Sissy Training (37,946)

The best and newest sissy training videos

Faggot Training: Obsessed With My Man

Faggot Training: Obsessed With My Man

IWantClips 1 month ago

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk! Arya Grander

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk! Arya Grander

BDSMX 6 months ago

Jhanne Cherry Private Show

60% HD 2:00 / 6:41

Jhanne Cherry Private Show

Flirt4Free 10 months ago

Leather Mistress Sissy Balls Fondle Inspection (1080p)

HD 0:16 / 12:13

Leather Mistress Sissy Balls Fondle Inspection (1080p)

Clips4sale 1 week 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

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

Peg Curious - Sharing My Man W Roommate

76% 0:39 / 26:10

Peg Curious - Sharing My Man W Roommate

FapHouse 3 weeks ago

Emmalee Jones Plays with Herself with Fuzzy Socks on

Emmalee Jones Plays with Herself with Fuzzy Socks on

Flirt4Free 1 year ago

Hotwife Date from the Cuckolds Point of View

Hotwife Date from the Cuckolds Point of View

XHamster 2 years 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

Lucie Arztin - Sissy Training

Lucie Arztin - Sissy Training

IcePorn 1 year 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

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

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 4 years ago

She takes the initiative to strap on and cumkiss

She takes the initiative to strap on and cumkiss

XHamster 8 months ago

Adara Smith & Elver Rodriguez Private Show

69% HD 2:00 / 8:21

Adara Smith & Elver Rodriguez Private Show

Camster 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

Dafreeporn 2 weeks ago

Sissy slut training, plug anal, verbal humiliation and impact play Maisa Pravo milf

56% 0:58 / 11:21

Sissy slut training, plug anal, verbal humiliation and impact play Maisa Pravo milf

Clips4sale 1 year ago

Abril Newton Private Show

62% HD 2:00 / 5:08

Abril Newton Private Show

Flirt4Free 10 months ago

April Benson Private Show

62% HD 2:00 / 12:03

April Benson Private Show

Camster 1 year ago

Emmalee Jones Gets Naught

55% 4K 2:00 / 4:26

Emmalee Jones Gets Naught

Flirt4Free 9 months ago

SUCK THIS COCK 4 ME - part 5

SUCK THIS COCK 4 ME - part 5

XHamster 1 year ago

Muscle slut bound and used for being disobedient. Painal is now his life. Female led relationship

Muscle slut bound and used for being disobedient. Painal is now his life. Female led relationship

Pornfact 1 week ago

sissy fantasy - your mistress knows exactly what you want

sissy fantasy - your mistress knows exactly what you want

Pornfact 3 weeks ago

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

66% HD 1:01 / 11:28

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

FapHouse 1 month ago

Jasmine Flowers Pegging Training, femdom Goddess

64% 1:01 / 17:29

Jasmine Flowers Pegging Training, femdom Goddess

FapHouse 1 week ago

Playing with My Husband's Asshole

Playing with My Husband's Asshole

XHamster 2 years ago

Peg Curious - Sharing My Man W Roommate

54% 1:01 / 26:10

Peg Curious - Sharing My Man W Roommate

FapHouse 3 weeks ago

Jhanne Cherry Private Show

57% HD 2:00 / 40:31

Jhanne Cherry Private Show

Camster 10 months ago

Mistresst - High Class Sissy Trained

Mistresst - High Class Sissy Trained

InPorn 4 years ago

Jhanne Cherry Private Show

55% HD 2:00 / 8:06

Jhanne Cherry Private Show

Flirt4Free 10 months ago

Sissy Training in Chastity

56% HD 0:39 / 9:54

Sissy Training in Chastity

FapHouse 1 year ago

Sissy Academy Part 5 - Sissy's Anal Adventure

HD 0:39 / 26:58

Sissy Academy Part 5 - Sissy's Anal Adventure

FapHouse 1 month ago

Jhanne Cherry Private Show

54% HD 2:00 / 22:11

Jhanne Cherry Private Show

Flirt4Free 11 months ago

Bi Domination: Not Entirely Straight

58% HD 1:01 / 21:14

Bi Domination: Not Entirely Straight

FapHouse 3 months ago

Size Queen Sissy Boy Training with CEI

69% HD 1:01 / 20:55

Size Queen Sissy Boy Training with CEI

FapHouse 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

Size Queen Sissy Boy Training with CEI

HD 0:39 / 20:55

Size Queen Sissy Boy Training with CEI

FapHouse 2 weeks ago

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk! Arya Grander

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk! Arya Grander

XHamster 1 year ago

Peg Curious - Sharing My Man W Roommate

Peg Curious - Sharing My Man W Roommate

XHamster 3 weeks ago

Jhanne Cherry Private Show

52% HD 2:00 / 27:22

Jhanne Cherry Private Show

Flirt4Free 10 months ago

The Sissygasm

53% 0:39 / 12:01

FapHouse 1 year 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 3 weeks 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

... - Part 3

58% 4K 2:00 / 4:53

Camster 1 month 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

Sissy Academy Part 1

Sissy Academy Part 1

XHamster 9 months ago

Her mission is to take him deep with her siswet from mrhankeystoys

Her mission is to take him deep with her siswet from mrhankeystoys

Pornfact 1 week ago

ASMR sloppy caged cuck chastity cum (locktober final reward)

ASMR sloppy caged cuck chastity cum (locktober final reward)

XHamster 2 years ago

How to give a prostate massage

How to give a prostate massage

SortPorn 2 years ago

Delivery Guy Becomes a Sissy

50% HD 1:01 / 13:05

Delivery Guy Becomes a Sissy

FapHouse 6 months 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

Sissy slut training by Mistress Tangent

Sissy slut training by Mistress Tangent

HD21 4 years ago

Jhanne Cherry Private Show

50% 4K 2:00 / 22:26

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Emily & Stesha Private Show

55% 4K 2:00 / 8:48

Emily & Stesha Private Show

Flirt4Free 7 months ago

POV Cuckold vol 30

POV Cuckold vol 30

XHamster 6 months ago

Asian Hotwife Turns Husband Into a Cum-eating Cuck

Asian Hotwife Turns Husband Into a Cum-eating Cuck

XHamster 2 months ago

Femdom POV: Sissification, Dirty Talk, Sph, CEI, JOI. Arya Grander and Mistress Priest

Femdom POV: Sissification, Dirty Talk, Sph, CEI, JOI. Arya Grander and Mistress Priest

XHamster 1 year ago

Kinky Carmen In Sissy Bitch Training By

Kinky Carmen In Sissy Bitch Training By

AbXXX 4 years ago

Delivery Guy Becomes a Sissy

65% HD 0:39 / 13:05

Delivery Guy Becomes a Sissy

FapHouse 6 months ago

Femdom POV Sissy Training Pleasure Him

52% HD 1:01 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 3 months ago

Jasmine Flowers Pegging Training, femdom Goddess

Jasmine Flowers Pegging Training, femdom Goddess

FapHouse 1 week ago

She rimmed him so she could pegging him later

She rimmed him so she could pegging him later

XHamster 10 months ago

Amber Fletcher Private Show

58% HD 2:00 / 5:11

Amber Fletcher Private Show

Camster 1 year ago

Femdom POV Sissy Training Pleasure Him

46% HD 0:39 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 3 months ago

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

61% 0:39 / 11:41

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

FapHouse 5 months ago

Miss Brit Slave Training of Sofie Marie

Miss Brit Slave Training of Sofie Marie

XHamster 4 months ago

Size Queen Sissy Male Training with CEI

Size Queen Sissy Male Training with CEI

BigTitsLust 1 week ago

Made to Be a Slut and Feminized by the Birthday Girl

57% HD 1:01 / 11:17

Made to Be a Slut and Feminized by the Birthday Girl

FapHouse 9 months ago

Happy Hour with Apologetic Domme - a short chastity love story

Happy Hour with Apologetic Domme - a short chastity love story

XHamster 3 years ago

Training my wife to anal. First anal stretching. Enema. Ep 24943

Training my wife to anal. First anal stretching. Enema. Ep 24943

XHamster 5 months ago

CUCKOLD CUMS IN PANTIES LIKE A GIRL

CUCKOLD CUMS IN PANTIES LIKE A GIRL

XHamster 3 years ago

Omg!! She Put Finger in My Ass, I Lick Her Ass...she Cum Fart at the End

Omg!! She Put Finger in My Ass, I Lick Her Ass...she Cum Fart at the End

FapHouse 2 days ago

Domina Liza - Sissy Maid Caning Training - Femdom

Domina Liza - Sissy Maid Caning Training - Femdom

DrTuber 2 years ago

Sunday Humiliation Part 3

HD 1:01 / 10:00

Sunday Humiliation Part 3

FapHouse 1 year ago

Extreme Stepmom Throat Training: Heavy Gagging, Atm, Huge Anal Toys, Sissification, Cbt And Golden Shower Finale! Cruel Bdsm Bbw Domme

Extreme Stepmom Throat Training: Heavy Gagging, Atm, Huge Anal Toys, Sissification, Cbt And Golden Shower Finale! Cruel Bdsm Bbw Domme

BDSMX 2 weeks ago

Sensual pegging turns in hard painal that breaks his pussy open. Listen my bitch whine taking dick

Sensual pegging turns in hard painal that breaks his pussy open. Listen my bitch whine taking dick

Pornfact 3 months 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

Extreme Pegging & Fisting Compilation - Femdom fucks male sub anal whore with Huge cock

Extreme Pegging & Fisting Compilation - Femdom fucks male sub anal whore with Huge cock

XHamster 1 year ago

Jhanne Cherry Private Show

54% HD 2:00 / 40:31

Jhanne Cherry Private Show

Flirt4Free 10 months ago

Helloween Night

Helloween Night

XHamster 1 month ago

Vicki Vale Private Show

69% 4K 2:00 / 8:46

Vicki Vale Private Show

Camster 6 days ago

First Step for Virgin Sissy, Cunt Defloration. Anal Stretching, Facesitting, Humiliation, Pee. Mistress Arya Grander.

First Step for Virgin Sissy, Cunt Defloration. Anal Stretching, Facesitting, Humiliation, Pee. Mistress Arya Grander.

XHamster 1 year ago

Asian Hotwife Turns Husband Into a Cum-eating Cuck

Asian Hotwife Turns Husband Into a Cum-eating Cuck

XHamster 3 months ago

wife makes stranger cum and then her spouse licks it up

wife makes stranger cum and then her spouse licks it up

SortPorn 6 days ago

Emily & Stesha Private Show

52% 4K 2:00 / 5:57

Emily & Stesha Private Show

Flirt4Free 7 months ago

Hardcore Up Close Femdom Bi Encouragement Oral-Sex and CEI

Hardcore Up Close Femdom Bi Encouragement Oral-Sex and CEI

SortPorn 3 years ago

wife makes stranger cum and then her spouse licks it up

wife makes stranger cum and then her spouse licks it up

Amateur8 1 week 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

No Pleasure Without Pain

No Pleasure Without Pain

Pornfact 5 days ago

Charlotte Texas Private Show

HD 2:00 / 13:28

Charlotte Texas Private Show

Flirt4Free 3 years ago

Sissy Mesmerize Sessions

54% HD 0:10 / 16:20

Sissy Mesmerize Sessions

LoyalFans 3 years ago

MILF1838- Evil Cougars Sissify Stepson

67% HD 0:25 / 13:23

MILF1838- Evil Cougars Sissify Stepson

IWantClips 1 year ago

Sissy Piss Play - We Taste Each Other's Piss Before Hard Fucking and Pegging

Sissy Piss Play - We Taste Each Other's Piss Before Hard Fucking and Pegging

XHamster 5 days ago

Jasmine Flowers Pegging Training, femdom Goddess

Jasmine Flowers Pegging Training, femdom Goddess

XHamster 2 weeks ago

989 Perverted Stepdaddy, Panty Sniffer Turned Into Sissy Slut - CEI, Ruined Orgasm, Step-daughter in a College Outfit

67% HD 1:01 / 10:37

989 Perverted Stepdaddy, Panty Sniffer Turned Into Sissy Slut - CEI, Ruined Orgasm, Step-daughter in a College Outfit

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 3 weeks ago

Camilla Polls Private Show

58% 4K 2:00 / 11:32

Camilla Polls Private Show

Camster 1 month ago

Sissy anal whore gets deep throated, hardcore pegging, rough ass fucked, and anal fisting

Sissy anal whore gets deep throated, hardcore pegging, rough ass fucked, and anal fisting

Pornzona 1 month ago

Jhanne Cherry Private Show

60% HD 2:00 / 8:56

Jhanne Cherry Private Show

Flirt4Free 11 months ago

Mistress April's training day two: caning drill and enema prep for her slave

Mistress April's training day two: caning drill and enema prep for her slave

Yesvids 1 week ago

Size Queen Sissy Boy Training with CEI

Size Queen Sissy Boy Training with CEI

XHamster 2 weeks ago

Pegging and fisting my husband's asshole

Pegging and fisting my husband's asshole

XHamster 2 years ago

Kamiila & Dimitry Rolex Private Show - Part 4

63% 4K 2:00 / 4:29

Kamiila & Dimitry Rolex Private Show - Part 4

Flirt4Free 2 days ago

Female led discipline. 15 minutes of hard, deep verbal humiliating pegging.

Female led discipline. 15 minutes of hard, deep verbal humiliating pegging.

Pornfact 1 week ago

Mistress Batons Sissy Finishing School Guest Starring Sissy Caning & Bj Training With Mistress Vixen

Mistress Batons Sissy Finishing School Guest Starring Sissy Caning & Bj Training With Mistress Vixen

Boobse.com 1 week ago

siswet from mrhankeystoys glides effortlessly in is hot man pussy

siswet from mrhankeystoys glides effortlessly in is hot man pussy

Pornfact 2 weeks ago

Magically Transformed Sissy ABDL - Penny Barber POV

Magically Transformed Sissy ABDL - Penny Barber POV

Lesbian8 5 months ago

Clara Dee - POV Sissy Pegging - CUSTOM FOR FRED

Clara Dee - POV Sissy Pegging - CUSTOM FOR FRED

Pornzona 6 days ago

Syrische Frau aus Berlin fickt einen deutschen Mann in den Arsch

Syrische Frau aus Berlin fickt einen deutschen Mann in den Arsch

XHamster 2 months ago

Sissy anal whore gets deep throated, hardcore pegging, rough ass fucked, and anal fisting

Sissy anal whore gets deep throated, hardcore pegging, rough ass fucked, and anal fisting

Pornfact 2 weeks ago

Dominatrix Strap-On Dildo Sissy

Dominatrix Strap-On Dildo Sissy

XHamster 2 years ago

Mistress Baton’s Sissy Finishing School Part 3 - Spitroasting

HD 0:10 / 16:00

Mistress Baton’s Sissy Finishing School Part 3 - Spitroasting

LoyalFans 3 weeks 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 1 month ago

Betty Watkins Private Show

62% 4K 2:00 / 14:26

Betty Watkins Private Show

Flirt4Free 7 months ago

Mrs Mature Feet gets a foot massage with special cream

Mrs Mature Feet gets a foot massage with special cream

XHamster 5 months ago

New Sissy in Training (4K)

53% 4K 0:18 / 11:44

New Sissy in Training (4K)

Clips4sale 5 months ago

French Amateur Stepmom Humiliates Her Small Dick Stepson

65% 1:01 / 5:45

French Amateur Stepmom Humiliates Her Small Dick Stepson

FapHouse 2 years ago

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

XHamster 5 months ago

30 Days Mtf Complete Transformation - Slut Training - Crossdressing - Bimbofication - Femdom POV

48% HD 0:39 / 10:01

30 Days Mtf Complete Transformation - Slut Training - Crossdressing - Bimbofication - Femdom POV

FapHouse 1 year ago

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