Scheme

AShemaleTube 10 months ago

Arab Sissy Crossdresser Pummeled by BIG BLACK COCK Father & Cum shot

Arab Sissy Crossdresser Pummeled by BIG BLACK COCK Father & Cum shot

TransTube.tv 2 years ago

Giant Hole Stretching!!

Giant Hole Stretching!!

XHamster 8 months ago

This Video Is the 1st in a Series of Nyxi Leon's Very First Transformation Ever

45% HD 0:39 / 25:41

This Video Is the 1st in a Series of Nyxi Leon's Very First Transformation Ever

FapHouse 1 year ago

Trans Is Fucked by Her Fuck Machine While Using Her Cage

HD 0:39 / 14:31

Trans Is Fucked by Her Fuck Machine While Using Her Cage

FapHouse 1 year ago

Lika Kai Private Show

58% 4K 2:00 / 8:58

Lika Kai Private Show

Camster 1 week ago

Sissy anal training

Sissy anal training

AShemaleTube 2 years ago

FEMDOM SISSY TRAINNING COMPILATION CUMSHOTS SISSYGASM

FEMDOM SISSY TRAINNING COMPILATION CUMSHOTS SISSYGASM

ShemaleSin 2 years ago

French Cuckold Wife and Lesbian Anal Sissy

44% 1:01 / 5:08

French Cuckold Wife and Lesbian Anal Sissy

FapHouse 2 years ago

STRETCH & SHAME: ANAL TRAINING SESSION

STRETCH & SHAME: ANAL TRAINING SESSION

LoyalFans 5 days ago

Huge Ass Tiny Dick Crossdresser Trainning Her Hole

Huge Ass Tiny Dick Crossdresser Trainning Her Hole

FapHouse 2 weeks ago

Sophia Loreen Party on Jul 30, 2026 - Part 3

57% 4K 2:00 / 42:41

Sophia Loreen Party on Jul 30, 2026 - Part 3

Camster 3 weeks ago

51cm John Thomas Henry Humungous Assfuck Destruction Fuck Stick Slamming Deep into Slick Nice Femboy Asspussy

51cm John Thomas Henry Humungous Assfuck Destruction Fuck Stick Slamming Deep into Slick Nice Femboy Asspussy

TrannyGem 2 years ago

TANGENTOD - Stretching and Filling Fuckpet Holes With Belt

TANGENTOD - Stretching and Filling Fuckpet Holes With Belt

PornFreeNow 3 weeks ago

becomingfemme - bunny summers tranny pimped out and fucked hard

becomingfemme - bunny summers tranny pimped out and fucked hard

TransDoe 2 years ago

Re:Zero Rem Anal training and Blowjob part.2

Re:Zero Rem Anal training and Blowjob part.2

XHamster 3 years ago

Petra,s 6th training

Petra,s 6th training

XHamster 1 year ago

AB104 Sex toy tester surrender (English subtitles)

AB104 Sex toy tester surrender (English subtitles)

Tranny.one 2 years ago

Latex-Crossdresser Analtraining intens long machine fuck

Latex-Crossdresser Analtraining intens long machine fuck

XHamster 2 years ago

Nyxi Leon Does a Hot Solo with Her New Rubberized Chastity

76% HD 1:01 / 8:19

Nyxi Leon Does a Hot Solo with Her New Rubberized Chastity

FapHouse 1 year ago

Quick Anal Session

Quick Anal Session

XHamster 3 months ago

becomingfemme - bunny summers now her trans life has purpose

becomingfemme - bunny summers now her trans life has purpose

TransDoe 2 years ago

Husband sissified, bent over and made to spread his ass cheeks for mistress's big cock to pound his tight boi pussy

Husband sissified, bent over and made to spread his ass cheeks for mistress's big cock to pound his tight boi pussy

XHamster 2 years ago

Sissy starting to fuck

Sissy starting to fuck

XHamster 8 months ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 2 years ago

Sissy Anal Training by Latex Dommes

71% 0:39 / 10:39

Sissy Anal Training by Latex Dommes

FapHouse 1 year ago

Femboy Cumdump Pushes out Gallons of Cum

Femboy Cumdump Pushes out Gallons of Cum

XHamster 2 years ago

Trans Latina Teen Loses Virginity

Trans Latina Teen Loses Virginity

XHamster 6 months ago

Sissy latexdoll pissing and anal training

Sissy latexdoll pissing and anal training

XHamster 4 years ago

Fresh pet Amber Shock gets corded up and assfucking penetrated by Ciren Verde and Lora Cross

Fresh pet Amber Shock gets corded up and assfucking penetrated by Ciren Verde and Lora Cross

TrannyGem 4 years ago

Tatiana & Owen Private Show

Tatiana & Owen Private Show

Camster 6 days ago

Anal Exam

HD 0:39 / 25:02

FapHouse 6 months ago

Marian & Richard Private Show

67% HD 2:00 / 5:27

Marian & Richard Private Show

Flirt4Free 2 months ago

Chastity Cum and Squirt for Bnwo Sissy

65% HD 1:01 / 5:59

Chastity Cum and Squirt for Bnwo Sissy

FapHouse 1 week ago

Honeypot Teaching

Honeypot Teaching

TrannyGem 5 years ago

Doggy Training... Will He Obey?

64% HD 1:01 / 15:52

Doggy Training... Will He Obey?

FapHouse 1 year ago

Trans Ria Bentley Succumbs to Raw Anal by Gigantic Bull

Trans Ria Bentley Succumbs to Raw Anal by Gigantic Bull

XHamster 6 months ago

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