Training Videos - Trans (82,514)

Sophia Loreen Party on Dec 9, 2025 - Part 2

4K 2:00 / 50:10

Sophia Loreen Party on Dec 9, 2025 - Part 2

Flirt4Free 1 week ago

Locktober Sessions - a Vibrator for That Little Clitty

65% HD 0:39 / 9:54

Locktober Sessions - a Vibrator for That Little Clitty

FapHouse 2 months ago

White Glove Enjoyment

White Glove Enjoyment

Lesbian8 1 month ago

Sissy shemale cosplay, enjoys sucking cocks, playing with vibrator and licking pussies while in chastity and self bondage

Sissy shemale cosplay, enjoys sucking cocks, playing with vibrator and licking pussies while in chastity and self bondage

xHamster 2 months ago

Sarada Training v2.2 Part 14 New Power By LoveSkySan69

Sarada Training v2.2 Part 14 New Power By LoveSkySan69

Pornzona 2 weeks ago

Sissy Tart In Crimson Underwear Rail The Fuck Stick

Sissy Tart In Crimson Underwear Rail The Fuck Stick

TrannyGem 1 month ago

BBC goes deep in sexy transsexual babe Kasey Kei in doggy pose

BBC goes deep in sexy transsexual babe Kasey Kei in doggy pose

XGroovy 2 years ago

Ella Mistress Private Show

HD 2:00 / 13:34

Ella Mistress Private Show

Flirt4Free 2 years ago

Sissy Ruins Ballsack and Finishes Off!

Sissy Ruins Ballsack and Finishes Off!

TrannyGem 4 months ago

Emotional moment from "Compile VANesSaBITCHxx photos SEXxLive 2023"

Emotional moment from "Compile VANesSaBITCHxx photos SEXxLive 2023"

xHamster 2 months ago

Sex Machine and Deepthroat

Sex Machine and Deepthroat

xHamster 2 years ago

”REALTGIRLS: Cream Pie from the Space Guy”

”REALTGIRLS: Cream Pie from the Space Guy”

TransHero 1 year ago

Sissy husband dressed up & pegged

Sissy husband dressed up & pegged

xHamster 2 years ago

femboy in innocence cell w restrain bondage getup getting plowed on couch

femboy in innocence cell w restrain bondage getup getting plowed on couch

TrannyGem 2 years ago

hard anal destruction and deepthroat training for stupid maso sexslave

hard anal destruction and deepthroat training for stupid maso sexslave

AnalVids 1 month ago

Sissy Training Cam Session - All Holes

Sissy Training Cam Session - All Holes

FapHouse 5 months ago

Sissy finishes Domina Gie's assignment to have a sesh in a public place

Sissy finishes Domina Gie's assignment to have a sesh in a public place

TrannyGem 3 years ago

Sissy tramp ass fucking BIG BLACK COCK Gape goddess

Sissy tramp ass fucking BIG BLACK COCK Gape goddess

TrannyGem 3 years ago

Femboy Cumshot Sissygasm from Ball-Plapping for the BNWO

Femboy Cumshot Sissygasm from Ball-Plapping for the BNWO

xHamster 3 months ago

CUM PEGGING and FISTING HEADMISTRESS COMPILATION

CUM PEGGING and FISTING HEADMISTRESS COMPILATION

ShemaleSin 6 months ago

Freya Bliss Private Show

HD 2:00 / 11:35

Freya Bliss Private Show

Flirt4Free 2 weeks ago

domina feeding sissy humungous trunk

domina feeding sissy humungous trunk

TrannyGem 3 years ago

This Video Is the 1st in a Series of Nyxi Leon's Very First Transformation Ever

66% HD 1:01 / 25:41

This Video Is the 1st in a Series of Nyxi Leon's Very First Transformation Ever

FapHouse 1 year ago

Femboy Plays with Fat Dildo

Femboy Plays with Fat Dildo

xHamster 1 year ago

Christian & Oliver & Matt Private Show

45% HD 2:00 / 21:46

Christian & Oliver & Matt Private Show

Flirt4Free 3 years ago

White Sissy plays with her hole while clit is caged in stainless steel

White Sissy plays with her hole while clit is caged in stainless steel

xHamster 3 years ago

Transsexual training - bukkake gokkun! Shemale anal fuck orgy 4

Transsexual training - bukkake gokkun! Shemale anal fuck orgy 4

Lesbian8 10 months ago

Sissy swallows bbc cumload

Sissy swallows bbc cumload

ShemaleSin 2 years ago

”Petite sub twat slapped by lesbian dom”

”Petite sub twat slapped by lesbian dom”

TransHero 1 day ago

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

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

xHamster 8 months ago

Wish it was your dick instead of a fuck machine in my anal

Wish it was your dick instead of a fuck machine in my anal

XGroovy 2 years ago

sissy gal ass fucking trainer with penetrate machine big black cock fake-manstick

sissy gal ass fucking trainer with penetrate machine big black cock fake-manstick

TransTube.tv 1 year ago

”Goddess Kyaa & River Enza in Gape Training 1”

”Goddess Kyaa & River Enza in Gape Training 1”

LesbianBliss 1 week ago

redhead tranny sissy slut training her ass off

redhead tranny sissy slut training her ass off

PornBox 2 years ago

Bonny Shiine Private Show

HD 2:00 / 16:56

Bonny Shiine Private Show

Flirt4Free 1 year ago

Faggot by Sissy Sandra

Faggot by Sissy Sandra

TrannyGem 7 years ago

Sissy Boi Teaching

Sissy Boi Teaching

TrannyGem 4 years ago

”18 Year Old Brooklyn Gets Her Throat Trained”

”18 Year Old Brooklyn Gets Her Throat Trained”

TransHero 6 days ago

Azalea Julianna Private Show

Azalea Julianna Private Show

Flirt4Free 2 weeks ago

Cosplay slut Jenby Doll gets trained by Skye January (with cumshot and overstim)

Premium HD 8:31

Cosplay slut Jenby Doll gets trained by Skye January (with cumshot and overstim)

xnxxGold 3 years ago

Swallow My Spit and Cum Loser! - Femdom Jessica Bloom

HD 0:39 / 18:59

Swallow My Spit and Cum Loser! - Femdom Jessica Bloom

FapHouse 1 year ago

Simon & Juseph & Alejandro Private Show

48% HD 2:00 / 1:02:40

Simon & Juseph & Alejandro Private Show

Flirt4Free 2 years ago

Uncovered CD Sissy Katie Does Live Showcase In Purity Cell

Uncovered CD Sissy Katie Does Live Showcase In Purity Cell

TrannyGem 7 months ago

Retro Sissy Teaching (Recolored)

Retro Sissy Teaching (Recolored)

TransTube.tv 4 months ago

Sissy faggot bitch

Sissy faggot bitch

xHamster 1 year ago

Part 2: a Transformed Life: Episode 1 - Meeting Julia, the Life Coach - Maitresse Julia

44% HD 1:01 / 11:40

Part 2: a Transformed Life: Episode 1 - Meeting Julia, the Life Coach - Maitresse Julia

FapHouse 1 year ago

Sissy pluged riding BBC Dildo at desk

Sissy pluged riding BBC Dildo at desk

xHamster 2 months ago

Teen sissy slut secludes herself in nature and fucks her bimbo ass with a huge dilduck

Teen sissy slut secludes herself in nature and fucks her bimbo ass with a huge dilduck

xHamster 11 months ago

Spreading my self before BIG BLACK COCK ten inch Dad comes over again... Total Flick on OF W BIG BLACK COCK Father Romping

Spreading my self before BIG BLACK COCK ten inch Dad comes over again... Total Flick on OF W BIG BLACK COCK Father Romping

TrannyGem 2 weeks ago

FEMINIZATION. SISSIFICATION. THE BLONDE CROSSDRESSER GAVE HIS BODY TO THE MISTRESS.

Premium HD 8:56

FEMINIZATION. SISSIFICATION. THE BLONDE CROSSDRESSER GAVE HIS BODY TO THE MISTRESS.

Sheer 2 years ago

Blessed sissy dazed by numerous sissygasms railing phat 12.5”/32cm Fat Father fuck stick

Blessed sissy dazed by numerous sissygasms railing phat 12.5”/32cm Fat Father fuck stick

TrannyGem 10 months ago

Wife dresses up and fucks her husband in his ass

Wife dresses up and fucks her husband in his ass

xHamster 3 months ago

Riding a 2 Foot Long Dildo on a Pole, How Far Can I Get Down on It? Extreme Anal

Riding a 2 Foot Long Dildo on a Pole, How Far Can I Get Down on It? Extreme Anal

FapHouse 1 year ago

Extreme Fetish Wedges 01

Extreme Fetish Wedges 01

FapHouse 2 years ago

Cum in my mouth, play with your cum, and swallow it, sexy, femboy, trans, gay naughty, tongue, sloopy, six pack, fitness teen

Cum in my mouth, play with your cum, and swallow it, sexy, femboy, trans, gay naughty, tongue, sloopy, six pack, fitness teen

xHamster 9 months ago

Femboy Rectal Spreading With A Yam-Sized Node Fuck Stick

Femboy Rectal Spreading With A Yam-Sized Node Fuck Stick

Gay4Porn 10 months ago

Sandy Nell Private Show

Sandy Nell Private Show

Flirt4Free 2 years ago

hot cumshot compilation of wet orgasms bitch femboy sissygasm slut ass

hot cumshot compilation of wet orgasms bitch femboy sissygasm slut ass

FapCat 3 years ago

Anal inflatable giant dildo

Anal inflatable giant dildo

xHamster 1 year ago

chest play and nipple clamps

chest play and nipple clamps

Flirt4Free 13 years ago

Ring Gagged and Sucking

Ring Gagged and Sucking

xHamster 4 years ago

Pink Satin Sissy Maid Rides Her Sex Doll Toy While Locked

Pink Satin Sissy Maid Rides Her Sex Doll Toy While Locked

xHamster 2 weeks ago

Get Your Mouth Ready for the BBC

Get Your Mouth Ready for the BBC

FapHouse 2 years ago

Desire Sweet Private Show

HD 2:00 / 10:38

Desire Sweet Private Show

Flirt4Free 1 week ago

Elias & Elix Private Show

61% HD 2:00 / 41:34

Elias & Elix Private Show

Flirt4Free 1 month ago

Сука фембой Hattabi4ik писает себе на лицо и в рот сквирт с анальной пробкой в заднице

Сука фембой Hattabi4ik писает себе на лицо и в рот сквирт с анальной пробкой в заднице

XVideos 8 months ago

Assplay with Ohmibod

Assplay with Ohmibod

Flirt4Free 5 years ago

Cyberpunk Crossdresser toys her cunt and eats cum

Cyberpunk Crossdresser toys her cunt and eats cum

BigTitsLust 1 month ago

Dad paid me a lil visit

Dad paid me a lil visit

TrannyGem 1 month ago

Goddess Lohan - Gluttonous Slut Gets Picked Up the Ass

Goddess Lohan - Gluttonous Slut Gets Picked Up the Ass

Clips4sale 2 years ago

Lush sissy at the beach

Lush sissy at the beach

Gayhub 8 months ago

training for christmas

training for christmas

xHamster 5 years ago

Redhead Sissy First Using a Sex-machine This Is a Sweet Gift From a Fan

Redhead Sissy First Using a Sex-machine This Is a Sweet Gift From a Fan

xHamster 2 weeks ago

Bitch boi husband dresses up as a sissy bitch and pegged in his tight boi pussy

Bitch boi husband dresses up as a sissy bitch and pegged in his tight boi pussy

xHamster 2 years ago

Alejandro Montenegro Private Show

4K 2:00 / 26:58

Alejandro Montenegro Private Show

Flirt4Free 1 week ago

sissy femboy bondage feminization training

sissy femboy bondage feminization training

PornBox 11 months ago

The Sissy Cunt Alina Take the Cum Her Owner Like Good Girl

60% HD 0:39 / 1:51

The Sissy Cunt Alina Take the Cum Her Owner Like Good Girl

FapHouse 5 months ago

[FayGrey] Raven trains you to be a cumslut (Femdom cei joi assplay Futa trainer)

[FayGrey] Raven trains you to be a cumslut (Femdom cei joi assplay Futa trainer)

Pornzona 1 month ago

Sophia Loreen Party on Nov 29, 2025 - Part 2

4K 2:00 / 1:05:36

Sophia Loreen Party on Nov 29, 2025 - Part 2

Flirt4Free 3 weeks ago

”Crossdresser Screwed by My Strap-on Dildo”

”Crossdresser Screwed by My Strap-on Dildo”

429Men 4 days ago

My gape anal pic colections

My gape anal pic colections

xHamster 2 weeks ago

”GENDER X Transgender cheerleader rides on black dick - Smash Thompson,Ella Hollywood”

”GENDER X Transgender cheerleader rides on black dick - Smash Thompson,Ella Hollywood”

ThePornstar 1 year ago

Alejandro Montenegro Private Show

Alejandro Montenegro Private Show

Flirt4Free 1 week ago

Sissy Fisted

5Gays 2 months ago

Me da pena hacer un trio con tu amiga, trio con dos vaquitas me sacan la leche

Me da pena hacer un trio con tu amiga, trio con dos vaquitas me sacan la leche

XVideosRed 2 months ago

Kayla's SISSY Sissyfication INSTRUCTING Directives

Kayla's SISSY Sissyfication INSTRUCTING Directives

TrannyGem 2 years ago

A Fucktoys Duties

A Fucktoys Duties

BallsAndBoobs 10 months ago

Lovely sissy's Anal Invasion Teaching ♡ Rotor wedged into the anal invasion ♡ chinese crossdresser onanism

Lovely sissy's Anal Invasion Teaching ♡ Rotor wedged into the anal invasion ♡ chinese crossdresser onanism

TrannyGem 1 month ago

Tightening To Spunk From Ass-Fuck In Her Vapid Tiny Cell

Tightening To Spunk From Ass-Fuck In Her Vapid Tiny Cell

TrannyGem 1 year ago

Huge 9in Dildo Fucking Compilation Vol.5

Huge 9in Dildo Fucking Compilation Vol.5

aShemaleTube 5 months ago

Pegging my sissified bitch boi

Pegging my sissified bitch boi

xHamster 1 year ago

Nutting while having a seat

Nutting while having a seat

TrannyGem 2 months ago

INSTRUCTING for SISSY: "four STEPS to ACHIEVING SISSYGASM" Veronica Taboo trains SISSIFICATION

INSTRUCTING for SISSY: "four STEPS to ACHIEVING SISSYGASM" Veronica Taboo trains SISSIFICATION

TrannyGem 2 years ago

Devot Slut Dildo sucking gag Training at 6:00 in the Morning xD

Devot Slut Dildo sucking gag Training at 6:00 in the Morning xD

xHamster 2 years ago

Home bitch humiliation and training with lizz_ss25

Home bitch humiliation and training with lizz_ss25

XXXShemalePorn 2 years ago

Sissy Horny Andrea loves jerking to my content

Sissy Horny Andrea loves jerking to my content

Sheer 1 year ago

From DoucheBag to gym Slut!

65% 0:32 / 12:29

From DoucheBag to gym Slut!

C4S 2 years ago

Charlie Cano Private Show

HD 2:00 / 27:25

Charlie Cano Private Show

Flirt4Free 2 years ago

Cross Dresser oksana riding purple monster toy chastity ejaculation part.1

Cross Dresser oksana riding purple monster toy chastity ejaculation part.1

SexTubeSpot 3 years ago

Christmas Spirit Turns U And Your Wife's Body How it Should Be [Futanari Anal JOI]

Christmas Spirit Turns U And Your Wife's Body How it Should Be [Futanari Anal JOI]

ShemaleSin 11 months ago

SOUNDING WITH ELECTRIFIED TORTURE & BREATHPLAY FOR SISSY SUB

SOUNDING WITH ELECTRIFIED TORTURE & BREATHPLAY FOR SISSY SUB

Transvids.tv 1 year ago

Sissy Slut BBC Anal Training

HD 1:01 / 12:55

Sissy Slut BBC Anal Training

FapHouse 1 month ago

Reina Hanno Anal Kegel Training Trailer

Reina Hanno Anal Kegel Training Trailer

xHamster 3 years ago

Margo-Apollo Sissymaker. Part 4, part 5 (sissymaker, sissy motivation, sissy trainer)

Margo-Apollo Sissymaker. Part 4, part 5 (sissymaker, sissy motivation, sissy trainer)

xHamster 3 months ago

Thick Step Mom Does Horrible Things to Her Step Sons! Arya Grander

Thick Step Mom Does Horrible Things to Her Step Sons! Arya Grander

xHamster 1 year ago

Cute Girl rides super huge Dildo and stretches her tiny pussy

Cute Girl rides super huge Dildo and stretches her tiny pussy

xHamster 2 years ago

Camp Sissyboi Cocksucker Lips

Camp Sissyboi Cocksucker Lips

xHamster 1 year ago

CUM & PISS CockTail - Humiliation JOI Gay Bdsm Slave Training

CUM & PISS CockTail - Humiliation JOI Gay Bdsm Slave Training

xHamster 10 months ago

Master & Christian Mckenzie & Christian Rey Private Show

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 2 years ago

High heels crossdresser anal vibrator cum

High heels crossdresser anal vibrator cum

xHamster 1 year ago

Katy Ling Private Show

HD 2:00 / 15:27

Katy Ling Private Show

Flirt4Free 3 weeks ago

Dizzy In Bondage In The Cave!

Dizzy In Bondage In The Cave!

XVideos 4 years ago

”Nin: Oriental Orgasm”

”Nin: Oriental Orgasm”

TransHero 5 years ago

sissypov - riley jay where do you want your mouth to land first porn video

sissypov - riley jay where do you want your mouth to land first porn video

TransDoe 9 months ago

Black Suck 2

FapHouse 1 year ago

DIaper Pup Pissing , AbiYinger

DIaper Pup Pissing , AbiYinger

xHamster 3 years ago

Tamara Sanders Private Show

Tamara Sanders Private Show

Flirt4Free 1 week ago

Maria Saint Private Show

Maria Saint Private Show

Flirt4Free 1 week ago

Night walk at train station and parking lot with fishnet stocking

Night walk at train station and parking lot with fishnet stocking

xHamster 3 years ago

Feminine Males Suck Masculine Cock (sissy Cocksucking PMV)

Feminine Males Suck Masculine Cock (sissy Cocksucking PMV)

TrannyGem 6 years ago

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