Sissy Training (18,638)

The best and newest sissy training videos

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

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

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

xHamster 2 weeks ago

Pegging and Fisting His Tight Asshole

Pegging and Fisting His Tight Asshole

xHamster 1 year ago

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

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

FreePorn8 4 weeks ago

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

48% HD 1:01 / 12:49

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

FapHouse 2 months ago

Angelica Swiss Party on Feb 8, 2026 - Part 4

HD 2:00 / 33:23

Angelica Swiss Party on Feb 8, 2026 - Part 4

Flirt4Free 1 week ago

Sissy needs make up

Sissy needs make up

FapHouse 3 years ago

Magically Transformed Sissy ABDL - Penny Barber POV

Magically Transformed Sissy ABDL - Penny Barber POV

Lesbian8 3 weeks ago

Day 5 of 7: CBT Day

Day 5 of 7: CBT Day

xHamster 2 months ago

Sissy Academy Part 1

Sissy Academy Part 1

xHamster 4 months ago

forbidden to for my cuckold in a chastity cage

forbidden to for my cuckold in a chastity cage

xHamster 5 months ago

Chastity Sissy Acquiesces to be Cuck to get unlocked. Then Wife Pegs Butt

Chastity Sissy Acquiesces to be Cuck to get unlocked. Then Wife Pegs Butt

SortPorn 1 year ago

Muslim Hijabi mistress wearing saree while he was locked in chastity Part 1

Muslim Hijabi mistress wearing saree while he was locked in chastity Part 1

xHamster 1 month 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

Double Dom with Lady Valeska: Horny Sissy Being Sucked in the Latex Bag

47% HD 1:01 / 8:39

Double Dom with Lady Valeska: Horny Sissy Being Sucked in the Latex Bag

FapHouse 1 year ago

Junior & Brittney Private Show

63% HD 2:00 / 5:13

Junior & Brittney Private Show

Flirt4Free 1 year ago

Angelica Swiss Party on Feb 8, 2026 - Part 4

HD 2:00 / 28:42

Angelica Swiss Party on Feb 8, 2026 - Part 4

Flirt4Free 1 week ago

Jhanne Cherry Private Show

44% HD 2:00 / 22:11

Jhanne Cherry Private Show

Flirt4Free 6 months ago

Your Sissy dream come True - Female POV blowjob - Roleplay

Your Sissy dream come True - Female POV blowjob - Roleplay

xHamster 1 year ago

Helena Red Private Show

68% HD 2:00 / 10:43

Helena Red Private Show

Flirt4Free 3 years ago

Dominatrix Mistress April - Rose Garden Part one

Dominatrix Mistress April - Rose Garden Part one

xHamster 4 years ago

Jhanne Cherry Private Show

53% HD 2:00 / 6:41

Jhanne Cherry Private Show

Flirt4Free 5 months ago

POV Cuckold volume 9

POV Cuckold volume 9

SortPorn 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 1 year ago

Wife Pisses Outdoors

Wife Pisses Outdoors

xHamster 6 days ago

Abril Newton Private Show

63% HD 2:00 / 1:41:59

Abril Newton Private Show

Flirt4Free 6 months ago

Emily & Stesha Private Show

61% 4K 2:00 / 5:57

Emily & Stesha Private Show

Flirt4Free 1 month ago

Sofi Saenz Private Show

66% HD 2:00 / 8:23

Sofi Saenz Private Show

Flirt4Free 5 months ago

Nefertiti & Demian Private Show

57% HD 2:00 / 9:43

Nefertiti & Demian Private Show

Flirt4Free 2 years ago

MILF Helena Locke Dominates Pierce with CBT Ass Fucking and Sissy Training in Latex Outfit

MILF Helena Locke Dominates Pierce with CBT Ass Fucking and Sissy Training in Latex Outfit

Eporner 2 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 9 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 7 months ago

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 4 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

I fuck my husband on the beach

I fuck my husband on the beach

xHamster 1 year ago

Come on, Honey. I'll Fuck Your Ass. Stepmom Testing Stepsons Anal Hole.

62% 0:39 / 8:35

Come on, Honey. I'll Fuck Your Ass. Stepmom Testing Stepsons Anal Hole.

FapHouse 1 week ago

Sissy Training Part 2 - Oral

58% 4K 1:01 / 38:08

Sissy Training Part 2 - Oral

FapHouse 4 weeks ago

POV Cuckold vol 30

POV Cuckold vol 30

xHamster 1 month ago

Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

57% 0:39 / 20:13

Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

FapHouse 1 year ago

Wife Makes Stranger Cum and Then Her Husband Licks It up

58% 1:01 / 8:25

Wife Makes Stranger Cum and Then Her Husband Licks It up

FapHouse 9 months ago

My husband has a new cock

My husband has a new cock

xHamster 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

Playing with My Husband's Asshole

Playing with My Husband's Asshole

xHamster 1 year ago

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

xHamster 3 weeks ago

Hotwife Date from the Cuckolds Point of View

Hotwife Date from the Cuckolds Point of View

xHamster 2 years ago

How to give a prostate massage

How to give a prostate massage

SortPorn 2 years ago

Jhanne Cherry Private Show

50% 4K 2:00 / 23:18

Jhanne Cherry 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

Amateur8 3 years 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

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

She rimmed him so she could pegging him later

She rimmed him so she could pegging him later

xHamster 5 months 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 4 months ago

Delivery Guy Becomes a Sissy

58% HD 1:01 / 13:05

Delivery Guy Becomes a Sissy

FapHouse 1 month ago

Come on, Honey. I'll Fuck Your Ass. Stepmom Testing Stepsons Anal Hole.

62% 0:39 / 8:35

Come on, Honey. I'll Fuck Your Ass. Stepmom Testing Stepsons Anal Hole.

FapHouse 1 week ago

Sissy Training & Teaching U How to Suck Alpha's Huge Cock!

Sissy Training & Teaching U How to Suck Alpha's Huge Cock!

xHamster 10 months ago

The White Room - Humiliation and Milking - Part 1

The White Room - Humiliation and Milking - Part 1

xHamster 2 weeks ago

CUM CHALLENGE FOR BISEXUAL PERVS

CUM CHALLENGE FOR BISEXUAL PERVS

xHamster 1 year ago

Jhanne Cherry Private Show

48% HD 2:00 / 27:22

Jhanne Cherry Private Show

Flirt4Free 5 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

ASMR sloppy caged cuck chastity cum (locktober final reward)

ASMR sloppy caged cuck chastity cum (locktober final reward)

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 7 months ago

Bar Flirt Fantasy: Chastity and Sissy Transformation

Bar Flirt Fantasy: Chastity and Sissy Transformation

xHamster 6 months ago

Magically Transformed Sissy ABDL - Penny Barber POV

Magically Transformed Sissy ABDL - Penny Barber POV

PornFreeNow 3 weeks ago

Mistresst - High Class Sissy Trained

Mistresst - High Class Sissy Trained

InPorn 4 years ago

Kinky Carmen In Sissy Bitch Training By

Kinky Carmen In Sissy Bitch Training By

AbXXX 3 years ago

Jhanne Cherry Private Show

67% 4K 2:00 / 14:24

Jhanne Cherry Private Show

Flirt4Free 7 months ago

Ava Maddison Private Show

66% 4K 2:00 / 8:28

Ava Maddison Private Show

Flirt4Free 1 week ago

Fpov: Blowjob and Deepthroat Training for Sissies

Fpov: Blowjob and Deepthroat Training for Sissies

xHamster 2 months ago

Emily & Stesha Private Show

53% 4K 2:00 / 12:53

Emily & Stesha Private Show

Flirt4Free 3 weeks ago

Magically Transformed Sissy ABDL - Penny Barber POV

Magically Transformed Sissy ABDL - Penny Barber POV

FreePorn8 4 weeks ago

Mistress Olivia trains you little slut to be a sissy whore! German mistress with huge titsDirtytalk

Mistress Olivia trains you little slut to be a sissy whore! German mistress with huge titsDirtytalk

xHamster 3 weeks ago

Rainwear Humiliation - Shiny, Stupid, and Mine

Rainwear Humiliation - Shiny, Stupid, and Mine

xHamster 3 months ago

CBT I Fuck His Dick in Close up

CBT I Fuck His Dick in Close up

xHamster 1 year ago

Sissy Training in Chastity

57% HD 0:39 / 9:54

Sissy Training in Chastity

FapHouse 1 year ago

POV Two Milfs in Bodystocking Strap-On Domination

POV Two Milfs in Bodystocking Strap-On Domination

xHamster 1 year 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 7 months ago

Angelica Swiss Party on Jan 21, 2026 - Part 2

64% 4K 2:00 / 4:00:00+

Angelica Swiss Party on Jan 21, 2026 - Part 2

Flirt4Free 1 month ago

What to do with my lover's condom

What to do with my lover's condom

xHamster 1 year ago

Jhanne Cherry Private Show

58% 4K 2:00 / 6:40

Jhanne Cherry Private Show

Flirt4Free 7 months 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

two Pathetic Sissies Get to Suck and Screw Each Other

two Pathetic Sissies Get to Suck and Screw Each Other

PornFreeNow 2 months ago

Sissy Mesmerize Sessions

61% HD 0:10 / 16:20

Sissy Mesmerize Sessions

LoyalFans 3 years ago

Sissy slut training by Mistress Tangent

Sissy slut training by Mistress Tangent

HD21 3 years ago

Amber Fletcher Private Show - Part 3

65% HD 2:00 / 21:25

Amber Fletcher Private Show - Part 3

Flirt4Free 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 3 weeks ago

Jhanne Cherry Private Show

49% 4K 2:00 / 22:26

Jhanne Cherry Private Show

Flirt4Free 7 months ago

Taboo Female Supremacy - Penny Barber

Taboo Female Supremacy - Penny Barber

Lesbian8 3 weeks ago

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

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

FapHouse 3 weeks ago

Jhanne Cherry Private Show

58% 4K 2:00 / 6:21

Jhanne Cherry Private Show

Flirt4Free 7 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 10 months ago

The evolution of the size of a chastity cage cock

The evolution of the size of a chastity cage cock

xHamster 1 year ago

Sissy Slave Femdom Feminization Humiliation Nails Painted Chastity BDSM Real Homemade Amateur Milf

Sissy Slave Femdom Feminization Humiliation Nails Painted Chastity BDSM Real Homemade Amateur Milf

xHamster 2 years ago

The Sissygasm

47% 1:01 / 12:01

FapHouse 8 months ago

In Sisssy clothes this is how you will soon look

In Sisssy clothes this is how you will soon look

xHamster 1 week ago

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

64% 0:39 / 11:41

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

FapHouse 3 weeks ago

Jhanne Cherry Private Show

56% HD 2:00 / 40:31

Jhanne Cherry Private Show

Flirt4Free 5 months ago

Rainwear Humiliation - Shiny, Stupid, and Mine

Rainwear Humiliation - Shiny, Stupid, and Mine

xHamster 2 months ago

Camilla Polls Private Show

57% 4K 2:00 / 6:05

Camilla Polls Private Show

Flirt4Free 7 months ago

Miss Alika White Size Queen Sissy Training

Miss Alika White Size Queen Sissy Training

YepTube 1 month ago

All about collars (from a Femdom perspective)

All about collars (from a Femdom perspective)

MatureTubeHere 4 years ago

On the beach, my cuckold licks my

On the beach, my cuckold licks my

xHamster 10 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 8 months ago

SUCK THIS COCK 4 ME - part 5

SUCK THIS COCK 4 ME - part 5

xHamster 11 months ago

Camilla Polls Private Show

64% 4K 2:00 / 25:57

Camilla Polls Private Show

Flirt4Free 6 months ago

The Bimbofication Serum

58% HD 0:10 / 16:32

The Bimbofication Serum

LoyalFans 2 years ago

Pegging and fisting my husband's asshole

Pegging and fisting my husband's asshole

xHamster 2 years ago

Dominatrix Strap-On Dildo Sissy

Dominatrix Strap-On Dildo Sissy

xHamster 2 years ago

Emily & Stesha Private Show

54% 4K 2:00 / 5:53

Emily & Stesha Private Show

Flirt4Free 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 1 month ago

Wear These for Step-mommy!

Wear These for Step-mommy!

xHamster 1 year ago

Emily & Stesha Private Show

49% 4K 2:00 / 7:00

Emily & Stesha Private Show

Flirt4Free 3 weeks ago

Emily & Stesha Private Show

47% 4K 2:00 / 4:08

Emily & Stesha Private Show

Flirt4Free 3 weeks ago

Sissy Anal JOI

52% HD 1:01 / 7:41

FapHouse 2 years ago

Abril Newton Private Show

59% 4K 2:00 / 11:48

Abril Newton Private Show

Flirt4Free 6 months ago

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

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

PornFreeNow 3 weeks ago

Abril Newton Private Show

57% HD 2:00 / 19:22

Abril Newton Private Show

Flirt4Free 6 months ago

You Will Be Wearing a Headscarf Today Sissy Kelly

You Will Be Wearing a Headscarf Today Sissy Kelly

xHamster 1 year ago

She planned it all out..

She planned it all out..

xHamster 5 months ago

Sissy Blowjob

xHamster 3 months ago

Abril Newton Private Show

55% 4K 2:00 / 6:08

Abril Newton Private Show

Flirt4Free 5 months ago

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