Sissy Training (79,012)

The best and newest sissy training videos

Day 25 Sissy training programme: How to get the perfect pout as a sissy

66% HD 0:30 / 9:13

Day 25 Sissy training programme: How to get the perfect pout as a sissy

C4S 2 months ago

Panty Sissy (NSFW)

62% 0:30 / 8:52

Panty Sissy (NSFW)

Clips4sale 1 year ago

Double Dommes Fuck the Bimbo Slut 4K ft Mistress Damazonia

4K 0:22 / 14:14

Double Dommes Fuck the Bimbo Slut 4K ft Mistress Damazonia

Clips4sale 9 months ago

Cuckold sissy and alpha BBC this perfect combination

59% 1:00 / 35:55

Cuckold sissy and alpha BBC this perfect combination

Clips4sale 3 months ago

Slavecation Day 13: Pegging My Sissy Maid

62% 0:25 / 13:14

Slavecation Day 13: Pegging My Sissy Maid

Clips4sale 3 years ago

Bi-Curious Bro Gets A Sissy Sandwich

Bi-Curious Bro Gets A Sissy Sandwich

Fapnado 2 months ago

Sissy Maid Punishment!

66% 0:11 / 5:29

Sissy Maid Punishment!

Clips4sale 2 years ago

Anal Training for Lexi - Bottom Bitch Stretching Instructions Slut Encouragement POV Strapon - 1080p MP4

49% HD 0:24 / 11:11

Anal Training for Lexi - Bottom Bitch Stretching Instructions Slut Encouragement POV Strapon - 1080p MP4

Clips4sale 1 year ago

Cuckold Fantasies Volume 20

Cuckold Fantasies Volume 20

xHamster 3 years ago

The Career Sissy (SD MP4)

4K 0:30 / 13:24

The Career Sissy (SD MP4)

Clips4sale 1 year ago

First Step To Sissy Full Scene

First Step To Sissy Full Scene

CrazyPorn 3 years ago

Locktober Special - Day Zero: The Last Cum

Locktober Special - Day Zero: The Last Cum

xHamster 6 months ago

[823] Strap and Birch

68% 0:55 / 32:50

[823] Strap and Birch

Clips4sale 1 year ago

Sissy Cuck Clean Creampie After Wife's Date

Sissy Cuck Clean Creampie After Wife's Date

xHamster 8 months ago

Sissy cuckold trained to love cum and ruined orgasms by dominant mistress

Sissy cuckold trained to love cum and ruined orgasms by dominant mistress

XXXShake 2 years ago

Cuckold Sexsklave Part 2 - CEI

71% 0:44 / 9:53

Cuckold Sexsklave Part 2 - CEI

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 1 year ago

I PENETRATE DEEP UNTIL HE COMES

I PENETRATE DEEP UNTIL HE COMES

Love4Porn 2 years ago

Trance: Satin Sissy

60% HD 0:11 / 15:47

Trance: Satin Sissy

Clips4sale 3 years ago

Punishing My Disobedient Sissy Slave

59% 0:25 / 23:04

Punishing My Disobedient Sissy Slave

C4S 2 years ago

Charlotte Texas Private Show

Charlotte Texas Private Show

Flirt4Free 10 years ago

Anal training JOI edging and denial

Anal training JOI edging and denial

4KPorn 3 years ago

Jen Holly Private Show

Jen Holly Private Show

Flirt4Free 4 months ago

TEACHING YOU TO SUCK HIS BALLS

56% 4K 0:32 / 22:41

TEACHING YOU TO SUCK HIS BALLS

Jen Holly Private Show

Premium 51% 8:15

Jen Holly Private Show

Flirt4Free 2 months ago

Jen Holly Private Show

Premium 67% 8:09

Jen Holly Private Show

Flirt4Free 3 months ago

1 way to Cum. Female Domination Dick Milking

1 way to Cum. Female Domination Dick Milking

CrazyPorn 3 years ago

Lizzy Miller Party on Mar 23, 2022

Premium 51% 36:03

Lizzy Miller Party on Mar 23, 2022

Flirt4Free 3 years ago

Elizabeth Whiler Private Show

Elizabeth Whiler Private Show

Flirt4Free 2 years ago

Amazing Blowjob

Premium 65% 10:58

Amazing Blowjob

Flirt4Free 9 months ago

Sissy Training - Sucking That Dick and Swallow the Load

Sissy Training - Sucking That Dick and Swallow the Load

Analdin 5 years ago

Pegging POV - Your New Life as a Sissy Wife

43% 4K 0:29 / 10:47

Pegging POV - Your New Life as a Sissy Wife

Clips4sale 1 month ago

Sissy Slut Panty Thief

78% HD 0:29 / 11:07

Sissy Slut Panty Thief

Clips4sale 1 year ago

Sissy slut moans loudly while taking her new giant plug

Sissy slut moans loudly while taking her new giant plug

Lesbian8 5 months ago

Sissy smoking training 4K

4K 0:30 / 22:32

Sissy smoking training 4K

C4S 6 months ago

Lick My ass and orgasm through pantyhose

66% 0:36 / 17:43

Lick My ass and orgasm through pantyhose

Clips4sale 2 years ago

Lady Sara Borgia's Sissy School (1080p)

69% HD 0:25 / 15:27

Lady Sara Borgia's Sissy School (1080p)

Clips4sale 4 weeks ago

Sissy femboy makes chastity content and streams on chaturbate

Sissy femboy makes chastity content and streams on chaturbate

SortPorn 1 month ago

Mistress Mavka will use her sissy slut

66% 0:21 / 5:11

Mistress Mavka will use her sissy slut

Clips4sale 1 year ago

Sissy Bible: Malvoria’s Wicked Holy Smackdown

69% 0:30 / 18:29

Sissy Bible: Malvoria’s Wicked Holy Smackdown

Clips4sale 1 month ago

Prison inspection at Omega Compound - Sissy training - Zeida, Alexandra, Zara and Agnes

35% HD 0:11 / 5:26

Prison inspection at Omega Compound - Sissy training - Zeida, Alexandra, Zara and Agnes

Clips4sale 3 months ago

Husband Turned Girlfriend Pt 3

63% HD 0:11 / 20:35

Husband Turned Girlfriend Pt 3

Clips4sale 2 years ago

Double Locked Sissy - Star Nine Mobile

39% 0:13 / 21:59

Double Locked Sissy - Star Nine Mobile

Clips4sale 2 years ago

Hentai Comics - The Hot Wife ep.1 By MissKitty2K

Hentai Comics - The Hot Wife ep.1 By MissKitty2K

xHamster 10 months ago

Feminizing You, Part 1 (WITH 3D AUDIO)

55% HD 0:25 / 12:41

Feminizing You, Part 1 (WITH 3D AUDIO)

Clips4sale 1 year ago

Sissy School Beginners Class Chastity (1080p)

57% HD 0:25 / 14:39

Sissy School Beginners Class Chastity (1080p)

Clips4sale 3 weeks ago

elf femboy in chastity strap gets constricted butt stretched by bbc schlong and screw machine until cum

elf femboy in chastity strap gets constricted butt stretched by bbc schlong and screw machine until cum

BigTitsLust 1 month ago

Interracial feminizing cuckolding with erectile dysfunction featuring Maisa Pravo

61% 4K 1:00 / 39:21

Interracial feminizing cuckolding with erectile dysfunction featuring Maisa Pravo

Clips4sale 3 months ago

Date Night! Cucked & Feminized (720p)

45% HD 0:30 / 21:20

Date Night! Cucked & Feminized (720p)

Clips4sale 1 year ago

MISTRESS ISIDE - ORGASM IN CHASTITY mobile version

66% 0:24 / 12:40

MISTRESS ISIDE - ORGASM IN CHASTITY mobile version

Clips4sale 2 months ago

Sissys hardcore whore training

Sissys hardcore whore training

xHamster 2 years ago

Bi Humiliation & Cum Clean up

Bi Humiliation & Cum Clean up

xHamster 4 weeks ago

Sissy Piss Training with Dommy Mommy - Mistress Kendra wmv

54% 0:11 / 22:06

Sissy Piss Training with Dommy Mommy - Mistress Kendra wmv

Clips4sale 2 years ago

Lingerie Lover - Sissy Pegging POV

Lingerie Lover - Sissy Pegging POV

xHamster 4 weeks ago

Heartfelt BNWO Conversation About Castration (Why You Should Do It)

71% 1:00 / 10:13

Heartfelt BNWO Conversation About Castration (Why You Should Do It)

Clips4sale 1 month ago

Dom Mara Give A Strap-On It to Her Sissy JD

Dom Mara Give A Strap-On It to Her Sissy JD

4KPorn 3 years ago

SISSY DRESS UP

59% 0:30 / 9:04

Clips4sale 4 months ago

Sissy slut penetrated and humiliated by Lady Perse

66% 0:26 / 17:35

Sissy slut penetrated and humiliated by Lady Perse

Clips4sale 2 years ago

Step-Mommy Teaches You to Suck Cock - WMV

64% 0:30 / 11:54

Step-Mommy Teaches You to Suck Cock - WMV

Clips4sale 4 weeks ago

Training the Femboy Sissies! (720p)

44% HD 0:30 / 9:38

Training the Femboy Sissies! (720p)

Clips4sale 9 months ago

Superman Becomes Super Sissy

66% 0:30 / 12:23

Superman Becomes Super Sissy

Clips4sale 5 months ago

Ass Owned by Jasmine Mendez

49% 0:20 / 9:10

Ass Owned by Jasmine Mendez

Clips4sale 1 month ago

Dominating Our Cucks Strap On

66% 0:09 / 7:07

Dominating Our Cucks Strap On

Clips4sale 3 years ago

Under My Control (720p)

72% HD 0:30 / 14:21

Under My Control (720p)

Clips4sale 3 years ago

Your Sissy dream come True - Female POV blowjob - Roleplay

Your Sissy dream come True - Female POV blowjob - Roleplay

xHamster 10 months ago

2 Dommes made sissy training for this slut | Lady Perse, Saint Shinaina

66% 0:26 / 14:59

2 Dommes made sissy training for this slut | Lady Perse, Saint Shinaina

Clips4sale 6 months ago

Sissy & cuckold training

49% HD 0:39 / 11:45

Sissy & cuckold training

FapHouse 4 years ago

19 year old booty wrecked by roommate

19 year old booty wrecked by roommate

CrazyPorn 2 years ago

Bisexual husband gets fucked by three strapons

Bisexual husband gets fucked by three strapons

xHamster 11 months ago

Step-Mommy's Forever 2

62% 4K 0:30 / 34:28

Step-Mommy's Forever 2

Clips4sale 3 months ago

Your FIRST Gloryhole Cock - Bi Encouraged Suck And Swallow

49% HD 0:12 / 10:54

Your FIRST Gloryhole Cock - Bi Encouraged Suck And Swallow

Clips4sale 3 weeks ago

Clean My BBC Bulls Cum Off Your Chastity Cage WMV

68% 0:32 / 11:26

Clean My BBC Bulls Cum Off Your Chastity Cage WMV

Clips4sale 2 months ago

Feminizing my Boyfriend and Pegging in Latex!

55% HD 0:32 / 15:54

Feminizing my Boyfriend and Pegging in Latex!

Clips4sale 4 months ago

Slave No Limits part #2 - Double Penetration StrapOn & CreamPie

Slave No Limits part #2 - Double Penetration StrapOn & CreamPie

Clips4sale 7 months ago

MISTRESS LORRAINE TRAINING HER SISSY (COMPLETE MOVIE)

MISTRESS LORRAINE TRAINING HER SISSY (COMPLETE MOVIE)

DrTuber 1 year ago

Sissy Bra Slut: Clitty Cunt Fucking 4K

4K 0:10 / 18:13

Sissy Bra Slut: Clitty Cunt Fucking 4K

LoyalFans 1 year ago

Sissy stored and sexually used

68% 0:30 / 14:32

Sissy stored and sexually used

Clips4sale 2 months ago

SISSYGASM 1080P - ELLIE IDOL

50% HD 0:27 / 24:49

SISSYGASM 1080P - ELLIE IDOL

Clips4sale 1 year ago

Gentle Bi Encouragement - Will You Suck Cock For Me?

Gentle Bi Encouragement - Will You Suck Cock For Me?

xHamster 3 months ago

Dominated and pegged sissy boi by hawt wife

Dominated and pegged sissy boi by hawt wife

SortPorn 1 week ago

First time pegging makes him cum inside minutes

First time pegging makes him cum inside minutes

CrazyPorn 2 years ago

U Will Suck Penis Bi-Sexual Encouragement Binaural Beats Erotic Audio Mesmerizing by Tara Smith

U Will Suck Penis Bi-Sexual Encouragement Binaural Beats Erotic Audio Mesmerizing by Tara Smith

SortPorn 3 years ago

My Cuckold Slave Cleanup Cum From My Pussy and Beverage My Piss and Licks My Pussy Clean

My Cuckold Slave Cleanup Cum From My Pussy and Beverage My Piss and Licks My Pussy Clean

xHamster 1 year ago

I Milked His Cock, He Fucked My Throat - I Swallowed a Lot of Cum - Female POV

I Milked His Cock, He Fucked My Throat - I Swallowed a Lot of Cum - Female POV

xHamster 11 months ago

Gigantic Vibrator strap on and pegging.

Gigantic Vibrator strap on and pegging.

4KPorn 2 years ago

Gf Finger Fuck and His Bombshell Booty

Gf Finger Fuck and His Bombshell Booty

4KPorn 3 years ago

Kristinaxxx sissy training

Kristinaxxx sissy training

AnySex 1 year ago

Turned into a Prissy Sissy Dolly Bird! (1080p)

53% HD 0:30 / 9:44

Turned into a Prissy Sissy Dolly Bird! (1080p)

Clips4sale 9 months ago

How to cum without hands lesson 3 by Mistress Mary!

How to cum without hands lesson 3 by Mistress Mary!

xHamster 1 year ago

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 6 months ago

Pegging men is My pleasure

73% HD 0:39 / 18:32

Pegging men is My pleasure

Clips4sale 3 years ago

Sissyfied For Latina Curves

Sissyfied For Latina Curves

Clips4sale 2 years ago

Becoming a sissy

Becoming a sissy

FreePorn8 4 years ago

Her femboy stands and flows like a whore

Her femboy stands and flows like a whore

xHamster 2 years ago

Girlfriend Sucks Bull While Subs Stroke To Taste Cum ( Live Compilation )

Girlfriend Sucks Bull While Subs Stroke To Taste Cum ( Live Compilation )

Love4Porn 2 years ago

Wife fucks husband in the ass and treats him like a pegging sissy part 2

Wife fucks husband in the ass and treats him like a pegging sissy part 2

xHamster 1 year ago

Sissy Gangbang with BBC, Mistress Angelina and Slavena

56% 0:11 / 12:06

Sissy Gangbang with BBC, Mistress Angelina and Slavena

Clips4sale 10 months ago

Who's Fucking Who? - StrapOn

67% 0:32 / 10:05

Who's Fucking Who? - StrapOn

Clips4sale 5 months ago

Cowgirls Cocks- StrapOn!

Cowgirls Cocks- StrapOn!

Clips4sale 1 month ago

Take My Mexican Dick - StrapOn

67% 0:40 / 15:03

Take My Mexican Dick - StrapOn

Clips4sale 6 months ago

Mistresst - High Class Sissy Trained

Mistresst - High Class Sissy Trained

InPorn 3 years 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 month ago

We will fuck you and let you work the streets

66% 0:26 / 6:54

We will fuck you and let you work the streets

Clips4sale 6 months ago

You Will Be Wearing a Headscarf Today Sissy Kelly

You Will Be Wearing a Headscarf Today Sissy Kelly

xHamster 7 months ago

poked from behind and in front

poked from behind and in front

Clips4sale 1 year ago

Wonder Woman makes u Suck Superman's Jock at a Party

Wonder Woman makes u Suck Superman's Jock at a Party

SortPorn 4 years ago

Mistress Victoria Rey Collars, gags, humiliates, spits on her hot chastity sissy slave husband. SPH loser Chastity Pt 1 of 5

Mistress Victoria Rey Collars, gags, humiliates, spits on her hot chastity sissy slave husband. SPH loser Chastity Pt 1 of 5

xHamster 3 months ago

Femdom Real Pair female domination pegging & ding-dong mastix & sissy cuck feminization FULL clip

Femdom Real Pair female domination pegging & ding-dong mastix & sissy cuck feminization FULL clip

SortPorn 6 months ago

You are her now!!! Take her place and get on your knees. Amazing female POV with deepthroat, rimjob, ass fingering and cumshot

You are her now!!! Take her place and get on your knees. Amazing female POV with deepthroat, rimjob, ass fingering and cumshot

xHamster 1 year ago

SissyK Sucks Dick for Goddess - Sissy Slut Training

63% 0:27 / 9:02

SissyK Sucks Dick for Goddess - Sissy Slut Training

Clips4sale 1 year ago

Boyfriend to Girlfriend P3 : First Fucking as Femme (720)

66% HD 0:11 / 7:42

Boyfriend to Girlfriend P3 : First Fucking as Femme (720)

Clips4sale 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 1 year ago

Eat That Cum Sissy Training POV JOI

Eat That Cum Sissy Training POV JOI

FetishShrine 3 years ago

My nylon-addicted sissy slut

My nylon-addicted sissy slut

Clips4sale 2 years ago

Mistress Luna and Faith - Strapon fucking my sissy slut in hotel

66% HD 0:17 / 18:23

Mistress Luna and Faith - Strapon fucking my sissy slut in hotel

Clips4sale 1 year ago

AmberSis - Manufactured To Serve

AmberSis - Manufactured To Serve

Eporner 5 years ago

Sissy femboy makes chastity content and streams on chaturbate

Sissy femboy makes chastity content and streams on chaturbate

BigTitsLust 1 month ago

Lick my pussy while he fucks your ass cuckold

Lick my pussy while he fucks your ass cuckold

XVideos 8 years ago

Sissy red lipstick fetish training

Sissy red lipstick fetish training

XVideos 11 months ago

Sissy Trainer presents: I am a Woman

Sissy Trainer presents: I am a Woman

Eporner 5 years ago

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