Sissy Training (18,600)

The best and newest sissy training videos

Pegging and Fisting His Tight Asshole

Pegging and Fisting His Tight Asshole

xHamster 1 year ago

Junior & Brittney Private Show

63% HD 2:00 / 5:13

Junior & Brittney Private Show

Flirt4Free 1 year ago

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

49% 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

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 3 weeks ago

Magically Transformed Sissy ABDL - Penny Barber POV

Magically Transformed Sissy ABDL - Penny Barber POV

Lesbian8 3 weeks ago

I fuck my husband on the beach

I fuck my husband on the beach

xHamster 1 year 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

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

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

Playing with My Husband's Asshole

Playing with My Husband's Asshole

xHamster 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

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

Strict Dominatrix in Spandex and her very absolutely virgin sissy that came for cunt defloration!

Strict Dominatrix in Spandex and her very absolutely virgin sissy that came for cunt defloration!

XVideos 1 year 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

Kinky Carmen In Sissy Bitch Training By

Kinky Carmen In Sissy Bitch Training By

AbXXX 3 years ago

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 4 years 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

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

Wife Makes Stranger Cum and Then Her Husband Licks It up

59% 1:01 / 8:25

Wife Makes Stranger Cum and Then Her Husband Licks It up

FapHouse 9 months 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 3 years ago

POV Cuckold volume 9

POV Cuckold volume 9

SortPorn 1 year ago

Jhanne Cherry Private Show

54% HD 2:00 / 6:41

Jhanne Cherry Private Show

Flirt4Free 5 months ago

Abril Newton Private Show

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

Abril Newton Private Show

Flirt4Free 6 months ago

Emily & Stesha Private Show

58% 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

Abril Newton Private Show

54% HD 2:00 / 17:42

Abril Newton Private Show

Flirt4Free 5 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 6 months 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

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

Hardcore Up Close Femdom Bi Encouragement Oral Sex and CEI

Hardcore Up Close Femdom Bi Encouragement Oral Sex and CEI

Amateur8 3 years ago

POV Cuckold vol 30

POV Cuckold vol 30

xHamster 1 month 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

Delivery Guy Becomes a Sissy

63% HD 1:01 / 13:05

Delivery Guy Becomes a Sissy

FapHouse 1 month ago

Hotwife Date from the Cuckolds Point of View

Hotwife Date from the Cuckolds Point of View

xHamster 2 years ago

My husband has a new cock

My husband has a new cock

xHamster 1 year ago

Sissy Training Part 2 - Oral

58% 4K 1:01 / 38:08

Sissy Training Part 2 - Oral

FapHouse 3 weeks ago

The White Room - Humiliation and Milking - Part 1

The White Room - Humiliation and Milking - Part 1

xHamster 1 week 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 MILF Mistress Inserts Huge Dildo Into Slave Ass

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

xHamster 2 weeks ago

Jhanne Cherry Private Show

50% 4K 2:00 / 23:18

Jhanne Cherry Private Show

Flirt4Free 7 months ago

How to give a prostate massage

How to give a prostate massage

SortPorn 2 years 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

Emily & Stesha Private Show

58% 4K 2:00 / 12:53

Emily & Stesha Private Show

Flirt4Free 2 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

Mistresst - High Class Sissy Trained

Mistresst - High Class Sissy Trained

InPorn 4 years ago

She rimmed him so she could pegging him later

She rimmed him so she could pegging him later

xHamster 5 months 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

Fpov: Blowjob and Deepthroat Training for Sissies

Fpov: Blowjob and Deepthroat Training for Sissies

xHamster 2 months ago

Jhanne Cherry Private Show

55% HD 2:00 / 40:31

Jhanne Cherry Private Show

Flirt4Free 5 months ago

Jhanne Cherry Private Show

67% 4K 2:00 / 14:24

Jhanne Cherry Private Show

Flirt4Free 7 months ago

ASMR sloppy caged cuck chastity cum (locktober final reward)

ASMR sloppy caged cuck chastity cum (locktober final reward)

xHamster 2 years ago

Jhanne Cherry Private Show

49% 4K 2:00 / 22:26

Jhanne Cherry Private Show

Flirt4Free 7 months ago

Jhanne Cherry Private Show

51% HD 2:00 / 27:22

Jhanne Cherry Private Show

Flirt4Free 4 months ago

CUM CHALLENGE FOR BISEXUAL PERVS

CUM CHALLENGE FOR BISEXUAL PERVS

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

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

Emily & Stesha Private Show

49% 4K 2:00 / 7:00

Emily & Stesha Private Show

Flirt4Free 2 weeks ago

Sissy slut training by Mistress Tangent

Sissy slut training by Mistress Tangent

HD21 3 years ago

two Pathetic Sissies Get to Suck and Screw Each Other

two Pathetic Sissies Get to Suck and Screw Each Other

PornFreeNow 1 month ago

Therapy session for sissy boys

Therapy session for sissy boys

xHamster 2 years ago

CBT I Fuck His Dick in Close up

CBT I Fuck His Dick in Close up

xHamster 1 year ago

Rainwear Humiliation - Shiny, Stupid, and Mine

Rainwear Humiliation - Shiny, Stupid, and Mine

xHamster 3 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 4 weeks ago

Pegging and fisting my husband's asshole

Pegging and fisting my husband's asshole

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

Bar Flirt Fantasy: Chastity and Sissy Transformation

Bar Flirt Fantasy: Chastity and Sissy Transformation

xHamster 6 months ago

Miss Alika White Size Queen Sissy Training

Miss Alika White Size Queen Sissy Training

YepTube 1 month ago

In Sisssy clothes this is how you will soon look

In Sisssy clothes this is how you will soon look

xHamster 4 days 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

Emily & Stesha Private Show

47% 4K 2:00 / 4:08

Emily & Stesha Private Show

Flirt4Free 2 weeks ago

The Sissygasm

47% 1:01 / 12:01

FapHouse 8 months ago

Magically Transformed Sissy ABDL - Penny Barber POV

Magically Transformed Sissy ABDL - Penny Barber POV

PornFreeNow 3 weeks ago

Magically Transformed Sissy ABDL - Penny Barber POV

Magically Transformed Sissy ABDL - Penny Barber POV

FreePorn8 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 2 weeks ago

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

56% HD 0:39 / 10:01

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

FapHouse 9 months ago

Amber Fletcher Private Show - Part 3

65% HD 2:00 / 21:25

Amber Fletcher Private Show - Part 3

Flirt4Free 1 year ago

Jhanne Cherry Private Show

58% 4K 2:00 / 6:40

Jhanne Cherry Private Show

Flirt4Free 7 months 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

She planned it all out..

She planned it all out..

xHamster 5 months ago

Sissy Mesmerize Sessions

61% HD 0:10 / 16:20

Sissy Mesmerize Sessions

LoyalFans 3 years ago

Emmalee Jones Spanks Her Ass While She Gets Fucked

Emmalee Jones Spanks Her Ass While She Gets Fucked

Flirt4Free 2 weeks ago

Sissy Anal JOI

52% HD 1:01 / 7:41

FapHouse 2 years 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 2 weeks ago

My husband's cock is desperate in his chastity cage

My husband's cock is desperate in his chastity cage

xHamster 1 year ago

Feminization of the cuckold in a chastity cage

Feminization of the cuckold in a chastity cage

PornFreeNow 6 months ago

Sissy Atonement

Sissy Atonement

FreePorn8 3 weeks ago

Cuckolded, caged and humiliated

Cuckolded, caged and humiliated

xHamster 1 year ago

Kristinaxxx sissy training

Kristinaxxx sissy training

AnySex 2 years ago

SUCK THIS COCK 4 ME - part 5

SUCK THIS COCK 4 ME - part 5

xHamster 11 months ago

Rainwear Humiliation - Shiny, Stupid, and Mine

Rainwear Humiliation - Shiny, Stupid, and Mine

xHamster 2 months ago

Jhanne Cherry Private Show

67% 4K 2:00 / 7:28

Jhanne Cherry Private Show

Flirt4Free 7 months ago

You Will Be Wearing a Headscarf Today Sissy Kelly

You Will Be Wearing a Headscarf Today Sissy Kelly

xHamster 1 year ago

Jhanne Cherry Private Show

58% 4K 2:00 / 21:44

Jhanne Cherry Private Show

Flirt4Free 7 months ago

Emmalee Jones Talks Dirty for Daddy Up Close

Emmalee Jones Talks Dirty for Daddy Up Close

Flirt4Free 5 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 9 months ago

Taboo Female Supremacy - Penny Barber

Taboo Female Supremacy - Penny Barber

Lesbian8 3 weeks ago

Jhanne Cherry Private Show

65% 4K 2:00 / 4:59

Jhanne Cherry Private Show

Flirt4Free 7 months ago

Sharon J Private Show

Sharon J Private Show

Flirt4Free 2 years ago

Femdom and Cuckold Humiliation Compilation

Femdom and Cuckold Humiliation Compilation

xHamster 9 months ago

Emily & Stesha Private Show

52% 4K 2:00 / 7:33

Emily & Stesha Private Show

Flirt4Free 2 weeks ago

A sissy fetish for high heels

A sissy fetish for high heels

xHamster 3 months ago

Wear These for Step-mommy!

Wear These for Step-mommy!

xHamster 1 year ago

Emily & Stesha Private Show

54% 4K 2:00 / 5:53

Emily & Stesha Private Show

Flirt4Free 1 month ago

Stepsister Fuck Stepbrother in Ass Very Big Strap on Dildo Vibrator Anal Pegging Femdom Spanking

76% HD 1:01 / 7:58

Stepsister Fuck Stepbrother in Ass Very Big Strap on Dildo Vibrator Anal Pegging Femdom Spanking

FapHouse 1 year ago

Headmistress ANAL SEXTOY MILKING and ORAL PLEASURE

Headmistress ANAL SEXTOY MILKING and ORAL PLEASURE

MatureTubeHere 3 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

Mistress wife discipline her sissy husband on kitchen

Mistress wife discipline her sissy husband on kitchen

xHamster 2 years ago

Emmalee Jones Party on Feb 10, 2026 - Part 2

4K 2:00 / 23:21

Emmalee Jones Party on Feb 10, 2026 - Part 2

Flirt4Free 1 week ago

Jhanne Cherry Private Show

59% 4K 2:00 / 6:21

Jhanne Cherry Private Show

Flirt4Free 7 months ago

All about collars (from a Femdom perspective)

All about collars (from a Femdom perspective)

MatureTubeHere 4 years 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

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

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