Training Videos - Trans (124,542)

Russian Beautiful girl Anastasia Mistress fucking a slave with strapon anal submission sissy amateur homemade

Russian Beautiful girl Anastasia Mistress fucking a slave with strapon anal submission sissy amateur homemade

XHamster 5 months ago

Treat Me Like a Sissy-slut

50% HD 1:01 / 18:39

Treat Me Like a Sissy-slut

FapHouse 10 months ago

Resident Sissy 8-bit Parody Sissification Transformation

Resident Sissy 8-bit Parody Sissification Transformation

ShemaleSin 3 months ago

sissypov - mature sissy kati finnish swallowed all his cum

sissypov - mature sissy kati finnish swallowed all his cum

TransDoe 3 years ago

Sissy with Girly Body in High Heels

63% HD 0:39 / 6:46

Sissy with Girly Body in High Heels

FapHouse 2 years ago

Anal make me Squirt in chastity

Anal make me Squirt in chastity

XHamster 8 months ago

Trying New Fist Dildo and Get Fucked and Fisted

Trying New Fist Dildo and Get Fucked and Fisted

XHamster 1 year ago

Two Mistresses Humiliate a Sissy, Making Him Sniff and Lick Their Socks, Pegging His Asspussy and Fucking His Throat

Two Mistresses Humiliate a Sissy, Making Him Sniff and Lick Their Socks, Pegging His Asspussy and Fucking His Throat

FapHouse 6 days ago

Skinny Submissive Ladyboy Self Anal Fisting and Slave Training

Skinny Submissive Ladyboy Self Anal Fisting and Slave Training

FapHouse 1 year ago

Dimitry Rolex & Liliith Private Show

Dimitry Rolex & Liliith Private Show

Camster 2 years ago

Not All About Beauty

Not All About Beauty

Some.Porn 2 years ago

Taniax masturbate in the streets with big black dildo wearing sexy miniskirt

Taniax masturbate in the streets with big black dildo wearing sexy miniskirt

XHamster 1 month ago

Alexxa Ivanova Private Show

HD 2:00 / 22:17

Alexxa Ivanova Private Show

Flirt4Free 3 years ago

Luke Hardy & Cristian Ford Private Show

4K 2:00 / 19:32

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 year ago

Sexy striptease, savage twerk naked, fingering and more ;)

Sexy striptease, savage twerk naked, fingering and more ;)

Flirt4Free 5 years ago

TS Gray Perrier Rides a Huge Dildo Stretching Out Her Tight Ass

TS Gray Perrier Rides a Huge Dildo Stretching Out Her Tight Ass

XHamster 3 months ago

Trans girl lift weights with her cock

Trans girl lift weights with her cock

XHamster 5 months ago

$Sex and Cum in Elias\' Mouth$ 58% HD 2:00 / 35:38

Sex and Cum in Elias\' Mouth

Flirt4Free 1 year ago

I'm gonna turn you into my little bitch and fuck your throat raw with my big, throbbing cock - FEMINIZATION ROLEPLAY - AI

I'm gonna turn you into my little bitch and fuck your throat raw with my big, throbbing cock - FEMINIZATION ROLEPLAY - AI

XHamster 1 year ago

Ass to mouth sissy training

73% HD 0:26 / 21:21

Ass to mouth sissy training

QueensOfKink 1 year ago

Crossdresser Bailey Wilde Pegged by Woman

Crossdresser Bailey Wilde Pegged by Woman

XHamster 2 months ago

Coach Peeper Lends A Hand

Coach Peeper Lends A Hand

Some.Porn 9 months ago

sissy slave to bbc

sissy slave to bbc

Pornwhite 2 years ago

Sissy Maid All Plugged with Huge Dildo

Sissy Maid All Plugged with Huge Dildo

XHamster 1 month ago

Bride Cumshot by Anal Fuck

Bride Cumshot by Anal Fuck

XHamster 1 month ago

Sissy Training by Queen Daralis Part 3

Sissy Training by Queen Daralis Part 3

XHamster 7 months ago

Being a Girl Is More Fun - 4K MP4

4K 0:17 / 10:29

Being a Girl Is More Fun - 4K MP4

Clips4sale 1 year ago

A Rather Unusual Doctor Examines Me with Inannajustice

62% HD 1:01 / 19:32

A Rather Unusual Doctor Examines Me with Inannajustice

FapHouse 8 months ago

Relent to Your Trans Mistress

Relent to Your Trans Mistress

XHamster 5 months ago

Long Intense Anal Machine Fuck with Black Fist, Crossdresser Bi Guy

Long Intense Anal Machine Fuck with Black Fist, Crossdresser Bi Guy

FapHouse 2 years ago

Just Outta Curiosity

65% HD 0:10 / 3:17

Just Outta Curiosity

LoyalFans 3 years ago

Extreme Anal Objects Sissy Slut!

Extreme Anal Objects Sissy Slut!

FapHouse 2 years ago

sexy oiled big dick tgirl cums from bad dragon tentacle anal

65% 4K 0:15 / 8:45

sexy oiled big dick tgirl cums from bad dragon tentacle anal

Clips4sale 1 year ago

Monster Mega butt plug. larissa1sexdoll sexy trans. Extreme insertions. Unique ass piercings.

Monster Mega butt plug. larissa1sexdoll sexy trans. Extreme insertions. Unique ass piercings.

XHamster 2 years ago

Mama Studio introduces "Training my step nephew to lick a trans for the first-ever time" - Free-for-all

Mama Studio introduces "Training my step nephew to lick a trans for the first-ever time" - Free-for-all

TrannyGem 5 months ago

Jailbird Gives His Mouth to Blonde Shemale Prison Guard and Ass to Strap-pn of Assistant District Attorney

Jailbird Gives His Mouth to Blonde Shemale Prison Guard and Ass to Strap-pn of Assistant District Attorney

XHamster 3 months ago

TS Isa Oliveira destroys Hex with extreme deep throat and merciless face fucking (720p ENG-sub) Trans Woman - Trans Cock Sucker - Trans Blowjob - Trans Domination

HD 0:31 / 14:25

TS Isa Oliveira destroys Hex with extreme deep throat and merciless face fucking (720p ENG-sub) Trans Woman - Trans Cock Sucker - Trans Blowjob - Trans Domination

Clips4sale 3 months ago

JOI CEI ANAL - BE MY BEST SISSY WITH YOUR BEST HEELS AND FUCK YOUR ASS WITH A DILDO

JOI CEI ANAL - BE MY BEST SISSY WITH YOUR BEST HEELS AND FUCK YOUR ASS WITH A DILDO

XHamster 5 months ago

Sophia Loreen Party on Jul 30, 2026 - Part 3

57% 4K 2:00 / 42:41

Sophia Loreen Party on Jul 30, 2026 - Part 3

Camster 1 month ago

Petra,s 8th training

Petra,s 8th training

XHamster 1 year ago

Human Ashtray for Mistress Lilith

60% HD 1:01 / 41:36

Human Ashtray for Mistress Lilith

FapHouse 7 months ago

Leashed Good Girl Takes the Strap

Leashed Good Girl Takes the Strap

FapHouse 1 month ago

A 11-inch BBC Dildo On The Sex Machine Fucks Hot Trannys Anal

A 11-inch BBC Dildo On The Sex Machine Fucks Hot Trannys Anal

XHamster 3 years ago

Hot Trans Girl Tutor Trains You

Hot Trans Girl Tutor Trains You

FapHouse 1 year ago

DP Fetish Fun

HD 0:39 / 13:12

FapHouse 6 years ago

$I will show you how wild I can get, let me scream and moan in your ear while you fuck me hard. Don\'t miss this show !!!$ HD 2:00 / 4:52

I will show you how wild I can get, let me scream and moan in your ear while you fuck me hard. Don\'t miss this show !!!

Flirt4Free 4 years ago

Trans in Bondage Having Anal Training by a Dominatrix

Trans in Bondage Having Anal Training by a Dominatrix

FapHouse 5 months ago

teen sissy in flat cage busts her balls until she cums

69% 4K 0:13 / 6:37

teen sissy in flat cage busts her balls until she cums

Clips4sale 11 months ago

Psychic Predicts He Will Become a Woman

Psychic Predicts He Will Become a Woman

XHamster 2 months ago

POINT OF VIEW-Trans gf attempts to get him to stop dinking around with her girlfriend- inhale-job and plumbed

POINT OF VIEW-Trans gf attempts to get him to stop dinking around with her girlfriend- inhale-job and plumbed

Transvids.tv 1 year ago

Lots of Encouragement

HD 2:00 / 13:56

Lots of Encouragement

Camster 4 years ago

Sabina & Caine Private Show

HD 2:00 / 11:28

Sabina & Caine Private Show

Flirt4Free 3 years ago

Urinating compilation plane purity cell.

Urinating compilation plane purity cell.

TrannyGem 2 years ago

Sophia Loreen Party on Aug 21, 2026 - Part 5

65% 4K 2:00 / 2:22:08

Sophia Loreen Party on Aug 21, 2026 - Part 5

Camster 1 month ago

Sissy Strained to Suck Mistress's Strap-on Before Getting Fucked Hard

Sissy Strained to Suck Mistress's Strap-on Before Getting Fucked Hard

XHamster 1 year ago

Cute face Trans in Elasticgirl Cosplay Humiliating Herself with Anal Creampie Farts after Fucking her Ass with Dildo

Cute face Trans in Elasticgirl Cosplay Humiliating Herself with Anal Creampie Farts after Fucking her Ass with Dildo

XHamster 2 weeks ago

Independent Training No81 Tucking And Anal Exposure Walk on the Riverside Part 2

Independent Training No81 Tucking And Anal Exposure Walk on the Riverside Part 2

XHamster 8 months ago

Just Outta Curiosity

58% HD 0:10 / 3:17

Just Outta Curiosity

LoyalFans 3 years ago

Alisa Fresh Private Show

50% 4K 2:00 / 25:19

Alisa Fresh Private Show

Flirt4Free 2 months ago

Ryley Rails Dominates You

61% HD 1:01 / 13:17

Ryley Rails Dominates You

FapHouse 11 months ago

Towing the Line Finale

54% HD 0:10 / 13:02

Towing the Line Finale

LoyalFans 4 years ago

Brandy gets exceedingly lewd and rides screw machine for greater quantity than twelve sissygasms

Brandy gets exceedingly lewd and rides screw machine for greater quantity than twelve sissygasms

ShemaleSin 8 months ago

Trix Bell Private Show

66% 4K 2:00 / 10:54

Trix Bell Private Show

Camster 1 year ago

Shemale Fucks Shemale Riding Dick Cowgirl

Shemale Fucks Shemale Riding Dick Cowgirl

XHamster 1 month ago

Aubrey Saint Private Show

Aubrey Saint Private Show

Camster 2 months ago

Domme Feminizes Then Fucks Sissy

Domme Feminizes Then Fucks Sissy

XHamster 2 months ago

Jose & Richard Private Show

55% HD 2:00 / 6:00

Jose & Richard Private Show

Flirt4Free 4 months ago

wife makes you her MTF sissy slut camwhore & lesbian lover - full video on Veggiebabyy Manyvids

wife makes you her MTF sissy slut camwhore & lesbian lover - full video on Veggiebabyy Manyvids

XHamster 2 years ago

”Sexy Shemale Venus Lux trains newcomer Javier LoveTongue with her raw dick”

”Sexy Shemale Venus Lux trains newcomer Javier LoveTongue with her raw dick”

IFuckedYourGF 9 months ago

Submissive Sissy Femboy Facefucked & Feminized Hard in Sleazy Motel - Bigdaddy8inchz

Submissive Sissy Femboy Facefucked & Feminized Hard in Sleazy Motel - Bigdaddy8inchz

XHamster 7 months ago

Alessia Viilla & Charlie Lenox Private Show

Alessia Viilla & Charlie Lenox Private Show

Flirt4Free 1 year ago

Sissy Boi’s Tiny Cock Is Caged Whilst Spreading Their Ass Cheeks and Fucking Their Worthless Ass

67% HD 1:01 / 21:45

Sissy Boi’s Tiny Cock Is Caged Whilst Spreading Their Ass Cheeks and Fucking Their Worthless Ass

FapHouse 7 months ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Camster 2 weeks ago

Amber Mei Neil's sissy cock compilation - deep face hole, deepthroat, and face smashed!

Amber Mei Neil's sissy cock compilation - deep face hole, deepthroat, and face smashed!

TrannyMovs 1 week ago

Insatiable Sissy Melody Sluts Out with a Huge Dildo

Insatiable Sissy Melody Sluts Out with a Huge Dildo

XHamster 2 years ago

Big Ass Trans Raven Anal Gaped and Bred after Riding Bbc Fat Dildo

Big Ass Trans Raven Anal Gaped and Bred after Riding Bbc Fat Dildo

XHamster 7 months ago

ULTIMATE FOOT FETISH COMPILATION - Foot Worship, Footjobs, Smelly Socks, Femdom, Pornstars, Cum On Feet, Boot Worship

ULTIMATE FOOT FETISH COMPILATION - Foot Worship, Footjobs, Smelly Socks, Femdom, Pornstars, Cum On Feet, Boot Worship

ShemaleSin 5 months ago

Sissy Quiz

45% HD 0:18 / 24:11

IWantClips 3 years ago

Private Sissygasm Show

Private Sissygasm Show

XHamster 1 week ago

Neomie Thompson Private Show

58% 4K 2:00 / 34:21

Neomie Thompson Private Show

Flirt4Free 1 year ago

Jasmine Dlight - Shemale Sex Goddess Rides an Extra Long Dildo Deep

Jasmine Dlight - Shemale Sex Goddess Rides an Extra Long Dildo Deep

FapHouse 1 month ago

AB145 Pink packaging - The fallen chaste nun -Edging

AB145 Pink packaging - The fallen chaste nun -Edging

Lesbian8 2 months ago

sissypov - aliza breeze sissy slut loves dick

sissypov - aliza breeze sissy slut loves dick

TransDoe 2 years ago

Atakan Ali Private Show

60% HD 2:00 / 6:07

Atakan Ali Private Show

Flirt4Free 1 year ago

Get railed fucking hard by your futanari girlfriend (Dildo JOI)

Get railed fucking hard by your futanari girlfriend (Dildo JOI)

XHamster 3 months ago

Ball Games/ Stretch/ Nipples Play/ Dick Sucking

4K 2:00 / 29:12

Ball Games/ Stretch/ Nipples Play/ Dick Sucking

Flirt4Free 7 months ago

Special training for anal masturbation! Transgender In search of a new comfort.

Special training for anal masturbation! Transgender In search of a new comfort.

XHamster 11 months ago

Marian & Richard Private Show

Marian & Richard Private Show

Flirt4Free 5 days ago

SPECIAL: Fat ass Femboy Cumfarting Anal Creampie after being Gaped and Fucked by Black Dildo

SPECIAL: Fat ass Femboy Cumfarting Anal Creampie after being Gaped and Fucked by Black Dildo

XHamster 4 months ago

This tranny is so cute, she urgently needs a thick cock in her ass

This tranny is so cute, she urgently needs a thick cock in her ass

XGroovy 2 years ago

Sissy gasm time

Sissy gasm time

XHamster 7 months ago

Extraordinary Sissy Bad Dragon Gaping and FemDom Gap Destruction with Speculum Show Off by Mistresse Mercer

Extraordinary Sissy Bad Dragon Gaping and FemDom Gap Destruction with Speculum Show Off by Mistresse Mercer

ShemaleSin 10 months ago

Sissy Maddy is a very naughty gurl who loves big toys in her ass

Sissy Maddy is a very naughty gurl who loves big toys in her ass

XHamster 10 months ago

Asian Beauty in College Uniform Squirts While Training Her Anal by Pushing a Huge Anal Plug Out

68% HD 0:39 / 7:47

Asian Beauty in College Uniform Squirts While Training Her Anal by Pushing a Huge Anal Plug Out

FapHouse 7 months ago

TS Nadia Love dominated by Goddess Tangent

70% HD 0:39 / 41:49

TS Nadia Love dominated by Goddess Tangent

FapHouse 5 years ago

whore cum from my bbc!!!

whore cum from my bbc!!!

PornBox 1 year ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 1 day ago

Taboo CBT Confession

43% HD 1:01 / 19:48

Taboo CBT Confession

FapHouse 3 years ago

Taking Your Ass fucking Viginity ft Trans Femdominance

Taking Your Ass fucking Viginity ft Trans Femdominance

TransTube.tv 2 years ago

Futa Step-Mom Feminizes You

62% 4K 0:28 / 25:42

Futa Step-Mom Feminizes You

Clips4sale 1 year ago

feminisation training

feminisation training

ShemaleSin 8 months ago

Mistress streches urethra peehole of her sissy with dilator edging

Mistress streches urethra peehole of her sissy with dilator edging

XHamster 8 months ago

Mistress Mercer's Sissy Anal Fisting Training

Mistress Mercer's Sissy Anal Fisting Training

BallsAndBoobs 2 months ago

Japanese mistress trains and punishes house slave who is excited by the Mistress's laundry by making him wear women's underwear

Japanese mistress trains and punishes house slave who is excited by the Mistress's laundry by making him wear women's underwear

XHamster 10 months ago

Clit Fucking My Trans Girlfriend in the Ass

Clit Fucking My Trans Girlfriend in the Ass

XHamster 1 month ago

She Trains Her Sissy Friend to Receive Cocks

She Trains Her Sissy Friend to Receive Cocks

FapHouse 1 year ago

ANAL FUCK Tranny Skeletor Ass Licking SPUNK SWALLOWER AssHole Banged by Nasty Pervert Penis!

ANAL FUCK Tranny Skeletor Ass Licking SPUNK SWALLOWER AssHole Banged by Nasty Pervert Penis!

XHamster 3 years ago

Weekly anal stretch training part 2 with nipple scene at the end

Weekly anal stretch training part 2 with nipple scene at the end

XHamster 2 years ago

Luke Hardy & Cristian Ford Private Show

4K 2:00 / 27:54

Luke Hardy & Cristian Ford Private Show

Flirt4Free 3 months ago

Blonde Sissy Bride Rubs Her New Pussy Chastity

Blonde Sissy Bride Rubs Her New Pussy Chastity

XHamster 3 months ago

Sissy Cow Maddy Loves Tasting Her Own Ass

Sissy Cow Maddy Loves Tasting Her Own Ass

XHamster 7 months ago

Multiformity begins her Bad Dragon training with Mistresse Miguire

Multiformity begins her Bad Dragon training with Mistresse Miguire

Amateur8 1 year ago

Fake Boobs Jaquelin Braxton Trains The Gym Rat With Her Cock

Fake Boobs Jaquelin Braxton Trains The Gym Rat With Her Cock

BeMyHole 4 years ago

BBC MAKING WHITE BOYS EXTINCT

47% HD 0:10 / 7:09

BBC MAKING WHITE BOYS EXTINCT

LoyalFans 3 years ago

Humiliation 280

HD 0:25 / 17:27

Humiliation 280

Clips4sale 1 week ago

Scots Sissy Sluts Makeup Part 1

Scots Sissy Sluts Makeup Part 1

Clips4sale 4 years ago

Sissy Slut For Goddess Mandy

62% HD 0:29 / 13:36

Sissy Slut For Goddess Mandy

Clips4sale 2 years ago

Corporate Teaching

Corporate Teaching

Transvids.tv 1 year ago

Shemale Brandy Loves Anal with Jason Follow Along with Us

Shemale Brandy Loves Anal with Jason Follow Along with Us

XHamster 2 years ago

BE ASHAMED FAGGOT

61% HD 0:10 / 11:26

BE ASHAMED FAGGOT

LoyalFans 3 years ago

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