Insertion Videos - Trans (17,777)

Maximum Kinky and naked outdoor in the Snow riding Bob as Slave Crossdresser

Maximum Kinky and naked outdoor in the Snow riding Bob as Slave Crossdresser

xHamster 1 month ago

Xxxl Anal Dildo Slaming A Sexy Sissy Ass Extrem Anal Insertion

Xxxl Anal Dildo Slaming A Sexy Sissy Ass Extrem Anal Insertion

xHamster 2 years ago

Inserting 85mm Square Candy Bottle. #5

Inserting 85mm Square Candy Bottle. #5

xHamster 2 years ago

Trans man riding for the first time on a huge penis until orgasm

Trans man riding for the first time on a huge penis until orgasm

xHamster 2 months ago

”Big cock Asian ladyboy teen Many gets her tight booty banged after jerking”

”Big cock Asian ladyboy teen Many gets her tight booty banged after jerking”

LesbianBliss 2 weeks ago

”Wednesday Part 1: Scissor Sorority”

”Wednesday Part 1: Scissor Sorority”

TransHero 1 month ago

Trainer's Order No 14 Anal Sex in the Field

Trainer's Order No 14 Anal Sex in the Field

xHamster 2 months ago

Femboy sozan fuck her ass with huge cucamber

Femboy sozan fuck her ass with huge cucamber

xHamster 4 months ago

Pink Passion Featuring Large Anal Toys

71% HD 0:39 / 52:39

Pink Passion Featuring Large Anal Toys

FapHouse 1 year ago

Lets get my inner hole stretched ft David Anderson

Lets get my inner hole stretched ft David Anderson

xHamster 2 years ago

Penetration of Piss Hole

46% 0:39 / 8:09

Penetration of Piss Hole

FapHouse 6 months 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)

FapHouse 3 months ago

Tranny taking 13 inch dildo on her big ass

Tranny taking 13 inch dildo on her big ass

xHamster 2 years ago

Castrated Shelady Takes Biggest Dragon Fake Penis And Acquires Fisted 2 - Crystal Thayer

Castrated Shelady Takes Biggest Dragon Fake Penis And Acquires Fisted 2 - Crystal Thayer

PornUse 3 months ago

Sissy Slut Takes Huge Dildo

55% HD 0:10 / 15:38

Sissy Slut Takes Huge Dildo

LoyalFans 1 year ago

Huge Plug Stretching!!

Huge Plug Stretching!!

xHamster 5 months ago

getting off fuckhole

getting off fuckhole

5Gays 11 months ago

Mr Hankeys 3XL Nick Capra Dildo Destroys SlutBoyTO hole - Dildo POV

Mr Hankeys 3XL Nick Capra Dildo Destroys SlutBoyTO hole - Dildo POV

xHamster 7 months ago

*** Wearing a Tight Skirt, Black Garterbelt and Stockings Inserts a Cucumber Into Her Hole and Goes Out on the Street

*** Wearing a Tight Skirt, Black Garterbelt and Stockings Inserts a Cucumber Into Her Hole and Goes Out on the Street

FapHouse 4 months ago

Twink anal gaping

Twink anal gaping

xHamster 2 years ago

Ts Isabella sissy passions for his English Mistress

62% HD 1:01 / 24:03

Ts Isabella sissy passions for his English Mistress

FapHouse 3 years ago

Luna Luxxx Helps Evilyn Test Out Her New Toy

Luna Luxxx Helps Evilyn Test Out Her New Toy

Some.Porn 4 months ago

Part 2 of a Session with Some Huge Xl Toys Extreme Anal Insertions

56% HD 0:39 / 11:25

Part 2 of a Session with Some Huge Xl Toys Extreme Anal Insertions

FapHouse 1 year ago

Unboxed and Inside Me - First time with Big Daddy (L) - 13 inch dildo from Hankey's Toys

Unboxed and Inside Me - First time with Big Daddy (L) - 13 inch dildo from Hankey's Toys

xHamster 2 years ago

Gaping ass sissy 2025#16 - Inserting dildo anal masturbation -

Gaping ass sissy 2025#16 - Inserting dildo anal masturbation -

xHamster 6 months ago

Black shemale Chanel fucked a hot chick

Black shemale Chanel fucked a hot chick

Tranny.one 5 years ago

”Tattooed sex freaks Morea Black & Dalila Dark having lesbian assfucking time”

”Tattooed sex freaks Morea Black & Dalila Dark having lesbian assfucking time”

TransHero 1 month ago

Reina Hanno Flavors Her Cock with Candy

53% HD 1:01 / 26:25

Reina Hanno Flavors Her Cock with Candy

FapHouse 2 months ago

Sweet Shemale Woman Screwed by Her Dildo

Sweet Shemale Woman Screwed by Her Dildo

ALOTPorn 9 years ago

huge stepped anal plug

huge stepped anal plug

xHamster 4 months ago

Dirty MVP DTF

Some.Porn 4 months ago

Trans ladies in dresses toy ass and suck dildo in duo

Trans ladies in dresses toy ass and suck dildo in duo

Some.Porn 1 year ago

Another Shoulder Deep Fisting for Jasmine Dlight! Such a Good Time and so Many Fresh Fists!

71% HD 1:01 / 6:49

Another Shoulder Deep Fisting for Jasmine Dlight! Such a Good Time and so Many Fresh Fists!

FapHouse 1 year ago

Hung Huge Cock Cum

54% HD 0:39 / 5:01

Hung Huge Cock Cum

FapHouse 4 weeks ago

Anal gape complications

Anal gape complications

xHamster 1 month ago

HA36Miko inserts dildo into her anal, squirt and ejaculate outdoors!

HA36Miko inserts dildo into her anal, squirt and ejaculate outdoors!

xHamster 1 year ago

”Tiny Asian ladyboy teen Lee P-O-V blowjob & incredible anal fucking”

”Tiny Asian ladyboy teen Lee P-O-V blowjob & incredible anal fucking”

4Wank 2 years ago

Cum twice while riding huge corn

Cum twice while riding huge corn

xHamster 1 month ago

Anal massacre & anal fisting

Anal massacre & anal fisting

xHamster 2 years ago

My First Fisting Dildo

My First Fisting Dildo

xHamster 3 months ago

Sissy slut rides a 8 inch BBC dildo and inserts a cumsicle in the ass for a creampie

Sissy slut rides a 8 inch BBC dildo and inserts a cumsicle in the ass for a creampie

xHamster 2 years ago

Cumming on Fuck Machine!!

Cumming on Fuck Machine!!

xHamster 2 months ago

Krystall Cox riding a huge dildo then inserting the lube botle

Krystall Cox riding a huge dildo then inserting the lube botle

xHamster 1 year ago

Opening up the Biggest Bad Dragon Fucktoy Yet!!!

Opening up the Biggest Bad Dragon Fucktoy Yet!!!

4Gay 1 year ago

Ms Isabella's Playroom (pt3)

Ms Isabella's Playroom (pt3)

xHamster 1 year ago

Fishnet Femboy bounces his Fat Ass on Big Dildos

Fishnet Femboy bounces his Fat Ass on Big Dildos

xHamster 4 months ago

White Fishnet Sissy #15 - Riding a huge 95mm anal plug feels good -

White Fishnet Sissy #15 - Riding a huge 95mm anal plug feels good -

xHamster 1 year ago

AB2503 Secretary 50cm long dildo challenge (Chinese and English subtitles)

AB2503 Secretary 50cm long dildo challenge (Chinese and English subtitles)

xHamster 9 months ago

Inserting big bottle gourd deep in my ass

Inserting big bottle gourd deep in my ass

xHamster 1 week ago

Penetration von Pissloch

Penetration von Pissloch

xHamster 8 months ago

Femboy inserts dildo into gaping ass and cumshot from riding

Femboy inserts dildo into gaping ass and cumshot from riding

xHamster 8 months ago

🥕 How many Carrots can this Bunny fit in her Ass?

🥕 How many Carrots can this Bunny fit in her Ass?

xHamster 5 months ago

Cum ride with me

Cum ride with me

xHamster 1 year ago

Couple Slave. Lesbian Femdom Makes Boyfriend Cross Dress and Cuckolds Girlfriend in Front of Boyfriend

55% HD 1:01 / 36:05

Couple Slave. Lesbian Femdom Makes Boyfriend Cross Dress and Cuckolds Girlfriend in Front of Boyfriend

FapHouse 1 year ago

Sissy going all in with XL Bad Dragon dildo - Deep insertion

Sissy going all in with XL Bad Dragon dildo - Deep insertion

Tranny.one 4 years ago

SlutBoyTO's 1st Ride on Mr Hankeys Siswet's 🐙 ANAL DESTRUCTION

SlutBoyTO's 1st Ride on Mr Hankeys Siswet's 🐙 ANAL DESTRUCTION

xHamster 8 months ago

Crossdresser rides John Thomas Ass Master, tormenting experience

Crossdresser rides John Thomas Ass Master, tormenting experience

xHamster 2 years ago

Huge and wide Wouter Anal dildo - Balls deep full insertion

Huge and wide Wouter Anal dildo - Balls deep full insertion

xHamster 4 years ago

TS Gaby Angel Anal Fisted And Fucked Bareback

TS Gaby Angel Anal Fisted And Fucked Bareback

Wankoz 2 years ago

Ryu Nymph Stretches her Arse with a Monster can

Ryu Nymph Stretches her Arse with a Monster can

TrannyGem 4 years ago

Unexpected power pee while I was playing with semen on my ass

Unexpected power pee while I was playing with semen on my ass

xHamster 2 years ago

Fucking a guy's femboy hole with two hands, it's a shock!

Fucking a guy's femboy hole with two hands, it's a shock!

xHamster 2 years ago

TranssexualNetwork.com - Tranny with small tits inserts pole in dick and jerks off

TranssexualNetwork.com - Tranny with small tits inserts pole in dick and jerks off

UrGayPorn 7 months ago

Jesssy Doggy Rambone

Jesssy Doggy Rambone

xHamster 7 years ago

Massage Session With Ladyboy Maria Turned Into Bareback Fuck

Massage Session With Ladyboy Maria Turned Into Bareback Fuck

Wankoz 2 years ago

Anal Defloration, My First Insertion Ever I Love It

Anal Defloration, My First Insertion Ever I Love It

xHamster 10 months ago

Taking A 35mm Vibing Sound All The Way Wrecks Her

Taking A 35mm Vibing Sound All The Way Wrecks Her

TrannyGem 1 year ago

Big toys only with David Anderson

Big toys only with David Anderson

xHamster 3 years ago

Maximum Anal Stuffing for my Sissy Boy! Deep Insertion and Pegging Reward!

Maximum Anal Stuffing for my Sissy Boy! Deep Insertion and Pegging Reward!

xHamster 1 year ago

Kourtney Dash Inserts Her Monstrous T-model Manmeat Inwards Michael Jackmans Cock-squeezing Pink Hole

Kourtney Dash Inserts Her Monstrous T-model Manmeat Inwards Michael Jackmans Cock-squeezing Pink Hole

getTranny 2 months ago

”Two Shemales Having some Metal Rod Insertion Fun”

”Two Shemales Having some Metal Rod Insertion Fun”

TransHero 3 years ago

Me drilling myself like I do

Me drilling myself like I do

4Gay 1 year ago

Come and Me Right Now

Come and Me Right Now

Some.Porn 8 months ago

Fucking my buttplug and gaping my sissy hole

Fucking my buttplug and gaping my sissy hole

xHamster 3 years ago

mischievous Long legged blond inserts Bodacious Red-haired COUGAR And Her Wifey

mischievous Long legged blond inserts Bodacious Red-haired COUGAR And Her Wifey

Transvids.tv 8 months ago

Sexy ladyboy pleasures herself with a massive dildo & takes a wild anal ride

Sexy ladyboy pleasures herself with a massive dildo & takes a wild anal ride

VikiPorn 1 month ago

Today's live session, me getting railed by viewers on xhamsterlive

Today's live session, me getting railed by viewers on xhamsterlive

xHamster 10 months ago

Advanced Anal Stretching with Jasmine-dlight: Part 1 - the Initial Exploration

62% HD 1:01 / 9:58

Advanced Anal Stretching with Jasmine-dlight: Part 1 - the Initial Exploration

FapHouse 5 months ago

Stepsis Providing Me Some Ass-Fuck Instructing So She Can Knuckle Me

Stepsis Providing Me Some Ass-Fuck Instructing So She Can Knuckle Me

TrannyGem 3 months ago

Attractive shemale mimics a sloppy blowjob and swallows her cum in a dirty solo.

Attractive shemale mimics a sloppy blowjob and swallows her cum in a dirty solo.

XGroovy 5 months ago

Luna Luxxx Helps Evilyn Ink Test Out New Toy

Luna Luxxx Helps Evilyn Ink Test Out New Toy

Some.Porn 4 months ago

I Ride Two Big Dildos with a Surprise Ending.

I Ride Two Big Dildos with a Surprise Ending.

xHamster 4 months ago

”Madi Collins seduces Oliver with a sticky surprise”

”Madi Collins seduces Oliver with a sticky surprise”

TransHero 1 month ago

Miss Mikie Celebrates Hormone Insertion Day

Miss Mikie Celebrates Hormone Insertion Day

Transvids.tv 6 months ago

Watch Me Fuck my Fat Trans Asshole with my New Weird Dildo

Watch Me Fuck my Fat Trans Asshole with my New Weird Dildo

xHamster 3 weeks ago

Hardcore XXL Dildo deep in my Ass

Hardcore XXL Dildo deep in my Ass

xHamster 3 months ago

Anal Insertion

xHamster 2 months ago

”Huge cock machine fucking blonde babe”

”Huge cock machine fucking blonde babe”

TransHero 1 month ago

Essex Gal Lisa Pegging my Guy Plaything with Fat Faux-Cocks

Essex Gal Lisa Pegging my Guy Plaything with Fat Faux-Cocks

TrannyGem 1 year ago

ultra-kinky blond Nurse Administers A insane Beef Insertion

ultra-kinky blond Nurse Administers A insane Beef Insertion

TransTube.tv 10 months ago

Sissy college girl with pretty outfit inserts a vib and dildos into mouth and anal, anal climaxing and cumming at the same time

Sissy college girl with pretty outfit inserts a vib and dildos into mouth and anal, anal climaxing and cumming at the same time

xHamster 5 months ago

Full ANAL INVASION Destruction: numerous injections of apples, beer bottle and handballing in a Sumptuous Butt!

Full ANAL INVASION Destruction: numerous injections of apples, beer bottle and handballing in a Sumptuous Butt!

TrannyGem 2 years ago

Ginger TS Shiri cums hard from anal play and cock insertions

Ginger TS Shiri cums hard from anal play and cock insertions

Yeswegays 1 year ago

This was amazing

This was amazing

xHamster 2 years ago

Numerous Arms Free-For-All Ejaculations from Monster Werewolf Horsecock Handballing Group Sex

Numerous Arms Free-For-All Ejaculations from Monster Werewolf Horsecock Handballing Group Sex

TrannyGem 4 years ago

”Korra Del Rio's Sensual Solo Adventure”

”Korra Del Rio's Sensual Solo Adventure”

LesbianBliss 1 week ago

”Blonde transgender Lianna Lawson cums after urethra insertion”

”Blonde transgender Lianna Lawson cums after urethra insertion”

4Wank 1 year ago

What a big to fill (psykoanal)

What a big to fill (psykoanal)

xHamster 1 year ago

LEZ BE BAD - Lesbian Threesome Goes Wild With ANAL FISTING & Toes SuckingI n Naughty Fun

LEZ BE BAD - Lesbian Threesome Goes Wild With ANAL FISTING & Toes SuckingI n Naughty Fun

Some.Porn 4 months ago

Gets Her Juicy Ass Fucked And Fisted Until She - Erika Backster

Gets Her Juicy Ass Fucked And Fisted Until She - Erika Backster

PornUse 2 months ago

Hands Free Cum with huge Mr Hankeys Cody Cachet dildo

Hands Free Cum with huge Mr Hankeys Cody Cachet dildo

xHamster 10 months ago

Assfucking Snack for Trans Breezy Loren Aprile

Assfucking Snack for Trans Breezy Loren Aprile

TrannyGem 2 years ago

Redhead tranny Shiri Allwood inserting sounding rod

Redhead tranny Shiri Allwood inserting sounding rod

Sheshaft 6 years ago

Small-titted Mira reaches orgasm during sensual sounding session

Small-titted Mira reaches orgasm during sensual sounding session

XGroovy 1 year ago

Pussless FetLifeKitty - Bouncing Babe

Pussless FetLifeKitty - Bouncing Babe

xHamster 3 weeks ago

ryu Damsel playing with long plaything, glass ball-sac and monster can

ryu Damsel playing with long plaything, glass ball-sac and monster can

TransTube.tv 1 year ago

Sounding Her Hard-On Till She Can't Take Any More

Sounding Her Hard-On Till She Can't Take Any More

TrannyGem 1 year ago

Blonde TS's butt got destroyed once again

Blonde TS's butt got destroyed once again

Fapality 1 year ago

Melody Inserts a Bad Dragon Dildo

Melody Inserts a Bad Dragon Dildo

aShemaleTube 1 month ago

KC getting filled with milk to ride a huge dildo

KC getting filled with milk to ride a huge dildo

xHamster 1 year ago

Independent Training No65 Night Training Training (Self-Binding)

Independent Training No65 Night Training Training (Self-Binding)

xHamster 2 weeks ago

Set of Pool Balls Inserted & Pulled Out by Valentinarosa89 Stretch

73% HD 1:01 / 9:03

Set of Pool Balls Inserted & Pulled Out by Valentinarosa89 Stretch

FapHouse 1 year ago

POV Asian Femboy Gets Destroyed with A Fucking Machine

POV Asian Femboy Gets Destroyed with A Fucking Machine

MyLust 5 months ago

Inexperienced Teenager Anal Invasion Getting Off - Tranny Booty

Inexperienced Teenager Anal Invasion Getting Off - Tranny Booty

TrannyGem 5 years ago

Cock whore face writing - toilet and flashing at a mall

Cock whore face writing - toilet and flashing at a mall

xHamster 1 year ago

Sissy Jessica Bloom Eats Her Own Cum off a Cake! - Edging Sounding And Cumplay

Sissy Jessica Bloom Eats Her Own Cum off a Cake! - Edging Sounding And Cumplay

xHamster 1 year ago

Beautiful tgirl Bruninha Almeida fucks guy bareback

Beautiful tgirl Bruninha Almeida fucks guy bareback

Some.Porn 5 months ago

Ts Isabella Coupe's Bizarre Screwing, Object Insertions with Gaping Twat

Ts Isabella Coupe's Bizarre Screwing, Object Insertions with Gaping Twat

Amateur8 3 months ago

Sissygasm Training

Sissygasm Training

xHamster 1 year ago

TRAV ASSFUCKING EXTRAORDINARY (psykoanal)

TRAV ASSFUCKING EXTRAORDINARY (psykoanal)

MenGem 2 years ago

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