Training Videos - Trans (90,164)

Sexy sissy in pink lingerie loves playing with her toys. cross dressing femboy fucks ass riding dildo

Sexy sissy in pink lingerie loves playing with her toys. cross dressing femboy fucks ass riding dildo

xHamster 5 months ago

Sissy anal table joi

Sissy anal table joi

xHamster 1 year ago

centaur things 3 - (amy s big wish 3-3) - a futanari deertaur gets trained in the art of breeding!

63% 0:29 / 9:40

centaur things 3 - (amy s big wish 3-3) - a futanari deertaur gets trained in the art of breeding!

PornBox 3 weeks ago

Jogging with a Full Bladder! Great Tranny Wetting with a Huge Beam Straight Down!

66% HD 0:39 / 5:59

Jogging with a Full Bladder! Great Tranny Wetting with a Huge Beam Straight Down!

FapHouse 3 months ago

Mouth fucking a deepthroated sissy bitch while watching porn

Mouth fucking a deepthroated sissy bitch while watching porn

xHamster 4 years ago

Giving up All Resistance

70% 1:01 / 24:56

Giving up All Resistance

FapHouse 10 months ago

PetraTVsletje's 8th Training: A Hardcore Fisting, Anal, and a Huge Dildo Ride!

PetraTVsletje's 8th Training: A Hardcore Fisting, Anal, and a Huge Dildo Ride!

TrannyMovs 7 months ago

Ella Hollywood (Training Arc)

Ella Hollywood (Training Arc)

aShemaleTube 7 months ago

Doggy style sissy training in a red dress and white pumps

Doggy style sissy training in a red dress and white pumps

xHamster 2 years ago

Trainer's Order No63 Laundry Exposure 2nd Round

Trainer's Order No63 Laundry Exposure 2nd Round

xHamster 4 months ago

Beautiful Blonde Sissy Maddy Stuffing Her Ass With Big Toys

Beautiful Blonde Sissy Maddy Stuffing Her Ass With Big Toys

xHamster 5 months ago

Asian Beauty in College Uniform Squirts While Training Her Anal by Pushing a Huge Anal Plug Out

67% HD 0:39 / 7:47

Asian Beauty in College Uniform Squirts While Training Her Anal by Pushing a Huge Anal Plug Out

FapHouse 2 months ago

Taking Your Ass fucking Viginity ft Trans Femdominance

Taking Your Ass fucking Viginity ft Trans Femdominance

TransTube.tv 1 year ago

SLAVES TRAINING SCHOOL UK 1991 (part 1)

SLAVES TRAINING SCHOOL UK 1991 (part 1)

Tranny.one 3 years ago

Ms Minxy’s Eternal Bareback Submission

51% 1:01 / 26:28

Ms Minxy’s Eternal Bareback Submission

FapHouse 1 year ago

CUMSHOT FISTING PISSING PRECUM COMPILATION!

CUMSHOT FISTING PISSING PRECUM COMPILATION!

TransJizz 8 months ago

Slut Training Maxine X Double Stuffed in All Holes

54% HD 0:39 / 48:11

Slut Training Maxine X Double Stuffed in All Holes

FapHouse 2 months ago

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

TrannyGem 1 year ago

Sophia Loreen Private Show

59% HD 2:00 / 12:52

Sophia Loreen Private Show

Flirt4Free 9 months ago

Fat Ass Femboy Raven Asshole Gaped, Creampie and Cuming After Intense Anal Sex with BBC Dildo

45% HD 0:39 / 29:01

Fat Ass Femboy Raven Asshole Gaped, Creampie and Cuming After Intense Anal Sex with BBC Dildo

FapHouse 1 month ago

STRAIGHT GUYS LOVE SHEMALES - ENCOURAGED BI

56% HD 0:10 / 25:08

STRAIGHT GUYS LOVE SHEMALES - ENCOURAGED BI

LoyalFans 6 months ago

Sissy Locks Her Tiny Clitty in Inverted Chastity Cage and Rides Her Big Qutoys Dildo

Sissy Locks Her Tiny Clitty in Inverted Chastity Cage and Rides Her Big Qutoys Dildo

xHamster 6 days ago

Reality Porn Theatre

65% 0:39 / 53:42

Reality Porn Theatre

FapHouse 1 month 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

Mistress pegs & sissifies her pathetic small cocked hubby

Mistress pegs & sissifies her pathetic small cocked hubby

xHamster 2 months ago

Sissy femboy bi-atch Pleasing monster gigantic dark-hued lollipop and servicing him fellate and kissing giant dark-hued pipe passionately

Sissy femboy bi-atch Pleasing monster gigantic dark-hued lollipop and servicing him fellate and kissing giant dark-hued pipe passionately

2BGay 2 years ago

Nyxi Leon Fucked in 5 Different Positions by TS Mistress Bailey Love & More!

78% HD 1:01 / 19:53

Nyxi Leon Fucked in 5 Different Positions by TS Mistress Bailey Love & More!

FapHouse 2 years ago

◆ 3D FUTA Beauty’s First Time Turns Into Intense Pleasure as Toys & Big Pecker Bring Her to Orgasm

◆ 3D FUTA Beauty’s First Time Turns Into Intense Pleasure as Toys & Big Pecker Bring Her to Orgasm

Sheshaft 3 months ago

Glam Slut Milking Training 2

62% HD 1:01 / 20:26

Glam Slut Milking Training 2

FapHouse 3 months ago

Femdom Sissy Chastity Tease

54% HD 0:39 / 13:28

Femdom Sissy Chastity Tease

FapHouse 1 month ago

So hot cumming after 7 days in chastity and anal training

So hot cumming after 7 days in chastity and anal training

xHamster 1 year ago

Cute Pretty Femboy

Cute Pretty Femboy

FapHouse 1 week ago

Viky & Emma Private Show

61% HD 2:00 / 5:59

Viky & Emma Private Show

Flirt4Free 3 months ago

Livestream 10.01.24 - Party with Madame Ophelia and TS Djamila

HD 0:10 / 34:13

Livestream 10.01.24 - Party with Madame Ophelia and TS Djamila

LoyalFans 2 years ago

Sissy Bitch Boyfriend

Sissy Bitch Boyfriend

FapHouse 1 year ago

Top 10 Femdom Ideas 2022

Top 10 Femdom Ideas 2022

xHamster 2 years ago

Extreme Huge Man Nipples Titten-Sau Nipple Pain Slut FAG

Extreme Huge Man Nipples Titten-Sau Nipple Pain Slut FAG

xHamster 2 years ago

Training My Ass & Nipples

57% HD 1:01 / 16:08

Training My Ass & Nipples

FapHouse 1 month ago

Hana Rouse Private Show

52% 4K 2:00 / 24:45

Hana Rouse Private Show

Flirt4Free 5 months ago

Ada Valentine fisting and huge toy play

Ada Valentine fisting and huge toy play

xHamster 1 month ago

Protection Sissy

Protection Sissy

TrannyGem 4 years ago

Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl

Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl

xHamster 1 year ago

All that mouth training pays off : facefucking charming transwife Melody

All that mouth training pays off : facefucking charming transwife Melody

Amateur8 8 months ago

when your potty trained pet is home alone

when your potty trained pet is home alone

xHamster 8 months ago

Submissive Ladyboy First Slave Training & Anal Casting

63% HD 1:01 / 30:15

Submissive Ladyboy First Slave Training & Anal Casting

FapHouse 1 month ago

Sissygasm for Domina

66% 0:39 / 4:11

Sissygasm for Domina

FapHouse 9 months ago

TS Slut Milking

59% HD 0:10 / 14:32

TS Slut Milking

LoyalFans 7 months ago

Brutus K Models a Red Thong

69% HD 2:00 / 8:55

Brutus K Models a Red Thong

Flirt4Free 1 year ago

Sissy Bride Getting Fucked by Her Doll

Sissy Bride Getting Fucked by Her Doll

xHamster 8 months ago

Husband sissified, bent over and made to spread his ass cheeks for mistress's big cock to pound his tight boi pussy

Husband sissified, bent over and made to spread his ass cheeks for mistress's big cock to pound his tight boi pussy

xHamster 2 years ago

Chastity Slave Washes Himself.

57% HD 0:39 / 5:26

Chastity Slave Washes Himself.

FapHouse 3 months ago

Transgirl in Chastity Humps Her Pillows

Transgirl in Chastity Humps Her Pillows

Tranny.one 1 week ago

Worship Stepdaddy Kyaa's Dick

54% HD 1:01 / 11:04

Worship Stepdaddy Kyaa's Dick

FapHouse 2 months ago

Sex-er-cise

67% HD 1:01 / 56:08

FapHouse 1 year ago

Ivy & Headmistress; Sissification & Humiliation Punishment

59% 1:01 / 26:37

Ivy & Headmistress; Sissification & Humiliation Punishment

FapHouse 1 year ago

He so Wants to Cum, but His Hands and Head Are Shackled!

He so Wants to Cum, but His Hands and Head Are Shackled!

FapHouse 1 year ago

Fun with a mature whore! POV only! Closeup only!

Fun with a mature whore! POV only! Closeup only!

xHamster 4 years ago

Bi Encouragement Let's Watch Shemale Porn

HD 0:39 / 17:37

Bi Encouragement Let's Watch Shemale Porn

FapHouse 1 week ago

Transformation from a regular boy into a insatiable sissy romp fuckslut that can be used firm sans grace.

Transformation from a regular boy into a insatiable sissy romp fuckslut that can be used firm sans grace.

TrannyGem 11 months ago

Self-Training No68 Tucking On A Public Beach

Self-Training No68 Tucking On A Public Beach

xHamster 3 months ago

Day 9 of Sissy Training - Makeup Melts Your Masculinity

58% HD 1:01 / 21:08

Day 9 of Sissy Training - Makeup Melts Your Masculinity

FapHouse 3 months ago

Femdom POV Sissy Training Embrace Your Femininity

61% HD 1:01 / 10:01

Femdom POV Sissy Training Embrace Your Femininity

FapHouse 1 month ago

Breaking Ts Jasmine Lotus: Chasity Slut Punished & Covered in Cum

58% HD 0:10 / 16:19

Breaking Ts Jasmine Lotus: Chasity Slut Punished & Covered in Cum

LoyalFans 6 months ago

The bondage and feminization of a slave by a blonde queen

The bondage and feminization of a slave by a blonde queen

xHamster 1 year ago

Sissy's Feminization

Sissy's Feminization

ShemaleSin 1 month ago

Ep. 964 Sexy Outfit for Sissy - Get Dressed by Mistress in Wolford Neon 40 Gobi Pantyhose - Strap-on Training, Feminization

50% HD 0:39 / 10:13

Ep. 964 Sexy Outfit for Sissy - Get Dressed by Mistress in Wolford Neon 40 Gobi Pantyhose - Strap-on Training, Feminization

FapHouse 1 year ago

Tantaly : An Unexpected Christmas Gift: A Sissy's Penetration - Mistress Julia

Tantaly : An Unexpected Christmas Gift: A Sissy's Penetration - Mistress Julia

xHamster 1 year ago

Fettered to Fuck stick for Sissy Deep-throat Instructing

Fettered to Fuck stick for Sissy Deep-throat Instructing

Gayhub 6 months ago

Sissy In Blue Riding Her Dildos

Sissy In Blue Riding Her Dildos

xHamster 3 months ago

My Butt Is Made for Anal and Creampies

63% HD 0:39 / 22:24

My Butt Is Made for Anal and Creampies

FapHouse 1 year ago

Frisky night into the parking lot

Frisky night into the parking lot

xHamster 1 year ago

Doggy Training... Will He Obey?

64% HD 1:01 / 15:52

Doggy Training... Will He Obey?

FapHouse 1 year ago

busty redhead sissy walks around in leather platform thigh high boots and red miniskirt

busty redhead sissy walks around in leather platform thigh high boots and red miniskirt

xHamster 3 years ago

Sissy Joyce’s Very First Training Session with Her Two Mistress

66% 0:39 / 10:07

Sissy Joyce’s Very First Training Session with Her Two Mistress

FapHouse 3 weeks ago

Cute Small Dick Trans Raven Pissing After Intense Anal Riding and Massive Creampie Cumfarts

Cute Small Dick Trans Raven Pissing After Intense Anal Riding and Massive Creampie Cumfarts

xHamster 1 week ago

Corporate Futa Training

Corporate Futa Training

Tranny.one 3 years ago

How to break a Sissy

How to break a Sissy

ShemaleSin 1 week ago

Rot Couch

FapHouse 5 days ago

Sissy Trainer - Feminization - Sissy Instructing - Sissifcation - BIG BLACK COCK

Sissy Trainer - Feminization - Sissy Instructing - Sissifcation - BIG BLACK COCK

TrannyGem 3 years ago

head and eyebrows shave for obedient slave

head and eyebrows shave for obedient slave

xHamster 2 years ago

Hardcore deepthroating facefuck a blindfold sissy slave

Hardcore deepthroating facefuck a blindfold sissy slave

xHamster 4 years ago

Ts Isabella loves sissy training for English Mistresses

Ts Isabella loves sissy training for English Mistresses

xHamster 3 years ago

Sissy coming home from work

Sissy coming home from work

xHamster 10 months ago

Surviving 24 Hours As The Beach Fuck-A-Thon Sub

Surviving 24 Hours As The Beach Fuck-A-Thon Sub

TrannyGem 2 years ago

Master Trainer's Personal Training No. 30: Outdoor Restraint Vibrator Training

60% HD 1:01 / 12:11

Master Trainer's Personal Training No. 30: Outdoor Restraint Vibrator Training

FapHouse 4 months ago

Hot White Dress

Hot White Dress

Flirt4Free 4 weeks ago

Sissy Training Part 4

Sissy Training Part 4

aShemaleTube 4 months ago

The Hot Rabbit 🐰

The Hot Rabbit 🐰

WebcamBros 6 months ago

DO YOU WISH YOUR GIRLFRIEND HAD A PEGGING FETISH?

DO YOU WISH YOUR GIRLFRIEND HAD A PEGGING FETISH?

xHamster 10 months ago

”REALTGIRLS: Cream Pie from the Space Guy”

”REALTGIRLS: Cream Pie from the Space Guy”

429Men 3 months ago

Feminization and Pegging of My Chastity Slave: Teaser Live Cam Replay: Mistress Julia

Feminization and Pegging of My Chastity Slave: Teaser Live Cam Replay: Mistress Julia

xHamster 1 year ago

Submissive Ladyboy Slave Training & Anal Fisting

63% HD 1:01 / 1:04:30

Submissive Ladyboy Slave Training & Anal Fisting

FapHouse 1 week ago

Jerk off While I cum on Your Face Sissy Faggot - Jessica Bloom Humilation JoI

Jerk off While I cum on Your Face Sissy Faggot - Jessica Bloom Humilation JoI

xHamster 2 years ago

Male Bitch Shared Amongst TS Friends

53% HD 0:39 / 41:21

Male Bitch Shared Amongst TS Friends

FapHouse 4 months ago

Hole training

aShemaleTube 3 years ago

Step Mom Sissification JOI CEI for Panty

57% HD 0:39 / 15:45

Step Mom Sissification JOI CEI for Panty

FapHouse 1 year ago

Rubdown your weapons with a jizm coated sole approach

Rubdown your weapons with a jizm coated sole approach

Gayhub 8 months ago

Mistress Lilith Destroys My Ass

65% HD 0:39 / 19:05

Mistress Lilith Destroys My Ass

FapHouse 1 month ago

Sissy Slut Training Part 6

Sissy Slut Training Part 6

xHamster 1 year ago

Colombian Boys Private Show

62% HD 2:00 / 23:35

Colombian Boys Private Show

Flirt4Free 2 years ago

Sissy Silly Step-Sister Raunchy Drill and Gargle

Sissy Silly Step-Sister Raunchy Drill and Gargle

TrannyGem 5 years ago

Sophia Loreen Party on Apr 21, 2026 - Part 3

HD 2:00 / 40:40

Sophia Loreen Party on Apr 21, 2026 - Part 3

Flirt4Free 1 week ago

A Shemale Took My Hand and Placed It Over Her Panty - 2

HD 1:01 / 12:19

A Shemale Took My Hand and Placed It Over Her Panty - 2

FapHouse 7 months ago

Long Lasting Anal Machine Fuck for Crossdressers with Big Fake Tits

HD 1:01 / 11:23

Long Lasting Anal Machine Fuck for Crossdressers with Big Fake Tits

FapHouse 2 years ago

Petite Trans Kawaii Fiona Fucks a Submissive Trans Girl

48% 1:01 / 37:48

Petite Trans Kawaii Fiona Fucks a Submissive Trans Girl

FapHouse 1 year ago

Jakeygirl1987's first time with a hot babe in high heels & lingerie

Jakeygirl1987's first time with a hot babe in high heels & lingerie

TrannyMovs 6 months ago

Suck Jessica Bloom's Trans Cock - Large Buttplug Training + Swallow My Load Then Your Own CEI

Suck Jessica Bloom's Trans Cock - Large Buttplug Training + Swallow My Load Then Your Own CEI

Dafreeporn 2 weeks ago

Mistress Makes Crossdresser Masochist Suck Her Strap-on Dick and Inserts Her Finger Into His Anus and Stirring It Around

HD 1:01 / 22:20

Mistress Makes Crossdresser Masochist Suck Her Strap-on Dick and Inserts Her Finger Into His Anus and Stirring It Around

FapHouse 1 month ago

The Year of Gender Transformation - 2024

57% HD 1:01 / 9:24

The Year of Gender Transformation - 2024

FapHouse 1 year ago

Turning into a human sex toy for my mistress's pleasure

Turning into a human sex toy for my mistress's pleasure

xHamster 10 months ago

Extreme Maschine Fuck and fisting for Crossdresser with heels + nipple pumps Clip

Extreme Maschine Fuck and fisting for Crossdresser with heels + nipple pumps Clip

xHamster 1 year ago

Does my hand fit in his little ass?

Does my hand fit in his little ass?

xHamster 1 year ago

Sissy Bunny Training

65% HD 1:01 / 13:05

Sissy Bunny Training

FapHouse 1 year ago

Pissing on my cute femboy GF Hayley

Pissing on my cute femboy GF Hayley

xHamster 7 months ago

Sissy Femboy Bondage Feminization Training

61% HD 0:39 / 14:58

Sissy Femboy Bondage Feminization Training

FapHouse 1 year ago

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

66% HD 1:01 / 12:50

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

FapHouse 7 months ago

Becoming a Woman - Sissyfication - Ultimate Sissy Transformation

Becoming a Woman - Sissyfication - Ultimate Sissy Transformation

xHamster 2 months ago

My busty tgirl nurse packs a big cock ready to anal fuck me

My busty tgirl nurse packs a big cock ready to anal fuck me

Wankoz 23 hours ago

Lizzy Woo’s Ass Wrecked First-time Strap-on Pegging by Your Cruel Stepmommy Domme Watch Her Beg for More

Lizzy Woo’s Ass Wrecked First-time Strap-on Pegging by Your Cruel Stepmommy Domme Watch Her Beg for More

FapHouse 4 days ago

Heads "in" front ends?

Heads "in" front ends?

xHamster 3 months ago

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