Training Videos - Trans (27,217)

Newbie Sissy Training: Meeting #2, Stretching Sissy Cunt with Fingers

Newbie Sissy Training: Meeting #2, Stretching Sissy Cunt with Fingers

FapHouse 10 months ago

Biggest BBC Anal Sextoy Compilation - My Much loved Toy to Ride FULL VID on LayneLovee Manyvids

Biggest BBC Anal Sextoy Compilation - My Much loved Toy to Ride FULL VID on LayneLovee Manyvids

ShemaleSin 1 year ago

Female Dominance Wifey makes Hubby Wear her Underpants for Glamour Hj with Icecube

Female Dominance Wifey makes Hubby Wear her Underpants for Glamour Hj with Icecube

TrannyGem 4 years ago

Sissification feminization sissy training - Sweethearts's feelings two (english voice)

Sissification feminization sissy training - Sweethearts's feelings two (english voice)

ShemaleSin 2 years ago

2B's Corruption Comics JOI (Shemale Hentai, assplay, breathplay, facesitting, oral job, CEI, Sissy training)

2B's Corruption Comics JOI (Shemale Hentai, assplay, breathplay, facesitting, oral job, CEI, Sissy training)

ShemaleSin 4 years ago

Dp fetish fun

xHamster 3 months ago

SISSY TRAINNING & CURRENCY-SHOTS COMPILATION

SISSY TRAINNING & CURRENCY-SHOTS COMPILATION

TransTube.tv 1 year ago

SOUNDING WITH ELECTRIFIED TORTURE & BREATHPLAY FOR SISSY SUB

SOUNDING WITH ELECTRIFIED TORTURE & BREATHPLAY FOR SISSY SUB

Transvids.tv 1 year ago

Top t-model wants a bottom whore stud

Top t-model wants a bottom whore stud

TrannyGem 2 years ago

SISSY TRAINING SESSION, MILKING MY SISSY BEFORE PEGGING HER CUTE ASS

SISSY TRAINING SESSION, MILKING MY SISSY BEFORE PEGGING HER CUTE ASS

BallsAndBoobs 5 months ago

Cuckold Bf Confession - Sorry for CUCKOLDING you

Cuckold Bf Confession - Sorry for CUCKOLDING you

MenGem 1 year ago

Rican sissyPussy uno

Rican sissyPussy uno

XXXShemalePorn 10 years ago

TRANS ANGELS - Drake Von Trains Khloe Kay A Lesson For Pounding His Gf

TRANS ANGELS - Drake Von Trains Khloe Kay A Lesson For Pounding His Gf

Transvids.tv 5 months ago

Petite Shemale Takes Big Cock Up the Ass, Employee Bitch Gets Fucked Hard

Petite Shemale Takes Big Cock Up the Ass, Employee Bitch Gets Fucked Hard

XXXShake 8 months ago

Rubberdoll Fan Controlled Hush Plug Cellmate Chastity Prostate Milking Teaser

Rubberdoll Fan Controlled Hush Plug Cellmate Chastity Prostate Milking Teaser

ShemaleSin 4 years ago

Yes you are a crossdresser!

Yes you are a crossdresser!

XXXShemalePorn 4 years ago

Lust Academy - Audrey the Trans Succubus Fucks James in Doggy Style Part 5

55% HD 1:01 / 6:11

Lust Academy - Audrey the Trans Succubus Fucks James in Doggy Style Part 5

FapHouse 3 months ago

two SIZZLING Sissy Breezies share a GINORMOUS BIG BLACK COCK in a three way

two SIZZLING Sissy Breezies share a GINORMOUS BIG BLACK COCK in a three way

TrannyGem 3 years ago

Horse Penis + Screw Machine +- Getting Screwed alongside BBC

Horse Penis + Screw Machine +- Getting Screwed alongside BBC

WebcamBros 1 year ago

Disposable Holes

Disposable Holes

xHamster 9 months ago

Shemale Cumshot Compilation: No Hands Sissy Training

Shemale Cumshot Compilation: No Hands Sissy Training

Jizzberry 3 years ago

Mastix Mercer Gagged Feminized Wench Pegging in Latex and Sissy Ding-dong Riding

Mastix Mercer Gagged Feminized Wench Pegging in Latex and Sissy Ding-dong Riding

ShemaleSin 4 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

Complete Cute Blonde Tgirl Lactating Her Tits and Punishing Her Puffy Nipples with a Vacuum Pump

HD 1:01 / 15:39

Complete Cute Blonde Tgirl Lactating Her Tits and Punishing Her Puffy Nipples with a Vacuum Pump

FapHouse 1 day ago

Slut training 1

Slut training 1

aShemaleTube 2 years ago

Whispering Latex Underware - Chastity and Shoe Worship ASMR

Whispering Latex Underware - Chastity and Shoe Worship ASMR

ShemaleSin 7 months ago

Sissy Slut Enjoys BBC, Cums Handsfree

HD 1:01 / 14:13

Sissy Slut Enjoys BBC, Cums Handsfree

FapHouse 1 month ago

Trans fuck-fest

Trans fuck-fest

TrannyGem 2 years ago

Virgin Sissy Housewife Fucked with Dildo for the First Time

Virgin Sissy Housewife Fucked with Dildo for the First Time

xHamster 8 months ago

German Teen tranny fucks her ass in dirndl with dildo

German Teen tranny fucks her ass in dirndl with dildo

xHamster 1 year ago

Cute Sissy Riding Big Dildo

Cute Sissy Riding Big Dildo

xHamster 1 year ago

Work break

xHamster 3 months ago

Sissy mega-bitch donk-shag getting off with pearl closed in purity_sc.17

Sissy mega-bitch donk-shag getting off with pearl closed in purity_sc.17

TransTube.tv 1 year ago

Step-mom teach a important lesson to her new step daughter-in-law (How to be a slut)

Step-mom teach a important lesson to her new step daughter-in-law (How to be a slut)

TransTube.tv 1 year ago

Natalie Mars Training the baby Gimp

Natalie Mars Training the baby Gimp

FetishShrine 1 year ago

CUM PEGGING and FISTING HEADMISTRESS COMPILATION

CUM PEGGING and FISTING HEADMISTRESS COMPILATION

ShemaleSin 7 months ago

Sissyfication - Bring out your feminine side with Mistress Lady Julina

Sissyfication - Bring out your feminine side with Mistress Lady Julina

Pornzona 3 months ago

XXX WOMAN PLUMB SHE-CREATURE

XXX WOMAN PLUMB SHE-CREATURE

TrannyGem 5 months ago

Sissy Femboy Munches Wc Neat While In Virginity (Preview)

Sissy Femboy Munches Wc Neat While In Virginity (Preview)

TrannyGem 2 years ago

Pantyhose Purity Sissy gets Pegged Through Ripped Nylons with Monstrous Bad Dragon Rope on faux-cock by Domina

Pantyhose Purity Sissy gets Pegged Through Ripped Nylons with Monstrous Bad Dragon Rope on faux-cock by Domina

TransTube.tv 1 year ago

POINT OF VIEW transgender princess Pummel outDoor Ppoppers and double ass fucking sqwirt

POINT OF VIEW transgender princess Pummel outDoor Ppoppers and double ass fucking sqwirt

TransTube.tv 1 year ago

Filling the Sissy Ashole with Her Own Cum After a Hard Fisting by Mistress Hands

Filling the Sissy Ashole with Her Own Cum After a Hard Fisting by Mistress Hands

xHamster 2 months ago

Strenuous SISSYGASM on phat BIG BLACK COCK fake-shaft!

Strenuous SISSYGASM on phat BIG BLACK COCK fake-shaft!

TransTube.tv 1 year ago

SometimesNiki cheerleader continues oral

SometimesNiki cheerleader continues oral

xHamster 7 months ago

sissy ass training woman penetrates husband in the ass PEGGING #88

sissy ass training woman penetrates husband in the ass PEGGING #88

Pornzona 4 weeks ago

Ash-Blonde Sissy Waits For Gang Fuck-Fest For Firm Bum Poking And Dual Anal Invasion Sissy Innocence Teaching

Ash-Blonde Sissy Waits For Gang Fuck-Fest For Firm Bum Poking And Dual Anal Invasion Sissy Innocence Teaching

TrannyGem 4 years ago

trans sissy nymph blowage’s big black cock faux-cock jessiesissyadventures

trans sissy nymph blowage’s big black cock faux-cock jessiesissyadventures

TransTube.tv 1 year ago

sissy training - bimbofication

sissy training - bimbofication

xHamster 1 year ago

steel metallic servitude,gag,anal used by BBC SADOMASOCHISM

steel metallic servitude,gag,anal used by BBC SADOMASOCHISM

ShemaleSin 4 years ago

Sasha Star Sissy Manor SOTY '23 Reward Thank u

Sasha Star Sissy Manor SOTY '23 Reward Thank u

ShemaleSin 1 year ago

Mesmeriza Compilation 12 Island of Oblivion

Mesmeriza Compilation 12 Island of Oblivion

xHamster 1 year ago

Sissy Monique - Slutwalk in the redlight district

Sissy Monique - Slutwalk in the redlight district

xHamster 2 months ago

THE SISSY INSPECTORS: #1 #2. #3. - (teasers)

THE SISSY INSPECTORS: #1 #2. #3. - (teasers)

TransTube.tv 1 year ago

Slut femboy Hattabi4ik squirt climax joy soaked booty with anal toys

Slut femboy Hattabi4ik squirt climax joy soaked booty with anal toys

ShemaleSin 4 months ago

Sissy Maid in Hot Pink Dress and Chastity Is Locked to Her Dildo Stand

Sissy Maid in Hot Pink Dress and Chastity Is Locked to Her Dildo Stand

xHamster 1 year ago

Curvy Buxom Phat-booty Femboy With Caged Cock Gets Her Anus Smashed With a Fuck-machine

Curvy Buxom Phat-booty Femboy With Caged Cock Gets Her Anus Smashed With a Fuck-machine

XGroovy 1 year ago

super-naughty Newhalf Trains Him To Take Her wang

super-naughty Newhalf Trains Him To Take Her wang

TransTube.tv 10 months ago

Instructions Anal Training

Instructions Anal Training

aShemaleTube 1 year ago

Pony Fetish Girl Pet Play Bimbo Tgirl

Pony Fetish Girl Pet Play Bimbo Tgirl

FapHouse 2 years ago

Random Sissy Hoe Vids

Random Sissy Hoe Vids

TrannyGem 2 years ago

pink vibrating ass plug! adult store parking lot! risky public naughtiness!!

pink vibrating ass plug! adult store parking lot! risky public naughtiness!!

ShemaleSin 4 years ago

HornyEmpressKay - obedience training

HornyEmpressKay - obedience training

ShemaleSin 2 years ago

Iranian femboy anal training

Iranian femboy anal training

xHamster 6 months ago

Sissy Erica Screws for Mastix Mercer with HUGE Sextoy to Exhaustion

Sissy Erica Screws for Mastix Mercer with HUGE Sextoy to Exhaustion

ShemaleSin 4 years ago

Strung Up Biker Breeds CD Sissy Fuckslut Humid

Strung Up Biker Breeds CD Sissy Fuckslut Humid

TrannyGem 2 years ago

Gay Bottom TEST - Humiliation JOI - BDSM Slave Training

Gay Bottom TEST - Humiliation JOI - BDSM Slave Training

xHamster 11 months ago

Sexy TGirl Gigi gets her ass depth trained by Lisa

Sexy TGirl Gigi gets her ass depth trained by Lisa

xHamster 2 years ago

”Dominant TS Foxxy trains Sherman Maus with assfucking play”

”Dominant TS Foxxy trains Sherman Maus with assfucking play”

LesbianBliss 1 week ago

TS Foxxy BDSM Collar Slave Training

TS Foxxy BDSM Collar Slave Training

aShemaleTube 2 weeks ago

I bang my gap and cum

I bang my gap and cum

ShemaleSin 4 weeks ago

An Booty to remember

An Booty to remember

ShemaleSin 3 years ago

FuckerMan series - All we had to do was follow the dang train! But seriously we are having sex with everyone on a train

FuckerMan series - All we had to do was follow the dang train! But seriously we are having sex with everyone on a train

XXXXCum 4 months ago

MILF TRANS SUBMISSA APANHANDO NAS BOLAS E BEBENDO MIJO

MILF TRANS SUBMISSA APANHANDO NAS BOLAS E BEBENDO MIJO

XVideos 10 months ago

Sissy Inside and Outside Anal Play

Sissy Inside and Outside Anal Play

xHamster 1 year ago

Alpha Male Femboy Sissy (M4M Gay Audio Story)

Alpha Male Femboy Sissy (M4M Gay Audio Story)

xHamster 2 years ago

Sissy in Leopard Lingerie and Chastity Plays with Her Doll

Sissy in Leopard Lingerie and Chastity Plays with Her Doll

xHamster 10 months ago

trailer Mesmeriza 23 02 MOV CINEMA CLIP 321 20240814134325039

trailer Mesmeriza 23 02 MOV CINEMA CLIP 321 20240814134325039

xHamster 4 months ago

Pervert nurse spits cum inside sissy's asshole

Pervert nurse spits cum inside sissy's asshole

xHamster 2 years ago

Crossdresser maid doing abode chores

Crossdresser maid doing abode chores

ShemaleSin 2 years ago

Sissy drinks big black cock cumload

Sissy drinks big black cock cumload

TrannyGem 2 years ago

Hattabi4ik Sissy Femboy Trap Jizz Compilation

Hattabi4ik Sissy Femboy Trap Jizz Compilation

TrannyGem 4 months ago

First-Ever Time Railing Her Faux-Cock In A FuFu Clamp

First-Ever Time Railing Her Faux-Cock In A FuFu Clamp

TrannyGem 2 years ago

Blonde Asian Transvestite Gets Cum Filled Condom in Mouth

HD 1:01 / 32:58

Blonde Asian Transvestite Gets Cum Filled Condom in Mouth

FapHouse 11 months ago

Trans person learns humiliating puppy slapping training

Trans person learns humiliating puppy slapping training

XXXShemalePorn 2 years 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”

4Wank 2 years ago

Limp clitty training

Limp clitty training

xHamster 1 month ago

Sissy BJ practice Deepthroat Training Enhanced Version

Sissy BJ practice Deepthroat Training Enhanced Version

ShemaleSin 3 years ago

On the beach, I hold my husband by his balls

On the beach, I hold my husband by his balls

xHamster 8 months ago

CD Slut in Shiny Pink Skirt and Corrset Gets Machine Fucked Until Anal Orgasm

CD Slut in Shiny Pink Skirt and Corrset Gets Machine Fucked Until Anal Orgasm

FapHouse 1 year ago

Crossdresser Bi Slut Anal Training with 2 Tunnel Plugs an Dildo Fuck Trought

HD 1:01 / 11:05

Crossdresser Bi Slut Anal Training with 2 Tunnel Plugs an Dildo Fuck Trought

FapHouse 1 year ago

SMOKING for my SISSY girlfriend and PLUGGING her sweet ass

SMOKING for my SISSY girlfriend and PLUGGING her sweet ass

Pornzona 3 weeks ago

femboy's gaping aperture teases u to a sexy climax

femboy's gaping aperture teases u to a sexy climax

Amateur8 3 weeks ago

Teen Sissy Takes Long Anal Plug – Lingerie, Stockings & Messy Femboy Cum

Teen Sissy Takes Long Anal Plug – Lingerie, Stockings & Messy Femboy Cum

XGroovy 6 months ago

Huge Bad Dragon Opportunity for Sissy Ass-Fuck Biotch Xxx Pegging with Strap Dildo by female domination Domme Mercer

Huge Bad Dragon Opportunity for Sissy Ass-Fuck Biotch Xxx Pegging with Strap Dildo by female domination Domme Mercer

TrannyGem 2 months ago

Upskirt caught in the forest

Upskirt caught in the forest

ShemaleSin 4 months ago

My New Inverted Chastity Cage Cums w/ a Tiny Fake Diik Attachment

My New Inverted Chastity Cage Cums w/ a Tiny Fake Diik Attachment

XVideos 2 years ago

CUM SISSY TRAINING

CUM SISSY TRAINING

ShemaleSin 7 months ago

She-creature fucky-fucky with domina, Transgirl Spunking Cowgirl Railing, Sissy jizz in pusssy

She-creature fucky-fucky with domina, Transgirl Spunking Cowgirl Railing, Sissy jizz in pusssy

Transvids.tv 5 months ago

Dildo Anal training

Dildo Anal training

xHamster 1 year ago

Heterosexual Latino Boy and Crossdresser Draining off together

Heterosexual Latino Boy and Crossdresser Draining off together

GayCK 5 years ago

bbc bimbo sloppy deepthroat training

bbc bimbo sloppy deepthroat training

ShemaleSin 3 years ago

July bois/men revolution

July bois/men revolution

FapHouse 3 years ago

Advanced Anal Stretching with Jasmine-dlight: Part 2 - Standing Position

69% HD 1:01 / 9:57

Advanced Anal Stretching with Jasmine-dlight: Part 2 - Standing Position

FapHouse 3 months ago

Crossdresser anal stretching and training with huge butt plugs, corsage, mini skirt, and latex stockings

Crossdresser anal stretching and training with huge butt plugs, corsage, mini skirt, and latex stockings

SexTubeSpot 1 month ago

Anal Training Sissy Asspussy Masturbation Sissygasm Large Sex-Toy Anal gape Crossdresser Femboy Tgirl

Anal Training Sissy Asspussy Masturbation Sissygasm Large Sex-Toy Anal gape Crossdresser Femboy Tgirl

ShemaleSin 3 years ago

BDSM TS Sissy Slave Rough Sex Compilation - Shemales Fucked Hard with Fetish Toys

BDSM TS Sissy Slave Rough Sex Compilation - Shemales Fucked Hard with Fetish Toys

xHamster 1 year ago

Sissy Tutor Encouragement Crossdresser BBC Interracial Fiona Fortune

Sissy Tutor Encouragement Crossdresser BBC Interracial Fiona Fortune

ShemaleSin 1 month ago

Anal fisting belladonnas magic hand par2

Anal fisting belladonnas magic hand par2

xHamster 4 years ago

Boning my thick arse with a fuckmachine

Boning my thick arse with a fuckmachine

TrannyGem 11 months ago

Sissy Whore Anal Training Big Dildos

Sissy Whore Anal Training Big Dildos

aShemaleTube 2 years ago

Sissy faggot bitch

Sissy faggot bitch

xHamster 1 year ago

Im gonna turn you into a blower and put you on the street sissy boi SHE-MALE PIMP VERSION

Im gonna turn you into a blower and put you on the street sissy boi SHE-MALE PIMP VERSION

TrannyGem 7 months ago

Gigantic Dildo Clyde

Gigantic Dildo Clyde

xHamster 1 month ago

Big Ass Sissy in Asuka Cosplay Anal Fucked with BBC Dildo and Plugged

Big Ass Sissy in Asuka Cosplay Anal Fucked with BBC Dildo and Plugged

FapHouse 1 week ago

Gothic Witch takes trio Gigantic Fake Penises

Gothic Witch takes trio Gigantic Fake Penises

TrannyGem 3 years ago

Super-Steamy legitimate yr older nymph plays with a hefty banana

Super-Steamy legitimate yr older nymph plays with a hefty banana

TrannyGem 3 years ago

Hawt Secret Agent Captured and Hogtied

Hawt Secret Agent Captured and Hogtied

ShemaleSin 2 years ago

Mommy Dom Sissy Training JOI

Mommy Dom Sissy Training JOI

AbTranny 6 years ago

The Well Used Hole missavablack & obeyladymk Use Jasmine Dlight's Bottomless Pit

The Well Used Hole missavablack & obeyladymk Use Jasmine Dlight's Bottomless Pit

xHamster 11 months ago

Halloween Killer Angel Sissy Superslut Lola getting mouth penetrated by big black cock

Halloween Killer Angel Sissy Superslut Lola getting mouth penetrated by big black cock

TransTube.tv 1 year ago

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