Sissy Training (154 593)

Sissy Jenna First Lesson

63% HD 1:01 / 17:38

Sissy Jenna First Lesson

FapHouse 3 år sedan

Stretch Your Ass for Me

63% HD 0:39 / 17:30

Stretch Your Ass for Me

FapHouse 1 vecka sedan

Emmalee Jones Party on Feb 26, 2026 - Part 2

66% 4K 2:00 / 17:04

Emmalee Jones Party on Feb 26, 2026 - Part 2

Flirt4Free 8 månader sedan

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

59% HD 1:01 / 47:50

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

FapHouse 1 månad sedan

Fucked and on the Edge of Orgasm - Sissy Slut Training

65% HD 1:01 / 14:43

Fucked and on the Edge of Orgasm - Sissy Slut Training

FapHouse 1 år sedan

Bi Femdom Blowjob POV, Two MILF Mouths One Cock, Bisexual Encouragement

57% HD 1:01 / 10:19

Bi Femdom Blowjob POV, Two MILF Mouths One Cock, Bisexual Encouragement

FapHouse 1 månad sedan

I'm a dirty slave of my wife... she can do everything with me

I'm a dirty slave of my wife... she can do everything with me

XHamster 10 månader sedan

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

54% HD 1:01 / 10:37

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FapHouse 1 år sedan

Ashley Sinn Private Show

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Ashley Sinn Private Show

Flirt4Free 1 år sedan

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

52% HD 1:01 / 13:10

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

FapHouse 11 månader sedan

Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

57% 1:01 / 20:13

Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

FapHouse 2 år sedan

The sissy, his Wife & The Saleswoman - Kendra James and Star Nine Pantyhose Domination, Sissy Sluts, Double Domination, Sissy Training

60% HD 0:10 / 13:05

The sissy, his Wife & The Saleswoman - Kendra James and Star Nine Pantyhose Domination, Sissy Sluts, Double Domination, Sissy Training

LoyalFans 4 månader sedan

Cucky Limo

HD 0:24 / 15:05

IWantClips 4 månader sedan

J.o.i. Stroke It, Jerk-off Instructions

68% 4K 2:00 / 2:09

J.o.i. Stroke It, Jerk-off Instructions

Flirt4Free 8 år sedan

Sissy Training in Chastity

71% HD 1:01 / 9:54

Sissy Training in Chastity

FapHouse 2 år sedan

Men Fucks, Betas Are Fucked.

58% HD 1:01 / 11:14

Men Fucks, Betas Are Fucked.

FapHouse 3 år sedan

Hope Daylee Sexy Secretary Bj

56% HD 2:00 / 4:23

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Flirt4Free 9 år sedan

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

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

XHamster 1 månad sedan

Jessie Evans Private Show

65% 4K 2:00 / 7:27

Jessie Evans Private Show

Flirt4Free 1 månad sedan

Sissy Strip Tease

65% 4K 0:25 / 9:31

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Clips4sale 1 månad sedan

Tara Alison Private Show

HD 2:00 / 1:07:43

Tara Alison Private Show

Flirt4Free 1 år sedan

Best of Harmony Rose volume 4

Best of Harmony Rose volume 4

XHamster 1 år sedan

Slave training in heat

Slave training in heat

XHamster 1 år sedan

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

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

XHamster 2 månader sedan

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Chastity slave strapon fucked

XHamster 6 månader sedan

Training the Sissy

Training the Sissy

FapHouse 1 månad sedan

Girl Transformation Complete: Sissy Breeding with Dommy Rose

57% HD 0:29 / 21:28

Girl Transformation Complete: Sissy Breeding with Dommy Rose

IWantClips 4 månader sedan

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 5 år sedan

The Chastity Fuck

The Chastity Fuck

XHamster 3 veckor sedan

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teacher checks the mouth of his student. well, let s suck my dildo. feminization

PornBox 3 år sedan

Sissy Spanked and Caged by MILF Boss

Sissy Spanked and Caged by MILF Boss

XHamster 1 månad sedan

Sissy femboy makes chastity content and streams on chaturbate

Sissy femboy makes chastity content and streams on chaturbate

BigTitsLust 1 år sedan

Isadora Dunkan Private Show

64% 4K 2:00 / 9:25

Isadora Dunkan Private Show

Flirt4Free 1 månad sedan

Vends-ta-culotte - Anal training and strap-on pegging for a submissive man

Vends-ta-culotte - Anal training and strap-on pegging for a submissive man

XHamster 2 veckor sedan

Secretary Pegging Cucked Boss Cumshot Humiliation BDSM

Secretary Pegging Cucked Boss Cumshot Humiliation BDSM

Eporner 3 år sedan

Sissy Girls Day: Makeover and Feminization Training - PART 2

70% HD 0:10 / 15:06

Sissy Girls Day: Makeover and Feminization Training - PART 2

LoyalFans 1 år sedan

Perverted wife wants to have anal sex with submissive guy pegging rimming session #56

Perverted wife wants to have anal sex with submissive guy pegging rimming session #56

XHamster 2 år sedan

Sissy Bürofickstück! Damen Chefetage

63% 0:30 / 13:02

Sissy Bürofickstück! Damen Chefetage

Clips4sale 1 år sedan

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strp HEELS PANTYHOSE

XHamster 7 månader sedan

Shivering and Leaking of Lust and Frustration! - Chastity, Sissy Training, Pantyhose and Orgasm Denial with Miss Adrastea

68% HD 1:01 / 11:28

Shivering and Leaking of Lust and Frustration! - Chastity, Sissy Training, Pantyhose and Orgasm Denial with Miss Adrastea

FapHouse 4 månader sedan

Satin Sissy Training

Satin Sissy Training

Itsrealamateurs 1 månad sedan

Asmr Sensual Teasing Close up Blowjob

Asmr Sensual Teasing Close up Blowjob

XHamster 7 månader sedan

Sissyfication 3

54% HD 1:01 / 14:32

Sissyfication 3

FapHouse 1 år sedan

Do Your Makeup

Clips 2 veckor sedan

Gentle Bi Encouragement - Will You Suck Cock For Me?

Gentle Bi Encouragement - Will You Suck Cock For Me?

XHamster 1 år sedan

Shoving My High Heel in His Ass Pegging and Humiliating Sissy BF CUMS IN HIS OWN MOUTH

Shoving My High Heel in His Ass Pegging and Humiliating Sissy BF CUMS IN HIS OWN MOUTH

Eporner 3 år sedan

My Big Squeaky Sow

My Big Squeaky Sow

XHamster 8 månader sedan

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Real cuckold wife wants to suck cock together !!!

XHamster 10 månader sedan

CUCKOLD CUMS IN PANTIES LIKE A GIRL

CUCKOLD CUMS IN PANTIES LIKE A GIRL

XHamster 4 år sedan

Squirt! Double SISSYGASM

65% 0:14 / 21:32

Squirt! Double SISSYGASM

Clips4sale 3 veckor sedan

Submissive sissy slave gets intimate training from his dominant

Submissive sissy slave gets intimate training from his dominant

Yesvids 1 månad sedan

How to be properly trained by Ms. Amanda

How to be properly trained by Ms. Amanda

Xfeed 1 månad sedan

Femdom Pegging Gangbang Slave Kassie

Femdom Pegging Gangbang Slave Kassie

XHamster 1 månad sedan

Pegging my Sissy Slut

Pegging my Sissy Slut

XHamster 1 månad sedan

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 11 månader sedan

Femdom: Sissy Feminization!

Femdom: Sissy Feminization!

Amateur8 3 år sedan

Lauren Newton Private Show

54% HD 2:00 / 23:24

Lauren Newton Private Show

Flirt4Free 1 månad sedan

MISTRESS LORRAINE TRAINING HER SISSY (COMPLETE MOVIE)

MISTRESS LORRAINE TRAINING HER SISSY (COMPLETE MOVIE)

DrTuber 3 år sedan

Feminized Sissy Spanked Raw Plugged Vibrating

Feminized Sissy Spanked Raw Plugged Vibrating

XHamster 5 månader sedan

Sissy Doxy Gets Ding-dong Experience - Full Version

Sissy Doxy Gets Ding-dong Experience - Full Version

Lesbian8 1 månad sedan

Femdom Mastix Dominant-bitch V humiliates & fully feminizes chastity cuckold sissy sub thrall w/ sph 1/three

Femdom Mastix Dominant-bitch V humiliates & fully feminizes chastity cuckold sissy sub thrall w/ sph 1/three

SortPorn 2 år sedan

Submissive Man Pegged By Strong Independ Women Domina Femdom Cuckold

Submissive Man Pegged By Strong Independ Women Domina Femdom Cuckold

Eporner 3 år sedan

BBC Sissy Training

BBC Sissy Training

XHamster 2 månader sedan

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

60% HD 0:08 / 0:40

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

FapHouse 1 månad sedan

Mistresst - High Class Sissy Trained

Mistresst - High Class Sissy Trained

InPorn 5 år sedan

hands free cum in cage with new toy

hands free cum in cage with new toy

Fetishpapa 2 månader sedan

Mistress training sissies to play together

Mistress training sissies to play together

AbXXX 7 år sedan

Gefangener feminisiert von Mistress Susi (deutsch) Prisoner feminized by Mistress Susi WMV

70% 0:11 / 10:30

Gefangener feminisiert von Mistress Susi (deutsch) Prisoner feminized by Mistress Susi WMV

Clips4sale 4 år sedan

Lilith Fenix Private Show

Lilith Fenix Private Show

Flirt4Free 18 timmar sedan

Panties and Orgasm for My Good Little Sissy

57% 0:30 / 9:08

Panties and Orgasm for My Good Little Sissy

Clips 1 månad sedan

Pantyhose Aerobics Class For Sissies

64% HD 0:10 / 15:12

Pantyhose Aerobics Class For Sissies

LoyalFans 1 år sedan

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crazy sex machine fucks sissy s anal hole. her anal is destroyed

AnalVids 2 år sedan

Feminized Fucked Femdommed

50% HD 0:10 / 18:47

Feminized Fucked Femdommed

LoyalFans 1 år sedan

(1080P) FOOT FUCKING AND FISTING MY SISSY SLUT - Vivienne l'Amour trains her feminized sissy with a sensual strapon fuck, then stretches her wide with extreme fisting and lubed latex footing until she gapes

Premium HD 20:43

(1080P) FOOT FUCKING AND FISTING MY SISSY SLUT - Vivienne l'Amour trains her feminized sissy with a sensual strapon fuck, then stretches her wide with extreme fisting and lubed latex footing until she gapes

Clips4sale 1 vecka sedan

Big strapon pegging my Sissy

Big strapon pegging my Sissy

XHamster 2 år sedan

Miss Adrastea is riding your face while you’re in chastity

Miss Adrastea is riding your face while you’re in chastity

XHamster 5 år sedan

You just got EXPOSED as a SISSY! - ASMR role play

You just got EXPOSED as a SISSY! - ASMR role play

XHamster 7 månader sedan

Sissy-Erziehung zur Strapsschlampe im KG! - Sissy Training in Chastity

49% 4K 0:10 / 9:49

Sissy-Erziehung zur Strapsschlampe im KG! - Sissy Training in Chastity

Clips4sale 2 år sedan

My New Cuckold Maid

My New Cuckold Maid

Fapcat 4 år sedan

Bi Humiliation & Cum Clean up with a Female Audience

51% 1:01 / 8:42

Bi Humiliation & Cum Clean up with a Female Audience

FapHouse 1 år sedan

Sissy Date Night

53% 1:01 / 19:30

Sissy Date Night

FapHouse 3 månader sedan

Femdom Mistress Goddess V humiliates & fully feminizes chastity cuckold sissy sub slave w/ sph 1/3

Femdom Mistress Goddess V humiliates & fully feminizes chastity cuckold sissy sub slave w/ sph 1/3

Dafreeporn 2 år sedan

Sissy! Lick My Floor and Stay with Your Ass Open!

Sissy! Lick My Floor and Stay with Your Ass Open!

XHamster 2 månader sedan

Femdom Pegging Gangbang Slave Kassie

Femdom Pegging Gangbang Slave Kassie

XHamster 5 dagar sedan

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sissy whore training and domination by nylon female-corporalist

Dafreeporn 3 år sedan

Training My Sissy Maid To Be The Office Cum Dump!

HD 0:15 / 20:22

Training My Sissy Maid To Be The Office Cum Dump!

IWantClips 4 månader sedan

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

PornFreeNow 1 år sedan

Emmalee Jones Private Show

78% 4K 2:00 / 10:53

Emmalee Jones Private Show

Flirt4Free 10 månader sedan

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

61% HD 0:39 / 47:50

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

FapHouse 1 månad sedan

She FISTS him with His Own CUM!!!

She FISTS him with His Own CUM!!!

XHamster 4 år sedan

Step-mommy's Forever 2

58% 1:01 / 34:34

Step-mommy's Forever 2

FapHouse 2 månader sedan

Confess that you are a sissy to your best friend!

Confess that you are a sissy to your best friend!

XHamster 3 månader sedan

Sissy Maid Training With Zara Durose Stage 4 (MP4)

Sissy Maid Training With Zara Durose Stage 4 (MP4)

Clips4sale 11 månader sedan

Sissy Cuckold Transformation

Sissy Cuckold Transformation

Dafreeporn 6 år sedan

My owner becomes my SIssy

My owner becomes my SIssy

XHamster 3 år sedan

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 3 månader sedan

Darsy Pearly Private Show

Darsy Pearly Private Show

Flirt4Free 4 dagar sedan

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68% HD 0:30 / 3:00

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Clips4sale 1 år sedan

Elizabeth Whiler Private Show

47% HD 2:00 / 9:53

Elizabeth Whiler Private Show

Flirt4Free 3 år sedan

Jhanne Cherry Private Show

53% HD 2:00 / 8:06

Jhanne Cherry Private Show

Flirt4Free 1 år sedan

My cum eating chastity slave gets to clean my feet

My cum eating chastity slave gets to clean my feet

XHamster 1 år sedan

Kinky Stepmom in nylon Stockings Seduces Chaste stepson Dilon - Stepmother in Silk Japan Robe Masturbates hairy Pussy, Rubbing his Cock on Shoe High Heels, small Feet on Big Dick, Female Domination, Cum on Feet, Sensual Domination 4k

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Clips4sale 1 år sedan

Classy chick gets naughty in the great outdoors with a thong and bra on

Classy chick gets naughty in the great outdoors with a thong and bra on

Some.Porn 2 år sedan

Suck His Dick Loser

Suck His Dick Loser

XHamster 1 år sedan

Sissy Slave's First Stretching

63% HD 0:10 / 26:49

Sissy Slave's First Stretching

LoyalFans 3 år sedan

Sissy Husband Training - Teaching My Beta How to Suck a BBC

Sissy Husband Training - Teaching My Beta How to Suck a BBC

XHamster 1 vecka sedan

FEMDOM & SISSY PEGGING HOT SHOTS & CUMSHOTS COMPILATION

FEMDOM & SISSY PEGGING HOT SHOTS & CUMSHOTS COMPILATION

Lesbian8 1 år sedan

Jennas Suprise

XHamster 3 år sedan

Chelsea Roset Private Show

57% HD 2:00 / 26:30

Chelsea Roset Private Show

Flirt4Free 3 år sedan

Sex Doll Has Arrived

66% HD 0:39 / 32:44

Sex Doll Has Arrived

FapHouse 2 år sedan

POV Cuckold volume 13

POV Cuckold volume 13

XHamster 1 år sedan

Mistress shows her sex doll to the viewer in a kinky FemDom POV

Mistress shows her sex doll to the viewer in a kinky FemDom POV

S3xdolls 1 vecka sedan

Mistress gives Sissy a Ruined Orgasm in Chastity Cage - Massive Load of Cum Rubbed on Mask and Fed to Her

Mistress gives Sissy a Ruined Orgasm in Chastity Cage - Massive Load of Cum Rubbed on Mask and Fed to Her

XHamster 1 år sedan

Il fidanzato in collant - The boyfriend in pantyhose #2 ( 1 PART MP4 - MOBILE VERSION )

HD 0:09 / 16:03

Il fidanzato in collant - The boyfriend in pantyhose #2 ( 1 PART MP4 - MOBILE VERSION )

Clips4sale 3 månader sedan

Sissy sniffs step-mammy's and aunty's nylon feet

HD 0:35 / 13:55

Sissy sniffs step-mammy's and aunty's nylon feet

Clips4sale 4 år sedan

Mistress Takes Sissy To Gloryhole To Suck Real Cocks F4M Audio Blowjob

Mistress Takes Sissy To Gloryhole To Suck Real Cocks F4M Audio Blowjob

AveXXX 1 vecka sedan

Akira Sissifies Jessica (HD WMV)

58% HD 0:26 / 13:00

Akira Sissifies Jessica (HD WMV)

Clips4sale 1 år sedan

Dollification Transformation - 1080HD

63% 0:15 / 10:10

Dollification Transformation - 1080HD

Clips4sale 3 år sedan

(720P) FOOT FUCKING AND FISTING MY SISSY SLUT - Vivienne l'Amour trains her feminized sissy with a sensual strapon fuck, then stretches her wide with extreme fisting and lubed latex footing until she gapes

Premium HD 20:43

(720P) FOOT FUCKING AND FISTING MY SISSY SLUT - Vivienne l'Amour trains her feminized sissy with a sensual strapon fuck, then stretches her wide with extreme fisting and lubed latex footing until she gapes

Clips4sale 1 vecka sedan

Sammie Earns It - Kinky Sub Girl

Premium 4K 9:52

Sammie Earns It - Kinky Sub Girl

C4S 6 dagar sedan

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