Sissy Training (147,017)

The best and newest sissy training videos

Bi Humiliation & Cum Clean up with a Female Audience

48% 1:01 / 8:42

Bi Humiliation & Cum Clean up with a Female Audience

FapHouse 1 year ago

Hostess Makes You Her Bitch Roleplay Verbal Humiliation Bisexual Encouragement Feminization

59% HD 1:01 / 8:05

Hostess Makes You Her Bitch Roleplay Verbal Humiliation Bisexual Encouragement Feminization

FapHouse 1 year ago

Two Dominatrix Femdom Ritual Humiliation, Ballbusting, Slave Training, Feminization and Anal Punishment - French Pegging

HD 1:01 / 30:48

Two Dominatrix Femdom Ritual Humiliation, Ballbusting, Slave Training, Feminization and Anal Punishment - French Pegging

FapHouse 3 weeks ago

Amelia Sweety Private Show

Amelia Sweety Private Show

Camster 2 weeks ago

Gym workout gone wrong for asian teen and turned into sex

Gym workout gone wrong for asian teen and turned into sex

XGroovy 2 years ago

XL Thor Teaches Cucky How Bulls Fuck- Taperedphysique, Thor, CJ Films

Premium HD 12:09

XL Thor Teaches Cucky How Bulls Fuck- Taperedphysique, Thor, CJ Films

XNXXGold 1 month ago

Sissy Dress Up & Humiliation

Sissy Dress Up & Humiliation

LoyalFans 2 weeks ago

SISSYFICATION ASS AND ARMPITS SNIFFING - WITH TWO BLONDES GODDESSESS

HD 0:15 / 32:37

SISSYFICATION ASS AND ARMPITS SNIFFING - WITH TWO BLONDES GODDESSESS

IWantClips 3 weeks ago

Suck Cock and Swallow Hot Cum - Obey Your Mistress

Suck Cock and Swallow Hot Cum - Obey Your Mistress

XHamster 1 year ago

Naughty Nun's Spanking Punishment Secrets Revealed!

Naughty Nun's Spanking Punishment Secrets Revealed!

GiveMeAPorn 4 weeks ago

Tinkerbell Dresses You up Too

HD 0:39 / 14:33

Tinkerbell Dresses You up Too

FapHouse 1 month ago

Jhanne Cherry Private Show

53% HD 2:00 / 40:31

Jhanne Cherry Private Show

Flirt4Free 9 months ago

Goddess Sissy Training Cock Worshiper CEI

Goddess Sissy Training Cock Worshiper CEI

Nuvid 4 years ago

Miss Brit Slave Training of Sofie Marie

Miss Brit Slave Training of Sofie Marie

XHamster 4 months ago

Jennas Suprise

XHamster 2 years ago

Hanging balls

Clips4sale 1 year ago

Cum Like A Girl

56% HD 0:21 / 14:07

Cum Like A Girl

IWantClips 3 years ago

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

61% HD 1:01 / 5:10

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

FapHouse 11 months ago

Sissy Fails Her Heels Test & Pays The Price — Inspected, Humiliated & Spanked Into Submission By Her Asian Goddess — Femdom Sissy Training Part 1 of 6 | Goddess AsunaBloom

Premium 4K 7:39

Sissy Fails Her Heels Test & Pays The Price — Inspected, Humiliated & Spanked Into Submission By Her Asian Goddess — Femdom Sissy Training Part 1 of 6 | Goddess AsunaBloom

Clips4sale 2 weeks ago

Kaitlyn Manson Private Show

4K 2:00 / 46:09

Kaitlyn Manson Private Show

Flirt4Free 1 week ago

MISTRESS LILY DUPONT : SLUT TRAINING DEEP THROAT

MISTRESS LILY DUPONT : SLUT TRAINING DEEP THROAT

Clips4sale 2 years ago

fat cock to ruin your virgin ass

fat cock to ruin your virgin ass

Fetishpapa 1 day ago

Big-dicked sissy takes it up the ass and swallows his own cum

Big-dicked sissy takes it up the ass and swallows his own cum

XXXShake 3 years ago

you in My nightgown

63% HD 0:15 / 8:54

you in My nightgown

IWantClips 3 weeks ago

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 1 year ago

SOLO SIRVES PARA UNA COSA

45% 0:15 / 9:09

SOLO SIRVES PARA UNA COSA

Clips4sale 3 years ago

Guided Humiliation for True Devated Lasers big beautiful woman JOI HUMILIATION FEMDOM mother I'd like to fuck

Guided Humiliation for True Devated Lasers big beautiful woman JOI HUMILIATION FEMDOM mother I'd like to fuck

MatureTubeHere 5 days ago

Bi Encouragement - Let Me Help You Give Your First Blowjob

60% 1:01 / 12:42

Bi Encouragement - Let Me Help You Give Your First Blowjob

FapHouse 1 year ago

Guys, for the First Time I Got Myself Fucked by the Pantry Boy in a Moving Train, He Fucked Me Hard and Tore My Pussy

52% HD 1:01 / 9:48

Guys, for the First Time I Got Myself Fucked by the Pantry Boy in a Moving Train, He Fucked Me Hard and Tore My Pussy

FapHouse 8 months ago

sissy pegging: british milf strapon fucks a sissy over the desk, anal training butt plug, cei cum eating humiliation

HD 0:30 / 20:43

sissy pegging: british milf strapon fucks a sissy over the desk, anal training butt plug, cei cum eating humiliation

PornBox 3 days ago

Delivery Guy Becomes a Sissy

65% HD 0:39 / 13:05

Delivery Guy Becomes a Sissy

FapHouse 5 months ago

Sissy strapon pegging by 3 Mistress

HD 0:39 / 11:16

Sissy strapon pegging by 3 Mistress

FapHouse 3 years ago

Testicular massage Ruined anew

Testicular massage Ruined anew

SortPorn 4 weeks ago

Lady Perse - Sissy Training For Our Slut

Lady Perse - Sissy Training For Our Slut

VipTube 1 month ago

Hotel Dick Sucking for Sissy Training

66% HD 0:15 / 15:02

Hotel Dick Sucking for Sissy Training

IWantClips 7 years ago

Sissy Anal Training by Latex Dommes

Sissy Anal Training by Latex Dommes

FapHouse 1 year ago

From Alpha to Bimbo

From Alpha to Bimbo

Fetishpapa 3 weeks ago

Akira Sissifies Jessica (HD WMV)

50% HD 0:26 / 13:00

Akira Sissifies Jessica (HD WMV)

Clips4sale 10 months ago

Sniff My Dirty Panties Pervert POV JOI

Sniff My Dirty Panties Pervert POV JOI

FetishShrine 4 years ago

Fun Feminization

54% HD 0:10 / 5:34

Fun Feminization

LoyalFans 1 year ago

Beach Abode Feminization at the Shore [Preview]

Beach Abode Feminization at the Shore [Preview]

SortPorn 2 weeks ago

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

54% 4K 0:25 / 16:22

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

Clips4sale 9 months ago

Sisk release her love button from chastity cage

Sisk release her love button from chastity cage

BigTitsLust 3 weeks ago

Dominant GF Wrecks BFs Asshole - Anal Punch Fisting, Double Anal Fisting (011A)

Dominant GF Wrecks BFs Asshole - Anal Punch Fisting, Double Anal Fisting (011A)

Pornfact 1 week ago

Slut School Part 2: Sissy CEI Training

Slut School Part 2: Sissy CEI Training

Pornzona 1 month ago

Femdom dick play and advanced fisting

Femdom dick play and advanced fisting

Pornzona 2 weeks ago

Gentle Bi Encouragement - Will You Suck Cock For Me?

Gentle Bi Encouragement - Will You Suck Cock For Me?

XHamster 1 year ago

She rimmed him so she could pegging him later

She rimmed him so she could pegging him later

XHamster 10 months ago

Femdom Humiliation - Oops, I've Made You Gay!

44% HD 1:01 / 18:20

Femdom Humiliation - Oops, I've Made You Gay!

FapHouse 3 months ago

Fisting My anal slut

Fisting My anal slut

Pornfact 1 week ago

Sissy Kendall Anal Training & Slave Affirmations

57% HD 1:01 / 10:20

Sissy Kendall Anal Training & Slave Affirmations

FapHouse 3 months ago

My Loser Beta Sissy Cuckold Jason

HD 0:39 / 15:44

My Loser Beta Sissy Cuckold Jason

FapHouse 3 months ago

Two Baldur's Gate 3 players having sex

Two Baldur's Gate 3 players having sex

XHamster 5 months ago

Chastity Anal Slut new

4K 0:19 / 15:21

Chastity Anal Slut new

Clips4sale 1 year ago

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

49% HD 1:01 / 19:18

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

FapHouse 6 months ago

You Need to Be Punished Taboo Fetish Femdom Strap on

43% HD 1:01 / 12:05

You Need to Be Punished Taboo Fetish Femdom Strap on

FapHouse 1 year ago

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

XHamster 5 months ago

Sissy in chastity - feminization - verbal instructions - anal training

HD 0:25 / 11:04

Sissy in chastity - feminization - verbal instructions - anal training

Clips4sale 1 month ago

Domina Dark - Dizzy Miss Sissy In Training

Domina Dark - Dizzy Miss Sissy In Training

Nuvid 1 year ago

Bella Brookz Private Show

48% HD 2:00 / 9:32

Bella Brookz Private Show

Flirt4Free 3 years ago

Freshies Juice Box - Latex Sissy Maid Training

Freshies Juice Box - Latex Sissy Maid Training

IcePorn 11 months ago

Dahlia VR trains princess Zoey

56% HD 0:10 / 14:28

Dahlia VR trains princess Zoey

LoyalFans 6 months ago

Ruined Orgasm Scene From Hospital 1

64% HD 0:39 / 5:25

Ruined Orgasm Scene From Hospital 1

FapHouse 1 year ago

sissy joyce - goddess annie i love their helpless porn video

sissy joyce - goddess annie i love their helpless porn video

BDSMShip 1 year ago

Woman Fucks Her Husband in the Anus #044 Training Sissy Lesbian Dildo

Woman Fucks Her Husband in the Anus #044 Training Sissy Lesbian Dildo

XHamster 5 months ago

Brittney & Elvis Private Show

66% HD 2:00 / 6:22

Brittney & Elvis Private Show

Camster 2 years ago

Baby in paradise part 1

62% HD 0:39 / 9:01

Baby in paradise part 1

FapHouse 3 years ago

WaterSports Sissy Humiliation

65% HD 0:25 / 9:36

WaterSports Sissy Humiliation

IWantClips 1 year ago

PROSTATE ORGASM COMPILATION SISSY

PROSTATE ORGASM COMPILATION SISSY

XHamster 4 years ago

Sweet & Daaniel Private Show

64% HD 2:00 / 14:05

Sweet & Daaniel Private Show

Camster 3 weeks ago

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 1 year ago

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 4 years ago

i made my little sissy have a chastity orgasm

i made my little sissy have a chastity orgasm

XHamster 5 months ago

Femdom Slave Training - Part 2 - Double Fisting, Ball Crushing, Punch Fisting, Gaping

60% 1:01 / 8:44

Femdom Slave Training - Part 2 - Double Fisting, Ball Crushing, Punch Fisting, Gaping

FapHouse 3 years ago

Jen Holly Private Show

52% HD 2:00 / 4:27

Jen Holly Private Show

Camster 1 year ago

SLAVE ON THE THRONE - Restrained Prostate Machine Stimulation - Chair Tied

SLAVE ON THE THRONE - Restrained Prostate Machine Stimulation - Chair Tied

Pornzona 1 month ago

POV Cuckold volume 15

POV Cuckold volume 15

XHamster 4 years ago

Call me Daddy - Strap On

Call me Daddy - Strap On

Clips4sale 2 months ago

... - Part 3

55% 4K 2:00 / 4:53

Flirt4Free 2 weeks ago

Tutorial to be the *cutest sissy at the party* makeup + anal dilation for whores!

Tutorial to be the *cutest sissy at the party* makeup + anal dilation for whores!

Pornzona 1 month ago

After a Blowjob, She Plays Snowballs with Him (cumkiss, a Lot of Cum, Cuckold Training)

After a Blowjob, She Plays Snowballs with Him (cumkiss, a Lot of Cum, Cuckold Training)

FapHouse 7 months ago

”Bi-Curious Bro Gets A Sissy Sandwich”

”Bi-Curious Bro Gets A Sissy Sandwich”

TransHero 6 months ago

Your Slutty Sissy Fantasy 2

HD 0:15 / 20:12

Your Slutty Sissy Fantasy 2

IWantClips 3 weeks ago

Jen Holly Private Show

61% HD 2:00 / 5:45

Jen Holly Private Show

Camster 1 year ago

Blush In Pigtails For My Real Man Sissy! (HD MP4)

4K 0:32 / 14:54

Blush In Pigtails For My Real Man Sissy! (HD MP4)

Clips4sale 6 months ago

Living Piece of Furniture 1 - Mistress Orgasm

Living Piece of Furniture 1 - Mistress Orgasm

XHamster 1 year ago

Baby in paradise part 1

55% HD 1:01 / 9:01

Baby in paradise part 1

FapHouse 3 years 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 3 years ago

Bimbo Transformation: Dominant Woman Takes Control

Bimbo Transformation: Dominant Woman Takes Control

XXXShake 3 years ago

How to give a prostate massage

How to give a prostate massage

SortPorn 2 years ago

Turning Pupcup Into Our Perfect Sissy Slut

58% HD 0:29 / 23:59

Turning Pupcup Into Our Perfect Sissy Slut

IWantClips 8 months ago

Sissy training - Part 1: Trained to love cock

67% HD 0:10 / 8:25

Sissy training - Part 1: Trained to love cock

LoyalFans 1 year ago

... - Part 3

55% 4K 2:00 / 4:53

Camster 2 weeks ago

Sissy femboy makes chastity content and streams on chaturbate

Sissy femboy makes chastity content and streams on chaturbate

BigTitsLust 1 year ago

Unmerciful Dommes Vigour Sissy Serf to Gulp Down Week-Old Cum Loads

Unmerciful Dommes Vigour Sissy Serf to Gulp Down Week-Old Cum Loads

Amateur8 1 year ago

Peg Curious - Sharing My Man W Roommate

76% 0:39 / 26:10

Peg Curious - Sharing My Man W Roommate

FapHouse 1 week ago

Redhead Mistress destroys sissy with massive strap-on rough pegging training

Redhead Mistress destroys sissy with massive strap-on rough pegging training

NewBestPorn 2 weeks ago

Viky & Mateo Private Show

60% HD 2:00 / 11:05

Viky & Mateo Private Show

Flirt4Free 5 months ago

Zoe Gray Private Show

HD 2:00 / 14:37

Zoe Gray Private Show

Camster 1 year ago

Eye-Contact Pegging JOI Sissification POV – I Make My Sissy Princess Cum Like a Fine Gal

Eye-Contact Pegging JOI Sissification POV – I Make My Sissy Princess Cum Like a Fine Gal

FreePorn8 1 year ago

Miss Alessa Milano Sissy Bitch Blowjob Strapon Feed Used Condoms Part 2

58% HD 0:39 / 10:23

Miss Alessa Milano Sissy Bitch Blowjob Strapon Feed Used Condoms Part 2

FapHouse 1 year ago

Princess Sissy Training, Chastity and Worship

Princess Sissy Training, Chastity and Worship

Itsrealamateurs 4 weeks ago

Suck His Dick Loser

Suck His Dick Loser

XHamster 1 year ago

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 years ago

Sissy Slut's Progess Goddess Brianna

50% HD 1:01 / 7:44

Sissy Slut's Progess Goddess Brianna

FapHouse 2 years ago

Sissy Compilation Chastity Forever

Sissy Compilation Chastity Forever

Lesbian8 1 month 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

Her femboy stands and flows like a whore

Her femboy stands and flows like a whore

XHamster 3 years ago

Machine Fucks Sissy While I Sit on her Face then Peg her

71% HD 0:21 / 27:39

Machine Fucks Sissy While I Sit on her Face then Peg her

Clips4sale 1 year ago

Facesitters in Heat vol 18

Facesitters in Heat vol 18

XHamster 8 months ago

My Loser Beta Sissy Cuckold Jason

My Loser Beta Sissy Cuckold Jason

XHamster 3 months ago

Jen Holly Private Show

HD 2:00 / 17:38

Jen Holly Private Show

Camster 1 year ago

Two Dominatrix Femdom Ritual Humiliates Sissy Slave With Fierce French Pegging and Ballbusting

Two Dominatrix Femdom Ritual Humiliates Sissy Slave With Fierce French Pegging and Ballbusting

Juicexxx 3 days ago

Bella Brookz Private Show

46% HD 2:00 / 12:38

Bella Brookz Private Show

Flirt4Free 3 years ago

Bye Bye Vagina

MatureTubeHere 4 years ago

Sissy Slut made ready for Mistress (1080p)

HD 0:13 / 12:18

Sissy Slut made ready for Mistress (1080p)

Clips4sale 3 weeks ago

Bella Brookz Private Show

57% HD 2:00 / 9:01

Bella Brookz Private Show

Flirt4Free 3 years ago

Jhanne Cherry Private Show

55% HD 2:00 / 8:06

Jhanne Cherry Private Show

Flirt4Free 10 months ago

Bimbo Magic Spell

Bimbo Magic Spell

XHamster 2 months ago

INSTITUTION X - Prostate Milking Anal Training Pspot Orgasm COMPILATION 2-2

INSTITUTION X - Prostate Milking Anal Training Pspot Orgasm COMPILATION 2-2

Pornfact 1 week ago

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