Sissy Milking Videos (4,830)

Fastened Sissy Gets Knob Milked Then Fed Her Own Load of Cum - Jessica Bloom and Polieana

Fastened Sissy Gets Knob Milked Then Fed Her Own Load of Cum - Jessica Bloom and Polieana

ShemaleSin 1 week ago

Blue chastity sissy gets bbc machine pounded

Blue chastity sissy gets bbc machine pounded

xHamster 1 year ago

Cd_Anita show her big ass and boobs

Cd_Anita show her big ass and boobs

xHamster 1 year ago

Femboy Ruins Four Cumshots and Moans Leaking Precum

Femboy Ruins Four Cumshots and Moans Leaking Precum

xHamster 3 months ago

Sissy Beta Cuckold spraying cream on Large Balls and getting sucked dry by $1000 Milking Machine

Sissy Beta Cuckold spraying cream on Large Balls and getting sucked dry by $1000 Milking Machine

ShemaleSin 4 weeks ago

School Sissy Uniform Milking Masturbation

School Sissy Uniform Milking Masturbation

aShemaleTube 1 month ago

Asian Crossdresser Fucking Machine: Net Stockings Part 2

Asian Crossdresser Fucking Machine: Net Stockings Part 2

xHamster 2 years ago

Rikki Ocean Cums on Breakfast and Eats Every Bite

Rikki Ocean Cums on Breakfast and Eats Every Bite

xHamster 1 year ago

Multitude Itsol get guts rubdown from admirer

Multitude Itsol get guts rubdown from admirer

TrannyGem 3 months ago

Self-sucking and fucking a tight young hole of a milky femboy on the track in a cruise

Self-sucking and fucking a tight young hole of a milky femboy on the track in a cruise

xHamster 1 month ago

Trans Dom CEI With Cock Milking Machine - Swallow Our Cum Slut

Trans Dom CEI With Cock Milking Machine - Swallow Our Cum Slut

xHamster 4 months ago

Cum Twice while Riding a Big Cucumber, Arab Moroccan Shemale Trans Girl 9ahba Skhona 3ziz 3liha zeb

Cum Twice while Riding a Big Cucumber, Arab Moroccan Shemale Trans Girl 9ahba Skhona 3ziz 3liha zeb

xHamster 4 months ago

Gigantic massive fuck sticks!!!

Gigantic massive fuck sticks!!!

4Gay 8 months ago

Step Mom milking her femboy with amazing orgasm and slow cumshot

Step Mom milking her femboy with amazing orgasm and slow cumshot

Tranny.one 1 year ago

PEGGING training and hot PROSTATE ORGASM for hot SISSY boyfriend

PEGGING training and hot PROSTATE ORGASM for hot SISSY boyfriend

xHamster 9 months ago

Jacking Myself For Every Last Droplet

Jacking Myself For Every Last Droplet

TrannyGem 3 years ago

Trans Lesbian Breast Milk Swallow Jessica Bloom And JenbyDoll

Trans Lesbian Breast Milk Swallow Jessica Bloom And JenbyDoll

xHamster 11 months ago

Tranny Foot Slave And Milking Stage 3 (MP4)

Tranny Foot Slave And Milking Stage 3 (MP4)

Clips4sale 9 months ago

Bound Sissy Gets Cock Milked Then Fed Her Own Load of Cum - Jessica Bloom and Polieana

Bound Sissy Gets Cock Milked Then Fed Her Own Load of Cum - Jessica Bloom and Polieana

xHamster 1 week ago

Milk Your Transgirl EPISODE

Milk Your Transgirl EPISODE

ShemaleSin 3 years ago

Took 10 days of edging to cum like this

Took 10 days of edging to cum like this

4KPorn 3 years ago

Wow! He Cums Twice in a row from so hot Cock Milking!

Wow! He Cums Twice in a row from so hot Cock Milking!

xHamster 1 year ago

TS Sasha bathes in Urinate, Spit, Milk and Cum - British Transsexual Floozy MtF Tranny

TS Sasha bathes in Urinate, Spit, Milk and Cum - British Transsexual Floozy MtF Tranny

ShemaleSin 4 years ago

Tranny faps enormous man-meat dry

Tranny faps enormous man-meat dry

TransTube.tv 2 months ago

ass fucking ejaculation while pretending to shower

ass fucking ejaculation while pretending to shower

TransTube.tv 10 months ago

Hung Transgirl Edges Her Big Dick Then Swallows Her Own Thick Load of Cum - Jessica Bloom

HD 1:01 / 16:47

Hung Transgirl Edges Her Big Dick Then Swallows Her Own Thick Load of Cum - Jessica Bloom

FapHouse 2 months ago

INDIAN TEEN FUCKING HER BEST FRIEND IN THE NEW APARTMENT

INDIAN TEEN FUCKING HER BEST FRIEND IN THE NEW APARTMENT

xHamster 11 months ago

Tied up in a chair, a femboy vividly cums from a milking machine.

Tied up in a chair, a femboy vividly cums from a milking machine.

XCafe 10 months ago

Sissy Femboy Drills a fleshlight until Jizz

Sissy Femboy Drills a fleshlight until Jizz

TrannyGem 8 months ago

Bettie Page - Bizarre Fetish Dreams Come True Part 4

Bettie Page - Bizarre Fetish Dreams Come True Part 4

xHamster 1 month ago

Ferris Re:Zero Gokkun messy milk glamour Chinese sissy femboy cosplayer / 男の娘フェリス　えちえちミルクごっくん

Ferris Re:Zero Gokkun messy milk glamour Chinese sissy femboy cosplayer / 男の娘フェリス　えちえちミルクごっくん

TrannyGem 2 years ago

Man attempts to get delight while he is locked in a v-card box. Compilation

Man attempts to get delight while he is locked in a v-card box. Compilation

TrannyGem 3 weeks ago

My Sperm Defiles Me

My Sperm Defiles Me

xHamster 1 month ago

Golden Shower wets my SISSY gurlfriend before FISTING cumshot

Golden Shower wets my SISSY gurlfriend before FISTING cumshot

xHamster 2 months ago

Leather trousers femboy plays with fuck stick

Leather trousers femboy plays with fuck stick

TrannyGem 3 years ago

Screams and moans of a sissy femboy boy and cum in his mouth!

Screams and moans of a sissy femboy boy and cum in his mouth!

Mensporn 3 months ago

Cute CD being a sissy girl????❤️

Cute CD being a sissy girl????❤️

UrGayPorn 3 years ago

Muscle babe Lushiana anal cumshow🍑

Muscle babe Lushiana anal cumshow🍑

aShemaleTube 10 months ago

A milky handsome guy let his ass get fucked by his daddy's big cock outside.

A milky handsome guy let his ass get fucked by his daddy's big cock outside.

xHamster 4 weeks ago

[Japanese Femboy] Freeing accumulated Sperm thru Rectal Getting Off on holidays!

[Japanese Femboy] Freeing accumulated Sperm thru Rectal Getting Off on holidays!

TrannyGem 6 months ago

Sissy Milked and Cumming on FuckMachine

65% HD 0:10 / 7:01

Sissy Milked and Cumming on FuckMachine

LoyalFans 2 years ago

Chastity Sissy Gaping on Huge Dildos and Leaking

Chastity Sissy Gaping on Huge Dildos and Leaking

xHamster 1 year ago

Trans Girl Colombiana Gets Fucked on the Tablet Ando Sofa Bed

Trans Girl Colombiana Gets Fucked on the Tablet Ando Sofa Bed

xHamster 2 months ago

I tied my dick so it wouldn't get hard

I tied my dick so it wouldn't get hard

xHamster 1 week ago

Femboy Sissy spills jizz and urinate no forearms while railing giant hard-on assfuck ejaculation guts foray

Femboy Sissy spills jizz and urinate no forearms while railing giant hard-on assfuck ejaculation guts foray

4Gay 1 year ago

Sissy Hard Anal Double ****

HD 0:10 / 12:27

Sissy Hard Anal Double ****

LoyalFans 2 years ago

Fucking the Throat of a White Whore

Fucking the Throat of a White Whore

xHamster 6 months ago

Fastened Sissy Gets Knob Milked Then Fed Her Own Load of Cum - Jessica Bloom and Polieana

Fastened Sissy Gets Knob Milked Then Fed Her Own Load of Cum - Jessica Bloom and Polieana

ShemaleSin 1 week ago

Sissy Femboy Screws a fleshlight until Cum

Sissy Femboy Screws a fleshlight until Cum

ShemaleSin 9 months ago

Milking machine

58% HD 0:39 / 3:42

Milking machine

FapHouse 2 years ago

Cumshot compilation winter 2020

Cumshot compilation winter 2020

LoveTranSex 1 year ago

Milk Machine

aShemaleTube 1 month ago

AryBell Dick Addicted

AryBell Dick Addicted

xHamster 3 weeks ago

Cum inside the bitch and putting my milk out

Cum inside the bitch and putting my milk out

xHamster 3 weeks ago

Latina amateur gives the best blowjob and swallows every drop

Latina amateur gives the best blowjob and swallows every drop

Jizzberry 3 years ago

Cute Femboy Gets Milked in VR by the Handy

Cute Femboy Gets Milked in VR by the Handy

xHamster 3 months ago

Milk Machine

xHamster 1 month ago

Sissy and the Milking Machine

Sissy and the Milking Machine

AbTranny 7 years ago

Trans Woman Femboy Sissy Worshipping Cock

Trans Woman Femboy Sissy Worshipping Cock

NastyCarSex 6 months ago

Cute Trans Hotty Caillazy Gets Milked

Cute Trans Hotty Caillazy Gets Milked

ShemaleSin 8 months ago

TS beauty Aiva anal lots of squirting & cum💦

TS beauty Aiva anal lots of squirting & cum💦

aShemaleTube 9 months ago

Femboy writhes in sofa with remote managed fucktoy tied to him!

Femboy writhes in sofa with remote managed fucktoy tied to him!

TrannyGem 1 year ago

donk agonorgasmos Compilation

donk agonorgasmos Compilation

Transvids.tv 6 months ago

Beautiful hands free anal love💦

Beautiful hands free anal love💦

aShemaleTube 10 months ago

Femdomme JOI - Swallower's Dilemma

Femdomme JOI - Swallower's Dilemma

xHamster 1 year ago

au-t-1493

TransVibe 11 months ago

Prostate milking Dec 17 2014

Prostate milking Dec 17 2014

BoyFriendTV 5 years ago

Vaniity And Alura Jenson rectal smash A whore teenage And Feed Him man milk

Vaniity And Alura Jenson rectal smash A whore teenage And Feed Him man milk

TrannyGem 4 years ago

Handjob Compilation - Stepmom Milking Sissy Femboy Stepson

Handjob Compilation - Stepmom Milking Sissy Femboy Stepson

xHamster 10 months ago

Sissy Cuckold Fed Creampie And Cum Foot Worship - Jessica Bloom ft Polieana

Sissy Cuckold Fed Creampie And Cum Foot Worship - Jessica Bloom ft Polieana

xHamster 7 months ago

High 2 anal quality Colombian porn, lots of anal sex and lots of milk

High 2 anal quality Colombian porn, lots of anal sex and lots of milk

xHamster 2 years ago

Milking cute trap melody and feeding her cum

Milking cute trap melody and feeding her cum

XVideos 5 months ago

Sissy Cow Bitch Pig Hardcore Extreme Nipple Pumping and Milking with real Cow Milking Machine

Sissy Cow Bitch Pig Hardcore Extreme Nipple Pumping and Milking with real Cow Milking Machine

xHamster 2 years ago

Muscular man fucks young gay Indian man

Muscular man fucks young gay Indian man

xHamster 10 months ago

Indian Gay Crossdresser Gaurisissy pressing her big boobs and fingering in her clean shaved big ass in red saree

Indian Gay Crossdresser Gaurisissy pressing her big boobs and fingering in her clean shaved big ass in red saree

xHamster 1 year ago

Chubby Blonde Latina Crossdresser in Heels gets her Fat Ass Pounded in Grindr Hookup

Chubby Blonde Latina Crossdresser in Heels gets her Fat Ass Pounded in Grindr Hookup

xHamster 5 months ago

Chinese Mistress Milking Crossdresser CD Slave Chinese

Chinese Mistress Milking Crossdresser CD Slave Chinese

FetishShrine 6 months ago

Cute young bitch lends her ass to her straight friend to be fucked and fills his ass with creampie cum

Cute young bitch lends her ass to her straight friend to be fucked and fills his ass with creampie cum

xHamster 3 months ago

Fucking and Milking Machine

61% 0:05 / 0:10

Fucking and Milking Machine

FapHouse 1 year 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

xHamster 1 year 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 3 months ago

it s this sissy milkboy s first time

HD 0:30 / 17:30

it s this sissy milkboy s first time

PornBox 7 months ago

Hetero stud cuffed revved assfucker by buttfuck masturbator

Hetero stud cuffed revved assfucker by buttfuck masturbator

MenGem 1 month ago

Sissy Trainer - Sissy - Feminization - Sissification

Sissy Trainer - Sissy - Feminization - Sissification

TrannyGem 2 years ago

Lovely Lean Sissy Femboy Trap with brilliant bod milking off and jizm - Jizz Flow

Lovely Lean Sissy Femboy Trap with brilliant bod milking off and jizm - Jizz Flow

TrannyGem 2 years ago

ts angelique monroe - webcam show from january 10, 2025

ts angelique monroe - webcam show from january 10, 2025

PornBox 7 months ago

Milking the first drops from my SISSY's PROSTATE

Milking the first drops from my SISSY's PROSTATE

xHamster 7 months ago

Jessica Bloom 2019 Cummy Self Deepthroat Highlights PMV Compilation

Jessica Bloom 2019 Cummy Self Deepthroat Highlights PMV Compilation

TrannyGem 4 years ago

Bouncing on Massive Dildo Makes Jessica Blooms Hard Girlcock Explode

Bouncing on Massive Dildo Makes Jessica Blooms Hard Girlcock Explode

xHamster 3 years ago

Poliana Milks and Feeds Sissy Jessica Bloom - Anal Fingering And Cum Swallow

Poliana Milks and Feeds Sissy Jessica Bloom - Anal Fingering And Cum Swallow

xHamster 1 year ago

Big Cock Cumshot Compilation with Sissy Slut Chantal Sweet

Big Cock Cumshot Compilation with Sissy Slut Chantal Sweet

xHamster 2 years ago

Anal Piggy Punishment: Big Boob Mistress, Pegging with Chastity, Extreme Humiliation, and Deep Fisting FULL-LENGTH (1080p)

67% HD 0:30 / 58:54

Anal Piggy Punishment: Big Boob Mistress, Pegging with Chastity, Extreme Humiliation, and Deep Fisting FULL-LENGTH (1080p)

Clips4sale 1 year ago

2 huge hands free cumshots in a row

2 huge hands free cumshots in a row

xHamster 1 year ago

Cutie Trans Hucow Melody Teaches Us How to Milk a Cock with Your Butt

67% HD 1:01 / 26:52

Cutie Trans Hucow Melody Teaches Us How to Milk a Cock with Your Butt

FapHouse 1 year ago

Milk Femboy fucked his asshole with his stepdad&#039;s hot stone cock and cum !

Milk Femboy fucked his asshole with his stepdad&#039;s hot stone cock and cum !

xHamster 1 month ago

Cock Milking Machine Drains Huge Trans Cock With Self Cum Swallow Jessica Bloom

Cock Milking Machine Drains Huge Trans Cock With Self Cum Swallow Jessica Bloom

XVideos 1 year ago

Step Mom and her personal femboy's hottest cumshot

Step Mom and her personal femboy's hottest cumshot

xHamster 2 years ago

Self Deep-Throating, Sissygasm T-Model Money-Shots - Jessica Bloom Camshow Highlights

Self Deep-Throating, Sissygasm T-Model Money-Shots - Jessica Bloom Camshow Highlights

TrannyGem 3 years ago

I had a great prostate orgasm in layers of pantyhose

I had a great prostate orgasm in layers of pantyhose

xHamster 7 months ago

Gay daddy jerking off black cock and shooting a big load

Gay daddy jerking off black cock and shooting a big load

xHamster 2 years ago

Cute trans Spicy_Meow teasing and touching her soft dick

Cute trans Spicy_Meow teasing and touching her soft dick

xHamster 2 years ago

Epic moment from "Muscle Glamazon Crazy Public Elevator Sissygasm"

Epic moment from "Muscle Glamazon Crazy Public Elevator Sissygasm"

xHamster 4 weeks ago

Top 10 Femdom Ideas 2022

Top 10 Femdom Ideas 2022

xHamster 1 year ago

Hung Transgirl Edges Her Big Dick Then Swallows Her Own Thick Load of Cum - Jessica Bloom

Hung Transgirl Edges Her Big Dick Then Swallows Her Own Thick Load of Cum - Jessica Bloom

xHamster 2 months ago

Valeria Dances and Models Her Cock Until She Explodes with Milk.

Valeria Dances and Models Her Cock Until She Explodes with Milk.

xHamster 1 month ago

A milky Twink 18 years old, immediately jumped on daddy's cock and got hot cum on his ass!

A milky Twink 18 years old, immediately jumped on daddy's cock and got hot cum on his ass!

xHamster 9 months ago

Daddy please milk my young cock

Daddy please milk my young cock

xHamster 1 year ago

Put these stockings and mini skirt on if you want me to make you cum

Put these stockings and mini skirt on if you want me to make you cum

xHamster 1 year ago

Step Mom milking her femboy with amazing orgasm and slow cumshot

Step Mom milking her femboy with amazing orgasm and slow cumshot

xHamster 2 years ago

Naomi anal makes her squirt💦

Naomi anal makes her squirt💦

aShemaleTube 9 months ago

Rikki Ocean Eats a Delicious Lemon Macaron with Fresh Cock Cream

Rikki Ocean Eats a Delicious Lemon Macaron with Fresh Cock Cream

xHamster 1 year ago

Multiple ruined orgasms

Multiple ruined orgasms

xHamster 11 months ago

Sissy Amanda hucow milking fat udders

Sissy Amanda hucow milking fat udders

xHamster 2 years ago

Young gay Indian fucking with latino with good ass

Young gay Indian fucking with latino with good ass

xHamster 10 months ago

Sissygasm, Slut’s Caged Training, Massive Cumshots & Anal Milking – Jessica Bloom

Sissygasm, Slut’s Caged Training, Massive Cumshots & Anal Milking – Jessica Bloom

xHamster 3 years ago

SISSY TRAINING SESSION, MILKING MY SISSY PREVIOUS TO PEGGING HER CUTE BOOTY

SISSY TRAINING SESSION, MILKING MY SISSY PREVIOUS TO PEGGING HER CUTE BOOTY

SortPorn 1 month ago

Cuffed and Fucked 720

63% HD 0:55 / 11:59

Cuffed and Fucked 720

Clips4sale 2 months ago

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

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

xHamster 4 weeks ago

Satin Crossdresser Milked By Zara (WMV)

Satin Crossdresser Milked By Zara (WMV)

Clips4sale 5 months ago

Fetish COCK BALL TORTURE with crimson High High-Heeled Shoes and milk clyster

Fetish COCK BALL TORTURE with crimson High High-Heeled Shoes and milk clyster

TrannyGem 1 year ago

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