Sissy Anal Training (25,162)

The best and newest sissy anal training videos

Reven Mayers Private Show

Reven Mayers Private Show

Flirt4Free 1 week ago

Sexy Wife with Big Strapon pegging her Husband with Handjob

Sexy Wife with Big Strapon pegging her Husband with Handjob

XHamster 1 year ago

Playing with My Husband's Asshole

Playing with My Husband's Asshole

XHamster 2 years ago

Sissy Whore Deep Throats Huge Pegging Fetish Sissy Slut

Sissy Whore Deep Throats Huge Pegging Fetish Sissy Slut

AveXXX 5 days ago

Anal training n. three - Miss Katryn dominated and pegged by Lady Sofia femdom headmistress

Anal training n. three - Miss Katryn dominated and pegged by Lady Sofia femdom headmistress

SortPorn 1 week ago

Katryn Anal Training n. 3 with Lady Sofia

Katryn Anal Training n. 3 with Lady Sofia

XHamster 3 weeks ago

Manu Eyngri Private Show

Manu Eyngri Private Show

Flirt4Free 1 week ago

Coralyn Jewel Private Show

57% HD 2:00 / 10:00

Coralyn Jewel Private Show

Flirt4Free 3 years ago

Manu Eyngri Private Show

Manu Eyngri Private Show

Camster 1 week ago

Play with My Sensual Body and Make My Squirt So Hard(fire)

Play with My Sensual Body and Make My Squirt So Hard(fire)

Flirt4Free 4 years ago

Size Queen Sissy Boy Training with CEI

55% HD 0:39 / 20:55

Size Queen Sissy Boy Training with CEI

FapHouse 2 months ago

Femdom POV Sissy Training Pleasure Him

48% HD 0:39 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 5 months ago

Headmistress ANAL SEXTOY MILKING and ORAL PLEASURE

Headmistress ANAL SEXTOY MILKING and ORAL PLEASURE

MatureTubeHere 3 years ago

Sissy Chanel Gets Anal Fucked with the Fucking Machine Hardcore

Sissy Chanel Gets Anal Fucked with the Fucking Machine Hardcore

XHamster 3 weeks 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

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 4 weeks ago

989 Perverted Stepdaddy, Panty Sniffer Turned Into Sissy Slut - CEI, Ruined Orgasm, Step-daughter in a College Outfit

55% HD 1:01 / 10:37

989 Perverted Stepdaddy, Panty Sniffer Turned Into Sissy Slut - CEI, Ruined Orgasm, Step-daughter in a College Outfit

FapHouse 1 year ago

Hotwife Date from the Cuckolds Point of View

Hotwife Date from the Cuckolds Point of View

XHamster 2 years ago

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

68% HD 1:01 / 47:50

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

FapHouse 1 week ago

Viuda Nagra Private Show

66% HD 2:00 / 9:57

Viuda Nagra Private Show

Camster 4 years ago

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

72% HD 0:39 / 47:50

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

FapHouse 1 week ago

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 4 years ago

Ava Maddison Private Show

59% 4K 2:00 / 29:24

Ava Maddison Private Show

Flirt4Free 6 months ago

Come on, Honey. I'll Fuck Your Ass. Stepmom Testing Stepsons Anal Hole.

62% 0:39 / 8:35

Come on, Honey. I'll Fuck Your Ass. Stepmom Testing Stepsons Anal Hole.

FapHouse 7 months ago

Miss Sally Pegs Her Good Little Sissy

HD 0:39 / 18:22

Miss Sally Pegs Her Good Little Sissy

FapHouse 1 week ago

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

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

XHamster 1 week ago

Miss Sally Pegs Her Good Little Sissy

63% HD 1:01 / 18:22

Miss Sally Pegs Her Good Little Sissy

FapHouse 1 week ago

FEMDOM SISSY PEGGING ANAL CUM EATING BIG TITS STRAPON CUMSHOT

FEMDOM SISSY PEGGING ANAL CUM EATING BIG TITS STRAPON CUMSHOT

XHamster 7 months ago

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

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

XHamster 7 months ago

Mistresst - High Class Sissy Trained

Mistresst - High Class Sissy Trained

InPorn 4 years ago

Sissy Academy Part 5 - Sissy's Anal Adventure

HD 0:39 / 26:58

Sissy Academy Part 5 - Sissy's Anal Adventure

FapHouse 3 months ago

Ares & Adara Private Show

47% HD 2:00 / 20:07

Ares & Adara Private Show

Flirt4Free 1 year ago

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

XHamster 7 months 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 3 weeks ago

Sex Doll Has Arrived

HD 0:39 / 32:44

Sex Doll Has Arrived

FapHouse 1 year ago

Femdom POV Sissy Training Pleasure Him

46% HD 1:01 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 5 months ago

Sissy feminization, anal training, CEI cum eating instruction (Arya Grander) - FemDom

Sissy feminization, anal training, CEI cum eating instruction (Arya Grander) - FemDom

XHamster 3 weeks 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 2 years ago

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

68% 0:39 / 11:41

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

FapHouse 7 months ago

JOI for Anal CEI Ashley Sinclair

57% HD 1:01 / 7:03

JOI for Anal CEI Ashley Sinclair

FapHouse 4 months ago

Happy Hour with Apologetic Domme - a short chastity love story

Happy Hour with Apologetic Domme - a short chastity love story

XHamster 3 years ago

Lazy wife take a nap, but he wakes her up with a dick in her ass

Lazy wife take a nap, but he wakes her up with a dick in her ass

XHamster 1 month ago

femdom Bday gift PART 1

femdom Bday gift PART 1

XHamster 4 days ago

Sissy Club Slut Huge Strap-on and Deep Fisting Full Length 50 Minutes (1080p)

64% HD 1:01 / 53:41

Sissy Club Slut Huge Strap-on and Deep Fisting Full Length 50 Minutes (1080p)

FapHouse 2 weeks ago

Sissy Gamer Gurl: Feminization & Throat Fucking Part 1 of 3 (1080p)

65% HD 0:39 / 17:26

Sissy Gamer Gurl: Feminization & Throat Fucking Part 1 of 3 (1080p)

FapHouse 1 week 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 1 month ago

April Benson Private Show

53% HD 2:00 / 14:52

April Benson Private Show

Flirt4Free 2 years ago

Sissy Chanel Gets Anal Fucked with the Fucking Machine / Hardcore

65% HD 1:01 / 6:45

Sissy Chanel Gets Anal Fucked with the Fucking Machine / Hardcore

FapHouse 3 weeks ago

Femdom Strict Sissy Training Session: Cock Sucking, CBT, Pegging & Fisting with Mistress Stellina (1080p)

HD 0:39 / 54:59

Femdom Strict Sissy Training Session: Cock Sucking, CBT, Pegging & Fisting with Mistress Stellina (1080p)

FapHouse 1 week ago

Betty Sandra Private Show

55% HD 2:00 / 7:26

Betty Sandra Private Show

Flirt4Free 3 years ago

Ares & Adara Private Show

61% HD 2:00 / 20:07

Ares & Adara Private Show

Camster 1 year ago

Toilet Anal Fuck in the Bathroom for My Sissy Bitch Tiffany

Toilet Anal Fuck in the Bathroom for My Sissy Bitch Tiffany

XHamster 3 months ago

Viuda Nagra Private Show

48% HD 2:00 / 9:57

Viuda Nagra Private Show

Flirt4Free 4 years ago

Mistress April enforces sissy training with pegging and punishment on her male submissive

Mistress April enforces sissy training with pegging and punishment on her male submissive

Yesvids 3 weeks 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

Helena Red Private Show

64% HD 2:00 / 10:43

Helena Red Private Show

Flirt4Free 3 years ago

Milked & Bred Mistress Stellina Obscura Humiliates Husband with Sissy Hucow Transformation, Milking, Pegging & Toilet Play 108

HD 0:39 / 1:01:33

Milked & Bred Mistress Stellina Obscura Humiliates Husband with Sissy Hucow Transformation, Milking, Pegging & Toilet Play 108

FapHouse 2 days 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

Itsrealamateurs 4 weeks ago

Dominatrix Strap-On Dildo Sissy

Dominatrix Strap-On Dildo Sissy

XHamster 2 years ago

Miss Sally Pegs Her Fine Little Sissy

Miss Sally Pegs Her Fine Little Sissy

Amateur8 3 days ago

Pegging and fisting my husband's asshole

Pegging and fisting my husband's asshole

XHamster 2 years ago

Tori Mcqueen & Nina Lovez Private Show

HD 2:00 / 18:17

Tori Mcqueen & Nina Lovez Private Show

Camster 4 days ago

Charlotte Flexes Naked

68% HD 2:00 / 3:51

Charlotte Flexes Naked

Flirt4Free 9 years ago

Sissy Compilation Chastity Forever

Sissy Compilation Chastity Forever

Lesbian8 3 months ago

Size Queen Sissy Boy Training with CEI

Size Queen Sissy Boy Training with CEI

XHamster 1 month ago

Miss Sally Pegs Her Good Little Sissy

Miss Sally Pegs Her Good Little Sissy

XHamster 3 days ago

Viuda Nagra Private Show

59% HD 2:00 / 29:45

Viuda Nagra Private Show

Flirt4Free 3 years ago

Whored Out Office Sissy - Pegging POV with Elle Eros

66% HD 0:39 / 8:17

Whored Out Office Sissy - Pegging POV with Elle Eros

FapHouse 1 year ago

Reven Mayers Private Show

Reven Mayers Private Show

Flirt4Free 1 week ago

Size Queen Sissy Boy Training with CEI

Size Queen Sissy Boy Training with CEI

XHamster 2 months ago

Chelsea Roset Private Show

56% HD 2:00 / 26:30

Chelsea Roset Private Show

Flirt4Free 2 years 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 2 months ago

Amateur thong-on movie scene – Amateur belt-on movie – Real wife bangs in good pegging her pliant hooby using a large toy, This babe makes greetings like a sissy slut. Escouple 08-26

Amateur thong-on movie scene – Amateur belt-on movie – Real wife bangs in good pegging her pliant hooby using a large toy, This babe makes greetings like a sissy slut. Escouple 08-26

SortPorn 2 weeks ago

Sunday Humiliation Part 3

HD 1:01 / 10:00

Sunday Humiliation Part 3

FapHouse 1 year ago

Ares & Adara Private Show

60% HD 2:00 / 6:43

Ares & Adara Private Show

Camster 1 year ago

Femdom Strict Sissy Training Session: Cock Sucking, CBT, Pegging & Fisting with Mistress Stellina (1080p)

HD 1:01 / 54:59

Femdom Strict Sissy Training Session: Cock Sucking, CBT, Pegging & Fisting with Mistress Stellina (1080p)

FapHouse 1 week ago

Depth Training My Boytoy's Ass With A 46 Inch Depth Trainer Dildo

Depth Training My Boytoy's Ass With A 46 Inch Depth Trainer Dildo

XHamster 4 years ago

Leather Weather! The Best Leather

Leather Weather! The Best Leather

Some.Porn 1 year ago

It's my birthday, she gave me full package...all holes in one day

It's my birthday, she gave me full package...all holes in one day

FapHouse 1 month ago

Mandy Lov Private Show

4K 2:00 / 10:58

Mandy Lov Private Show

Camster 2 weeks ago

Sharon J Private Show

HD 2:00 / 11:27

Sharon J Private Show

Camster 1 week ago

Gaby Whitee Private Show

HD 2:00 / 1:02:00

Gaby Whitee Private Show

Flirt4Free 4 years ago

Viuda Nagra Private Show

HD 2:00 / 21:17

Viuda Nagra Private Show

Camster 3 years ago

Betty Sandra Private Show

63% 4K 2:00 / 4:50

Betty Sandra Private Show

Flirt4Free 2 years ago

Femdom Pegging Sissy Training, Thong on Anal for the Fresh Recruit

Femdom Pegging Sissy Training, Thong on Anal for the Fresh Recruit

SortPorn 1 week ago

Ares & Adara Private Show

51% HD 2:00 / 9:34

Ares & Adara Private Show

Flirt4Free 1 year ago

Sharon J Private Show

Sharon J Private Show

Flirt4Free 2 weeks ago

Punished Sissy Husband Part 4 of 4: Anal Fisting & Cum Eating with Mistress Stellina Obscura

HD 0:25 / 12:44

Punished Sissy Husband Part 4 of 4: Anal Fisting & Cum Eating with Mistress Stellina Obscura

Clips4sale 1 week ago

The Very First Pegging Experience

66% HD 0:39 / 6:04

The Very First Pegging Experience

FapHouse 1 week ago

Betty Sandra Private Show

64% HD 2:00 / 14:37

Betty Sandra Private Show

Camster 5 years ago

Dominant MILF makes her obedient stepson scream in orgasm with her fists

Dominant MILF makes her obedient stepson scream in orgasm with her fists

XGroovy 1 year ago

Vends-ta-culotte - Gorgeous luscious French brunette gives you a good lesson of anal training

Vends-ta-culotte - Gorgeous luscious French brunette gives you a good lesson of anal training

XHamster 6 months ago

Sissy See - Sissy Do (joi Game with Elle Eros )

Sissy See - Sissy Do (joi Game with Elle Eros )

FapHouse 2 years ago

Tita Madurita Private Show

68% HD 2:00 / 4:20

Tita Madurita Private Show

Camster 3 years ago

Blonde Mistress Training

Blonde Mistress Training

AveXXX 3 weeks ago

Reven Mayers Private Show

Reven Mayers Private Show

Flirt4Free 3 days ago

Sissy Anal JOI

64% HD 0:39 / 7:41

FapHouse 2 years ago

Argentinian nurse trains sissy boyfriend with inflatable anal plug

Argentinian nurse trains sissy boyfriend with inflatable anal plug

Yesvids 1 month ago

Size Queen Sissy Boy Training with CEI

69% HD 1:01 / 20:55

Size Queen Sissy Boy Training with CEI

FapHouse 2 months ago

Sissy feminization, anal training, CEI cum eating instruction (Arya Grander) - FemDom

Sissy feminization, anal training, CEI cum eating instruction (Arya Grander) - FemDom

FapHouse 2 weeks ago

Evelyn Ezra Private Show

63% HD 2:00 / 4:15

Evelyn Ezra Private Show

Flirt4Free 3 years ago

Step Mom and Your School Bully

66% 4K 2:00 / 24:45

Step Mom and Your School Bully

Camster 1 year ago

Sissy Training Session with Young Partner in a Threesome Adventure

Sissy Training Session with Young Partner in a Threesome Adventure

JuicyVid 3 weeks ago

Manu Eyngri Private Show

HD 2:00 / 24:41

Manu Eyngri Private Show

Camster 1 month ago

Rubber Sissy: Anal & Oral Training

Rubber Sissy: Anal & Oral Training

FapHouse 3 weeks ago

Reven Mayers Private Show

Reven Mayers Private Show

Camster 1 week ago

Reven Mayers Private Show

HD 2:00 / 15:08

Reven Mayers Private Show

Flirt4Free 6 days ago

Kandi More & Jamer Private Show

61% HD 2:00 / 56:41

Kandi More & Jamer Private Show

Camster 3 years ago

Sexy Asian Mistress Dominates You

66% 0:39 / 11:30

Sexy Asian Mistress Dominates You

FapHouse 2 months ago

Coralyn Jewel Private Show

57% HD 2:00 / 4:33

Coralyn Jewel Private Show

Camster 3 years ago

Anal Training, Learning

Anal Training, Learning

XHamster 7 months ago

Tori Mcqueen & Nina Lovez Private Show

Tori Mcqueen & Nina Lovez Private Show

Flirt4Free 2 days 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

BDSMX 8 months ago

BBW Femdom - Pegging Chaste Sissy Anal

BBW Femdom - Pegging Chaste Sissy Anal

XHamster 2 years ago

Mandy Lov Private Show

Mandy Lov Private Show

Flirt4Free 3 days ago

Compilation of tied up man getting fisted and pegged

Compilation of tied up man getting fisted and pegged

XGroovy 1 year ago

Femdom Pegging Sissy Training, Belt on Anal for the Fresh Recruit

Femdom Pegging Sissy Training, Belt on Anal for the Fresh Recruit

BigTitsLust 1 week ago

Tori Mcqueen & Nina Lovez Private Show

Tori Mcqueen & Nina Lovez Private Show

Flirt4Free 5 days ago

Lazy Wife Take a Nap, but He Wakes Her up with a Dick in Her Ass

60% HD 0:39 / 9:43

Lazy Wife Take a Nap, but He Wakes Her up with a Dick in Her Ass

FapHouse 1 month ago

Kandi More & Jamer Private Show

57% HD 2:00 / 5:32

Kandi More & Jamer Private Show

Flirt4Free 3 years ago

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