Training Videos - Trans (27,116)

Sissy Slut Pegging Compilation. Femdom Chastity

Sissy Slut Pegging Compilation. Femdom Chastity

Pornzona 4 months ago

bbc bimbo sloppy deepthroat training

bbc bimbo sloppy deepthroat training

ShemaleSin 3 years ago

Sissy Crossdresser Amanda Kiss Bound Up, Teased and Denied By Femdom Girlfriend

Sissy Crossdresser Amanda Kiss Bound Up, Teased and Denied By Femdom Girlfriend

ShemaleSin 2 years ago

femboy twink in chastity gets fucked by 12 inches while wearing a bodysuit

femboy twink in chastity gets fucked by 12 inches while wearing a bodysuit

xHamster 11 months ago

Big black cock Ditzy Gags With Duck Plumbs

Big black cock Ditzy Gags With Duck Plumbs

TransTube.tv 2 months ago

Sissy Slut Cum training

Sissy Slut Cum training

UrGayPorn 2 years ago

Trans joi. Intensive edge, ruin and then cum with me. Biggest load

Trans joi. Intensive edge, ruin and then cum with me. Biggest load

ShemaleSin 2 years ago

Sissy Dolly's Sextoy Gauntlet - Attempt 1

Sissy Dolly's Sextoy Gauntlet - Attempt 1

ShemaleSin 1 year ago

BBW stepmom sissy Training with strap on dildo - crossdresser fucked

BBW stepmom sissy Training with strap on dildo - crossdresser fucked

xHamster 2 years ago

Orgasm control with ruined cumshot for sissy femboy

Orgasm control with ruined cumshot for sissy femboy

xHamster 2 years ago

Step mommy trains you how to be a CD schlong sucker humiliation

Step mommy trains you how to be a CD schlong sucker humiliation

XXXShemalePorn 2 years ago

Compilation hot babe with stap-on fucks her bestie femboy in sexy lingerie and stockings in anal

Compilation hot babe with stap-on fucks her bestie femboy in sexy lingerie and stockings in anal

XCafe 11 months ago

Little Serving Sissy Wench

Little Serving Sissy Wench

xHamster 5 months ago

Exploring a dark tunnel with a black dildo

Exploring a dark tunnel with a black dildo

XXXShemalePorn 11 months ago

femdom futa Mommy pegs you and makes you her cocksucking sissy slut - full video on veggiebabyy Manyvids

femdom futa Mommy pegs you and makes you her cocksucking sissy slut - full video on veggiebabyy Manyvids

xHamster 3 years ago

You're HOMO for Large Nads ft Queen Colleen

You're HOMO for Large Nads ft Queen Colleen

TransTube.tv 1 year ago

Skinny Tgirl Ryu Doll pleases her anal hole with a fucking machine

Skinny Tgirl Ryu Doll pleases her anal hole with a fucking machine

MyLust 2 years ago

8 Sissygams for Mistress, 1 Orgasm for Sissy

8 Sissygams for Mistress, 1 Orgasm for Sissy

xHamster 2 weeks ago

Sissy Slut Fucked Hard By BBW Mistress In The Ass

Sissy Slut Fucked Hard By BBW Mistress In The Ass

xHamster 1 year ago

Cute Sissy Chastity Thrall Released to be Teased Denied Abased and Locked Up by Mastix Mercer

Cute Sissy Chastity Thrall Released to be Teased Denied Abased and Locked Up by Mastix Mercer

ShemaleSin 4 years ago

Sissy Maid Is Taught Proper Manners

Sissy Maid Is Taught Proper Manners

FapHouse 2 weeks ago

spoiled daddy double pissing blowjobs rimjobs deep anal 2 trans girls in chastity

spoiled daddy double pissing blowjobs rimjobs deep anal 2 trans girls in chastity

PissVids 9 months ago

Mouth fucking a deepthroated sissy bitch while watching porn

Mouth fucking a deepthroated sissy bitch while watching porn

xHamster 4 years ago

Sissy Anna playing Outdoor on Balcony with Sextoy - Anal & Blow Training

Sissy Anna playing Outdoor on Balcony with Sextoy - Anal & Blow Training

ShemaleSin 4 months ago

Sissy tramp rectal teaching with tomatoes.

Sissy tramp rectal teaching with tomatoes.

TrannyGem 3 weeks ago

Sissy website previews - R..a..c..h..a..e..l B..e..l..l..e

Sissy website previews - R..a..c..h..a..e..l B..e..l..l..e

PornoXO 1 month ago

Sissy Training - Feminization - Sissy TASK - when u watch a angel

Sissy Training - Feminization - Sissy TASK - when u watch a angel

ShemaleSin 1 year ago

Caged Sissy Is Used as a Fuck Toy Part 2

60% HD 1:01 / 17:00

Caged Sissy Is Used as a Fuck Toy Part 2

FapHouse 1 month ago

Caught in the Act (Sissy caption Story)

Caught in the Act (Sissy caption Story)

ShemaleSin 4 years ago

Slave fucked and dick🍆 trapped in chastity gear

Slave fucked and dick🍆 trapped in chastity gear

AnalPornXL 1 year ago

Dog training

aShemaleTube 2 years ago

HornyEmpressKay - obedience training

HornyEmpressKay - obedience training

ShemaleSin 2 years ago

Cockhungry MILFs pounded by BBC in threesome

Cockhungry MILFs pounded by BBC in threesome

Some.Porn 3 months ago

Sissy sucking tutor

Sissy sucking tutor

ShemaleSin 3 years ago

Cumshot, riding – hardcore anal fucking for gays

Cumshot, riding – hardcore anal fucking for gays

Anal.media 1 month ago

hot femboy riding dildo

hot femboy riding dildo

BallsAndBoobs 1 year ago

1st Time Trying Anal fisting Supper Tight Hole Stretch Open

1st Time Trying Anal fisting Supper Tight Hole Stretch Open

xHamster 4 years ago

Training with Anna

Training with Anna

aShemaleTube 2 years ago

Jenny enjoying a fat cucumber 2

Jenny enjoying a fat cucumber 2

xHamster 2 months ago

Femdom Girlfriend Trains Sissy Maid To Suck Jock

Femdom Girlfriend Trains Sissy Maid To Suck Jock

ShemaleSin 4 years ago

Drag Queen Obsession

Drag Queen Obsession

xHamster 1 year ago

QOS Sissy Lola Crystals gets second internal ejaculation from FAT BIG BLACK COCK Fuckbuddy

QOS Sissy Lola Crystals gets second internal ejaculation from FAT BIG BLACK COCK Fuckbuddy

TrannyGem 3 years ago

TS Ass Stretching

HD 1:01 / 19:19

TS Ass Stretching

FapHouse 1 month ago

Transsexual Training Day

Transsexual Training Day

xHamster 3 years ago

An amateur man&#039;s maid plays naughty with her buttocks [Personal shooting]

An amateur man&#039;s maid plays naughty with her buttocks [Personal shooting]

xHamster 1 year ago

Subordination Teaching crushing scrotum PINK CIGAR BALL TORMENT

Subordination Teaching crushing scrotum PINK CIGAR BALL TORMENT

GayVids 2 years ago

全身痙攣

TrannyGem 3 weeks ago

Charli's Nightly Routine

Charli's Nightly Routine

ShemaleSin 2 months ago

Playing-white Annete129

Playing-white Annete129

xHamster 1 year ago

Self Pee Anal Pumped Swollen Ass Hole

Self Pee Anal Pumped Swollen Ass Hole

xHamster 2 months ago

2032 - the Bwno Future

2032 - the Bwno Future

xHamster 2 months ago

”Punk Pokemon beauty gets a training session”

”Punk Pokemon beauty gets a training session”

ThePornstar 1 year ago

Brunette Shemale In Crotchless Fishnet Pantyhose Surrenders Her Asshole To a Merciless Fuck-machine

Brunette Shemale In Crotchless Fishnet Pantyhose Surrenders Her Asshole To a Merciless Fuck-machine

XGroovy 2 years ago

Shemale slut training in sexy lingerie and stockings

Shemale slut training in sexy lingerie and stockings

xHamster 3 years ago

Making my sissy suck mommys cock

Making my sissy suck mommys cock

xHamster 8 months ago

SISSY TRAINNING & CUMSHOTS COMPILATION

SISSY TRAINNING & CUMSHOTS COMPILATION

ShemaleSin 5 months ago

Sissygasm for Domina

Sissygasm for Domina

FapHouse 4 months ago

Milking! Double Sissygasm!

Milking! Double Sissygasm!

xHamster 1 year ago

Transgender in high heels and lingerie does anal beads

Transgender in high heels and lingerie does anal beads

xHamster 1 year ago

Crossdresser Office Nymph Assfuck Training(1/4)

Crossdresser Office Nymph Assfuck Training(1/4)

2BGay 1 year ago

”Kemono Dragon trains my raw butt to overcome dildo & his dick”

”Kemono Dragon trains my raw butt to overcome dildo & his dick”

TransHero 1 week ago

Ultra-naughty Masseuse Latex Glove Fisting with XXL rosebud and GAPE for Sissy Hoe by Mistress Mercer

Ultra-naughty Masseuse Latex Glove Fisting with XXL rosebud and GAPE for Sissy Hoe by Mistress Mercer

TransTube.tv 1 year ago

Ohww... Blake Is Loving Me so Much - the Lust of Sissy Boy Saga

65% HD 1:01 / 10:20

Ohww... Blake Is Loving Me so Much - the Lust of Sissy Boy Saga

FapHouse 7 months ago

Becoming A Sissy (JOI) w/ Raven Gray

Becoming A Sissy (JOI) w/ Raven Gray

FapCat 2 years ago

TGIRLS.XXX - Boss Bitch Training

TGIRLS.XXX - Boss Bitch Training

Fapnado 8 months ago

full mouth gag device bondage submissive tgirl shock collar pain slut training

63% HD 0:29 / 13:38

full mouth gag device bondage submissive tgirl shock collar pain slut training

PornBox 11 months ago

Tail plug on a early morning walk

Tail plug on a early morning walk

ShemaleSin 4 months ago

Sissy Pigg by Camp Sissyboi

Sissy Pigg by Camp Sissyboi

xHamster 1 year ago

Ria Bentley Grindr Ultimate Sissy Bang Doll Tutor

Ria Bentley Grindr Ultimate Sissy Bang Doll Tutor

ShemaleSin 3 months ago

Jasmine_dlight & Hannah Blake - Shemale Fuckslut Ruined by Mistress - Bound & Fucked Hard with Huge Strapon

HD 1:01 / 10:02

Jasmine_dlight & Hannah Blake - Shemale Fuckslut Ruined by Mistress - Bound & Fucked Hard with Huge Strapon

FapHouse 7 months ago

femboy hops on a fake penis and sissygasming

femboy hops on a fake penis and sissygasming

TrannyGem 3 years ago

anal monster destroys the anal of a sissy in a chastity belt. crossdresser training sissy whore

anal monster destroys the anal of a sissy in a chastity belt. crossdresser training sissy whore

SukaPorn 1 year ago

Sexy Ditzy Captions

Sexy Ditzy Captions

TrannyGem 2 years ago

Verbal Daddy Helps me Train my hole

Verbal Daddy Helps me Train my hole

xHamster 1 year ago

Ts Diana Deelight sucking on and bouncing on a big black dick compilation

Ts Diana Deelight sucking on and bouncing on a big black dick compilation

xHamster 2 months ago

Sissy Takes 13 Inch Horse Vibrator

Sissy Takes 13 Inch Horse Vibrator

ShemaleSin 3 weeks ago

What A Trap For Workouts

What A Trap For Workouts

ShemaleSex 1 week ago

Little Serving Sissy Wench

51% HD 1:01 / 10:38

Little Serving Sissy Wench

FapHouse 5 months ago

Shemale in thong pounding gaping ass with octopus dildo and jerking big cock to cumshot

Shemale in thong pounding gaping ass with octopus dildo and jerking big cock to cumshot

xHamster 10 months ago

Xl Inflatable Plug Inside a Femboy's Butt

57% HD 1:01 / 7:55

Xl Inflatable Plug Inside a Femboy's Butt

FapHouse 1 year ago

Trinity Noir Anal training session

Trinity Noir Anal training session

ShemaleSin 2 years ago

Emotional moment from "Sissy shemale in chastity rides dildo on her pillow with passion and gives him a nice deepthroat"

Emotional moment from "Sissy shemale in chastity rides dildo on her pillow with passion and gives him a nice deepthroat"

xHamster 1 month ago

blowing pricks compliation and getting a facial cumshot

blowing pricks compliation and getting a facial cumshot

TransTube.tv 1 year ago

Lily Star Takes fist and mini-mini-rosebud for first-ever-ever time!

Lily Star Takes fist and mini-mini-rosebud for first-ever-ever time!

TransTube.tv 1 year ago

Saggy Tits Humiliation Dom Training Bra

67% HD 1:01 / 6:22

Saggy Tits Humiliation Dom Training Bra

FapHouse 1 year ago

Asian Twink Army Anal Training

Asian Twink Army Anal Training

xHamster 1 year ago

G082 - Lola Creampie 8, breeding 1

59% HD 1:01 / 12:11

G082 - Lola Creampie 8, breeding 1

FapHouse 2 months ago

Unforgettable moment from "Crossdressed Sissy lana get fucked with selfmade gyno chair"

Unforgettable moment from "Crossdressed Sissy lana get fucked with selfmade gyno chair"

xHamster 2 months ago

Dildo Training 53,446 Views Added 2024-09-25

Dildo Training 53,446 Views Added 2024-09-25

getTranny 1 month ago

Cumslut Pop Training 4

Cumslut Pop Training 4

aShemaleTube 1 year ago

JoJo cocksuck training 2

JoJo cocksuck training 2

GayCK 4 years ago

Dad Bangs Trans Slut Humid

Dad Bangs Trans Slut Humid

Transvids.tv 1 year ago

Feminization Sissification Sissy threesome training blowjob

Feminization Sissification Sissy threesome training blowjob

Lesbian8 6 months ago

Started Without You

Started Without You

xHamster 3 months ago

Trans Rubber Sissy Maid Doing Dishes

Trans Rubber Sissy Maid Doing Dishes

ShemaleSin 10 months ago

Horny Tranny cycling! She fucks her ass with the saddle and cums on the bike

Horny Tranny cycling! She fucks her ass with the saddle and cums on the bike

xHamster 1 year ago

Sissy Training by a Hot Dominatrix

Sissy Training by a Hot Dominatrix

xHamster 8 years ago

Sissy Blaire_18 sucks my strap-on, masturbates the toy with her hair, and practices deep throating. POV.

Sissy Blaire_18 sucks my strap-on, masturbates the toy with her hair, and practices deep throating. POV.

xHamster 2 weeks ago

Hard belt self spanking Part 3

Hard belt self spanking Part 3

xHamster 1 year ago

My Ultimate Fantasy - Pegging Step Brother

My Ultimate Fantasy - Pegging Step Brother

xHamster 1 month ago

Sissy Chayenne Dildo Training

Sissy Chayenne Dildo Training

xHamster 1 year ago

Sissy Lovelaska - hot anal games. Balls and big dildo

Sissy Lovelaska - hot anal games. Balls and big dildo

xHamster 4 years ago

Becky Scolds Sissy Slut Michel for Not Cleaning the Kitchen Properly

Becky Scolds Sissy Slut Michel for Not Cleaning the Kitchen Properly

xHamster 1 year ago

ai que delicia dei gostoso pro entregador, daniela santos solosts1

ai que delicia dei gostoso pro entregador, daniela santos solosts1

SukaPorn 1 month ago

Femboy Assfuck Have Fun needed the 8 Inch Fuck-Stick in my Culo

Femboy Assfuck Have Fun needed the 8 Inch Fuck-Stick in my Culo

TrannyGem 2 weeks ago

Thick crossdresser gets by machine

Thick crossdresser gets by machine

xHamster 11 months ago

Tutorial vid - Lesson 1. How to milk guts with only 1 finger

Tutorial vid - Lesson 1. How to milk guts with only 1 finger

TrannyGem 3 years ago

Caught in my Web

Caught in my Web

ShemaleSin 2 months ago

Indian Gay Crossdresser Gaurisissy Pressing Her Big Boobs in Balck Saree XXX Sex

Indian Gay Crossdresser Gaurisissy Pressing Her Big Boobs in Balck Saree XXX Sex

xHamster 1 month ago

becomingfemme - clarice darling showing off her progression

becomingfemme - clarice darling showing off her progression

TransDoe 1 year ago

Ep9: Fucking Harpie Ava Against the Wall (sex Pose 4) - Orc Massage

Ep9: Fucking Harpie Ava Against the Wall (sex Pose 4) - Orc Massage

xHamster 1 year ago

Fuck Us Both Billy

HD 1:01 / 26:20

Fuck Us Both Billy

FapHouse 3 months ago

Hot petite Jamie Markham gets anal workout

69% HD 1:01 / 23:20

Hot petite Jamie Markham gets anal workout

FapHouse 2 years ago

Giant bum candid upskirt, moving purity key to a bus stop

Giant bum candid upskirt, moving purity key to a bus stop

TrannyGem 11 months ago

Summer Raine - Summer Rayne Summer Training

Summer Raine - Summer Rayne Summer Training

AbTranny 4 years ago

Sissy plays with holes to music

Sissy plays with holes to music

BallsAndBoobs 2 weeks ago

Japanese Femdom, Reiko Butler's Slave Domestication Training

Japanese Femdom, Reiko Butler's Slave Domestication Training

xHamster 5 years ago

Joven Ladyboy Tiene Orgasmo Analyoung Ladyboy Has a Sissygasm

Joven Ladyboy Tiene Orgasmo Analyoung Ladyboy Has a Sissygasm

xHamster 4 weeks ago

Riding boots trampling and boot fetish

Riding boots trampling and boot fetish

xHamster 2 years ago

Personal Training - Sabrina Alves

Personal Training - Sabrina Alves

AbTranny 3 months ago

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