Femboy Training Videos 18+ (10,986)

Sissy Training Encouragement Crossdresser BBC Anal Fiona Fortune

Sissy Training Encouragement Crossdresser BBC Anal Fiona Fortune

AShemaleTube 9 months ago

Sissy gothic cow with red hair and in chastity rides a big black dildo on her pillow

Sissy gothic cow with red hair and in chastity rides a big black dildo on her pillow

XHamster 10 months ago

Xxl Dildo Training Mr Hankey Toys, Greedy Cluster, Topped Toys, Kink3d and Kink_wear

Xxl Dildo Training Mr Hankey Toys, Greedy Cluster, Topped Toys, Kink3d and Kink_wear

XHamster 6 months ago

I Turn My Slave Into a Sissy Slut and Make Him Suck a Dildo, Mf

55% HD 1:01 / 11:06

I Turn My Slave Into a Sissy Slut and Make Him Suck a Dildo, Mf

FapHouse 2 weeks ago

Crossdressing in Order to Be Hired for Maid Position (full Movie)

Crossdressing in Order to Be Hired for Maid Position (full Movie)

XHamster 2 months ago

She-creature oral jobs the jizz out of GINORMOUS DARK-HUED MAN SAUSAGE

She-creature oral jobs the jizz out of GINORMOUS DARK-HUED MAN SAUSAGE

TransTube.tv 1 year ago

Trans gf Daniela Chanel penetrates my taut crevice with her phat girlcock.

Trans gf Daniela Chanel penetrates my taut crevice with her phat girlcock.

TrannyGem 1 year ago

Becoming Her

XHamster 4 months ago

Slut eats cum from condom

Slut eats cum from condom

AShemaleTube 9 months ago

Sissy instructing - Enjoy For Assfucking Fucky-fucky

Sissy instructing - Enjoy For Assfucking Fucky-fucky

TransTube.tv 1 year ago

BBC Training with Cerjoy

56% HD 0:39 / 32:46

BBC Training with Cerjoy

FapHouse 10 months ago

Asian Beauty in College Uniform Squirts While Training Her Anal by Pushing a Huge Anal Plug Out

67% HD 0:39 / 7:47

Asian Beauty in College Uniform Squirts While Training Her Anal by Pushing a Huge Anal Plug Out

FapHouse 6 months ago

Anal Training Night

Anal Training Night

XHamster 1 year ago

Dildo Riding Time

Dildo Riding Time

FapHouse 5 months ago

Sexy Femboy in Pink Latex

63% 0:39 / 1:25

Sexy Femboy in Pink Latex

FapHouse 1 month ago

Balls and Bat in My Stretched Ass, Anal Gape and Huge Cumshot

66% HD 1:01 / 15:07

Balls and Bat in My Stretched Ass, Anal Gape and Huge Cumshot

FapHouse 4 weeks ago

Emo Sissy Smoking Fetish & Solo Dance — POINT OF VIEW Crossdresser in Pantyhose

Emo Sissy Smoking Fetish & Solo Dance — POINT OF VIEW Crossdresser in Pantyhose

Gayhub 8 months 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

Pretty Trans Girl Throat Fucked by Tattooed Muscle Stud

69% HD 0:39 / 7:36

Pretty Trans Girl Throat Fucked by Tattooed Muscle Stud

FapHouse 6 months ago

White trans femboy gargle jack and smooch huge monster big black cock suck off energetically

White trans femboy gargle jack and smooch huge monster big black cock suck off energetically

4Gay 1 year ago

Baseball Training

60% 0:39 / 12:03

Baseball Training

FapHouse 3 months ago

Sissy Slut Gangbang Training

Sissy Slut Gangbang Training

XHamster 2 weeks ago

Best transsexual cum compilation

Best transsexual cum compilation

AnySex 3 years ago

Joven Ladyboy Tiene Orgasmo Analyoung Ladyboy Has a Sissygasm

Joven Ladyboy Tiene Orgasmo Analyoung Ladyboy Has a Sissygasm

XHamster 8 months ago

SIssy Mega-slut Lola Crystals gets predominated and creampied two times by BIG BLACK COCK

SIssy Mega-slut Lola Crystals gets predominated and creampied two times by BIG BLACK COCK

Transvids.tv 1 year ago

Gorgeous Puppygirl Nyxi Leon Trained & Fucked by Daddy Doggystyle and Reverse Cowgirl

63% HD 0:39 / 27:09

Gorgeous Puppygirl Nyxi Leon Trained & Fucked by Daddy Doggystyle and Reverse Cowgirl

FapHouse 8 months ago

Quick Anal Session

Quick Anal Session

XHamster 2 months ago

Trans Gwen Tennyson in High Heels Massive Anal Creampie Cumfarts and Wedgie Anal Sex through her Torn Leggings

Trans Gwen Tennyson in High Heels Massive Anal Creampie Cumfarts and Wedgie Anal Sex through her Torn Leggings

XHamster 3 weeks ago

Big Tits Shemale Gwen Tennyson Lactating Her Nipples with Vacuum Milking Machine

Big Tits Shemale Gwen Tennyson Lactating Her Nipples with Vacuum Milking Machine

XHamster 6 months ago

Sissy Trainer - Sissy - Feminization - Sissification

Sissy Trainer - Sissy - Feminization - Sissification

TrannyGem 3 years ago

Anal Training 104

58% HD 0:39 / 27:17

Anal Training 104

FapHouse 3 weeks ago

korean femboy kimono smashed

korean femboy kimono smashed

Gay4Porn 1 year ago

Sissy attempts anal invasion on a park bench

Sissy attempts anal invasion on a park bench

Gayhub 6 days ago

Domina gives me box's key to cum as a woman after 6 days on innocence

Domina gives me box's key to cum as a woman after 6 days on innocence

Transvids.tv 1 year ago

Tranny Gwen Tennyson Destroying Her Ass with BBC Fat Dildo for the First Time (round 1)

Tranny Gwen Tennyson Destroying Her Ass with BBC Fat Dildo for the First Time (round 1)

XHamster 3 weeks ago

Unexpected sissy boy orgasm .

Unexpected sissy boy orgasm .

XHamster 4 months ago

Pornstar Ria Bentley Takes Giant BBC On Public Hotel Balcony

Pornstar Ria Bentley Takes Giant BBC On Public Hotel Balcony

XHamster 1 year ago

Trans Girl Fucks a Pumpkin

Trans Girl Fucks a Pumpkin

XHamster 4 months ago

Ria Bentley Succumbs to Raw Anal by Gigantic BBC

63% HD 1:01 / 14:46

Ria Bentley Succumbs to Raw Anal by Gigantic BBC

FapHouse 1 year ago

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

XHamster 1 year ago

Special Fat Ass Emo Femboy Cumfarting Anal Creampie After Being Gaped and Fucked by Black Dildo

65% HD 0:39 / 31:45

Special Fat Ass Emo Femboy Cumfarting Anal Creampie After Being Gaped and Fucked by Black Dildo

FapHouse 1 month ago

51cm John Thomas Henry Humungous Assfuck Destruction Fuck Stick Slamming Deep into Slick Nice Femboy Asspussy

51cm John Thomas Henry Humungous Assfuck Destruction Fuck Stick Slamming Deep into Slick Nice Femboy Asspussy

TrannyGem 2 years ago

Lucky Big Ass Sissy Slut Fucked by Mistress Jenna Until He Cums Over Her Fat Strapon Cock!

Lucky Big Ass Sissy Slut Fucked by Mistress Jenna Until He Cums Over Her Fat Strapon Cock!

XHamster 1 year ago

Small Dick Gothic Trans in Raven Cosplay Anal Pissing after Riding Big Black Dildo and getting Creampie

Small Dick Gothic Trans in Raven Cosplay Anal Pissing after Riding Big Black Dildo and getting Creampie

XHamster 2 weeks ago

FIRST-TIMER CROSSDRESSERS EXPERIENCE STRONG SOLO GETTING OFF CRAVINGS

FIRST-TIMER CROSSDRESSERS EXPERIENCE STRONG SOLO GETTING OFF CRAVINGS

Gayhub 18 hours ago

Enormous Compilation Concerning Butthole Cumming And Solo Cumshots Collection sissygasm ( trap milking )

Enormous Compilation Concerning Butthole Cumming And Solo Cumshots Collection sissygasm ( trap milking )

KAMS 1 year ago

POINT OF VIEW-Trans gf attempts to get him to stop dinking around with her girlfriend- fellatio and pummeled

POINT OF VIEW-Trans gf attempts to get him to stop dinking around with her girlfriend- fellatio and pummeled

TransTube.tv 1 year ago

He fucks me like a bitch... I love being trained by Master - @AxelReigns & @Sasha_de_Sade on OF ;)

He fucks me like a bitch... I love being trained by Master - @AxelReigns & @Sasha_de_Sade on OF ;)

MyTransfix 5 days ago

Sissy Slut Anal Destruction

49% HD 1:01 / 19:58

Sissy Slut Anal Destruction

FapHouse 1 year ago

Dildo Fuck Boy Ass

47% HD 0:39 / 4:22

Dildo Fuck Boy Ass

FapHouse 1 week ago

Sissy very first vid

Sissy very first vid

TrannyGem 2 years ago

Feminized she-male gets cooter penetrated

Feminized she-male gets cooter penetrated

TrannyGem 1 year ago

Iskra Sissy Crossdresser

Iskra Sissy Crossdresser

TrannyGem 2 years ago

Twinkerbell Pegging the Lost Femboi in Chastity

Twinkerbell Pegging the Lost Femboi in Chastity

XHamster 1 year ago

Trans Physical Therapist Ria Bentley Works Wonders On BBC Patient

Trans Physical Therapist Ria Bentley Works Wonders On BBC Patient

XHamster 1 year ago

Sissy squirts from her caged clit while riding her BBC dildo

Sissy squirts from her caged clit while riding her BBC dildo

XHamster 1 year ago

Anal slut prolapse on inflatable butt plug

Anal slut prolapse on inflatable butt plug

XHamster 6 months ago

Tiny Clitty on the Beach

56% 0:39 / 1:20

Tiny Clitty on the Beach

FapHouse 2 months ago

Asian Beauty in College Uniform Squirts While Training Her Anal by Pushing a Huge Anal Plug Out

72% HD 0:39 / 7:47

Asian Beauty in College Uniform Squirts While Training Her Anal by Pushing a Huge Anal Plug Out

FapHouse 6 months ago

My Ass is My Pussy

My Ass is My Pussy

XHamster 11 months ago

Cum in Her Own Mouth After Sissygasm

Cum in Her Own Mouth After Sissygasm

XHamster 1 month ago

Teen femboy in chastity thong takes massive vibrator unfathomable in her taut delicate butt extraordinary anal training

Teen femboy in chastity thong takes massive vibrator unfathomable in her taut delicate butt extraordinary anal training

ShemaleSin 2 weeks ago

Huge Ass Shemale Caulifla Ssj Massive Anal Creampies and Cumfarts After Being Fucked by Big Dildo

Huge Ass Shemale Caulifla Ssj Massive Anal Creampies and Cumfarts After Being Fucked by Big Dildo

XHamster 1 month ago

G093 - Clean Loads Dumped in Femme 12

57% HD 0:39 / 17:09

G093 - Clean Loads Dumped in Femme 12

FapHouse 7 months ago

Sissy bitch boi Jes Brinch

Sissy bitch boi Jes Brinch

XHamster 4 months ago

Trans Sissy French Maid Service Training

Premium HD 26:33

Trans Sissy French Maid Service Training

XNXXGold 9 months ago

Ahegao Femboy Ben Tennyson Pumping Her Bimbo Lips with Vacuum Machine in Sissyfication and Feminization Program

Ahegao Femboy Ben Tennyson Pumping Her Bimbo Lips with Vacuum Machine in Sissyfication and Feminization Program

XHamster 3 weeks ago

Dildo Cums Inside My Ass

68% 0:39 / 2:24

Dildo Cums Inside My Ass

FapHouse 11 months ago

Cristal Kinky Anal Training Sissy

55% HD 1:01 / 32:19

Cristal Kinky Anal Training Sissy

FapHouse 1 month ago

Femboy Close up Pussy Training with Dildo with Farting and Gaping

HD 1:01 / 31:00

Femboy Close up Pussy Training with Dildo with Farting and Gaping

FapHouse 1 year ago

TRANSSEXUAL Willow Hammerz - BNWO Sissy PMV

TRANSSEXUAL Willow Hammerz - BNWO Sissy PMV

TrannyGem 10 months ago

Every day life of compliant femboy sissy simran as a ideal crossdress bimbo twink

Every day life of compliant femboy sissy simran as a ideal crossdress bimbo twink

ShemaleSin 1 month ago

CEI Sissy Training - Hentai Tranced JOI

CEI Sissy Training - Hentai Tranced JOI

HentaiGem 1 year ago

I Cumming on the Top!!!! Free Hands Sissygasm

I Cumming on the Top!!!! Free Hands Sissygasm

FapHouse 1 month ago

POV Sissy Fisting

64% 0:39 / 8:16

POV Sissy Fisting

FapHouse 2 months ago

Femboy dominates & TALKS DIRTY (Sissy Training JOI)

Femboy dominates & TALKS DIRTY (Sissy Training JOI)

Tranny.one 4 years ago

Self Facial Cumshot spunking from super-steamy sissy

Self Facial Cumshot spunking from super-steamy sissy

TrannyGem 3 years ago

Anal Training #14 Tanned Femboy Fucks Himself in the Ass and Cums

HD 1:01 / 39:01

Anal Training #14 Tanned Femboy Fucks Himself in the Ass and Cums

FapHouse 1 year ago

Doggy style sissy training in a red dress and white pumps

Doggy style sissy training in a red dress and white pumps

XHamster 2 years ago

Femboy stretches his hole with a big dildo

Femboy stretches his hole with a big dildo

XHamster 4 years ago

SISSY ass fuck until he CUM in my mouth

SISSY ass fuck until he CUM in my mouth

XHamster 3 years ago

Female Dom Gf Won’t let me take out speculum till she’s creampied trans jism bi-racial big black cock femboy

Female Dom Gf Won’t let me take out speculum till she’s creampied trans jism bi-racial big black cock femboy

TrannyGem 3 years ago

Lick up Every Drop of Pre-cum! Only Then Can You Cum on My Jeans Ass! JOI CEI German

46% HD 0:39 / 9:10

Lick up Every Drop of Pre-cum! Only Then Can You Cum on My Jeans Ass! JOI CEI German

FapHouse 6 months ago

Transformation from a regular boy into a insatiable sissy romp fuckslut that can be used firm sans grace.

Transformation from a regular boy into a insatiable sissy romp fuckslut that can be used firm sans grace.

TrannyGem 1 year ago

Anal Orgasm, Cumshots in My Mouth, Compilation of My Hot Cumshots

68% HD 0:39 / 5:50

Anal Orgasm, Cumshots in My Mouth, Compilation of My Hot Cumshots

FapHouse 6 months ago

Crossdressing gay torn up in the bootie

Crossdressing gay torn up in the bootie

TrannyGem 1 year ago

Joanna's Softcore Dance Live Fetish Corset Leather trousers Sissy Biotch Gimp

Joanna's Softcore Dance Live Fetish Corset Leather trousers Sissy Biotch Gimp

TrannyGem 2 years ago

ts ria bentley gets pegged and pissed on by gothess bri

ts ria bentley gets pegged and pissed on by gothess bri

PissVids 2 years ago

Sissy Kanisa Anal Training: Eggs Injection Anal Plugged and Cock Caged

Sissy Kanisa Anal Training: Eggs Injection Anal Plugged and Cock Caged

FapHouse 2 months ago

Hooded Sissy booty traes from behind

Hooded Sissy booty traes from behind

Gayhub 1 year ago

Sub Fan Worships My Sweaty Armpits and Takes My Load Deep

53% HD 0:39 / 33:41

Sub Fan Worships My Sweaty Armpits and Takes My Load Deep

FapHouse 11 months ago

Boy with Taboo Desires! - Full Movie (anal, Cumshots, Fucking, Chubby, Blonde)

55% HD 1:01 / 53:18

Boy with Taboo Desires! - Full Movie (anal, Cumshots, Fucking, Chubby, Blonde)

FapHouse 1 year ago

Sissy Training by Queen Daralis Part 3

Sissy Training by Queen Daralis Part 3

FapHouse 6 months ago

Extended Cut of BBC Dildo Impregnating and Opening My Big Fat Trans Ass

Extended Cut of BBC Dildo Impregnating and Opening My Big Fat Trans Ass

FapHouse 10 months ago

Trans Gwen Tennyson Extreme Massive Anal Creampies and Cumfarts After Being Ass Fucked with Inflatable Dildo

Trans Gwen Tennyson Extreme Massive Anal Creampies and Cumfarts After Being Ass Fucked with Inflatable Dildo

XHamster 1 month ago

I'm a woman, who wants to open me up

I'm a woman, who wants to open me up

XHamster 6 months ago

Sissy Cock Sock: GAY Training Mind Fuck

62% HD 0:25 / 9:17

Sissy Cock Sock: GAY Training Mind Fuck

IWantClips 1 year ago

Lexia Lynx - Pent Up - Glad Fuckslut Feminization Affirmations & Sissy Teaching (Captions)

Lexia Lynx - Pent Up - Glad Fuckslut Feminization Affirmations & Sissy Teaching (Captions)

TrannyGem 1 year ago

Hot shemale in mask gives BBC best blowjob ever

Hot shemale in mask gives BBC best blowjob ever

MyLust 1 year ago

Sissy Shiera Demonstrates Off Her Gams

Sissy Shiera Demonstrates Off Her Gams

Gayhub 4 weeks ago

Cute Femboy Jessica Bloom's 1st Brilliance Gap Visit - Swallows Cum In Throat!

Cute Femboy Jessica Bloom's 1st Brilliance Gap Visit - Swallows Cum In Throat!

ShemaleSin 6 months ago

BIG BLACK COCK Neighbor Back For More Dirty Head From Pretty Trans Woman

BIG BLACK COCK Neighbor Back For More Dirty Head From Pretty Trans Woman

Transvids.tv 1 year ago

Smallish Chinese Femboy Gimp Groans While Getting Drilled by Warm Trans

Smallish Chinese Femboy Gimp Groans While Getting Drilled by Warm Trans

Transvids.tv 1 year ago

BBC Dildo Solo Ass Fuck

BBC Dildo Solo Ass Fuck

FapHouse 3 days ago

Femboy Sounding in Chastity

Femboy Sounding in Chastity

FapHouse 2 years ago

At Her Mercy: Hot Trans Domme Trains You

47% HD 1:01 / 52:40

At Her Mercy: Hot Trans Domme Trains You

FapHouse 1 year ago

Sissy Juvia does some encouraging Sissyfication Training JOI

Sissy Juvia does some encouraging Sissyfication Training JOI

XHamster 3 years ago

Meet Nikki the Cute Femboy. Tiny Dick Bubble Butt BBC Wild Ride

44% HD 0:39 / 4:03

Meet Nikki the Cute Femboy. Tiny Dick Bubble Butt BBC Wild Ride

FapHouse 4 months ago

Big Ass Trans Raven Anal Creampie and Fucked Doggystyle by Inflatable Dildo

Big Ass Trans Raven Anal Creampie and Fucked Doggystyle by Inflatable Dildo

XHamster 2 months ago

Sissy cums in chastity and licks it all up

Sissy cums in chastity and licks it all up

XHamster 1 year ago

Kitty training her ass💗

Kitty training her ass💗

AShemaleTube 1 year ago

Femboy Anal Training

Femboy Anal Training

FapHouse 3 months ago

Sissy Training by Queen Daralis Part 5

57% HD 0:39 / 4:59

Sissy Training by Queen Daralis Part 5

FapHouse 6 months ago

Sissy femboy makes chastity content and streams on chaturbate

Sissy femboy makes chastity content and streams on chaturbate

ShemaleSin 1 year ago

Big Tits Shemale Gwen Tennyson Lactating Her Nipples with Vacuum Milking Machine

Big Tits Shemale Gwen Tennyson Lactating Her Nipples with Vacuum Milking Machine

XHamster 5 months ago

Femboy vs Penetrate-machine

Femboy vs Penetrate-machine

4Gay 5 months ago

This Video Is the 1st in a Series of Nyxi Leon's Very First Transformation Ever

45% HD 0:39 / 25:41

This Video Is the 1st in a Series of Nyxi Leon's Very First Transformation Ever

FapHouse 1 year ago

Sissy Training

XHamster 1 year ago

Sissy Kaluna deep-throats BIG BLACK COCK

Sissy Kaluna deep-throats BIG BLACK COCK

TrannyGem 4 years ago

116 min degrading of bdsm sissy pain whore Alina

116 min degrading of bdsm sissy pain whore Alina

XHamster 1 year ago

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