Training Videos - Trans (89,930)

Sissy Trainer: Destroyed Ass pumps Hard Dildo

Sissy Trainer: Destroyed Ass pumps Hard Dildo

xHamster 1 year ago

Feminization - Sissification - Sissy Training - Sissy Support - full version - two

Feminization - Sissification - Sissy Training - Sissy Support - full version - two

ShemaleSin 2 years ago

Sissygasm Doxy Caged Training Giant Spunk Flow & Anal Milking Jessica Bloom

Sissygasm Doxy Caged Training Giant Spunk Flow & Anal Milking Jessica Bloom

ShemaleSin 4 years ago

Naughty Brown-haired babe with pierced pussy gets doggystyled and fucked in various positions

Naughty Brown-haired babe with pierced pussy gets doggystyled and fucked in various positions

Some.Porn 2 years ago

Having a Hard Time 7: Shemale Jane's Full Body Massage on Anna

45% HD 0:39 / 15:36

Having a Hard Time 7: Shemale Jane's Full Body Massage on Anna

FapHouse 3 months ago

Candid upskirt g-string

Candid upskirt g-string

TrannyGem 1 year ago

Hammering balls

Hammering balls

xHamster 2 years ago

gay slut ryan743 anal training

gay slut ryan743 anal training

xHamster 6 days ago

trans sissy fleshlight fucking multiple orgasm compilation (preview!)

trans sissy fleshlight fucking multiple orgasm compilation (preview!)

Pornzona 1 month ago

Half hour chilling on the sex machine, daily anal fuck and depth training smoking lounging

Half hour chilling on the sex machine, daily anal fuck and depth training smoking lounging

xHamster 3 years ago

Mama's Guidance - ASMR Trans Camgirl Training

Mama's Guidance - ASMR Trans Camgirl Training

SortPorn 3 weeks ago

hot kinky cd stretches own hungry ass pussy till sissygasm – WARM-UP

hot kinky cd stretches own hungry ass pussy till sissygasm – WARM-UP

xHamster 4 years ago

Juanita Swan Private Show

57% HD 2:00 / 6:43

Juanita Swan Private Show

Flirt4Free 2 years ago

pec play

Flirt4Free 14 years ago

Sexy crossdresser gets his farting anal cunt creamy fucked by the machine.

Sexy crossdresser gets his farting anal cunt creamy fucked by the machine.

xHamster 1 year ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 6 months ago

Hercules & Lance & Lian Miller Private Show

63% HD 2:00 / 8:05

Hercules & Lance & Lian Miller Private Show

Flirt4Free 3 years ago

Sissy Monique - Slutwalk in the redlight district

Sissy Monique - Slutwalk in the redlight district

xHamster 6 months ago

Buy your ticket and let me show you my sexual skills! To start let me get undressed to you and jerk my big cock like a semental.

Buy your ticket and let me show you my sexual skills! To start let me get undressed to you and jerk my big cock like a semental.

Flirt4Free 4 years ago

Drill Machine Ruin my Culo

Drill Machine Ruin my Culo

TrannyGem 1 year ago

Vanessa Mancini Private Show

HD 2:00 / 15:16

Vanessa Mancini Private Show

Flirt4Free 3 years ago

Alice Woonder Private Show

HD 2:00 / 21:28

Alice Woonder Private Show

Flirt4Free 2 years ago

HARD FUCKING AND FISTING OF A CROSSDRESSER IN A CHASTITY BELT! FEMINIZATION. SISSIFICATION.

Premium HD 8:05

HARD FUCKING AND FISTING OF A CROSSDRESSER IN A CHASTITY BELT! FEMINIZATION. SISSIFICATION.

Sheer 3 years ago

Self-training No. 38: Daily Tucked Pussy Exposure Walk

Self-training No. 38: Daily Tucked Pussy Exposure Walk

xHamster 4 months ago

Powerful moment from "Mistress gonna transform you in a sissy fucktoy and make your ass sore (FEMINIZATION ROLEPLAY - AI"

Powerful moment from "Mistress gonna transform you in a sissy fucktoy and make your ass sore (FEMINIZATION ROLEPLAY - AI"

xHamster 1 year ago

Sissy Kitten Fastened in Bitchsuit and Anal Banged with Sex Machine

Sissy Kitten Fastened in Bitchsuit and Anal Banged with Sex Machine

ShemaleSin 4 years ago

Petra,s 3rd solo training

Petra,s 3rd solo training

xHamster 10 months ago

large collection of all femboy anal penetrations from 2025.

large collection of all femboy anal penetrations from 2025.

ShemaleSin 3 months ago

Day 22 of Sissy Training - Public Panty Peril

HD 0:39 / 20:07

Day 22 of Sissy Training - Public Panty Peril

FapHouse 2 weeks ago

Sara & Elver Private Show

Sara & Elver Private Show

Flirt4Free 5 months ago

Trans slut Daphne dreams of big cocks while fucking herself with a 7 inch pink dildo

Trans slut Daphne dreams of big cocks while fucking herself with a 7 inch pink dildo

xHamster 1 month ago

CD Allie North I’m a orgy sway

CD Allie North I’m a orgy sway

TrannyGem 3 years ago

Chubby Maram Play with Her Dildo so Hot Sexy Trans

Chubby Maram Play with Her Dildo so Hot Sexy Trans

xHamster 7 months ago

Sissy Maid Is Taught Proper Manners

Sissy Maid Is Taught Proper Manners

ShemaleSin 4 months ago

Tammy Frizz Private Show

Tammy Frizz Private Show

Flirt4Free 1 month ago

Bimbo Takes on BBC

HD 0:39 / 16:44

Bimbo Takes on BBC

FapHouse 5 months ago

Boy Undergoes Sissy Training! (Teaser)

Boy Undergoes Sissy Training! (Teaser)

aShemaleTube 2 years ago

Femboy Sissy Assplay Training XL Dildo 25 cm

Femboy Sissy Assplay Training XL Dildo 25 cm

xHamster 3 months ago

Onyushka Anal Training With Big Sex Toy

Onyushka Anal Training With Big Sex Toy

VipTube 3 months ago

Veronica Reynolds Private Show

Veronica Reynolds Private Show

Flirt4Free 2 years ago

The Feminized Husband: An FLR Tale 2

52% HD 0:30 / 36:55

The Feminized Husband: An FLR Tale 2

Clips4sale 1 year ago

Large Ebony Weenie Feminization Coach for Constrained Sissy Lads (BBC) (Captions)

Large Ebony Weenie Feminization Coach for Constrained Sissy Lads (BBC) (Captions)

ShemaleSin 4 years ago

Naruto - Training Tsunade - Big Cock futa babe Fuck Busty Big boob MILF

Naruto - Training Tsunade - Big Cock futa babe Fuck Busty Big boob MILF

Fapcat 3 years ago

Training my sissy mouth with fake cock

Training my sissy mouth with fake cock

xHamster 2 years ago

Anne Johnsons Private Show

Anne Johnsons Private Show

Flirt4Free 1 week ago

Sophia Loreen Private Show

HD 2:00 / 23:35

Sophia Loreen Private Show

Flirt4Free 3 days ago

Sissy Joy Button Stroking and Ass Fucking Spreading! Sissification of Quinne

Sissy Joy Button Stroking and Ass Fucking Spreading! Sissification of Quinne

TrannyGem 4 years ago

3 Latino Studs in Group Show

HD 2:00 / 45:06

3 Latino Studs in Group Show

Flirt4Free 7 years ago

”Butt In Training - Tommy Trains Haley Reed's Butt For Cum Draining”

”Butt In Training - Tommy Trains Haley Reed's Butt For Cum Draining”

TransHero 4 months ago

Sissy Training 15 - Make Your Clitty Smaller

62% HD 1:01 / 6:14

Sissy Training 15 - Make Your Clitty Smaller

FapHouse 1 year ago

Vicky Katherine Private Show

63% HD 2:00 / 8:41

Vicky Katherine Private Show

Flirt4Free 2 years ago

Throat Training

Throat Training

xHamster 3 months ago

Veronica Reynolds Private Show

HD 2:00 / 14:29

Veronica Reynolds Private Show

Flirt4Free 2 years ago

Bryan is Pantied and Plugged

57% HD 0:30 / 11:04

Bryan is Pantied and Plugged

OnlyPornVideo 3 months ago

Amy Milerus Private Show

HD 2:00 / 36:28

Amy Milerus Private Show

Flirt4Free 2 years ago

Jimmy & Roy Private Show

HD 2:00 / 1:05:11

Jimmy & Roy Private Show

Flirt4Free 3 years ago

Latex Sissy suffer a fucking machine

Latex Sissy suffer a fucking machine

xHamster 1 year ago

Pretty Femboy stretches his hole with big dildo

Pretty Femboy stretches his hole with big dildo

Pornzona 1 month ago

Khalifa Gold & Lissa Hamilton Private Show

Khalifa Gold & Lissa Hamilton Private Show

Flirt4Free 7 months ago

”The Seductive Twist: Daisy Taylor's Rebellious Massage Adventure”

”The Seductive Twist: Daisy Taylor's Rebellious Massage Adventure”

StarWank 2 years ago

Big tits blonde transsexual EMT trainer Jade Venus fucking her student

Big tits blonde transsexual EMT trainer Jade Venus fucking her student

Pervclips 2 weeks ago

Hottest Cock Milking Ever

HD 1:01 / 12:34

Hottest Cock Milking Ever

FapHouse 3 months ago

Taking a 17inch Dildo All the Way Inside Me!

Taking a 17inch Dildo All the Way Inside Me!

xHamster 1 year ago

David Colllins Private Show

David Colllins Private Show

Flirt4Free 1 month ago

Lyndon F Private Show

HD 2:00 / 24:42

Lyndon F Private Show

Flirt4Free 1 month ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 9 months ago

Milking the first drops from my SISSY's PROSTATE

Milking the first drops from my SISSY's PROSTATE

xHamster 1 year ago

The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)

62% HD 0:39 / 7:20

The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)

FapHouse 7 months ago

I Really Like This Position on Four

I Really Like This Position on Four

xHamster 2 weeks ago

Attempt to put love glove on lil will-less sissy spunk-pump

Attempt to put love glove on lil will-less sissy spunk-pump

TrannyGem 2 years ago

Lizzy Yum lonely girl - BDSM erotic shock training, E prod, toy shock collar, lonely girl #4

Lizzy Yum lonely girl - BDSM erotic shock training, E prod, toy shock collar, lonely girl #4

xHamster 3 years ago

Leyla Steel Private Show

55% 4K 2:00 / 8:31

Leyla Steel Private Show

Flirt4Free 11 months ago

Anal training (rem cosplay)

Anal training (rem cosplay)

ManPorn 6 years ago

Brutus K Private Show

Brutus K Private Show

Flirt4Free 7 years ago

”Brunette Transgender Saki Cruise broken in by Charlotte Sartre with rough fucking”

”Brunette Transgender Saki Cruise broken in by Charlotte Sartre with rough fucking”

LesbianBliss 2 months ago

Tranny urgently needs to pee during workout! Perverted Wetting - soaking wet continued training!

Tranny urgently needs to pee during workout! Perverted Wetting - soaking wet continued training!

xHamster 3 years ago

Фембой Hattabi4ik сквирт оргазм компиляция сочная жопа анальные игрушки анальный оргазм шлюхи

Фембой Hattabi4ik сквирт оргазм компиляция сочная жопа анальные игрушки анальный оргазм шлюхи

XVideos 11 months ago

Mira Delynn Private Show

Mira Delynn Private Show

Flirt4Free 3 months ago

SISSY INFLATABLE ANAL PLUG

SISSY INFLATABLE ANAL PLUG

xHamster 2 years ago

booty total of meaty stud-meat sissy fag supah-slut riding huge humungous manmeat

booty total of meaty stud-meat sissy fag supah-slut riding huge humungous manmeat

Gay4Porn 6 months 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 1 month ago

Marvelous TGirl Gigi gets her arse depth trained by Lisa

Marvelous TGirl Gigi gets her arse depth trained by Lisa

TransTube.tv 1 year ago

Roman Todd's rimjob and spooning with Jade Venus

Roman Todd's rimjob and spooning with Jade Venus

UrGayPorn 9 months ago

I show my sissy hot body in the toalet train

I show my sissy hot body in the toalet train

xHamster 3 years ago

SUBMISSIVE SKINNY LADYBOY ANAL CREAMPIE &amp_ FISTING

Premium HD 6:36

SUBMISSIVE SKINNY LADYBOY ANAL CREAMPIE &amp_ FISTING

xnxxGold 3 months ago

Aleex & Paulo Private Show

55% HD 2:00 / 17:52

Aleex & Paulo Private Show

Flirt4Free 11 months ago

PLAY WITH MY OPEN HOLE - Part 16

PLAY WITH MY OPEN HOLE - Part 16

Flirt4Free 1 year ago

POV Trans Step-sister Feminizes U Into Her Personal Sissy Doll

POV Trans Step-sister Feminizes U Into Her Personal Sissy Doll

ShemaleSin 1 year ago

sissy training#3 running in flows anal in swimsuit

sissy training#3 running in flows anal in swimsuit

2BGay 2 years ago

Training the sissy to be My CUMSLUT

HD 0:10 / 21:38

Training the sissy to be My CUMSLUT

LoyalFans 2 years ago

Kendal Smithx Private Show

Kendal Smithx Private Show

Flirt4Free 2 weeks ago

Luca Ferrero In Trains His Tranny Deep

Luca Ferrero In Trains His Tranny Deep

uAnal 3 months ago

Dani Saenz Private Show

HD 2:00 / 22:35

Dani Saenz Private Show

Flirt4Free 4 years ago

Me da pena hacer un trio con tu amiga, trio con dos vaquitas me sacan la leche

Me da pena hacer un trio con tu amiga, trio con dos vaquitas me sacan la leche

XVideosRed 6 months ago

Sissy CD Assfuck Fake-Pink Cigar On The Floor Jizz Have Joy

Sissy CD Assfuck Fake-Pink Cigar On The Floor Jizz Have Joy

2BGay 2 years ago

Dancing Night Club

HD 2:00 / 42:26

Dancing Night Club

Flirt4Free 1 year ago

Diabla Rivers & Rouse Morgan Private Show

63% HD 2:00 / 7:11

Diabla Rivers & Rouse Morgan Private Show

Flirt4Free 2 years ago

Interracial Pair Constricted Ass Plug Prostate Training During The Time That Large Titties GF Rides my FTM BBC Knob Cowgirl

Interracial Pair Constricted Ass Plug Prostate Training During The Time That Large Titties GF Rides my FTM BBC Knob Cowgirl

ShemaleSin 4 years ago

Bnwo - Your Whiteboy Future

Bnwo - Your Whiteboy Future

Clips4sale 10 months ago

Sleek sissy locked in a lil' innocence gapes her caboose with a thick fuck stick

Sleek sissy locked in a lil' innocence gapes her caboose with a thick fuck stick

TrannyGem 4 years ago

A Latex Fuck Doll Gets Strapped on by Femdom Women

HD 0:39 / 21:27

A Latex Fuck Doll Gets Strapped on by Femdom Women

FapHouse 5 months ago

Creamy Femboi Bussy Fucked by Sex Machine

Creamy Femboi Bussy Fucked by Sex Machine

xHamster 2 years ago

FUCKING MACHINE ANAL TRAINING

FUCKING MACHINE ANAL TRAINING

xHamster 3 years ago

Freja playing with dildo in black lingerie and heels part 1

Freja playing with dildo in black lingerie and heels part 1

xHamster 4 years ago

Sissys Dream 2

66% HD 0:39 / 10:58

FapHouse 10 months ago

Azalea Julianna Private Show

Azalea Julianna Private Show

Flirt4Free 2 months ago

Jasmine_dlight & Bambi Brat - Extreme Knee Deep Footing & Leg Insertion

Jasmine_dlight & Bambi Brat - Extreme Knee Deep Footing & Leg Insertion

FapHouse 5 days ago

Little Ponyboy in High Heels and Sexy Dress

Little Ponyboy in High Heels and Sexy Dress

FapHouse 2 years ago

Transgender Sergeant Izzy Wilde Dominates Male Recruit In Military BDSM Training Session

Transgender Sergeant Izzy Wilde Dominates Male Recruit In Military BDSM Training Session

aShemaleTube 4 months ago

Orianna Dunn Private Show

Orianna Dunn Private Show

Flirt4Free 2 years ago

Three Tranyys Conversing and tugging 1

Three Tranyys Conversing and tugging 1

TransTube.tv 1 year ago

Andrea & Taty Private Show

HD 2:00 / 34:09

Andrea & Taty Private Show

Flirt4Free 6 months ago

BRAZILIAN TRANS SLAVE TRAINING &amp_ ANAL FISTING

Premium HD 32:52

BRAZILIAN TRANS SLAVE TRAINING &amp_ ANAL FISTING

xnxxGold 4 months ago

fine butt out for a walk

fine butt out for a walk

ShemaleSin 2 years ago

Cumming and Plumber Dildo

Cumming and Plumber Dildo

xHamster 7 months ago

Chubby Amateur Latino Trans Uses Buttplug

63% HD 2:00 / 3:55

Chubby Amateur Latino Trans Uses Buttplug

Flirt4Free 8 years ago

Climax Aleksa Fantasies solo cosplay

Climax Aleksa Fantasies solo cosplay

ShemaleSin 6 days ago

Jewel Selfsucker Private Show

Jewel Selfsucker Private Show

Flirt4Free 3 months ago

Trans determined to dilute the gulp with his succulent nut nectar

Trans determined to dilute the gulp with his succulent nut nectar

TrannyGem 10 months ago

Before the Walk, Sissy Sonechka25 Filled Her Own Ass with Her Client's Cum

60% 1:01 / 5:17

Before the Walk, Sissy Sonechka25 Filled Her Own Ass with Her Client's Cum

FapHouse 1 year ago

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