Training (87 854)

A Day in the Sissy Life

66% HD 1:01 / 15:11

A Day in the Sissy Life

FapHouse il y a 11 mois

She's Going to Fist Her Girlfriend Until Her Stomach Moves

71% 1:01 / 7:25

She's Going to Fist Her Girlfriend Until Her Stomach Moves

FapHouse il y a 8 mois

Sissy in Fishnet Is Squirting While She Gets Deep Anal Fisted

72% HD 0:39 / 3:13

Sissy in Fishnet Is Squirting While She Gets Deep Anal Fisted

FapHouse il y a 4 mois

ONE OF THE BEST SISSY TRAINING VIDEOS

ONE OF THE BEST SISSY TRAINING VIDEOS

Tranny.one il y a 4 ans

Daphne Trans Shaking the Ass of a Naughty Femboy on the Male's Cock - Ai Arte

54% HD 0:39 / 2:06

Daphne Trans Shaking the Ass of a Naughty Femboy on the Male's Cock - Ai Arte

FapHouse il y a 2 mois

how to use a fufu pinch

how to use a fufu pinch

TrannyGem il y a 2 ans

Feminization Sissification Sissy Threesome Training Blowjob

Feminization Sissification Sissy Threesome Training Blowjob

BeMyHole il y a 1 an

Sissy Training by Queen Daralis Part 3

56% HD 0:39 / 9:18

Sissy Training by Queen Daralis Part 3

FapHouse il y a 1 mois

Anal Training Compilation

Anal Training Compilation

BeMyHole il y a 3 ans

TS Training

xHamster il y a 1 an

Trans Anal Training with Dildo

Trans Anal Training with Dildo

xHamster il y a 8 mois

Sissy Slut Trained and Spit Roasted

Sissy Slut Trained and Spit Roasted

Pornwhite il y a 7 mois

Sissy Slut Adventures Volume 1

Sissy Slut Adventures Volume 1

JuicyVid il y a 2 mois

feminisation training

feminisation training

xHamster il y a 2 mois

Another Straight Boy in Conversion Challenge

Another Straight Boy in Conversion Challenge

Tranny.one il y a 4 ans

Sissy Slut Training

Sissy Slut Training

xHamster il y a 1 an

Russian sissy training camp

Russian sissy training camp

Eporner il y a 1 an

Sissy Bimbo Training

Sissy Bimbo Training

Tranny.one il y a 4 ans

Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm

Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm

xHamster il y a 1 an

My Path to Life as A Sissy Hoe

My Path to Life as A Sissy Hoe

TrannyGem il y a 6 ans

Nyxi Leon / 19yo French Maid Trained Doggy Style

Nyxi Leon / 19yo French Maid Trained Doggy Style

Tranny.one il y a 4 ans

Whife *

TrannyGem il y a 6 ans

Sissy Lilly and her Training

Sissy Lilly and her Training

Tranny.one il y a 3 ans

Mistress Trains Her Sissy Gurls

Mistress Trains Her Sissy Gurls

BeMyHole il y a 5 ans

2032 - the Bwno Future

2032 - the Bwno Future

xHamster il y a 5 mois

Living His Best Life as a Girl

68% 0:39 / 27:47

Living His Best Life as a Girl

FapHouse il y a 8 mois

Patiently Waiting for Her Man

Patiently Waiting for Her Man

xHamster il y a 3 mois

Sissy Slave Training

Sissy Slave Training

BeMyHole il y a 5 ans

Sissy instructing - Enjoy For Assfucking Fucky-fucky

Sissy instructing - Enjoy For Assfucking Fucky-fucky

TransTube.tv il y a 9 mois

Mistress wants to dress you up like her fucktoy and help you train with a strap-on (FEMINIZATION ROLEPLAY - AI GENERATED)

Mistress wants to dress you up like her fucktoy and help you train with a strap-on (FEMINIZATION ROLEPLAY - AI GENERATED)

xHamster il y a 10 mois

Gag Slut Training

Gag Slut Training

BeMyHole il y a 3 ans

Fag Teaching

Transvids.tv il y a 5 mois

Submission training session for sweet brunette shemale

Submission training session for sweet brunette shemale

PornLib il y a 2 ans

Natalie Mars Training the baby Gimp 1

Natalie Mars Training the baby Gimp 1

ShemaleSin il y a 4 ans

Femboy instructing part 1: The Back Bend

Femboy instructing part 1: The Back Bend

Gay4Porn il y a 1 an

Cock Worship Boy Training

Cock Worship Boy Training

aShemaleTube il y a 3 ans

Sissy Training by Queen Daralis Part 2

52% HD 1:01 / 7:16

Sissy Training by Queen Daralis Part 2

FapHouse il y a 1 mois

Fag training Queen domina ??

Fag training Queen domina ??

Tranny.one il y a 1 an

Sissy tarts take hormones and tear up

Sissy tarts take hormones and tear up

TrannyGem il y a 3 ans

Every Country Has Sissy Maids

Every Country Has Sissy Maids

xHamster il y a 5 mois

IMMENSE DARK-HUED TRUNK PARENT USES CAGED YT SISSYBOY : your Black neighbor gets your sonny high and teaches him to conform

IMMENSE DARK-HUED TRUNK PARENT USES CAGED YT SISSYBOY : your Black neighbor gets your sonny high and teaches him to conform

2BGay il y a 2 ans

Sissy Training

xHamster il y a 1 an

Cum eating trainer video for the greedy sissy faggot whores

Cum eating trainer video for the greedy sissy faggot whores

Tranny.one il y a 3 ans

my idol best ever training

my idol best ever training

Tranny.one il y a 4 ans

Feminization Sissification Sissy training - BE ENSLAVED FAG

Feminization Sissification Sissy training - BE ENSLAVED FAG

TransTube.tv il y a 1 an

Trans Sissy Slut French Maid Service Training

Trans Sissy Slut French Maid Service Training

aShemaleTube il y a 4 mois

Sissy: A whore documentary

Sissy: A whore documentary

ShemaleSin il y a 1 mois

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lianna lawson and mistress robin coffins piggy princess training

TransDoe il y a 2 ans

Sissy Sub Instructing

Sissy Sub Instructing

TrannyGem il y a 9 mois

Sissy Whore Training

Sissy Whore Training

xHamster il y a 1 an

Crossdressing sissy nikki rails again

Crossdressing sissy nikki rails again

TrannyGem il y a 4 ans

Becoming Anal Slut Training For Newbies

Becoming Anal Slut Training For Newbies

BeMyHole il y a 3 ans

Sissy Fuckdoll Delivery

Sissy Fuckdoll Delivery

TransTube.tv il y a 9 mois

Sissy Dreams - 3 (eng)

Sissy Dreams - 3 (eng)

XXXShemalePorn il y a 11 ans

Kendall Penny New Orleans Gay Training

Kendall Penny New Orleans Gay Training

BeMyHole il y a 1 an

MistressAe Sessions with Princess Latex Rubber Doll: Impact & Spit Roast Training

66% HD 0:10 / 31:14

MistressAe Sessions with Princess Latex Rubber Doll: Impact & Spit Roast Training

LoyalFans il y a 2 mois

Sissy Fuckdoll Delivery

Sissy Fuckdoll Delivery

TrannyGem il y a 5 ans

Animate for training, learn to swallow yourself

Animate for training, learn to swallow yourself

aShemaleTube il y a 2 ans

Slutty Tranny Emily Adaire Is Fisted & DPed Anally in IR Gangbang 4K

Slutty Tranny Emily Adaire Is Fisted & DPed Anally in IR Gangbang 4K

AnySex il y a 1 an

Fag Instructing 8

Fag Instructing 8

TransTube.tv il y a 6 mois

Happy sissy perplexed by multiple sissygasms riding enormous 12.5”/32cm Yam-sized Father faux shaft

Happy sissy perplexed by multiple sissygasms riding enormous 12.5”/32cm Yam-sized Father faux shaft

Transvids.tv il y a 1 an

Riley wants you to play with her girl dick!

Riley wants you to play with her girl dick!

xHamster il y a 11 mois

Sissy Joyce guides you through the ultimate chastity cage experience - A Tranny's guide to domination and humiliation!

Sissy Joyce guides you through the ultimate chastity cage experience - A Tranny's guide to domination and humiliation!

TrannyMovs il y a 6 mois

White Guy University Lesson two

White Guy University Lesson two

UiPorn il y a 8 mois

Trannies in Training - EPISODE #01

Trannies in Training - EPISODE #01

Tranny.one il y a 3 ans

Sissy training: how to cum in chastity? Ride ever bigger dildos to sissygasm

Sissy training: how to cum in chastity? Ride ever bigger dildos to sissygasm

Pornvee il y a 4 mois

Anal Training That Will Make You Squirm

Anal Training That Will Make You Squirm

aShemaleTube il y a 5 ans

Training Cum Eating

Training Cum Eating

aShemaleTube il y a 1 an

Sissy Affirmations

Sissy Affirmations

ShemaleSin il y a 4 mois

2032 - the Bwno Future

2032 - the Bwno Future

xHamster il y a 6 mois

Fucking your trans best friend surprise

48% HD 1:01 / 9:35

Fucking your trans best friend surprise

FapHouse il y a 3 ans

Sissy Cum Swallow Training

Sissy Cum Swallow Training

Tranny.one il y a 4 ans

Lindsey Training Her Sissy Slave

Lindsey Training Her Sissy Slave

aShemaleTube il y a 1 an

Cum Dumpster Training

Cum Dumpster Training

aShemaleTube il y a 1 an

How to stick large toys up your butt & love it, a tutorial

How to stick large toys up your butt & love it, a tutorial

ShemaleSin il y a 4 ans

Feminization Sissification Sissy teaching - BE ENSLAVED HOMOSEXUAL

Feminization Sissification Sissy teaching - BE ENSLAVED HOMOSEXUAL

TrannyGem il y a 9 mois

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

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

xHamster il y a 1 an

Denim Girl

xHamster il y a 9 mois

Trained and Dominated TV & TS

Trained and Dominated TV & TS

Tranny.one il y a 4 ans

Slutty Sissy gets hard training Blowjob and Fuck Rough

Slutty Sissy gets hard training Blowjob and Fuck Rough

aShemaleTube il y a 1 mois

Petra's 8th training (incl 1st fist,massive sex toy and greater quantity)

Petra's 8th training (incl 1st fist,massive sex toy and greater quantity)

Amateur8 il y a 8 mois

Sissy training

Eporner il y a 11 mois

Trans Angel Stretched by Screwing Machine

Trans Angel Stretched by Screwing Machine

BigTitsLust il y a 1 an

Going Deep DEEP ft David Anderson

Going Deep DEEP ft David Anderson

xHamster il y a 2 ans

Sissy trainer: become slut like her

Sissy trainer: become slut like her

xHamster il y a 4 ans

Wild Sabrina Private Show

54% HD 2:00 / 16:26

Wild Sabrina Private Show

Flirt4Free il y a 6 ans

Sissy Fellates Alpha's Man rod And Takes A Filthy Facial cumshot While Domina Murmurs Encouragement

Sissy Fellates Alpha's Man rod And Takes A Filthy Facial cumshot While Domina Murmurs Encouragement

TransTube.tv il y a 9 mois

Jism countdown with TRANSSEXUAL PHAT ASS WHITE GIRL opening up her immense succulent caboose & cock-squeezing rosy crevice

Jism countdown with TRANSSEXUAL PHAT ASS WHITE GIRL opening up her immense succulent caboose & cock-squeezing rosy crevice

TrannyGem il y a 6 mois

Sissy Bride Getting Fucked by Her Doll

Sissy Bride Getting Fucked by Her Doll

xHamster il y a 6 mois

In Training With A Tran - Sinn Sage

In Training With A Tran - Sinn Sage

BeMyHole il y a 2 ans

Trained to Be a Submissive Slut

Trained to Be a Submissive Slut

aShemaleTube il y a 8 mois

having a fantastic sissy time

having a fantastic sissy time

TrannyGem il y a 1 an

W*A*A*A- 223 Masochistic Trans Boy and Lesbian Slut - Female Orgasmic Erotic Anal FUCK - Mao Hamasaki, Yui Hatano, Chibitori Decensored

W*A*A*A- 223 Masochistic Trans Boy and Lesbian Slut - Female Orgasmic Erotic Anal FUCK - Mao Hamasaki, Yui Hatano, Chibitori Decensored

Eporner il y a 7 mois

Kimber Haven BBC Sissy Training

Kimber Haven BBC Sissy Training

aShemaleTube il y a 5 ans

Guided Sissy JOI - Cock Sucking, Spit & CEI

Guided Sissy JOI - Cock Sucking, Spit & CEI

xHamster il y a 1 mois

Goddess Kyaa & River Enza in Gape Training 1

Goddess Kyaa & River Enza in Gape Training 1

Cremz il y a 5 ans

Lingerie Sissy Gets Locked Onto Her Dildo Pole and Tries to Cum in Chastity

Lingerie Sissy Gets Locked Onto Her Dildo Pole and Tries to Cum in Chastity

xHamster il y a 1 mois

Wife Trains Perfect Whore For Her Husband. Me, A Sissy.

Wife Trains Perfect Whore For Her Husband. Me, A Sissy.

AbTranny il y a 6 ans

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 il y a 10 mois

Natalie Mars Goddess Tangent - Training the Baby-Gimp [201

Natalie Mars Goddess Tangent - Training the Baby-Gimp [201

AbTranny il y a 2 ans

Gorgeous tgirl Angel dildo training 💋

Gorgeous tgirl Angel dildo training 💋

aShemaleTube il y a 1 an

Skitty in Anal Plug progression Stretching

Skitty in Anal Plug progression Stretching

xHamster il y a 3 ans

Mature Mistress teaches two sissies how to be good cocksuckers

Mature Mistress teaches two sissies how to be good cocksuckers

Tranny.one il y a 8 ans

Deep Anal Play & Sissygasms Creampie Jessica Bloom

Deep Anal Play & Sissygasms Creampie Jessica Bloom

xHamster il y a 4 ans

Matsumine Kohaku - Deepthroat Training! Massive Swallowing! A Perverted Circle Of Trans Lovers.

Matsumine Kohaku - Deepthroat Training! Massive Swallowing! A Perverted Circle Of Trans Lovers.

xHamster il y a 4 mois

Chatty Crossdresser chats again... and tries new plug 2023-02-26 part 1

Chatty Crossdresser chats again... and tries new plug 2023-02-26 part 1

xHamster il y a 3 ans

All that mouth training pays off : facefucking marvelous transwife Melody

All that mouth training pays off : facefucking marvelous transwife Melody

ShemaleSin il y a 1 an

Sissy Slut Training 3

Sissy Slut Training 3

xHamster il y a 11 mois

First-Ever time Sissy teaching KNUCKLE with forearms free-for-all climax!

First-Ever time Sissy teaching KNUCKLE with forearms free-for-all climax!

TrannyGem il y a 3 ans

Stretching and wrecking a femboy's asshole (full video on OF or Fansly)

Stretching and wrecking a femboy's asshole (full video on OF or Fansly)

xHamster il y a 2 ans

Neko Starlightfemboy Gape Training In Nylon Stockings

Neko Starlightfemboy Gape Training In Nylon Stockings

IcePorn il y a 2 semaines

Best of Harmony Rose vol 1

Best of Harmony Rose vol 1

xHamster il y a 11 mois

Femboy Viii punished

Femboy Viii punished

Transvids.tv il y a 10 mois

30 mins no break fellate spitroast contest!

30 mins no break fellate spitroast contest!

TrannyGem il y a 4 mois

Admit That You Are a Slut For My Cum

Admit That You Are a Slut For My Cum

xHamster il y a 1 an

Anal Trains: Me, My Friend and the Trans

Anal Trains: Me, My Friend and the Trans

xHamster il y a 2 mois

Nipple Pump Extreme Hardcore

Nipple Pump Extreme Hardcore

Tranny.one il y a 4 ans

Hard Anal Training for Lana Trap

Hard Anal Training for Lana Trap

Tranny.one il y a 4 ans

Trans Damsel takes Immense Trunk like a mega-cockslut.

Trans Damsel takes Immense Trunk like a mega-cockslut.

TransTube.tv il y a 1 an

TS Anna Katt Prepares Lily's Ass for Cock

TS Anna Katt Prepares Lily's Ass for Cock

TrannyGem il y a 6 ans

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