Machine Orgasm Videos (17,946)

FUCK PUSY BOY NO MERCY - Part 8

56% 4K 2:00 / 8:49

FUCK PUSY BOY NO MERCY - Part 8

Flirt4Free 6 months ago

Collection Sissy Orgasm Anal Cumshot

Collection Sissy Orgasm Anal Cumshot

xHamster 1 month ago

Ass to Mouth

4K 2:00 / 18:13

Flirt4Free 1 month ago

Submissive Teen Gets Railed by Fuck Machine & Squirts Cum Without Hands

56% HD 1:01 / 5:06

Submissive Teen Gets Railed by Fuck Machine & Squirts Cum Without Hands

FapHouse 1 year ago

Tgirl ravages her caboose for father on FaceTime

Tgirl ravages her caboose for father on FaceTime

TrannyGem 1 year ago

”Big Boobed Teen Redhead Stretches & Rides Sybian Sex Machine”

”Big Boobed Teen Redhead Stretches & Rides Sybian Sex Machine”

TransHero 1 month ago

Sissy Slut Training

Sissy Slut Training

xHamster 1 year ago

Massive ejaculation by inserting electric massage machine into anal

Massive ejaculation by inserting electric massage machine into anal

TrannyGem 3 years ago

High heels crossdresser hands free prostate orgasm cumshot

High heels crossdresser hands free prostate orgasm cumshot

xHamster 1 year ago

Fuck Machine Sissygasm Milking Jessica Bloom Cums Multiple Times

Fuck Machine Sissygasm Milking Jessica Bloom Cums Multiple Times

xHamster 3 years ago

Junnior & Archie Private Show

55% HD 2:00 / 17:38

Junnior & Archie Private Show

Flirt4Free 2 days ago

Sophia Loreen Private Show

4K 2:00 / 16:47

Sophia Loreen Private Show

Flirt4Free 2 months ago

Tiny Dick Sissy Jeffery Heuett Machine Fucked and Squirts

Tiny Dick Sissy Jeffery Heuett Machine Fucked and Squirts

xHamster 1 year ago

Estefhan Santos & Kendra Harper Private Show

Estefhan Santos & Kendra Harper Private Show

Flirt4Free 3 days ago

sissy squirt through cage during anal orgasm

sissy squirt through cage during anal orgasm

xHamster 1 month ago

Sophia Loreen Private Show

57% 4K 2:00 / 5:19

Sophia Loreen Private Show

Flirt4Free 5 months ago

”Suzi Anne gets screaming orgasm by the ebony fuck-machine”

”Suzi Anne gets screaming orgasm by the ebony fuck-machine”

ThePornstar 10 months ago

Trans Babe in Sexy Stockings Gabrielly Costa Gets Machine Fucked

Trans Babe in Sexy Stockings Gabrielly Costa Gets Machine Fucked

aShemaleTube 1 month ago

Hands free cumshot anal fuck machine

Hands free cumshot anal fuck machine

xHamster 1 year ago

Hercules & Lian & Lance Private Show

51% HD 2:00 / 9:07

Hercules & Lian & Lance Private Show

Flirt4Free 3 years ago

GUY BEGAN WILDING! Edging, Demolished, POT, Looong Edging and EVENTUALLY UTTER CLIMAX

GUY BEGAN WILDING! Edging, Demolished, POT, Looong Edging and EVENTUALLY UTTER CLIMAX

Gayhub 3 months ago

Milking Daddy Dry

Milking Daddy Dry

xHamster 2 weeks ago

Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum

Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum

xHamster 1 year ago

Liam Jacobson Private Show

60% HD 2:00 / 7:51

Liam Jacobson Private Show

Flirt4Free 1 year ago

Trans Big Tit Transformation

76% HD 1:01 / 44:49

Trans Big Tit Transformation

FapHouse 4 months ago

Lena Vesper's Last 2025 Stream

Lena Vesper's Last 2025 Stream

xHamster 2 months ago

Nerd gets drilled ????My g spot was sending me to orgasm each second

Nerd gets drilled ????My g spot was sending me to orgasm each second

BigTitsLust 3 months ago

The fucking machine is almost tearing my ass apart, it feels so good

The fucking machine is almost tearing my ass apart, it feels so good

xHamster 2 weeks ago

sissy climax on a plumbing machine ! your trap rails a fake penis and pops in the virginity belt!

sissy climax on a plumbing machine ! your trap rails a fake penis and pops in the virginity belt!

TrannyGem 2 years ago

Machine Sex in Nylons Makes Shemale Mariana Lins Climax

Machine Sex in Nylons Makes Shemale Mariana Lins Climax

ShemaleSin 4 years ago

Lana blue pissing again

Lana blue pissing again

aShemaleTube 1 week ago

Master & Christian & Nicco Private Show

48% HD 2:00 / 14:59

Master & Christian & Nicco Private Show

Flirt4Free 1 year ago

Patric & Oliver Private Show

68% HD 2:00 / 8:26

Patric & Oliver Private Show

Flirt4Free 3 years ago

The fucking machine let me moan until fuck me anal it goes deep and fast with this big bbc dildo

The fucking machine let me moan until fuck me anal it goes deep and fast with this big bbc dildo

xHamster 1 week ago

Hot shemale orgasm compilation

Hot shemale orgasm compilation

XGroovy 8 months ago

Sara & Elver Private Show

63% HD 2:00 / 7:37

Sara & Elver Private Show

Flirt4Free 2 months ago

Pegging orgasm cum compilation Clip 1

Pegging orgasm cum compilation Clip 1

xHamster 1 month ago

Luke Hardy & Cristian Ford Private Show

4K 2:00 / 35:09

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 week ago

SELENAS 58 MIN FUCKMACHINE MARATHON FULL VIDEO

SELENAS 58 MIN FUCKMACHINE MARATHON FULL VIDEO

xHamster 4 weeks ago

Bella Nightwish Private Show

65% 2:00 / 4:02

Bella Nightwish Private Show

Flirt4Free 1 month ago

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined by Intruder

62% HD 0:10 / 31:04

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined by Intruder

LoyalFans 5 months ago

two Ass-Fuck Ejaculations for Sissy in Innocence

two Ass-Fuck Ejaculations for Sissy in Innocence

TrannyGem 1 year ago

Emily VS Fuckmachine - is it normal, that white juice comes from my ass??? Trailer

Emily VS Fuckmachine - is it normal, that white juice comes from my ass??? Trailer

xHamster 2 years ago

diy gun machine big butt plug

diy gun machine big butt plug

TrannyGem 3 years ago

Naughty t-girl fuck her anal with huge dildo

Naughty t-girl fuck her anal with huge dildo

Wankoz 5 months ago

Sexy sissy Lucy testing out my new Barbarian dildo from John Thomas Toys on the fucking machine

Sexy sissy Lucy testing out my new Barbarian dildo from John Thomas Toys on the fucking machine

xHamster 2 years ago

Emma & Master Private Show

HD 2:00 / 11:18

Emma & Master Private Show

Flirt4Free 4 days ago

Sophia Loreen Private Show

49% HD 2:00 / 10:53

Sophia Loreen Private Show

Flirt4Free 3 years ago

One hour of fun with 12 inch and 17 inch dildo

One hour of fun with 12 inch and 17 inch dildo

xHamster 1 year ago

The fucking machine is almost tearing my ass apart

The fucking machine is almost tearing my ass apart

xHamster 1 month ago

Black Hottie Squirts All Over Her Toys

Black Hottie Squirts All Over Her Toys

Ebony8 4 months ago

My Nipples So Hard^^

My Nipples So Hard^^

Flirt4Free 10 months ago

The Only Way A Sissy Should Be Instructed To Jizz

The Only Way A Sissy Should Be Instructed To Jizz

TrannyGem 2 years ago

IMMENSE TRANS SPLATTER

IMMENSE TRANS SPLATTER

Transvids.tv 7 months ago

Huge hands free cumshot sissygasm

Huge hands free cumshot sissygasm

xHamster 1 year ago

Spit a Lot of Saliva on My Shiny Boobs^^

Spit a Lot of Saliva on My Shiny Boobs^^

Flirt4Free 8 months ago

The Fucking Machine and the 10 inch Dildo

The Fucking Machine and the 10 inch Dildo

xHamster 2 years ago

Pussy Machine Milks Barbara Perez

Pussy Machine Milks Barbara Perez

Some.Porn 11 months ago

Sophia Loreen Strip

53% HD 2:00 / 4:00

Sophia Loreen Strip

Flirt4Free 2 years ago

Sophia Loreen Private Show

56% 4K 2:00 / 7:57

Sophia Loreen Private Show

Flirt4Free 4 months ago

All The Way Throughout by Redvoidcgi (Shlong angel screwed by a giant pole until it comes out the other side)

All The Way Throughout by Redvoidcgi (Shlong angel screwed by a giant pole until it comes out the other side)

ShemaleSin 2 months ago

Elix & Elias & Paulo Private Show

46% HD 2:00 / 11:00

Elix & Elias & Paulo Private Show

Flirt4Free 7 months ago

Luke Hardy & Cristian Ford Private Show

60% HD 2:00 / 35:36

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 year ago

Jhordy & Cody & Archie Private Show

HD 2:00 / 31:27

Jhordy & Cody & Archie Private Show

Flirt4Free 4 days ago

Hanna Ven Private Show

56% HD 2:00 / 2:17:23

Hanna Ven Private Show

Flirt4Free 1 year ago

Jhon & Derek & Chris Private Show

42% HD 2:00 / 31:06

Jhon & Derek & Chris Private Show

Flirt4Free 3 years ago

[Japanese Femboy - FULL] Sissygasm by Shagging Machine

[Japanese Femboy - FULL] Sissygasm by Shagging Machine

TrannyGem 1 year ago

Chastity Sissy Cums From Big Black Cock Fucking Machine And Swallows Her Own Cum

Chastity Sissy Cums From Big Black Cock Fucking Machine And Swallows Her Own Cum

Dafreeporn 6 months ago

Master & Ithan & Aleex Private Show

56% HD 2:00 / 31:36

Master & Ithan & Aleex Private Show

Flirt4Free 6 months ago

Jamer & Owen & Hercules Private Show

43% HD 2:00 / 54:50

Jamer & Owen & Hercules Private Show

Flirt4Free 3 years ago

Sissy Intense Anal Fucking with Rockhard Monstercock

Sissy Intense Anal Fucking with Rockhard Monstercock

xHamster 1 month ago

”Blonde in pile driver anal fucked”

”Blonde in pile driver anal fucked”

TransHero 1 month ago

PrincessCrossed and Asteria Summer Compilation

PrincessCrossed and Asteria Summer Compilation

TrannyGem 3 weeks ago

Tgirl Multitude Itsol gapes her butt with yam-sized fake penis plowing machine

Tgirl Multitude Itsol gapes her butt with yam-sized fake penis plowing machine

TrannyGem 11 months ago

Roy & Hercules & Jamer Private Show

50% HD 2:00 / 4:09

Roy & Hercules & Jamer Private Show

Flirt4Free 3 years ago

Luke Hardy & Cristian Ford Private Show

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 month ago

Slobbery Suck Fingers

Slobbery Suck Fingers

Flirt4Free 10 months ago

Grade a Lena Vesper Goon Fuel

HD 0:39 / 20:56

Grade a Lena Vesper Goon Fuel

FapHouse 3 months ago

CUM IN PUSSY - Part 3

55% HD 2:00 / 9:55

CUM IN PUSSY - Part 3

Flirt4Free 3 weeks ago

Sophie Fantasy Private Show

39% HD 2:00 / 4:09

Sophie Fantasy Private Show

Flirt4Free 1 year ago

2026 Handsfree Orgasms, Prostate Cumshot Part 3

HD 1:01 / 29:34

2026 Handsfree Orgasms, Prostate Cumshot Part 3

FapHouse 1 week ago

Sophia Loreen Private Show

4K 2:00 / 11:03

Sophia Loreen Private Show

Flirt4Free 1 month ago

Home Made Male Fuking Machine Part 1

Home Made Male Fuking Machine Part 1

xHamster 2 months ago

Fuck Machine Brings Me to Orgasm

Fuck Machine Brings Me to Orgasm

xHamster 2 months ago

Pegging orgasm cum compilation

Pegging orgasm cum compilation

xHamster 1 month ago

Virginity Sissy F Machine Stroking - Jessica Bloom Jizzes Arms Free-For-All And Gulps Jizz

Virginity Sissy F Machine Stroking - Jessica Bloom Jizzes Arms Free-For-All And Gulps Jizz

TrannyGem 1 year ago

Matt & Elvis & Aron Private Show

Matt & Elvis & Aron Private Show

Flirt4Free 3 years ago

sissy orgasm on a fucking machine ! your trap rides a dildo and cums in the chastity belt!

sissy orgasm on a fucking machine ! your trap rides a dildo and cums in the chastity belt!

xHamster 1 year ago

Aleex & Paulo Private Show

52% HD 2:00 / 9:50

Aleex & Paulo Private Show

Flirt4Free 8 months ago

Hercules & Lance & Lian Miller Private Show

63% HD 2:00 / 8:05

Hercules & Lance & Lian Miller Private Show

Flirt4Free 3 years ago

Oil on My Pretty Boobs

Oil on My Pretty Boobs

Flirt4Free 11 months ago

FTM Kahn Fawkes's Cooch gets Taunted and Denied

FTM Kahn Fawkes's Cooch gets Taunted and Denied

TrannyGem 1 year ago

Luke Hardy & Cristian Ford Private Show

51% HD 2:00 / 13:59

Luke Hardy & Cristian Ford Private Show

Flirt4Free 1 year ago

t-girl in fishnets machine screwed until climax

t-girl in fishnets machine screwed until climax

ShemaleSin 1 year ago

Sophia Loreen Private Show

62% HD 2:00 / 18:14

Sophia Loreen Private Show

Flirt4Free 2 years ago

TGirl in fishnets machine humped until climax

TGirl in fishnets machine humped until climax

TrannyGem 1 year ago

DESTRIY HOLE VERY HARD

61% HD 2:00 / 8:53

DESTRIY HOLE VERY HARD

Flirt4Free 1 year ago

Princess butt slut orgasms🍑💦

Princess butt slut orgasms🍑💦

aShemaleTube 1 year ago

adorable femboy with romp-machine wiggling ejaculation intence romping immense fake penis wide open poon

adorable femboy with romp-machine wiggling ejaculation intence romping immense fake penis wide open poon

TransTube.tv 8 months ago

T-Model plumbed by romp machine

T-Model plumbed by romp machine

TrannyGem 4 years ago

'I'm So Close!' She Doesn't Even Realise She's Jism

'I'm So Close!' She Doesn't Even Realise She's Jism

TrannyGem 1 year ago

Two huge toys opening my ass cunt and i still want more

Two huge toys opening my ass cunt and i still want more

xHamster 1 year ago

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

ShemaleSin 1 year ago

Simon & Juseph & Alejandro Private Show

53% HD 2:00 / 1:02:40

Simon & Juseph & Alejandro Private Show

Flirt4Free 2 years ago

Jhordy & Maxx Private Show

59% HD 2:00 / 7:55

Jhordy & Maxx Private Show

Flirt4Free 6 months ago

Fucking machine on high speed milking a cock to massive cum

Fucking machine on high speed milking a cock to massive cum

xHamster 1 year ago

Size Queen Lena Vesper Wrecks Her Pussy Live

HD 0:39 / 26:49

Size Queen Lena Vesper Wrecks Her Pussy Live

FapHouse 1 month ago

Sophie Fantasy Private Show

HD 2:00 / 50:39

Sophie Fantasy Private Show

Flirt4Free 2 years ago

Sissy crossdresser roped and machine smashed

Sissy crossdresser roped and machine smashed

Gayhaus 2 months ago

charming trans in shlong chastity cage has an anal prostate climax and cum explodes during the time that drilled hard and fast with a biggest sex tool screw machine

charming trans in shlong chastity cage has an anal prostate climax and cum explodes during the time that drilled hard and fast with a biggest sex tool screw machine

ShemaleSin 4 years ago

Frederick & Aleex & Daaniel Private Show

Frederick & Aleex & Daaniel Private Show

Flirt4Free 4 months ago

Daphne Caught

74% HD 1:01 / 6:41

FapHouse 10 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 10 months ago

Always longer and always bigger

Always longer and always bigger

aShemaleTube 1 week ago

Alexander & Patric & Alfonso Private Show

42% HD 2:00 / 1:26:38

Alexander & Patric & Alfonso Private Show

Flirt4Free 3 years ago

Hardcore anal machine fuck in lingerie and high heels with a huge dildo makes me tremble and destroy my hole

Hardcore anal machine fuck in lingerie and high heels with a huge dildo makes me tremble and destroy my hole

xHamster 2 weeks ago

Richii Smiith Private Show

Richii Smiith Private Show

Flirt4Free 2 weeks ago

Crossdresser with fake tits gets worried by the sex machine

Crossdresser with fake tits gets worried by the sex machine

xHamster 1 year ago

Trans Hotty Jizzing while Penetrated by a Fucky-Fucky Machine

Trans Hotty Jizzing while Penetrated by a Fucky-Fucky Machine

TrannyGem 2 years ago

Sophia Loreen Party on Aug 29, 2024

HD 2:00 / 1:43:56

Sophia Loreen Party on Aug 29, 2024

Flirt4Free 1 year ago

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