"Show all" option enabled

You might want to check our site IXXX.com for a better experience.

Undo

Sissy Training (264,323)

Making You Into a Sissy Maid Who Sucks Dick

Making You Into a Sissy Maid Who Sucks Dick

FapHouse 2 years ago

Tantaly : Chastity Release: The Last Penetration of your Life? Mistress Julia

Tantaly : Chastity Release: The Last Penetration of your Life? Mistress Julia

XHamster 2 years ago

Daily Sissy Training + Ruined orgasm JOI with S1monReilly

Daily Sissy Training + Ruined orgasm JOI with S1monReilly

AllBoner 3 years ago

Doll's trainning to throatfuck with silicone mask

Doll's trainning to throatfuck with silicone mask

XHamster 4 days ago

Just because I can..

Just because I can..

XHamster 2 years ago

My stepson Todd want to be my sissy girl

My stepson Todd want to be my sissy girl

XHamster 11 months ago

Slave fucking and dick locked in chastity belt

Slave fucking and dick locked in chastity belt

XHamster 2 years ago

Sophia Loreen Party on Jul 29, 2026 - Part 3

58% 4K 2:00 / 1:17:55

Sophia Loreen Party on Jul 29, 2026 - Part 3

Camster 2 months ago

Cum eating slut

63% HD 1:01 / 14:06

Cum eating slut

FapHouse 4 years ago

Chastity cage after a week of sissy training, dreaming of a daddy's cock

Chastity cage after a week of sissy training, dreaming of a daddy's cock

XHamster 3 years ago

Gf put her femboy in underwear to observe me fap off

Gf put her femboy in underwear to observe me fap off

TrannyGem 3 years ago

BBC Sissy Training

BBC Sissy Training

XHamster 1 month ago

Katy Ling Private Show

Katy Ling Private Show

Flirt4Free 1 week ago

Sophia Loreen Private Show

4K 2:00 / 12:33

Sophia Loreen Private Show

Flirt4Free 1 week ago

Anal Fingering

Flirt4Free 5 years ago

Salome Salvi Fucked Rough by 3 Asian Dommes with Strap-on

Salome Salvi Fucked Rough by 3 Asian Dommes with Strap-on

XHamster 1 month ago

Ambar Collingss Private Show

Ambar Collingss Private Show

Flirt4Free 2 weeks ago

JOI Anal session training, sissy lesson - Sammy Altham

JOI Anal session training, sissy lesson - Sammy Altham

XHamster 5 months ago

Mistress Susi - the Straight Slaves First Sissy Blowjob

57% 1:01 / 9:10

Mistress Susi - the Straight Slaves First Sissy Blowjob

FapHouse 1 month ago

becomingfemme - jeni justice fucks sissy princess deep inside her boipussy

becomingfemme - jeni justice fucks sissy princess deep inside her boipussy

TransDoe 2 years ago

Sissy Chanel Gets Anal Fucked with the Fucking Machine Hardcore

Sissy Chanel Gets Anal Fucked with the Fucking Machine Hardcore

XHamster 1 month ago

Evangeline Moon Private Show

Evangeline Moon Private Show

Flirt4Free 2 weeks ago

Nazanin Hunter Private Show

49% HD 2:00 / 19:16

Nazanin Hunter Private Show

Flirt4Free 2 years ago

Mistress Baton's Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training

Mistress Baton's Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training

XHamster 9 months ago

oubliette films - goddess serena pegging her sissy slaves boi pussy

oubliette films - goddess serena pegging her sissy slaves boi pussy

BDSMShip 3 years ago

Locked and Teased

HD 0:39 / 16:16

Locked and Teased

FapHouse 5 months ago

Huge Horny Tits vol 8

Huge Horny Tits vol 8

XHamster 2 years ago

Chastity For Life - Permanent Chastity Tattooed Sissy Slave Enslaved Slut Owned by Goddess Kyaa - 1080p MP4

69% 4K 0:24 / 12:43

Chastity For Life - Permanent Chastity Tattooed Sissy Slave Enslaved Slut Owned by Goddess Kyaa - 1080p MP4

Clips4sale 2 years ago

This babe widen Her Snatch wide to be happy by Her Sissy in swimsuit and tights

This babe widen Her Snatch wide to be happy by Her Sissy in swimsuit and tights

MatureTubeHere 2 years ago

Anal Training with Katie Fox

60% 1:01 / 12:33

Anal Training with Katie Fox

FapHouse 6 years ago

TS Fetishista

70% HD 1:01 / 21:58

FapHouse 8 years ago

SISSY TRAINING MINDFUCK FEMDOM

SISSY TRAINING MINDFUCK FEMDOM

Itsrealamateurs 3 months ago

Sissygasm Training

Sissygasm Training

XHamster 2 years ago

Dayla Smith Private Show

HD 2:00 / 27:42

Dayla Smith Private Show

Flirt4Free 1 week ago

Femboy Cumdump Pushes out Gallons of Cum

Femboy Cumdump Pushes out Gallons of Cum

XHamster 2 years ago

Sissy Slave Training

HD 0:39 / 13:18

Sissy Slave Training

FapHouse 1 week ago

POV changing flat chastity with urethral plug to small chastity cage

POV changing flat chastity with urethral plug to small chastity cage

XHamster 2 years ago

How to turn a Man into a willing Sissy

How to turn a Man into a willing Sissy

Clips 1 week ago

Corrine Dittmann Private Show

53% 4K 2:00 / 5:04

Corrine Dittmann Private Show

Flirt4Free 1 year ago

Railed Hard with Massive Dildo

HD 1:01 / 12:07

Railed Hard with Massive Dildo

FapHouse 4 days ago

Dressed in White and Ready to Submit

Dressed in White and Ready to Submit

XHamster 11 months ago

Sissy Stuffing Perverted Tasks for Feminization Gay Training

Sissy Stuffing Perverted Tasks for Feminization Gay Training

FapHouse 1 month ago

sissypov - mature sissy kati finnish swallowed all his cum

sissypov - mature sissy kati finnish swallowed all his cum

TransDoe 3 years ago

Sophia Loreen Private Show - Part 2

57% HD 2:00 / 10:36

Sophia Loreen Private Show - Part 2

Flirt4Free 5 months ago

Maya’s Back for Your Ass

63% VR 0:08 / 3:00

Maya’s Back for Your Ass

FapHouse 11 months ago

Kevin & Patric & Stivens Private Show

HD 2:00 / 28:16

Kevin & Patric & Stivens Private Show

Flirt4Free 3 years ago

Bentley Banghardt Private Show

66% HD 2:00 / 25:48

Bentley Banghardt Private Show

Flirt4Free 2 years ago

becoming femme - gwen how could you look at this and want a pussy after porn video

becoming femme - gwen how could you look at this and want a pussy after porn video

TransDoe 1 year ago

CBT with Sounds

CBT with Sounds

FapHouse 2 days ago

Sarait Gil Private Show

61% HD 2:00 / 6:20

Sarait Gil Private Show

Flirt4Free 2 years ago

Crossdressing gay torn up in the bootie

Crossdressing gay torn up in the bootie

TrannyGem 1 year ago

Angel Joseph Private Show

63% HD 2:00 / 4:59

Angel Joseph Private Show

Flirt4Free 1 week ago

They Must Suck Each Other's Cocks

They Must Suck Each Other's Cocks

XHamster 1 year ago

Heartless BBW Female-master Destroys Stepson CBT Boots, Deep Gagging, Anal Stretching, Sissification and Piddle Drinking!

Heartless BBW Female-master Destroys Stepson CBT Boots, Deep Gagging, Anal Stretching, Sissification and Piddle Drinking!

PornFreeNow 3 months ago

Worthless sissy slave gets her tight ass ponded by mistress's BBC

Worthless sissy slave gets her tight ass ponded by mistress's BBC

XHamster 10 months ago

Renounce Your Gods

Renounce Your Gods

XHamster 5 months ago

Sissy Big Cock Worship Training

Sissy Big Cock Worship Training

Pornicom 6 years ago

April Benson Private Show

63% HD 2:00 / 19:23

April Benson Private Show

Flirt4Free 2 years ago

Elvis & Stuard & Owen Private Show

44% HD 2:00 / 14:48

Elvis & Stuard & Owen Private Show

Flirt4Free 3 years ago

Femdom Strict Sissy Training Session: Cock Sucking, CBT, Pegging & Fisting with Mistress Stellina (1080p)

HD 0:39 / 54:59

Femdom Strict Sissy Training Session: Cock Sucking, CBT, Pegging & Fisting with Mistress Stellina (1080p)

FapHouse 1 month ago

Strap-on fucking and latex sissy training: a day in the life of a Matriarch Ezada Sinn’s sissy husband

Premium HD 15:10

Strap-on fucking and latex sissy training: a day in the life of a Matriarch Ezada Sinn’s sissy husband

Clips4sale 3 months ago

Sissy White T-Woman Lucy in V-Card Anal Invasion Nail by ten Inch BIG BLACK COCK Black Bull

Sissy White T-Woman Lucy in V-Card Anal Invasion Nail by ten Inch BIG BLACK COCK Black Bull

TrannyGem 4 years ago

Dirty Talk Slave Do What I told You Now be Polite Nice Sissy Sexy Accent Come Lick My Pussy And Feet

Dirty Talk Slave Do What I told You Now be Polite Nice Sissy Sexy Accent Come Lick My Pussy And Feet

Fapcat 4 years ago

The Mistress Plays with the Crossdresser as if He Were a Human Toy

The Mistress Plays with the Crossdresser as if He Were a Human Toy

XHamster 11 months ago

Caged up and Lost the Key

Caged up and Lost the Key

XHamster 3 months ago

She Fucks Him Hard Femdom Pegging Husband in Chastity

She Fucks Him Hard Femdom Pegging Husband in Chastity

XHamster 1 week ago

Mistress Lilith Destroys My Ass

66% HD 1:01 / 19:05

Mistress Lilith Destroys My Ass

FapHouse 7 months ago

Step Mama Trains U How to Be A Sissy Weenie Sucker (Humiliation) Jessica Bloom

Step Mama Trains U How to Be A Sissy Weenie Sucker (Humiliation) Jessica Bloom

ShemaleSin 3 years ago

Slutty Asian Femboy in Qipao Gets Red Ass Spanking, Deep Doggy Pounding & Merciless Fucking Machine Training

Slutty Asian Femboy in Qipao Gets Red Ass Spanking, Deep Doggy Pounding & Merciless Fucking Machine Training

XHamster 4 months ago

Sissy training you my slave, strap on and a sext Tranny, its yor dream, isnt it slave? ;) xx

70% 4K 0:50 / 24:39

Sissy training you my slave, strap on and a sext Tranny, its yor dream, isnt it slave? ;) xx

Clips4sale 4 months ago

Edging and Sounding by Dominafire

60% 0:39 / 24:43

Edging and Sounding by Dominafire

FapHouse 2 years ago

CUM BLOCKING HANDJOB. Female POV

CUM BLOCKING HANDJOB. Female POV

XHamster 4 years ago

She Trains Her Sissy Friend to Receive Cocks

She Trains Her Sissy Friend to Receive Cocks

FapHouse 1 year ago

GIGANTIC Ding-Dong Pegging for Chastity Sissy Thrall Destroying her Sexually Excited Gap by Mastix Mercer

GIGANTIC Ding-Dong Pegging for Chastity Sissy Thrall Destroying her Sexually Excited Gap by Mastix Mercer

ShemaleSin 5 years ago

Feelipe & Adara Private Show

65% HD 2:00 / 7:06

Feelipe & Adara Private Show

Flirt4Free 1 year ago

FEMALE-DOM PEGGING CHASTITY FAGGOT

FEMALE-DOM PEGGING CHASTITY FAGGOT

SortPorn 4 years ago

Sissy Anal Invasion Fuckslut Locked Down on Giant Fake Penis One Pub Jail Strapped & Taunted in Virginity Box by Domme

Sissy Anal Invasion Fuckslut Locked Down on Giant Fake Penis One Pub Jail Strapped & Taunted in Virginity Box by Domme

TrannyGem 3 years ago

Milton Jake Private Show

Milton Jake Private Show

Flirt4Free 3 years ago

Spanking My Sissybitch

Spanking My Sissybitch

FapHouse 6 days ago

Vends-ta-culotte - Anal training with your hot teacher who makes you her little slut

Vends-ta-culotte - Anal training with your hot teacher who makes you her little slut

XHamster 9 months ago

Fat Assed Sissy Slut rips open new lingerie, TWERKS BIG BOOTY, RIDES DILDO HARRD & SISSYGASMS!

Fat Assed Sissy Slut rips open new lingerie, TWERKS BIG BOOTY, RIDES DILDO HARRD & SISSYGASMS!

XHamster 4 years ago

More Tasks for your Sissy Training | Femdom Goddess Nikki Kit

More Tasks for your Sissy Training | Femdom Goddess Nikki Kit

Itsrealamateurs 2 weeks ago

the gift - futa femboy pt 2

the gift - futa femboy pt 2

HentaiGem 4 years ago

Arab Sissy Crossdresser Pummeled by BIG BLACK COCK Father & Cum shot

Arab Sissy Crossdresser Pummeled by BIG BLACK COCK Father & Cum shot

TransTube.tv 2 years ago

Pornstar Ria Bentley Takes Giant BBC On Public Hotel Balcony

Pornstar Ria Bentley Takes Giant BBC On Public Hotel Balcony

XHamster 1 year ago

FEMDOM SISSY TRAINING

FEMDOM SISSY TRAINING

LoyalFans 1 year ago

Max Conorr Private Show

63% 4K 2:00 / 8:03

Max Conorr Private Show

Flirt4Free 1 year ago

Sissy Jessica Bloom Spitroast Training With Fucking Machine And Dildos - Anal Sissygasms and Cumswallow

Sissy Jessica Bloom Spitroast Training With Fucking Machine And Dildos - Anal Sissygasms and Cumswallow

XHamster 6 months ago

He Fucks Me Like a Bitch... I Love Being Trained by Master

He Fucks Me Like a Bitch... I Love Being Trained by Master

XHamster 4 months ago

Carolina Betancur Private Show

HD 2:00 / 29:17

Carolina Betancur Private Show

Flirt4Free 1 month ago

Seduced By GF's Sorority Sisters: Part 2

Seduced By GF's Sorority Sisters: Part 2

Some.Porn 11 months ago

2 Cocks 1 Slut - Sissy Slut Training !

2 Cocks 1 Slut - Sissy Slut Training !

IWantClips 4 months ago

Threesome for My T Girl Friend, I Lend Her My 2 Favorite Big Spermy Cocks

59% 0:39 / 14:02

Threesome for My T Girl Friend, I Lend Her My 2 Favorite Big Spermy Cocks

FapHouse 2 years ago

Hong Kong milf queen trains sissy teacher in big ass humiliation

Hong Kong milf queen trains sissy teacher in big ass humiliation

AveXXX 2 months ago

Elizabeth Whiler Private Show

46% HD 2:00 / 9:05

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

Cummy Classroom Sissy Slut Tgirl Panty Loads

58% 0:11 / 14:08

Cummy Classroom Sissy Slut Tgirl Panty Loads

Clips4sale 3 years ago

suck and dirty show

46% HD 2:00 / 14:52

suck and dirty show

Flirt4Free 2 years ago

Trained to Be a Submissive Slut

Trained to Be a Submissive Slut

AShemaleTube 1 year ago

Size Queen Sissy Male Training with CEI

Size Queen Sissy Male Training with CEI

BigTitsLust 3 months ago

Riding in the Blue Cheerleading Outfit BBC

Riding in the Blue Cheerleading Outfit BBC

XHamster 3 months ago

Feminization night

HD 1:01 / 11:17

Feminization night

FapHouse 8 years ago

Sissy Whore Training POV

58% HD 0:39 / 6:21

Sissy Whore Training POV

FapHouse 1 year ago

insatiable Milky twunk bonks dark Fem W Facial Cumshot

insatiable Milky twunk bonks dark Fem W Facial Cumshot

Gay4Porn 5 years ago

Ass Slut Training JOI

Ass Slut Training JOI

PornFreeNow 1 day ago

Amber Fletcher Private Show

54% HD 2:00 / 21:13

Amber Fletcher Private Show

Flirt4Free 2 years ago

Putting Big Toys in a Sissy Butt Hole - Regular Anal Traning for Tiffany with Mistress J

Putting Big Toys in a Sissy Butt Hole - Regular Anal Traning for Tiffany with Mistress J

FapHouse 1 year ago

Soft Cock Training By Doctor Nicole (Prone Masturbation JOI)

Soft Cock Training By Doctor Nicole (Prone Masturbation JOI)

Clips4sale 10 months ago

Sissy Quiz

45% HD 0:18 / 24:11

IWantClips 3 years ago

Big Dildo Hits the P SPOT Cumshot

Big Dildo Hits the P SPOT Cumshot

XHamster 2 years ago

Vanessa Mancini Private Show

Vanessa Mancini Private Show

Flirt4Free 3 years ago

Balloons and Nude

Balloons and Nude

XHamster 3 weeks ago

U wear panties & suck cock for me! Sissy training femdom!

U wear panties & suck cock for me! Sissy training femdom!

Itsrealamateurs 2 weeks ago

Angel Joseph Private Show

Angel Joseph Private Show

Flirt4Free 7 months ago

POV Cuckold volume 45

POV Cuckold volume 45

XHamster 5 years ago

Petra's porno marathon part 1-3

Petra's porno marathon part 1-3

XHamster 1 year ago

Finger fucked slut - sissy hole stretching

70% 0:30 / 10:11

Finger fucked slut - sissy hole stretching

Clips4sale 2 years ago

Making My Husband into a Cuckold Sissy!

50% 0:11 / 9:49

Making My Husband into a Cuckold Sissy!

Clips4sale 3 years ago

Ronnie Cranfort Private Show

65% HD 2:00 / 18:04

Ronnie Cranfort Private Show

Flirt4Free 4 years ago

Rubberdoll at the Bizarre Clinic Part 4 / Censored version without Goldenshower

48% HD 0:10 / 5:32

Rubberdoll at the Bizarre Clinic Part 4 / Censored version without Goldenshower

LoyalFans 1 year ago

Two Cocks One Sissy

Two Cocks One Sissy

Clips4sale 2 years ago

18 19 20 21 22

264,323 results found

Narrow your search

sissy anal training

Categories Pornstars

Parents

Pornhd.com uses the “Restricted To Adults” (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Pornhd.com. All rights reserved.

© 2026 Pornhd.com. All rights reserved.