Sissy Training - Sex Videos (146,928)

Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

56% 0:39 / 20:13

Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

FapHouse 1 year ago

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

Suck Cock and Swallow Hot Cum - Obey Your Mistress

Suck Cock and Swallow Hot Cum - Obey Your Mistress

XHamster 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

59% HD 0:39 / 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

Ruined Orgasm Scene From Hospital 1

63% HD 0:39 / 5:25

Ruined Orgasm Scene From Hospital 1

FapHouse 1 year ago

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

HD 1:01 / 16:47

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

FapHouse 1 week ago

Rubber Sissy Doll in Training

69% HD 0:10 / 12:45

Rubber Sissy Doll in Training

LoyalFans 1 month ago

Peg Curious - Sharing My Man W Roommate

76% 0:39 / 26:10

Peg Curious - Sharing My Man W Roommate

FapHouse 1 week ago

Lady Caitlyn Party on Jun 30, 2026

52% HD 2:00 / 1:00:18

Lady Caitlyn Party on Jun 30, 2026

Camster 1 week ago

Training You, My Sissy, to Love Cock

55% HD 0:10 / 10:14

Training You, My Sissy, to Love Cock

LoyalFans 2 weeks ago

Dressing up Sissy

61% HD 0:39 / 10:15

Dressing up Sissy

FapHouse 1 year ago

Sissy Whore Training With Chasity & Essential Oils

57% HD 0:10 / 17:53

Sissy Whore Training With Chasity & Essential Oils

LoyalFans 3 weeks 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

Positive Femdom: Pegging, Fisting to Each Other, Pee. Arya Grander

Positive Femdom: Pegging, Fisting to Each Other, Pee. Arya Grander

XHamster 1 year ago

Bisexual husband gets fucked by three strapons

Bisexual husband gets fucked by three strapons

XHamster 2 years ago

PROSTATE EXPLOSION big compilation

PROSTATE EXPLOSION big compilation

XHamster 2 years ago

Sissy Training - Teaching My Friend How to Give a Blowjob

66% HD 1:01 / 29:53

Sissy Training - Teaching My Friend How to Give a Blowjob

FapHouse 1 year ago

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

50% HD 0:39 / 11:28

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

FapHouse 3 weeks ago

Zoey Evans Premiere Show

HD 2:00 / 10:19

Zoey Evans Premiere Show

Camster 1 week ago

Cuckold Fantasies Volume 20

Cuckold Fantasies Volume 20

XHamster 4 years ago

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

71% 0:39 / 11:41

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

FapHouse 5 months ago

Slutty & Submissive Amateur Gets Used Like a Fuck Toy

61% 0:39 / 3:38

Slutty & Submissive Amateur Gets Used Like a Fuck Toy

FapHouse 4 months ago

Katharine Cane Party on Jul 4, 2026 - Part 2

55% HD 2:00 / 50:15

Katharine Cane Party on Jul 4, 2026 - Part 2

Camster 4 days ago

Feel My Power

66% HD 0:39 / 4:02

FapHouse 2 years 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

53% 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

Gentle Bi Encouragement - Will You Suck Cock For Me?

Gentle Bi Encouragement - Will You Suck Cock For Me?

XHamster 1 year ago

Son Sent Away to Goddess Snow for Proper Sissy Training

Son Sent Away to Goddess Snow for Proper Sissy Training

HD21 5 months ago

Genitalia haircut & edging for chastity slave

Genitalia haircut & edging for chastity slave

XHamster 1 year ago

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

50% HD 1:01 / 19:18

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

FapHouse 6 months ago

Sexy Asian Mistress Dominates You

Sexy Asian Mistress Dominates You

FapHouse 1 week ago

Sissy Blowjob Training by Mistress Dominafire

Sissy Blowjob Training by Mistress Dominafire

FapHouse 2 years ago

Kissed And Pounded

55% HD 0:10 / 10:01

Kissed And Pounded

LoyalFans 2 years ago

Khloe Clark Private Show

49% 4K 2:00 / 24:07

Khloe Clark Private Show

Camster 2 weeks ago

Faggot Maker - make me bi - bi encouragement - CEI - cock worship - faggot training - sissy training - imposed bi - big cock - joi

58% HD 0:10 / 6:32

Faggot Maker - make me bi - bi encouragement - CEI - cock worship - faggot training - sissy training - imposed bi - big cock - joi

LoyalFans 1 year ago

Abril Newton Private Show

55% HD 2:00 / 19:22

Abril Newton Private Show

Flirt4Free 10 months ago

Caged Sissy Cuckold Gaming - Mistress Gives Slave in Chastity a Handjob with Ruined Orgasm

52% HD 0:39 / 12:35

Caged Sissy Cuckold Gaming - Mistress Gives Slave in Chastity a Handjob with Ruined Orgasm

FapHouse 5 months ago

Girls Day Out

Clips4sale 1 month ago

Playing with My Husband's Asshole

Playing with My Husband's Asshole

XHamster 2 years ago

Mean femdom Flagellation Treatment

Mean femdom Flagellation Treatment

Some.Porn 1 year ago

JOI CEI Anal - Be My Best Sissy with Your Best Heels and Fuck Your Ass with a Dildo

HD 0:39 / 15:05

JOI CEI Anal - Be My Best Sissy with Your Best Heels and Fuck Your Ass with a Dildo

FapHouse 2 months ago

Pissing CFNM domina punishes sissy in BDSM lesson

Pissing CFNM domina punishes sissy in BDSM lesson

Some.Porn 1 year ago

He's been asking for so long. I saw for the first time what a male anal orgasm is.

He's been asking for so long. I saw for the first time what a male anal orgasm is.

XHamster 4 years ago

Sissy-academy Part 1 - Sissys Chastity

62% HD 0:39 / 5:11

Sissy-academy Part 1 - Sissys Chastity

FapHouse 1 month 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

The Secret of My Body

58% 2:00 / 5:16

The Secret of My Body

Flirt4Free 5 months ago

Bi Humiliation & Cum Clean up with a Female Audience

45% 0:39 / 8:42

Bi Humiliation & Cum Clean up with a Female Audience

FapHouse 1 year 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 2 years ago

Sissy trained to swallow all the cum

53% 4K 0:16 / 7:44

Sissy trained to swallow all the cum

Clips4sale 2 years ago

Sissy Wife Pegged In Chastity - Clara Dee POV

Sissy Wife Pegged In Chastity - Clara Dee POV

XHamster 2 years ago

Aurora Ber Private Show

50% 4K 2:00 / 6:07

Aurora Ber Private Show

Flirt4Free 10 months ago

Gala Smith Private Show

Gala Smith Private Show

Camster 6 days ago

Hardcore Up Close Femdom Bi Encouragement Oral Sex and CEI

Hardcore Up Close Femdom Bi Encouragement Oral Sex and CEI

Amateur8 3 years ago

Mistress training sissies to play together

Mistress training sissies to play together

AbXXX 6 years ago

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 4 years ago

Mistresst - High Class Sissy Trained

Mistresst - High Class Sissy Trained

InPorn 4 years ago

The Last Step: Convincing You to Become My Feminized Cocksucker

The Last Step: Convincing You to Become My Feminized Cocksucker

XHamster 1 month ago

Isadora Dunkan Private Show

Isadora Dunkan Private Show

Camster 1 week ago

FEMDOM & SISSY PEGGING HOT SHOTS & CUMSHOTS COMPILATION

FEMDOM & SISSY PEGGING HOT SHOTS & CUMSHOTS COMPILATION

Lesbian8 10 months ago

anal training sissy faggot femdom strapon hard fucks slave's ass makes him eat own cum CEI

anal training sissy faggot femdom strapon hard fucks slave's ass makes him eat own cum CEI

StiefMutter 4 days ago

Alphapaar Cuckold und Zahlsissy

Alphapaar Cuckold und Zahlsissy

Clips4sale 1 month ago

Cum Eating instruction CEI #1 By Bestsissycaptions

Cum Eating instruction CEI #1 By Bestsissycaptions

Amateur8 1 year ago

How to bring a guy to a double orgasm

How to bring a guy to a double orgasm

XHamster 3 years ago

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

62% HD 1:01 / 11:28

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

FapHouse 3 weeks ago

Best of Harmony Rose Volume 1

Best of Harmony Rose Volume 1

XHamster 4 years ago

Sissy Training- Blowjob CEI HYP

Sissy Training- Blowjob CEI HYP

Eporner 2 months ago

Sissy Academy Part 1

Sissy Academy Part 1

XHamster 9 months ago

Tepid Tea Torment, spanking, tawsing and dressage cropping the Butler for mediocre service

55% 4K 0:26 / 8:04

Tepid Tea Torment, spanking, tawsing and dressage cropping the Butler for mediocre service

Clips4sale 1 year ago

Camilla Polls Private Show

46% 4K 2:00 / 6:56

Camilla Polls Private Show

Camster 2 weeks ago

Top 10 Chastity Ideas Vol.2

Top 10 Chastity Ideas Vol.2

XHamster 7 months ago

Kendra in Control - Part 1 of 7

HD 0:39 / 10:06

Kendra in Control - Part 1 of 7

FapHouse 4 days ago

Matriarch Ezada Sinn fucks him up the arse and makes him eat his own cum from Her strap-on

61% HD 0:10 / 17:20

Matriarch Ezada Sinn fucks him up the arse and makes him eat his own cum from Her strap-on

LoyalFans 1 year ago

Femdom POV Sissy Training Pleasure Him

51% HD 1:01 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 3 months ago

Electro Sissy Begs to Cum

HD 0:10 / 10:11

Electro Sissy Begs to Cum

LoyalFans 1 year ago

Abril Newton Private Show

57% 4K 2:00 / 11:48

Abril Newton Private Show

Camster 11 months ago

Adrenaline on the Train. Caught in the Toilet

Adrenaline on the Train. Caught in the Toilet

XHamster 2 months ago

Miss Alessa Milano Blowjob Lesson

57% 1:01 / 8:55

Miss Alessa Milano Blowjob Lesson

FapHouse 1 year ago

ASMR sloppy caged cuck chastity cum (locktober final reward)

ASMR sloppy caged cuck chastity cum (locktober final reward)

XHamster 2 years ago

Viky & Mateo Private Show

62% HD 2:00 / 19:22

Viky & Mateo Private Show

Flirt4Free 6 months ago

Isadora Dunkan Private Show

65% 4K 2:00 / 10:17

Isadora Dunkan Private Show

Camster 6 days ago

Submissive Sluts volume 4

Submissive Sluts volume 4

XHamster 5 days ago

【Sample】Tickling 10.　sisification, sissy training

【Sample】Tickling 10.　sisification, sissy training

Pornzona 2 weeks ago

Sissy Bitch Pegging Compilation. Femdom Chastity

Sissy Bitch Pegging Compilation. Femdom Chastity

BigTitsLust 2 years ago

Creating A New Feminized Doll (WMV)

70% 0:13 / 59:30

Creating A New Feminized Doll (WMV)

Clips4sale 10 months ago

Wife Fucks Husband Like a Submissive Sissy Pegging Rimming #68 Part 1

Wife Fucks Husband Like a Submissive Sissy Pegging Rimming #68 Part 1

XHamster 2 years ago

wife makes stranger cum and then her husband licks it up

wife makes stranger cum and then her husband licks it up

XHamster 1 year ago

Brunette and Chastity slave having some fun

Brunette and Chastity slave having some fun

XHamster 1 year ago

Sissy Dress-up Encouragement

55% HD 0:39 / 9:19

Sissy Dress-up Encouragement

FapHouse 4 months ago

Cum Eating instruction CEI #1 By Bestsissycaptions

Cum Eating instruction CEI #1 By Bestsissycaptions

FreePorn8 1 year ago

Best of Harmony Rose vol 2

Best of Harmony Rose vol 2

XHamster 1 year ago

Stepmommy Turns U into a Little Bunny Sissy Wench - Penny Barber Taboo

Stepmommy Turns U into a Little Bunny Sissy Wench - Penny Barber Taboo

Lesbian8 5 months ago

Asian Hotwife Turns Husband Into a Cum-eating Cuck

Asian Hotwife Turns Husband Into a Cum-eating Cuck

XHamster 3 months ago

Fooled and Unfortunately No Orgasm

Fooled and Unfortunately No Orgasm

XHamster 10 months ago

The Final Transformation Part 2

The Final Transformation Part 2

Dafreeporn 3 months ago

POV Sissy Pegging - Custom for FRED

POV Sissy Pegging - Custom for FRED

Amateur8 4 years ago

Sissy Transformation Training – Miss Lilly & Sir Claire Turn You Into Their Pretty Doll and Footstool

64% HD 0:10 / 15:54

Sissy Transformation Training – Miss Lilly & Sir Claire Turn You Into Their Pretty Doll and Footstool

LoyalFans 4 months ago

BBC Creampie Cuckold Couple Trained for Pleasure

BBC Creampie Cuckold Couple Trained for Pleasure

Jizzberry 5 years ago

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 7 months ago

Zoey Evans Premiere Show

HD 2:00 / 10:19

Zoey Evans Premiere Show

Flirt4Free 1 week ago

Good boys eat cum

Good boys eat cum

XHamster 1 year ago

Guided JOI Session With Femdom Mistress

Guided JOI Session With Femdom Mistress

Pornicom 4 years ago

Suck Wang For Your Mastix - Bi Encouragement

Suck Wang For Your Mastix - Bi Encouragement

Amateur8 1 year ago

Sandra Angell Private Show - Part 3

51% HD 2:00 / 43:27

Sandra Angell Private Show - Part 3

Flirt4Free 2 years ago

Prissy sissy dolly - Maid to be used

63% 0:30 / 13:35

Prissy sissy dolly - Maid to be used

Clips4sale 1 year ago

GAGGING ON LESBIAN COCK

48% HD 0:10 / 7:51

GAGGING ON LESBIAN COCK

LoyalFans 3 years ago

We Love Spreading and Playing with Our Big Asses.

We Love Spreading and Playing with Our Big Asses.

XHamster 1 month ago

Grisha Mochka Private Show

71% 4K 2:00 / 19:56

Grisha Mochka Private Show

Camster 1 week ago

Mommy Stuffs Your Ass With a Remote Butt Plug & Edges Your Tiny Locked Clit

HD 0:10 / 17:45

Mommy Stuffs Your Ass With a Remote Butt Plug & Edges Your Tiny Locked Clit

LoyalFans 3 months ago

... - Part 3

55% 4K 2:00 / 4:53

Camster 2 weeks ago

Julie and Liza's Latex Doll

64% HD 0:10 / 19:56

Julie and Liza's Latex Doll

LoyalFans 5 months ago

Hotwife Date from the Cuckolds Point of View

Hotwife Date from the Cuckolds Point of View

XHamster 2 years ago

Chastity and Nipples Tease (iPhone)

Chastity and Nipples Tease (iPhone)

Clips4sale 1 year ago

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

45% HD 1:01 / 18:20

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

FapHouse 2 months ago

Zoey Evans Party on Jul 5, 2026 - Part 3

HD 2:00 / 2:53:15

Zoey Evans Party on Jul 5, 2026 - Part 3

Camster 4 days ago

Wife Makes Husband Suck Her Lovers Cock Whilst She Masturbates

60% 0:39 / 6:57

Wife Makes Husband Suck Her Lovers Cock Whilst She Masturbates

FapHouse 11 months ago

Femdom Dungeon Private Party Part 2 of 5: Locked up in Chastity, Humbler, CBT, Anal Training with Mistress Stellina Obscura (1080p)

66% HD 0:30 / 10:40

Femdom Dungeon Private Party Part 2 of 5: Locked up in Chastity, Humbler, CBT, Anal Training with Mistress Stellina Obscura (1080p)

Clips4sale 1 year ago

Sissy Jennas Deepthroat Training

Sissy Jennas Deepthroat Training

XHamster 2 weeks ago

$let\'s have some fun - Part 2$ 4K 2:00 / 4:52

let\'s have some fun - Part 2

Camster 2 weeks ago

Jhanne Cherry Private Show

55% HD 2:00 / 8:06

Jhanne Cherry Private Show

Flirt4Free 10 months ago

Mommy Fucks your ass and makes you Cum on your Face POV

Mommy Fucks your ass and makes you Cum on your Face POV

Pornzona 1 week ago

Vina Belle Private Show

HD 2:00 / 1:33:00

Vina Belle Private Show

Camster 4 days ago

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