Training Videos - Trans (116,950)

Lorens Valiant Private Show

Lorens Valiant Private Show

Flirt4Free 5 years ago

Basic training to become a sissy maid - Locked up and punished

Basic training to become a sissy maid - Locked up and punished

xHamster 4 months ago

Zara Clark Private Show

4K 2:00 / 10:36

Zara Clark Private Show

Flirt4Free 6 months ago

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

xHamster 1 year ago

Obedient Tgirl Follows Orders

63% HD 1:01 / 18:11

Obedient Tgirl Follows Orders

FapHouse 2 months ago

Latex Doll Ass Ripped Huge Dildo Gushing Sissy Cum Explosion

Latex Doll Ass Ripped Huge Dildo Gushing Sissy Cum Explosion

GayPornWatch 1 month ago

U Wish Tgirl Jock Bi Confusion

U Wish Tgirl Jock Bi Confusion

FreePorn8 4 years ago

Small Trans Kawaii Fiona Screws a Compliant Trans Puppy-Beauty

Small Trans Kawaii Fiona Screws a Compliant Trans Puppy-Beauty

ShemaleSin 1 year ago

Sissygasm

xHamster 1 year ago

Sissy Jessica Bloom Spitroast Training With Fucking Machine And Dildos - Anal Sissygasms and Cumswallow

Sissy Jessica Bloom Spitroast Training With Fucking Machine And Dildos - Anal Sissygasms and Cumswallow

xHamster 2 months ago

Instructions From the Trainer No. 25 Outdoor Anal Play 2

66% HD 0:39 / 11:17

Instructions From the Trainer No. 25 Outdoor Anal Play 2

FapHouse 5 months ago

Tarot Tales to Feminization

Tarot Tales to Feminization

xHamster 2 weeks ago

Asian twink sissy gets his tiny cock massaged by a cum-covered foot

Asian twink sissy gets his tiny cock massaged by a cum-covered foot

GayPornWatch 1 week ago

I fuck a transexual slut in the ass with my strap on dildo!

I fuck a transexual slut in the ass with my strap on dildo!

ShemaleSex 4 months ago

PetraTVsletje's 8th Training: A Hardcore Fisting, Anal, and a Huge Dildo Ride!

PetraTVsletje's 8th Training: A Hardcore Fisting, Anal, and a Huge Dildo Ride!

TrannyMovs 9 months ago

G065 - Chinese Princess Swallow Jerkoff

54% HD 0:39 / 9:26

G065 - Chinese Princess Swallow Jerkoff

FapHouse 1 year ago

Pecs Oil

Flirt4Free 9 years ago

Brandy trying to get caught crossdressing in public park

Brandy trying to get caught crossdressing in public park

ShemaleSin 9 months ago

XXL DILDO riding and XXL anal beads in doggy style

XXL DILDO riding and XXL anal beads in doggy style

xHamster 1 month ago

Consequences for Breaking Out of Chastity

HD 0:39 / 42:05

Consequences for Breaking Out of Chastity

FapHouse 1 month ago

SISSY TRAP - XXL RECTAL FAKE PENISES GAME

SISSY TRAP - XXL RECTAL FAKE PENISES GAME

TrannyGem 3 years ago

Blacked Big Ass Trans Samus Anal Creampie and Huge Cumfarts

Blacked Big Ass Trans Samus Anal Creampie and Huge Cumfarts

xHamster 5 months ago

Sissy Femboy

46% 1:01 / 5:47

FapHouse 2 years ago

Crossdresser Sissy Chastity Sex

Crossdresser Sissy Chastity Sex

FapHouse 1 month ago

MY GLORYHOLE CUM SLUT

50% HD 0:10 / 18:32

MY GLORYHOLE CUM SLUT

LoyalFans 3 years ago

Cute Tgirl Variety Itsol gets her big butt plugged & anal trained with a chastity cage

Cute Tgirl Variety Itsol gets her big butt plugged & anal trained with a chastity cage

TrannyMovs 9 months ago

I Am Going to Turn You Into a Goonette Ahegao Hucow - Asmr, Transformation, Hentai

56% HD 1:01 / 9:38

I Am Going to Turn You Into a Goonette Ahegao Hucow - Asmr, Transformation, Hentai

FapHouse 1 year ago

On Your Knees Cocksucker

On Your Knees Cocksucker

Pornzona 3 months ago

Nylon Sissy Slut Michelle Wakeup Training for the Show at Beijing Hotel

Nylon Sissy Slut Michelle Wakeup Training for the Show at Beijing Hotel

xHamster 1 year ago

Throating And Riding Monster Dildos Makes me Squirt Cum Sissy Jess Bloom

Throating And Riding Monster Dildos Makes me Squirt Cum Sissy Jess Bloom

ShemaleSin 3 months ago

The New Pet

xHamster 1 year ago

Step mom pulverizes son ass and train cum while being torn up

Step mom pulverizes son ass and train cum while being torn up

TransTube.tv 1 year ago

My First Serious Deepthroat Practice

My First Serious Deepthroat Practice

xHamster 3 weeks ago

Gorgeous T-girl Sluts Out with Huge Dildo Hard Anal, Gapes, Pushing Out Cum

HD 0:39 / 36:37

Gorgeous T-girl Sluts Out with Huge Dildo Hard Anal, Gapes, Pushing Out Cum

FapHouse 2 years ago

Bambi Sissy Transformation (Sissy Caption Story)

Bambi Sissy Transformation (Sissy Caption Story)

DeegX 3 years ago

Pink Sissy Maid Caught Dressing and Playing and Has a Sissygasm Riding Her Doll

65% HD 1:01 / 11:21

Pink Sissy Maid Caught Dressing and Playing and Has a Sissygasm Riding Her Doll

FapHouse 1 year ago

Master & Chris & Elvis Rey Private Show

63% HD 2:00 / 10:11

Master & Chris & Elvis Rey Private Show

Flirt4Free 3 years ago

Sissy acceptance: there's no going back

Sissy acceptance: there's no going back

Clips4sale 1 year ago

Claire Tenebrarum & Natalie Mars take turns training each other with toys

Claire Tenebrarum & Natalie Mars take turns training each other with toys

TrannyMovs 6 months ago

Cum twice while riding huge corn

Cum twice while riding huge corn

xHamster 6 months ago

Pushing It!!!

xHamster 2 years ago

SISSY SHAWNA IS A SLUTTY FAGGOT

69% HD 0:10 / 23:01

SISSY SHAWNA IS A SLUTTY FAGGOT

LoyalFans 3 years ago

Cum Factory Room 27

55% HD 1:01 / 13:12

Cum Factory Room 27

FapHouse 2 years ago

femboy fucked by latex mistress 😈

femboy fucked by latex mistress 😈

Pornzona 1 month ago

Taboo CBT Confession

54% HD 0:39 / 19:48

Taboo CBT Confession

FapHouse 2 years ago

Fat Ass Femboy Raven Asshole Gaped, Creampie and Cuming After Intense Anal Sex with BBC Dildo

44% HD 1:01 / 29:01

Fat Ass Femboy Raven Asshole Gaped, Creampie and Cuming After Intense Anal Sex with BBC Dildo

FapHouse 2 months ago

Black Domination and Verbal Attitude

45% HD 2:00 / 13:27

Black Domination and Verbal Attitude

Flirt4Free 1 year ago

Horny TS fucks gym prof while friend is watching

Horny TS fucks gym prof while friend is watching

Fapcat 2 years ago

Trans Domina Instructing her Fresh Encaged Sissy and her Cock-Squeezing Fuck-Holes

Trans Domina Instructing her Fresh Encaged Sissy and her Cock-Squeezing Fuck-Holes

TrannyGem 2 years ago

Stepdaughter Eden Espi Gets MASSIVE Trans Dick Throated and Fisted Anal

Stepdaughter Eden Espi Gets MASSIVE Trans Dick Throated and Fisted Anal

JuicyTrans 1 week ago

Christian & Nicco & Elvis Private Show

41% HD 2:00 / 19:28

Christian & Nicco & Elvis Private Show

Flirt4Free 2 years ago

Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm

Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm

xHamster 1 year ago

Cummunion - Amen, Motherfucker!

Cummunion - Amen, Motherfucker!

Clips4sale 6 months ago

4 Hot Guys Suck and Show Off

4 Hot Guys Suck and Show Off

Flirt4Free 8 years ago

Mommy wrecks her cock hungry FemBoy with HUGE fake TITS and massive trans dick

Mommy wrecks her cock hungry FemBoy with HUGE fake TITS and massive trans dick

JuicyTrans 2 weeks ago

Castrated Ladyboy PMV (Goon Mindlessly) [MOV Format]

62% 0:21 / 2:32

Castrated Ladyboy PMV (Goon Mindlessly) [MOV Format]

Clips4sale 1 month ago

Stefania Mafra Worships My Feet And Gags On Them (HD1080 MP4)

Stefania Mafra Worships My Feet And Gags On Them (HD1080 MP4)

Clips4sale 2 years ago

Sophia Loreen Party on May 30, 2026 - Part 3

HD 2:00 / 1:08:30

Sophia Loreen Party on May 30, 2026 - Part 3

Flirt4Free 3 weeks ago

Crossdresser Machine Fuck Training Anal Orgasm

Crossdresser Machine Fuck Training Anal Orgasm

FapHouse 2 years ago

European Model, Brutus Flexes

European Model, Brutus Flexes

Flirt4Free 10 years ago

Do you dare to Dance?:dancer:Let me catch you with my Sexy Moves Naked and Horny(fire)(sarcasm)(c)

45% HD 2:00 / 4:52

Do you dare to Dance?:dancer:Let me catch you with my Sexy Moves Naked and Horny(fire)(sarcasm)(c)

Flirt4Free 4 years ago

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

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

TransHero 3 years ago

I'll guide you to become the sissy you were meant to be (FEMINIZATION ROLEPLAY - AI GENERATED)

I'll guide you to become the sissy you were meant to be (FEMINIZATION ROLEPLAY - AI GENERATED)

xHamster 1 year ago

Three Femdom Cocks, One Fuck Doll Slut - Lesbian Anal Strap-On Gangbang ft Goddess Kyaa Raquel Roper XX, Mistress Tess & Miss Ardents - 1080p MP4

4K 0:10 / 11:13

Three Femdom Cocks, One Fuck Doll Slut - Lesbian Anal Strap-On Gangbang ft Goddess Kyaa Raquel Roper XX, Mistress Tess & Miss Ardents - 1080p MP4

Clips4sale 3 years ago

Captured feminized latexed & enslaved

40% HD 0:30 / 8:57

Captured feminized latexed & enslaved

Clips4sale 1 year ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 4 days ago

Sexy Video, My Favorite Erotic Outfit

Sexy Video, My Favorite Erotic Outfit

Flirt4Free 3 years ago

Bambi Blowjob Training Session #1

HD 0:17 / 10:07

Bambi Blowjob Training Session #1

Clips4sale 2 years ago

Cosplay slut Jenby Doll gets trained by Skye January (short version)

Cosplay slut Jenby Doll gets trained by Skye January (short version)

XVideos 3 years ago

Amateur Sissy hoe deep-throat that big black cock and got culo total rock-hard pummeled

Amateur Sissy hoe deep-throat that big black cock and got culo total rock-hard pummeled

4Gay 9 months ago

Sissy Purity Marionette Taunted and Abased by Domme, Denied and Locked in the Vice

Sissy Purity Marionette Taunted and Abased by Domme, Denied and Locked in the Vice

TrannyGem 5 years ago

Sissy Hope Anal Training Pt1

Sissy Hope Anal Training Pt1

ShemaleSin 1 year ago

Day 2 Tease and Denial

Day 2 Tease and Denial

xHamster 6 months ago

Beauties of Anal Delights for the Female Superiority Society (part 2).

Beauties of Anal Delights for the Female Superiority Society (part 2).

xHamster 1 year ago

Anal Training By Felicia POV

Anal Training By Felicia POV

IcePorn 2 weeks ago

Sph Mistress & Master Latin Big Cocks

51% HD 1:01 / 21:15

Sph Mistress & Master Latin Big Cocks

FapHouse 1 year ago

Gay Joy CEI

41% HD 0:39 / 17:00

FapHouse 2 months ago

Brides Hands-free BBC Cumshots

Brides Hands-free BBC Cumshots

xHamster 1 month ago

Nice Sissy Oral Pleasure Feminization Teaching, Ditzy Sissy Audio

Nice Sissy Oral Pleasure Feminization Teaching, Ditzy Sissy Audio

TrannyGem 1 year ago

Cumsluts Getting Wrecked in Intense Orgasm Compilation

Cumsluts Getting Wrecked in Intense Orgasm Compilation

XXXShake 1 year ago

Fetish foolish Marilyn Monroe like transvestite banging thick black fuck stick

Fetish foolish Marilyn Monroe like transvestite banging thick black fuck stick

TrannyGem 3 years ago

Pretty Trans Girl Throat Fucked by Tattooed Muscle Stud

Pretty Trans Girl Throat Fucked by Tattooed Muscle Stud

xHamster 4 months ago

Destroyed sissy crossdresser humiliated by femdom joi

Destroyed sissy crossdresser humiliated by femdom joi

JuicyTrans 1 week ago

Sissy Wench Jessica Bloom Plowd Hard By Biggest Ebony Weenie On Bang Machine Multiple Anal Sissygasms

Sissy Wench Jessica Bloom Plowd Hard By Biggest Ebony Weenie On Bang Machine Multiple Anal Sissygasms

ShemaleSin 4 months ago

HARD SISSY TRAINNING OUTDOOR BY HUGE STRAPON

HARD SISSY TRAINNING OUTDOOR BY HUGE STRAPON

Itsrealamateurs 2 weeks ago

Humiliating Cock Sucking Training for Sissy

Humiliating Cock Sucking Training for Sissy

Tranny.one 4 years ago

Threesome Sissy Domination

HD 0:39 / 25:56

Threesome Sissy Domination

FapHouse 6 months ago

Tiny Femboy Stretched by Huge Dildo - Fucking Machine Anal Sex Training

Tiny Femboy Stretched by Huge Dildo - Fucking Machine Anal Sex Training

FapHouse 1 month ago

Salma Naur Private Show

Salma Naur Private Show

Flirt4Free 1 year ago

Colombian Boys Private Show

47% HD 2:00 / 23:35

Colombian Boys Private Show

Flirt4Free 2 years ago

Femboy anal training with monster cocks+cum💦

Femboy anal training with monster cocks+cum💦

aShemaleTube 1 year ago

NUN SUPERVISED MASTURBATION

56% 4K 0:25 / 13:59

NUN SUPERVISED MASTURBATION

Clips4sale 2 years ago

Desire Sweet Private Show

HD 2:00 / 24:59

Desire Sweet Private Show

Flirt4Free 9 months ago

Kasnicole 317 黑丝包裹排精雌堕

Kasnicole 317 黑丝包裹排精雌堕

TrannyGem 1 year ago

Get railed screwing hard by your futa girlfriend (Sextoy JOI)

Get railed screwing hard by your futa girlfriend (Sextoy JOI)

ShemaleSin 1 week ago

Paola Balconi Private Show

Paola Balconi Private Show

Flirt4Free 1 year ago

Ivy & Headmistress; Sissification & Humiliation Punishment

58% 1:01 / 26:37

Ivy & Headmistress; Sissification & Humiliation Punishment

FapHouse 1 year ago

Black Boy Got Turn on by His Coach at the Training Section

57% HD 0:39 / 13:54

Black Boy Got Turn on by His Coach at the Training Section

FapHouse 4 months ago

Sasha de Sade Housemaid Strapon Training With Saskia

Sasha de Sade Housemaid Strapon Training With Saskia

Nuvid 4 months ago

Fuzzy Sock Gag and Chastity Pegging Indignity for Sissy with Booty-ravage Sock Slamming by Dominatrix Mercer

Fuzzy Sock Gag and Chastity Pegging Indignity for Sissy with Booty-ravage Sock Slamming by Dominatrix Mercer

TransTube.tv 1 year ago

Blond TS barebacks marine

Blond TS barebacks marine

SortPorn 3 years ago

Indian Gay Crossdresser Gaurisissy XXX Sex in Pink Honeymoon Lingerie

Indian Gay Crossdresser Gaurisissy XXX Sex in Pink Honeymoon Lingerie

xHamster 7 months ago

Hot Play of my Big Hard Cock(rasp) with Lots of Oil falling in my Balls and Ass(jerk)(d)(squirt)

64% HD 2:00 / 5:53

Hot Play of my Big Hard Cock(rasp) with Lots of Oil falling in my Balls and Ass(jerk)(d)(squirt)

Flirt4Free 5 years ago

Drag Queen Obsession

Drag Queen Obsession

xHamster 1 year ago

Brutus K Private Show

Brutus K Private Show

Flirt4Free 10 years ago

BLUE MONDAY: THE VOLUNTARY – PART 1: BONDAGE

53% 0:09 / 12:37

BLUE MONDAY: THE VOLUNTARY – PART 1: BONDAGE

Clips4sale 1 year ago

Angel Joseph Private Show

Angel Joseph Private Show

Flirt4Free 6 days ago

Rite of Passage for Real Sissies

Rite of Passage for Real Sissies

BigTitsLust 1 week ago

Raine Ryder bareback fucked by Flare Wolfsbane FULL VID

Raine Ryder bareback fucked by Flare Wolfsbane FULL VID

xHamster 5 months ago

Blake & Derek & Ethan Private Show

Blake & Derek & Ethan Private Show

Flirt4Free 3 years ago

FEMINIZED - Encouraged Feminization Play POV - Slut Training with Chastity Lock Up

45% HD 0:33 / 16:20

FEMINIZED - Encouraged Feminization Play POV - Slut Training with Chastity Lock Up

Clips4sale 1 year ago

Sia Lopez Private Show

HD 2:00 / 49:17

Sia Lopez Private Show

Flirt4Free 3 years ago

Sissy maid double dildo sucking and ass to mouth training

Sissy maid double dildo sucking and ass to mouth training

JuicyTrans 1 week ago

Fucking Femboy Ass On A Hospital Chair

Fucking Femboy Ass On A Hospital Chair

xHamster 6 days ago

Ftm Soldier Receives Humiliating Pussy Discipline Training

Ftm Soldier Receives Humiliating Pussy Discipline Training

xHamster 2 weeks ago

Wild Sabrina Private Show

Wild Sabrina Private Show

Flirt4Free 5 years ago

Tovez & Tomy Private Show

Tovez & Tomy Private Show

Flirt4Free 1 year ago

Step-Mom Teaches U How to Cum From Anal Like a Admirable Sissy Whore - Jessica Bloom Sissygasm Guide

Step-Mom Teaches U How to Cum From Anal Like a Admirable Sissy Whore - Jessica Bloom Sissygasm Guide

ShemaleSin 2 months ago

Sissy Lucy Chastity Fucked Raw by 10 Inch BBC Black Bull

Sissy Lucy Chastity Fucked Raw by 10 Inch BBC Black Bull

JuicyTrans 1 week ago

Size Queen Creation. She-Cock Superiority Training

47% HD 0:41 / 18:10

Size Queen Creation. She-Cock Superiority Training

IWantClips 4 months ago

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