Sissy Anal Training (47,199)

The best and newest sissy anal training videos

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

48% HD 1:01 / 13:10

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

FapHouse 6 months ago

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

62% HD 1:01 / 5:10

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

FapHouse 10 months ago

Electra Joness Party on Mar 7, 2026 - Part 5

4K 2:00 / 1:02:30

Electra Joness Party on Mar 7, 2026 - Part 5

Flirt4Free 2 months ago

LADY SCARLET -A HARD SISSY TRAINING - PART 1 hd

HD 0:40 / 22:41

LADY SCARLET -A HARD SISSY TRAINING - PART 1 hd

Clips4sale 4 months ago

Sissy Trainer presents: I am a Woman

Sissy Trainer presents: I am a Woman

Eporner 6 years ago

Hotwife Date from the Cuckolds Point of View

Hotwife Date from the Cuckolds Point of View

xHamster 2 years ago

Viky & Mateo Private Show

59% HD 2:00 / 11:13

Viky & Mateo Private Show

Flirt4Free 4 months ago

Hot MILF with big tits fucks this fag's ass in his office with a huge strapon

Hot MILF with big tits fucks this fag's ass in his office with a huge strapon

Juicexxx 2 weeks ago

4 GIRLS 1 SLUT GANGBANG P2 4K

4K 0:25 / 11:23

4 GIRLS 1 SLUT GANGBANG P2 4K

Clips4sale 1 year ago

Nazanin Hunter Private Show

50% HD 2:00 / 8:05

Nazanin Hunter Private Show

Flirt4Free 2 years ago

Sabrina Velvet Private Show

53% HD 2:00 / 7:52

Sabrina Velvet Private Show

Flirt4Free 1 month ago

ANAL ONLY FROM NOW ON

ANAL ONLY FROM NOW ON

Bokep.PORN 1 month ago

Sissy anal whore gets deep throated, hardcore pegging, rough ass fucked, and anal fisting

Sissy anal whore gets deep throated, hardcore pegging, rough ass fucked, and anal fisting

Pornzona 1 month ago

Labella Slays Dick on Crossdressing Big Dick Sissy

Labella Slays Dick on Crossdressing Big Dick Sissy

xHamster 1 month ago

Bella Brookz Private Show

48% HD 2:00 / 12:38

Bella Brookz Private Show

Flirt4Free 3 years ago

Femboy glänzt hart peggen bis Sperma fließt Verifizierte Amateurin zerbricht ihn

Femboy glänzt hart peggen bis Sperma fließt Verifizierte Amateurin zerbricht ihn

DarkFetishTube 3 weeks 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

Bella Brookz Private Show

59% HD 2:00 / 20:02

Bella Brookz Private Show

Flirt4Free 2 years ago

Piss Enema Release and Fisting for Sissy Slut

55% HD 1:01 / 17:17

Piss Enema Release and Fisting for Sissy Slut

FapHouse 7 months ago

let me ride your hard dick i want to feel all u inside - Part 2

60% 4K 2:00 / 6:52

let me ride your hard dick i want to feel all u inside - Part 2

Flirt4Free 7 months ago

Monster Cock Stretching for my Trained FuckDoll with IRL Hentai Physics!

Monster Cock Stretching for my Trained FuckDoll with IRL Hentai Physics!

Pornzona 1 month 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 4 months ago

Bella Brookz Private Show

58% HD 2:00 / 4:39

Bella Brookz Private Show

Flirt4Free 3 years ago

early morning upskirt

early morning upskirt

SortPorn 10 months ago

GIGANTIC Ding-dong Pegging with Bad Dragon and Hankey for Lewd Sissy Wench by Mistresse Mercer

GIGANTIC Ding-dong Pegging with Bad Dragon and Hankey for Lewd Sissy Wench by Mistresse Mercer

Amateur8 6 months ago

Sissy Slut School (FULL): Cock Sucking Lessons, Anal Training, Femdom Pegging & Anal Fisting with Mistress Stellina Obscura

Premium HD 1:09:27

Sissy Slut School (FULL): Cock Sucking Lessons, Anal Training, Femdom Pegging & Anal Fisting with Mistress Stellina Obscura

Clips4sale 3 weeks ago

14 Days Long Anal Orgasm Sissy Calendar - Task

43% HD 1:01 / 18:13

14 Days Long Anal Orgasm Sissy Calendar - Task

FapHouse 1 year ago

Kevin Gets Used

Kevin Gets Used

Clips4sale 10 months ago

PROSTATE ORGASM COMPILATION SISSY

PROSTATE ORGASM COMPILATION SISSY

xHamster 4 years ago

Dominafire Pegging Latex Sissy

Dominafire Pegging Latex Sissy

xHamster 5 months ago

Leather Weather! The Best Leather

Leather Weather! The Best Leather

Some.Porn 1 year ago

My Bull Called, He Wants Us Both to Prepare Our Asses

50% HD 1:01 / 19:18

My Bull Called, He Wants Us Both to Prepare Our Asses

FapHouse 5 months ago

Transformation of a Sissy

Transformation of a Sissy

Pornzona 1 month ago

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

57% 0:39 / 25:09

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

FapHouse 7 months ago

SUBMISSIVE HUSBAND-Femdom Pegging

SUBMISSIVE HUSBAND-Femdom Pegging

Pornzona 3 days ago

feminized - femdom sissy training sex doll milked with fucking machine porn video

feminized - femdom sissy training sex doll milked with fucking machine porn video

BDSMShip 1 year ago

Mexican Independence Day cum Take My Mexican Dick - StrapOn

60% 0:40 / 15:03

Mexican Independence Day cum Take My Mexican Dick - StrapOn

Clips4sale 8 months ago

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

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

xHamster 11 months ago

Amy Roger Private Show

63% HD 2:00 / 4:16

Amy Roger Private Show

Flirt4Free 1 week 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 10 months ago

Scarleth Brownn Private Show

67% HD 2:00 / 8:59

Scarleth Brownn Private Show

Flirt4Free 3 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

Bella Brookz Private Show

57% HD 2:00 / 18:56

Bella Brookz Private Show

Flirt4Free 3 years ago

Breeding Cucky's Beautiful Wife III 4K HDR

49% 4K 0:22 / 12:02

Breeding Cucky's Beautiful Wife III 4K HDR

IWantClips 2 years ago

Bella Brookz Private Show

44% HD 2:00 / 14:02

Bella Brookz Private Show

Flirt4Free 3 years ago

Mistress Cuckholds Sissy Submissive Femdom Style

Mistress Cuckholds Sissy Submissive Femdom Style

Pornfact 2 months ago

Sexually Excited Sissy Caption Story – Quarantined With Ebony Ally!

Sexually Excited Sissy Caption Story – Quarantined With Ebony Ally!

Amateur8 3 years ago

Elizabeth Whiler Private Show

58% HD 2:00 / 6:03

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

Elizabeth Whiler Private Show

53% HD 2:00 / 8:01

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

Sweet & Daaniel Private Show

61% HD 2:00 / 6:47

Sweet & Daaniel Private Show

Flirt4Free 4 months ago

Horny Pegging Makes Him Cum Profusaly (MP4)

Horny Pegging Makes Him Cum Profusaly (MP4)

Clips4sale 2 years ago

Femdom Pegging Gangbang

69% HD 0:39 / 12:36

Femdom Pegging Gangbang

FapHouse 3 months ago

Viky & Mateo Private Show

54% HD 2:00 / 4:46

Viky & Mateo Private Show

Flirt4Free 4 months 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

Juicexxx 1 month ago

Genitalia haircut & edging for chastity slave

Genitalia haircut & edging for chastity slave

xHamster 1 year ago

Bella Brookz Private Show

50% HD 2:00 / 11:32

Bella Brookz Private Show

Flirt4Free 3 years ago

Bella Brookz Private Show

66% HD 2:00 / 7:26

Bella Brookz Private Show

Flirt4Free 3 years ago

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

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

xHamster 7 months ago

Femdom Sissy Anal Training: Cum in Your Cage CEI

49% HD 0:39 / 11:10

Femdom Sissy Anal Training: Cum in Your Cage CEI

FapHouse 2 months ago

Kandi More & Jamer Private Show

61% HD 2:00 / 56:41

Kandi More & Jamer Private Show

Flirt4Free 3 years ago

3 MONSTERS IN YOUR ASS ( Smartphone Version )

HD 0:51 / 17:24

3 MONSTERS IN YOUR ASS ( Smartphone Version )

Clips4sale 3 months ago

Bella Brookz Private Show

48% HD 2:00 / 9:32

Bella Brookz Private Show

Flirt4Free 2 years ago

Training my wife to anal. First anal stretching. Enema. Ep 24943

Training my wife to anal. First anal stretching. Enema. Ep 24943

xHamster 4 months ago

Lingerie Lover - Sissy Pegging POV

51% HD 1:01 / 15:30

Lingerie Lover - Sissy Pegging POV

FapHouse 1 year ago

Viky & Mateo Private Show

56% HD 2:00 / 32:44

Viky & Mateo Private Show

Flirt4Free 4 months ago

Mistress peggt ihre sissygfickte Schlampe bis geiler Prostataschlampen

Mistress peggt ihre sissygfickte Schlampe bis geiler Prostataschlampen

DarkFetishTube 1 month ago

Ares & Adara Private Show

46% HD 2:00 / 9:34

Ares & Adara Private Show

Flirt4Free 1 year ago

Harmoni Kalifornia's Sissy Husband Mr. B***e (Pip) Experiences Anal Training from Sean

Harmoni Kalifornia's Sissy Husband Mr. B***e (Pip) Experiences Anal Training from Sean

Dafreeporn 8 months ago

Stuffed Woman. the Hole Overflows as It Is Full to the Top

64% 0:39 / 11:41

Stuffed Woman. the Hole Overflows as It Is Full to the Top

FapHouse 4 months ago

Make me bi in chastity for your husband bbc please fuck my ass Queen

64% 0:30 / 19:37

Make me bi in chastity for your husband bbc please fuck my ass Queen

Clips4sale 1 year ago

Zoey Jones & Diego Valdezz Private Show

56% HD 2:00 / 13:11

Zoey Jones & Diego Valdezz Private Show

Flirt4Free 6 months ago

Brittney & Elvis Private Show

54% HD 2:00 / 6:22

Brittney & Elvis Private Show

Flirt4Free 2 years ago

Täglicher Femboy-Schwanz bricht in Güssen Amateure Pegging Femdom Domina

Täglicher Femboy-Schwanz bricht in Güssen Amateure Pegging Femdom Domina

DarkFetishTube 3 weeks ago

Dominate goddess in fishnets sits on sissy's face, clamps and teases his balls and denies orgasm

Dominate goddess in fishnets sits on sissy's face, clamps and teases his balls and denies orgasm

Pornzona 1 month ago

Sissies Obey In Trance

Sissies Obey In Trance

LoyalFans 2 years ago

Sissy Training - Une séance en couple avec ta psy

HD 0:27 / 20:10

Sissy Training - Une séance en couple avec ta psy

Clips4sale 3 years ago

Muslim Hijabi mistress wearing saree while he was locked in chastity Part 1

Muslim Hijabi mistress wearing saree while he was locked in chastity Part 1

xHamster 5 months ago

Turned into a sissy slut Part 2 - Pegging - 4K | Kiro Queen, JustALimeBoi

59% 4K 0:25 / 10:25

Turned into a sissy slut Part 2 - Pegging - 4K | Kiro Queen, JustALimeBoi

Clips4sale 4 months ago

Lick my pussy while he fucks your ass cuckold

Lick my pussy while he fucks your ass cuckold

XVideos 9 years ago

Femdom Pegging Latex Sissy by Dominafire

Femdom Pegging Latex Sissy by Dominafire

xHamster 1 year ago

Folding my bitch boi over and pegging his ass so hard and deep until his pathetic cock leaks cum

Folding my bitch boi over and pegging his ass so hard and deep until his pathetic cock leaks cum

xHamster 3 years ago

Wearing latex, anal training for my sissy slut, Preview

Wearing latex, anal training for my sissy slut, Preview

xHamster 4 years ago

Ariane Elisse Private Show

Ariane Elisse Private Show

Flirt4Free 3 days ago

Julie and Liza's Latex Doll

67% HD 0:10 / 19:56

Julie and Liza's Latex Doll

LoyalFans 3 months ago

Pupcup’s Next Lesson: Good Girls get their Holes Stuffed

49% HD 0:10 / 12:19

Pupcup’s Next Lesson: Good Girls get their Holes Stuffed

LoyalFans 6 months ago

Dildo Dolly 3

HD 0:10 / 13:30

LoyalFans 3 years ago

Preview: Lady Stefanie - This Is Cock Whore Gina - 1

Preview: Lady Stefanie - This Is Cock Whore Gina - 1

xHamster 4 years ago

HentaIRL - Femboy Deep Anal Session with 16 inch Tentacle - SD

HentaIRL - Femboy Deep Anal Session with 16 inch Tentacle - SD

Clips4sale 1 year ago

Femdom Pegging Gangbang

59% 0:39 / 11:17

Femdom Pegging Gangbang

FapHouse 3 months ago

Viky & Mateo Private Show

62% HD 2:00 / 19:22

Viky & Mateo Private Show

Flirt4Free 4 months ago

Femdom Humiliation, Sissy Training: Ready 4 Real Cock

Femdom Humiliation, Sissy Training: Ready 4 Real Cock

xHamster 4 weeks ago

JOI Echo With My Big Black Dick - Luna Doll

JOI Echo With My Big Black Dick - Luna Doll

xHamster 7 months ago

Femdom: Fisting, Deepthroat, Strap-on, Humiliation. Arya Grander

Femdom: Fisting, Deepthroat, Strap-on, Humiliation. Arya Grander

xHamster 5 months ago

Mean femdom Flagellation Treatment

Mean femdom Flagellation Treatment

Some.Porn 1 year ago

Arab sissy anal fuck in dubai middle east

Arab sissy anal fuck in dubai middle east

XVideosRed 3 years ago

Miracless edging game in flat micro chasity cage using magic wand Kiro Queen femboy sissy slut

Miracless edging game in flat micro chasity cage using magic wand Kiro Queen femboy sissy slut

Clips4sale 8 months ago

Sissy Kendall Anal Training & Slave Affirmations

53% HD 0:39 / 10:20

Sissy Kendall Anal Training & Slave Affirmations

FapHouse 2 months ago

JOI Cuck Anal Training CEI Next Level - Luna Doll

65% 0:39 / 15:22

JOI Cuck Anal Training CEI Next Level - Luna Doll

FapHouse 10 months ago

collection of sissification. anal fisting and hot strapon pegging.

61% HD 0:30 / 29:36

collection of sissification. anal fisting and hot strapon pegging.

PornBox 3 years ago

Dominatrix Mistress April and her wild twisted nymphs getting crazy

Dominatrix Mistress April and her wild twisted nymphs getting crazy

xHamster 1 year ago

Hailey Roses Private Show

Hailey Roses Private Show

Flirt4Free 2 years ago

Hailey Roses Private Show

56% HD 2:00 / 5:25

Hailey Roses Private Show

Flirt4Free 3 years ago

Hailey Roses Private Show

HD 2:00 / 21:08

Hailey Roses Private Show

Flirt4Free 3 years ago

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

62% 1:01 / 25:09

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

FapHouse 7 months ago

cum in chastity. step mommy footjob in stockings. your stuffed balls.

56% HD 0:23 / 7:40

cum in chastity. step mommy footjob in stockings. your stuffed balls.

PornBox 3 years ago

My Bull Called, He Wants Us Both to Prepare Our Asses

61% HD 0:39 / 19:18

My Bull Called, He Wants Us Both to Prepare Our Asses

FapHouse 5 months ago

Hole Training for Real Men, Deepthroat, Fingering, and Double Cock Fantasy

Hole Training for Real Men, Deepthroat, Fingering, and Double Cock Fantasy

xHamster 11 months ago

As We Continuously Explore Our Sexuality

HD 1:01 / 32:12

As We Continuously Explore Our Sexuality

FapHouse 1 year ago

Hailey Roses Private Show

61% HD 2:00 / 5:47

Hailey Roses Private Show

Flirt4Free 3 years ago

Elizabeth Whiler Private Show

51% HD 2:00 / 13:22

Elizabeth Whiler Private Show

Flirt4Free 3 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 10 months ago

Tess & Blaize ruin the sissy maid, taking it's slutty ass hole without mercy, ensuring that it remembers that they've been there for a long time!

Tess & Blaize ruin the sissy maid, taking it's slutty ass hole without mercy, ensuring that it remembers that they've been there for a long time!

Clips4sale 1 year ago

Femdom POV Sissy Training Pleasure Him

49% HD 0:39 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 2 months ago

JOI CEI Anal - Be My Best Sissy with Your Best Heels and Fuck Your Ass with a Dildo

HD 1:01 / 15:05

JOI CEI Anal - Be My Best Sissy with Your Best Heels and Fuck Your Ass with a Dildo

FapHouse 1 month ago

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

xHamster 4 months ago

JOI Cuck Anal Training CEI Next Level - Luna Doll

64% 1:01 / 15:22

JOI Cuck Anal Training CEI Next Level - Luna Doll

FapHouse 10 months ago

Viky & Mateo Private Show

62% HD 2:00 / 4:59

Viky & Mateo Private Show

Flirt4Free 4 months ago

Tatiana & Jack Private Show

HD 2:00 / 13:13

Tatiana & Jack Private Show

Flirt4Free 2 years ago

Femdom POV Sissy Training Pleasure Him

51% HD 1:01 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 2 months ago

Sarah Flower Private Show

63% HD 2:00 / 10:09

Sarah Flower Private Show

Flirt4Free 4 years ago

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