Sissy Training - Sex Videos (154,922)

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 year ago

Cuckold Fantasies Volume 20

Cuckold Fantasies Volume 20

XHamster 5 years 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 2 years ago

Sissy Cumslut for Asian Homewrecker CEI

53% HD 0:29 / 19:57

Sissy Cumslut for Asian Homewrecker CEI

IWantClips 1 year ago

Amateur Huge Strap-on Pegging Session

HD 0:39 / 20:52

Amateur Huge Strap-on Pegging Session

FapHouse 1 week ago

Peg Curious - Sharing My Man W Roommate

71% 0:39 / 26:10

Peg Curious - Sharing My Man W Roommate

FapHouse 3 months ago

Viky & Mateo Private Show

55% HD 2:00 / 11:13

Viky & Mateo Private Show

Flirt4Free 8 months ago

Jhanne Cherry Private Show

52% HD 2:00 / 8:06

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Angelica Swiss Party on Oct 21, 2025

65% 4K 2:00 / 2:03:16

Angelica Swiss Party on Oct 21, 2025

Flirt4Free 11 months ago

Spanking My Sissybitch

Spanking My Sissybitch

XHamster 3 days ago

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 year ago

Extreme Anal Challenge - Strapon and 15-inch Dildo Until He Takes It All and Cums on My Black Nitrile Gloves

59% 1:01 / 20:06

Extreme Anal Challenge - Strapon and 15-inch Dildo Until He Takes It All and Cums on My Black Nitrile Gloves

FapHouse 1 month ago

Genitalia haircut & edging for chastity slave

Genitalia haircut & edging for chastity slave

XHamster 1 year ago

Elizabeth Whiler Private Show

51% HD 2:00 / 13:22

Elizabeth Whiler Private Show

Flirt4Free 4 years ago

Step-mommy's Forever 2

58% 1:01 / 34:34

Step-mommy's Forever 2

FapHouse 1 month ago

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 month ago

Alessia Lacroix Private Show

HD 2:00 / 17:14

Alessia Lacroix Private Show

Flirt4Free 1 month ago

JOI Sissy - Be My Dirty Little Bitch

63% HD 1:01 / 11:29

JOI Sissy - Be My Dirty Little Bitch

FapHouse 3 months ago

Jhanne Cherry Private Show

48% HD 2:00 / 22:11

Jhanne Cherry Private Show

Flirt4Free 1 year 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

Suck Cock and Swallow Hot Cum - Obey Your Mistress

Suck Cock and Swallow Hot Cum - Obey Your Mistress

XHamster 1 year ago

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 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 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

Blonde femdom trains a sissy in latex and heels inside a sleek German dungeon

Blonde femdom trains a sissy in latex and heels inside a sleek German dungeon

Yesvids 2 months ago

$Katharine Kane\'s Handcuffed Blowjob$ 64% HD 2:00 / 19:35

Katharine Kane\'s Handcuffed Blowjob

Flirt4Free 9 years ago

Group Bi Training with My Three Girlfriends

Group Bi Training with My Three Girlfriends

XHamster 3 months ago

Sissy Gets Milked with a Plug in Her Ass and Has to Swallow Cum

60% 1:01 / 17:18

Sissy Gets Milked with a Plug in Her Ass and Has to Swallow Cum

FapHouse 1 month ago

Cuckold 2 (lick My Toilet Clean!)

59% HD 0:39 / 5:36

Cuckold 2 (lick My Toilet Clean!)

FapHouse 1 year ago

Slut Training for Slaves

Slut Training for Slaves

FapHouse 1 month ago

Goddess Sissy Training Penis Worshiper CEI

Goddess Sissy Training Penis Worshiper CEI

ALOTPorn 4 years ago

Emily & Stesha Private Show

4K 2:00 / 12:14

Emily & Stesha Private Show

Flirt4Free 5 months ago

Give up Your Life to Serve Me

HD 0:39 / 11:39

Give up Your Life to Serve Me

FapHouse 1 month ago

Real cuckold wife wants to suck cock together !!!

Real cuckold wife wants to suck cock together !!!

XHamster 9 months ago

Mistress training sissies to play together

Mistress training sissies to play together

AbXXX 7 years ago

The Lust of Sissy 3D Saga - Supportive Sugardaddy

49% HD 0:39 / 12:03

The Lust of Sissy 3D Saga - Supportive Sugardaddy

FapHouse 1 year ago

Sissy Gamer Gurl: Feminization & Throat Fucking Part 1 of 3 (1080p)

65% HD 1:01 / 17:26

Sissy Gamer Gurl: Feminization & Throat Fucking Part 1 of 3 (1080p)

FapHouse 1 month 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

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

lick my pussy after pissing. oh yes good bitch. feminization of the stepbrother.

lick my pussy after pissing. oh yes good bitch. feminization of the stepbrother.

PissVids 3 years ago

Playing with My Husband's Asshole

Playing with My Husband's Asshole

XHamster 2 years ago

Peg Curious - Sharing My Man W Roommate

Peg Curious - Sharing My Man W Roommate

XHamster 3 months ago

Sexy Asian Mistress Dominates You

66% 0:39 / 11:30

Sexy Asian Mistress Dominates You

FapHouse 3 months ago

Electra Joness Party on Apr 13, 2026 - Part 3

58% 4K 2:00 / 1:00:15

Electra Joness Party on Apr 13, 2026 - Part 3

Flirt4Free 5 months ago

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 month ago

Sissy Training- Blowjob CEI HYP

Sissy Training- Blowjob CEI HYP

Eporner 5 months ago

Good boys eat cum

Good boys eat cum

XHamster 2 years ago

The Chastity Fuck

The Chastity Fuck

XHamster 5 days ago

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

66% HD 1:01 / 47:50

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

FapHouse 1 month ago

Submissive Sluts volume 4

Submissive Sluts volume 4

XHamster 3 months ago

Kat Fucks Lance in Chastity Part 1 by Sweetfemdom

Kat Fucks Lance in Chastity Part 1 by Sweetfemdom

XHamster 2 years ago

Edelnutte Fabiennes Outen

Edelnutte Fabiennes Outen

XHamster 2 weeks ago

Tia Tizzianni - Sissy Riley Joi Sexual Skills Training

Tia Tizzianni - Sissy Riley Joi Sexual Skills Training

Nuvid 1 week 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

Deep Strap-on Lesson for a Sissy Slut’s Ass

57% HD 1:01 / 9:23

Deep Strap-on Lesson for a Sissy Slut’s Ass

FapHouse 3 weeks ago

Bi Sissy Training

74% HD 1:01 / 34:42

Bi Sissy Training

FapHouse 6 months ago

Jhanne Cherry Private Show

56% HD 2:00 / 27:22

Jhanne Cherry Private Show

Flirt4Free 1 year ago

i made my little sissy have a chastity orgasm

i made my little sissy have a chastity orgasm

XHamster 8 months ago

My cum eating chastity slave gets to clean my feet

My cum eating chastity slave gets to clean my feet

XHamster 1 year ago

Ruth Oliver Private Show

69% 4K 2:00 / 18:06

Ruth Oliver Private Show

Flirt4Free 4 months ago

Sissy Training

XHamster 7 months ago

Harmoni Kalifornia's Sissy Husband Mr. Bruce Experiences Anal Training from Sean

Harmoni Kalifornia's Sissy Husband Mr. Bruce Experiences Anal Training from Sean

Xfeed 1 year ago

Julie and Liza's Latex Doll

69% HD 0:10 / 19:56

Julie and Liza's Latex Doll

LoyalFans 8 months ago

Female POV - feel like a girl

Female POV - feel like a girl

XHamster 3 years ago

Mistress raises her sissy whore. anal training pussy licking

Mistress raises her sissy whore. anal training pussy licking

Itsrealamateurs 1 week ago

Emily & Stesha Private Show

47% 4K 2:00 / 5:57

Emily & Stesha Private Show

Flirt4Free 9 months ago

It's my birthday, she gave me full package...all holes in one day

It's my birthday, she gave me full package...all holes in one day

FapHouse 2 months ago

Blonde Sex Slave Inseminated in Steel Shackles

Blonde Sex Slave Inseminated in Steel Shackles

XHamster 1 month ago

Jhanne Cherry Private Show

50% 4K 2:00 / 22:26

Jhanne Cherry Private Show

Flirt4Free 1 year ago

teaseandthankyou - mandy marx look into my gorgeous eyes while im pegging you but dont shoot too soon porn video

teaseandthankyou - mandy marx look into my gorgeous eyes while im pegging you but dont shoot too soon porn video

BDSMShip 1 year ago

Rubber doll anal sissyfication training on rubber sissy doll

Rubber doll anal sissyfication training on rubber sissy doll

Clips 4 days ago

PROSTATE ORGASM COMPILATION SISSY

PROSTATE ORGASM COMPILATION SISSY

XHamster 4 years ago

Mistress Susi - the Straight Slaves First Sissy Blowjob

Mistress Susi - the Straight Slaves First Sissy Blowjob

XHamster 4 weeks ago

On the Balcony of a 30th Floor with the Best View Ever

69% HD 2:00 / 4:53

On the Balcony of a 30th Floor with the Best View Ever

Flirt4Free 3 years ago

LOSER EXPOSED: The Sissy Madison Files - make me bi - bisexual encouragement - loser exposed - sissy training - slut

LOSER EXPOSED: The Sissy Madison Files - make me bi - bisexual encouragement - loser exposed - sissy training - slut

XHamster 2 weeks ago

Therapy session for sissy boys

Therapy session for sissy boys

XHamster 2 years ago

Femdom Fisting by 2 Asian Dommes

Femdom Fisting by 2 Asian Dommes

XHamster 1 year ago

Secretary Pegging Cucked Boss Cumshot Humiliation BDSM

Secretary Pegging Cucked Boss Cumshot Humiliation BDSM

Eporner 3 years ago

Camilla Polls Private Show

55% 4K 2:00 / 5:37

Camilla Polls Private Show

Flirt4Free 1 year 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 year ago

What a Ridiculous Sissy

57% 1:01 / 18:12

What a Ridiculous Sissy

FapHouse 2 years ago

Randy Moore Fucks Lance Hart in the Ass with Strapon

Randy Moore Fucks Lance Hart in the Ass with Strapon

Fetishpapa 1 month ago

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 5 years ago

Hospitality Whores (full scene 4k)

54% 4K 0:30 / 42:01

Hospitality Whores (full scene 4k)

IWantClips 2 years ago

SLUT TRAINING BFF

66% HD 0:10 / 11:22

SLUT TRAINING BFF

LoyalFans 2 days ago

Humiliation and food crushing for sissy Zombie: Giada Da Vinci disappointed, makes him eat the wilted roses

HD 0:25 / 11:07

Humiliation and food crushing for sissy Zombie: Giada Da Vinci disappointed, makes him eat the wilted roses

Clips4sale 2 days ago

you must always be under lock and key. chastity, always.

you must always be under lock and key. chastity, always.

PornBox 1 week ago

Sissy Slave Training FEMDOM kinky porn

Sissy Slave Training FEMDOM kinky porn

Xozilla 10 months ago

Tiny Blonde Rubbing Her Clit Hard and Fast

48% HD 2:00 / 4:07

Tiny Blonde Rubbing Her Clit Hard and Fast

Flirt4Free 9 years ago

Bi Encouragement - Let Me Help You Give Your First Blowjob

58% 1:01 / 12:42

Bi Encouragement - Let Me Help You Give Your First Blowjob

FapHouse 1 year ago

Enslaved by Sissy Porn: Mind-Melted & Trapped Forever

Enslaved by Sissy Porn: Mind-Melted & Trapped Forever

LoyalFans 2 weeks ago

Dayla Smith Private Show

Dayla Smith Private Show

Flirt4Free 4 days ago

Husband Turned Girlfriend Pt 5

54% HD 0:15 / 20:29

Husband Turned Girlfriend Pt 5

IWantClips 3 years ago

SISSY SLUT FUCKED WITH 8 INCH STRAPON by DominaFire

SISSY SLUT FUCKED WITH 8 INCH STRAPON by DominaFire

XHamster 4 years ago

Vilu Vidish Makes a Boy Into a Girl to Peg Him

Vilu Vidish Makes a Boy Into a Girl to Peg Him

XHamster 5 months ago

Eri Kitami x Melon x HBC; Double Rubber Mistress! Keeping a Rubber Slave!

58% HD 0:11 / 43:52

Eri Kitami x Melon x HBC; Double Rubber Mistress! Keeping a Rubber Slave!

Clips4sale 5 years ago

Prissy sissy dolly - Maid to be used

62% 0:30 / 13:35

Prissy sissy dolly - Maid to be used

Clips4sale 2 years ago

Jhanne Cherry Private Show

52% HD 2:00 / 8:21

Jhanne Cherry Private Show

Flirt4Free 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

Aisha Goldenstein Private Show

4K 2:00 / 19:25

Aisha Goldenstein Private Show

Flirt4Free 6 days ago

Delivery Guy Becomes a Sissy

54% HD 1:01 / 13:05

Delivery Guy Becomes a Sissy

FapHouse 8 months ago

Confess that you are a sissy to your best friend!

Confess that you are a sissy to your best friend!

XHamster 2 months ago

Headmistress ANAL SEXTOY MILKING and ORAL PLEASURE

Headmistress ANAL SEXTOY MILKING and ORAL PLEASURE

MatureTubeHere 4 years ago

Emily & Stesha Private Show

53% 4K 2:00 / 12:53

Emily & Stesha Private Show

Flirt4Free 8 months ago

NO ESCAPE - Butthole Hook Will Produce Every Man Proceed Insane

NO ESCAPE - Butthole Hook Will Produce Every Man Proceed Insane

KAMS 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

Sissy Gets Fisted by Lara Vixette - Anal Fisting in Latex Gloves (MP4)

Sissy Gets Fisted by Lara Vixette - Anal Fisting in Latex Gloves (MP4)

Clips4sale 1 week ago

The Chastity Fuck

The Chastity Fuck

XHamster 4 days ago

Size Queen Sissy Boy Training with CEI

69% HD 1:01 / 20:55

Size Queen Sissy Boy Training with CEI

FapHouse 3 months ago

Fist and shout fisting my man fast

Fist and shout fisting my man fast

XHamster 2 years ago

Sissy Husband BBC Training: Mistress Stellina Obscura Trains Sissy Slut with Humiliating Wedgies, Spankings, Double Anal Pegging

Sissy Husband BBC Training: Mistress Stellina Obscura Trains Sissy Slut with Humiliating Wedgies, Spankings, Double Anal Pegging

XHamster 2 weeks 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

Chastity tutorial - how to wear a chastity cage - part 1

Chastity tutorial - how to wear a chastity cage - part 1

XHamster 8 months ago

Jhanne Cherry Private Show

54% HD 2:00 / 40:31

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Dominafire Pegging her Sissy Slut in Chastity

Dominafire Pegging her Sissy Slut in Chastity

XHamster 3 years ago

Betty Watkins Private Show

58% 4K 2:00 / 14:26

Betty Watkins Private Show

Flirt4Free 9 months ago

Office sissy training

Office sissy training

XHamster 8 months ago

Sissygasm Training: My Cockhungry Femboi Learns to Serve and Suffer

Sissygasm Training: My Cockhungry Femboi Learns to Serve and Suffer

LoyalFans 10 months ago

Amelia Sweety Private Show

HD 2:00 / 11:32

Amelia Sweety Private Show

Flirt4Free 5 days ago

Pissing CFNM domina punishes sissy in BDSM lesson

Pissing CFNM domina punishes sissy in BDSM lesson

Some.Porn 1 year ago

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