Training Videos - Trans (124,196)

Xl Inflatable Plug Inside a Femboy's Butt

Xl Inflatable Plug Inside a Femboy's Butt

FapHouse 2 years ago

Lena Pauline Private Show

Lena Pauline Private Show

Flirt4Free 3 years ago

Sexy Caged Crossdresser gets anal pussy stretched out to the MAX

Sexy Caged Crossdresser gets anal pussy stretched out to the MAX

XHamster 1 year ago

Трахаю рукой и кабачком свою sissy шлюху. После чего она лижет жопу и пьет мочу со своей спермой

Трахаю рукой и кабачком свою sissy шлюху. После чего она лижет жопу и пьет мочу со своей спермой

TrannyGem 3 years ago

Bnwo Sissy

53% HD 0:39 / 2:19

FapHouse 1 year ago

My Sissy Sucks My Locked Husband… Who Thinks It’s Me - Mistress Julia

65% 1:01 / 12:15

My Sissy Sucks My Locked Husband… Who Thinks It’s Me - Mistress Julia

FapHouse 10 months ago

Sasha De Sade Sissy Inspection Hot!

Sasha De Sade Sissy Inspection Hot!

TrannyGem 7 years ago

A Whore Offers Herself to Cocks in La Belle & Les Clochards

A Whore Offers Herself to Cocks in La Belle & Les Clochards

XHamster 3 months ago

Slave for tranny girl! After beach jogging there are sweaty socks and feet for his mouth!

Slave for tranny girl! After beach jogging there are sweaty socks and feet for his mouth!

XHamster 2 years ago

plopping my little nutsack into hot fucking ass wax

55% 0:15 / 5:03

plopping my little nutsack into hot fucking ass wax

AnalVids 2 weeks ago

Sophia Loreen Private Show

4K 2:00 / 10:20

Sophia Loreen Private Show

Flirt4Free 1 year ago

You're My New Bitch Today - Intense Sissy Training

55% HD 1:01 / 35:56

You're My New Bitch Today - Intense Sissy Training

FapHouse 3 weeks ago

Playtime for Mister K

54% HD 2:00 / 23:54

Playtime for Mister K

Flirt4Free 11 years ago

Mike Swift & David Golden Private Show

62% HD 2:00 / 8:21

Mike Swift & David Golden Private Show

Flirt4Free 2 months ago

Trix Bell Private Show

66% 4K 2:00 / 10:54

Trix Bell Private Show

Camster 1 year ago

Sophia Loreen Party on Sep 9, 2026 - Part 3

67% 4K 2:00 / 29:56

Sophia Loreen Party on Sep 9, 2026 - Part 3

Flirt4Free 2 weeks ago

Sissy Shiera Full Livestream Goon Session

Sissy Shiera Full Livestream Goon Session

Eporner 1 week ago

fastened up transgirl with oral machine and vibrating plug struggles to focus on game

fastened up transgirl with oral machine and vibrating plug struggles to focus on game

ShemaleSin 5 months ago

TS Training

67% HD 1:01 / 21:41

FapHouse 1 year ago

ANAL FUCK Tranny Skeletor Ass Licking SPUNK SWALLOWER AssHole Banged by Nasty Pervert Penis!

ANAL FUCK Tranny Skeletor Ass Licking SPUNK SWALLOWER AssHole Banged by Nasty Pervert Penis!

XHamster 3 years ago

S01e05 the Slutty Adventures of Neetrasurik

63% HD 0:39 / 6:14

S01e05 the Slutty Adventures of Neetrasurik

FapHouse 1 year ago

Exhibitionist Domme & Humiliated Sub: Queen Elena Flashes, Then Gags & Walks Sissy Femme Sandy

46% 1:01 / 5:38

Exhibitionist Domme & Humiliated Sub: Queen Elena Flashes, Then Gags & Walks Sissy Femme Sandy

FapHouse 7 months ago

Petite Emo White Trans Girl with Big Puffy Nipples Sucks and Milks Them with a Vacuum Pump

69% HD 1:01 / 14:56

Petite Emo White Trans Girl with Big Puffy Nipples Sucks and Milks Them with a Vacuum Pump

FapHouse 10 months ago

Sissy Femboy Shiera Gapes Boy Pussy In Sexy Blue Lingerie

Sissy Femboy Shiera Gapes Boy Pussy In Sexy Blue Lingerie

XHamster 1 month ago

Elias & Elix Private Show

44% HD 2:00 / 13:09

Elias & Elix Private Show

Flirt4Free 1 year ago

I'll guide you to become the sissy you were meant to be (FEMINIZATION ROLEPLAY - AI GENERATED)

I'll guide you to become the sissy you were meant to be (FEMINIZATION ROLEPLAY - AI GENERATED)

XHamster 1 year ago

Sophia Loreen Private Show

66% 4K 2:00 / 41:26

Sophia Loreen Private Show

Flirt4Free 1 month ago

Tatiana & Lord Private Show

55% HD 2:00 / 9:23

Tatiana & Lord Private Show

Camster 2 months ago

Part 1 My Husband Turned Into Latex Sissy Doll Good to Fuck - Mistress Julia

51% HD 0:39 / 12:50

Part 1 My Husband Turned Into Latex Sissy Doll Good to Fuck - Mistress Julia

FapHouse 1 year ago

Sophia Loreen Private Show

69% HD 2:00 / 6:21

Sophia Loreen Private Show

Flirt4Free 4 months ago

”GENDER X Shemale cheerleader rides on big black cock - Smash Thompson,Ella Hollywood”

”GENDER X Shemale cheerleader rides on big black cock - Smash Thompson,Ella Hollywood”

Fapnow 4 years ago

First time bareback gay sex with older man

First time bareback gay sex with older man

XHamster 2 years ago

Lisan & Mine Private Show

65% 4K 2:00 / 7:40

Lisan & Mine Private Show

Flirt4Free 1 month ago

Trans Girl *** Orgasm

58% HD 0:39 / 19:44

Trans Girl *** Orgasm

FapHouse 2 years ago

Brides Hands-free BBC Cumshots

Brides Hands-free BBC Cumshots

XHamster 2 months ago

Get railed fucking hard by your futanari girlfriend (Dildo JOI)

Get railed fucking hard by your futanari girlfriend (Dildo JOI)

XHamster 3 months ago

Rough Triple Anal Ride for Our Little Sissy

Rough Triple Anal Ride for Our Little Sissy

XHamster 3 days ago

Corssdresser intens anal orgasm during machine fucking

Corssdresser intens anal orgasm during machine fucking

XHamster 2 years ago

Happy Birthday Lola

Happy Birthday Lola

XHamster 3 months ago

Sapphire Dresses You in Her Uniform

63% HD 0:39 / 10:54

Sapphire Dresses You in Her Uniform

FapHouse 11 months ago

Sissy Training

XHamster 3 years ago

Girlfriend Catches You with Her Panties

Girlfriend Catches You with Her Panties

XHamster 1 month ago

Training My Ass with a Dildo and My Hand...

HD 0:39 / 23:19

Training My Ass with a Dildo and My Hand...

FapHouse 1 month ago

Attempting Fresh Knuckle Fuck stick and Get Plumbed and Fisted

Attempting Fresh Knuckle Fuck stick and Get Plumbed and Fisted

4Gay 1 year ago

Treat Me Like a Sissy-slut

50% HD 1:01 / 18:39

Treat Me Like a Sissy-slut

FapHouse 10 months ago

Best femdom pegging porn compilation

Best femdom pegging porn compilation

AnySex 2 years ago

You Are Not a Man Anymore - You Are My Feminized Sissy Girl - Asmr Transformation Clip by Findom Goaldigger

You Are Not a Man Anymore - You Are My Feminized Sissy Girl - Asmr Transformation Clip by Findom Goaldigger

XHamster 10 months ago

Swallow My Loads Sissy Trainer

HD 1:01 / 10:58

Swallow My Loads Sissy Trainer

FapHouse 4 months 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

Frederick & Aleex & Daaniel Private Show

58% HD 2:00 / 4:03

Frederick & Aleex & Daaniel Private Show

Flirt4Free 1 year ago

Sissy slut crossdresser gets dominated in sexy dress

Sissy slut crossdresser gets dominated in sexy dress

FapNFuck 1 year ago

Sophie Fantasy Private Show

59% HD 2:00 / 4:53

Sophie Fantasy Private Show

Flirt4Free 4 months ago

Luis & Raffaelo & Apolo Private Show

Luis & Raffaelo & Apolo Private Show

Flirt4Free 3 years ago

Jacob Malik Private Show

63% HD 2:00 / 15:29

Jacob Malik Private Show

Flirt4Free 7 months ago

Bondage Tit Slapping: Playwithkk's Expert Nipple Pinch Exam

Bondage Tit Slapping: Playwithkk's Expert Nipple Pinch Exam

FapHouse 1 month ago

Turning you into my Sissy Wife for your brand new Sissy Life

XHamster 1 week ago

Cum Factory Room 27

60% HD 1:01 / 13:18

Cum Factory Room 27

FapHouse 2 years ago

Sissy Jessica's Weekly Hole Training 1 (4k)

Sissy Jessica's Weekly Hole Training 1 (4k)

XHamster 1 month ago

Watch these hot babes go wild with deep dildos & cum in lingerie

Watch these hot babes go wild with deep dildos & cum in lingerie

TrannyMovs 1 week ago

You Are a Jerk Junkie Gooner, Mistress Humiliation

52% HD 1:01 / 17:35

You Are a Jerk Junkie Gooner, Mistress Humiliation

FapHouse 4 months ago

Petra the hardcore anal bitch (incl dap, tap, fisting and giant sex toy)

Petra the hardcore anal bitch (incl dap, tap, fisting and giant sex toy)

ShemaleSin 6 months ago

TS Natalie Mars trains Dr Pierce Paris how to be used like a slut

TS Natalie Mars trains Dr Pierce Paris how to be used like a slut

MenGem 9 months ago

Sexy sissy slut nun in chastity celebrates her slutty mass, begging to be blessed with lots of BBC to serve

Sexy sissy slut nun in chastity celebrates her slutty mass, begging to be blessed with lots of BBC to serve

XHamster 9 months ago

Queen of Sissies Gives Femdom Sissy Training

HD 1:01 / 25:40

Queen of Sissies Gives Femdom Sissy Training

FapHouse 5 days ago

I'm Not The Very first Obviously... A Private Sissy Whore as A Queen

I'm Not The Very first Obviously... A Private Sissy Whore as A Queen

WebcamBros 5 months ago

Sissy Husband Dressed in Pink, Pegged & Fed Him Own Cum!

70% HD 1:01 / 22:24

Sissy Husband Dressed in Pink, Pegged & Fed Him Own Cum!

FapHouse 1 year ago

How I Feel About Imposed Bi - Femdom POV

50% HD 1:01 / 12:57

How I Feel About Imposed Bi - Femdom POV

FapHouse 5 months ago

Dazuna Block Private Show

Dazuna Block Private Show

Flirt4Free 2 weeks ago

”Naughty Trans Pixi Lust submits to Draven Navarro for hardcore plowing”

”Naughty Trans Pixi Lust submits to Draven Navarro for hardcore plowing”

429Men 8 months ago

Turn Into My Dumb Bimbo Sissy - Lip - Sucking Asmr for Pretty Face Obsession Clip by Findom Goaldigger

HD 1:01 / 10:12

Turn Into My Dumb Bimbo Sissy - Lip - Sucking Asmr for Pretty Face Obsession Clip by Findom Goaldigger

FapHouse 10 months ago

Alexxa A Private Show

HD 2:00 / 11:28

Alexxa A Private Show

Flirt4Free 2 days ago

Nurse Eva dominates and instructs her patient in protection and big cock fun

Nurse Eva dominates and instructs her patient in protection and big cock fun

TrannyMovs 5 months ago

Bad Dragon Pounding and Gaping - original early web camera show by Mistresse Mercer

Bad Dragon Pounding and Gaping - original early web camera show by Mistresse Mercer

Lesbian8 3 months ago

Cute Trans Gwen Tennyson in Thong getting Anal Fucked through her Torn Leggings by Big Dildo

Cute Trans Gwen Tennyson in Thong getting Anal Fucked through her Torn Leggings by Big Dildo

XHamster 5 months ago

Vixen Goddess V - Goddess V's Chastity Cuckold Sissy Training: Humiliating Sph Locks & Feminine Makeover

Vixen Goddess V - Goddess V's Chastity Cuckold Sissy Training: Humiliating Sph Locks & Feminine Makeover

EpicGFs 1 month ago

Cock vs Pussy Goon Challenge PMV

Cock vs Pussy Goon Challenge PMV

Clips4sale 1 month ago

Eddy and Coach Studs - massage, bareback, squirting

69% 0:30 / 25:56

Eddy and Coach Studs - massage, bareback, squirting

Clips4sale 2 years ago

Shemale Deep Fuck with below job

Shemale Deep Fuck with below job

Tranny.one 4 years ago

Iron Fist’s Training Session

Iron Fist’s Training Session

ALOTPorn 1 week ago

Ambar & Lord Private Show

Ambar & Lord Private Show

Camster 2 weeks ago

Sissy Ass Training Woman Penetrates Husband in the Ass Pegging 89

Sissy Ass Training Woman Penetrates Husband in the Ass Pegging 89

XHamster 8 months ago

Sophia Loreen Private Show

4K 2:00 / 16:46

Sophia Loreen Private Show

Flirt4Free 2 weeks ago

Sophia Loreen Party on Sep 4, 2026 - Part 2

66% 4K 2:00 / 54:21

Sophia Loreen Party on Sep 4, 2026 - Part 2

Flirt4Free 3 weeks ago

Turning My Boyfriend Into Girlfriend Femdom Sissy Boy Transformation Crossdressing

Turning My Boyfriend Into Girlfriend Femdom Sissy Boy Transformation Crossdressing

XHamster 6 months ago

Natalie Knight gets a massage from her new boss Scarlett Sage

Natalie Knight gets a massage from her new boss Scarlett Sage

Some.Porn 7 months ago

Str8 Trainer

52% HD 0:10 / 22:55

LoyalFans 9 months ago

Sissy UwU solo masturbation 39 mtf British Anal Masturbation Trans flat chastity cages toys

Sissy UwU solo masturbation 39 mtf British Anal Masturbation Trans flat chastity cages toys

XHamster 1 month ago

BIG BLACK COCK Neighbor Back For More Dirty Head From Pretty Trans Woman

BIG BLACK COCK Neighbor Back For More Dirty Head From Pretty Trans Woman

Transvids.tv 1 year ago

Feminization Fortune

Feminization Fortune

XHamster 2 months ago

Trans Goddess Anal Fucked Deep in Gangbang Bukkake Gokkun

Trans Goddess Anal Fucked Deep in Gangbang Bukkake Gokkun

AnalPornXL 1 year ago

Training My Ass & Nipples

68% HD 0:39 / 16:08

Training My Ass & Nipples

FapHouse 6 months ago

outdoor motel risky slutwalk chastity boots

outdoor motel risky slutwalk chastity boots

XHamster 2 months ago

Assfucked Maid Jasmine

63% 0:39 / 6:41

Assfucked Maid Jasmine

FapHouse 8 months ago

Caged up and Lost the Key

Caged up and Lost the Key

XHamster 3 months ago

Sissys Breast Pumping Session Enlarging My Boobs

Sissys Breast Pumping Session Enlarging My Boobs

FapHouse 8 months ago

Dimitri Caruso Private Show

64% HD 2:00 / 15:58

Dimitri Caruso Private Show

Flirt4Free 3 years ago

Ahegao Femboy Ben Tennyson Pumping Her Bimbo Lips with Vacuum Machine in Sissyfication and Feminization Program

Ahegao Femboy Ben Tennyson Pumping Her Bimbo Lips with Vacuum Machine in Sissyfication and Feminization Program

XHamster 1 month ago

Hot Tranny plays with huge 10-inch BBC and gets her Tight Asshole Filled Up With Cum

Hot Tranny plays with huge 10-inch BBC and gets her Tight Asshole Filled Up With Cum

XHamster 3 years ago

Interracial Tease & Ballbusting For Trans Woman | MahoganyQen

67% HD 0:10 / 14:58

Interracial Tease & Ballbusting For Trans Woman | MahoganyQen

LoyalFans 1 year ago

Tyler Blake Sexy Lingerie Ass Stretching & Solo Fisting

Tyler Blake Sexy Lingerie Ass Stretching & Solo Fisting

FapHouse 3 months ago

Sophia Loreen Party on Jul 25, 2026 - Part 3

59% HD 2:00 / 41:09

Sophia Loreen Party on Jul 25, 2026 - Part 3

Flirt4Free 2 months ago

Sissy GOING KNUCKLE DEEP! Mitt puppet!

Sissy GOING KNUCKLE DEEP! Mitt puppet!

TransTube.tv 2 years ago

Sissy Swimsuit Training Step-bro's Pool Humiliation

65% HD 0:39 / 10:44

Sissy Swimsuit Training Step-bro's Pool Humiliation

FapHouse 1 month ago

Diversity Itsol HFO training mindfuck

Diversity Itsol HFO training mindfuck

MyTransfix 4 months ago

Rubdown your weapons with a jizm coated sole approach

Rubdown your weapons with a jizm coated sole approach

Gayhub 1 year ago

Charlie Cano Private Show

67% HD 2:00 / 6:23

Charlie Cano Private Show

Flirt4Free 3 years ago

T-Girl tugging and screaming

T-Girl tugging and screaming

TrannyGem 3 years ago

Sophia Loreen Private Show

66% 4K 2:00 / 11:45

Sophia Loreen Private Show

Flirt4Free 1 month ago

Sissy latexdoll pissing and anal training

Sissy latexdoll pissing and anal training

XHamster 4 years ago

Sissy slave Oksana shows piss, cucumber and orange show in video chat with her Master

Sissy slave Oksana shows piss, cucumber and orange show in video chat with her Master

XHamster 3 years ago

Anal make me Squirt in chastity

Anal make me Squirt in chastity

XHamster 8 months ago

Best firm round ass BOUNCING IN YOUR COCK! Enjoy the wildest ride while I feel you so deep! Lets cum?? (squirt) (puppyeyes) - Part 2

Best firm round ass BOUNCING IN YOUR COCK! Enjoy the wildest ride while I feel you so deep! Lets cum?? (squirt) (puppyeyes) - Part 2

Camster 2 months ago

Mistress Jessica Bloom Teaches You How To Cum From Anal - 6 Sissygasms in a Row

Mistress Jessica Bloom Teaches You How To Cum From Anal - 6 Sissygasms in a Row

XHamster 3 months ago

Alexander & Patric & Alfonso Private Show

55% HD 2:00 / 56:57

Alexander & Patric & Alfonso Private Show

Flirt4Free 4 years ago

What's my name part 2

What's my name part 2

XHamster 2 years ago

Masked Crossdresser slut gets fucked till orgasm from sexmachine

Masked Crossdresser slut gets fucked till orgasm from sexmachine

XHamster 1 year ago

Femboy inserts dildo into gaping ass and cumshot from riding

Femboy inserts dildo into gaping ass and cumshot from riding

XHamster 1 year ago

Girl Love Fuck Crossdresser

Girl Love Fuck Crossdresser

XHamster 1 month ago

Nonbinary Jaq Quicksilver Masturbating with Hitachi Real Orgasm

HD 0:39 / 10:20

Nonbinary Jaq Quicksilver Masturbating with Hitachi Real Orgasm

FapHouse 5 days ago

Sniff Tgirl ass till you cum on command & eat your load!

66% 0:23 / 4:19

Sniff Tgirl ass till you cum on command & eat your load!

Clips4sale 8 months ago

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