Training Videos - Trans (27,732)

NAPPY slave receives SPANKING penalty

NAPPY slave receives SPANKING penalty

KAMS 7 months ago

Summertime Saga Part 180 - Future by MissKitty2K

Summertime Saga Part 180 - Future by MissKitty2K

xHamster 5 months ago

Spectacular moment from "2 huge hands free cumshots in a row"

Spectacular moment from "2 huge hands free cumshots in a row"

xHamster 4 months ago

Virginity cell assfucking

Virginity cell assfucking

TrannyGem 1 month ago

becomingfemme - natty submissive sissy for football season

becomingfemme - natty submissive sissy for football season

TransDoe 2 years ago

He lost his v-card by getting porked rock hard

He lost his v-card by getting porked rock hard

TransTube.tv 1 year ago

Cum Injection and Big Toys for the Perfect Pegging Sissygasm

Cum Injection and Big Toys for the Perfect Pegging Sissygasm

xHamster 1 month ago

Lizz_ss25 home doxy humiliation and training

Lizz_ss25 home doxy humiliation and training

ShemaleSin 3 years ago

Slutty crossdresser opens his anal pussy with huge anal plugs and fisting

Slutty crossdresser opens his anal pussy with huge anal plugs and fisting

xHamster 1 year ago

Independent training No75 Milk enema walks

Independent training No75 Milk enema walks

xHamster 6 days ago

Sissy Elvi Lynx Huge Anal Gape with Anal Plug

Sissy Elvi Lynx Huge Anal Gape with Anal Plug

FapHouse 3 weeks ago

Sonechka25 Showed Her Asshole to a Stranger for. Sissy Training 3.

Sonechka25 Showed Her Asshole to a Stranger for. Sissy Training 3.

xHamster 3 months ago

Sissy Dani Hard Assfuck Training PT 2 (Humid Audio) (HD)

Sissy Dani Hard Assfuck Training PT 2 (Humid Audio) (HD)

TransTube.tv 1 year ago

Super-Cute Sissy Lola SADISM & MASOCHISM Restrain Bondage Hump Sub UK Nasty Mega-Slut / FREE-FOR-ALL OF @SISSYTRAPQUEEN

Super-Cute Sissy Lola SADISM & MASOCHISM Restrain Bondage Hump Sub UK Nasty Mega-Slut / FREE-FOR-ALL OF @SISSYTRAPQUEEN

TrannyGem 2 years ago

POINT OF VIEW Micro Man Rod Sissy Bi-Atch Plays With Snapchat Filters

POINT OF VIEW Micro Man Rod Sissy Bi-Atch Plays With Snapchat Filters

TrannyGem 2 months ago

cumshot compilation free hands sissygasm

cumshot compilation free hands sissygasm

AnalVids 10 months ago

Honey, TransMommy needs your rump again

Honey, TransMommy needs your rump again

TransTube.tv 1 year ago

Feminized By New Stepdad - A Sissy Caption Story ????????????

Feminized By New Stepdad - A Sissy Caption Story ????????????

TransTube.tv 1 year ago

SISSY IS BROUGHT TO UNREAL ORGASMS by BIG Hankey&#039_s Toys

SISSY IS BROUGHT TO UNREAL ORGASMS by BIG Hankey&#039_s Toys

XVideos 1 year ago

BRAZZERS Exxtra - Brown hair Moriah Mills enjoys cumshot

BRAZZERS Exxtra - Brown hair Moriah Mills enjoys cumshot

WankTubeTV 4 years ago

Latex Sissy Maid Candy in Chastity and Bondage Stuck on a Fucking Machine

Latex Sissy Maid Candy in Chastity and Bondage Stuck on a Fucking Machine

xHamster 1 year ago

Shiri's First Gangbang: Gym Slut Takes 5

Shiri's First Gangbang: Gym Slut Takes 5

FapHouse 4 years ago

POV changing flat chastity with urethral plug to small chastity cage

POV changing flat chastity with urethral plug to small chastity cage

xHamster 1 year ago

Hard Anal Training for Lana Trap

Hard Anal Training for Lana Trap

ShemaleSin 4 years ago

Lady Fyre's School for Boys and Good Sissies

Lady Fyre's School for Boys and Good Sissies

xHamster 1 year ago

Sissy Makeover by your TS StepMom

Sissy Makeover by your TS StepMom

aShemaleTube 11 months ago

Hard Fucked Fuckmachine

Hard Fucked Fuckmachine

xHamster 1 month ago

Extreme Gaping and Stretching my Poor Femboy Ass

Extreme Gaping and Stretching my Poor Femboy Ass

xHamster 3 months ago

I screw u with my sissy wench

I screw u with my sissy wench

ShemaleSin 9 months ago

Sissy in Black Lingerie Gets Fucked by Her Fucking Machine

Sissy in Black Lingerie Gets Fucked by Her Fucking Machine

xHamster 3 weeks ago

Powerful moment from "Mistress gonna transform you in a sissy fucktoy and make your ass sore (FEMINIZATION ROLEPLAY - AI"

Powerful moment from "Mistress gonna transform you in a sissy fucktoy and make your ass sore (FEMINIZATION ROLEPLAY - AI"

xHamster 9 months ago

Horny whore wants more dick in her asspussy

Horny whore wants more dick in her asspussy

xHamster 1 week ago

Wife teaches and trains feminised sissy husband to become a BBC slut

Wife teaches and trains feminised sissy husband to become a BBC slut

aShemaleTube 1 year ago

Bound Sissy Gets Cock Milked Then Fed Her Own Load of Cum - Jessica Bloom and Polieana

HD 1:01 / 15:09

Bound Sissy Gets Cock Milked Then Fed Her Own Load of Cum - Jessica Bloom and Polieana

FapHouse 5 months ago

Scarlett Ocean PMV - Shemale and 12 Inch Dildo

Scarlett Ocean PMV - Shemale and 12 Inch Dildo

xHamster 2 years ago

Joy Feminization

Joy Feminization

TrannyGem 2 months ago

Ana Lisa 32

xHamster 1 year ago

Faux-Cock experience 1

Faux-Cock experience 1

TrannyGem 2 years ago

Cross dressing sissy whore Trisha Trash stuffs her ass and practices deep throating

Cross dressing sissy whore Trisha Trash stuffs her ass and practices deep throating

xHamster 2 months ago

Asian Twink Army Anal Training

Asian Twink Army Anal Training

xHamster 1 year ago

Behind the scenes | Bastidores | Exclusive for Subscribers | Ts Vanessa Rafaella

Behind the scenes | Bastidores | Exclusive for Subscribers | Ts Vanessa Rafaella

XVideos 1 year ago

Sissy rectal climax

Sissy rectal climax

TrannyGem 1 year ago

Domina makes sissy from girlz professional gargle fake penis and then plows her rear end fashion

Domina makes sissy from girlz professional gargle fake penis and then plows her rear end fashion

TrannyGem 1 year ago

Big Step Sister Girlfriend Training - Natasha Nice -Family Therapy - Alex Adams

Big Step Sister Girlfriend Training - Natasha Nice -Family Therapy - Alex Adams

FapCat 2 years ago

Superslut walk, wedgie

Superslut walk, wedgie

TrannyGem 1 year ago

Fuck Your Ass - Sissy Training (Sissy Audio Hypnose)

Fuck Your Ass - Sissy Training (Sissy Audio Hypnose)

YouPorn Unknown

Giant bum candid upskirt, moving purity key to a bus stop

Giant bum candid upskirt, moving purity key to a bus stop

TrannyGem 1 year ago

Sissy Twink CD Anal Dildo Training

Sissy Twink CD Anal Dildo Training

xHamster 3 years ago

Pink Satin Sissy Maid Gets Fucked by Her Fucking Machine and Plays with Her Sex Toy Doll

Pink Satin Sissy Maid Gets Fucked by Her Fucking Machine and Plays with Her Sex Toy Doll

xHamster 2 weeks ago

Fucking huge and swallowing dildos

Fucking huge and swallowing dildos

xHamster 2 years ago

Small Sissy Cock Critted

Small Sissy Cock Critted

xHamster 1 year 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

Domina Instructing Horny Sissy Mega-Bitch

Domina Instructing Horny Sissy Mega-Bitch

TrannyGem 4 years ago

Lexi Avalon Face Fuck part 7

Lexi Avalon Face Fuck part 7

xHamster 3 years ago

Pegging, and Fisting, and Toys, OH MY! (15min of 72min full scene)

Pegging, and Fisting, and Toys, OH MY! (15min of 72min full scene)

Juicexxx 1 year ago

[metavulgar] - abdl, tractable roleplay, bottle feeding, collar, feminization ASMR, adult baby roleplay - full version on my patreon page - sissy, joi, cuckold, findom

[metavulgar] - abdl, tractable roleplay, bottle feeding, collar, feminization ASMR, adult baby roleplay - full version on my patreon page - sissy, joi, cuckold, findom

ShemaleSin 5 months ago

Turning my cock inside out to wear a female chastity belt

Turning my cock inside out to wear a female chastity belt

xHamster 4 years ago

Anal inflatable giant dildo

Anal inflatable giant dildo

xHamster 1 year ago

”Diesel Ravaged Me!”

”Diesel Ravaged Me!”

TransHero 4 weeks ago

Sissy wearing buttplug tail out for a walk

Sissy wearing buttplug tail out for a walk

ShemaleSin 1 year ago

Feminization Sissy training Female energy for faggot

Feminization Sissy training Female energy for faggot

ShemaleSin 1 year ago

Heathrow Dungeon Part 3 - Throat Fuckers for Sucking Too Much Cock

Heathrow Dungeon Part 3 - Throat Fuckers for Sucking Too Much Cock

xHamster 10 months ago

Mirror Anal Play

Mirror Anal Play

SortPorn 4 months ago

Wearing explicit pink stuff curvy Tgirl Andrea Dimaggio wins boner cock

Wearing explicit pink stuff curvy Tgirl Andrea Dimaggio wins boner cock

XCafe 5 years ago

DRAGON BALL SUPER - LOST EPISODE P1 - Masturbation and Rough Fuck By MissKitty2K

DRAGON BALL SUPER - LOST EPISODE P1 - Masturbation and Rough Fuck By MissKitty2K

xHamster 1 year ago

sissypov - jossilyn swallows sisy eye contact sex porn video

sissypov - jossilyn swallows sisy eye contact sex porn video

TransDoe 1 year ago

Fully sissified bitch boi gets dominated and pegged

Fully sissified bitch boi gets dominated and pegged

xHamster 6 months ago

Sissy teasing and dildo riding on balcony

Sissy teasing and dildo riding on balcony

BallsAndBoobs 4 months ago

Dreamscape Sissy training

Dreamscape Sissy training

Sheshaft 2 years ago

[metavulgar] - lingerie, lingerie fetish, femdom, lingerie worship, domination, spanking ASMR - full version on my patreon page - sissy, joi, cuckold, findom

[metavulgar] - lingerie, lingerie fetish, femdom, lingerie worship, domination, spanking ASMR - full version on my patreon page - sissy, joi, cuckold, findom

PornFreeNow 5 months ago

White Glove Pleasure

White Glove Pleasure

PornFreeNow 2 months ago

Live-webcam Replay - Pegging my Marionette in V-Card ! Subsribe to observe total Vid of 1hour Domina Julia

Live-webcam Replay - Pegging my Marionette in V-Card ! Subsribe to observe total Vid of 1hour Domina Julia

TrannyGem 1 year ago

Sissy Biotch getting fap hammerred by BIG BLACK COCK

Sissy Biotch getting fap hammerred by BIG BLACK COCK

TrannyGem 3 years ago

Oral Training

xHamster 3 weeks ago

Self-Training No35 Machine Masturbation

Self-Training No35 Machine Masturbation

xHamster 1 month ago

Sissy Transgirl in Handcuffs Anal Fucked by Big Black Dildo in her Girly Fat Ass until her Asshole Gapes

Sissy Transgirl in Handcuffs Anal Fucked by Big Black Dildo in her Girly Fat Ass until her Asshole Gapes

xHamster 4 months ago

Bathroom quickie Crossdresser anal stretch

Bathroom quickie Crossdresser anal stretch

xHamster 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 3 years ago

misr4 - Riding anal dildo in black stockings

misr4 - Riding anal dildo in black stockings

xHamster 5 months ago

Sissy Faggot Jes Brinch Exposed Whore

Sissy Faggot Jes Brinch Exposed Whore

xHamster 6 months ago

practice makes perfect

practice makes perfect

xHamster 1 year ago

Star Lewd Valley - Part 1 - Sexy Village Girls By LoveSkySanHentai

Star Lewd Valley - Part 1 - Sexy Village Girls By LoveSkySanHentai

xHamster 1 year ago

Whorish Teenager Crossdresser Sophie Getting Ravaged by Enormous Dinky

Whorish Teenager Crossdresser Sophie Getting Ravaged by Enormous Dinky

TrannyGem 10 months ago

becomingfemme - quinn tesla tgirl living his best life

becomingfemme - quinn tesla tgirl living his best life

TransDoe 1 year ago

Sounding and Prostate Exam - Fisting

Sounding and Prostate Exam - Fisting

xHamster 10 months ago

domina makes a sub inhale a protection spunk-pump and plumbs her hand in the ass

domina makes a sub inhale a protection spunk-pump and plumbs her hand in the ass

Transvids.tv 1 year ago

Jade Venus giving Roman Todd CPR training

Jade Venus giving Roman Todd CPR training

PornDR 1 year ago

AB026 Mistress training abby by wooden pony ,anal plug -cum TS女优艾比绳缚拘束骑乘木马电动肛塞被Maya女王调教高潮喷发-BDSM

AB026 Mistress training abby by wooden pony ,anal plug -cum TS女优艾比绳缚拘束骑乘木马电动肛塞被Maya女王调教高潮喷发-BDSM

aShemaleTube 5 years ago

two Dommes and their trans whore! Thrashing, FemDom, Humiliation

two Dommes and their trans whore! Thrashing, FemDom, Humiliation

Amateur8 2 months ago

Hot TS Venus Lux trains newbie Javier LoveTongue with her raw cock

Hot TS Venus Lux trains newbie Javier LoveTongue with her raw cock

Yeswegays 7 months ago

Dildo Training deutsch

Dildo Training deutsch

Tranny.one 2 years ago

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

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

xHamster 4 months ago

Isabella love's penis desires

66% HD 1:01 / 8:52

Isabella love's penis desires

FapHouse 3 years ago

Desperately trying to sissygasm with my limp clitty. Chastity training is so worth it for a sissy

Desperately trying to sissygasm with my limp clitty. Chastity training is so worth it for a sissy

aShemaleTube 4 months ago

Pegging, and Fisting, and Toys, OH MY! (15min of 72min full scene)

Pegging, and Fisting, and Toys, OH MY! (15min of 72min full scene)

Pornzona 5 months ago

Bimbo Sexy Trans Transformation

63% HD 1:01 / 10:10

Bimbo Sexy Trans Transformation

FapHouse 6 months ago

Backyard Sneaky BBC suck

Backyard Sneaky BBC suck

ShemaleSin 4 years ago

Cute Sissy Lola SADOMASOCHISM Servitude Sex Thrall UK Nasty Bitch / FREE OF @SISSYTRAPQUEEN

Cute Sissy Lola SADOMASOCHISM Servitude Sex Thrall UK Nasty Bitch / FREE OF @SISSYTRAPQUEEN

ShemaleSin 1 year ago

His Personal Fucktoy

His Personal Fucktoy

ShemaleSin 2 months ago

WVM - PART 65 - RAUGH AND SEXY By MissKitty2K

WVM - PART 65 - RAUGH AND SEXY By MissKitty2K

xHamster 1 year ago

Plapping Cumshot And Cum Swallow Locktober Sissy Slut Jessica Bloom

Plapping Cumshot And Cum Swallow Locktober Sissy Slut Jessica Bloom

xHamster 2 months ago

Red Stockings White Heels and a Big Dildo

Red Stockings White Heels and a Big Dildo

xHamster 3 months ago

Chocolate ENEMAS for SISSY's mouth

Chocolate ENEMAS for SISSY's mouth

xHamster 1 year ago

Masked Sissy Crossdresser in Costume and Nylons and Corset Underware

Masked Sissy Crossdresser in Costume and Nylons and Corset Underware

ShemaleSin 3 days ago

Oops, my panties ripped right in the ass, my personal coach screwed me right there in the gym.

Oops, my panties ripped right in the ass, my personal coach screwed me right there in the gym.

ShemaleSin 2 days ago

Sexy Sissy Ponyboy Showing His Nude Body and High Heels

63% 1:01 / 5:49

Sexy Sissy Ponyboy Showing His Nude Body and High Heels

FapHouse 1 year ago

The mother I'd like to fuck went out late at night and look what happened.

The mother I'd like to fuck went out late at night and look what happened.

ShemaleSin 2 months ago

Sheer Delights

xHamster 2 years ago

Chastity April - You Belong In Panties... Dirty talking to my Sub

Chastity April - You Belong In Panties... Dirty talking to my Sub

Pornzona 2 weeks ago

Lick Cummies Movie

Lick Cummies Movie

Transvids.tv 1 year ago

Anoniema's Slutschool Oiled and femboyant Black booty slut

Anoniema's Slutschool Oiled and femboyant Black booty slut

xHamster 3 months ago

Puppy Training Lessons: Lesson 1

Puppy Training Lessons: Lesson 1

2BGay 1 year ago

Sissy slut training continues

Sissy slut training continues

Pornzona 3 weeks ago

My Recent Sissy Shemale Anal Floozy 1st Time being Feminized and Drilled by Mastix Mercer

My Recent Sissy Shemale Anal Floozy 1st Time being Feminized and Drilled by Mastix Mercer

ShemaleSin 5 months ago

Honeypot boy maid tries to keep composure while getting machine torn up

Honeypot boy maid tries to keep composure while getting machine torn up

TransTube.tv 1 year ago

Powerful moment from "Sissy Compilation Outside drinking and pussy fuck in Public"

Powerful moment from "Sissy Compilation Outside drinking and pussy fuck in Public"

xHamster 4 months ago

Big Girls Playing Big Black Toys

Big Girls Playing Big Black Toys

xHamster 3 months ago

Cd mandy 5 sextoy anal training

Cd mandy 5 sextoy anal training

XXXShemalePorn 5 years ago

The dominatrix wife dressed up her sissy husband and had fuck with him on Halloween.

The dominatrix wife dressed up her sissy husband and had fuck with him on Halloween.

Pornzona 1 month ago

Summer Rayne - Summer Training

Summer Rayne - Summer Training

Fapnado 3 years ago

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