Sissy Training Porn (147,125)

Bi Humiliation & Cum Clean up with a Female Audience

49% 1:01 / 8:42

Bi Humiliation & Cum Clean up with a Female Audience

FapHouse 1 year ago

Gentle Bi Encouragement - Will You Suck Cock For Me?

Gentle Bi Encouragement - Will You Suck Cock For Me?

XHamster 1 year ago

Sissy & cuckold training

52% HD 1:01 / 11:51

Sissy & cuckold training

FapHouse 5 years ago

Cum Task for Bi-boys Encouraged Bi Cum Swallowers Femdom

63% HD 1:01 / 5:37

Cum Task for Bi-boys Encouraged Bi Cum Swallowers Femdom

FapHouse 7 months ago

Suck Cock and Swallow Hot Cum - Obey Your Mistress

Suck Cock and Swallow Hot Cum - Obey Your Mistress

XHamster 1 year ago

Good boys eat cum

Good boys eat cum

XHamster 1 year 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

PROSTATE EXPLOSION big compilation

PROSTATE EXPLOSION big compilation

XHamster 2 years 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

Amber Fletcher Private Show

60% HD 2:00 / 5:11

Amber Fletcher Private Show

Camster 1 year ago

Jasmine Flowers Pegging Training, femdom Goddess

64% 1:01 / 17:29

Jasmine Flowers Pegging Training, femdom Goddess

FapHouse 1 week ago

Real cuckold wife wants to suck cock together !!!

Real cuckold wife wants to suck cock together !!!

XHamster 7 months ago

Not for Boring Couples - Vol 2

Not for Boring Couples - Vol 2

FapHouse 3 weeks 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

Peg Curious - Sharing My Man W Roommate

57% 1:01 / 26:10

Peg Curious - Sharing My Man W Roommate

FapHouse 3 weeks ago

Bi Encouragement - Serve Me and Alpha Cock

51% HD 1:01 / 12:47

Bi Encouragement - Serve Me and Alpha Cock

FapHouse 7 months ago

Tormenting My Cuck! Cruel Femdom POV

63% HD 1:01 / 20:05

Tormenting My Cuck! Cruel Femdom POV

FapHouse 1 week ago

Suck His Dick Loser

Suck His Dick Loser

XHamster 1 year 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

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

Sexy Wife with Big Strapon pegging her Husband with Handjob

Sexy Wife with Big Strapon pegging her Husband with Handjob

XHamster 1 year ago

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

69% 0:39 / 11:41

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

FapHouse 5 months ago

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

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

BigTitsLust 1 week ago

Sissy Training- Blowjob CEI HYP

Sissy Training- Blowjob CEI HYP

Eporner 2 months ago

Confess that you are a sissy to your best friend!

Confess that you are a sissy to your best friend!

XHamster 1 week 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 1 year ago

Feel My Power

66% HD 0:39 / 4:02

FapHouse 2 years ago

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

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

SortPorn 1 week ago

Bella Brookz Private Show

HD 2:00 / 22:41

Bella Brookz Private Show

Camster 2 years ago

Husband Gets Sissified

58% HD 0:10 / 26:36

Husband Gets Sissified

LoyalFans 3 months ago

Sissy Training in Chastity

56% HD 0:39 / 9:54

Sissy Training in Chastity

FapHouse 1 year ago

Training You, My Sissy, to Love Cock

62% HD 0:10 / 10:14

Training You, My Sissy, to Love Cock

LoyalFans 3 weeks ago

Genitalia haircut & edging for chastity slave

Genitalia haircut & edging for chastity slave

XHamster 1 year 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

Sharon J Private Show

Sharon J Private Show

Camster 2 weeks ago

Alpha Couple Teaches How to Suck Cock

61% HD 0:39 / 11:53

Alpha Couple Teaches How to Suck Cock

FapHouse 1 year ago

Peg Curious - Sharing My Man W Roommate

Peg Curious - Sharing My Man W Roommate

XHamster 3 weeks ago

Bikini Obsessed Sissy

Bikini Obsessed Sissy

LoyalFans 3 weeks ago

Sunday Humiliation for Sissy husband Full

Sunday Humiliation for Sissy husband Full

XHamster 1 year ago

Wife Fists Husband Nearly Elbow Deep

54% 1:01 / 8:58

Wife Fists Husband Nearly Elbow Deep

FapHouse 2 years ago

FILIPINA DOMINATRIX PEGGING WHITE CHASTITY SLAVE

FILIPINA DOMINATRIX PEGGING WHITE CHASTITY SLAVE

XHamster 4 years ago

Cuckold Fantasies Volume 20

Cuckold Fantasies Volume 20

XHamster 4 years ago

Obedient White Whore Worships BBC & Dicked down Hard

Obedient White Whore Worships BBC & Dicked down Hard

FreePorn8 4 years ago

Hardcore Up Close Femdom Bi Encouragement Oral job and CEI

Hardcore Up Close Femdom Bi Encouragement Oral job and CEI

Dafreeporn 3 years ago

bi confusion swallow his cum sissy faggot CEI (point of view cumshot femdom training)

bi confusion swallow his cum sissy faggot CEI (point of view cumshot femdom training)

Itsrealamateurs 4 days ago

$let\'s get naughty - Part 2$ 4K 2:00 / 4:52

let\'s get naughty - Part 2

Camster 3 days ago

PROSTATE ORGASM COMPILATION SISSY

PROSTATE ORGASM COMPILATION SISSY

XHamster 4 years ago

Size Queen Sissy Male Training with CEI

Size Queen Sissy Male Training with CEI

BigTitsLust 5 days ago

Sissy is filled with 100cm extrem dildo - part 2 of 2

Sissy is filled with 100cm extrem dildo - part 2 of 2

XHamster 2 years ago

i made my little sissy have a chastity orgasm

i made my little sissy have a chastity orgasm

XHamster 5 months ago

Long and Hard Pegging with a big dildo – Topped Toys Mordax 90

Long and Hard Pegging with a big dildo – Topped Toys Mordax 90

XHamster 4 years ago

Jhanne Cherry Private Show

49% 4K 2:00 / 22:26

Jhanne Cherry Private Show

Flirt4Free 1 year 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

Sissy Dresses Up - Strap-on POV

56% HD 0:10 / 7:11

Sissy Dresses Up - Strap-on POV

LoyalFans 2 weeks ago

The Sissygasm

57% 0:39 / 12:01

FapHouse 1 year ago

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

54% HD 0:39 / 12:35

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

FapHouse 5 months ago

Mistress training sissies to play together

Mistress training sissies to play together

AbXXX 7 years ago

Khloe Clark Private Show

49% 4K 2:00 / 24:07

Khloe Clark Private Show

Camster 4 weeks ago

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

64% 1:00 / 10:13

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

Clips4sale 1 year ago

Whoring Out The Sissy Bimbo

55% HD 0:10 / 9:17

Whoring Out The Sissy Bimbo

LoyalFans 4 years ago

Submissive Sluts volume 4

Submissive Sluts volume 4

XHamster 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

V gets his urethra stretched with larger and larger sounds, then I plug it with a 12mm and squeeze his balls hard

V gets his urethra stretched with larger and larger sounds, then I plug it with a 12mm and squeeze his balls hard

XHamster 2 years 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 1 week ago

Bi Encouragement Training - Take 2 Of My Mans Cumshots

Bi Encouragement Training - Take 2 Of My Mans Cumshots

XHamster 1 week ago

Sissy Huren Ausbildung Incl Sperma schlucken (deutsch) /Sissy Hure Training, including to swallow sperm (german)

54% HD 0:10 / 13:14

Sissy Huren Ausbildung Incl Sperma schlucken (deutsch) /Sissy Hure Training, including to swallow sperm (german)

LoyalFans 3 years ago

Sissy Academy Part 6 - Sissy's Taste of Heaven

62% HD 1:01 / 5:55

Sissy Academy Part 6 - Sissy's Taste of Heaven

FapHouse 1 month ago

Asian Hotwife Turns Husband Into a Cum-eating Cuck

Asian Hotwife Turns Husband Into a Cum-eating Cuck

XHamster 3 months ago

Grisha Mochka Private Show

73% 4K 2:00 / 19:56

Grisha Mochka Private Show

Camster 3 weeks ago

BBC Creampie Cuckold Couple Trained for Pleasure

BBC Creampie Cuckold Couple Trained for Pleasure

Jizzberry 5 years ago

Cum Eating instruction CEI #1 By Bestsissycaptions

Cum Eating instruction CEI #1 By Bestsissycaptions

Amateur8 2 years ago

Lady Caitlyn Party on Jun 30, 2026

47% HD 2:00 / 1:00:18

Lady Caitlyn Party on Jun 30, 2026

Camster 2 weeks ago

A Sissy Fantasy

HD 0:25 / 13:42

A Sissy Fantasy

IWantClips 8 months ago

Step-sister Gets off Humiliating You Taboo Femdom POV

HD 0:39 / 22:58

Step-sister Gets off Humiliating You Taboo Femdom POV

FapHouse 5 days ago

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

59% HD 0:39 / 16:47

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

FapHouse 2 weeks ago

Bedtime Strap-on Service (taker POV)

Bedtime Strap-on Service (taker POV)

FapHouse 8 months ago

Your Wife Pegs You - Male POV

61% VR 0:08 / 3:00

Your Wife Pegs You - Male POV

FapHouse 8 months ago

Sissy Panty Slut Sph JOI

Sissy Panty Slut Sph JOI

XHamster 2 months ago

Sissy In Pink Gets Cock-Trained

59% HD 0:10 / 22:42

Sissy In Pink Gets Cock-Trained

LoyalFans 3 months ago

A Sissy Care Day - Task, Chastity, Butt Plug, Dildo

HD 1:01 / 10:37

A Sissy Care Day - Task, Chastity, Butt Plug, Dildo

FapHouse 1 year 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 2 years ago

Evil big beautiful woman Domina Destroys Stepson CBT Boots, Unfathomable Gagging, Anal Stretching, Sissification and Void urine Drinking!

Evil big beautiful woman Domina Destroys Stepson CBT Boots, Unfathomable Gagging, Anal Stretching, Sissification and Void urine Drinking!

SortPorn 2 weeks ago

1 hr ULTIMATE PEGGING Compilation

HD 0:25 / 58:37

1 hr ULTIMATE PEGGING Compilation

IWantClips 6 years ago

8 INCH Strapon fucking my chastity slut in Latex

8 INCH Strapon fucking my chastity slut in Latex

XHamster 3 years ago

BBW Femdom - Pegging Chaste Sissy Anal

BBW Femdom - Pegging Chaste Sissy Anal

XHamster 1 year ago

Throat Fuck Training with Miss Katie

Throat Fuck Training with Miss Katie

XHamster 4 days ago

Making Him My Sissy Whore by Dominafire

Making Him My Sissy Whore by Dominafire

FapHouse 2 years ago

FULL LIVE - Sissification Slumber Party & Beta Bullying - Featuring Goddess Jay

54% HD 0:10 / 2:40:24

FULL LIVE - Sissification Slumber Party & Beta Bullying - Featuring Goddess Jay

LoyalFans 5 months ago

My Loser Beta Sissy Cuckold Jason

My Loser Beta Sissy Cuckold Jason

XHamster 4 months ago

Jennas Suprise

XHamster 2 years ago

Suck Wang For Your Mastix - Bi Encouragement

Suck Wang For Your Mastix - Bi Encouragement

Amateur8 1 year ago

Abril Newton Private Show

58% HD 2:00 / 16:26

Abril Newton Private Show

Flirt4Free 11 months ago

Latex Sissy Pegged by Filipina Dominatrix

56% HD 1:01 / 9:15

Latex Sissy Pegged by Filipina Dominatrix

FapHouse 4 years ago

Viky & Mateo Private Show

66% HD 2:00 / 4:48

Viky & Mateo Private Show

Camster 6 months ago

Making My Slaves Moan Pegging Triptych Montage

Making My Slaves Moan Pegging Triptych Montage

IWantClips 2 years ago

Ruth Oliver Private Show

59% 4K 2:00 / 18:06

Ruth Oliver Private Show

Flirt4Free 1 month ago

Making You Soft Forever

61% HD 0:28 / 19:00

Making You Soft Forever

IWantClips 10 months ago

BBC Takes My Tight Pussy Deeper Than Ever - Ali Uchiha Senju

BBC Takes My Tight Pussy Deeper Than Ever - Ali Uchiha Senju

XXXShake 3 years ago

can you make me cumm ?? - Part 2

61% 4K 2:00 / 4:52

can you make me cumm ?? - Part 2

Camster 3 weeks ago

Julie and Liza's Latex Doll

65% HD 0:10 / 19:56

Julie and Liza's Latex Doll

LoyalFans 5 months ago

FEMDOM SISSY PEGGING ANAL CUM EATING BIG TITS STRAPON CUMSHOT

FEMDOM SISSY PEGGING ANAL CUM EATING BIG TITS STRAPON CUMSHOT

XHamster 5 months ago

INSTITUTION X - Prostate Milking Butthole Training Pspot Cumming COMPILATION 1-2

INSTITUTION X - Prostate Milking Butthole Training Pspot Cumming COMPILATION 1-2

KAMS 1 year ago

Premature Ruined Orgasms for chastity slave

Premature Ruined Orgasms for chastity slave

XHamster 3 months ago

Vends-ta-culotte - Gorgeous French dominatrix punishes your ass because you weren't obedient enoug

Vends-ta-culotte - Gorgeous French dominatrix punishes your ass because you weren't obedient enoug

XHamster 3 months ago

Angelica Swiss Party on Jul 4, 2026 - Part 3

HD 2:00 / 29:10

Angelica Swiss Party on Jul 4, 2026 - Part 3

Camster 2 weeks ago

ASMR sloppy caged cuck chastity cum (locktober final reward)

ASMR sloppy caged cuck chastity cum (locktober final reward)

XHamster 2 years ago

Sweet & Daaniel Private Show

63% HD 2:00 / 14:05

Sweet & Daaniel Private Show

Camster 4 weeks ago

Learn To Curtsey For Men

Learn To Curtsey For Men

Clips4sale 3 years ago

Isadora Dunkan Private Show

Isadora Dunkan Private Show

Camster 2 days ago

JOI Echo With My Big Black Dick - Luna Doll

JOI Echo With My Big Black Dick - Luna Doll

XHamster 9 months ago

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

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

Amateur8 6 days ago

Emily & Stesha Private Show

53% 4K 2:00 / 5:57

Emily & Stesha Private Show

Flirt4Free 6 months ago

GIGANTIC Ding-dong Pegging with Bad Dragon and Hankey for Lewd Sissy Wench by Mistresse Mercer

GIGANTIC Ding-dong Pegging with Bad Dragon and Hankey for Lewd Sissy Wench by Mistresse Mercer

Amateur8 7 months ago

Reven Mayers Private Show

HD 2:00 / 25:58

Reven Mayers Private Show

Camster 1 day ago

Beta Male Training Initiation

HD 0:10 / 34:22

Beta Male Training Initiation

LoyalFans 2 weeks ago

DOMINATRIX PEGGING CHASTITY FAGGOT

DOMINATRIX PEGGING CHASTITY FAGGOT

XHamster 2 years ago

Elizabeth Whiler Private Show

60% HD 2:00 / 13:22

Elizabeth Whiler Private Show

Camster 3 years ago

Bimbo Bible Vol 3: Gaping Anal Slut (480 MP4)

66% HD 0:30 / 13:08

Bimbo Bible Vol 3: Gaping Anal Slut (480 MP4)

Clips4sale 3 years ago

Do You Want to be My Girl, Sissy?

58% 0:11 / 7:20

Do You Want to be My Girl, Sissy?

Clips4sale 2 years ago

Sissy Academy Part 1

Sissy Academy Part 1

XHamster 9 months ago

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