Training Videos - Trans (124,050)

@VonMadeHaNut “ Crossdresser White Construction Worker ”

@VonMadeHaNut “ Crossdresser White Construction Worker ”

2BGay 3 years ago

Sissy Teaching - Sissygasm Encouragement Jessica Bloom

Sissy Teaching - Sissygasm Encouragement Jessica Bloom

TrannyGem 4 years ago

Femdom Real Couple female domination pegging & ding-knob mastix & sissy cuck feminization FULL movie scene

Femdom Real Couple female domination pegging & ding-knob mastix & sissy cuck feminization FULL movie scene

Dafreeporn 2 years ago

Rah Teach

TrannyGem 5 years ago

Sissy Maid Strap-on Day

63% HD 0:39 / 9:53

Sissy Maid Strap-on Day

FapHouse 4 weeks ago

SISSY CLINICAL TRANSFORMATION MESMERIZE, Becoming A Sissy Femboy By A Domme Nurse - Sissy Training, Sissy Slut Mind Fuck

62% 0:30 / 24:08

SISSY CLINICAL TRANSFORMATION MESMERIZE, Becoming A Sissy Femboy By A Domme Nurse - Sissy Training, Sissy Slut Mind Fuck

Clips4sale 1 year ago

Threesome with Salome Salvi and Tantaly Sex Doll

Threesome with Salome Salvi and Tantaly Sex Doll

XHamster 3 months ago

Training a Twink Femboy Noisy Ass with BBC

63% HD 0:39 / 27:06

Training a Twink Femboy Noisy Ass with BBC

FapHouse 2 months ago

Seduced into anal and encouraged to clean up her cum load ft Hung TS Aleah Cuban

61% 0:29 / 27:12

Seduced into anal and encouraged to clean up her cum load ft Hung TS Aleah Cuban

Clips4sale 1 year ago

Getting Ready with Sissy Maid Candy!

Getting Ready with Sissy Maid Candy!

XHamster 5 months ago

Swallow My Loads Sissy Trainer

69% HD 0:39 / 10:58

Swallow My Loads Sissy Trainer

FapHouse 4 months ago

I Gave My Trans Girlfriend a Lot of Oral Sex After Training and She Came.

I Gave My Trans Girlfriend a Lot of Oral Sex After Training and She Came.

XHamster 6 months ago

Anal Training 84

57% HD 1:01 / 47:34

Anal Training 84

FapHouse 8 months ago

Sissy Slut Training 3

Sissy Slut Training 3

XHamster 1 year ago

Femdom POV: Blowing Smoke and Humiliating My Cuck Ex Ep 1

57% HD 0:39 / 8:39

Femdom POV: Blowing Smoke and Humiliating My Cuck Ex Ep 1

FapHouse 6 months ago

Trans Cuck Femdom Training

72% HD 1:01 / 20:58

Trans Cuck Femdom Training

FapHouse 7 months ago

Backyard Lesbian Deep-throat Training

56% HD 1:01 / 8:31

Backyard Lesbian Deep-throat Training

FapHouse 1 month ago

Archie Blossom Private Show

69% HD 2:00 / 11:08

Archie Blossom Private Show

Flirt4Free 6 months ago

Sophia Loreen Party on Apr 21, 2026 - Part 3

65% HD 2:00 / 40:40

Sophia Loreen Party on Apr 21, 2026 - Part 3

Flirt4Free 5 months ago

Merciless Hotel Throatfuck Marathon

60% HD 1:01 / 12:35

Merciless Hotel Throatfuck Marathon

FapHouse 3 months ago

Sissy Slut Pegged by 4 Asian Dommes

56% 0:39 / 11:57

Sissy Slut Pegged by 4 Asian Dommes

FapHouse 3 weeks ago

Sissy Boy Humiliation POV

50% HD 1:01 / 15:23

Sissy Boy Humiliation POV

FapHouse 5 months ago

Mike Swift & David Golden Private Show

51% HD 2:00 / 6:49

Mike Swift & David Golden Private Show

Flirt4Free 4 weeks ago

Pegging bitch of Princess Nicole

80% HD 1:01 / 18:36

Pegging bitch of Princess Nicole

FapHouse 6 years ago

Making My Cock Explode

63% HD 0:39 / 8:10

Making My Cock Explode

FapHouse 11 months ago

Femdom latex handling incel

Femdom latex handling incel

Some.Porn 1 year ago

TS Sissy CD Fisting in Black Pumps

72% HD 0:39 / 2:05

TS Sissy CD Fisting in Black Pumps

FapHouse 1 year ago

Sissy Blaire_18 in chastity belt. Dominatrix Nika plays with his balls with a vibrator. Feminized man in pink skirt

Sissy Blaire_18 in chastity belt. Dominatrix Nika plays with his balls with a vibrator. Feminized man in pink skirt

XHamster 1 year ago

Humiliation, strap-on and deep fisting

Humiliation, strap-on and deep fisting

XHamster 7 months ago

Crossdressing fucked in the butt

Crossdressing fucked in the butt

MyTransfix 3 months ago

Cutie Trans Hucow Melody Teaches Us How to Milk a Cock with Your Butt

61% HD 0:39 / 26:52

Cutie Trans Hucow Melody Teaches Us How to Milk a Cock with Your Butt

FapHouse 2 years ago

Corrine Dittmann Private Show

64% 4K 2:00 / 4:51

Corrine Dittmann Private Show

Camster 3 months ago

The Penalty for Theft

The Penalty for Theft

XHamster 1 week ago

get on your knees sissy

get on your knees sissy

Transvids.tv 1 year ago

Gym Tips for Sluts Feminization Motivation

63% HD 1:01 / 11:57

Gym Tips for Sluts Feminization Motivation

FapHouse 11 months ago

Desire Sweet Private Show

68% HD 2:00 / 5:44

Desire Sweet Private Show

Flirt4Free 3 weeks ago

Sph Mistress & Master Latin Big Cocks

50% HD 1:01 / 21:15

Sph Mistress & Master Latin Big Cocks

FapHouse 1 year ago

Flip Fuck with TS Kendall Penny

Flip Fuck with TS Kendall Penny

XHamster 1 month ago

Turning My Boyfriend Into A Sissy

Turning My Boyfriend Into A Sissy

XHamster 3 months ago

Ladyboy Alice with the Big Dick Gets Anal Training.

55% HD 0:39 / 44:38

Ladyboy Alice with the Big Dick Gets Anal Training.

FapHouse 1 week ago

Matt & Oliver & Andres Private Show

66% HD 2:00 / 4:56

Matt & Oliver & Andres Private Show

Flirt4Free 3 years ago

Imagine You Are Fucking a Boy!

Imagine You Are Fucking a Boy!

XHamster 10 months ago

Suck Jessica Bloom's Trans Cock - Large Buttplug Training + Swallow My Load Then Your Own CEI

Suck Jessica Bloom's Trans Cock - Large Buttplug Training + Swallow My Load Then Your Own CEI

XHamster 5 months ago

Sophia Loreen Private Show

71% 4K 2:00 / 14:01

Sophia Loreen Private Show

Flirt4Free 1 month ago

Backyard Lesbian Deep-throat Training

61% HD 0:39 / 8:31

Backyard Lesbian Deep-throat Training

FapHouse 1 month ago

Black Monster Dildo in My Ass, Grey Knee Socks, Black Thong and Big Cock

56% HD 1:01 / 10:04

Black Monster Dildo in My Ass, Grey Knee Socks, Black Thong and Big Cock

FapHouse 5 months ago

Trans Stepdoughter Caught in the Shower - No Orgasm Allowed - Hand Over Mouth Black Glove Fetish and Sissy Cunt Fucking Deep

Trans Stepdoughter Caught in the Shower - No Orgasm Allowed - Hand Over Mouth Black Glove Fetish and Sissy Cunt Fucking Deep

XHamster 4 days ago

Harin in Japan! Horny Sissy in Short Training Pants Risky Anal Masturbated in a Japanese Hotel Toilet and About to Be Caught

51% HD 0:39 / 9:52

Harin in Japan! Horny Sissy in Short Training Pants Risky Anal Masturbated in a Japanese Hotel Toilet and About to Be Caught

FapHouse 11 months ago

Trans Bimbo Gray Perrier trained w BBC

HD 0:10 / 16:06

Trans Bimbo Gray Perrier trained w BBC

LoyalFans 3 days ago

Fist Fucked - My Poor Ass! Emily Adaire & Goth Delilah

78% HD 1:01 / 13:39

Fist Fucked - My Poor Ass! Emily Adaire & Goth Delilah

FapHouse 1 year ago

Can Barely Stand Anymore... My Legs Are Still Shaking After That

76% 0:39 / 6:20

Can Barely Stand Anymore... My Legs Are Still Shaking After That

FapHouse 6 months ago

mistress fetish transexual alekssandra submissive rubber slave anal bondage training! shemale fucks his straight tight ass!

84% HD 2:55 / 1:45:28

mistress fetish transexual alekssandra submissive rubber slave anal bondage training! shemale fucks his straight tight ass!

AnalVids 7 months ago

Oiled Big Ass Shemale Black Widow Breed Anal Creampie and Cumfarts After Fucking Herself with Big Dildo

Oiled Big Ass Shemale Black Widow Breed Anal Creampie and Cumfarts After Fucking Herself with Big Dildo

XHamster 3 months ago

Columbian Boys Wedgie War

56% HD 2:00 / 15:54

Columbian Boys Wedgie War

Flirt4Free 1 year ago

Whimper and Beg Obedience Training JOI

HD 1:01 / 10:25

Whimper and Beg Obedience Training JOI

FapHouse 2 weeks ago

Unexpected Anal Training with PAWG Shemale Stepmom(3D Futa Anime)

Unexpected Anal Training with PAWG Shemale Stepmom(3D Futa Anime)

InPorn 2 months ago

Kept by Jessica Blake Part 4

Kept by Jessica Blake Part 4

XHamster 7 months ago

Brides Hands-free BBC Cumshots

77% HD 0:39 / 4:53

Brides Hands-free BBC Cumshots

FapHouse 4 months ago

Bi Slaves Bareback - Blowjobs and Arse Fucking

Bi Slaves Bareback - Blowjobs and Arse Fucking

XHamster 8 months ago

squirt - Part 2

59% 4K 2:00 / 9:52

squirt - Part 2

Flirt4Free 1 year ago

Alisa Fresh Private Show

56% 4K 2:00 / 17:59

Alisa Fresh Private Show

Camster 2 months ago

Sissy Slut Sucks Cock for Huge Load of Cum Twice in a Row - Jessica Bloom

66% HD 0:39 / 23:39

Sissy Slut Sucks Cock for Huge Load of Cum Twice in a Row - Jessica Bloom

FapHouse 10 months ago

Dimitri Caruso Private Show

56% HD 2:00 / 8:54

Dimitri Caruso Private Show

Flirt4Free 5 years ago

Latino Boys They Know Very Well What They Have

66% HD 2:00 / 4:10

Latino Boys They Know Very Well What They Have

Flirt4Free 1 year ago

Reina Hanno Stretches Anal with Jelly Dildo and Cums

61% HD 1:01 / 24:49

Reina Hanno Stretches Anal with Jelly Dildo and Cums

FapHouse 8 months ago

Pina CD Sissy Needs a Real Cock

58% HD 1:01 / 8:54

Pina CD Sissy Needs a Real Cock

FapHouse 1 year ago

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

56% HD 0:39 / 31:09

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

FapHouse 5 months ago

Dare to Get a Little Closer.

Dare to Get a Little Closer.

Camster 2 months ago

Plugging my sweet hole before training . Slow motion

Plugging my sweet hole before training . Slow motion

XHamster 1 year ago

One Cock, Two Throats - the Ultimate Deepthroat Test

57% HD 1:01 / 5:20

One Cock, Two Throats - the Ultimate Deepthroat Test

FapHouse 1 year ago

Gay Joy CEI

38% HD 1:01 / 17:00

FapHouse 5 months ago

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

75% HD 0:39 / 27:11

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

FapHouse 10 months ago

submissive asian ladyboy first anal casting & slave training

66% 2:14 / 37:28

submissive asian ladyboy first anal casting & slave training

AnalVids 2 months ago

Our Newest Mtof Transformation with Feminization Training Is Lucii Duval. Watch Here as Lucii Actually Loses Her Oral Virginity

74% HD 0:39 / 10:12

Our Newest Mtof Transformation with Feminization Training Is Lucii Duval. Watch Here as Lucii Actually Loses Her Oral Virginity

FapHouse 1 year ago

Fucking, Flip Flop

46% 4K 2:00 / 25:04

Fucking, Flip Flop

Flirt4Free 7 months ago

Actual Training at the Sissy Institute

56% HD 0:39 / 27:04

Actual Training at the Sissy Institute

FapHouse 6 months ago

Sandy Nell Private Show

57% HD 2:00 / 35:23

Sandy Nell Private Show

Camster 4 years ago

She’s never had it like this before, his cock takes her over the top until her eyes roll, and this country bumpkin gets creampi

65% HD 1:01 / 1:00:37

She’s never had it like this before, his cock takes her over the top until her eyes roll, and this country bumpkin gets creampi

FapHouse 5 years ago

Bossy Maid Trains You to Suck Her Dick

Bossy Maid Trains You to Suck Her Dick

MyTransfix 2 months ago

Japanese trans star Julia Winston fucked hard

73% HD 1:01 / 25:05

Japanese trans star Julia Winston fucked hard

FapHouse 5 years ago

Obedient Tgirl Follows Orders

HD 0:39 / 18:11

Obedient Tgirl Follows Orders

FapHouse 5 months ago

The Reward for the Locked-up Sissy

63% HD 0:39 / 12:56

The Reward for the Locked-up Sissy

FapHouse 10 months ago

Shiri's First Gangbang: Gym Slut Takes 5

61% 1:01 / 36:13

Shiri's First Gangbang: Gym Slut Takes 5

FapHouse 5 years ago

Dungeon Bondage Trans Gets Anal Training

68% HD 1:01 / 16:32

Dungeon Bondage Trans Gets Anal Training

FapHouse 5 months ago

I came home from the gym sweaty, I came in my socks, licked all my cum and swallowed it all.

I came home from the gym sweaty, I came in my socks, licked all my cum and swallowed it all.

XHamster 2 years ago

Submitted and Shown off

Submitted and Shown off

XHamster 2 months ago

24-7 Slave for Tranny Girl - He Is Only Allowed to Watch Her and Lick Feet!

62% HD 1:01 / 23:31

24-7 Slave for Tranny Girl - He Is Only Allowed to Watch Her and Lick Feet!

FapHouse 7 months ago

Complimentary MILF Massage

Complimentary MILF Massage

Some.Porn 2 years ago

Agent Trains Her Replacement To Eat Good Pussy - A Thong-Slinging, Leather-loving Lesbian Adventure

Agent Trains Her Replacement To Eat Good Pussy - A Thong-Slinging, Leather-loving Lesbian Adventure

Some.Porn 2 years ago

Nyxi's 1st Week as Nyxi - Day 3 Lots of Fun Here in the 38 Minute Video.

80% HD 1:01 / 28:51

Nyxi's 1st Week as Nyxi - Day 3 Lots of Fun Here in the 38 Minute Video.

FapHouse 1 year ago

Edlin Dockray Private Show

66% HD 2:00 / 13:31

Edlin Dockray Private Show

Flirt4Free 2 years ago

submissive asian ladyboy slave training & anal fisting

70% 2:12 / 37:45

submissive asian ladyboy slave training & anal fisting

AnalVids 2 months ago

Lisan & Mine Private Show

Lisan & Mine Private Show

Flirt4Free 1 week ago

Christian & Lian Private Show

54% HD 2:00 / 5:42

Christian & Lian Private Show

Flirt4Free 3 years ago

Spitroasted in wondrous underwear by two big fake-jizz-shotguns

Spitroasted in wondrous underwear by two big fake-jizz-shotguns

TransTube.tv 1 year ago

becomingfemme - jeni justice trained and turned into a sexy sissy

becomingfemme - jeni justice trained and turned into a sexy sissy

TransDoe 3 years ago

Flip Fuck with TS Kendall Penny

65% HD 1:01 / 18:59

Flip Fuck with TS Kendall Penny

FapHouse 2 months ago

Breaking Her Sissy Doll (full 1 Hr 15 Min of Hardcore Femdom) Slut Exposed in Bondage & Chastity for Pegging, Fisting, and Mach

66% HD 1:01 / 1:13:02

Breaking Her Sissy Doll (full 1 Hr 15 Min of Hardcore Femdom) Slut Exposed in Bondage & Chastity for Pegging, Fisting, and Mach

FapHouse 1 week ago

Big Ass Transsexual Raven Huge Asshole Gape and Anal Creampie Breed with Alien Dildo After Mating Press

Big Ass Transsexual Raven Huge Asshole Gape and Anal Creampie Breed with Alien Dildo After Mating Press

XHamster 3 months ago

Having a Hard Time - Shemale Jane Foursome with Eve, Elizabeth & Anna

52% HD 1:01 / 25:05

Having a Hard Time - Shemale Jane Foursome with Eve, Elizabeth & Anna

FapHouse 1 month ago

Sophia Loreen Private Show

63% 4K 2:00 / 5:21

Sophia Loreen Private Show

Flirt4Free 2 weeks ago

Becoming Her

XHamster 4 months ago

Hana Rouse Private Show

46% 4K 2:00 / 24:45

Hana Rouse Private Show

Flirt4Free 10 months ago

Punished Slaves BDSM Bondage Gay Amador Big Dick 2

59% HD 0:39 / 7:13

Punished Slaves BDSM Bondage Gay Amador Big Dick 2

FapHouse 6 months ago

Zara Clark Private Show

58% 4K 2:00 / 6:41

Zara Clark Private Show

Flirt4Free 4 months ago

Glam Slut Milking Training 2

58% HD 1:01 / 20:26

Glam Slut Milking Training 2

FapHouse 8 months ago

Alexxa A Private Show

49% HD 2:00 / 23:23

Alexxa A Private Show

Camster 3 months ago

Trained and Dominated TV & TS

Trained and Dominated TV & TS

Tranny.one 4 years ago

Viky & Master Private Show

45% HD 2:00 / 9:05

Viky & Master Private Show

Flirt4Free 9 months ago

Brutus K Private Show

55% HD 2:00 / 6:01

Brutus K Private Show

Flirt4Free 10 years ago

Sissy Elvi Lynx Takes Turns Fucking Her Asshole and Her Throat with a Dildo

HD 1:01 / 12:55

Sissy Elvi Lynx Takes Turns Fucking Her Asshole and Her Throat with a Dildo

FapHouse 1 week ago

Threesome for My T Girl Friend, I Lend Her My 2 Favorite Big Spermy Cocks

59% 1:01 / 14:02

Threesome for My T Girl Friend, I Lend Her My 2 Favorite Big Spermy Cocks

FapHouse 2 years ago

Sophia Loreen Private Show

61% 4K 2:00 / 41:26

Sophia Loreen Private Show

Camster 1 month ago

Non stop PEGGING gives me 7x ANAL ORGASM, I rewarded with 1 for her SISSY dick

Non stop PEGGING gives me 7x ANAL ORGASM, I rewarded with 1 for her SISSY dick

XHamster 1 year ago

Casting of Anal Slave Nikita

56% HD 0:39 / 12:53

Casting of Anal Slave Nikita

FapHouse 9 months ago

”Maria Kazi Trains Her Anus For Huge Cock”

”Maria Kazi Trains Her Anus For Huge Cock”

TransHero 8 months ago

Depraved Sissy Gags on Cock, Cums on Cock, Eats Her Cum

HD 0:39 / 13:41

Depraved Sissy Gags on Cock, Cums on Cock, Eats Her Cum

FapHouse 6 days ago

The New Pet

XHamster 1 year ago

raw bareback tgirl big dick threesome live cam

raw bareback tgirl big dick threesome live cam

AnalVids 5 days ago

Suspended, Flogged & Caned by a Leather-clad Trans Domme

66% 0:39 / 18:17

Suspended, Flogged & Caned by a Leather-clad Trans Domme

FapHouse 1 month ago

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