Sissy Anal Training Videos (62,933)

Sissy Slut Machine Fucked Milked in Chastity Self Cum Swallow

72% HD 1:01 / 24:03

Sissy Slut Machine Fucked Milked in Chastity Self Cum Swallow

FapHouse 3 months ago

Sissy Slut Anal Destruction

46% HD 1:01 / 19:58

Sissy Slut Anal Destruction

FapHouse 1 year ago

Paulo & Jose & Sander Private Show

55% HD 2:00 / 15:24

Paulo & Jose & Sander Private Show

Flirt4Free 4 months ago

Futa Groves - Gameplay - Roleplay - Big Dick Futa Gets Blowjob and Sissy Gets Humilated by Her Girlfriend

Futa Groves - Gameplay - Roleplay - Big Dick Futa Gets Blowjob and Sissy Gets Humilated by Her Girlfriend

FapHouse 6 days ago

My Butt Is Made for Anal and Creampies

69% HD 1:01 / 22:24

My Butt Is Made for Anal and Creampies

FapHouse 2 years ago

Caged TS Gray Perrier Submits to Sadistic Sir

63% HD 1:01 / 36:19

Caged TS Gray Perrier Submits to Sadistic Sir

FapHouse 2 months ago

Ladyboy Alice with the Big Dick Gets Anal Training.

55% HD 0:39 / 44:38

Ladyboy Alice with the Big Dick Gets Anal Training.

FapHouse 1 month ago

BBC TRAINING WITH CERJOY

BBC TRAINING WITH CERJOY

XHamster 1 year ago

Feminized to Go to the Club

Feminized to Go to the Club

XHamster 3 months ago

10 unreal public orgasms!!!

HD 0:30 / 17:51

10 unreal public orgasms!!!

AnalVids 2 years ago

Sissy Anal Training with Huge Cock 1

63% HD 1:01 / 5:33

Sissy Anal Training with Huge Cock 1

FapHouse 1 week ago

Whife *

TrannyGem 6 years ago

brazilian trans slave training & anal fisting

brazilian trans slave training & anal fisting

AnalVids 9 months ago

training black sissy aliza to serve a big cock white daddy spitroasting cum in mouth humiliation deep throat bwc

training black sissy aliza to serve a big cock white daddy spitroasting cum in mouth humiliation deep throat bwc

AnalVids 1 month ago

Training a Twink Femboy Noisy Ass with BBC

Training a Twink Femboy Noisy Ass with BBC

XHamster 3 months ago

Serving Mr. Maxxx (thad Fucks Brie Lovely and Ryley Rails)

Serving Mr. Maxxx (thad Fucks Brie Lovely and Ryley Rails)

ShemaleSex 3 months ago

Nicco & Patric & Santiago Private Show

Nicco & Patric & Santiago Private Show

Flirt4Free 2 years ago

Elias & Elix Private Show

50% HD 2:00 / 37:58

Elias & Elix Private Show

Flirt4Free 1 year ago

Jacob Malik Private Show

54% HD 2:00 / 4:28

Jacob Malik Private Show

Flirt4Free 8 months ago

Cute Face Elastic Trans Girl Moaning Like a Slut After Fucking Her Fat Ass and Getting an Anal Creampie

Cute Face Elastic Trans Girl Moaning Like a Slut After Fucking Her Fat Ass and Getting an Anal Creampie

XHamster 1 week ago

Breaking Her Sissy Doll (full 1 Hr 15 Min of Hardcore Femdom) Slut Exposed in Bondage & Chastity for Pegging, Fisting, and Mach

66% HD 1:01 / 1:13:02

Breaking Her Sissy Doll (full 1 Hr 15 Min of Hardcore Femdom) Slut Exposed in Bondage & Chastity for Pegging, Fisting, and Mach

FapHouse 1 month ago

Sissy Slut Training

Sissy Slut Training

XHamster 2 years ago

Artesca Private Show

64% HD 2:00 / 11:07

Artesca Private Show

Flirt4Free 8 months ago

Tarot Tales to Feminization

Tarot Tales to Feminization

XHamster 2 months ago

Submissive Sissy and Mistress

HD 1:01 / 12:10

Submissive Sissy and Mistress

FapHouse 4 days ago

My New Best Toy

My New Best Toy

XHamster 1 year ago

Ep3 Testing My New Sissy: Pegging and More? - Mistress Julia

Ep3 Testing My New Sissy: Pegging and More? - Mistress Julia

FapHouse 1 year ago

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

67% HD 1:01 / 25:41

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

FapHouse 1 year ago

Tyler Blake Sexy Lingerie Ass Stretching & Solo Fisting

62% HD 0:39 / 1:16

Tyler Blake Sexy Lingerie Ass Stretching & Solo Fisting

FapHouse 4 months ago

Sissy cheerleader training for BBC

Sissy cheerleader training for BBC

XHamster 1 week ago

Caged TS Gray Perrier Submits to Sadistic Sir

Caged TS Gray Perrier Submits to Sadistic Sir

XHamster 1 month ago

Luke Hardy & Cristian Ford Private Show

Luke Hardy & Cristian Ford Private Show

Flirt4Free 2 years ago

Trans Girl Bimbo Slut Riding 10-inch BBC while on a Phone Call

Trans Girl Bimbo Slut Riding 10-inch BBC while on a Phone Call

XHamster 3 years ago

Sophia Loreen Private Show

56% HD 2:00 / 10:44

Sophia Loreen Private Show

Flirt4Free 2 years ago

Her Chastity Cage Flops Around While Her Asshole is Stretched Beyond Recognition! Clip 1

Her Chastity Cage Flops Around While Her Asshole is Stretched Beyond Recognition! Clip 1

XHamster 1 month ago

Brides Hands-free BBC Cumshots

80% HD 0:39 / 4:53

Brides Hands-free BBC Cumshots

FapHouse 5 months ago

Happy Birthday Lola

Happy Birthday Lola

XHamster 4 months ago

White Femboy Showing On Webcam

White Femboy Showing On Webcam

XHamster 1 week ago

Sissygasm Training 2

Sissygasm Training 2

XHamster 1 year ago

Ultimate Sissy Fuck Doll Trainer

Ultimate Sissy Fuck Doll Trainer

XHamster 7 months ago

Compilation Of White Sissy Cockslut Training Part 1

Compilation Of White Sissy Cockslut Training Part 1

Eporner 1 week ago

Hot shemale teenager cowgirl railing a faux penis, Handsfree jizzing big dick

Hot shemale teenager cowgirl railing a faux penis, Handsfree jizzing big dick

MyTransfix 1 month ago

SISIFICATION, BBC ADDICTED Submissive Training Part 2 (Your ANUS Will Receive A Big, Thick And Very Veiny Cock) Sissy Training

SISIFICATION, BBC ADDICTED Submissive Training Part 2 (Your ANUS Will Receive A Big, Thick And Very Veiny Cock) Sissy Training

BeMyHole 1 year ago

Mature tarnny destroys Jiggly emilys crevices

Mature tarnny destroys Jiggly emilys crevices

TrannyGem 4 years ago

Latex sissy training

Latex sissy training

ShemaleSin 3 weeks ago

Paulo & Jose & Sander Private Show

52% HD 2:00 / 7:57

Paulo & Jose & Sander Private Show

Flirt4Free 5 months ago

Gorgeous T-girl Sluts Out with Huge Dildo Hard Anal, Gapes, Pushing Out Cum

Gorgeous T-girl Sluts Out with Huge Dildo Hard Anal, Gapes, Pushing Out Cum

XHamster 8 months ago

Blowjob Ends with Cum in the Mouth

59% HD 2:00 / 19:15

Blowjob Ends with Cum in the Mouth

Flirt4Free 2 years ago

Lesbian Shemale Making Love in Japanese College Uniform

67% 1:01 / 35:44

Lesbian Shemale Making Love in Japanese College Uniform

FapHouse 1 year ago

Slutty Training Class 303! Feat: Ryley Rails

Slutty Training Class 303! Feat: Ryley Rails

XHamster 1 month ago

Fisting Hole !!

Fisting Hole !!

XHamster 1 year ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 1 year ago

What's happening behind the bar table? Training my balls in cage and sissy pussy with a vibrator wand.

What's happening behind the bar table? Training my balls in cage and sissy pussy with a vibrator wand.

XHamster 1 week ago

She Will Take Care of Her Trans Slave During a Medical Examination

She Will Take Care of Her Trans Slave During a Medical Examination

XHamster 10 months ago

Nyxi's 1st Week as Nyxi - Day 3 Lots of Fun Here in the 38 Minute Video.

80% HD 1:01 / 28:51

Nyxi's 1st Week as Nyxi - Day 3 Lots of Fun Here in the 38 Minute Video.

FapHouse 1 year ago

Brutus K Private Show

HD 2:00 / 26:14

Brutus K Private Show

Flirt4Free 10 years ago

Angel Joseph Private Show

Angel Joseph Private Show

Flirt4Free 6 days ago

The Perfect POV for You

The Perfect POV for You

XHamster 1 week ago

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

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

XHamster 2 months ago

Pregnant Blonde Sissy Femboy Massive Anal Creampie after being Blacked with BBC Dildo

Pregnant Blonde Sissy Femboy Massive Anal Creampie after being Blacked with BBC Dildo

XHamster 1 week ago

Can Barely Stand Anymore... My Legs Are Still Shaking After That

77% 1:01 / 6:20

Can Barely Stand Anymore... My Legs Are Still Shaking After That

FapHouse 7 months ago

KiraFri teaches her sissy how to please her mistress with a hardcore pegging session

KiraFri teaches her sissy how to please her mistress with a hardcore pegging session

TrannyMovs 3 weeks ago

cumShow

Flirt4Free 4 years ago

Black Playboy Lingerie Dildo Fun

Black Playboy Lingerie Dildo Fun

XHamster 3 months ago

Sissy Transformation

Sissy Transformation

XHamster 1 week ago

Your Friends Futa Mom Takes Your Butt At Sleepover

Your Friends Futa Mom Takes Your Butt At Sleepover

MyTransfix 3 weeks ago

Opening Pinky Hole, Riding and Fucking

55% HD 2:00 / 9:20

Opening Pinky Hole, Riding and Fucking

Flirt4Free 6 months ago

Jacob Malik Private Show

57% HD 2:00 / 8:46

Jacob Malik Private Show

Flirt4Free 7 months ago

Make me your fuckdoll

Make me your fuckdoll

XHamster 2 weeks ago

arse utter of big trunk sissy faggot mega-bitch railing enormous gigantic trunk

arse utter of big trunk sissy faggot mega-bitch railing enormous gigantic trunk

5Gays 1 year ago

SometimesNiki dildos in crotchless panties

SometimesNiki dildos in crotchless panties

XHamster 1 year ago

Double Domme Spitroast On Our Trans Slut Crystal Bellini

Double Domme Spitroast On Our Trans Slut Crystal Bellini

Clips4sale 7 months ago

Training a Twink Femboy Noisy Ass with BBC

Training a Twink Femboy Noisy Ass with BBC

XHamster 2 months ago

Fuck Us Both Billy

Fuck Us Both Billy

XHamster 1 year ago

Pissing and Pegging My Sissy Slave

Pissing and Pegging My Sissy Slave

XHamster 3 years ago

TS Femdom Dick And Asshole Worship Closeup POV CEI Humiliation

TS Femdom Dick And Asshole Worship Closeup POV CEI Humiliation

ShemaleSex 2 weeks ago

Nymph TEAR UP T-MODEL NUN compilation

Nymph TEAR UP T-MODEL NUN compilation

TransTube.tv 2 years ago

Sissy Fuckdoll Delivery

Sissy Fuckdoll Delivery

TransTube.tv 1 year ago

Anal training!

ShemaleSex 1 day ago

Get ready to work your tight sissy hole with a bottle in your backside while your mistress dominates you with toys and handjobs

Get ready to work your tight sissy hole with a bottle in your backside while your mistress dominates you with toys and handjobs

TrannyMovs 2 weeks ago

Spandexfemboy - Anal Destruction Part 2 BBC Dildo

Spandexfemboy - Anal Destruction Part 2 BBC Dildo

XHamster 1 year ago

Sara Gutierrez Private Show

Sara Gutierrez Private Show

Flirt4Free 4 years ago

Sissy Playing With Her Asspussy

Sissy Playing With Her Asspussy

XHamster 2 months ago

My Butt Is Made for Anal and Creampies

My Butt Is Made for Anal and Creampies

XHamster 1 month ago

Grayce Blossoms Private Show

Grayce Blossoms Private Show

Flirt4Free 1 year ago

Inexperienced CD sissy training with fucktoy

Inexperienced CD sissy training with fucktoy

WebcamBros 5 months ago

Strapon Like Pinishment Sissy by Mistress on Kitchen

Strapon Like Pinishment Sissy by Mistress on Kitchen

XHamster 3 weeks ago

Sissy under training

Sissy under training

XHamster 1 week ago

Sissygasm for Domina

Sissygasm for Domina

XHamster 1 year ago

Sara Gutierrez Private Show

Sara Gutierrez Private Show

Flirt4Free 4 years ago

Russian sissy training camp

Russian sissy training camp

Eporner 1 year ago

Netlifx and Chill Date With Ria Bentley

72% 4K 0:27 / 21:07

Netlifx and Chill Date With Ria Bentley

Clips4sale 2 years ago

Paulo & Jose & Sander Private Show

Paulo & Jose & Sander Private Show

Flirt4Free 4 months ago

Kinky tranny in skirt and stockings bouncing on a huge dildo compilation

Kinky tranny in skirt and stockings bouncing on a huge dildo compilation

XGroovy 1 month ago

CurvySissy69 - sissy in pink riding dildo and ass to mouth Clip 3

CurvySissy69 - sissy in pink riding dildo and ass to mouth Clip 3

XHamster 1 month ago

Latina Crossdresser Enjoys Intense Anal Round Up

Latina Crossdresser Enjoys Intense Anal Round Up

PornFreeNow 4 days ago

Carmen Masterz humiliates a boy by showering him with hot jizz as a reward for being a good boy

Carmen Masterz humiliates a boy by showering him with hot jizz as a reward for being a good boy

TrannyMovs 1 year ago

Short Compilation of Me Riding BBC

Short Compilation of Me Riding BBC

FapHouse 11 months ago

Cute Face Elastic Trans Girl Moaning Like a Slut After Fucking Her Fat Ass and Getting an Anal Creampie

Cute Face Elastic Trans Girl Moaning Like a Slut After Fucking Her Fat Ass and Getting an Anal Creampie

XHamster 1 week ago

Sophia Loreen Party on Sep 10, 2026 - Part 3

4K 2:00 / 23:02

Sophia Loreen Party on Sep 10, 2026 - Part 3

Flirt4Free 1 month ago

Luccas & Jhordy Private Show

60% HD 2:00 / 7:43

Luccas & Jhordy Private Show

Flirt4Free 1 year ago

Caged TS Gray Perrier Submits to Sadistic Sir

Caged TS Gray Perrier Submits to Sadistic Sir

ShemaleSex 1 month ago

Latina Sissy Dildo Ass to mouth in red lingerie

Latina Sissy Dildo Ass to mouth in red lingerie

ShemaleSex 2 weeks ago

Anal Training Night

Anal Training Night

XHamster 1 year ago

POV: Young Gothic Sissy Girl Comes Home And Takes Care Of Your Cock

POV: Young Gothic Sissy Girl Comes Home And Takes Care Of Your Cock

XHamster 1 year ago

JOI Jerk off Instruction and Sissification for Newbie Slut

JOI Jerk off Instruction and Sissification for Newbie Slut

XHamster 1 year ago

My Biggest Anal Dildo Training Vf

My Biggest Anal Dildo Training Vf

XHamster 1 year 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 ;-)

SortPorn 10 months ago

Double Fuck for Sissy Hole

Double Fuck for Sissy Hole

XHamster 10 months ago

Instructing Your Sissy

Instructing Your Sissy

TransTube.tv 3 months ago

Wondrous Fem Dom and Mature Shemale Predominate and Fem a Sissy

Wondrous Fem Dom and Mature Shemale Predominate and Fem a Sissy

TrannyGem 5 years ago

Sissy In Black Riding Her Dildos

Sissy In Black Riding Her Dildos

XHamster 9 months ago

Chastity Sissy Floozy Training - Jessica Bloom Giant Anal Climax

Chastity Sissy Floozy Training - Jessica Bloom Giant Anal Climax

ShemaleSin 2 years ago

Jhordy & Maxx Private Show

44% HD 2:00 / 33:20

Jhordy & Maxx Private Show

Flirt4Free 1 year ago

She trains her sissy friend to receive cocks

She trains her sissy friend to receive cocks

XHamster 1 year ago

Inflatable Butt Plugs - Extreme Anal Expansion

Inflatable Butt Plugs - Extreme Anal Expansion

XHamster 3 weeks ago

She's Going to Fist Her Girlfriend Until Her Stomach Moves

65% 0:39 / 7:25

She's Going to Fist Her Girlfriend Until Her Stomach Moves

FapHouse 1 year ago

Bi Slaves Bareback - Blowjobs and Arse Fucking

Bi Slaves Bareback - Blowjobs and Arse Fucking

XHamster 9 months ago

Sissy cheerleader training for BBC

Sissy cheerleader training for BBC

AShemaleTube 1 week ago

Domina Trans fucks her inexperienced submissive whom she turned into an obedient and deviant slut

Domina Trans fucks her inexperienced submissive whom she turned into an obedient and deviant slut

XHamster 5 months ago

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