Sissy Anal Training - Porn Videos (93,282)

Big-dicked sissy takes it up the ass and swallows his own cum

Big-dicked sissy takes it up the ass and swallows his own cum

XXXShake 3 years ago

Viky & Mateo Private Show

62% HD 2:00 / 19:22

Viky & Mateo Private Show

Flirt4Free 7 months ago

Positive Femdom: Pegging, Fisting to Each Other, Pee. Arya Grander

Positive Femdom: Pegging, Fisting to Each Other, Pee. Arya Grander

XHamster 1 year ago

You Will Beg Me To Link You To This Video. Big Compilation.

You Will Beg Me To Link You To This Video. Big Compilation.

XHamster 3 years ago

Katharine Cane Party on Aug 8, 2026 - Part 3

65% 4K 2:00 / 8:46

Katharine Cane Party on Aug 8, 2026 - Part 3

Camster 4 weeks ago

elf femboy in chastity belt gets tight ass stretched by bbc cock and fuck machine until cum

elf femboy in chastity belt gets tight ass stretched by bbc cock and fuck machine until cum

Lesbian8 1 year ago

Polish femdom trains sissy in strapon pegging and enema

Polish femdom trains sissy in strapon pegging and enema

Yesvids 1 week ago

Extreme Stepmom Throat Training: Heavy Gagging, Atm, Huge Anal Toys, Sissification, Cbt And Golden Shower Finale! Cruel Bdsm Bbw Domme

Extreme Stepmom Throat Training: Heavy Gagging, Atm, Huge Anal Toys, Sissification, Cbt And Golden Shower Finale! Cruel Bdsm Bbw Domme

BDSMX 1 month ago

Admission of being a Sissy - Mean girls

Admission of being a Sissy - Mean girls

XHamster 3 years ago

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk! Arya Grander

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk! Arya Grander

XHamster 1 year ago

Electra Joness Party on Sep 1, 2026 - Part 3

HD 2:00 / 50:13

Electra Joness Party on Sep 1, 2026 - Part 3

Flirt4Free 4 days ago

hands free cum in cage with new toy

hands free cum in cage with new toy

Fetishpapa 1 month ago

Genitalia haircut & edging for chastity slave

Genitalia haircut & edging for chastity slave

XHamster 1 year ago

Femdom pegging with 8 inch strapon

Femdom pegging with 8 inch strapon

XHamster 10 months ago

Viuda Nagra Private Show

56% HD 2:00 / 9:51

Viuda Nagra Private Show

Flirt4Free 4 years ago

Headmistress ANAL SEXTOY MILKING and ORAL PLEASURE

Headmistress ANAL SEXTOY MILKING and ORAL PLEASURE

MatureTubeHere 3 years ago

Positive Femdom: Pegging, Fisting to Every Other, Pee. Arya Grander

Positive Femdom: Pegging, Fisting to Every Other, Pee. Arya Grander

Lesbian8 1 week ago

Oriental Angel with Latex Hard Sex in the Dungeon

Oriental Angel with Latex Hard Sex in the Dungeon

Amateur8 1 month ago

Brittney & Elvis Private Show

61% HD 2:00 / 6:22

Brittney & Elvis Private Show

Camster 3 years ago

This guy loves to be fucked by this machine

This guy loves to be fucked by this machine

Fapality 2 years ago

Nobody's Gonna Save You - Anal Bondage with a Dominant Mistress and Submissive Slave

Nobody's Gonna Save You - Anal Bondage with a Dominant Mistress and Submissive Slave

JuicyVid 2 weeks ago

PROSTATE ORGASM COMPILATION SISSY

PROSTATE ORGASM COMPILATION SISSY

XHamster 4 years ago

Sissy Slut BEGS for cock all night - Hardcore Femdom Pegging with Mistress Stellina Obscura

Sissy Slut BEGS for cock all night - Hardcore Femdom Pegging with Mistress Stellina Obscura

XHamster 1 year ago

Sissy Compilation Chastity Forever

Sissy Compilation Chastity Forever

Lesbian8 2 months ago

Anal Tease: JOI, Edging & Denial Adventures

Anal Tease: JOI, Edging & Denial Adventures

GiveMeAPorn 5 days ago

Manu Eyngri Private Show

HD 2:00 / 24:41

Manu Eyngri Private Show

Camster 3 weeks ago

What a way to cum - OMG

What a way to cum - OMG

Amateur8 1 year ago

Brea Rose Party on Apr 21, 2023

HD 2:00 / 50:00

Brea Rose Party on Apr 21, 2023

Camster 3 years ago

Brittney & Elvis Private Show

58% HD 2:00 / 6:22

Brittney & Elvis Private Show

Flirt4Free 3 years ago

Elizabeth Whiler Private Show

46% HD 2:00 / 6:55

Elizabeth Whiler Private Show

Camster 3 years ago

Alexis Amadahy And Jade Sissy Training And Strap On

Alexis Amadahy And Jade Sissy Training And Strap On

AbXXX 2 years ago

Electra Joness Party on Apr 13, 2026 - Part 3

51% 4K 2:00 / 1:00:15

Electra Joness Party on Apr 13, 2026 - Part 3

Flirt4Free 4 months ago

Gape For Goddess 2

HD 0:15 / 21:21

Gape For Goddess 2

IWantClips 4 years ago

Mistresst - High Class Sissy Trained

Mistresst - High Class Sissy Trained

InPorn 4 years ago

sissy training, I transform my husband into a real sissy. I fuck him and make him suck like a slut!

sissy training, I transform my husband into a real sissy. I fuck him and make him suck like a slut!

XHamster 2 years ago

Red Lips Tease and Pussyplay

61% 4K 2:00 / 10:06

Red Lips Tease and Pussyplay

Flirt4Free 3 years ago

Playing with My Husband's Asshole

Playing with My Husband's Asshole

XHamster 2 years ago

Dayla Smith Private Show

Dayla Smith Private Show

Flirt4Free 4 days ago

Male trainee in chastity humiliated with pegging and pissing

Male trainee in chastity humiliated with pegging and pissing

Yesvids 3 weeks ago

letshave a hot time - Part 2

58% HD 2:00 / 4:52

letshave a hot time - Part 2

Flirt4Free 5 months ago

Viky & Mateo Private Show

55% HD 2:00 / 11:13

Viky & Mateo Private Show

Flirt4Free 7 months ago

elf femboy in chastity belt gets tight ass stretched by bbc cock and fuck machine until cum

elf femboy in chastity belt gets tight ass stretched by bbc cock and fuck machine until cum

PornFreeNow 1 year ago

Hard pegging and massive cum from BBC ding-dong.

Hard pegging and massive cum from BBC ding-dong.

SortPorn 3 years ago

Sissy femboy makes chastity content and streams on chaturbate

Sissy femboy makes chastity content and streams on chaturbate

BigTitsLust 1 year ago

Sissy Slut School: Sissy Whore Trained to suck men's cocks and Take Deep Pegging Head Mistress Stellina Obscura

Sissy Slut School: Sissy Whore Trained to suck men's cocks and Take Deep Pegging Head Mistress Stellina Obscura

StiefMutter 2 weeks ago

Tori and Nina Are Couple of Baddies

55% HD 2:00 / 22:29

Tori and Nina Are Couple of Baddies

Camster 1 week ago

Bizarre Sissy Bad Dragon Gaping and FemDom Aperture Destruction with Speculum Show Off by Mastix Mercer

Bizarre Sissy Bad Dragon Gaping and FemDom Aperture Destruction with Speculum Show Off by Mastix Mercer

Amateur8 9 months ago

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk

XMilf 9 months ago

”Bi-Curious Bro Gets A Sissy Sandwich”

”Bi-Curious Bro Gets A Sissy Sandwich”

TransHero 8 months ago

PROSTATE EXPLOSION big compilation

PROSTATE EXPLOSION big compilation

XHamster 2 years ago

Viky & Mateo Private Show

56% HD 2:00 / 32:44

Viky & Mateo Private Show

Flirt4Free 7 months ago

Sissy Bitch Pegging Compilation. Femdom Chastity

Sissy Bitch Pegging Compilation. Femdom Chastity

BigTitsLust 2 years ago

Ava Maddison Private Show

63% 4K 2:00 / 29:24

Ava Maddison Private Show

Flirt4Free 6 months ago

Ariane Elisse Private Show

HD 2:00 / 11:10

Ariane Elisse Private Show

Camster 3 days ago

Labella Slays Dick on Crossdressing Big Dick Sissy

Labella Slays Dick on Crossdressing Big Dick Sissy

XHamster 4 months ago

Vends-ta-culotte - Anal training with your hot teacher who makes you her little slut

Vends-ta-culotte - Anal training with your hot teacher who makes you her little slut

XHamster 8 months ago

My owner becomes my SIssy

My owner becomes my SIssy

XHamster 2 years ago

Chelsea Roset Private Show

56% HD 2:00 / 26:30

Chelsea Roset Private Show

Flirt4Free 2 years ago

$let\'s have some fun - Part 2$ 4K 2:00 / 4:53

let\'s have some fun - Part 2

Camster 3 weeks ago

Encouraged BiSex - Pegging 7 mov

52% 0:05 / 2:28

Encouraged BiSex - Pegging 7 mov

Clips4sale 2 years ago

10 Anal Tasks CEI CBT Femdom Humiliation

64% HD 0:39 / 21:38

10 Anal Tasks CEI CBT Femdom Humiliation

FapHouse 2 months ago

Asian Mistress Dominafire Trains Her White Submissive Slave with Pegging

Asian Mistress Dominafire Trains Her White Submissive Slave with Pegging

FapHouse 5 days ago

Positive Femdom: Pegging, Fisting to Each Other, Pee. Arya Grander

Positive Femdom: Pegging, Fisting to Each Other, Pee. Arya Grander

PornFreeNow 1 week ago

Complete Sissy Transformation — Full Control with Domina Ava Savage & Mistress Damazonia

Complete Sissy Transformation — Full Control with Domina Ava Savage & Mistress Damazonia

Clips4sale 7 months ago

Bella Brookz Private Show

65% HD 2:00 / 18:34

Bella Brookz Private Show

Camster 3 years ago

Viky & Mateo Private Show

59% HD 2:00 / 4:48

Viky & Mateo Private Show

Camster 7 months ago

CARTOON Mistress Big Dick Blow Out -MOV

54% 0:55 / 7:45

CARTOON Mistress Big Dick Blow Out -MOV

Clips4sale 2 years ago

Sissy Training After First Time Feminization

Sissy Training After First Time Feminization

PornTop 2 years ago

Sissy Chastity Slave Boy Takes Huge Load in his Ass from Pegging

Sissy Chastity Slave Boy Takes Huge Load in his Ass from Pegging

Eporner 3 years ago

Andromeda Cute Private Show

66% HD 2:00 / 20:53

Andromeda Cute Private Show

Camster 4 weeks ago

How to bring a guy to a double orgasm

How to bring a guy to a double orgasm

XHamster 3 years ago

Asian Mistress Dominafire Trains Her White Submissive Slave with Pegging

Asian Mistress Dominafire Trains Her White Submissive Slave with Pegging

FapHouse 5 days ago

Amber Sweeett Private Show

HD 2:00 / 16:20

Amber Sweeett Private Show

Flirt4Free 3 days ago

Cum With Me! Sissy Sexuality Training & Mutual Orgasm Instructions with Goddess Kyaa - 720p MP4

4K 0:31 / 14:47

Cum With Me! Sissy Sexuality Training & Mutual Orgasm Instructions with Goddess Kyaa - 720p MP4

Clips4sale 2 years ago

We Love Spreading and Playing with Our Big Asses.

We Love Spreading and Playing with Our Big Asses.

XHamster 3 months ago

Extreme Anal Challenge - Strapon and 15-inch Dildo Until He Takes It All and Cums on My Black Nitrile Gloves

Extreme Anal Challenge - Strapon and 15-inch Dildo Until He Takes It All and Cums on My Black Nitrile Gloves

XHamster 2 weeks ago

Sissy femboy makes chastity content and streams on chaturbate

Sissy femboy makes chastity content and streams on chaturbate

SortPorn 1 year ago

alexis amadahy and jade sissy training and strap on

alexis amadahy and jade sissy training and strap on

PornOne 8 years ago

💥💋 THE BEST HOT MODEL LATINA EXOTIC TITS & PUSSY IN BIG DILDO TODAY HERE GUYS 💋 IM READY FOR GROUP SHOW GUYS ! ❤️❤️

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Camster 1 week ago

Your new Sexuality as A Sissy: EP5 Turning a Wanker into a Slave - Mistress Julia Femdom

Your new Sexuality as A Sissy: EP5 Turning a Wanker into a Slave - Mistress Julia Femdom

XHamster 2 years ago

Man Trains His Wife for Lesbian Sex #099 Full Video Long Pegging

Man Trains His Wife for Lesbian Sex #099 Full Video Long Pegging

XHamster 7 months ago

Positive Femdom: Pegging, Fisting to Every Other, Pee. Arya Grander

Positive Femdom: Pegging, Fisting to Every Other, Pee. Arya Grander

BigTitsLust 1 month ago

PERFECT MAID ANAL TRAINING

62% HD 0:30 / 18:28

PERFECT MAID ANAL TRAINING

Clips4sale 1 year ago

hands free cum in cage with fresh toy

hands free cum in cage with fresh toy

SortPorn 1 month ago

He's been asking for so long. I saw for the first time what a male anal orgasm is.

He's been asking for so long. I saw for the first time what a male anal orgasm is.

XHamster 4 years ago

Sunday Humiliation Part 3

HD 1:01 / 10:00

Sunday Humiliation Part 3

FapHouse 1 year ago

Elizabeth Whiler Private Show

56% HD 2:00 / 16:55

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

First Step for Virgin Sissy, Cunt Defloration. Anal Stretching, Facesitting, Humiliation, Pee. Mistress Arya Grander.

First Step for Virgin Sissy, Cunt Defloration. Anal Stretching, Facesitting, Humiliation, Pee. Mistress Arya Grander.

XHamster 1 year ago

JOI Echo in Latex with My Big Black Strapon - Luna Doll

JOI Echo in Latex with My Big Black Strapon - Luna Doll

XHamster 10 months ago

Her Mission Is to Take Him Deep with Her Siswet From Mrhankeystoys

Her Mission Is to Take Him Deep with Her Siswet From Mrhankeystoys

XHamster 4 weeks ago

Femdom Pegging Sissy Training, Strap on Anal for the New Recruit

Femdom Pegging Sissy Training, Strap on Anal for the New Recruit

XHamster 2 days ago

Extreme Pegging & Fisting Compilation - Femdom fucks male sub anal whore with Huge cock

Extreme Pegging & Fisting Compilation - Femdom fucks male sub anal whore with Huge cock

XHamster 1 year ago

Cruel BBW Goddess Destroys Stepson CBT Boots, Deep Gagging, Anal Stretching, Sissification and Piss Drinking!

Cruel BBW Goddess Destroys Stepson CBT Boots, Deep Gagging, Anal Stretching, Sissification and Piss Drinking!

XHamster 3 months ago

Sissy in varsity jacket spread wide for rough femdom anal training

Sissy in varsity jacket spread wide for rough femdom anal training

Yesvids 1 month ago

2032 - The BNWO Future you want

55% 0:30 / 15:01

2032 - The BNWO Future you want

Clips4sale 1 year ago

Pegging men is My pleasure

HD 0:39 / 18:32

Pegging men is My pleasure

Clips4sale 4 years ago

Katryn Anal Training n. 3 with Lady Sofia

Katryn Anal Training n. 3 with Lady Sofia

XHamster 2 weeks ago

Sissy Games : When my Cuckold Husband Meets my Lover - Maitresse Julia Femdom

Sissy Games : When my Cuckold Husband Meets my Lover - Maitresse Julia Femdom

XHamster 2 years ago

Whip and Fuck the Slut

67% HD 0:39 / 9:19

Whip and Fuck the Slut

FapHouse 2 years ago

Her Mission Is to Take Him Unfathomable with Her Siswet From Mrhankeystoys

Her Mission Is to Take Him Unfathomable with Her Siswet From Mrhankeystoys

Amateur8 3 weeks ago

Elizabeth Whiler Private Show

50% HD 2:00 / 9:53

Elizabeth Whiler Private Show

Camster 3 years ago

Junior & Brittney Private Show

Junior & Brittney Private Show

Camster 2 years ago

Not a woman, not a man, just a sissy bitch

60% HD 0:10 / 13:18

Not a woman, not a man, just a sissy bitch

LoyalFans 5 years ago

I Found Her Playing Video Games with Nothing on Underneath, and I Couldn't Resist Playing with Her Ass.

I Found Her Playing Video Games with Nothing on Underneath, and I Couldn't Resist Playing with Her Ass.

XHamster 1 week ago

Sexy Asian Mistress Dominates You

66% 0:39 / 11:30

Sexy Asian Mistress Dominates You

FapHouse 2 months ago

Elizabeth Whiler Private Show

50% HD 2:00 / 59:39

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

Uncensored Japanese Super Masochistic Female Slave Training Breeding SM X-Shaped Bondage Restraint Play Shame Play Blind

Uncensored Japanese Super Masochistic Female Slave Training Breeding SM X-Shaped Bondage Restraint Play Shame Play Blind

XHamster 3 years ago

$let\'s have some fun - Part 2$ 4K 2:00 / 4:52

let\'s have some fun - Part 2

Flirt4Free 4 weeks ago

His Chastity Locked While She Pegs Him Rough

His Chastity Locked While She Pegs Him Rough

AveXXX 1 month ago

Femdom Sissy Bitch Pegging and Oral sex Training

Femdom Sissy Bitch Pegging and Oral sex Training

SortPorn 2 days ago

Sissy Secretary: Feminization, Pegging, Fisting, & More Full-length (1080p)

Sissy Secretary: Feminization, Pegging, Fisting, & More Full-length (1080p)

XHamster 1 day ago

Wife Fucks Husband Like a Submissive Sissy Pegging Rimming #68 Part 1

Wife Fucks Husband Like a Submissive Sissy Pegging Rimming #68 Part 1

XHamster 2 years ago

Pegged in Chastity - Screw your Butt Anal Jerk off Instructions with Messy Talk by Female-Dominator Nikki Kit

Pegged in Chastity - Screw your Butt Anal Jerk off Instructions with Messy Talk by Female-Dominator Nikki Kit

BigTitsLust 4 years ago

Bella Brookz Private Show

63% HD 2:00 / 9:02

Bella Brookz Private Show

Camster 3 years ago

Top 10 Pegging Cumshots Vol.1

Top 10 Pegging Cumshots Vol.1

XHamster 10 months ago

Sexually excited Sissy Caption Story – Quarantined With Ebony Ally!

Sexually excited Sissy Caption Story – Quarantined With Ebony Ally!

SortPorn 1 year ago

Fist Fuck Training Sissy Sluts Ass

Fist Fuck Training Sissy Sluts Ass

BDSMX 4 years ago

EvilWoman: Anal destruction 3 Domme 1 Sissy

72% HD 0:22 / 10:24

EvilWoman: Anal destruction 3 Domme 1 Sissy

Clips4sale 1 year ago

Rubber Inhale Slut, turning our sissy maid into a gooning cum guzzler

65% 0:29 / 9:46

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Clips4sale 1 year ago

First sissy slut I pegged raw femdom strapon training

First sissy slut I pegged raw femdom strapon training

AveXXX 1 week ago

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