Sissy Anal Training (11,508)

The best and newest sissy anal training videos

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

49% HD 1:01 / 12:49

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

FapHouse 2 months ago

I fuck my husband on the beach

I fuck my husband on the beach

xHamster 1 year ago

Playing with My Husband's Asshole

Playing with My Husband's Asshole

xHamster 1 year ago

Strict Dominatrix in Spandex and her very absolutely virgin sissy that came for cunt defloration!

Strict Dominatrix in Spandex and her very absolutely virgin sissy that came for cunt defloration!

XVideos 1 year ago

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 4 years ago

Pegging and Fisting His Tight Asshole

Pegging and Fisting His Tight Asshole

xHamster 1 year 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 6 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 1 week ago

My husband has a new cock

My husband has a new cock

xHamster 1 year 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

Hotwife Date from the Cuckolds Point of View

Hotwife Date from the Cuckolds Point of View

xHamster 2 years ago

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

xHamster 2 weeks ago

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

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

FapHouse 4 days ago

Mistresst - High Class Sissy Trained

Mistresst - High Class Sissy Trained

InPorn 4 years ago

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

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

FapHouse 2 weeks ago

Happy Hour with Apologetic Domme - a short chastity love story

Happy Hour with Apologetic Domme - a short chastity love story

xHamster 2 years 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

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

65% 0:39 / 11:41

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

FapHouse 2 weeks ago

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

60% HD 0:39 / 5:10

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

FapHouse 6 months ago

Pegging and fisting my husband's asshole

Pegging and fisting my husband's asshole

xHamster 1 year ago

I lock my husband's cock in a chastity cage

I lock my husband's cock in a chastity cage

xHamster 1 year ago

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

66% 0:39 / 8:35

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

FapHouse 4 days ago

Mistress Olivia trains you little slut to be a sissy whore! German mistress with huge titsDirtytalk

Mistress Olivia trains you little slut to be a sissy whore! German mistress with huge titsDirtytalk

xHamster 2 weeks ago

Stepsister Fuck Stepbrother in Ass Very Big Strap on Dildo Vibrator Anal Pegging Femdom Spanking

76% HD 1:01 / 7:58

Stepsister Fuck Stepbrother in Ass Very Big Strap on Dildo Vibrator Anal Pegging Femdom Spanking

FapHouse 1 year 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

Sissy Mesmerize Sessions

59% HD 0:10 / 16:20

Sissy Mesmerize Sessions

LoyalFans 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 1 month 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 6 months ago

Dominatrix Strap-On Dildo Sissy

Dominatrix Strap-On Dildo Sissy

xHamster 2 years ago

Headmistress ANAL SEXTOY MILKING and ORAL PLEASURE

Headmistress ANAL SEXTOY MILKING and ORAL PLEASURE

MatureTubeHere 3 years ago

Compilation of tied up man getting fisted and pegged

Compilation of tied up man getting fisted and pegged

XGroovy 1 year ago

Sissy Anal JOI

52% HD 1:01 / 7:41

FapHouse 2 years 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 3 months ago

Helena Red Private Show

68% HD 2:00 / 10:43

Helena Red Private Show

Flirt4Free 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

BDSMX 1 month ago

Ares & Adara Private Show

47% HD 2:00 / 20:07

Ares & Adara Private Show

Flirt4Free 1 year ago

I wanna destroy your boi cunt like this - check out my links for full clip

I wanna destroy your boi cunt like this - check out my links for full clip

FreePorn8 3 weeks ago

Chelsea Roset Private Show

64% HD 2:00 / 26:30

Chelsea Roset Private Show

Flirt4Free 2 years ago

Viuda Nagra Private Show

60% HD 2:00 / 29:45

Viuda Nagra Private Show

Flirt4Free 2 years ago

Do You Like Double Penetration?

52% HD 2:00 / 12:31

Do You Like Double Penetration?

Flirt4Free 2 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 7 months ago

superlatively good ebony knobs ever comp

superlatively good ebony knobs ever comp

SortPorn 1 year ago

Ava Maddison Private Show

Ava Maddison Private Show

Flirt4Free 16 hours ago

Hot MILF Femdom Wife Exposes Her Husband as ANAL SISSY SLUT Featuring Mistress Stellina Obscura

Hot MILF Femdom Wife Exposes Her Husband as ANAL SISSY SLUT Featuring Mistress Stellina Obscura

xHamster 9 months 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 3 years ago

Training Zero Pegging His Sissy Hole! Anal Hard Fucking Strapon BDSM Prostate Bondage Slave Real Homemade Orgasm Cum Milf

Training Zero Pegging His Sissy Hole! Anal Hard Fucking Strapon BDSM Prostate Bondage Slave Real Homemade Orgasm Cum Milf

xHamster 1 year ago

Sarah Flower Private Show

64% HD 2:00 / 14:40

Sarah Flower Private Show

Flirt4Free 3 years ago

Kinky Stepmom Wants to Anal Fuck Her Stepson in His Asshole

65% 0:39 / 4:53

Kinky Stepmom Wants to Anal Fuck Her Stepson in His Asshole

FapHouse 1 year ago

Charlotte Texas Party on Jan 12, 2026

4K 2:00 / 28:23

Charlotte Texas Party on Jan 12, 2026

Flirt4Free 1 month ago

Mafe Flex & Sebastiaan Private Show

Mafe Flex & Sebastiaan Private Show

Flirt4Free 1 month ago

Kandi More & Jamer Private Show

69% HD 2:00 / 5:23

Kandi More & Jamer Private Show

Flirt4Free 2 years ago

Sissy spouse dominated by sexy wifey

Sissy spouse dominated by sexy wifey

Amateur8 2 years ago

The Visit - Part 4 Gameplay by LoveSkySan69

The Visit - Part 4 Gameplay by LoveSkySan69

xHamster 1 year ago

SISSY TRAINING

61% HD 0:10 / 22:10

LoyalFans 4 years ago

How Would I Date My Femboy/sissy?

66% HD 0:39 / 9:32

How Would I Date My Femboy/sissy?

FapHouse 4 months ago

Chubby naked girl dominates his cock and balls - Ball stretching while sissy training

Chubby naked girl dominates his cock and balls - Ball stretching while sissy training

xHamster 2 years ago

Two Sissies Love to Suck Mistress's Strap-on and Love to Be Used!

Two Sissies Love to Suck Mistress's Strap-on and Love to Be Used!

xHamster 1 year ago

How To Masturbate Like A Girl

HD 0:10 / 17:39

How To Masturbate Like A Girl

LoyalFans 11 months ago

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

65% 1:01 / 43:05

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

FapHouse 1 year ago

Betty Sandra Private Show

65% HD 2:00 / 7:08

Betty Sandra Private Show

Flirt4Free 4 years ago

Cristal Colin Party on Jun 21, 2022

59% HD 2:00 / 25:17

Cristal Colin Party on Jun 21, 2022

Flirt4Free 3 years ago

Dirty Mistress Can't Stop Gaping His Sissy Ass!

Dirty Mistress Can't Stop Gaping His Sissy Ass!

xHamster 2 years ago

Ares & Adara Private Show

53% HD 2:00 / 9:20

Ares & Adara Private Show

Flirt4Free 1 year ago

Sofi Saenz Private Show

66% HD 2:00 / 8:23

Sofi Saenz Private Show

Flirt4Free 5 months ago

Lingerie Lover - Sissy Pegging POV

55% HD 0:39 / 15:30

Lingerie Lover - Sissy Pegging POV

FapHouse 11 months ago

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

44% HD 0:39 / 12:49

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

FapHouse 2 months ago

Two Mistress's and a Sissy Whore

Two Mistress's and a Sissy Whore

xHamster 1 year ago

French Amateur Mom Humiliates Her Small Dick Stepson

French Amateur Mom Humiliates Her Small Dick Stepson

xHamster 2 years ago

Сruel stepmom stretches stepson&#039_s anus, ballbusting, roughly humiliates, pisses, orders him to lick her wet pussy.

Сruel stepmom stretches stepson&#039_s anus, ballbusting, roughly humiliates, pisses, orders him to lick her wet pussy.

XVideos 7 months ago

Sissy Feminization, Anal Training, CEI Cum Eating Instruction (Arya Grander) - FemDom POV Domination

Sissy Feminization, Anal Training, CEI Cum Eating Instruction (Arya Grander) - FemDom POV Domination

TheyAreHuge 3 years ago

Deep Strap-on Bang: Sexy Pegging For Sissy Slut. StepMom and her StepSon

Deep Strap-on Bang: Sexy Pegging For Sissy Slut. StepMom and her StepSon

Dafreeporn 1 month ago

Monthly Curse: Clit Tease, Electro, Ruined Orgasm

63% HD 1:01 / 22:13

Monthly Curse: Clit Tease, Electro, Ruined Orgasm

FapHouse 9 months ago

Viuda Nagra Private Show

48% HD 2:00 / 9:57

Viuda Nagra Private Show

Flirt4Free 3 years ago

Two Sissies Love to Suck Mistress's Strap-on and Love to Be Used!

56% HD 1:01 / 13:27

Two Sissies Love to Suck Mistress's Strap-on and Love to Be Used!

FapHouse 1 year ago

Your Manhood Removed - Mistress Kendra wmv

57% 0:11 / 10:15

Your Manhood Removed - Mistress Kendra wmv

Clips4sale 3 years ago

Anal Training, Learning

Anal Training, Learning

xHamster 4 weeks ago

Sissy Husband BBC Training Part 3/3: Femdom Sissy Fucking with Double BBC Pegging & Anal **** with Stellina Obscura

HD 0:10 / 10:43

Sissy Husband BBC Training Part 3/3: Femdom Sissy Fucking with Double BBC Pegging & Anal **** with Stellina Obscura

LoyalFans 9 months ago

I destroy my husband's ass

I destroy my husband's ass

xHamster 2 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 Cuck Anal Training CEI Next Level - Luna Doll

JOI Cuck Anal Training CEI Next Level - Luna Doll

xHamster 7 months ago

Monthly Curse: Clit Tease, Electro, Ruined Orgasm

Monthly Curse: Clit Tease, Electro, Ruined Orgasm

xHamster 9 months ago

My Mistress is stretching me out!

My Mistress is stretching me out!

xHamster 1 month ago

Betty Sandra Private Show

65% HD 2:00 / 5:04

Betty Sandra Private Show

Flirt4Free 2 years ago

Zara Rousse Private Show

Zara Rousse Private Show

Flirt4Free 1 week ago

Dominatrix Mistress April and her wild twisted nymphs getting crazy

Dominatrix Mistress April and her wild twisted nymphs getting crazy

xHamster 10 months ago

Zara Rousse Private Show

HD 2:00 / 12:24

Zara Rousse Private Show

Flirt4Free 1 week ago

French Amateur Stepmom Humiliates Her Small Dick Stepson

French Amateur Stepmom Humiliates Her Small Dick Stepson

FapHouse 1 year ago

Bondage Show

54% HD 2:00 / 36:00

Flirt4Free 1 year ago

Sissy Husband Double BBC Training (FULL): Humiliating Wedgies, Panties, Spankings, Double Anal Pegging & **** with Mistress Stellina Obscura

60% HD 0:10 / 41:20

Sissy Husband Double BBC Training (FULL): Humiliating Wedgies, Panties, Spankings, Double Anal Pegging & **** with Mistress Stellina Obscura

LoyalFans 9 months ago

Tali Majid Private Show

HD 2:00 / 21:47

Tali Majid Private Show

Flirt4Free 1 day ago

Extraordinary Pegging & Fisting Compilation - Femdom screws boy sub anal bitch with Massive shlong

Extraordinary Pegging & Fisting Compilation - Femdom screws boy sub anal bitch with Massive shlong

BigTitsLust 1 year ago

Betty Sandra Private Show

61% 4K 2:00 / 9:13

Betty Sandra Private Show

Flirt4Free 2 years ago

Gaby Whitee Private Show

HD 2:00 / 18:31

Gaby Whitee Private Show

Flirt4Free 3 years ago

Bossy female makes her hubby cum from behind - Home video

Bossy female makes her hubby cum from behind - Home video

AnySex 1 year ago

Naty Desiree & Evelyn Evy Private Show

Naty Desiree & Evelyn Evy Private Show

Flirt4Free 10 hours ago

Betty Sandra Private Show

68% HD 2:00 / 11:20

Betty Sandra Private Show

Flirt4Free 4 years ago

Joi cei sissy anal training

Joi cei sissy anal training

xHamster 7 months ago

Eating Vagina and Femdom Pegging, Gagging Reflex. Curvy StepMom Mistresse Sissy Training.

Eating Vagina and Femdom Pegging, Gagging Reflex. Curvy StepMom Mistresse Sissy Training.

PornFreeNow 1 month ago

FEMALE-DOM PEGGING CHASTITY FAGGOT

FEMALE-DOM PEGGING CHASTITY FAGGOT

SortPorn 3 years ago

Betty Sandra Private Show

68% HD 2:00 / 4:22

Betty Sandra Private Show

Flirt4Free 2 years ago

Mafe Flex & Sebastiaan Private Show

58% 4K 2:00 / 7:01

Mafe Flex & Sebastiaan Private Show

Flirt4Free 4 weeks ago

Sofi Saenz Private Show

Sofi Saenz Private Show

Flirt4Free 4 months ago

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XVideosRed 3 years ago

Betty Sandra Private Show

70% HD 2:00 / 4:04

Betty Sandra Private Show

Flirt4Free 4 years ago

Mafe Flex & Sebastiaan Private Show

Mafe Flex & Sebastiaan Private Show

Flirt4Free 2 weeks ago

Pee Humiliation, Femdom Blowjob, Stretching Anal, Pegging Strap-on, Eating Cum. Stepmom Arya Grander and Her Sissy Training

Pee Humiliation, Femdom Blowjob, Stretching Anal, Pegging Strap-on, Eating Cum. Stepmom Arya Grander and Her Sissy Training

xHamster 1 year ago

Training Zero Femdom Sissy Anal Pegging Huge Strapon Chastity Slave Bondage BDSM Real Homemade Amateur Couple Wife MILF FLR

Training Zero Femdom Sissy Anal Pegging Huge Strapon Chastity Slave Bondage BDSM Real Homemade Amateur Couple Wife MILF FLR

xHamster 11 months ago

Camila Prieto Private Show

Camila Prieto Private Show

Flirt4Free 1 week ago

Ares & Adara Private Show

61% HD 2:00 / 10:31

Ares & Adara Private Show

Flirt4Free 1 year ago

Betty Sandra Private Show

67% HD 2:00 / 14:16

Betty Sandra Private Show

Flirt4Free 4 years ago

Tita Madurita Private Show

HD 2:00 / 31:19

Tita Madurita Private Show

Flirt4Free 2 years ago

Mafe Flex & Sebastiaan Private Show

Mafe Flex & Sebastiaan Private Show

Flirt4Free 1 week ago

Sissy Wife Date Night Anal JOI - Clara Dee JOI

44% HD 1:01 / 11:47

Sissy Wife Date Night Anal JOI - Clara Dee JOI

FapHouse 9 months ago

Zara Rousse Private Show

HD 2:00 / 27:17

Zara Rousse Private Show

Flirt4Free 1 week ago

poked from behind and in front

poked from behind and in front

Clips4sale 2 years ago

Kandi More & Jamer Private Show

Kandi More & Jamer Private Show

Flirt4Free 2 years ago

Betty Sandra Private Show

Betty Sandra Private Show

Flirt4Free 2 years ago

Sofi Saenz Private Show

56% 4K 2:00 / 5:50

Sofi Saenz Private Show

Flirt4Free 4 months ago

Zara Rousse Private Show

4K 2:00 / 13:50

Zara Rousse Private Show

Flirt4Free 2 weeks ago

Mafe Flex & Sebastiaan Private Show

Mafe Flex & Sebastiaan Private Show

Flirt4Free 6 days ago

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