Training Videos - Trans (124,024)

Each one loathes u whiteboi, even your headmistress Roxy abhors u sissy for BNWO girl scarlett ebony

Each one loathes u whiteboi, even your headmistress Roxy abhors u sissy for BNWO girl scarlett ebony

ShemaleSin 4 years ago

SPECIFIC: Sissy Anal Stretching Training with Multiple Dildos and Giant Creampie

SPECIFIC: Sissy Anal Stretching Training with Multiple Dildos and Giant Creampie

ShemaleSin 8 months ago

Ts Diana Deelight sucking on and bouncing on a big black dick compilation

HD 0:39 / 12:21

Ts Diana Deelight sucking on and bouncing on a big black dick compilation

FapHouse 1 month ago

Huge ebony dick worship anal/bj trainer for submissive CD sluts (no captions)

Huge ebony dick worship anal/bj trainer for submissive CD sluts (no captions)

XXXShemalePorn 5 years ago

SisK being fucked by fucking machine

SisK being fucked by fucking machine

XHamster 4 years ago

Your ABDL Babysitter Has a Futa Cock! | Penny Barber

Your ABDL Babysitter Has a Futa Cock! | Penny Barber

Fapcat 4 years ago

Wielded Sissy cockslut flows & ravages herself moist while Cheating female dominance queen is away! 4/5 Utter flick briefly

Wielded Sissy cockslut flows & ravages herself moist while Cheating female dominance queen is away! 4/5 Utter flick briefly

TrannyGem 1 year ago

Trampling subdued incel

Trampling subdued incel

Some.Porn 11 months ago

Red Satin and Hot Cock Sucking and Masturbating with a Cloth at Step-auntie Lady Victoria Valente

Red Satin and Hot Cock Sucking and Masturbating with a Cloth at Step-auntie Lady Victoria Valente

XHamster 5 months ago

Padrona italiana femminilizza e svergina il culo di uno schiavo

Padrona italiana femminilizza e svergina il culo di uno schiavo

ShemaleSin 3 months ago

Bimbo Bitch Transformation Mesmerizing Femdom Audio & Spirals by Tara Smith

Bimbo Bitch Transformation Mesmerizing Femdom Audio & Spirals by Tara Smith

SortPorn 3 weeks ago

fodendo a gostosa da luiza devil na cachoeira em taubate

fodendo a gostosa da luiza devil na cachoeira em taubate

PornBox 8 months ago

Bisexual Foursome Two Sissy and Two Dominant Princesses

Bisexual Foursome Two Sissy and Two Dominant Princesses

XHamster 2 years ago

Anabel Fiofilova Private Show

Anabel Fiofilova Private Show

Camster 1 month ago

Aleex & Paulo Private Show

52% HD 2:00 / 9:50

Aleex & Paulo Private Show

Flirt4Free 1 year 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

I Changed Out of My Wet and See-through Training Clothes Again.

I Changed Out of My Wet and See-through Training Clothes Again.

XHamster 1 year ago

lexi sindel trains her gimp

lexi sindel trains her gimp

AbTranny 7 years ago

Pulsating Asshole During Orgasm - Sissy Training PT 1

Pulsating Asshole During Orgasm - Sissy Training PT 1

XHamster 4 years ago

Bondage Tit Slapping: Playwithkk's Expert Nipple Pinch Exam

Bondage Tit Slapping: Playwithkk's Expert Nipple Pinch Exam

FapHouse 1 month ago

RUINED TWICE!!! Post Orgasm Handjob

RUINED TWICE!!! Post Orgasm Handjob

Tranny.one 4 years ago

THE TRAINING OF MY TS SERF ANGEL

THE TRAINING OF MY TS SERF ANGEL

ShemaleSin 5 years ago

Breasty Trans Maid Gets Her Booty and Titties Drilled by Hung Housewife

Breasty Trans Maid Gets Her Booty and Titties Drilled by Hung Housewife

ShemaleSin 1 year ago

SUBMISSIVE LADYBOY FIRST ANAL CASTING &amp_ SLAVE TRAINING

Premium HD 33:42

SUBMISSIVE LADYBOY FIRST ANAL CASTING &amp_ SLAVE TRAINING

XNXXGold 5 months ago

Screwing Faggot

Screwing Faggot

ShemaleSin 5 years ago

Sissy Veronica Vincent & Mistress Wife Eva Knieva Discuss Their Latest Date Night

Sissy Veronica Vincent & Mistress Wife Eva Knieva Discuss Their Latest Date Night

XHamster 4 months ago

Aromatic shemale paradise - Task

Aromatic shemale paradise - Task

Clips4sale 3 years ago

Nvh-029 Transsexual Bondage Training Lesbian Female Te

Nvh-029 Transsexual Bondage Training Lesbian Female Te

Xshemale 1 month ago

Hot Trans Girl Tutor Trains You

55% HD 1:01 / 41:53

Hot Trans Girl Tutor Trains You

FapHouse 1 year ago

My New Best Toy

61% HD 1:01 / 21:22

My New Best Toy

FapHouse 1 year ago

Corporate Training Futanari Porn Video

Corporate Training Futanari Porn Video

AniPorn 2 years ago

Petra 1e training

Petra 1e training

ShemaleSin 1 year ago

”Big dick gimp anal fucks trainee”

”Big dick gimp anal fucks trainee”

TransHero 9 months ago

Hot Petite Jamie Markham Gets Anal Workout

69% HD 1:01 / 23:20

Hot Petite Jamie Markham Gets Anal Workout

FapHouse 3 years ago

Sissy Anal Training Session

Sissy Anal Training Session

FapHouse 2 weeks ago

Submission training session for sweet brunette shemale

Submission training session for sweet brunette shemale

PornLib 3 years ago

hottest pulverizing machine fuck-fest ever

hottest pulverizing machine fuck-fest ever

TrannyGem 2 years ago

[ASMR] Positive Sissy Reinforcement - Audio Only

41% HD 0:30 / 12:03

[ASMR] Positive Sissy Reinforcement - Audio Only

Clips4sale 1 year ago

A super-sexy fun time

A super-sexy fun time

TransTube.tv 2 years ago

The Sissy slut getting fisted and double too - Part 1

61% 4K 0:30 / 8:22

The Sissy slut getting fisted and double too - Part 1

Clips4sale 2 years ago

Femboy Gape Compilation #2 fart-gapes

58% HD 1:01 / 6:11

Femboy Gape Compilation #2 fart-gapes

FapHouse 8 months ago

Sissy Charlotte learns to deepthroat large penis

Sissy Charlotte learns to deepthroat large penis

Amateur8 4 years ago

Redhead Trans Blake Sucks Cute Little Schlong of Her Sissy Partner Liam in An Open Public Resturant and Caught by Owner

Redhead Trans Blake Sucks Cute Little Schlong of Her Sissy Partner Liam in An Open Public Resturant and Caught by Owner

Dafreeporn 3 weeks ago

Cupcake Journey

35% HD 0:10 / 8:56

Cupcake Journey

LoyalFans 2 years ago

TRAINING THOSE MAN-MEAT HUNGRY FUCK-HOLES

TRAINING THOSE MAN-MEAT HUNGRY FUCK-HOLES

TransTube.tv 2 years ago

Jasmine_dlight - Glamazon Giantess in Pvc Low Angle POV Sub Slut Training Vr180

Jasmine_dlight - Glamazon Giantess in Pvc Low Angle POV Sub Slut Training Vr180

FapHouse 1 month ago

Transgirl in Chastity Humps Her Pillows

Transgirl in Chastity Humps Her Pillows

Tranny.one 4 months ago

Anal beads training 🖤⚫⚫⚫⚫

Anal beads training 🖤⚫⚫⚫⚫

AShemaleTube 1 year ago

becoming femme - mandi cum laude how deep would you go into a ts just the tip or all the way porn video

becoming femme - mandi cum laude how deep would you go into a ts just the tip or all the way porn video

TransDoe 1 year ago

Amber Burnt Private Show

Amber Burnt Private Show

Camster 2 years ago

Your sissy hole can handle how many BBCs humiliation training

Your sissy hole can handle how many BBCs humiliation training

AveXXX 2 weeks ago

Milky Bois merely! Sissy Trainer! WARNING Y

Milky Bois merely! Sissy Trainer! WARNING Y

TrannyGem 6 years ago

Long intense anal machine fuck with black fist, crossdresser bi guy

Long intense anal machine fuck with black fist, crossdresser bi guy

XHamster 2 years ago

Sissy FUCKED Protection-free-for-all by Dark-hued Parent from Grindr - CD MIKAH GIRL with BIG BLACK COCK

Sissy FUCKED Protection-free-for-all by Dark-hued Parent from Grindr - CD MIKAH GIRL with BIG BLACK COCK

TransTube.tv 1 year ago

Being a sissy butt slut 3

Being a sissy butt slut 3

XHamster 2 months ago

Crossdresser Gapes His Man Pussy with a Huge Dildo

Crossdresser Gapes His Man Pussy with a Huge Dildo

GayVids 1 month ago

Jay Is Fisting TS Sissy CD Anal

Jay Is Fisting TS Sissy CD Anal

FapHouse 1 year ago

Sissy Tries Booty To Throat For The 1st Time And Love It

Sissy Tries Booty To Throat For The 1st Time And Love It

ShemaleSin 2 months ago

”Yoga Lesbian Girls Judge Each Other's Ass”

”Yoga Lesbian Girls Judge Each Other's Ass”

TransHero 9 months ago

HOTWIFE CUCKOLDS YOU MIND FUCK - Erotic Cuckold Training [Cuckold] [Cuck] [Cuckoldry] [Cuckolding] [BDSM] [Hotwife] [Wife] [Bull]

HOTWIFE CUCKOLDS YOU MIND FUCK - Erotic Cuckold Training [Cuckold] [Cuck] [Cuckoldry] [Cuckolding] [BDSM] [Hotwife] [Wife] [Bull]

Clips4sale 1 year ago

S043 - Anal with Big Dildo 8

66% HD 1:01 / 16:08

S043 - Anal with Big Dildo 8

FapHouse 1 year ago

Good Boy Takes Cock From Hot Dominatrix

Good Boy Takes Cock From Hot Dominatrix

XHamster 2 weeks ago

Playing with my ass with an anal toy

Playing with my ass with an anal toy

XHamster 6 months ago

Ass-fucked and loving it

Ass-fucked and loving it

Some.Porn 1 year ago

Independent training No22 Exposure walk along the road at dusk

Independent training No22 Exposure walk along the road at dusk

XHamster 9 months ago

Sissy Lesson: Panties Make You Cum

HD 0:30 / 13:27

Sissy Lesson: Panties Make You Cum

Clips4sale 4 months ago

Full Sissy Ball Emptying out of Stimulation and Giant Jizz Flow

Full Sissy Ball Emptying out of Stimulation and Giant Jizz Flow

ShemaleSin 5 years ago

Tranny Larissa TS Trains Her Ass on Dildos Before Taking Cock

Tranny Larissa TS Trains Her Ass on Dildos Before Taking Cock

AShemaleTube 1 month ago

Sissy takes biggest sex tool on screw machine

Sissy takes biggest sex tool on screw machine

ShemaleSin 3 years ago

Triple Femdom Spin The Bottle

Triple Femdom Spin The Bottle

Clips4sale 1 year ago

”Daisy chain of fucking awesomeness”

”Daisy chain of fucking awesomeness”

ThePornstar 2 years ago

Трахаю рукой и кабачком свою sissy шлюху. После чего она лижет жопу и пьет мочу со своей спермой

Трахаю рукой и кабачком свою sissy шлюху. После чего она лижет жопу и пьет мочу со своей спермой

TransTube.tv 1 year ago

pawg training for big black-cock winter olympics

pawg training for big black-cock winter olympics

PornBox 2 years ago

German goddess and thrall crossdresser in SADOMASOCHISM session

German goddess and thrall crossdresser in SADOMASOCHISM session

MatureTubeHere 3 years ago

Confused sissy boys transformed by big black cock feminization trainer (bbc) with captions

Confused sissy boys transformed by big black cock feminization trainer (bbc) with captions

XXXShemalePorn 1 year ago

Troy Khalil Private Show

69% HD 2:00 / 18:38

Troy Khalil Private Show

Flirt4Free 2 years ago

Anal training and pumping in Nicolly Summers' hungry ass.

Anal training and pumping in Nicolly Summers' hungry ass.

AShemaleTube 2 weeks ago

CUM MY UNFATHOMABLE GAP!

CUM MY UNFATHOMABLE GAP!

ShemaleSin 1 year ago

Independent Training No20 Exposure Walk with a chastity belt

Independent Training No20 Exposure Walk with a chastity belt

ShemaleSex 6 months ago

AB085 Lustful Abby Kitty be Master's sissy slave -chastity (Chinese and English subtitles)

AB085 Lustful Abby Kitty be Master's sissy slave -chastity (Chinese and English subtitles)

XHamster 2 years ago

Lady Fyre's School for Boys and Good Sissies

Lady Fyre's School for Boys and Good Sissies

XHamster 2 years ago

Sophia Loreen Private Show

61% 4K 2:00 / 12:04

Sophia Loreen Private Show

Flirt4Free 1 month ago

Sissygasm & Leaking BIG BLACK COCK

Sissygasm & Leaking BIG BLACK COCK

TrannyGem 1 year ago

Bad Dragon Pounding and Gaping - original early web camera show by Mistresse Mercer

Bad Dragon Pounding and Gaping - original early web camera show by Mistresse Mercer

Amateur8 9 months ago

Instructional Sissy Slut Training On How To Find and SuckMore Guys

65% 4K 0:27 / 21:54

Instructional Sissy Slut Training On How To Find and SuckMore Guys

Clips4sale 1 year ago

Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 8

Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 8

XHamster 1 month ago

River Enza dominates and punishes her sissy with hardcore rough sex and face cumshots

River Enza dominates and punishes her sissy with hardcore rough sex and face cumshots

TrannyMovs 3 months ago

Pornstar Lessons

Pornstar Lessons

Some.Porn 1 year ago

Juanita Swan Private Show

61% HD 2:00 / 5:31

Juanita Swan Private Show

Flirt4Free 3 years ago

Edging JOI Ryley Rails

68% HD 0:39 / 5:27

Edging JOI Ryley Rails

FapHouse 9 months ago

T-girl football bitch! After training, it's time for a fellatio!

T-girl football bitch! After training, it's time for a fellatio!

BigTitsLust 2 months ago

Sissy Club Slut: Femdom Fisting, Pegging, Dick Sticking Part 2 of 2 (1080p)

60% HD 0:22 / 29:58

Sissy Club Slut: Femdom Fisting, Pegging, Dick Sticking Part 2 of 2 (1080p)

Clips4sale 2 years ago

THE TRAINING OF MY TS SLAVEGIRL *HD 1080*

63% HD 0:10 / 19:19

THE TRAINING OF MY TS SLAVEGIRL *HD 1080*

LoyalFans 2 years ago

My Butt Is Made for Anal and Creampies

63% HD 0:39 / 22:24

My Butt Is Made for Anal and Creampies

FapHouse 2 years ago

Gay Task for Sissy Goon – Bisexual Encouragement by Goddess Nikki Kit

61% HD 0:25 / 8:27

Gay Task for Sissy Goon – Bisexual Encouragement by Goddess Nikki Kit

IWantClips 1 year ago

Do You Like to See a Shredded and Muscular Body ?

43% HD 2:00 / 13:57

Do You Like to See a Shredded and Muscular Body ?

Flirt4Free 4 years ago

White Sissy Virginity Instructing (Smash Machine)

White Sissy Virginity Instructing (Smash Machine)

TrannyGem 10 months ago

Truth or Dare

61% HD 0:11 / 38:27

Clips4sale 4 years ago

Corrine Dittmann Private Show

Corrine Dittmann Private Show

Flirt4Free 3 months ago

becomingfemme - natty is queen of the sissy university

becomingfemme - natty is queen of the sissy university

TransDoe 2 years ago

Emily Adaire gets a helping hand to stretch her rectal hole - Trailer

Emily Adaire gets a helping hand to stretch her rectal hole - Trailer

ShemaleSin 4 years ago

Milking My Rubber Slut (1080p)

66% HD 0:01 / 10:02

Milking My Rubber Slut (1080p)

Clips4sale 5 years ago

Marily Daniela Private Show

63% HD 2:00 / 13:47

Marily Daniela Private Show

Flirt4Free 2 years ago

secretary caught jerking off

66% HD 0:10 / 39:44

secretary caught jerking off

Clips4sale 3 years ago

Just my deep Belly Bulge training

Just my deep Belly Bulge training

XHamster 2 years ago

DOMINATION & SUBMISSION Sissy inhale training with enema!

DOMINATION & SUBMISSION Sissy inhale training with enema!

TransTube.tv 1 year ago

Two Sexy Trannies And One Plum Buxom Gal Go Wild In the Locker Room After the Training

Two Sexy Trannies And One Plum Buxom Gal Go Wild In the Locker Room After the Training

XCafe 2 years ago

Threesome Slut Training Sharing with BF Part 2

61% HD 0:39 / 7:15

Threesome Slut Training Sharing with BF Part 2

FapHouse 10 months ago

Step-Daddy Kyaa's Dick

56% HD 0:10 / 10:58

Step-Daddy Kyaa's Dick

LoyalFans 2 years ago

This Sissy Tgirl Will Get Her Ass Strap-on and Fuck

60% HD 1:01 / 27:11

This Sissy Tgirl Will Get Her Ass Strap-on and Fuck

FapHouse 9 months ago

Sophia Loreen Party on May 30, 2026 - Part 3

61% HD 2:00 / 1:08:30

Sophia Loreen Party on May 30, 2026 - Part 3

Camster 3 months ago

Feminization : Your new Life as a Sissy Slave - Transformation - Ep4 I Turn a Compulsive Wanker into a Slave - Maitresse Julia

Feminization : Your new Life as a Sissy Slave - Transformation - Ep4 I Turn a Compulsive Wanker into a Slave - Maitresse Julia

XHamster 2 years ago

Handcuffed Chastity Sissy Thrall takes Super-Sized Sextoy and FemDom Latex Fisting by Mistresse Mercer

Handcuffed Chastity Sissy Thrall takes Super-Sized Sextoy and FemDom Latex Fisting by Mistresse Mercer

ShemaleSin 9 months ago

Feminization Positivity Trainer

Feminization Positivity Trainer

Fapcat 4 years ago

Naughty Japanese Student Gives a Hot Blowjob With Sweet Skill

Naughty Japanese Student Gives a Hot Blowjob With Sweet Skill

Some.Porn 1 month ago

She-Cock Cuckold Wedding Desecration

HD 0:30 / 12:21

She-Cock Cuckold Wedding Desecration

Clips4sale 3 months ago

Teen ladyboy strips off and sits her shaved anal on sex toy

Teen ladyboy strips off and sits her shaved anal on sex toy

XXXShemalePorn 9 years ago

After Basketball Training We Had a Quick Fuck During Shower

After Basketball Training We Had a Quick Fuck During Shower

XHamster 4 weeks ago

BLACK TGIRLS - Tools of Temptation Vixen Coxx & Papi

BLACK TGIRLS - Tools of Temptation Vixen Coxx & Papi

XHamster 1 year ago

Hot slutwife training .!. I'll teach you to be submissive, my sweet mature bitch.!.

Hot slutwife training .!. I'll teach you to be submissive, my sweet mature bitch.!.

XHamster 2 years ago

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