Training Videos - Trans (89,564)

Cafe Sub Slut's Massive Tits Nip Slip Downblouse Gush Destroyed

Cafe Sub Slut's Massive Tits Nip Slip Downblouse Gush Destroyed

DarkFetishTube 4 days ago

Sissy Anal Training Session!

HD 0:39 / 13:56

Sissy Anal Training Session!

FapHouse 3 years ago

becomingfemme - naomi you look so good with your cock out porn video

becomingfemme - naomi you look so good with your cock out porn video

TransDoe 1 year ago

Chastity Sissy Maid Sissygasms Hard Riding Doll Cock Destroyed

Chastity Sissy Maid Sissygasms Hard Riding Doll Cock Destroyed

JuicyTrans 2 weeks ago

Sophia Loreen Party on Apr 6, 2026 - Part 2

55% HD 2:00 / 27:06

Sophia Loreen Party on Apr 6, 2026 - Part 2

Flirt4Free 2 weeks ago

Big Model Muscled Bodybuilder Flexing Show

49% HD 2:00 / 10:24

Big Model Muscled Bodybuilder Flexing Show

Flirt4Free 10 years ago

”TS aerobic trainer fucks blonde cougar - Kenzie Taylor & Kayleigh Coxx”

”TS aerobic trainer fucks blonde cougar - Kenzie Taylor & Kayleigh Coxx”

4Wank 3 years ago

BLACK TGIRLS - Tools of Temptation Vixen Coxx & Papi

BLACK TGIRLS - Tools of Temptation Vixen Coxx & Papi

xHamster 7 months 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 2 weeks ago

Crhistian Fucked by a Friend

Crhistian Fucked by a Friend

Flirt4Free 8 years ago

Little Trap in Pink Petticoat and White Nylons Rides on Biggest Sextoy and Cums!

Little Trap in Pink Petticoat and White Nylons Rides on Biggest Sextoy and Cums!

ShemaleSin 5 years ago

After Basketball Training We Had a Quick Fuck During Shower

72% HD 1:01 / 8:02

After Basketball Training We Had a Quick Fuck During Shower

FapHouse 7 months ago

Lady Becky Teaches Sissy Slut Michelle to Masturbate in a Proper Way

Premium HD 48:47

Lady Becky Teaches Sissy Slut Michelle to Masturbate in a Proper Way

Sheer 2 years ago

Dominatrix Nika tied up Sissy Blaire_18 with ropes and plays with his nipples. Gag and scratching

Dominatrix Nika tied up Sissy Blaire_18 with ropes and plays with his nipples. Gag and scratching

xHamster 11 months ago

Femboy training part 1: The Back Arch

Femboy training part 1: The Back Arch

Gayhub 1 year 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

TRANS FUCKED GIRLFRIEND IN THE ASS!

TRANS FUCKED GIRLFRIEND IN THE ASS!

xnxxGold 1 year ago

OPEN UP AND SWALLOW, REAL FUTANARI TAKER POV RUSSIAN MISTRESS. EVELYN ROSE

OPEN UP AND SWALLOW, REAL FUTANARI TAKER POV RUSSIAN MISTRESS. EVELYN ROSE

Pornzona 6 days ago

Lady Alice (9:16) 16 Part 02

Lady Alice (9:16) 16 Part 02

xHamster 2 years ago

Ali Da Reaper pummeling my taut tiny sissy crevasse with his big black cock

Ali Da Reaper pummeling my taut tiny sissy crevasse with his big black cock

TrannyGem 3 years ago

Sabrina Smiith Private Show

Sabrina Smiith Private Show

Flirt4Free 3 months ago

Jasmine_dlight First Footing - Extreme Anal Insertions Foot Entirely up My Butt, Deep Insertion Anal Training Butt Slut

62% HD 0:39 / 3:07

Jasmine_dlight First Footing - Extreme Anal Insertions Foot Entirely up My Butt, Deep Insertion Anal Training Butt Slut

FapHouse 1 year ago

FINDOM FOR COCK

57% HD 0:10 / 10:08

FINDOM FOR COCK

LoyalFans 3 years ago

I Fucked My New Toy, and I Left All My Cum Inside It

61% HD 2:00 / 4:00

I Fucked My New Toy, and I Left All My Cum Inside It

Flirt4Free 3 years ago

Naruto Sarada feet and ass play trap cosplay

63% HD 1:01 / 23:02

Naruto Sarada feet and ass play trap cosplay

FapHouse 4 years ago

Sorority Girls StrapOn Hazing

55% HD 0:10 / 13:01

Sorority Girls StrapOn Hazing

LoyalFans 10 months ago

Sissy Training by Queen Daralis Part 3

56% HD 0:39 / 9:18

Sissy Training by Queen Daralis Part 3

FapHouse 2 months ago

Sissy Supah-mega-slut gets Drilled by BIG BLACK COCK

Sissy Supah-mega-slut gets Drilled by BIG BLACK COCK

TransTube.tv 1 year ago

Jasmin Keur & Rick Fix Private Show

Jasmin Keur & Rick Fix Private Show

Flirt4Free 1 year ago

High heels crossdresser hands free prostate orgasm cumshot

High heels crossdresser hands free prostate orgasm cumshot

xHamster 1 year ago

The Seductive Twist: Daisy Taylor's Rebellious Massage Adventure

The Seductive Twist: Daisy Taylor's Rebellious Massage Adventure

Eporner 1 year ago

My Beautiful Ass for U

My Beautiful Ass for U

Flirt4Free 7 months ago

Sissygasm w Ava Venom

52% HD 0:10 / 8:51

Sissygasm w Ava Venom

LoyalFans 10 months ago

Stop! Feminine Sissy's Don't Jerk Off Their Cocks – Sissy Training & Feminisation with Lady Julina

Stop! Feminine Sissy's Don't Jerk Off Their Cocks – Sissy Training & Feminisation with Lady Julina

Pornzona 1 month ago

Web camera sadomasochism sissy floozy Alina shows how that babe wishes to suck and deepthroat real dong

Web camera sadomasochism sissy floozy Alina shows how that babe wishes to suck and deepthroat real dong

BigTitsLust 3 weeks ago

Domina turns you into one of her bunny damsels and lets you deep-throat your first-ever customer (FEMALE DOMINATION ROLEPLAY - AI GENERATED)

Domina turns you into one of her bunny damsels and lets you deep-throat your first-ever customer (FEMALE DOMINATION ROLEPLAY - AI GENERATED)

HentaiGem 11 months ago

Hablando Espaol!🍌💥💌

63% HD 2:00 / 5:12

Hablando Espaol!🍌💥💌

Flirt4Free 3 years ago

Flipflop Sucking

Flipflop Sucking

Flirt4Free 3 months ago

Liam Jacobson Private Show

61% HD 2:00 / 8:50

Liam Jacobson Private Show

Flirt4Free 5 months ago

Let's Train Together

Let's Train Together

FapHouse 7 months ago

Sissy bitch boi gets his ass pounded and stretched by mistresses big strapon

Sissy bitch boi gets his ass pounded and stretched by mistresses big strapon

xHamster 2 years ago

Bulls Paying for Your Pink Panties

Bulls Paying for Your Pink Panties

xHamster 5 months ago

CURVY LADYBOY ANAL CASTING AND SLAVE TRAINING | XDOMINANT

Premium HD 18:15

CURVY LADYBOY ANAL CASTING AND SLAVE TRAINING | XDOMINANT

XVideosRed 1 year ago

Nelly Gale Private Show

69% 4K 2:00 / 17:49

Nelly Gale Private Show

Flirt4Free 1 month ago

extreme Nipple Play

extreme Nipple Play

Tranny.one 3 years ago

HARD FUCKING AND FISTING OF A CROSSDRESSER IN A CHASTITY BELT! FEMINIZATION. SISSIFICATION.

Premium HD 8:05

HARD FUCKING AND FISTING OF A CROSSDRESSER IN A CHASTITY BELT! FEMINIZATION. SISSIFICATION.

Sheer 3 years ago

”Sissy Bimbo Training”

”Sissy Bimbo Training”

4Wank 1 year ago

Vladasexytrans Hard Anal Play in White Stockings

Vladasexytrans Hard Anal Play in White Stockings

xHamster 6 months ago

Feminization Sissyfication Sissy training - Dong Worship - resigned sissy

Feminization Sissyfication Sissy training - Dong Worship - resigned sissy

ShemaleSin 1 year ago

Alejandra Fox Private Show

Alejandra Fox Private Show

Flirt4Free 7 years ago

”Baseball Coach Blasts Jada with his Big White Bat”

”Baseball Coach Blasts Jada with his Big White Bat”

ThePornstar 10 months ago

Practice Makes Perfect

Practice Makes Perfect

xHamster 3 weeks ago

Sissygasm Doxy Caged Training Giant Spunk Flow & Anal Milking Jessica Bloom

Sissygasm Doxy Caged Training Giant Spunk Flow & Anal Milking Jessica Bloom

ShemaleSin 4 years ago

Intense Anal Training Session with Huge Toys & POV Sissygasm - full video on LayneLovee Manyvids

Intense Anal Training Session with Huge Toys & POV Sissygasm - full video on LayneLovee Manyvids

xHamster 1 year ago

Luccas & Jhordy & Master Private Show

58% HD 2:00 / 12:04

Luccas & Jhordy & Master Private Show

Flirt4Free 2 months ago

Busty Snowwhite - Smoking Hot

Busty Snowwhite - Smoking Hot

FapHouse 1 day ago

Trans Eva Joi Gets Dominated by TS Ria Bentley With Double Anal Toy

Trans Eva Joi Gets Dominated by TS Ria Bentley With Double Anal Toy

ShemaleSin 2 years ago

Transdom mistress throatfucks bae

Transdom mistress throatfucks bae

Some.Porn 1 year ago

femboy twink in chastity gets fucked by 12 inches while wearing a bodysuit

femboy twink in chastity gets fucked by 12 inches while wearing a bodysuit

xHamster 1 year ago

Sara & Elver Private Show

63% HD 2:00 / 6:56

Sara & Elver Private Show

Flirt4Free 2 months ago

sissy discipline: queen elena trains sissy femme sandy with flogger & paddle

sissy discipline: queen elena trains sissy femme sandy with flogger & paddle

PornBox 3 weeks ago

Humiliating Edging for Chastity serf

Humiliating Edging for Chastity serf

ShemaleSin 11 months ago

Sissy Daily Basics: Some ass-fuck joy in innocence

Sissy Daily Basics: Some ass-fuck joy in innocence

TrannyGem 3 years ago

Bi MMF Anal trains compilation

Bi MMF Anal trains compilation

aShemaleTube 3 years ago

Sissy bitch boi gets his ass pounded and stretched by mistresses big strapon

Sissy bitch boi gets his ass pounded and stretched by mistresses big strapon

Tranny.one 1 year ago

Alicia quinn super-naughty doll

Alicia quinn super-naughty doll

TrannyGem 3 years ago

Yoga Girls: Sweaty Armpit Sniffing & Strap-on Fucking

HD 1:01 / 27:02

Yoga Girls: Sweaty Armpit Sniffing & Strap-on Fucking

FapHouse 1 week ago

2 black african hotel maid sucking white dicks as a special service in interracial orgy sex group

2 black african hotel maid sucking white dicks as a special service in interracial orgy sex group

xHamster 2 years ago

pec play

Flirt4Free 14 years ago

Foursome Group Sex Fuckfest

Foursome Group Sex Fuckfest

xHamster 2 months ago

Molly & Ostin Moon Private Show

HD 2:00 / 20:29

Molly & Ostin Moon Private Show

Flirt4Free 3 years ago

Angel Nazz Private Show

Angel Nazz Private Show

Flirt4Free 1 year ago

Pure girl in a sailor dress and long socks trains her own anus with anal fisting and a huge anal plug

HD 0:39 / 12:00

Pure girl in a sailor dress and long socks trains her own anus with anal fisting and a huge anal plug

FapHouse 1 month ago

$We Love Sucking Each Other\'s Cocks$ 4K 2:00 / 5:32

We Love Sucking Each Other\'s Cocks

Flirt4Free 1 month ago

becomingfemme - jennifer lunden cumming this way feels so good porn video

becomingfemme - jennifer lunden cumming this way feels so good porn video

TransDoe 1 year ago

Elias & Elix Private Show

65% HD 2:00 / 11:17

Elias & Elix Private Show

Flirt4Free 6 months ago

Trans Ria Bentley Trains Stepdaughter Eden Espi for Anal Sex

Trans Ria Bentley Trains Stepdaughter Eden Espi for Anal Sex

xHamster 1 year ago

sentindo no pelo o cuzinho delicioso da Solzinha

Premium HD 21:44

sentindo no pelo o cuzinho delicioso da Solzinha

XVideosRed 3 months ago

Powerful Futanari DOMINATES you! 'Night Of Pleasure And Domination With Lola' [SAMPLECUT]

Powerful Futanari DOMINATES you! 'Night Of Pleasure And Domination With Lola' [SAMPLECUT]

Eporner 11 months ago

Alejandra Fox Private Show

63% HD 2:00 / 17:54

Alejandra Fox Private Show

Flirt4Free 3 years ago

Big Black Cock bull use femboy sissy phat culo rear end then breed it missionary noisy screaming tramp firm moist romping

Big Black Cock bull use femboy sissy phat culo rear end then breed it missionary noisy screaming tramp firm moist romping

Gay4Porn 1 year ago

Uk crossdresser in training 3

Uk crossdresser in training 3

GayCK 2 years ago

Punished Slaves BDSM Bondage Gay Amador Big Dick - 1

Punished Slaves BDSM Bondage Gay Amador Big Dick - 1

xHamster 1 month ago

Sissified by my recent Roomate (Sissy caption Story)

Sissified by my recent Roomate (Sissy caption Story)

ShemaleSin 4 years ago

Top ladyboy wants a bottom bitch boy

Top ladyboy wants a bottom bitch boy

Pornzona 1 month ago

Rikki Ocean Adds Her Own Homemade Cream to Her Cupcake and Eats It

Rikki Ocean Adds Her Own Homemade Cream to Her Cupcake and Eats It

xHamster 2 years ago

Self-Training No37 Daily morning exposure walk with stockings straight on

Self-Training No37 Daily morning exposure walk with stockings straight on

xHamster 4 months ago

Captain Castle: Tgirl Sailor Butt Fuck Facial

HD 0:39 / 31:30

Captain Castle: Tgirl Sailor Butt Fuck Facial

FapHouse 6 months ago

Bnwo Sissy Bride Gooning

69% HD 1:01 / 12:06

Bnwo Sissy Bride Gooning

FapHouse 7 months ago

Anal dildo machine cum

Anal dildo machine cum

xHamster 1 year ago

My Ramrod Own Your Holes Femdom Sissy ASMR JOI BINAURAL BRAINWAVES

My Ramrod Own Your Holes Femdom Sissy ASMR JOI BINAURAL BRAINWAVES

ShemaleSin 8 hours ago

Timid Lara plays with 2 FUCKTOYS and PACKS CREVICE with UNDIES

Timid Lara plays with 2 FUCKTOYS and PACKS CREVICE with UNDIES

Gay4Porn 1 month ago

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 17

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 17

xHamster 1 year ago

Sissy slut riding huge BBC dildo

Sissy slut riding huge BBC dildo

xHamster 1 year ago

Sissy Crossdress Stiffy Adore ft Trans Girl dom

Sissy Crossdress Stiffy Adore ft Trans Girl dom

TransTube.tv 1 year ago

POINT OF VIEW Emo Step-sista Feminizes You Into Her Intimate Sissy Damsel

POINT OF VIEW Emo Step-sista Feminizes You Into Her Intimate Sissy Damsel

TrannyGem 1 year ago

Mistress is fantasizing about stretching your tight fucking boypussy (FEMINIZATION ROLEPLAY - AI GENERATED)

Mistress is fantasizing about stretching your tight fucking boypussy (FEMINIZATION ROLEPLAY - AI GENERATED)

xHamster 10 months ago

Training To Become A Sissy Cuckold

Training To Become A Sissy Cuckold

PePorn 6 months ago

teen transgirl BBC training in chastity

teen transgirl BBC training in chastity

ShemaleSin 1 year ago

”Drivers class ends with a hard assfucking - Finn Harding , Amanda Riley”

”Drivers class ends with a hard assfucking - Finn Harding , Amanda Riley”

Trashreality 1 year ago

Sissy Crossdresser Training

Sissy Crossdresser Training

getTranny 1 month ago

FUI PRESENTE DE ANIVERSARIO DA BIANCA FERRAZ E AS TRANS ME DEVORARAM

FUI PRESENTE DE ANIVERSARIO DA BIANCA FERRAZ E AS TRANS ME DEVORARAM

XVideosRed 3 years ago

teen sissy in flat cage busts her balls until she cums

63% 4K 0:13 / 6:37

teen sissy in flat cage busts her balls until she cums

Clips4sale 6 months ago

Self Sucking Facial

63% HD 2:00 / 8:19

Self Sucking Facial

Flirt4Free 5 years ago

SUBMISSIVE LADYBOY FIRST ANAL CASTING &amp_ SLAVE TRAINING

Premium HD 33:42

SUBMISSIVE LADYBOY FIRST ANAL CASTING &amp_ SLAVE TRAINING

xnxxGold 1 week ago

Brihana Boll Private Show

HD 2:00 / 26:42

Brihana Boll Private Show

Flirt4Free 2 months ago

Brutus Shows Off His Big Cock

HD 2:00 / 11:18

Brutus Shows Off His Big Cock

Flirt4Free 8 years ago

Messy Sissy Cream Enema & Banana Strapon Ride

Messy Sissy Cream Enema & Banana Strapon Ride

xHamster 7 months ago

Futa Anal Training - Stronger by the day. (Sample)

Futa Anal Training - Stronger by the day. (Sample)

Eporner 1 year ago

I'll cum on you !! prostate orgasm

I'll cum on you !! prostate orgasm

Pornzona 1 month ago

Noa's training Day 2 19's Japanese student squirts for the first time with a sex toy.

Noa's training Day 2 19's Japanese student squirts for the first time with a sex toy.

xHamster 1 year ago

Ava Venom and Giselle Driller Double Dom and Fuck Submissive Masculine Bottom Colby Jensen

53% 0:30 / 33:07

Ava Venom and Giselle Driller Double Dom and Fuck Submissive Masculine Bottom Colby Jensen

Clips4sale 9 months ago

FUCK ASS, HOLE PLAY AND SUKING HOLE - Part 2

FUCK ASS, HOLE PLAY AND SUKING HOLE - Part 2

Flirt4Free 1 week ago

Andrea & Taty Private Show

HD 2:00 / 13:00

Andrea & Taty Private Show

Flirt4Free 3 months ago

Aleex & Paulo Private Show

55% HD 2:00 / 17:52

Aleex & Paulo Private Show

Flirt4Free 10 months ago

Boucning On Fat Daddy: Bee Sits And Bounces on Her 4 Inch Thick Cock!

Boucning On Fat Daddy: Bee Sits And Bounces on Her 4 Inch Thick Cock!

xHamster 1 month ago

Emiliano Dante Private Show

4K 2:00 / 49:02

Emiliano Dante Private Show

Flirt4Free 3 weeks ago

Spandex Sissy Lady Domina Rectal Machine

Spandex Sissy Lady Domina Rectal Machine

TrannyGem 3 years ago

Hungry Crossdresser Ass Gets a Hard Dick

Hungry Crossdresser Ass Gets a Hard Dick

xHamster 1 month ago

sexy oiled big dick tgirl cums from bad dragon tentacle anal

64% 4K 0:15 / 8:45

sexy oiled big dick tgirl cums from bad dragon tentacle anal

Clips4sale 11 months ago

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