Training Videos - Trans (89,932)

My cock-squeezing sissy caboose gets opened up by a beer bottle

My cock-squeezing sissy caboose gets opened up by a beer bottle

TrannyGem 3 years ago

Sissy Shoe Shopping - Feminization - Graceful Control Audios

Sissy Shoe Shopping - Feminization - Graceful Control Audios

Clips4sale 3 months ago

Skinny Sissy Ass Destroyed By 12in Dildo In Stripper Heels Gushing Cum

Skinny Sissy Ass Destroyed By 12in Dildo In Stripper Heels Gushing Cum

JuicyTrans 3 weeks ago

New Sissy Maid Inspection And Training Stage 1 (WMV)

New Sissy Maid Inspection And Training Stage 1 (WMV)

Clips4sale 1 year ago

Melaniie Moon Private Show

Melaniie Moon Private Show

Flirt4Free 1 week ago

Sissygasm Seduction: Jessica Bloom's Top Solo and Shemale Compilation

Sissygasm Seduction: Jessica Bloom's Top Solo and Shemale Compilation

XXXShake 4 years ago

Sissy fapped with an “anal buttplug in my ass” while dressed in a college uniform costume play.

Sissy fapped with an “anal buttplug in my ass” while dressed in a college uniform costume play.

TrannyGem 1 year ago

Sissy play time Part 1 – Sissy Caught Panty Sniffing and Spanked copy

51% 0:30 / 19:59

Sissy play time Part 1 – Sissy Caught Panty Sniffing and Spanked copy

Clips4sale 8 months ago

Daily Cum and PPs DOSE - Gay BDSM Slave Training

Daily Cum and PPs DOSE - Gay BDSM Slave Training

xHamster 1 year ago

Hard sissy training: From hunk to bimbo

Hard sissy training: From hunk to bimbo

ShemaleSin 3 weeks ago

JOI For The Feminized Sissies Clit: POV, Chastity, Crossdressing, Edging, CEI And Cum Count Down

HD 0:59 / 14:35

JOI For The Feminized Sissies Clit: POV, Chastity, Crossdressing, Edging, CEI And Cum Count Down

Clips4sale 1 year ago

Natalia Syn Private Show

Natalia Syn Private Show

Flirt4Free 3 years ago

Ria Bentley Give Small Penis Humiliation To Cuckold Husbands

58% HD 0:23 / 11:12

Ria Bentley Give Small Penis Humiliation To Cuckold Husbands

Clips4sale 2 years ago

Can My Diapers Be a Halloween Costume

HD 0:29 / 12:04

Can My Diapers Be a Halloween Costume

Clips4sale 6 months ago

Loser slave loses bet against 7 Dommes and is gangbanged (1080 EN-sub)

44% HD 0:31 / 23:10

Loser slave loses bet against 7 Dommes and is gangbanged (1080 EN-sub)

Clips4sale 1 year ago

Orientation for Step-Daddy’s New Prisoner

51% HD 0:30 / 13:55

Orientation for Step-Daddy’s New Prisoner

Clips4sale 8 months ago

Valery Brett Private Show

Valery Brett Private Show

Flirt4Free 2 years ago

FULL MOVIE BNWO Bundle Compilation

67% 4K 0:27 / 1:00:48

FULL MOVIE BNWO Bundle Compilation

Clips4sale 1 year ago

Suck It For Futa Step-Mommy

Suck It For Futa Step-Mommy

Clips4sale 1 year ago

”Ebony Mamba Fucks Nick Ryder”

”Ebony Mamba Fucks Nick Ryder”

ThePornstar 7 months ago

BNWO Snowbunny Diaper Costume for the Party

4K 0:30 / 14:32

BNWO Snowbunny Diaper Costume for the Party

Clips4sale 6 months ago

melinda and the fist dildo

melinda and the fist dildo

xHamster 6 years ago

Nvh-021 Strengthening Anal Development Training Camp In A Competitive Swimsuit! Transsexual Reverse Anal Sex! Chibitori

Nvh-021 Strengthening Anal Development Training Camp In A Competitive Swimsuit! Transsexual Reverse Anal Sex! Chibitori

getTranny 1 year ago

Sophia Loreen Party on Feb 25, 2026 - Part 3

4K 2:00 / 34:17

Sophia Loreen Party on Feb 25, 2026 - Part 3

Flirt4Free 2 months ago

from cheater to sissy: punishment pegging from futa mommy - full video on Veggiebabyy Manyvids

from cheater to sissy: punishment pegging from futa mommy - full video on Veggiebabyy Manyvids

xHamster 3 years ago

Valery Brett Private Show

Valery Brett Private Show

Flirt4Free 2 years ago

Crhistian & Dereckk & Friends Party on Nov 24, 2018 - Part 2

HD 2:00 / 38:50

Crhistian & Dereckk & Friends Party on Nov 24, 2018 - Part 2

Flirt4Free 7 years ago

Indian Gay Crossdresser in Rainbow Saree Making Pride for Lgbt XXX

Indian Gay Crossdresser in Rainbow Saree Making Pride for Lgbt XXX

xHamster 7 months ago

Trans Angel Stretched by Screwing Machine

Trans Angel Stretched by Screwing Machine

ShemaleSin 2 years ago

”Sissy Whore Spanking Discipline #FemdomRAW”

”Sissy Whore Spanking Discipline #FemdomRAW”

Trashreality 1 year ago

Committed to Pleasing Him

Committed to Pleasing Him

FapHouse 8 months ago

ENCOURAGED BI FETISH Sissy Pantyhose Crossdressing Humiliation Trailer Compilation PREVIEWS

ENCOURAGED BI FETISH Sissy Pantyhose Crossdressing Humiliation Trailer Compilation PREVIEWS

Juicexxx 5 months ago

High Heels Love Tongue Worship (1080p)

60% HD 0:30 / 7:06

High Heels Love Tongue Worship (1080p)

Clips4sale 11 months ago

Crossdresser Get Manacled - 25 Sec JISM - First-Ever Time Self Restrain Bondage

Crossdresser Get Manacled - 25 Sec JISM - First-Ever Time Self Restrain Bondage

TrannyGem 3 years ago

I love vegetables: aubergines and peppers🤤

I love vegetables: aubergines and peppers🤤

xHamster 2 years ago

Mommy's Pretty Dildo Sissy JOI

65% 0:15 / 14:13

Mommy's Pretty Dildo Sissy JOI

Clips4sale 3 years ago

Sissy Cum Eater

40% 0:21 / 10:52

Sissy Cum Eater

Clips4sale 3 years ago

Creams & Bursts During Endurance Instructing

Creams & Bursts During Endurance Instructing

TrannyGem 2 years ago

I’m Feeling Fertile

HD 0:30 / 11:02

I’m Feeling Fertile

Clips4sale 6 months ago

Tifany Rodriguez & Joel Pineda Private Show

63% HD 2:00 / 6:35

Tifany Rodriguez & Joel Pineda Private Show

Flirt4Free 2 years ago

Andrea & Taty Private Show

HD 2:00 / 14:34

Andrea & Taty Private Show

Flirt4Free 1 month ago

Public abasement dressed in only undies, box key is gone

Public abasement dressed in only undies, box key is gone

TrannyGem 1 year ago

Sissygasm Floozy Caged Training Huge Cumshots & Anal Milking Jessica Bloom

Sissygasm Floozy Caged Training Huge Cumshots & Anal Milking Jessica Bloom

ShemaleSin 4 years ago

Rosy Fuck Stick Blow Instructing

Rosy Fuck Stick Blow Instructing

TrannyGem 2 years ago

Caning training with Syren - Sadistic Lucy - MP4 SD

Caning training with Syren - Sadistic Lucy - MP4 SD

Clips4sale 3 years ago

Petite trans sub gets her asshole fucked by mistress strap-on

Petite trans sub gets her asshole fucked by mistress strap-on

XGroovy 11 months ago

HOT SHOTS ORGASM COMPILATION

HOT SHOTS ORGASM COMPILATION

XVideos 1 year ago

Trans Princess Permits BIG BLACK COCK Kick To Indulge, Entice, and Absorb Her (Total Movie on OnlyFans @DvijaRama)

Trans Princess Permits BIG BLACK COCK Kick To Indulge, Entice, and Absorb Her (Total Movie on OnlyFans @DvijaRama)

TrannyGem 1 year ago

Andrea Lavigne Private Show

HD 2:00 / 12:11

Andrea Lavigne Private Show

Flirt4Free 1 year ago

SatansHoe - Taking it deep and quick getting instructed to be a puppet

SatansHoe - Taking it deep and quick getting instructed to be a puppet

TrannyGem 1 year ago

Sestina Shay August Compilation - Anal, Riding, Big Dildos, Masturbation, Gushing Orgasm

Sestina Shay August Compilation - Anal, Riding, Big Dildos, Masturbation, Gushing Orgasm

Pornzona 1 month ago

My ass anal training

My ass anal training

xHamster 5 years ago

Chinese sissy Femboy GOKKUN messy milk Mushy core swim suits

Chinese sissy Femboy GOKKUN messy milk Mushy core swim suits

TrannyGem 5 months ago

Mexican teen trains her ass with a plug for your cock

Mexican teen trains her ass with a plug for your cock

XXXShemalePorn 2 years ago

Sissy Humiliation Cum Countdown with TS Ria Bentley

66% 4K 0:26 / 8:47

Sissy Humiliation Cum Countdown with TS Ria Bentley

Clips4sale 2 years ago

You Are Nothing, DVD For Download

55% 0:55 / 47:24

You Are Nothing, DVD For Download

Clips4sale 4 years ago

Monster Dong in Devil’s Throat

Monster Dong in Devil’s Throat

ShemaleSin 2 years ago

empty headed sissy destroys her muddy crevice with large BIG BLACK COCK

empty headed sissy destroys her muddy crevice with large BIG BLACK COCK

TrannyGem 3 years ago

He spinned up my cock-squeezing butt and came inwards! Internal Ejaculation! - OF/EMMAINK13

He spinned up my cock-squeezing butt and came inwards! Internal Ejaculation! - OF/EMMAINK13

TrannyGem 11 months ago

Indian Gay Crossdresser Bottom Gaurisissy Showing Her Big Boobs in Purple Saree

Indian Gay Crossdresser Bottom Gaurisissy Showing Her Big Boobs in Purple Saree

xHamster 1 month ago

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 5

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 5

xHamster 1 year ago

I know you are QUEER

I know you are QUEER

TrannyGem 1 year ago

I Can Be Very Verbal and Explicit Sometimes

49% HD 2:00 / 11:03

I Can Be Very Verbal and Explicit Sometimes

Flirt4Free 1 year ago

”Blond kneeling & sucking big dick”

”Blond kneeling & sucking big dick”

TransHero 4 months ago

Femdom POV: Sissification Instructions

Femdom POV: Sissification Instructions

FapHouse 10 months ago

Mom Dominatrix-bitch Wakes Her Sissy Step-Son (Preview)

Mom Dominatrix-bitch Wakes Her Sissy Step-Son (Preview)

ShemaleSin 1 year ago

My homie toyed with me with a bang-out plaything

My homie toyed with me with a bang-out plaything

TrannyGem 5 months ago

Blond Sissy Waits for Gang Hook-Up for Rock-Hard Backside Banging and Dual Rectal Sissy Purity Instructing

Blond Sissy Waits for Gang Hook-Up for Rock-Hard Backside Banging and Dual Rectal Sissy Purity Instructing

TrannyGem 4 years ago

My futa dick is bigger than yours !- SPH

63% HD 0:13 / 10:48

My futa dick is bigger than yours !- SPH

Clips4sale 4 years ago

Dumb Bitch for BBC: FUTA CUSTOM 7 | MahoganyQen

51% 0:26 / 9:12

Dumb Bitch for BBC: FUTA CUSTOM 7 | MahoganyQen

Clips4sale 2 years ago

Total degradation for CD Marty - fucked roughly by dildo and piss in mouth by tranny

Total degradation for CD Marty - fucked roughly by dildo and piss in mouth by tranny

xHamster 9 months ago

Kittykaz Big Dildo Training With Lube

Kittykaz Big Dildo Training With Lube

Nuvid 3 months ago

Preparing for forXed bi first experience high heels school 480p

Preparing for forXed bi first experience high heels school 480p

Clips4sale 4 years ago

Sissified blowjob training MP4

HD 0:25 / 13:15

Sissified blowjob training MP4

Clips4sale 1 month ago

reward pegging for latex futa step-mommy's trained chastity sub - HD wmv

HD 0:30 / 20:05

reward pegging for latex futa step-mommy's trained chastity sub - HD wmv

Clips4sale 8 months ago

Baroness Bijou - Slut Training

HD 1:00 / 56:38

Baroness Bijou - Slut Training

FemDorado 4 years ago

Mesmeriza Compilation 12 Island of Oblivion

Mesmeriza Compilation 12 Island of Oblivion

xHamster 1 year ago

Futa's Pantyhose Sissy Compilation

HD 0:24 / 47:55

Futa's Pantyhose Sissy Compilation

Clips4sale 2 years ago

Dirty British Maid makes a mess with cum...

Dirty British Maid makes a mess with cum...

aShemaleTube 7 years ago

Owned Sissy wench streams & screws herself raw during the time that Hotwife femdom female-dominator is away! 4/5 Full vid in a short time

Owned Sissy wench streams & screws herself raw during the time that Hotwife femdom female-dominator is away! 4/5 Full vid in a short time

ShemaleSin 2 years ago

Zayra Ross Private Show

Zayra Ross Private Show

Flirt4Free 3 weeks ago

Becoming Temptress's Dog

Becoming Temptress's Dog

Clips4sale 1 year ago

Jeans Spanking

Flirt4Free 1 year ago

Bbw pute gros cul twerk Clip 1

Bbw pute gros cul twerk Clip 1

xHamster 4 months ago

Little Silky, Sissy Whore

Little Silky, Sissy Whore

Clips4sale 1 year ago

Cloe & Charlotte Private Show

Cloe & Charlotte Private Show

Flirt4Free 3 years ago

Fit Dominat Sissy Oral Job Training #FemdomRAW - Kendra Heart

Fit Dominat Sissy Oral Job Training #FemdomRAW - Kendra Heart

ShemaleSin 2 years ago

Reverse Psychology - Transform Into the Best Sissy Slut! Step 3: Deepening Through Sexual Humiliation

HD 0:30 / 18:10

Reverse Psychology - Transform Into the Best Sissy Slut! Step 3: Deepening Through Sexual Humiliation

Clips4sale 1 year ago

ASIAN SUBMISSIVE LADYBOY MASTURBATION & CUM

ASIAN SUBMISSIVE LADYBOY MASTURBATION & CUM

Clips4sale 7 months ago

Petra's fifth training

Petra's fifth training

ShemaleSin 1 year ago

SatansHoe - Taking it deep and fast getting trained to be a puppet

SatansHoe - Taking it deep and fast getting trained to be a puppet

TransTube.tv 1 year ago

Chubby Maram Play with Her Dildo so Hot Sexy Trans

Chubby Maram Play with Her Dildo so Hot Sexy Trans

xHamster 7 months ago

Degraded for Wanting to be a Diaper Girl

65% HD 0:30 / 11:25

Degraded for Wanting to be a Diaper Girl

Clips4sale 1 year ago

Exploring the hooker lifestyle: a journey of roleplay

Exploring the hooker lifestyle: a journey of roleplay

XXXShemalePorn 1 year ago

MY PVC MAID

Clips4sale 1 year ago

Today I'm alone in my house so i decided today is sissy day

Today I'm alone in my house so i decided today is sissy day

xHamster 3 years ago

Slavena & Lady Valeska & Lusinta Sissy-MAID services

57% 4K 0:11 / 15:17

Slavena & Lady Valeska & Lusinta Sissy-MAID services

Clips4sale 4 years ago

Lily Eden Drools All Over Her Face in Sloppy Deepthroat Training

Lily Eden Drools All Over Her Face in Sloppy Deepthroat Training

ShemaleSin 5 months ago

NBA All-Star Lola Bunny trains her hole before practice

Premium HD 6:52

NBA All-Star Lola Bunny trains her hole before practice

XVideosRed 2 months ago

Sofia Ferreira Private Show

Sofia Ferreira Private Show

Flirt4Free 8 months ago

Encaged sissy in micro g-string butt ravaged by machine

Encaged sissy in micro g-string butt ravaged by machine

TrannyGem 7 months ago

Jasmine Dlight Three Minute Fuck Frenzy Extreme Anal Gapes and Goon Compilation

Jasmine Dlight Three Minute Fuck Frenzy Extreme Anal Gapes and Goon Compilation

FapHouse 1 year ago

Piss & Anal Training Julia Maze, Azura Alii, Katerina Berg, Diana

Piss & Anal Training Julia Maze, Azura Alii, Katerina Berg, Diana

Xshemale 2 months ago

Pretty Sissy Anal Milking

60% HD 0:11 / 14:10

Pretty Sissy Anal Milking

Clips4sale 4 years ago

Mrs Mature Feet training her sissy Footboy

Mrs Mature Feet training her sissy Footboy

xHamster 2 months ago

TRANNIES XXX: Pleasuring Dayanna Vidal

TRANNIES XXX: Pleasuring Dayanna Vidal

ShemaleSin 3 years ago

”Trans mistress Emma Rose trains mommy”

”Trans mistress Emma Rose trains mommy”

Faptor 2 years ago

Double dom with Lady Valeska: Sissy begs for cum

Double dom with Lady Valeska: Sissy begs for cum

Clips4sale 1 year ago

Justin & Fede & Ron Private Show

Justin & Fede & Ron Private Show

Flirt4Free 3 years ago

SheMale Evolution

55% 4K 0:15 / 4:26

SheMale Evolution

Clips4sale 2 years ago

Sissy BBC addiction BBC submission BBC domination Sissy mindset Sissy possitive affirmation tranny transsexual transsexual trans

Sissy BBC addiction BBC submission BBC domination Sissy mindset Sissy possitive affirmation tranny transsexual transsexual trans

ShemaleSin 3 years ago

Creams & Squirts During Stamina Training

Creams & Squirts During Stamina Training

ShemaleSin 2 years ago

Too Deep to Deny: Pussy Is Powerless Now

Too Deep to Deny: Pussy Is Powerless Now

Clips4sale 3 months ago

Bareback Submission - the Extreme Anal Slut!

HD 0:39 / 30:08

Bareback Submission - the Extreme Anal Slut!

FapHouse 2 years ago

Manila Tuzon Private Show

HD 2:00 / 23:06

Manila Tuzon Private Show

Flirt4Free 2 years ago

SISSY SLUT MENTAL PROGRAMMING - Want to be a total slut? Slut Training Conditioning

SISSY SLUT MENTAL PROGRAMMING - Want to be a total slut? Slut Training Conditioning

Clips4sale 1 year ago

Sissies Belong In Chastity (4KUHD MP4)

HD 0:30 / 15:17

Sissies Belong In Chastity (4KUHD MP4)

Clips4sale 2 years ago

Diapers Instead of Domination

Diapers Instead of Domination

Clips4sale 3 months ago

Luke Hardy & Cristian Ford Private Show

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 year ago

You Will Only Finger Yourself From Now On | Sissygasm JOI

58% 0:30 / 10:33

You Will Only Finger Yourself From Now On | Sissygasm JOI

Clips4sale 1 year ago

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89,932 results found

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