Prostate Orgasm Videos - Trans (4,142)

Amateur Crossdressers' Anal Orgasm Webcam Session

Amateur Crossdressers' Anal Orgasm Webcam Session

SEXTVX 4 months ago

Curious Bi Boy Experiences His First Anal Orgasm with Older Boyfriend Submissive Prostate Orgasm Gay Sex

Premium HD 4:39

Curious Bi Boy Experiences His First Anal Orgasm with Older Boyfriend Submissive Prostate Orgasm Gay Sex

Sheer 7 months ago

Prostate orgasms cumpilation. Personalsin collection vol. 104

Prostate orgasms cumpilation. Personalsin collection vol. 104

ShemaleSin 4 years ago

Draining my Sissy Balls With Multiple Dildos - Jessica Bloom

Draining my Sissy Balls With Multiple Dildos - Jessica Bloom

xHamster 4 years ago

Compilations

xHamster 4 years ago

Femboy Rails Firm And Drills An Arse With A Ginormous Fake Penis And Gets An Ass Fucking Ejaculation

Femboy Rails Firm And Drills An Arse With A Ginormous Fake Penis And Gets An Ass Fucking Ejaculation

TrannyGem 3 years ago

Sayuki Solo Prostate Vibrator

Sayuki Solo Prostate Vibrator

xHamster 3 years ago

Twink boy rides dildo until cumming hands free.

Twink boy rides dildo until cumming hands free.

xHamster 3 years ago

Latin teen trap ride her dildo

Latin teen trap ride her dildo

xHamster 3 years ago

My Hands Free Prostate Orgasm

My Hands Free Prostate Orgasm

FapHouse 1 year ago

Natural lubricant

Natural lubricant

ShemaleSin 1 year ago

Ass Fucking orgam

Ass Fucking orgam

TrannyGem 1 year ago

Indian Male to take a break to take it out and my calendar so and my own and my mom and my own and get the

Indian Male to take a break to take it out and my calendar so and my own and my mom and my own and get the

xHamster 2 years ago

Prostate orgasms compilation. Personalsin collection vol. 40

Prostate orgasms compilation. Personalsin collection vol. 40

ShemaleSin 1 year ago

Prostate orgasms cumpilation. Personalsin collection vol. 123

Prostate orgasms cumpilation. Personalsin collection vol. 123

ShemaleSin 1 year ago

Mature Sissy CD Teacher Playing with Herself to an Orgasm Shoving a Screwdriver Handle in Butt

Mature Sissy CD Teacher Playing with Herself to an Orgasm Shoving a Screwdriver Handle in Butt

FapHouse 1 year ago

Crossdresser in Fishnet Body, train his Anal pussy the max

Crossdresser in Fishnet Body, train his Anal pussy the max

xHamster 1 year ago

Transgender pounds her prostate for a sissygasm orgasm

Transgender pounds her prostate for a sissygasm orgasm

TubeOn 1 year ago

Sissy hunk squirting from BBC

Sissy hunk squirting from BBC

ShemaleSin 1 year ago

Compilation of prostate orgasms volume 140

Compilation of prostate orgasms volume 140

XXXShemalePorn 1 year ago

Transgender pounds her prostate for a sissygasm orgasm

Transgender pounds her prostate for a sissygasm orgasm

Love4Porn 1 year ago

74044487 prostate orgasms cumpilation personalsin colle

74044487 prostate orgasms cumpilation personalsin colle

Sheshaft 1 year ago

emilestonecd sissy prostate milking 4

emilestonecd sissy prostate milking 4

GayCK 1 year ago

Prostate orgasms compilation. Personalsin collection vol. 72

Prostate orgasms compilation. Personalsin collection vol. 72

ShemaleSin 1 year ago

Cumming Into My Own Throat Via Anal Climax - Jessica Bloom Large Rod Sissy

Cumming Into My Own Throat Via Anal Climax - Jessica Bloom Large Rod Sissy

ShemaleSin 1 year ago

Chastity Sissy Slut Anal Orgasm Encouragement - Jessica Bloom

Premium 57% HD 38:01

Chastity Sissy Slut Anal Orgasm Encouragement - Jessica Bloom

XVideosRed 1 year ago

Prostate orgasms cumpilation. Personalsin collection vol.104

Prostate orgasms cumpilation. Personalsin collection vol.104

ShemaleSin 1 year ago

Amazing Prostate Orgasms Cumshots Compilation K

Amazing Prostate Orgasms Cumshots Compilation K

AbTranny 2 years ago

Compilation of prostate orgasms in personal collection volume

Compilation of prostate orgasms in personal collection volume

XXXShemalePorn 1 year ago

Jessica Bloom vs Funzze Sex Toy - Massive Sissy Jizz Flow

Jessica Bloom vs Funzze Sex Toy - Massive Sissy Jizz Flow

ShemaleSin 1 year ago

SometimesNiki riding with new boobs

SometimesNiki riding with new boobs

xHamster 2 years ago

Hands free prostate orgasm

Hands free prostate orgasm

FapHouse 2 years ago

Squirting Chain And Orgasmic Big Dick In Insolence.

Squirting Chain And Orgasmic Big Dick In Insolence.

xHamster 2 years ago

Anal CD milking with glass of cum

Anal CD milking with glass of cum

XXXShemalePorn 2 years ago

masturbating like a dog

masturbating like a dog

xHamster 3 years ago

Donkey Dildo Makes me Sissygasm Hard Shemale Anal Orgasms &amp_ Prostate Milking (Full)

Premium HD 12:32

Donkey Dildo Makes me Sissygasm Hard Shemale Anal Orgasms &amp_ Prostate Milking (Full)

XVideosRed 2 years ago

Femboy gets an ass fucking climax and kneads a rock-hard schlong ( sissy trap jism )

Femboy gets an ass fucking climax and kneads a rock-hard schlong ( sissy trap jism )

TrannyGem 2 years ago

Prostate Massage and Cumshot for Trans Girl on the Medical Chair

Prostate Massage and Cumshot for Trans Girl on the Medical Chair

Clips4sale 2 years ago

Tony fucks TS Jane to a prostate climax

Tony fucks TS Jane to a prostate climax

Pornicom 2 years ago

Tony fucks TS Jane to a prostate climax

Tony fucks TS Jane to a prostate climax

Love4Porn 2 years ago

Prostate orgasms compilation. Personalsin collection vol. 140

Prostate orgasms compilation. Personalsin collection vol. 140

ShemaleSin 2 years ago

Her Plumb Machine Gives Her A Excruciating Rectal Climax

Her Plumb Machine Gives Her A Excruciating Rectal Climax

GayCK 2 years ago

sissy doggy pose aneros prostate cumshot in chastity cb6000s 3

sissy doggy pose aneros prostate cumshot in chastity cb6000s 3

GayCK 3 years ago

Transsexual in fishnet stockings with a dildo in the anus

Transsexual in fishnet stockings with a dildo in the anus

Sheshaft 2 years ago

Huge balls shemale go face down & ass up on couch getting anal fuck

Huge balls shemale go face down & ass up on couch getting anal fuck

FapHouse 3 years ago

this dildo always makes me cum hard

this dildo always makes me cum hard

xHamster 3 years ago

Sexy Shemale Jessica Bloom EXTREME Sissygasm Cumshot, Self Sucking &amp_ Foot Fetish Camshow Highlights (Full)

Premium HD 38:58

Sexy Shemale Jessica Bloom EXTREME Sissygasm Cumshot, Self Sucking &amp_ Foot Fetish Camshow Highlights (Full)

XVideosRed 3 years ago

Railing a ten Inch Faux-Cock In Virginity Splashing Sissygasms & Soles Neat Up For Dominatrix

Railing a ten Inch Faux-Cock In Virginity Splashing Sissygasms & Soles Neat Up For Dominatrix

TrannyGem 3 years ago

crossdresser handsfree prostate cumshot in chastity cb6000s 2

crossdresser handsfree prostate cumshot in chastity cb6000s 2

GayCK 4 years ago

Emma Slayer Analcurve Dual Popshot Railing Arms Free-For-All Maid

Emma Slayer Analcurve Dual Popshot Railing Arms Free-For-All Maid

TrannyGem 3 years ago

Crossdresser riding toy POV and cum milking with dildo in the ass

Crossdresser riding toy POV and cum milking with dildo in the ass

Clips4sale 3 years ago

Sasha Earth fucks her big ass with sex toys, dildo anal, playing solo at home

Sasha Earth fucks her big ass with sex toys, dildo anal, playing solo at home

xHamster 3 years ago

Sasha Earth fucks her ass with sex toys dildo anal play solo at home in the bathroom

Sasha Earth fucks her ass with sex toys dildo anal play solo at home in the bathroom

xHamster 3 years ago

Sasha Earth, shemale sissy transgender slut has anal sex at home, solo with sex toy, she fucks her big ass, dildo play a

Sasha Earth, shemale sissy transgender slut has anal sex at home, solo with sex toy, she fucks her big ass, dildo play a

xHamster 3 years ago

Tony fucks TS Jane to a prostate climax

Tony fucks TS Jane to a prostate climax

Fapnado 2 years ago

Alex anal fucks TS Fabriny to prostate orgasm

Alex anal fucks TS Fabriny to prostate orgasm

TrannyGem 2 years ago

Alex anal fucks TS Fabriny to prostate orgasm

Alex anal fucks TS Fabriny to prostate orgasm

PornDR 2 years ago

I want to spunk but if I hold myself back

I want to spunk but if I hold myself back

TrannyGem 2 years ago

tony fucks ts jane to a prostate climax

tony fucks ts jane to a prostate climax

PornOne 2 years ago

Big Caged &amp_ Uncaged Prostate Milking &amp_ Sissygasms Jessica Bloom

Premium HD 24:37

Big Caged &amp_ Uncaged Prostate Milking &amp_ Sissygasms Jessica Bloom

XVideosRed 3 years ago

I Myself In Fishnet Stockings And Ride A Big Dildo, I Am Dripping With Pleasure

I Myself In Fishnet Stockings And Ride A Big Dildo, I Am Dripping With Pleasure

xHamster 2 years ago

are you thirsty?here's some lemonade and milk

are you thirsty?here's some lemonade and milk

xHamster 2 years ago

Erika Oak's Anal Orgasm & Cumshot

Erika Oak's Anal Orgasm & Cumshot

xHamster 2 years ago

Erika Oak Sissygasm

Erika Oak Sissygasm

xHamster 2 years ago

I can;t stop jizzing! T-chick no-forearms utter assets climaxes with hitachi

I can;t stop jizzing! T-chick no-forearms utter assets climaxes with hitachi

TrannyGem 3 years ago

hj guts jism

GayCK 3 years ago

sissy doggy pose aneros prostate cumshot in chastity cb6000s 2

sissy doggy pose aneros prostate cumshot in chastity cb6000s 2

GayCK 4 years ago

sissy crossdresser prostate handsfree cumshot in chastity

sissy crossdresser prostate handsfree cumshot in chastity

GayCK 4 years ago

Concupiscent Wife Gives Sissy Honey Intensive Prostate Milking Shooting Self Facial

Concupiscent Wife Gives Sissy Honey Intensive Prostate Milking Shooting Self Facial

ShemaleSin 3 years ago

Manhandling My Fuckbox And Dinky

Manhandling My Fuckbox And Dinky

TrannyGem 3 years ago

Mistress Baton Does The Thousand Fist Challenge HD for QT

Premium 4K 37:46

Mistress Baton Does The Thousand Fist Challenge HD for QT

Clips4sale 1 year ago

She-creature Cumming Cowgirl Riding, sissy plowed rock-hard butt

She-creature Cumming Cowgirl Riding, sissy plowed rock-hard butt

TransTube.tv 7 months ago

Sissy Monti2003 very excited

Sissy Monti2003 very excited

xHamster 7 months ago

My orgasm in 6 minutes

My orgasm in 6 minutes

xHamster 6 months ago

Gay Sissy Take Many Huge Dildos Up Her Pussy

Gay Sissy Take Many Huge Dildos Up Her Pussy

XVideos 1 year ago

Gay Sissy Prostate Milking

Gay Sissy Prostate Milking

XVideos 1 year ago

Hitting the "P" Point - Small dildos lead to 2 PROSTATE ORGASMS

HD 0:30 / 21:34

Hitting the "P" Point - Small dildos lead to 2 PROSTATE ORGASMS

Clips4sale 9 months ago

Handsfree prostate cumming 3

Handsfree prostate cumming 3

GayCK 9 months ago

Multiorgasm sissy riding dildo

Multiorgasm sissy riding dildo

xHamster 1 year ago

Femboy in crimson spectacular gimp costume CUMpilation! Spunk from ass fucking, handballing and soles

Femboy in crimson spectacular gimp costume CUMpilation! Spunk from ass fucking, handballing and soles

TrannyGem 1 year ago

Ever see a cute guy squirt

Ever see a cute guy squirt

xHamster 1 year ago

Massive hands free prostate sex-toy spunk flow

Massive hands free prostate sex-toy spunk flow

ShemaleSin 1 year ago

Riding dildo in lingerie

Riding dildo in lingerie

BallsAndBoobs 7 months ago

Compilation of prostate orgasms: collection vol. 136 of personal videos

Compilation of prostate orgasms: collection vol. 136 of personal videos

XXXShemalePorn 7 months ago

I on a doll

xHamster 6 months ago

prostate sissygasm

prostate sissygasm

aShemaleTube 6 months ago

Prostate orgasms cumpilation. Personalsin collection vol. 149

Prostate orgasms cumpilation. Personalsin collection vol. 149

XVideos 1 year ago

Prostate orgasms cumpilation. Personalsin collection vol. 143

Prostate orgasms cumpilation. Personalsin collection vol. 143

XVideos 1 year ago

MASSIVE 10 Inch Dildo BALLS DEEP Makes me Cum Multiple Times - Jessica Bloom Anal Orgasms

MASSIVE 10 Inch Dildo BALLS DEEP Makes me Cum Multiple Times - Jessica Bloom Anal Orgasms

XVideos 3 years ago

Prostate double cum handsfree combo

Prostate double cum handsfree combo

XVideos 3 years ago

Prostate plowed anal dildo tranny

Prostate plowed anal dildo tranny

XVideos 5 years ago

Anal Sissy Milking With Glass of Cum Jessica Bloom

Anal Sissy Milking With Glass of Cum Jessica Bloom

XVideos 2 years ago

Anal toy

XVideos 4 years ago

Straight solo guy loves anal sex and humiliation

Straight solo guy loves anal sex and humiliation

xHamster 1 year ago

Jessica Bloom sissygasm guide & how a good slut cleans up (011)

HD 1:01 / 23:27

Jessica Bloom sissygasm guide & how a good slut cleans up (011)

FapHouse 3 years ago

Jessica Bloom extreme sissygasm cumshot, self sucking & foot fetish camshow highlights

HD 1:01 / 38:52

Jessica Bloom extreme sissygasm cumshot, self sucking & foot fetish camshow highlights

FapHouse 3 years ago

Prostate Milking in Stockings & Suspenders!

66% HD 0:08 / 0:39

Prostate Milking in Stockings & Suspenders!

FapHouse 8 months ago

Blond Femboy Sissy Twink Squirts Cum and Piss Because BFs Penis Is Too Big No Hands Prostate Anal Orgasm Bareback

Blond Femboy Sissy Twink Squirts Cum and Piss Because BFs Penis Is Too Big No Hands Prostate Anal Orgasm Bareback

SissyFlix 8 months ago

Sissygasm slut caged training massive cumshot & anal milking Jessica Bloom

57% HD 1:01 / 20:22

Sissygasm slut caged training massive cumshot & anal milking Jessica Bloom

FapHouse 3 years ago

Sabry Close, a beautiful blonde, breaks the ass of her partner with her big dick

HD 1:01 / 35:51

Sabry Close, a beautiful blonde, breaks the ass of her partner with her big dick

FapHouse 5 years ago

Biggest penis transsexual prostate climax

Biggest penis transsexual prostate climax

ShemaleSin 8 months ago

My Biggest Sissygasm Yet Jessica Bloom Fat Dildo (Full)

Premium HD 24:26

My Biggest Sissygasm Yet Jessica Bloom Fat Dildo (Full)

xnxxGold 3 years ago

Nylonjunge Enjoys Himself in Lingerie

Nylonjunge Enjoys Himself in Lingerie

xHamster 8 months ago

Compilation of prostate orgasms in personal collection volume - absolutely no mention of age, girl, or babe

Compilation of prostate orgasms in personal collection volume - absolutely no mention of age, girl, or babe

XXXShemalePorn 8 months ago

prostate Orgasm

prostate Orgasm

aShemaleTube 3 years ago

Prostate Pleasure Bodysuit on Trannies Gold

Prostate Pleasure Bodysuit on Trannies Gold

aShemaleTube 12 years ago

Sabry Close, a beautiful blonde, breaks the ass of her partner with her big dick

Sabry Close, a beautiful blonde, breaks the ass of her partner with her big dick

xHamster 10 months ago

Big dick crossdresser prostate vibrator cum

Big dick crossdresser prostate vibrator cum

xHamster 11 months ago

last week some long awaited toys finally arrive and i was eager to test them out part II

last week some long awaited toys finally arrive and i was eager to test them out part II

xHamster 1 year ago

Femboy leaks prostate milk

Femboy leaks prostate milk

aShemaleTube 1 year ago

F-Machine Alpha - Makes Jessica Bloom Cum Thick Load of Cum Wich She Licks up

Premium HD 15:52

F-Machine Alpha - Makes Jessica Bloom Cum Thick Load of Cum Wich She Licks up

XVideosRed 1 year ago

Screwing my Sissy Femboy butt HARD and giving myself multiple anal orgasms

Screwing my Sissy Femboy butt HARD and giving myself multiple anal orgasms

ShemaleSin 1 year ago

Orgasm collection IV

Orgasm collection IV

xHamster 3 years ago

Multiples Sissygasm & Prostate milking

Multiples Sissygasm & Prostate milking

xHamster 3 years ago

correct prostate massage for husband

correct prostate massage for husband

Tranny.one 3 years ago

Sissygasm Contest Day 1 - Sissy Trap Man Rails Faux-Cock

Sissygasm Contest Day 1 - Sissy Trap Man Rails Faux-Cock

TrannyGem 3 years ago

XFuta FUTANARI

Eporner 5 years ago

Ash-Blonde Hair Sissy Frolicking

Ash-Blonde Hair Sissy Frolicking

GayCK 4 years ago

fuck my ass and no hands cum prostate stimulation

fuck my ass and no hands cum prostate stimulation

xHamster 4 years ago

Femboy Crossdresser has Large Handsfree Money-Shot with Jean Cut-Offs

Femboy Crossdresser has Large Handsfree Money-Shot with Jean Cut-Offs

TrannyGem 4 years ago

19 20 21 22 23

4,142 results found

Related categories

Hands Free Prostate Prostate Milking Foreskin Prostate Massage Audio Handjob Compilation Edging Compilation Compilation Orgasm Penis Pump Orgasm Compilation Handjob & Cumshot Compilation Handjob Cumshot Premature Ejaculation Self Suck Milking Machine CEI (Cum Eating Instructions) Female Orgasm Compilation Cockring Cum Compilation

Narrow your search

prostate orgasm compilation shemale prostate orgasm

Categories Pornstars

Categories Pornstars

Legal

Terms of Service Privacy Statement Notice and Action Policy (Link Removal) DMCA / Copyright Acceptable Content Policy Digital Services Act 2257

Parents

Pornmd.com uses the "Restricted To Adults" (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2025 Pornmd.com. All rights reserved.