Training Videos - Trans (119,576)

Beg for his big cock like a good sissy boy

Beg for his big cock like a good sissy boy

XHamster 11 years ago

Mistress Mercer Extreme Deepthroat Strap-on Oral Cock Training for Sissy Chastity Slut

Mistress Mercer Extreme Deepthroat Strap-on Oral Cock Training for Sissy Chastity Slut

YouPorn Unknown

kilu

TrannyGem 2 years 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

TS Eva Joi Loves Being a Submissive Slut for Ria Bentley

TS Eva Joi Loves Being a Submissive Slut for Ria Bentley

XVideos 2 years ago

Acceptance o and sissy transformation of Femme Sandy

Acceptance o and sissy transformation of Femme Sandy

XHamster 3 years ago

Transsexual training - bukkake gokkun! Shemale anal fuck orgy 4

Transsexual training - bukkake gokkun! Shemale anal fuck orgy 4

PornFreeNow 1 year ago

Crossdresser slut in yellow fishnet green miniskirt and black corsage opens his hole with big toys nipple pumps, chastity

Crossdresser slut in yellow fishnet green miniskirt and black corsage opens his hole with big toys nipple pumps, chastity

XHamster 2 years ago

Step Mommy's Little Panty Boy: Teaching My Sissy Boy - Sissification & Panty Fetish Domina Andrea Rosu MOBILE

4K 0:20 / 12:03

Step Mommy's Little Panty Boy: Teaching My Sissy Boy - Sissification & Panty Fetish Domina Andrea Rosu MOBILE

Clips4sale 1 year ago

Zariah Aura, Jade Venus And Lottie Lovelace In Lesbian In Training

Zariah Aura, Jade Venus And Lottie Lovelace In Lesbian In Training

Xshemale 3 weeks ago

Sophia Loreen Private Show

65% HD 2:00 / 22:54

Sophia Loreen Private Show

Camster 3 weeks ago

Marianna & Ian Private Show

Marianna & Ian Private Show

Flirt4Free 2 years ago

Alejandra Fox Private Show

67% HD 2:00 / 13:37

Alejandra Fox Private Show

Flirt4Free 10 months ago

Chastity Sissy Rides Giant Black Dildo - Anal Sissygasm and Vibegasm Cumswallow

Chastity Sissy Rides Giant Black Dildo - Anal Sissygasm and Vibegasm Cumswallow

XVideos 1 month ago

Goddess Lohan - Gluttonous Slut Gets Picked Up the Ass - HD

HD 0:29 / 15:08

Goddess Lohan - Gluttonous Slut Gets Picked Up the Ass - HD

Clips4sale 3 years ago

Blonde Femdom Futa Girl Filling Her Submissive Boy With Cum

Blonde Femdom Futa Girl Filling Her Submissive Boy With Cum

BoyFriendTV 2 months ago

ryu Doll letting her machine do the work

ryu Doll letting her machine do the work

Pornzona 2 weeks ago

Alejandra Fox Private Show

HD 2:00 / 14:02

Alejandra Fox Private Show

Flirt4Free 2 years ago

Peter Zaynus Private Show

Peter Zaynus Private Show

Flirt4Free 4 years ago

Ahri Star Sneaks in BBC Training

Ahri Star Sneaks in BBC Training

XVideos 9 years ago

Sissy Kanisa Waiting for Her Client at a Hotel Room Ep1: Black Pantyhose Try on

Sissy Kanisa Waiting for Her Client at a Hotel Room Ep1: Black Pantyhose Try on

FapHouse 1 week ago

you were meant to be a girl: loving feminization and pov bj - SD

you were meant to be a girl: loving feminization and pov bj - SD

Clips4sale 1 year ago

Tammy Frizz Private Show

HD 2:00 / 15:19

Tammy Frizz Private Show

Flirt4Free 2 weeks ago

Alanna Barker Private Show

Alanna Barker Private Show

Camster 1 year ago

Petite Trans Kawaii Fiona Fucks a Submissive Trans Puppy-Girl

Petite Trans Kawaii Fiona Fucks a Submissive Trans Puppy-Girl

Lesbian8 1 year ago

Imperious Blk Trans w/ 11 inch inches BIG BLACK COCK Hellion Dallas Vixen Managing The Bi-Otches

Imperious Blk Trans w/ 11 inch inches BIG BLACK COCK Hellion Dallas Vixen Managing The Bi-Otches

TrannyGem 3 years ago

Spank that sissy ass! 👋

Premium HD 4:37

Spank that sissy ass! 👋

Sheer 1 year ago

FUCK MACINE AND PINK MINI SKIRT

FUCK MACINE AND PINK MINI SKIRT

XHamster 4 years ago

You Never Fuck a Woman! Just a Sexy Pillow! Lol!!! JOI for Real Losers! German

53% HD 1:01 / 9:15

You Never Fuck a Woman! Just a Sexy Pillow! Lol!!! JOI for Real Losers! German

FapHouse 5 months ago

I Fuck Lola Ass!!!

HD 0:39 / 11:02

I Fuck Lola Ass!!!

FapHouse 2 weeks ago

Blonde shemale ass fucked after training

Blonde shemale ass fucked after training

AShemaleTube 9 years ago

Rubber Female Mask Crossdresser Gets Fucked by Strap-on in Midair! Anal Fisting!

65% HD 0:11 / 36:30

Rubber Female Mask Crossdresser Gets Fucked by Strap-on in Midair! Anal Fisting!

Clips4sale 4 years 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 9 months ago

Senpai Trains TS Doxy

Senpai Trains TS Doxy

ShemaleSin 4 years ago

Making You Soft Forever

HD 0:29 / 19:00

Making You Soft Forever

Clips4sale 10 months ago

Join for watch me Squirt!! - Part 3

Join for watch me Squirt!! - Part 3

Camster 4 weeks ago

Leyla Steel Private Show

56% 4K 2:00 / 12:27

Leyla Steel Private Show

Flirt4Free 1 year ago

Cowgirl Ride on Your D... Pillow!

Cowgirl Ride on Your D... Pillow!

Flirt4Free 1 year ago

Cristel Halvorsen Private Show

Cristel Halvorsen Private Show

Flirt4Free 3 years ago

TS Juliana Belfort catches Hex in her lingerie and turns him into her sissy slut (720p ENG-sub) Trans Woman - Trans Fucking - Trans Blowjob - Trans Cock Sucker

HD 0:29 / 31:51

TS Juliana Belfort catches Hex in her lingerie and turns him into her sissy slut (720p ENG-sub) Trans Woman - Trans Fucking - Trans Blowjob - Trans Cock Sucker

Clips4sale 1 month ago

VR sissy training part 1 (close up cock dripping all over you)

VR sissy training part 1 (close up cock dripping all over you)

RedTube Unknown

Sniff My Latex Arse & Pussy Ball Kicking CBT, Scent Fetish & Human Furniture Degradation

Sniff My Latex Arse & Pussy Ball Kicking CBT, Scent Fetish & Human Furniture Degradation

FapHouse 1 week ago

Addonis Smith & Huber Nicols Private Show

62% HD 2:00 / 11:18

Addonis Smith & Huber Nicols Private Show

Flirt4Free 2 years ago

Latina petite trans stepsister destroyed her tight pink little trap for your big dick

Latina petite trans stepsister destroyed her tight pink little trap for your big dick

JuicyTrans 1 month ago

MULTI CUMSHOTS PRIVAT ORDER

MULTI CUMSHOTS PRIVAT ORDER

XVideos 1 year ago

Lad catboy deep throats fucktoy and imagines it humping his face

Lad catboy deep throats fucktoy and imagines it humping his face

TransTube.tv 2 years ago

Fap off with crimson Boinks an a Ample blast of jism

Fap off with crimson Boinks an a Ample blast of jism

TrannyGem 1 year ago

My Femboy Roommate - 18 Year Old Femboy Wakes Me up with a Sloppy Blowjob

My Femboy Roommate - 18 Year Old Femboy Wakes Me up with a Sloppy Blowjob

XHamster 7 months ago

Prisoner Kanisa Get Punishment From Officer Wei and Officer Reina

67% 1:01 / 26:20

Prisoner Kanisa Get Punishment From Officer Wei and Officer Reina

FapHouse 1 year ago

Nastya Blue Private Show

HD 2:00 / 43:00

Nastya Blue Private Show

Camster 2 years ago

Anna Summerss Private Show

Anna Summerss Private Show

Camster 4 years ago

Unfathomable Strokes With Mr Hankeys Centaur Sex toy

Unfathomable Strokes With Mr Hankeys Centaur Sex toy

ShemaleSin 1 year ago

Sissy Elvi Lynx BBC Long Dildo Fuck Machine and Self Facial

HD 0:39 / 23:28

Sissy Elvi Lynx BBC Long Dildo Fuck Machine and Self Facial

FapHouse 2 weeks 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

Sarada Training v2.2 Part 5 Big Boobs Size By LoveSkySan69

Sarada Training v2.2 Part 5 Big Boobs Size By LoveSkySan69

Pornzona 3 months ago

Trans Girl Fingering Size Training

Trans Girl Fingering Size Training

FapHouse 2 weeks ago

Ftm Soldier Receives Humiliating Pussy Discipline Training

60% HD 0:30 / 15:06

Ftm Soldier Receives Humiliating Pussy Discipline Training

Clips4sale 2 years ago

Hot ebony Ameena Green doing her workout on a sexy latina trannys huge dick

Hot ebony Ameena Green doing her workout on a sexy latina trannys huge dick

Yeswegays 1 month ago

Nastya Blue Private Show

HD 2:00 / 13:04

Nastya Blue Private Show

Camster 2 years ago

Valery & Felipe Private Show

HD 2:00 / 13:47

Valery & Felipe Private Show

Flirt4Free 2 years ago

SUBMISSIVE LADYBOY FIRST ANAL CASTING & SLAVE TRAINING

Premium HD 33:41

SUBMISSIVE LADYBOY FIRST ANAL CASTING & SLAVE TRAINING

Sheer 3 months ago

Balls and Bat in My Stretched Ass, Anal Gape and Huge Cumshot

HD 1:01 / 15:07

Balls and Bat in My Stretched Ass, Anal Gape and Huge Cumshot

FapHouse 1 day ago

Yuli Maid is pounded by her dominatrix jade

Yuli Maid is pounded by her dominatrix jade

TrannyGem 3 years ago

Secret Sissy Winter Challenge

Secret Sissy Winter Challenge

IWantClips 1 year ago

Exhibitionist Domme & Humiliated Sub: Queen Elena Flashes, Then Gags & Walks Sissy Femme Sandy

44% 0:39 / 5:38

Exhibitionist Domme & Humiliated Sub: Queen Elena Flashes, Then Gags & Walks Sissy Femme Sandy

FapHouse 5 months ago

Femdom Spit Roast: TS Crystal Bellini & Mistress Alexis Kim Destroy Tanner Tatum

HD 0:30 / 12:57

Femdom Spit Roast: TS Crystal Bellini & Mistress Alexis Kim Destroy Tanner Tatum

Clips4sale 2 months ago

Drag Queen Obsession

57% HD 1:01 / 9:22

Drag Queen Obsession

FapHouse 1 year ago

Fuck Us Both Billy

59% HD 0:39 / 26:20

Fuck Us Both Billy

FapHouse 10 months ago

Author Learning to Take Black Cock Hands Free - Real Life Training

Author Learning to Take Black Cock Hands Free - Real Life Training

FapHouse 1 week ago

Bonnie Boombelle Party on Jun 26, 2026 - Part 2

66% 4K 2:00 / 18:40

Bonnie Boombelle Party on Jun 26, 2026 - Part 2

Camster 3 weeks ago

Deep Anal Training sissy slut

Deep Anal Training sissy slut

XHamster 1 year ago

Shemale nurse Victora Grant already knows the training with the doctor will lead to sex.The busty

Shemale nurse Victora Grant already knows the training with the doctor will lead to sex.The busty

AShemaleTube 1 week ago

Fetish Therapist Domme Eva Spandex Cougar Rectal Transgender Princess Superslut Yanny Trump Transgender Dark Haired BONDAGE & DISCIPLINE Fucktoy

Fetish Therapist Domme Eva Spandex Cougar Rectal Transgender Princess Superslut Yanny Trump Transgender Dark Haired BONDAGE & DISCIPLINE Fucktoy

TrannyGem 3 years ago

Get rid of your cock - The Lady of Feminisation gives you sissy cunt a nice cameltoe panty

Get rid of your cock - The Lady of Feminisation gives you sissy cunt a nice cameltoe panty

XHamster 2 years ago

Desire Sweet Private Show

Desire Sweet Private Show

Camster 3 weeks ago

SISSY training to CUM and ORGASM

SISSY training to CUM and ORGASM

XVideos 1 year ago

Addonis Smith & Huber Nicols Private Show

68% HD 2:00 / 8:56

Addonis Smith & Huber Nicols Private Show

Flirt4Free 2 years ago

I Love BBC! Fuck My Asspussy Deep and Rough!

I Love BBC! Fuck My Asspussy Deep and Rough!

XHamster 3 months ago

$[Trans] T-Girl Latex$ 66% VR 1:27 / 43:15

[Trans] T-Girl Latex

VrSmash 2 months ago

Valery & Felipe Private Show

Valery & Felipe Private Show

Flirt4Free 2 years ago

Anna Summerss Private Show

HD 2:00 / 1:01:58

Anna Summerss Private Show

Flirt4Free 4 years ago

Exhibit Sissy Caught with Dancing Dildo Outdoors Tries to Seduce

Exhibit Sissy Caught with Dancing Dildo Outdoors Tries to Seduce

FapHouse 1 year ago

Fucking His Ass Whenever She Wants

Fucking His Ass Whenever She Wants

XHamster 6 months ago

21yo Femboy Viii penalized

21yo Femboy Viii penalized

Transvids.tv 1 year ago

Sissy Crossdresser Anal Fisting and Fucked by Huge Dildo

71% HD 1:01 / 13:52

Sissy Crossdresser Anal Fisting and Fucked by Huge Dildo

FapHouse 1 year ago

Transformation in Pink - Lady Angela giving her sissy a makeover with sissy training and made to crossdress

Transformation in Pink - Lady Angela giving her sissy a makeover with sissy training and made to crossdress

Clips4sale 1 year ago

SAY “I AM A FAGGOT MISTRESS RAVEN”

68% HD 0:10 / 23:45

SAY “I AM A FAGGOT MISTRESS RAVEN”

LoyalFans 3 years ago

Two Sissies Captured for Lady Sara Borgia's Sissy School (1080p)

HD 0:15 / 11:37

Two Sissies Captured for Lady Sara Borgia's Sissy School (1080p)

Clips4sale 2 weeks ago

Black Goddess's Strap-On Seduction SISSY TRAINING ASMR JOI

Black Goddess's Strap-On Seduction SISSY TRAINING ASMR JOI

Pornzona 2 weeks ago

Luciana Sainz Private Show

Luciana Sainz Private Show

Flirt4Free 4 months ago

Anna Summerss Private Show

HD 2:00 / 15:28

Anna Summerss Private Show

Flirt4Free 4 years ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 4 years ago

Teaching to Jizm in My Virginity Box, I Dont Get To Yet =

Teaching to Jizm in My Virginity Box, I Dont Get To Yet =

Gayhub 1 week ago

transexjapan allison anal training

transexjapan allison anal training

PornOne 1 year ago

Pissing in Chastity Cage

61% HD 0:39 / 5:40

Pissing in Chastity Cage

FapHouse 1 year ago

As Black Mamba coaches Nick Ryder in weight training, the Latin stud gets horny and lures Mamba with a kiss.

As Black Mamba coaches Nick Ryder in weight training, the Latin stud gets horny and lures Mamba with a kiss.

Some.Porn 1 year ago

Unexperienced Sissy breezy fellate that big black cock and got butt total rock hard poked

Unexperienced Sissy breezy fellate that big black cock and got butt total rock hard poked

Gayhub 1 year ago

Sounding and Prostate Exam - Medical Fisting Extreme Anal Shemale Fetish Nurse Exam Fetish

56% HD 0:39 / 11:52

Sounding and Prostate Exam - Medical Fisting Extreme Anal Shemale Fetish Nurse Exam Fetish

FapHouse 1 year ago

Riding a Fat Dildo and Masturbating a Cock

Riding a Fat Dildo and Masturbating a Cock

FapHouse 1 year ago

Sophia Loreen Private Show

HD 2:00 / 15:34

Sophia Loreen Private Show

Flirt4Free 1 week ago

Bondage Slut Training With Gabriela Belt

Bondage Slut Training With Gabriela Belt

WinPorn 6 months ago

Compilation Sissy Public Dildo Assfuck

Compilation Sissy Public Dildo Assfuck

XHamster 2 weeks ago

Megan Sexsymbol Slut Training With Blowjob

Megan Sexsymbol Slut Training With Blowjob

Nuvid 5 months ago

How About a 35 Minute Video with Fucking - Sucking and Lots of Hot Sexy Fun? Starring Bailey Love - Lexi and Riley. the Training

63% HD 0:39 / 35:10

How About a 35 Minute Video with Fucking - Sucking and Lots of Hot Sexy Fun? Starring Bailey Love - Lexi and Riley. the Training

FapHouse 1 year ago

Alicia Akbar Private Show

Alicia Akbar Private Show

Flirt4Free 3 years ago

Bound TV Maid Tested (MP4)

Bound TV Maid Tested (MP4)

Clips4sale 2 years 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 1 week ago

Soaking Wet Pussy

Soaking Wet Pussy

Flirt4Free 10 years ago

Jerking on the Railroad

Jerking on the Railroad

FapHouse 1 week ago

Close-up going knuckle deep... Master's arm is swallowed by the enlarged puss... White love juice overflows...

Close-up going knuckle deep... Master's arm is swallowed by the enlarged puss... White love juice overflows...

TransTube.tv 1 year ago

Alexxa A Private Show

Alexxa A Private Show

Flirt4Free 7 months 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 1 year ago

Alanna Barker Private Show

Alanna Barker Private Show

Flirt4Free 1 year ago

Sissy Slave Watches World Cup Hours of Sucking Dick, Licking Balls and Eating Ass, While Being Degraded

Sissy Slave Watches World Cup Hours of Sucking Dick, Licking Balls and Eating Ass, While Being Degraded

FapHouse 6 days ago

AB121 Lustful succubus extreme training

AB121 Lustful succubus extreme training

YouPorn Unknown

Sissy training stewardess hard CUM

Sissy training stewardess hard CUM

XVideos 5 years ago

Anal Training Sissy Asspussy Masturbation Sissygasm Big Dildo Anal gape Crossdresser Femboy Tranny

Anal Training Sissy Asspussy Masturbation Sissygasm Big Dildo Anal gape Crossdresser Femboy Tranny

YouPorn Unknown

Twink cosplayer gets raw ass pounded while moaning loud in tight chastity

Twink cosplayer gets raw ass pounded while moaning loud in tight chastity

GayPornWatch 1 week ago

Sissy Shower Series - Red Satin and Mesh Ouvert Lingerie Set

Sissy Shower Series - Red Satin and Mesh Ouvert Lingerie Set

XVideos 2 years ago

Sophia Loreen Private Show

65% HD 2:00 / 18:40

Sophia Loreen Private Show

Camster 1 week ago

65 66 67 68 69

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