Sissy Training Videos (83,367)

Milking a nice femboy and having a hot arms-free-for-all orgasm close up

Milking a nice femboy and having a hot arms-free-for-all orgasm close up

MyTransfix 4 weeks ago

G065 - Chinese Princess Swallow Jerkoff

57% HD 0:39 / 9:26

G065 - Chinese Princess Swallow Jerkoff

FapHouse 1 year ago

Relaxing Time with Milking Machine

Relaxing Time with Milking Machine

FapHouse 1 year ago

Jacob Malik Private Show

54% HD 2:00 / 4:28

Jacob Malik Private Show

Flirt4Free 7 months ago

Anime Girl Training My Ass with Strap on Femdom

62% HD 0:39 / 3:20

Anime Girl Training My Ass with Strap on Femdom

FapHouse 1 year ago

Sissy Training - Sissygasm Encouragement Jessica Bloom

Sissy Training - Sissygasm Encouragement Jessica Bloom

Tranny.one 4 years ago

Tiny Cute Gurl Needs Big Cock in Her Tight Pussy

Tiny Cute Gurl Needs Big Cock in Her Tight Pussy

FapHouse 4 months ago

Tammysissy Webcam

Tammysissy Webcam

XHamster 2 months ago

Cherry Becoming Feminine

HD 1:01 / 15:19

Cherry Becoming Feminine

FapHouse 2 years ago

Swallow My Loads Sissy Trainer

69% HD 0:39 / 10:58

Swallow My Loads Sissy Trainer

FapHouse 3 months ago

Sissy Wife Blowjob Practice - Clara Dee JOI

66% HD 0:39 / 15:05

Sissy Wife Blowjob Practice - Clara Dee JOI

FapHouse 2 years ago

Fat Ass Femboy Raven Asshole Gaped, Creampie and Cuming After Intense Anal Sex with BBC Dildo

45% HD 1:01 / 29:01

Fat Ass Femboy Raven Asshole Gaped, Creampie and Cuming After Intense Anal Sex with BBC Dildo

FapHouse 5 months ago

Sissy Slut Training

Sissy Slut Training

XHamster 2 years ago

BBC Sissygasm

65% 0:39 / 1:42

FapHouse 1 year ago

He Fucks Me Like a Bitch... I Love Being Trained by Master

67% HD 1:01 / 18:09

He Fucks Me Like a Bitch... I Love Being Trained by Master

FapHouse 3 months ago

GLORYHOLE LUNCH BREAK

52% HD 0:10 / 24:59

GLORYHOLE LUNCH BREAK

LoyalFans 3 years ago

Reaching Sissygasm by Hitting My Clitty in Chastity with Big Headed Dildo (after Anal Play)

Reaching Sissygasm by Hitting My Clitty in Chastity with Big Headed Dildo (after Anal Play)

FapHouse 1 year ago

Chatty Crossdresser chats again... and tries new plug 2023-02-26 part 2

Chatty Crossdresser chats again... and tries new plug 2023-02-26 part 2

XHamster 3 years ago

Sexy Striptease Became into Hot Sex

57% 4K 2:00 / 35:09

Sexy Striptease Became into Hot Sex

Flirt4Free 7 months ago

Sophia Loreen Private Show

4K 2:00 / 10:50

Sophia Loreen Private Show

Camster 2 weeks ago

Sophia Loreen Party on Sep 7, 2026 - Part 3

63% 4K 2:00 / 4:07

Sophia Loreen Party on Sep 7, 2026 - Part 3

Flirt4Free 2 weeks ago

Latex Doll Milking Training 2

HD 0:39 / 19:09

Latex Doll Milking Training 2

FapHouse 4 months ago

Santiago & Joseph Private Show

61% HD 2:00 / 24:52

Santiago & Joseph Private Show

Flirt4Free 2 years ago

Master & Ithan Private Show

54% HD 2:00 / 9:40

Master & Ithan Private Show

Flirt4Free 1 year ago

(s)Join this group and you wil see: The best Twerk ever, a Juicy Ass bouncing and Riding a long toy, making me dripping all my juices! (yummy) (squirt)

(s)Join this group and you wil see: The best Twerk ever, a Juicy Ass bouncing and Riding a long toy, making me dripping all my juices! (yummy) (squirt)

Flirt4Free 2 years ago

Zara Clark Private Show

Zara Clark Private Show

Flirt4Free 9 months ago

Christian & Lian Private Show

51% HD 2:00 / 15:05

Christian & Lian Private Show

Flirt4Free 3 years ago

Big Tits Slut Vibrates Her Chastity Cage

63% HD 0:39 / 5:18

Big Tits Slut Vibrates Her Chastity Cage

FapHouse 3 months ago

Magnificent Milky Twunk Nails Ebony Fem W Facial Cumshot

Magnificent Milky Twunk Nails Ebony Fem W Facial Cumshot

Gay4Porn 5 years ago

Marian & Richard Private Show

57% HD 2:00 / 20:44

Marian & Richard Private Show

Flirt4Free 2 weeks ago

Mike Swift & David Golden Private Show

67% HD 2:00 / 4:02

Mike Swift & David Golden Private Show

Flirt4Free 3 weeks ago

Assfucked in Armbinders

70% HD 0:39 / 16:45

Assfucked in Armbinders

FapHouse 5 months ago

Pink Sissy Bride Dildo Play and Tombussy Chastity Cumming

57% HD 1:01 / 30:20

Pink Sissy Bride Dildo Play and Tombussy Chastity Cumming

FapHouse 4 weeks ago

Master & Ithan & Aleex Private Show

51% HD 2:00 / 7:13

Master & Ithan & Aleex Private Show

Flirt4Free 1 year ago

Pink Sissy Bride Dildo Play and Tombussy Chastity Cumming

61% HD 0:39 / 30:20

Pink Sissy Bride Dildo Play and Tombussy Chastity Cumming

FapHouse 4 weeks ago

Massive Topped Toys Artemis 125 makes me gape

Massive Topped Toys Artemis 125 makes me gape

XHamster 3 weeks ago

Lisan & Mine Private Show

62% 4K 2:00 / 6:02

Lisan & Mine Private Show

Flirt4Free 4 weeks ago

Sophia Loreen Private Show

61% HD 2:00 / 4:58

Sophia Loreen Private Show

Flirt4Free 3 months ago

Luke Hardy & Cristian Ford Private Show

HD 2:00 / 11:04

Luke Hardy & Cristian Ford Private Show

Flirt4Free 2 years ago

Sophia Loreen Private Show

70% 4K 2:00 / 13:07

Sophia Loreen Private Show

Flirt4Free 9 months ago

Sophia Loreen Strip

54% HD 2:00 / 4:00

Sophia Loreen Strip

Flirt4Free 3 years ago

I ride my huge dildo close up

I ride my huge dildo close up

XHamster 3 weeks ago

Huge pyramid dildo ride - loose asshole, gape, precum and cumshot

Huge pyramid dildo ride - loose asshole, gape, precum and cumshot

XHamster 3 weeks ago

Sophia Loreen Shows Her Wonderful Body and That Beautiful Backside

Sophia Loreen Shows Her Wonderful Body and That Beautiful Backside

Flirt4Free 4 years ago

Mommy Ruby first time with a t-girl

Mommy Ruby first time with a t-girl

XHamster 7 months ago

Jessica Simpsin Private Show

Jessica Simpsin Private Show

Camster 6 years ago

Step-Mommy Teaches You How to Cum From Anal Like a Good Sissy Slut - Jessica Bloom Sissygasm Guide

Step-Mommy Teaches You How to Cum From Anal Like a Good Sissy Slut - Jessica Bloom Sissygasm Guide

XHamster 5 months ago

Jacuzzi with French Trans Goddess Her GF Catches Us & Pegs Us Both

HD 0:39 / 32:18

Jacuzzi with French Trans Goddess Her GF Catches Us & Pegs Us Both

FapHouse 4 months ago

POV Roommate Cock Sucking Persuasion, Dirty Talk and Sph

POV Roommate Cock Sucking Persuasion, Dirty Talk and Sph

XHamster 1 year ago

Anahi Hefner Private Show

HD 2:00 / 14:14

Anahi Hefner Private Show

Flirt4Free 3 years ago

Mistress Sex with Submissive Chastity Sissy

Mistress Sex with Submissive Chastity Sissy

Clips 3 months ago

Brutus K Private Show

Brutus K Private Show

Flirt4Free 11 years ago

Sissy railing fake penis in prostitute appartment

Sissy railing fake penis in prostitute appartment

4Gay 11 months ago

Lika Kai Private Show

68% 4K 2:00 / 9:50

Lika Kai Private Show

Camster 2 weeks ago

Big Cock in Sweet Pussy

55% 4K 2:00 / 13:17

Big Cock in Sweet Pussy

Flirt4Free 1 year ago

Huge hands free cumshot sissygasm

Huge hands free cumshot sissygasm

XHamster 2 years ago

My Bf Caught Me and Spanked Me for Being Disobedient

My Bf Caught Me and Spanked Me for Being Disobedient

Flirt4Free 4 months ago

Giant Anal Cone Dildo Sitting and Bouncing Till the Base & Gaping Asshole

Giant Anal Cone Dildo Sitting and Bouncing Till the Base & Gaping Asshole

XHamster 2 months ago

Femboy Gape Compilation #2 fart-gapes

Femboy Gape Compilation #2 fart-gapes

XHamster 7 months ago

Twinkerbell Pegging the Lost Femboi in Chastity

Twinkerbell Pegging the Lost Femboi in Chastity

XHamster 1 year ago

Nicco & Patric & Santiago Have Amazing Threesome

58% HD 2:00 / 1:04:58

Nicco & Patric & Santiago Have Amazing Threesome

Flirt4Free 2 years ago

Kimmi Krux gets his tight ass fisted and humiliated in amateur sissy femboy video

Kimmi Krux gets his tight ass fisted and humiliated in amateur sissy femboy video

GayVD 1 month ago

Transgirl Flex Her Big Balls

68% 1:01 / 11:20

Transgirl Flex Her Big Balls

FapHouse 7 months ago

Cum eating trainer video for the greedy sissy faggot whores

Cum eating trainer video for the greedy sissy faggot whores

Tranny.one 9 years ago

I Love BBC! Fuck My Asspussy Deep and Rough!

I Love BBC! Fuck My Asspussy Deep and Rough!

XHamster 4 months ago

Man Transformed Into Woman to Go Clubbing

Man Transformed Into Woman to Go Clubbing

XHamster 2 months ago

Jhordy & Maxx Private Show

54% HD 2:00 / 24:38

Jhordy & Maxx Private Show

Flirt4Free 1 year ago

10 unreal anal orgasms outdoor!!

10 unreal anal orgasms outdoor!!

PornBox 2 years ago

Sissy Training

Itsrealamateurs 1 day ago

Compilation With the Best Solo Cumshots: Sexy Shemale Makes Herself Cum By Shoving Dildos In Her Ass

Compilation With the Best Solo Cumshots: Sexy Shemale Makes Herself Cum By Shoving Dildos In Her Ass

XGroovy 2 years ago

Sissification Appointment

Sissification Appointment

XHamster 3 months ago

sissy slut s use of bbc

HD 0:26 / 46:52

sissy slut s use of bbc

PornBox 1 year ago

stepMommy dom milking sissy boy in sexy lingerie and stockings

stepMommy dom milking sissy boy in sexy lingerie and stockings

XHamster 6 months ago

HANDS FREE SISSYGASM CUMSHOT from Aneros MGX Syn Trident

HANDS FREE SISSYGASM CUMSHOT from Aneros MGX Syn Trident

XHamster 3 years ago

Wild Sabrina Private Show

51% HD 2:00 / 16:26

Wild Sabrina Private Show

Flirt4Free 7 years ago

SAY “I AM A FAGGOT MISTRESS RAVEN”

60% HD 0:10 / 23:45

SAY “I AM A FAGGOT MISTRESS RAVEN”

LoyalFans 3 years ago

Tantaly : Chastity Release: The Last Penetration of your Life? Mistress Julia

Tantaly : Chastity Release: The Last Penetration of your Life? Mistress Julia

XHamster 2 years ago

Submissive Asian Ladyboy Anal Casting & Slave Training

Submissive Asian Ladyboy Anal Casting & Slave Training

XHamster 11 months ago

Lisan & Mine Private Show

Lisan & Mine Private Show

Camster 1 week ago

Ultra-cute Femboy in Fishnets Instructs his Rear entrance until he Ejaculates on Himself

Ultra-cute Femboy in Fishnets Instructs his Rear entrance until he Ejaculates on Himself

4Gay 8 months ago

Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 19

Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 19

XHamster 8 months ago

AB105 Christmas Girl's Bondage Party-squiting cumshot

AB105 Christmas Girl's Bondage Party-squiting cumshot

XHamster 2 years ago

Jacob Malik Private Show

HD 2:00 / 15:57

Jacob Malik Private Show

Flirt4Free 1 year ago

Amanda Rosee Private Show

Amanda Rosee Private Show

Camster 11 months ago

Sophia Loreen Private Show

66% HD 2:00 / 9:55

Sophia Loreen Private Show

Flirt4Free 5 months ago

Sissy prolapse Training vacuum Pump

Sissy prolapse Training vacuum Pump

XHamster 2 weeks ago

[FayGrey] Raven trains you to be a cumslut (Femdom cei joi assplay Futa trainer)

[FayGrey] Raven trains you to be a cumslut (Femdom cei joi assplay Futa trainer)

HentaiGem 4 years ago

Sandy Nell Private Show

62% HD 2:00 / 4:19

Sandy Nell Private Show

Flirt4Free 5 years ago

Giving My Juicy Rosebud Some Attention, It Wants to Grow, Become a Huge Prolapse, Falling From My Wrecked Asscunt

Giving My Juicy Rosebud Some Attention, It Wants to Grow, Become a Huge Prolapse, Falling From My Wrecked Asscunt

XHamster 3 months ago

Jhordy & Maxx Private Show

51% HD 2:00 / 53:16

Jhordy & Maxx Private Show

Flirt4Free 1 year ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Camster 1 week ago

IMMENSE DARK-HUED TRUNK PARENT USES CAGED YT SISSYBOY : your Black neighbor gets your sonny high and teaches him to conform

IMMENSE DARK-HUED TRUNK PARENT USES CAGED YT SISSYBOY : your Black neighbor gets your sonny high and teaches him to conform

2BGay 3 years ago

Satans Hour At Cemetery Part 1 ???? Sissy Donk Be Wiggling

Satans Hour At Cemetery Part 1 ???? Sissy Donk Be Wiggling

Gayhub 1 year ago

You're Such a Sexy Sissy Slut for Me

You're Such a Sexy Sissy Slut for Me

XHamster 1 month ago

Chastity stepson Dilon Cum on his Horny Stepmother flesh Stockings Feet - Cock Teasing Shoe High Heels, Lot of Cum on Toes, Pantyhose Footjobs, Cum on Belly, Dangling her Sexy Long Toes, ToeJobs close up, Highly arched soles

64% 4K 0:25 / 16:22

Chastity stepson Dilon Cum on his Horny Stepmother flesh Stockings Feet - Cock Teasing Shoe High Heels, Lot of Cum on Toes, Pantyhose Footjobs, Cum on Belly, Dangling her Sexy Long Toes, ToeJobs close up, Highly arched soles

Clips4sale 11 months ago

Sophia Loreen Party on Sep 10, 2026 - Part 3

4K 2:00 / 23:02

Sophia Loreen Party on Sep 10, 2026 - Part 3

Camster 1 week ago

Sissy Jessica Bloom Teaches You How To Suck Cock And Swallow Cum

Sissy Jessica Bloom Teaches You How To Suck Cock And Swallow Cum

XHamster 1 year ago

Etéreo SissyClown in Puppy Posture using Fake Penis

Etéreo SissyClown in Puppy Posture using Fake Penis

GayCK 4 years ago

Wvm - Trans Girl Gets to Try Her First White Cock

Wvm - Trans Girl Gets to Try Her First White Cock

XHamster 7 months ago

POV/JOI: Your trans friend helps you jerk off to the alternative and original green light, red light game, by pulling dice out of her ass

POV/JOI: Your trans friend helps you jerk off to the alternative and original green light, red light game, by pulling dice out of her ass

XHamster 11 months ago

All that mouth training pays off : facefucking charming transwife Melody

All that mouth training pays off : facefucking charming transwife Melody

Amateur8 1 year ago

Lick the taste of ass from my finger KellyAErick

Lick the taste of ass from my finger KellyAErick

Tranny.one 3 years ago

Sissy Charlotte learns to suck meaty schlong

Sissy Charlotte learns to suck meaty schlong

TrannyGem 4 years ago

Couples Honeymoon Ruined by 2 Dommes

Couples Honeymoon Ruined by 2 Dommes

XHamster 1 month ago

A Boy in a Cage Trains His Boy Pussy for a Halloween Party to Get All the Dicks

A Boy in a Cage Trains His Boy Pussy for a Halloween Party to Get All the Dicks

XHamster 1 year ago

Slap My Horny Ass ^^

Slap My Horny Ass ^^

Camster 1 year ago

Fag Teaching

Transvids.tv 11 months ago

BIG BOOTY Sissy Slut Fucks Eager Hole With Dildo & CUMS

BIG BOOTY Sissy Slut Fucks Eager Hole With Dildo & CUMS

XHamster 3 years ago

4 Fingers Inside My Pussy, Squirt and Finish

59% 4K 2:00 / 1:20:13

4 Fingers Inside My Pussy, Squirt and Finish

Flirt4Free 5 months ago

Sophia Loreen Party on Jul 29, 2026 - Part 3

62% 4K 2:00 / 1:17:55

Sophia Loreen Party on Jul 29, 2026 - Part 3

Flirt4Free 1 month ago

Master & Ithan & Aleex Private Show

52% HD 2:00 / 38:32

Master & Ithan & Aleex Private Show

Flirt4Free 1 year ago

Double Enemas, Custard, Bananas And A Sweet Mess All Over Us Clip 1

Double Enemas, Custard, Bananas And A Sweet Mess All Over Us Clip 1

XHamster 9 months ago

Stretching and Wrecking My Hole on My Fist Dildo I Always Cum to Fast When I Get the Fist Inside Me

HD 0:39 / 12:26

Stretching and Wrecking My Hole on My Fist Dildo I Always Cum to Fast When I Get the Fist Inside Me

FapHouse 1 year ago

Wondrous Fem Dom and Mature Shemale Predominate and Fem a Sissy

Wondrous Fem Dom and Mature Shemale Predominate and Fem a Sissy

TrannyGem 5 years ago

Jhordy & Maxx Private Show

43% HD 2:00 / 33:20

Jhordy & Maxx Private Show

Flirt4Free 1 year ago

Mistress Training Sissy Femboy

Mistress Training Sissy Femboy

Tranny.one 3 years ago

Watch these Big Veiny Dildos Destroy and Ruin my Sissy Asshole until I get Thick Cum Anal Creampies

Watch these Big Veiny Dildos Destroy and Ruin my Sissy Asshole until I get Thick Cum Anal Creampies

XHamster 1 year ago

Brides Hands-free BBC Cumshots

63% HD 0:39 / 4:53

Brides Hands-free BBC Cumshots

FapHouse 4 months ago

Sophia Loreen Private Show

61% 4K 2:00 / 9:47

Sophia Loreen Private Show

Camster 1 month ago

Harris Morrison Private Show

HD 2:00 / 45:59

Harris Morrison Private Show

Flirt4Free 2 years ago

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