Sissy Training (19,646)

The best and newest sissy training videos

Jhanne Cherry Private Show

50% 4K 2:00 / 23:18

Jhanne Cherry Private Show

Flirt4Free 9 months ago

Jhanne Cherry Private Show

55% HD 2:00 / 8:06

Jhanne Cherry Private Show

Flirt4Free 7 months ago

Jhanne Cherry Private Show

46% HD 2:00 / 22:11

Jhanne Cherry Private Show

Flirt4Free 8 months ago

Jhanne Cherry Private Show

61% HD 2:00 / 4:58

Jhanne Cherry Private Show

Flirt4Free 6 months ago

What to do with my lover's condom

What to do with my lover's condom

xHamster 1 year ago

EDGING JOI WITH KEGEL WEIGHTLIFTING + BONUS - DAY #4

EDGING JOI WITH KEGEL WEIGHTLIFTING + BONUS - DAY #4

xHamster 3 years ago

POV Pegging JOI CEI Sissy Training - Eat Your Sissy Cream

POV Pegging JOI CEI Sissy Training - Eat Your Sissy Cream

xHamster 4 months ago

Kate Rhoades Private Show

62% 4K 2:00 / 4:18

Kate Rhoades Private Show

Flirt4Free 5 months 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 1 week 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 8 months ago

POV Cuckold volume 9

POV Cuckold volume 9

SortPorn 1 year ago

Jhanne Cherry Private Show

48% 4K 2:00 / 22:26

Jhanne Cherry Private Show

Flirt4Free 8 months ago

Emmalee Jones Party on Apr 6, 2026 - Part 2

4K 2:00 / 30:18

Emmalee Jones Party on Apr 6, 2026 - Part 2

Flirt4Free 2 days ago

Sissy Hose Crossdressing Encouragement Humiliation Trailer Compilation PREVIEWS

Sissy Hose Crossdressing Encouragement Humiliation Trailer Compilation PREVIEWS

Lesbian8 4 months ago

wife makes stranger cum and then her husband licks it up

wife makes stranger cum and then her husband licks it up

xHamster 11 months ago

two Pathetic Sissies Get to Suck and Screw Each Other

two Pathetic Sissies Get to Suck and Screw Each Other

PornFreeNow 3 months ago

I turn my husband's cock into a clit

I turn my husband's cock into a clit

xHamster 2 years ago

Sissy Blowjob

xHamster 5 months ago

Playing with My Husband's Asshole

Playing with My Husband's Asshole

xHamster 2 years ago

Your Sissy dream come True - Female POV blowjob - Roleplay

Your Sissy dream come True - Female POV blowjob - Roleplay

xHamster 1 year ago

Lingerie Lover - Sissy Pegging POV

59% HD 1:01 / 15:30

Lingerie Lover - Sissy Pegging POV

FapHouse 1 year ago

forbidden to for my cuckold in a chastity cage

forbidden to for my cuckold in a chastity cage

xHamster 7 months ago

Delivery Guy Becomes a Sissy

68% HD 0:39 / 13:05

Delivery Guy Becomes a Sissy

FapHouse 2 months ago

BEST RUINED ORGASM JOI

BEST RUINED ORGASM JOI

Pornfact 1 month ago

Sissy Doxy's legs widen for jock all night - Hardcore Femdom Pegging with Mastix Stellina Obscura

Sissy Doxy's legs widen for jock all night - Hardcore Femdom Pegging with Mastix Stellina Obscura

SortPorn 9 months ago

Tita Madurita Private Show

70% HD 2:00 / 10:53

Tita Madurita Private Show

Flirt4Free 2 years ago

Abril Newton Private Show

73% HD 2:00 / 6:54

Abril Newton Private Show

Flirt4Free 6 months ago

Betty Watkins Private Show

63% 4K 2:00 / 14:26

Betty Watkins Private Show

Flirt4Free 3 months ago

POV Sissy Humiliation and Pegging

57% HD 0:39 / 19:13

POV Sissy Humiliation and Pegging

FapHouse 2 years ago

Sissy Training Part 2 - Oral

57% 4K 0:39 / 38:08

Sissy Training Part 2 - Oral

FapHouse 2 months ago

Sissy Dreamland Femdom Mistress fucks hot femboy's ass with her big black cock strapon - Part 2 MILF pegs & Dominates cuck loser

Sissy Dreamland Femdom Mistress fucks hot femboy's ass with her big black cock strapon - Part 2 MILF pegs & Dominates cuck loser

xHamster 1 year ago

Moan for me my sissy bitch - sissification with collar, anal plugs and rubber pussy

Moan for me my sissy bitch - sissification with collar, anal plugs and rubber pussy

xHamster 3 years ago

Sissy Slut - Outdoor Domination

Sissy Slut - Outdoor Domination

xHamster 3 years ago

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

xHamster 2 months ago

Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

56% 1:01 / 20:13

Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

FapHouse 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

Asian Hotwife Turns Husband Into a Cum-eating Cuck

74% 0:39 / 22:54

Asian Hotwife Turns Husband Into a Cum-eating Cuck

FapHouse 1 week ago

Asian Hotwife Turns Husband Into a Cum-eating Cuck

63% 1:01 / 22:54

Asian Hotwife Turns Husband Into a Cum-eating Cuck

FapHouse 1 week ago

POV Cuckold vol 30

POV Cuckold vol 30

xHamster 2 months ago

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 4 years 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

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

Vends-ta-culotte - Gorgeous luscious French brunette gives you a good lesson of anal training

Vends-ta-culotte - Gorgeous luscious French brunette gives you a good lesson of anal training

xHamster 4 weeks ago

I lock my husband's cock in a chastity cage

I lock my husband's cock in a chastity cage

xHamster 1 year ago

My husband has a new cock

My husband has a new cock

xHamster 1 year ago

Hotwife Date from the Cuckolds Point of View

Hotwife Date from the Cuckolds Point of View

xHamster 2 years ago

Happy Hour with Apologetic Domme - a short chastity love story

Happy Hour with Apologetic Domme - a short chastity love story

xHamster 2 years ago

Sissy Academy Part 1

Sissy Academy Part 1

xHamster 6 months ago

Miss Brit Slave Training of Sofie Marie

Miss Brit Slave Training of Sofie Marie

xHamster 1 month ago

Femdom Sissy Anal Training: Cum in Your Cage CEI

Femdom Sissy Anal Training: Cum in Your Cage CEI

PornFreeNow 5 days ago

Kinky Carmen In Sissy Bitch Training By

Kinky Carmen In Sissy Bitch Training By

AbXXX 4 years ago

Wife Makes Stranger Cum and Then Her Husband Licks It up

56% 1:01 / 8:25

Wife Makes Stranger Cum and Then Her Husband Licks It up

FapHouse 11 months ago

Stella's Cat Training

Stella's Cat Training

xHamster 1 month ago

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

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

xHamster 2 months ago

Delivery Guy Becomes a Sissy

49% HD 1:01 / 13:05

Delivery Guy Becomes a Sissy

FapHouse 2 months ago

Femdom and Cuckold Humiliation Compilation

Femdom and Cuckold Humiliation Compilation

xHamster 11 months ago

How to give a prostate massage

How to give a prostate massage

SortPorn 2 years ago

Femdom Sissy Humiliation: Emasculated and Impotent

57% HD 1:01 / 18:05

Femdom Sissy Humiliation: Emasculated and Impotent

FapHouse 1 week ago

Sissy Mesmerize Sessions

61% HD 0:10 / 16:20

Sissy Mesmerize Sessions

LoyalFans 3 years ago

Femdom Sissy Anal Training: Cum in Your Cage CEI

HD 1:01 / 11:10

Femdom Sissy Anal Training: Cum in Your Cage CEI

FapHouse 1 week ago

Mistresst - High Class Sissy Trained

Mistresst - High Class Sissy Trained

InPorn 4 years ago

FEMDOM SISSY PEGGING ANAL CUM EATING BIG TITS STRAPON CUMSHOT

FEMDOM SISSY PEGGING ANAL CUM EATING BIG TITS STRAPON CUMSHOT

xHamster 2 months ago

Pegging and fisting my husband's asshole

Pegging and fisting my husband's asshole

xHamster 2 years ago

She rimmed him so she could pegging him later

She rimmed him so she could pegging him later

xHamster 7 months ago

Caged Clitty Ruined

Caged Clitty Ruined

xHamster 4 weeks ago

Fpov: Blowjob and Deepthroat Training for Sissies

Fpov: Blowjob and Deepthroat Training for Sissies

xHamster 3 months ago

Your New Life as My Free Use Sissy

47% HD 1:01 / 16:13

Your New Life as My Free Use Sissy

FapHouse 1 month ago

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

57% 0:39 / 11:41

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

FapHouse 2 months ago

Magically Transformed Sissy ABDL - Penny Barber POV

Magically Transformed Sissy ABDL - Penny Barber POV

Lesbian8 2 months 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 9 months ago

Femdom Sissy Anal Training: Cum in Your Cage CEI

Femdom Sissy Anal Training: Cum in Your Cage CEI

Lesbian8 5 days ago

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

53% HD 0:39 / 10:01

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

FapHouse 10 months ago

30 Days Chastity Follow up

59% 1:01 / 6:47

30 Days Chastity Follow up

FapHouse 3 weeks 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 4 days ago

Wife Makes Stranger Cum and Then Her Husband Licks It up

52% 0:39 / 8:25

Wife Makes Stranger Cum and Then Her Husband Licks It up

FapHouse 11 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

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

Hardcore Up Close Femdom Bi Encouragement Oral and CEI

Hardcore Up Close Femdom Bi Encouragement Oral and CEI

FreePorn8 3 years ago

SUCK THIS COCK 4 ME - part 5

SUCK THIS COCK 4 ME - part 5

xHamster 1 year ago

Femdom Sissy training - accept and obey

Femdom Sissy training - accept and obey

Juicexxx 2 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

Bimbo Magic Spell

56% HD 1:01 / 15:05

Bimbo Magic Spell

FapHouse 2 weeks 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

Hardcore Up Close Femdom Bi Encouragement Oral job and CEI

Hardcore Up Close Femdom Bi Encouragement Oral job and CEI

Dafreeporn 3 years ago

My Dirty Little Whore

My Dirty Little Whore

Pornfact 3 days ago

your purpose in life

your purpose in life

Pornfact 6 days ago

siswet from mrhankeystoys glides effortlessly in is hot man pussy

siswet from mrhankeystoys glides effortlessly in is hot man pussy

Pornfact 1 week ago

Femdom Sissy Anal Training: Cum in Your Cage CEI

HD 0:39 / 11:10

Femdom Sissy Anal Training: Cum in Your Cage CEI

FapHouse 1 week ago

Bimbo Magic Spell

HD 0:39 / 15:05

Bimbo Magic Spell

FapHouse 2 weeks ago

Sissy Clitty Affirmations

60% HD 1:01 / 9:15

Sissy Clitty Affirmations

FapHouse 1 week ago

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

65% 0:39 / 11:41

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

FapHouse 2 months ago

ASMR sloppy caged cuck chastity cum (locktober final reward)

ASMR sloppy caged cuck chastity cum (locktober final reward)

xHamster 2 years ago

Compilation d'humiliation femdom

Compilation d'humiliation femdom

xHamster 1 year ago

Turning U into My Stepson's Sissy Sex Toy - Feminization POV Penny Barber

Turning U into My Stepson's Sissy Sex Toy - Feminization POV Penny Barber

Lesbian8 2 months ago

Emily & Stesha Private Show

Emily & Stesha Private Show

Flirt4Free 4 days ago

In Sisssy clothes this is how you will soon look

In Sisssy clothes this is how you will soon look

xHamster 1 month ago

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

61% HD 0:39 / 5:10

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

FapHouse 8 months ago

Hot MILF Femdom Wife Exposes Her Husband as ANAL SISSY SLUT Featuring Mistress Stellina Obscura

Hot MILF Femdom Wife Exposes Her Husband as ANAL SISSY SLUT Featuring Mistress Stellina Obscura

xHamster 11 months ago

CBT I Fuck His Dick in Close up

CBT I Fuck His Dick in Close up

xHamster 1 year ago

I fuck a stranger in a parking lot to humiliate my husband

I fuck a stranger in a parking lot to humiliate my husband

xHamster 2 years ago

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

62% HD 1:01 / 5:10

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

FapHouse 8 months ago

Jhanne Cherry Private Show

56% HD 2:00 / 40:31

Jhanne Cherry Private Show

Flirt4Free 6 months ago

Sexy Anal Pegging Session with My Sissy Slut Gaped in a Tartan Mini Skirt

Sexy Anal Pegging Session with My Sissy Slut Gaped in a Tartan Mini Skirt

xHamster 7 months ago

Emily & Stesha Private Show

58% 4K 2:00 / 5:57

Emily & Stesha Private Show

Flirt4Free 3 months ago

Femdom Humiliation - Your Are a Sissy and a Cuckold

HD 1:01 / 16:00

Femdom Humiliation - Your Are a Sissy and a Cuckold

FapHouse 3 days ago

Made to Be a Slut and Feminized by the Birthday Girl

58% HD 1:01 / 11:17

Made to Be a Slut and Feminized by the Birthday Girl

FapHouse 5 months ago

Overweight Piggy Activation Part two

Overweight Piggy Activation Part two

FreePorn8 1 week ago

Angelica Swiss Party on Jan 21, 2026 - Part 2

63% 4K 2:00 / 4:00:00+

Angelica Swiss Party on Jan 21, 2026 - Part 2

Flirt4Free 2 months ago

Emily & Stesha Private Show

53% 4K 2:00 / 5:53

Emily & Stesha Private Show

Flirt4Free 3 months ago

Sissy Anal JOI

67% HD 0:39 / 7:41

FapHouse 2 years ago

Step Mommy Dresses Him up in Panties and Makes Him Cum Twice

Step Mommy Dresses Him up in Panties and Makes Him Cum Twice

xHamster 7 months ago

Fat Piggy Activation Part 2

Fat Piggy Activation Part 2

Dafreeporn 1 week ago

Stepmommy Turns YOU into a Little Bunny Sissy Bitch - Penny Barber Taboo

Stepmommy Turns YOU into a Little Bunny Sissy Bitch - Penny Barber Taboo

PornFreeNow 2 months ago

Betty Sandra Private Show

53% HD 2:00 / 14:37

Betty Sandra Private Show

Flirt4Free 4 years ago

Goddess Finally Got Her First Female Sub (you, Sissy)

Goddess Finally Got Her First Female Sub (you, Sissy)

xHamster 10 months ago

Training Zero Femdom Sissy Feminization Slave Bondage Cum Orgasm Humiliation BDSM Real Homemade Miilf Stepmom

Training Zero Femdom Sissy Feminization Slave Bondage Cum Orgasm Humiliation BDSM Real Homemade Miilf Stepmom

xHamster 1 year ago

Emily & Stesha Private Show

68% 4K 2:00 / 11:42

Emily & Stesha Private Show

Flirt4Free 1 week ago

Anal Training, Learning

Anal Training, Learning

xHamster 2 months ago

Wear These for Step-mommy!

Wear These for Step-mommy!

xHamster 1 year ago

Bar Flirt Fantasy: Chastity and Sissy Transformation

Bar Flirt Fantasy: Chastity and Sissy Transformation

xHamster 7 months ago

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