Sissy Orgasm Videos (43,645)

Alice Kizar Private Show

55% 4K 2:00 / 7:45

Alice Kizar Private Show

Flirt4Free 2 weeks ago

I Love This Hot Time

HD 2:00 / 16:10

I Love This Hot Time

Flirt4Free 3 years ago

Sissy Beauty Rod Milking Hands Free Anal With Cumplay And Cumswallow - Jessica Bloom

Sissy Beauty Rod Milking Hands Free Anal With Cumplay And Cumswallow - Jessica Bloom

ShemaleSin 2 years ago

Elix & Elias & Paulo Private Show

70% HD 2:00 / 4:57

Elix & Elias & Paulo Private Show

Flirt4Free 2 months ago

Ruined in urethral chastity

Ruined in urethral chastity

xHamster 3 years ago

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

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

xHamster 2 months ago

Restrained & Controlled - the *** Orgasm

Restrained & Controlled - the *** Orgasm

FapHouse 6 months ago

FEMDOM SISSY TRAINNING COMPILATION CUMSHOTS SISSYGASM

FEMDOM SISSY TRAINNING COMPILATION CUMSHOTS SISSYGASM

ShemaleSin 1 year ago

Sean Collinss Private Show

65% HD 2:00 / 31:00

Sean Collinss Private Show

Flirt4Free 1 week ago

trans slave teasing and nutting while sounding part three

trans slave teasing and nutting while sounding part three

TransTube.tv 1 year ago

77 cumshots compilation

51% HD 0:30 / 38:56

77 cumshots compilation

PornBox 2 years ago

Sissy Juliette gets machine banged to climax

Sissy Juliette gets machine banged to climax

ShemaleSin 2 years ago

Tranny got creampied by boyfriend

Tranny got creampied by boyfriend

xHamster 1 year ago

Nelly Gale Private Show

Nelly Gale Private Show

Flirt4Free 1 day ago

Trans Girl Sasha Q Cums BBC Dildo

Trans Girl Sasha Q Cums BBC Dildo

xHamster 1 week ago

Feelipe & Adara Private Show

72% HD 2:00 / 7:06

Feelipe & Adara Private Show

Flirt4Free 6 months ago

Gayest Cumshot Compilation Vol 2 (4k 60 Fps)

45% 4K 0:39 / 34:01

Gayest Cumshot Compilation Vol 2 (4k 60 Fps)

FapHouse 6 months ago

Master & Christian Mckenzie & Christian Rey Private Show

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 2 years ago

Gabriella Bruni Private Show

62% 4K 2:00 / 6:03

Gabriella Bruni Private Show

Flirt4Free 1 month ago

Double-sided dildo for cis girl's pussy and her tranny stepsister's ass

Double-sided dildo for cis girl's pussy and her tranny stepsister's ass

XGroovy 2 years ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 1 year ago

Horny Teen Playing with Lovense and Shaking Before Anal Orgasm Trans Porn Nbnabunny

HD 1:01 / 15:56

Horny Teen Playing with Lovense and Shaking Before Anal Orgasm Trans Porn Nbnabunny

FapHouse 1 year ago

Desire Sweet Private Show

HD 2:00 / 32:10

Desire Sweet Private Show

Flirt4Free 1 week ago

Aron & Master & Elvis Private Show

HD 2:00 / 21:26

Aron & Master & Elvis Private Show

Flirt4Free 3 years ago

Hardcore Throat and Ass Fucking: TS Gray Perrier Takes a Hardcore Pounding From Big Danny

HD 1:01 / 17:53

Hardcore Throat and Ass Fucking: TS Gray Perrier Takes a Hardcore Pounding From Big Danny

FapHouse 1 week ago

X-mas night with huge toys and fucking machine

X-mas night with huge toys and fucking machine

xHamster 1 year ago

Big CUMload riding BBC

Big CUMload riding BBC

xHamster 2 years ago

Elix & Elias & Paulo Private Show

46% HD 2:00 / 11:00

Elix & Elias & Paulo Private Show

Flirt4Free 5 months ago

Ladyboy Prostate Orgasm, Example 1

65% HD 0:39 / 16:04

Ladyboy Prostate Orgasm, Example 1

FapHouse 1 year ago

Taking My Horsie For Another Rail

Taking My Horsie For Another Rail

TrannyGem 1 year ago

POV-analsex with TS Emily - Naughty Trans Creampie

68% HD 1:01 / 14:00

POV-analsex with TS Emily - Naughty Trans Creampie

FapHouse 9 months ago

Mistress was merciful and feminized sissy in chastity cage got his ruined orgasms

Mistress was merciful and feminized sissy in chastity cage got his ruined orgasms

xHamster 9 months ago

Fat ejaculation

Fat ejaculation

TrannyGem 10 months ago

Leg Shaking Orgasm for Frankie Labido After Taking Dildo in Ass

Leg Shaking Orgasm for Frankie Labido After Taking Dildo in Ass

xHamster 1 year ago

Gothic French Sissy

Gothic French Sissy

xHamster 2 months ago

Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm

Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm

xHamster 1 year ago

Tatiana & Seline Private Show

Tatiana & Seline Private Show

Flirt4Free 2 years ago

Sissy PMV - Bitch

Sissy PMV - Bitch

Tranny.one 4 years ago

Milky TGirl in Chastity has Handsfree Sissygasm + Shows her Lactating Tits

Milky TGirl in Chastity has Handsfree Sissygasm + Shows her Lactating Tits

xHamster 5 months ago

The Futa Teacher FUTANARI HD

4K 0:12 / 21:52

The Futa Teacher FUTANARI HD

Clips4sale 2 years ago

Sissy Fuckdoll 2

Sissy Fuckdoll 2

xHamster 1 month ago

You want play with my girly dick? (Sissy, Femboy, Pov)

You want play with my girly dick? (Sissy, Femboy, Pov)

xHamster 4 years ago

Jessica Bloom Riding Monster Dildos Multiple Anal Orgasms in Chastity

Jessica Bloom Riding Monster Dildos Multiple Anal Orgasms in Chastity

xHamster 3 years ago

beautiful tgirl fucks ass and cums hard waiting for daddy

beautiful tgirl fucks ass and cums hard waiting for daddy

BallsAndBoobs 1 year ago

Emma Devereaux Private Show

Emma Devereaux Private Show

Flirt4Free 2 years ago

Hottest Ruined Cumming and Femdom Milking!

HD 0:39 / 14:33

Hottest Ruined Cumming and Femdom Milking!

FapHouse 2 years ago

Super-Naughty sissy Femboy gets romped ass-fuck by a Node Faux-Cock

Super-Naughty sissy Femboy gets romped ass-fuck by a Node Faux-Cock

TrannyGem 1 year ago

Big-titted Femdom Nyx Dominates in Lingerie & Stockings with Sissy BF's Cock Teased & Denied

Big-titted Femdom Nyx Dominates in Lingerie & Stockings with Sissy BF's Cock Teased & Denied

Jizzberry 4 years ago

Pop-Shot Compilation

Pop-Shot Compilation

4Gay 1 year ago

Camila & Samael Private Show

71% HD 2:00 / 22:30

Camila & Samael Private Show

Flirt4Free 6 months ago

Prostate toy into my rectal hole. High vigour stimulate to my prostate, I cum squirting female climax! Female mask cosplayer.

Prostate toy into my rectal hole. High vigour stimulate to my prostate, I cum squirting female climax! Female mask cosplayer.

ShemaleSin 3 weeks ago

Femboy Jizz Compilation 8

Femboy Jizz Compilation 8

TrannyGem 3 years ago

Jerk Off Instructions Real Futa Dragon Mom Instructs You How To Use A Pocket Cunny (Viii Stimulates / RedEyesBadDragon)

Jerk Off Instructions Real Futa Dragon Mom Instructs You How To Use A Pocket Cunny (Viii Stimulates / RedEyesBadDragon)

TrannyGem 3 years ago

Roy & Hercules & Jamer Private Show

44% HD 2:00 / 6:07

Roy & Hercules & Jamer Private Show

Flirt4Free 3 years ago

slutty winter girl with sexy over knee socks fuck her cream out with huge dildo

slutty winter girl with sexy over knee socks fuck her cream out with huge dildo

xHamster 3 years ago

Three Angles, One Moment of Pure Pleasure

Three Angles, One Moment of Pure Pleasure

xHamster 2 months ago

gangbang this asshole

63% HD 0:30 / 10:01

gangbang this asshole

PornBox 1 year ago

Wondrous TRANSSEXUAL Lucia Maya Boinks Her Bum With a Vibing Faux-Cock Until She Jizzes

Wondrous TRANSSEXUAL Lucia Maya Boinks Her Bum With a Vibing Faux-Cock Until She Jizzes

TrannyGem 4 years ago

Ruined orgasm in micro chastity cage with vibrator

Ruined orgasm in micro chastity cage with vibrator

xHamster 2 years ago

Orianna Dunn Private Show

57% HD 2:00 / 11:52

Orianna Dunn Private Show

Flirt4Free 1 year ago

Monica Farell Private Show

66% HD 2:00 / 18:40

Monica Farell Private Show

Flirt4Free 2 years ago

Feelipe & Adara Private Show

HD 2:00 / 25:52

Feelipe & Adara Private Show

Flirt4Free 5 months ago

Violetta R Private Show

Violetta R Private Show

Flirt4Free 1 year ago

Sissy Maid Cums & Squirts Hard from Anal Fucking Machine in Chastity Cage - Jessica Bloom

Sissy Maid Cums & Squirts Hard from Anal Fucking Machine in Chastity Cage - Jessica Bloom

xHamster 1 year ago

Big Bubble Butt Santa Gets Fucked By Big Sex Machine Dildo Until Having Prostate Orgasms For Christmas Present

Big Bubble Butt Santa Gets Fucked By Big Sex Machine Dildo Until Having Prostate Orgasms For Christmas Present

xHamster 1 month ago

Smash my caboose with my largest plaything & bang a fleshlight while railing

Smash my caboose with my largest plaything & bang a fleshlight while railing

TrannyGem 1 year ago

Best of Femdom Pegging! Strapon and Cum Compilation.

Best of Femdom Pegging! Strapon and Cum Compilation.

Pornzona 1 month ago

donk agonorgasmos Compilation

donk agonorgasmos Compilation

Transvids.tv 11 months ago

Caption - You Put a Camera in Your Femboy Friend's Room

69% HD 1:01 / 7:09

Caption - You Put a Camera in Your Femboy Friend's Room

FapHouse 1 year ago

Imposed Feminization and Double Domination

42% HD 0:30 / 58:28

Imposed Feminization and Double Domination

Clips4sale 1 year ago

男の娘がお尻をファックされて女みたいに喘いじゃう、、

男の娘がお尻をファックされて女みたいに喘いじゃう、、

GayCK 2 years ago

Girly Heather Ashley strips nude, cums from her huge girl dick

Girly Heather Ashley strips nude, cums from her huge girl dick

xHamster 4 weeks ago

Sophia Loreen Private Show

56% 4K 2:00 / 7:57

Sophia Loreen Private Show

Flirt4Free 3 months ago

Body Stockings in the Bedroom with High Heels Panties and Rings

Body Stockings in the Bedroom with High Heels Panties and Rings

xHamster 2 years ago

Santiago & Joseph Private Show

61% HD 2:00 / 24:52

Santiago & Joseph Private Show

Flirt4Free 1 year ago

Wifey Taunts you about locking you in innocence like her TRANSSEXUAL Buddy POINT OF VIEW HAND JOB SISSY TEACHING

Wifey Taunts you about locking you in innocence like her TRANSSEXUAL Buddy POINT OF VIEW HAND JOB SISSY TEACHING

TrannyGem 4 years ago

RUIN IT and EAT IT off my SOCKS SLUT!

RUIN IT and EAT IT off my SOCKS SLUT!

Pornzona 2 weeks ago

Liam Jacobson Private Show

HD 2:00 / 12:37

Liam Jacobson Private Show

Flirt4Free 1 month ago

Femboy POV Cum Compilation

Femboy POV Cum Compilation

xHamster 4 years ago

Assorted glamour movies of Sissy orgasming with just puffies【nohand 乳首射精女装男子 femboy】

Assorted glamour movies of Sissy orgasming with just puffies【nohand 乳首射精女装男子 femboy】

5Gays 3 months ago

Massive ejaculation by inserting electric massage machine into anal

Massive ejaculation by inserting electric massage machine into anal

TrannyGem 3 years ago

Dimitri Caruso Private Show

4K 2:00 / 11:17

Dimitri Caruso Private Show

Flirt4Free 1 year ago

William Raven Private Show

HD 2:00 / 13:16

William Raven Private Show

Flirt4Free 4 years ago

Phat ass femboy uses his entire toy collection in order to cum

Phat ass femboy uses his entire toy collection in order to cum

XGroovy 1 year ago

trans sissy fleshlight banging multiple climax compilation (preview!)

trans sissy fleshlight banging multiple climax compilation (preview!)

Amateur8 4 years ago

Femboy Whips Out Red-Hot Jizm on Face

Femboy Whips Out Red-Hot Jizm on Face

GayCK 4 years ago

How to get Multiple Sissy Climax during Anal Training? Sissy Princess Veronica will show

How to get Multiple Sissy Climax during Anal Training? Sissy Princess Veronica will show

ShemaleSin 1 year ago

Just a horny day and sissy driving huge toys in her pussy, double penetration, fisting

Just a horny day and sissy driving huge toys in her pussy, double penetration, fisting

xHamster 1 year ago

Domme girl pounds ladyboy sissy mega-bitch EJACULATION ASSFUCK

Domme girl pounds ladyboy sissy mega-bitch EJACULATION ASSFUCK

Transvids.tv 6 months ago

Roy is a the Best Bottom

50% HD 2:00 / 9:57

Roy is a the Best Bottom

Flirt4Free 3 years ago

Very First BIG BLACK COCK Practice

Very First BIG BLACK COCK Practice

TrannyGem 2 years ago

Sissy Panties, CBT and hard estim. Hands free orgasm.

Sissy Panties, CBT and hard estim. Hands free orgasm.

xHamster 2 years ago

Milk or Tea?

xHamster 1 month ago

Sissy crossdresser luvs getting ravaged

Sissy crossdresser luvs getting ravaged

4Gay 6 months ago

Elvis & Alfonso & Master Private Show

Elvis & Alfonso & Master Private Show

Flirt4Free 3 years ago

Huge Cumshot Compilation

Huge Cumshot Compilation

Tranny.one 4 years ago

Ultimate compilation of prostate orgasms: a collection of personal moments

Ultimate compilation of prostate orgasms: a collection of personal moments

XXXShemalePorn 1 month ago

Lust Academy: Sadira and James' Join Handjob Journey - Shemale Version

Lust Academy: Sadira and James' Join Handjob Journey - Shemale Version

xHamster 4 weeks ago

"She's coming in her pants - and I'm filming everything POV German"

"She's coming in her pants - and I'm filming everything POV German"

xHamster 8 months ago

He Wanted Me to Spank the Ass (valeria Toro)

He Wanted Me to Spank the Ass (valeria Toro)

xHamster 2 months ago

Glasses Babe Jerks Huge Shemale Cock

Glasses Babe Jerks Huge Shemale Cock

SleazyNEasy 1 week ago

Solo Sissy Orgasm

Solo Sissy Orgasm

xHamster 4 days ago

Jaq Quicksilver First-Ever Pound Machine with Knotty Bad Dragon to Solo Ejaculation

Jaq Quicksilver First-Ever Pound Machine with Knotty Bad Dragon to Solo Ejaculation

TrannyGem 2 years ago

Young Femboy Cums Through Sissy Lingerie Bodysuit While Riding Fat Cock Cumshit

Young Femboy Cums Through Sissy Lingerie Bodysuit While Riding Fat Cock Cumshit

xHamster 1 year ago

Sissy Slut Bess repeatedly interrupted trying to cum in her car

Sissy Slut Bess repeatedly interrupted trying to cum in her car

xHamster 3 years ago

IDidNotNoticeDadWatchingMewhileImHavingFun

IDidNotNoticeDadWatchingMewhileImHavingFun

TrannyGem 6 months ago

Great girl-girl show for her master! Jerk off challenge for two hot tranny girlies!

Great girl-girl show for her master! Jerk off challenge for two hot tranny girlies!

xHamster 1 year ago

Josie Blade^’s first time solo in the mini pool

Josie Blade^’s first time solo in the mini pool

xHamster 3 years ago

TGirl in Chastity with Lactating Tits has Anal Orgasm Hands Free Sissygasm

TGirl in Chastity with Lactating Tits has Anal Orgasm Hands Free Sissygasm

xHamster 8 months ago

Slobbery Suck Fingers

Slobbery Suck Fingers

Flirt4Free 9 months ago

Hands free cum compilation

Hands free cum compilation

aShemaleTube 3 years ago

Cute Succubus Wants to Take All Your Cum This Halloween

57% HD 0:39 / 22:08

Cute Succubus Wants to Take All Your Cum This Halloween

FapHouse 2 years ago

Perfectly clean ass transvestite

Perfectly clean ass transvestite

xHamster 1 year ago

Asian Crossdresser femboy cumshot complication (2 videos mix)

Asian Crossdresser femboy cumshot complication (2 videos mix)

xHamster 1 year ago

Dildo Prostate Orgasm During Shower in Parents Bathroom

Dildo Prostate Orgasm During Shower in Parents Bathroom

FapHouse 2 weeks ago

My sissyboy gets three ruined orgasms in a row. No real orgasm for boys in lace panties! Femdom and feminization

My sissyboy gets three ruined orgasms in a row. No real orgasm for boys in lace panties! Femdom and feminization

xHamster 1 year ago

Justin Evanss Private Show

HD 2:00 / 13:53

Justin Evanss Private Show

Flirt4Free 2 weeks ago

teenie crossdresser chinese t-model in stilettos fapping off here lollipop for joy

teenie crossdresser chinese t-model in stilettos fapping off here lollipop for joy

TrannyGem 3 years ago

Mega Cumshot Compilation Number Two 50 Plus Cum Squirts

Mega Cumshot Compilation Number Two 50 Plus Cum Squirts

xHamster 3 months ago

I wanna be a NICE GAL and take it all!

I wanna be a NICE GAL and take it all!

ShemaleSin 2 weeks ago

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