Sissy Training Videos (79,830)

P8 3SOME TV SLUT PURE BAREBACK WITH FETISHTRANSEXUAL AND MASTER MIKE FULL DOMINATION

P8 3SOME TV SLUT PURE BAREBACK WITH FETISHTRANSEXUAL AND MASTER MIKE FULL DOMINATION

Clips4sale 1 year ago

Psycho Transgirl Captures Her Bully for Christmas

HD 0:26 / 12:03

Psycho Transgirl Captures Her Bully for Christmas

IWantClips 1 month ago

Blond Trans Samus Cosplay Anal Creampie Blacked and Booty Destroyed by 2 Large Ebony Dicks

Blond Trans Samus Cosplay Anal Creampie Blacked and Booty Destroyed by 2 Large Ebony Dicks

ShemaleSin 2 months ago

Spanking in Bondage - Sissy Slave Gets a Lesson From Her Mistress

Spanking in Bondage - Sissy Slave Gets a Lesson From Her Mistress

XHamster 6 months ago

Mature tranny teaches her maid to be a good shemale slut

Mature tranny teaches her maid to be a good shemale slut

Fapality 2 years ago

Ladyboy training

Ladyboy training

XHamster 3 years ago

Rope bondage, shibari. Dominatrix Nika ties up her Sissy Blaire_18 with ropes and plays with her slender body.

Rope bondage, shibari. Dominatrix Nika ties up her Sissy Blaire_18 with ropes and plays with her slender body.

XHamster 8 months ago

Crossdresser buttfucking

Crossdresser buttfucking

ShemaleSin 1 week ago

Stellar sissy Ponyboy Displaying his bare bod and high stilettos

Stellar sissy Ponyboy Displaying his bare bod and high stilettos

TrannyGem 4 years ago

Hinako's First Female Suit Experience (Hinako Version)!

HD 0:11 / 22:25

Hinako's First Female Suit Experience (Hinako Version)!

Clips4sale 4 years ago

Skinny Blond Whiteboi Bitch Jes Exposed

Skinny Blond Whiteboi Bitch Jes Exposed

XHamster 3 months ago

futa femdom sissy self-sucking facial and pegging - SD

futa femdom sissy self-sucking facial and pegging - SD

Clips4sale 3 years ago

Feminization Counseling

HD 0:15 / 12:44

Feminization Counseling

IWantClips 6 years ago

Lika Kai Private Show

Lika Kai Private Show

Camster 6 days ago

Anal Big Booty Loves Cock Toy

Anal Big Booty Loves Cock Toy

XHamster 1 year ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 2 weeks ago

1st Day as Trans Sissy Sex Thrall – Group-sex Training

1st Day as Trans Sissy Sex Thrall – Group-sex Training

BigTitsLust 2 months ago

Finale: Rectal fuck stick plumb with spandex socks 20210801-six

Finale: Rectal fuck stick plumb with spandex socks 20210801-six

TrannyGem 4 years ago

Indian Gay Crossdresser Bottom Pressing and Playing with Her Big Boobs in Black Saree Real Homemade XXX Sex

Indian Gay Crossdresser Bottom Pressing and Playing with Her Big Boobs in Black Saree Real Homemade XXX Sex

FapHouse 5 months ago

Machine Anal Training

Machine Anal Training

XHamster 6 months ago

Duct Tape on My Mouth

HD 2:00 / 11:45

Duct Tape on My Mouth

Flirt4Free 8 months ago

The maid whore

XHamster 1 year ago

Home Masturbation

Home Masturbation

XHamster 2 months ago

Luziatv, I Feel on Your Dick. Shall We Cum Together?

Luziatv, I Feel on Your Dick. Shall We Cum Together?

XHamster 2 months ago

You must be dying to become my sissy slut

You must be dying to become my sissy slut

XHamster 11 years ago

Brutus K Body Showing

Brutus K Body Showing

Flirt4Free 11 years ago

”How To Eat your Goddess Snatch #FemdomRAW”

”How To Eat your Goddess Snatch #FemdomRAW”

IFuckedYourGF 1 year ago

Viky & Emma Private Show

62% HD 2:00 / 8:31

Viky & Emma Private Show

Flirt4Free 6 months ago

Sara & Elver Private Show

62% HD 2:00 / 14:48

Sara & Elver Private Show

Flirt4Free 8 months ago

The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)

62% HD 0:39 / 7:20

The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)

FapHouse 10 months ago

Luciana Sainz Private Show

Luciana Sainz Private Show

Flirt4Free 5 months ago

Hattabi4ik Sissy Fellow Getting Off Compilation

Hattabi4ik Sissy Fellow Getting Off Compilation

TrannyGem 3 years ago

FPOV Sissy Oral sex Close Up

FPOV Sissy Oral sex Close Up

ShemaleSin 2 years ago

BBC Anal in Doggy with Sissy Hotty KimsaTrans

BBC Anal in Doggy with Sissy Hotty KimsaTrans

ShemaleSin 5 years ago

Permanent Feminization ft Goddess Colleen

Permanent Feminization ft Goddess Colleen

TransTube.tv 1 year ago

Sissy teasing and dildo riding on balcony

Sissy teasing and dildo riding on balcony

XHamster 11 months ago

Sissy to Cock Sucker Pipeline- Bisexual Feminization Mindfuck

HD 0:25 / 10:14

Sissy to Cock Sucker Pipeline- Bisexual Feminization Mindfuck

IWantClips 1 year ago

Nylon Sissy Slut Michelle Wakeup Training for the Show at Beijing Hotel

Nylon Sissy Slut Michelle Wakeup Training for the Show at Beijing Hotel

XHamster 1 year ago

Christian & Oliver & Matt Private Show

HD 2:00 / 21:44

Christian & Oliver & Matt Private Show

Flirt4Free 3 years ago

Costume held up by bag, I didn't notice

Costume held up by bag, I didn't notice

ShemaleSin 2 years ago

Sissy nurse does assfucking with a orgy machine and jizm with faux-cock in the culo . Sissyfication crossdresser

Sissy nurse does assfucking with a orgy machine and jizm with faux-cock in the culo . Sissyfication crossdresser

TrannyGem 3 years ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 1 year ago

Parking Garage Wench

Parking Garage Wench

ShemaleSin 1 year ago

Step-Mommy's Lessons Part 2 (UNCENSORED)

Step-Mommy's Lessons Part 2 (UNCENSORED)

Clips4sale 2 years ago

Large, long, manstick in my sugary-sweet donk

Large, long, manstick in my sugary-sweet donk

TransTube.tv 1 year ago

Micah Filipina Private Show

HD 2:00 / 13:40

Micah Filipina Private Show

Flirt4Free 2 years ago

Honeymoon Cuckold

41% 0:30 / 19:33

Honeymoon Cuckold

Clips4sale 1 year ago

How to Teach Your Sissy Boyfriend

How to Teach Your Sissy Boyfriend

ShemaleSin 8 months ago

AmberSis - Pink Sissy Cock Slut

AmberSis - Pink Sissy Cock Slut

Eporner 6 years ago

hard crossdresser pegging. fuck anal with two dildo and fisting. big dildo sissy humiliation

HD 0:30 / 15:09

hard crossdresser pegging. fuck anal with two dildo and fisting. big dildo sissy humiliation

PornBox 3 years ago

Sissy Cum From Anal Dildo

Sissy Cum From Anal Dildo

XHamster 3 months ago

Pantied Sissy JOI

70% HD 0:10 / 11:55

Pantied Sissy JOI

LoyalFans 1 year ago

Bent over sissy gets pegged whilst his balls hang like a worthless fucking bitch

Bent over sissy gets pegged whilst his balls hang like a worthless fucking bitch

XHamster 1 year ago

Filling the Sissy Ashole with Her Own Cum After a Hard Fisting by Mistress Hands

HD 1:01 / 10:54

Filling the Sissy Ashole with Her Own Cum After a Hard Fisting by Mistress Hands

FapHouse 10 months ago

Sissy slave Oksana shows her master sissygasms from anal training on a big black dildo

Sissy slave Oksana shows her master sissygasms from anal training on a big black dildo

XHamster 3 years ago

Madelaine Marquez Private Show

HD 2:00 / 11:47

Madelaine Marquez Private Show

Flirt4Free 4 months ago

Exposed Sissy Shiera - Shiera Trains And Gapes Her Boy Pussy

Exposed Sissy Shiera - Shiera Trains And Gapes Her Boy Pussy

Eporner 2 weeks ago

Tatiana & Lord Private Show

Tatiana & Lord Private Show

Flirt4Free 2 weeks ago

His Personal Fucktoy

66% 1:01 / 23:00

His Personal Fucktoy

FapHouse 9 months ago

Nicolle & Christian Private Show

Nicolle & Christian Private Show

Camster 1 year ago

Turning the Str8 u into a HOMOSEXUAL sissy Cumslut

Turning the Str8 u into a HOMOSEXUAL sissy Cumslut

MatureTubeHere 5 years ago

Sissy Crossdresser Cat Walk Training

Sissy Crossdresser Cat Walk Training

XHamster 1 year ago

Double Master Sissy Lapdance

Double Master Sissy Lapdance

XHamster 1 year ago

Master & Christian Mckenzie & Christian Rey Private Show

HD 2:00 / 1:14:39

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 3 years ago

Sophia Loreen Party on Jun 23, 2026 - Part 4

HD 2:00 / 35:23

Sophia Loreen Party on Jun 23, 2026 - Part 4

Flirt4Free 1 month ago

HornyEmpressKay - 30 CUM SHOTS THE BEVY 1,two,trio

HornyEmpressKay - 30 CUM SHOTS THE BEVY 1,two,trio

TrannyGem 4 years ago

Jess Bloom Shows How to Come From Riding a Sextoy Like a Admirable Bitch Spraying Multiple Cumshots and Licking Up Each Drop

Jess Bloom Shows How to Come From Riding a Sextoy Like a Admirable Bitch Spraying Multiple Cumshots and Licking Up Each Drop

ShemaleSin 2 months ago

SISSY TRAINING (rus Sub)

SISSY TRAINING (rus Sub)

TrannyGem 7 years ago

Jasmine Dlight & Mistress Luciana - VR Shoulder Deep Anal Fisting & Gape

61% VR 0:08 / 2:19

Jasmine Dlight & Mistress Luciana - VR Shoulder Deep Anal Fisting & Gape

FapHouse 5 months ago

lady sobs as she is impregnated by a pony-sized faux-cock

lady sobs as she is impregnated by a pony-sized faux-cock

TrannyGem 2 years ago

FemDom Session: Training and humiliation of a Sissy

FemDom Session: Training and humiliation of a Sissy

AbTranny 7 years ago

Vladasexytrans suck masturbate and cum

Vladasexytrans suck masturbate and cum

XHamster 2 years ago

Pee play with HARD ANAL and triple cum!

Pee play with HARD ANAL and triple cum!

ShemaleSin 3 years ago

Sissy Hole Training

Sissy Hole Training

Xfeed 3 years ago

Gretta Lee Private Show

Gretta Lee Private Show

Flirt4Free 5 days ago

Feminized Irreversibly

66% 0:11 / 8:38

Feminized Irreversibly

Clips4sale 3 years ago

Domme is daydreaming about opening up your cock-squeezing shagging boypussy (FEMINIZATION ROLEPLAY - AI GENERATED)

Domme is daydreaming about opening up your cock-squeezing shagging boypussy (FEMINIZATION ROLEPLAY - AI GENERATED)

HentaiGem 1 year ago

Helena Miles Private Show

Helena Miles Private Show

Flirt4Free 4 years ago

Femboy Tramp Ass-Fuck Instructing in Milky Stocking ~oscar20xxx~

Femboy Tramp Ass-Fuck Instructing in Milky Stocking ~oscar20xxx~

GayCK 6 years ago

Alexandra Silex Private Show

4K 2:00 / 14:09

Alexandra Silex Private Show

Flirt4Free 1 year ago

Showing of Body Feeling Horny After Night at Club

Showing of Body Feeling Horny After Night at Club

XHamster 2 months ago

Look at This Sissy Playing Dress-up

Look at This Sissy Playing Dress-up

XHamster 3 months ago

BBC dildo training

BBC dildo training

AShemaleTube 2 years ago

Dani Saenz Private Show

HD 2:00 / 1:56:38

Dani Saenz Private Show

Camster 2 years ago

thick knockers mega-slut mega-bitch used by Domme SADISM & MASOCHISM condom-free blowjob buttfuck spunk pee mass ejaculation internal cumshot fuck stick going knuckle deep

thick knockers mega-slut mega-bitch used by Domme SADISM & MASOCHISM condom-free blowjob buttfuck spunk pee mass ejaculation internal cumshot fuck stick going knuckle deep

TrannyGem 1 year ago

Genesis Hall Private Show

Genesis Hall Private Show

Flirt4Free 2 years ago

Diaper Satin Sissy Halloween Humiliation

66% HD 0:30 / 15:51

Diaper Satin Sissy Halloween Humiliation

Clips4sale 10 months ago

MY STEP PARENT PORKS ME AND MAKES ME SPUNK

MY STEP PARENT PORKS ME AND MAKES ME SPUNK

TrannyGem 3 years ago

Washing machine joy

Washing machine joy

TrannyGem 1 year ago

Chastity Sissy Maid Service Training With Ria Bentley

Chastity Sissy Maid Service Training With Ria Bentley

ShemaleSin 9 months ago

Piss Enema Release and Fisting for Sissy Slut

65% HD 0:32 / 17:11

Piss Enema Release and Fisting for Sissy Slut

Clips4sale 9 months ago

Foot Show

51% 4K 2:00 / 16:09

Flirt4Free 4 months ago

Asian Sissy Tied Up Cum With Vibrator

Asian Sissy Tied Up Cum With Vibrator

XHamster 2 years ago

SADISTIC DOMME PROGRAMMED YOUR BRAIN INTO FEMINIZATION - Feminization Training

SADISTIC DOMME PROGRAMMED YOUR BRAIN INTO FEMINIZATION - Feminization Training

Clips4sale 1 year ago

Patric & Oliver Private Show

Patric & Oliver Private Show

Flirt4Free 3 years ago

Dressing My Sissy BFF on Our Cruise

54% HD 0:09 / 12:15

Dressing My Sissy BFF on Our Cruise

Clips4sale 4 years ago

I'll Make You My Perfect Sissy Girlfriend

I'll Make You My Perfect Sissy Girlfriend

Clips4sale 2 years ago

Huge anal insertion compilation

Huge anal insertion compilation

XHamster 8 months ago

Sissy Cop leaking cum from her cage

Sissy Cop leaking cum from her cage

XHamster 3 years ago

forceps from my senior smartphone four

forceps from my senior smartphone four

5Gays 8 months ago

Emery Lune Anal Solo Play Vol Ii

67% HD 1:01 / 44:06

Emery Lune Anal Solo Play Vol Ii

FapHouse 2 months ago

Creating A New Feminized Doll Stage 1 (MP4)

55% 0:13 / 16:34

Creating A New Feminized Doll Stage 1 (MP4)

Clips4sale 11 months ago

Making You Eat Fat Tranny Jizz

60% HD 0:25 / 10:57

Making You Eat Fat Tranny Jizz

Clips4sale 2 years ago

Sissy Wife Blowjob Practice - Clara Dee JOI

62% HD 1:01 / 15:05

Sissy Wife Blowjob Practice - Clara Dee JOI

FapHouse 2 years ago

Zara Clark Private Show

4K 2:00 / 25:28

Zara Clark Private Show

Camster 9 months ago

Lexxie Paige Private Show

Lexxie Paige Private Show

Camster 9 months ago

Sissy Training - Guide to became Sissy - (No_1)

Sissy Training - Guide to became Sissy - (No_1)

ShemaleSin 5 years ago

RED-HOT T-MODELS COMPILATION STAMINA COMPETE - Can you make it to the end ?

RED-HOT T-MODELS COMPILATION STAMINA COMPETE - Can you make it to the end ?

TrannyGem 11 months ago

Lovely lil trap rectal instructing

Lovely lil trap rectal instructing

TrannyGem 4 years ago

Alice Hottets Private Show

Alice Hottets Private Show

Flirt4Free 3 years ago

Spider Woman Its Ready!

Spider Woman Its Ready!

Camster 3 years ago

Having a Hard Time - Shemale Jane Dreams of Fucking Larissa in Front of Noah & Farah

HD 0:39 / 10:32

Having a Hard Time - Shemale Jane Dreams of Fucking Larissa in Front of Noah & Farah

FapHouse 1 month ago

Micah Filipina Private Show

Micah Filipina Private Show

Flirt4Free 2 years ago

Throat Fucked by Giant Cock Again, Always so Horny.

Throat Fucked by Giant Cock Again, Always so Horny.

FapHouse 1 year ago

$Up Close Brutus\'s Uncut Dick and Low Hanging Balls$ 57% HD 2:00 / 9:46

Up Close Brutus\'s Uncut Dick and Low Hanging Balls

Flirt4Free 9 years ago

My anal riding compilation

My anal riding compilation

XHamster 2 years ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 2 weeks ago

Kept by Jessica Blake Part 4

Kept by Jessica Blake Part 4

XHamster 4 months ago

Slap My Horny Ass ^^

Slap My Horny Ass ^^

Flirt4Free 1 year ago

SKINNY LADYBOY ANAL CASTING, SLAVE TRAINING AND CREAM ENEMA

Premium HD 32:05

SKINNY LADYBOY ANAL CASTING, SLAVE TRAINING AND CREAM ENEMA

XVideosRed 1 year ago

68 69 70 71 72

79,830 results found

Narrow your search

sissy anal training

Categories Pornstars

Parents

Pornmd.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 Pornmd.com. All rights reserved.

© 2026 Pornmd.com. All rights reserved.