Insertion Videos - Trans (15,572)

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

The Princess of Tennis

The Princess of Tennis

Some.Porn 8 months ago

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 3 months ago

Set of Pool Balls Inserted & Pulled Out by Valentinarosa89 Stretch

72% HD 1:01 / 9:03

Set of Pool Balls Inserted & Pulled Out by Valentinarosa89 Stretch

FapHouse 1 year ago

Ladyboy Taan - Glass Toy, Re-Insert Gaping Creampie 4k

Ladyboy Taan - Glass Toy, Re-Insert Gaping Creampie 4k

Xshemale 1 month ago

Hot Anal Sex Penetration of a Circumcised Penis Into a Tight Anus.

Hot Anal Sex Penetration of a Circumcised Penis Into a Tight Anus.

FapHouse 1 week ago

”Letting The Elf In”

”Letting The Elf In”

TransHero 2 months ago

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

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

xHamster 11 months ago

”A Freeuse Science Success”

”A Freeuse Science Success”

TransHero 2 months ago

Tgirl Kylie Maria intense ass fuck

Tgirl Kylie Maria intense ass fuck

Sheshaft 7 years ago

”Seeing them on the beach spelled trouble”

”Seeing them on the beach spelled trouble”

TransHero 2 months 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 8 months ago

Jasmine_dlight First Footing - Extreme Anal Insertions Foot Entirely up My Butt, Deep Insertion Anal Training Butt Slut

62% HD 0:39 / 3:07

Jasmine_dlight First Footing - Extreme Anal Insertions Foot Entirely up My Butt, Deep Insertion Anal Training Butt Slut

FapHouse 1 year ago

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

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

xHamster 9 months 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

Sissy cock gets fucked

Sissy cock gets fucked

xHamster 4 months 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

Sissygasm on huge deep toy in chastity

Sissygasm on huge deep toy in chastity

xHamster 2 years ago

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

66% HD 1:01 / 9:58

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

FapHouse 6 months ago

Teasing Shemale Dildo Fucking Her Ass

Teasing Shemale Dildo Fucking Her Ass

FetishShrine 2 years ago

Asian Shemale Emiri Momota Gets Controlled By Alien Monster And Fucks Alice Peachy TRAILER

Asian Shemale Emiri Momota Gets Controlled By Alien Monster And Fucks Alice Peachy TRAILER

xHamster 1 year ago

Kinky Games With Submissive Ladyboy

Kinky Games With Submissive Ladyboy

Pervclips 1 year ago

”Blonde transgender Lianna Lawson cums after urethra insertion”

”Blonde transgender Lianna Lawson cums after urethra insertion”

4Wank 1 year ago

Anal Insertion

xHamster 3 months 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

See the New Slave They Humiliate, Torment & Hard Fist

68% HD 1:01 / 18:02

See the New Slave They Humiliate, Torment & Hard Fist

FapHouse 1 year 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 4 months ago

Fucking Myself with a Big Anal Dildo

79% HD 1:01 / 21:55

Fucking Myself with a Big Anal Dildo

FapHouse 1 year ago

DP Freaks - Scene 4 - Two

DP Freaks - Scene 4 - Two

Some.Porn 6 months ago

Advanced Anal Stretching with Jasmine-dlight: Part 2 - Standing Position

69% HD 1:01 / 9:57

Advanced Anal Stretching with Jasmine-dlight: Part 2 - Standing Position

FapHouse 5 months ago

Biggest Anal Beads And Bareback Booty Screw For Ladyboy Kitty

Biggest Anal Beads And Bareback Booty Screw For Ladyboy Kitty

ShemaleSin 2 years ago

Inserting big bottle gourd deep in my ass

Inserting big bottle gourd deep in my ass

xHamster 1 month ago

Erika Oak Pisses Up Own Asshole

Erika Oak Pisses Up Own Asshole

xHamster 1 month ago

Patience game

xHamster 1 year ago

Annemieke tied and used in the woods

Annemieke tied and used in the woods

aShemaleTube 2 years ago

Tethered serf Natalie Mars' extreme buttfuck Unload & Wide Open Injections - TranssexualAngel

Tethered serf Natalie Mars' extreme buttfuck Unload & Wide Open Injections - TranssexualAngel

TrannyGem 5 years ago

”Korra Del Rio's Sensual Solo Adventure”

”Korra Del Rio's Sensual Solo Adventure”

429Men 2 days ago

GROOBYGIRLS: Jenissen Jenny Likes It Big

GROOBYGIRLS: Jenissen Jenny Likes It Big

xHamster 2 years ago

⋆ 3D FUTA Shoves Massive Toys Deep in MILF’s Ass Until She Screams in Ecstasy

⋆ 3D FUTA Shoves Massive Toys Deep in MILF’s Ass Until She Screams in Ecstasy

TransTube.tv 2 weeks ago

Caged and riding my humungous corn cob!

Caged and riding my humungous corn cob!

TransTube.tv 1 year ago

Pregnant Sissy (Pt 3)

Pregnant Sissy (Pt 3)

Tranny.one 1 year ago

Sabien And Taylor Show Slutlana Why They Are In Her Army!

Sabien And Taylor Show Slutlana Why They Are In Her Army!

Some.Porn 5 months ago

I fill my ass with milk and then fuck myself with my biggest XXL dildo

I fill my ass with milk and then fuck myself with my biggest XXL dildo

xHamster 8 months ago

Was the dildo too big for anal play ?

Was the dildo too big for anal play ?

xHamster 1 month ago

Anal School - How to Stretch Your Ass

Anal School - How to Stretch Your Ass

xHamster 1 week ago

Trainer's Order No63 Laundry Exposure 2nd Round

Trainer's Order No63 Laundry Exposure 2nd Round

xHamster 2 months ago

MONSTER DILDO TWINK BELLY BULGE RAM DEEP ANAL, PRINCE ALBERT, MUSCLE FLEX, RED HEAD BOTTOM SLUT, THIGH HIGH SOCKS FETISH, CUM

MONSTER DILDO TWINK BELLY BULGE RAM DEEP ANAL, PRINCE ALBERT, MUSCLE FLEX, RED HEAD BOTTOM SLUT, THIGH HIGH SOCKS FETISH, CUM

xHamster 1 year ago

Evilyn Ink Tattoos Robin Coffins While Fuck Her As She Blows Sarina Havok

Evilyn Ink Tattoos Robin Coffins While Fuck Her As She Blows Sarina Havok

Some.Porn 5 months ago

TS Gaby Angel Anal Fisted And Fucked Bareback

TS Gaby Angel Anal Fisted And Fucked Bareback

Wankoz 3 years ago

Ladyboy Nadia Jekrs Off With Toy In Her Ass

Ladyboy Nadia Jekrs Off With Toy In Her Ass

Eporner 11 months ago

HA56Secretly inserted a vibrator into the car to masturbate! There are cars passing by outside…

HA56Secretly inserted a vibrator into the car to masturbate! There are cars passing by outside…

xHamster 1 year ago

Meddle and Livi Ditch Their Boyfriends for Each Other

Meddle and Livi Ditch Their Boyfriends for Each Other

xHamster 11 months ago

Twink anal gaping

Twink anal gaping

xHamster 2 years ago

Crossdressing Ep Full Xhuishr

Crossdressing Ep Full Xhuishr

PornUse 4 months ago

Miss Mikie Celebrates Hormone Insertion Day

Miss Mikie Celebrates Hormone Insertion Day

Transvids.tv 7 months ago

Luna Luxxx Helps Evilyn Test Out Her New Toy

Luna Luxxx Helps Evilyn Test Out Her New Toy

Some.Porn 5 months ago

Cum twice while riding huge corn

Cum twice while riding huge corn

xHamster 2 months ago

Crossdresser while masturbating anal

Crossdresser while masturbating anal

xHamster 4 months ago

A compilation with a hot transvestite who likes to insert a dildo in his ass.

A compilation with a hot transvestite who likes to insert a dildo in his ass.

XGroovy 2 years ago

Hasumi Kurea And Aya Nitta In Jav Futanari Lesbian Sex 9

Hasumi Kurea And Aya Nitta In Jav Futanari Lesbian Sex 9

PePorn 4 months ago

Reina Hanno Flavors Her Cock with Candy

Reina Hanno Flavors Her Cock with Candy

xHamster 3 months ago

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

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

xHamster 7 months 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 5 months ago

Tgirls Juliana Reis n Emanuelly Polly Share Dildo

Tgirls Juliana Reis n Emanuelly Polly Share Dildo

Some.Porn 1 year ago

Pissing 1.5 Liters, Then Filling It All Back Inside

Pissing 1.5 Liters, Then Filling It All Back Inside

xHamster 4 months ago

POV Hard Pegging Jasmine Dlight From Mistress

POV Hard Pegging Jasmine Dlight From Mistress

xHamster 3 months 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

getting off fuckhole

getting off fuckhole

5Gays 1 year ago

Cum-and-pee Drink For a Sexy Tranny With a Fisted And Zucchini-stretched Anus

Cum-and-pee Drink For a Sexy Tranny With a Fisted And Zucchini-stretched Anus

Tranny.one 1 year ago

Large gape after monstrous ball ! :O

Large gape after monstrous ball ! :O

TrannyGem 2 years ago

Horny MILF pussylicking 21yo babe

Horny MILF pussylicking 21yo babe

Some.Porn 7 months ago

Ladyboy Nattcha Ass Filled With Huge Toy And Jerks Off

Ladyboy Nattcha Ass Filled With Huge Toy And Jerks Off

Eporner 4 years ago

Sissy slut’s deep anal training for big dicks

Sissy slut’s deep anal training for big dicks

xHamster 3 years ago

Move your hips like a panther and ejaculate.

Move your hips like a panther and ejaculate.

xHamster 7 months ago

”Madi Collins seduces Oliver with a sticky surprise”

”Madi Collins seduces Oliver with a sticky surprise”

TransHero 2 months ago

Dressed Up Kinky Ladyboy Becca Fingers And Jerks Off

Dressed Up Kinky Ladyboy Becca Fingers And Jerks Off

Eporner 2 years ago

Ass Destruction

Ass Destruction

xHamster 3 years ago

Anal gape complications

Anal gape complications

xHamster 2 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

Ladyboy Sonia Fucks Herself With A Beaded Toy And Jerks Off

Ladyboy Sonia Fucks Herself With A Beaded Toy And Jerks Off

Eporner 3 years ago

TS Shiri have anal sex with hung Jonah with a massive cock

TS Shiri have anal sex with hung Jonah with a massive cock

Sheshaft 6 years ago

Big toys only with David Anderson

Big toys only with David Anderson

xHamster 3 years ago

huge stepped anal plug

huge stepped anal plug

xHamster 5 months ago

Fishnet Femboy bounces his Fat Ass on Big Dildos

Fishnet Femboy bounces his Fat Ass on Big Dildos

xHamster 5 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

Shemale foot fuck a man

Shemale foot fuck a man

aShemaleTube 4 years ago

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

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

TrannyGem 2 years ago

Hardcore XXL Dildo deep in my Ass

Hardcore XXL Dildo deep in my Ass

xHamster 4 months ago

Assfucking Snack for Trans Breezy Loren Aprile

Assfucking Snack for Trans Breezy Loren Aprile

TrannyGem 2 years ago

Maid Masturbates for Her Master

Maid Masturbates for Her Master

xHamster 1 month ago

Dildo extreme insert

Dildo extreme insert

xHamster 2 months ago

Slamming my Ass Hard

Slamming my Ass Hard

xHamster 2 months ago

Crossdresser rides John Thomas Ass Master, tormenting experience

Crossdresser rides John Thomas Ass Master, tormenting experience

xHamster 2 years ago

Smashing my fuck-hole and opening up my rose!

Smashing my fuck-hole and opening up my rose!

TransTube.tv 1 year ago

Caged and riding my massive corn cob!

Caged and riding my massive corn cob!

ShemaleSin 2 years ago

Kristall Cox & Dirtygardengirl Anal Fisting, Dildo & Transsexual Prolapse Lick

64% HD 1:01 / 9:46

Kristall Cox & Dirtygardengirl Anal Fisting, Dildo & Transsexual Prolapse Lick

FapHouse 5 months ago

A sissy girl in a sexy skirt played with her ass and cum hard, crossdresser, cum

A sissy girl in a sexy skirt played with her ass and cum hard, crossdresser, cum

xHamster 3 months ago

Bisexual babe pegging crossdresser while fucked in 3some

Bisexual babe pegging crossdresser while fucked in 3some

Some.Porn 2 years ago

Yiffyfosque wreck her ass insane sextoy anal prolapse hankey's toys atlas 4xl

Yiffyfosque wreck her ass insane sextoy anal prolapse hankey's toys atlas 4xl

XXXShemalePorn 3 years ago

Femboy sozan fuck her ass with huge cucamber

Femboy sozan fuck her ass with huge cucamber

xHamster 5 months ago

The Nurse Extraction - Jasmine Dlight Extreme Anal Removal of Many Huge Dildos and Toys After a Wild Party by @valentinarosa89

63% HD 1:01 / 5:15

The Nurse Extraction - Jasmine Dlight Extreme Anal Removal of Many Huge Dildos and Toys After a Wild Party by @valentinarosa89

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

Trans cutie inserting unfathomable tiered sextoy until cummin

Trans cutie inserting unfathomable tiered sextoy until cummin

ShemaleSin 4 days ago

Jewelz Blu Invites Zariah Aura & Leilani Li For DP Madness

Jewelz Blu Invites Zariah Aura & Leilani Li For DP Madness

MyLust 6 months ago

TRAV ASSFUCKING EXTRAORDINARY (psykoanal)

TRAV ASSFUCKING EXTRAORDINARY (psykoanal)

MenGem 2 years ago

”Huge cock machine fucking blonde babe”

”Huge cock machine fucking blonde babe”

TransHero 2 months ago

Hands Free Cum with huge Mr Hankeys Cody Cachet dildo

Hands Free Cum with huge Mr Hankeys Cody Cachet dildo

xHamster 11 months ago

What a big to fill (psykoanal)

What a big to fill (psykoanal)

xHamster 1 year ago

Opening up the Biggest Bad Dragon Fucktoy Yet!!!

Opening up the Biggest Bad Dragon Fucktoy Yet!!!

4Gay 1 year ago

Caged Femboy with a Big Dildo in His Ass Cums From a Magic Wand for You

HD 1:01 / 14:03

Caged Femboy with a Big Dildo in His Ass Cums From a Magic Wand for You

FapHouse 1 year ago

Extraordinary Giant Dragon Sex Tool Stretches Teen out

Extraordinary Giant Dragon Sex Tool Stretches Teen out

ShemaleSin 4 years ago

Gaping My Ass with a Huge Butt Plug

66% HD 1:01 / 6:11

Gaping My Ass with a Huge Butt Plug

FapHouse 3 weeks ago

Ryu Nymph Stretches her Arse with a Monster can

Ryu Nymph Stretches her Arse with a Monster can

TrannyGem 4 years ago

crossdresser slave bitch

crossdresser slave bitch

BoyFriendTV 4 years ago

Gooning and Anal in Fishnets Camshow

Gooning and Anal in Fishnets Camshow

xHamster 1 year ago

Handjob and anal insertions for a thai t-girl

63% HD 1:01 / 13:50

Handjob and anal insertions for a thai t-girl

FapHouse 4 years ago

”Tiny Oriental ladyboy teen Lee P-O-V blowjob & incredible ass pumping fucking”

”Tiny Oriental ladyboy teen Lee P-O-V blowjob & incredible ass pumping fucking”

TransHero 4 years 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

Instructions from the trainer No 11 Daily exposure walks

Instructions from the trainer No 11 Daily exposure walks

xHamster 3 months ago

Amateur tranny toys insertions

Amateur tranny toys insertions

DrTuber 7 years ago

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